US2007043051A1PendingUtilityA1
Methods and compositions of novel triazine compounds
Individually held — no corporate assignee on recordPriority: Sep 21, 2001Filed: Oct 5, 2006Published: Feb 22, 2007
Est. expirySep 21, 2021(expired)· nominal 20-yr term from priority
A61P 5/14A61P 3/10A61P 3/06A61P 37/02A61P 37/08A61P 9/10A61P 43/00A61P 37/04A61P 7/04A61P 5/00A61P 37/06A61P 7/06A61P 35/04A61P 35/02A61P 35/00A61P 29/00A61P 31/04A61P 25/00A61P 25/28A61P 27/02A61P 31/10A61K 31/53C07F 9/65583C07D 403/12C07D 403/04C07D 401/14C07D 251/30C07D 413/14A61P 1/04C07D 405/12A61P 1/16C07D 409/14A61P 11/06C07D 251/66C07D 487/04A61P 17/00C07D 413/04A61P 1/18C07D 401/12A61P 11/00C07D 251/44C07F 9/6521A61P 13/12A61P 17/06C07D 251/50C07D 251/46A61P 11/02A61P 17/02A61P 15/00A61P 19/10A61P 17/14C07D 453/02C07D 251/52C07D 403/14A61P 17/04A61P 19/02C07D 417/12C07D 405/14C07D 417/14C07D 401/04C07D 251/70C07D 409/12A61P 13/02A61P 21/04C07D 417/04C07D 251/48
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Claims
Abstract
The present invention relates to methods and compositions comprising compounds that treat pathophysiological conