US2011172270A1PendingUtilityA1
2-'4(phenylamino)-piperidin-1-yl!-n-phenyl-acetamine derivatives and related compounds as neuropeptide y5 (npy5) ligands for the treatment of obesity
Est. expiryJul 30, 2023(expired)· nominal 20-yr term from priority
Inventors:Antoni TorrensJosep Mas PrioAlberto Dordal ZuerasMaria Angeles Fisas EscasanyHelmut Buschmann
A61P 9/12A61P 3/04A61P 9/00A61P 37/00A61P 5/00A61P 43/00A61P 3/10A61P 25/18A61P 29/00A61P 3/00A61P 25/02A61P 25/04A61P 25/22A61P 25/24A61P 25/28A61P 25/00A61P 25/08A61P 19/02A61P 1/14C04B 35/632C07D 401/12C07D 211/58C07D 405/12
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Claims
Abstract
1,4-disubstituted piperidine compounds of general formula (I) wherein the substituents are defined in claim 1 that are suitable in particular as active substances in medicaments, preferably in medicaments for the regulation of neuropeptide Y receptors, particularly preferably of neuropeptide Y5 (NPY5) receptor, for the regulation of food ingestion (food intake), preferably for the prophylaxis and/or treatment of disorders of food ingestion, such as obesity, anorexia, cachexia, bulimia or type II (non insulin dependent) diabetes, for the prophylaxis and/or treatment of disorders of the peripheral nervous system, disorders of the central nervous system, anxiety, depression, cognitive disorders, preferably memory disorders, cardiovascular diseases, pain, epilepsy, arthritis, hypertensive syndrome, inflammatory diseases, immune diseases and other NPY5 mediated disorders in animals and mammals, including man.
Claims
exact text as granted — not AI-modified1 - 24 . (canceled)
25 . A process for preparing a 1,4-disubstituted piperidine compounds of formula (I)
the process comprising,
reacting at least one compound of general formula (II),
with at least one compound of general formula (III),
F represents halogen, hydroxy or an O-acyl group and G represents halogen, in a suitable reaction medium and optionally in the presence of at least one base and/or at least one auxiliary agent, and reacting the so obtained compound of general (IV)
with at least one piperidine compound of general formula (V) and/or a salt, thereof,
in a suitable reaction medium, optionally in the presence of at least one base and/or at least one auxiliary agent,
wherein
R 1 , R 2 , R 3 , R 4 are each independently selected from the group consisting of hydrogen, halogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, a nitro, cyano, —OR 12 , —OC(═O)R 13 , —SR 14 , —SOR 14 , —SO 2 R 14 , —NH—SO 2 R 14 , —SO 2 NH 2 , —NR 15 R 15 moiety and —O—P,
R 5 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, or a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical,
R 6 , R 7 , R 8 , R 9 are each independently selected from the group consisting of hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, a cyano and a COOR 17 moiety,
A represents a bridge member —CHR 18 — or —CHR 18 —CH 2 —,
B represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, a COOR 19 -moiety, a —(C═O)R 20 -moiety, or a —CH 7 OR 23 -moiety,
R 10 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 11 represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, or an optionally at least mono substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, or
R 10 and R 11 together with the bridging nitrogen atom form an optionally at least mono-substituted, saturated, unsaturated or aromatic heterocyclic ring that may contain at least one further heteroatom as a ring member and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem,
R 12 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 13 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 14 represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 15 and R 16 each are independently selected from the group consisting of hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
or R 15 and R 16 together with the bridging nitrogen atom form a saturated, unsaturated or aromatic heterocyclic ring, which may be at least mono-substituted and/or contain at least one further heteroatom as a ring member,
R 17 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 18 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 19 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 20 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or a NR 21 R 22 -moiety,
R 21 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 22 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 23 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, which may comprise at least one heteroatom as a chain member, or a —(C═O)R 13 -moiety,
P represents hydrogen, a linear or branched C 1-3 alkyl radical,
—PO(O—C 1-4 -Alkyl), —CO(OC 1-5 -Alkyl),
and R P represents —OCO—C 1-3 -Alkyl, —CH 2 —N(C 1-4 -Alkyl) 2 or
optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, its racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers or diastereomers, in any mixing ratio, or a salt.
26 . A process for preparing a 1,4 disubstituted piperidine compound of general formula (I)
wherein B represents a substituted aliphatic radical or a —CH 2 OR 23 -moiety, the process comprising,
reacting at least one compound of general formula (II),
with at least one compound of general formula (III),
wherein F represents halogen, hydroxy or an O-acyl group and G represents halogen in a suitable reaction medium and optionally in the presence of at least one base and/or at least one auxiliary agent, and reacting the so obtained compound of general formula (IV)
with at least one piperidine compound of general formula (V) and/or a salt thereof,
wherein R x represents any substituent including hydrogen in a suitable reaction medium, optionally in the presence of at least one base and/or at least one auxiliary agent, to yield a compound of general formula (VI),
which is reacted with a base in a suitable reaction medium to yield a compound of general formula (I), wherein
R 1 , R 2 , R 3 , R 4 are each independently selected from the group consisting of hydrogen, halogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, a nitro, cyano, —OR 12 , —OC(═O)R 13 , —SR 14 , —SOR 14 , —SO 2 R 14 , —NH—SO 2 R 14 , —SO 2 NH 2 , —NR 15 R 16 moiety and —O—P,
R 5 represents H;
R 6 , R 7 , R 8 , R 9 are each independently selected from the group consisting of hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, a cyano and a COOR 17 moiety,
A represents a bridge member —CHR 18 — or —CHR 18 —CH 2 —,
B represents a substituted aliphatic radical or a —CH 2 OR 23 -moiety.
R 10 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 11 represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, or an optionally at least mono substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, or
R 10 and R 11 together with the bridging nitrogen atom form an optionally at least mono-substituted, saturated, unsaturated or aromatic heterocyclic ring that may contain at least one further heteroatom as a ring member and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem,
R 12 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 13 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 14 represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 15 and R 16 each are independently selected from the group consisting of hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
or R 15 and R 16 together with the bridging nitrogen atom form a saturated, unsaturated or aromatic heterocyclic ring, which may be at least mono-substituted and/or contain at least one further heteroatom as a ring member,
R 17 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 18 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 19 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 20 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or a NR 21 R 22 -moiety,
R 21 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 22 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 23 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, which may comprise at least one heteroatom as a chain member, or a —(C═O)R 13 -moiety,
P represents hydrogen, a linear or branched C 1-3 alkyl radical,
—PO(O—C 1-4 -Alkyl), —CO(OC 1-5 -Alkyl),
and R P represents —OCO—C 1-3 -Alkyl, —CH 2 —N(C 1-4 -Alkyl) 2 or
optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, its racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers or diastereomers, in any mixing ratio, or a salt.
27 . A process for the preparing a physiologically acceptable salt of a 1,4-disubstituted piperidine compound of general formula (I), the process comprising reacting at least one compound of general formula (I) having at least one basic group with at least one acid in the presence of a suitable reaction medium
wherein
R 1 , R 2 , R 3 , R 4 are each independently selected from the group consisting of hydrogen, halogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, a nitro, cyano, —OR 12 , —OC(═O)R 13 , —SR 14 , —SOR 14 , —SO 2 R 14 , —NH—SO 2 R 14 , —SO 2 NH 2 , —NR 15 R 16 moiety and —O—P,
R 5 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, or a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical,
R 6 , R 7 , R 8 , R 9 are each independently selected from the group consisting of hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, a cyano and a COOR 17 moiety,
A represents a bridge member —CHR 18 — or —CHR 18 —CH 2 —,
B represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, a COOR 19 -moiety, a —(C═O)R 20 -moiety, or a —CH 2 OR 23 -moiety,
R 10 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 11 represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, or an optionally at least mono substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, or
R 10 and R 11 together with the bridging nitrogen atom form an optionally at least mono-substituted, saturated, unsaturated or aromatic heterocyclic ring that may contain at least one further heteroatom as a ring member and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem,
R 12 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 13 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 14 represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 15 and R 16 each are independently selected from the group consisting of hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
or R 15 and R 16 together with the bridging nitrogen atom form a saturated, unsaturated or aromatic heterocyclic ring, which may be at least mono-substituted and/or contain at least one further heteroatom as a ring member,
R 17 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 18 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 19 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 20 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or a NR 21 R 22 -moiety,
R 21 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 22 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 23 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, which may comprise at least one heteroatom as a chain member, or a —(C═O)R 13 -moiety,
P represents hydrogen, a linear or branched C 1-3 alkyl radical,
—PO(O—C 1-4 -Alkyl), —CO(OC 1-5 -Alkyl),
and R P represents —OCO—C 1-3 -Alkyl, —CH 2 —N(C 1-4 -Alkyl), or
optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, its racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers or diastereomers, in any mixing ratio, or a salt.
28 . A process for the preparing a physiologically acceptable salt of a 1,4-disubstituted piperidine compound, the method comprising reacting at least one compound of general formula (I) having at least one acidic group with at least one base in the presence of a suitable reaction medium
wherein
R 1 , R 2 , R 3 , R 4 are each independently selected from the group consisting of hydrogen, halogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, a nitro, cyano, —OR 12 , —OC(═O)R 13 , —SR 14 , —SOR 14 , —SO 2 R 14 , —NH—SO 2 R 14 , —SO 2 NH 2 , —NR 15 R 16 moiety and —O—P,
R 5 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, or a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical,
R 6 , R 7 , R 8 , R 9 are each independently selected from the group consisting of hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, a cyano and a COOR 17 moiety,
A represents a bridge member —CHR 18 — or —CHR 18 —CH 2 —,
B represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, a COOR 19 -moiety, a —(C═O)R 20 -moiety, or a —CH 2 OR 23 -moiety,
R 10 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 11 represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, or an optionally at least mono substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, or
R 10 and R 11 together with the bridging nitrogen atom form an optionally at least mono-substituted, saturated, unsaturated or aromatic heterocyclic ring that may contain at least one further heteroatom as a ring member and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem,
R 12 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 13 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 14 represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 15 and R 16 each are independently selected from the group consisting of hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
or R 15 and R 16 together with the bridging nitrogen atom form a saturated, unsaturated or aromatic heterocyclic ring, which may be at least mono-substituted and/or contain at least one further heteroatom as a ring member,
R 17 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 18 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 19 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 20 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or a NR 21 R 22 -moiety,
R 21 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 22 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 23 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, which may comprise at least one heteroatom as a chain member, or a —(C═O)R 13 -moiety,
P represents hydrogen, a linear or branched C 1-3 alkyl radical,
—PO(O—C 1-4 -Alkyl), —CO(OC 1-5 -Alkyl),
and R P represents —OCO—C 1-3 -Alkyl, —CH, —N(C 1-4 -Alkyl), or
optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, its racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers or diastereomers, in any mixing ratio, or a salt.
29 - 56 . (canceled)
57 . A method for regulating a neuropeptide Y receptor in a subject in need thereof, the method comprising administering an effective amount of at least one 1,4-disubstituted piperidine compound according to general formula (I):
wherein
R 1 , R 2 , R 3 , R 4 are each independently selected from the group consisting of hydrogen, halogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, a nitro, cyano, —OR 12 , —OC(═O)R 13 , —SR 14 , —SOR 14 , —SO 2 R 14 , —NH—SO 2 R 14 , —SO 2 NH 2 , —NR 15 R 16 moiety and —O—P,
R 5 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, or a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical,
R 6 , R 7 , R 8 , R 9 are each independently selected from the group consisting of hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, a cyano and a COOR 17 moiety,
A represents a bridge member —CHR 18 — or —CHR 18 —CH 2 —,
B represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, a COOR 19 -moiety, a —(C═O)R 20 -moiety, or a —CH 2 OR 23 -moiety,
R 10 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 11 represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, or an optionally at least mono substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem, or
R 10 and R 11 together with the bridging nitrogen atom form an optionally at least mono-substituted, saturated, unsaturated or aromatic heterocyclic ring that may contain at least one further heteroatom as a ring member and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ringsystem,
R 12 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 13 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 14 represents an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 15 and R 16 each are independently selected from the group consisting of hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
or R 15 and R 16 together with the bridging nitrogen atom form a saturated, unsaturated or aromatic heterocyclic ring, which may be at least mono-substituted and/or contain at least one further heteroatom as a ring member,
R 17 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 18 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted, optionally at least one heteroatom as ring member containing cycloaliphatic radical or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be bonded via an optionally at least mono-substituted alkylene group and/or may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 19 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 20 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system, or a NR 21 R 22 -moiety,
R 21 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 22 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, a saturated or unsaturated, optionally at least mono-substituted cycloaliphatic radical, or an optionally at least mono-substituted aryl- or heteroaryl radical, which may be condensed with an optionally at least mono-substituted mono- or polycyclic ring-system,
R 23 represents hydrogen, an unbranched or branched, saturated or unsaturated, optionally at least mono-substituted aliphatic radical, which may comprise at least one heteroatom as a chain member, or a —(C═O)R 13 -moiety,
P represents hydrogen, a linear or branched C 1-3 alkyl radical,
—PO(O—C 1-4 -Alkyl), —CO(OC 1-5 -Alkyl),
and R P represents —OCO—C 1-3 -Alkyl, —CH 2 —N(C 1-4 -Alkyl) 2 or
optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, its racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers or diastereomers, in any mixing ratio, or a salt.
58 . The method of claim 57 , wherein the neuropeptide Y receptor is a neuropeptide Y 5 (NPY5) receptor.
59 . The method of claim 56 , wherein the administering treats at least one condition in the subject selected from the group consisting of appetite, body weight, food ingestion (food intake), obesity, anorexia, cachexia, bulimia, type (II) diabetes, a disorder of the peripheral nervous system, a disorder of the central nervous system, arthritis, epilepsy, anxiety, depression, cognitive disorders, cardiovascular disease, pain, hypertensive syndrome, an inflammatory disease, an immune disease, a panic attack, a bipolar disorder, diabetes, and improvement of cognition.
60 . The process of claim 25 , wherein R 1 , R 2 , R 3 , R 4 are each independently selected from the group consisting of H, F, Cl, Br, OH, CH 3 , and OCH 3 , B represents a —CH 2 —OH or —(C═O)—O—CH 3 group,
R 11 is selected from the group consisting of unsubstituted phenyl, phenyl that is optionally at least mono-substituted with one or more substituents independently selected from the group consisting of cyclohexyl, phenyl, phenoxy, benzoyl, —C(═O)—C 1-2 -alkyl, —C(H)(OH)(phenyl) and —C(H)(OH)(CH 3 ),
a group of formula (A)
wherein
n is 1 or 2,
X represents CH,
Y represents CH—OH or C(═O),
a group of formula (B),
a group of formula (C),
and a group of formula (E),
wherein
R E represents H, a branched or unbranched C 1-4 -alkyl radical or a branched or unbranched C 1-4 -alkoxy radical,
Z represents CH 2 , O, S, CH—OH, C(═O) or N—R F where R F represents H or a branched or unbranched C 1-4 -alkyl-radical,
optionally in form of one of its stereoisomers, its racemate or in form of a mixture of at least two of its stereoisomers, or a salt.
61 . The process according to claim 25 , wherein the 1,4-disubstituted compound of general formula (I) is selected from the group consisting of:
1
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
2
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
3
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
4
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
5
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
6
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
7
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
8
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
9
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
10
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
11
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
12
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
13
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
14
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
15
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-acetamide
16
N-Benzo[1,3] dioxol-5-yl-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
17
N-Benzo[1,3]dioxol-5-yl-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
18
N-Benzo[1,3]dioxol-5-yl-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-acetamide hydrochloride
19
2-[4-(4-Chioro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
20
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
21
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
22
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
23
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
24
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
25
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
26
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
27
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
28
2-[4-(2-Hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
29
2-[4-(4,5-Difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
30
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
31
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
32
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
33
N-(4-Benzoyl-phenyl)-2-[4-(4-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
34
N-(4-Benzoyl-phenyl)-2-[4-(4-fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
35
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-acetamide
36
N-(4-Benzoyl-phenyl)-2-14-(3-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
37
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-phenyl]-acetamide
38
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-phenyl]-acetamide
39
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-phenyl]-acetamide
40
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-phenyl]-acetamide
41
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-phenyl]-acetamide
42
2-[4-(2-Hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-phenyl]-acetamide
43
2-[4-(3-Chloro-2-hydroxytnethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-phenyl]-acetamide
44
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-yl)-acetamide
45
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-yl)-acetamide
46
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-yl)-acetamide
47
2-[4-(2-Hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-yl)-acetamide
48
2-[4-(4,5-Difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-yl)-acetamide
49
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-yl)-acetamide
50
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
51
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-hydroxy-9H-fluoren-3-yl)-acetamide
52
2-[4-(4-Fiuoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-hydroxy-9H-fluoren-3-yl)-acetamide
53
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(2-hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-acetamide
54
2-[4-(4,5-Difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-hydroxy-9H-fluoren-3-yl)-acetamide
55
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-hydroxy-9H-fluoren-3-yl)-acetamide
56
N-(3-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
57
N-(3-Acetyl-phenyl)-2-[4-(2-hydroxymethyi-6-methyl-phenylamino)-piperidin-1-yl]-acetamide
58
N-(3-Acetyl-phenyl)-2-[4-(4-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
59
N-(3-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
60
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
61
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-acetamide
62
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[3-(1-hydroxy-ethyl)-phenyl]-acetamide
63
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
64
N-Benzo[1,3]dioxol-5-yl-2-[4-(4-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
65
N-Benzo[1,3]dioxol-5-yl-2-[4-(4-fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
66
N-Benzo[1,3] dioxol-5-yl-2-[4-(2-hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-acetamide
67
N-Benzo[1,3]dioxol-5-yl-2-[4-(4,5-difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
68
N-Benzo[1,3]dioxol-5-yl-2-[4-(3-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
69
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
70
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-acetamide
71
N-(4-Acetyl-phenyl)-2-[4-(4-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
72
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
73
N-(4-Acetyl-phenyl)-2-[4-(4-fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
74
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-acetamide
75
N-(4-Acetyl-phenyl)-2-[4-(3-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
76
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
77
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-acetamide
78
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(1-hydroxy-ethyl)-phenyl]-acetamide
79
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
80
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(1-hydroxy-ethyl)-phenyl]-acetamide
81
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-6-methOxy-phenylamino)-piperidin-1-yl]-acetamide
82
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(1-hydroxy-ethyl)-phenyl-acetamide
83
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
84
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-ethyl-9H-carbazol-3-yl)-acetamide
85
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
86
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(4-fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
87
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(2-hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-acetamide
88
2-[4-(4,5-Difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-ethyl-9H-carbazol-3-yl)-acetamide
89
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-ethyl-9H-carbazol-3-yl)-acetamide
90
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-methyl-9H-carbazol-3-yl)-acetamide
91
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(9-methyl-9H-carbazol-3-yl)-acetamide
92
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-methyl-9H-carbazol-3-yl)-acetamide
93
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(9-methyl-9H-carbazol-3-yl)-acetamide
94
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide
95
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
96
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamde
97
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
98
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
99
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide
100
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamde
101
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
102
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
103
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)
104
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(1-oxo-indan-5-yl)-acetamide
105
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(1-oxo-indan-5-yl)-acetamide
106
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(1-oxo-indan-5-yl)-acetamide
107
N-(1-Hydroxy-indan-5-yl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
108
N-(1-Hydroxy-indan-5-yl)-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-acetamide
109
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(1-hydroxy-indan-5-yl)-acetamide
110
N-(1-Hydroxy-indan-5-yl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
111
2-[4-(4-Bromo-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-ethYl-9H-carbazol-3-yl)-acetamide
112
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-2-yl)-acetamide
113
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-2-YI)-acetamide
114
N-Dibenzofuran-2-yl-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
115
N-Dibenzofuran-2-yl-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-acetamide
116
2-[4-(2-Hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
117
2-[4-(4,5-Difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
118
N-(9-Hydroxy-9H-fluoren-2-yl)-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-acetamide
119
N-(9-Hydroxy-9H-fluoren-2-yl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
120
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
121
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
122
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
123
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
124
N-(4-Cyclohexyl-phenyl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
125
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
126
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
127
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
128
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
129
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
130
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
131
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
132
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
133
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-acetamide
134
N-(4-Benzoyl-phenyl)-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
135
N-(4-Benzoyl-phenyl)-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
136
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
137
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-phenyl]-acetamide
138
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-phenyl]-acetamide
139
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-phenyl-acetamide
140
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-phenyl]-acetamide
141
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-yl)-acetamide
142
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-yl)-acetamide
143
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-yl)-acetamide
144
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-yl)-acetamide
145
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-acetamide
146
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
147
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
148
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
149
N-(3-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-acetamide
150
N-(3-Acetyl-phenyl)-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
151
N-(3-Acetyl-phenyl)-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
152
N-(3-Acetyl-phenyl)-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
153
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-acetamide
154
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
155
N-3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
156
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
157
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-acetamide
158
N-(4-Acetyl-phenyl)-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
159
N-(4-Acetyl-phenyl)-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
160
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
161
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-acetamide
162
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
163
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
164
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
165
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-acetamide
166
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
167
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
168
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
169
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
170
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamde
171
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
172
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
173
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
174
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
175
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
176
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl)acetamide
177
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
178
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
179
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
180
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, its racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers or diastereomers, in any mixing ratio, or a salt thereof.
62 . The process of claim 57 , wherein R 1 , R 2 , R 3 , R 4 are each independently selected from the group consisting of H, F, Cl, Br, OH, CH 3 , and OCH 3 , B represents a —CH 2 —OH or —(C═O)—O—CH 3 group,
R 11 is selected from the group consisting of unsubstituted phenyl, phenyl that is optionally at least mono-substituted with one or more substituents independently selected from the group consisting of cyclohexyl, phenyl, phenoxy, benzoyl, —C(═O)—C 1-2 -alkyl, —C(H)(OH)(phenyl) and —C(H)(OH)(CH 3 ),
a group of formula (A)
wherein
n is 1 or 2,
X represents CH,
Y represents CH—OH or C(═O),
a group of formula (B),
a group of formula (C),
and a group of formula (E),
wherein
R E represents H, a branched or unbranched C 1-4 -alkyl radical or a branched or unbranched C 1-4 -alkoxy radical,
Z represents CH 2 , O, S, CH—OH, C(═O) or N—R F where R F represents H or a branched or unbranched C 1-4 -alkyl-radical,
optionally in form of one of its stereoisomers, its racemate or in form of a mixture of at least two of its stereoisomers, or a salt.
63 . The process according to claim 57 , wherein the 1,4-disubstituted compound of general formula (I) is selected from the group consisting of:
1
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
2
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
3
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
4
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
5
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
6
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
7
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
8
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
9
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
10
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
11
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
12
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
13
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
14
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
15
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-acetamide
16
N-Benzo[1,3] dioxol-5-yl-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
17
N-Benzo[1,3]dioxol-5-yl-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-
acetamide
18
N-Benzo[1,3]dioxol-5-yl-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-
acetamide hydrochloride
19
2-[4-(4-Chioro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
20
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
21
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
22
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
23
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
24
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-5-yl-acetamide
25
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
26
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
27
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
28
2-[4-(2-Hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
29
2-[4-(4,5-Difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
30
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
31
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
32
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-8-yl-acetamide
33
N-(4-Benzoyl-phenyl)-2-[4-(4-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
34
N-(4-Benzoyl-phenyl)-2-[4-(4-fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
35
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-acetamide
36
N-(4-Benzoyl-phenyl)-2-14-(3-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
37
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-methyl)-
phenyl]-acetamide
38
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-
methyl)-phenyl]-acetamide
39
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-
methyl)-phenyl]-acetamide
40
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-
methyl)-phenyl]-acetamide
41
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-
methyl)-phenyl]-acetamide
42
2-[4-(2-Hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-
methyl)-phenyl]-acetamide
43
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-
methyl)-phenyl]-acetamide
44
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-yl)-acetamide
45
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-
yl)-acetamide
46
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-
yl)-acetamide
47
2-[4-(2-Hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-
yl)-acetamide
48
2-[4-(4,5-Difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-
3-yl)-acetamide
49
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-
yl)-acetamide
50
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
51
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-hydroxy-9H-fluoren-
3-yl)-acetamide
52
2-[4-(4-Fiuoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-hydroxy-9H-fluoren-
3-yl)-acetamide
53
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(2-hydroxymethyl-6-methoxy-phenylamino)-
piperidin-1-yl]-acetamide
54
2-[4-(4,5-Difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-hydroxy-9H-
fluoren-3-yl)-acetamide
55
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-hydroxy-9H-fluoren-
3-yl)-acetamide
56
N-(3-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
57
N-(3-Acetyl-phenyl)-2-[4-(2-hydroxymethyi-6-methyl-phenylamino)-piperidin-1-yl]-acetamide
58
N-(3-Acetyl-phenyl)-2-[4-(4-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
59
N-(3-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
60
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-
acetamide
61
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-
piperidin-1-yl]-acetamide
62
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[3-(1-hydroxy-ethyl)-
phenyl]-acetamide
63
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-
piperidin-1-yl]-acetamide
64
N-Benzo[1,3]dioxol-5-yl-2-[4-(4-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-
acetamide
65
N-Benzo[1,3]dioxol-5-yl-2-[4-(4-fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-
acetamide
66
N-Benzo[1,3] dioxol-5-yl-2-[4-(2-hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-
yl]-acetamide
67
N-Benzo[1,3]dioxol-5-yl-2-[4-(4,5-difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-
yl]-acetamide
68
N-Benzo[1,3]dioxol-5-yl-2-[4-(3-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-
acetamide
69
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
70
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-acetamide
71
N-(4-Acetyl-phenyl)-2-[4-(4-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
72
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-acetamide
73
N-(4-Acetyl-phenyl)-2-[4-(4-fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
74
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-acetamide
75
N-(4-Acetyl-phenyl)-2-[4-(3-chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
76
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-
acetamide
77
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-
piperidin-1-yl]-acetamide
78
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(1-hydroxy-ethyl)-
phenyl]-acetamide
79
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-
piperidin-1-yl]-acetamide
80
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(1-hydroxy-ethyl)-
phenyl]-acetamide
81
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-6-methOxy-phenylamino)-pipe
ridin-1-yl]-acetamide
82
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(1-hydroxy-ethyl)-
phenyl-acetamide
83
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-
acetamide
84
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-ethyl-9H-carbazol-3-
yl)-acetamide
85
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-
1-yl]-acetamide
86
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(4-fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-
yl]-acetamide
87
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(2-hydroxymethyl-6-methoxy-phenylamino)-
piperidin-1-yl]-acetamide
88
2-[4-(4,5-Difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-ethyl-9H-
carbazol-3-yl)-acetamide
89
2-[4-(3-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-ethyl-9H-carbazol-3-
yl)-acetamide
90
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-methyl-9H-carbazol-3-yl)-acetamide
91
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(9-methyl-9H-
carbazol-3-yl)-acetamide
92
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-methyl-9H-carbazol-
3-yl)-acetamide
93
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(9-methyl-9H-
carbazol-3-yl)-acetamide
94
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-tetrahydro-
naphthalen-2-yl)-acetamide
95
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
96
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamde
97
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
98
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
99
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-tetrahydro-
naphthalen-2-yl)-acetamide
100
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamde
101
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
102
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
103
2-[4-(4-Fluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-
tetrahydro-naphthalen-2-yl)
104
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(1-oxo-indan-5-yl)-
acetamide
105
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(1-oxo-indan-5-yl)-
acetamide
106
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(1-oxo-indan-5-yl)-
acetamide
107
N-(1-Hydroxy-indan-5-yl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
108
N-(1-Hydroxy-indan-5-yl)-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-
yl]-acetamide
109
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(1-hydroxy-indan-5-
yl)-acetamide
110
N-(1-Hydroxy-indan-5-yl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-
yl]-acetamide
111
2-[4-(4-Bromo-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-ethYl-9H-carbazol-
3-yl)-acetamide
112
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-2-
yl)-acetamide
113
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-2-
YI)-acetamide
114
N-Dibenzofuran-2-yl-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-
acetamide
115
N-Dibenzofuran-2-yl-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-
acetamide
116
2-[4-(2-Hydroxymethyl-6-methoxy-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
117
2-[4-(4,5-Difluoro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
118
N-(9-Hydroxy-9H-fluoren-2-yl)-2-[4-(2-hydroxymethyl-6-methyl-phenylamino)-
piperidin-1-yl]-acetamide
119
N-(9-Hydroxy-9H-fluoren-2-yl)-2-[4-(2-hydroxymethyl-4-methyl-phenylamino)-
piperidin-1-yl]-acetamide
120
2-[4-(2-Hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
121
2-[4-(2-Hydroxymethyl-6-methyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
122
2-[4-(4-Chloro-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
123
2-[4-(2-Hydroxymethyl-4-methyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-acetamide
124
N-(4-Cyclohexyl-phenyl)-2-[4-(2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
125
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
126
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
127
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
128
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-3-yl-acetamide
129
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
130
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
131
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
132
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-quinolin-6-yl-acetamide
133
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-acetamide
134
N-(4-Benzoyl-phenyl)-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
135
N-(4-Benzoyl-phenyl)-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
136
N-(4-Benzoyl-phenyl)-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
137
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-
methyl)-phenyl]-acetamide
138
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-
methyl)-phenyl]-acetamide
139
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-
methyl)-phenyl-acetamide
140
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-[4-(hydroxy-phenyl-
methyl)-phenyl]-acetamide
141
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-
yl)-acetamide
142
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-
yl)-acetamide
143
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-
yl)-acetamide
144
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(9-oxo-9H-fluoren-3-
yl)-acetamide
145
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-
piperidin-1-yl]-acetamide
146
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-
piperidin-1-yl]-acetamide
147
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-
piperidin-1-yl]-acetamide
148
N-(9-Hydroxy-9H-fluoren-3-yl)-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-
piperidin-1-yl]-acetamide
149
N-(3-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-acetamide
150
N-(3-Acetyl-phenyl)-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
151
N-(3-Acetyl-phenyl)-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
152
N-(3-Acetyl-phenyl)-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
153
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-
piperidin-1-yl]-acetamide
154
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-
piperidin-1-yl]-acetamide
155
N-3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-
piperidin-1-yl]-acetamide
156
N-[3-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-
piperidin-1-yl]-acetamide
157
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-acetamide
158
N-(4-Acetyl-phenyl)-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
159
N-(4-Acetyl-phenyl)-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
160
N-(4-Acetyl-phenyl)-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-acetamide
161
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-
piperidin-1-yl]-acetamide
162
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-
piperidin-1-yl]-acetamide
163
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-
piperidin-1-yl]-acetamide
164
N-[4-(1-Hydroxy-ethyl)-phenyl]-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-
piperidin-1-yl]-acetamide
165
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(2-hydroxymethyl-3-methoxy-phenylamino)-
piperidin-1-yl]-acetamide
166
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(3-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-
1-yl]-acetamide
167
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(4-hydroxy-2-hydroxymethyl-phenylamino)-piperidin-
1-yl]-acetamide
168
N-(9-Ethyl-9H-carbazol-3-yl)-2-[4-(2-hydroxy-6-hydroxymethyl-phenylamino)-piperidin-
1-yl]-acetamide
169
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
170
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamde
171
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
172
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-oxo-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
173
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
174
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
175
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
176
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(5-hydroxy-5,6,7,8-
tetrahydro-naphthalen-2-yl)acetamide
177
2-[4-(2-Hydroxymethyl-3-methoxy-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-
acetamide
178
2-[4-(3-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-
acetamide
179
2-[4-(4-Hydroxy-2-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-
acetamide
180
2-[4-(2-Hydroxy-6-hydroxymethyl-phenylamino)-piperidin-1-yl]-N-(4-phenoxy-phenyl)-
acetamide
optionally in form of one of its stereoisomers, preferably enantiomers or diastereomers, its racemate or in form of a mixture of at least two of its stereoisomers, preferably enantiomers or diastereomers, in any mixing ratio, or a salt, preferably a physiologically acceptable salt thereofCited by (0)
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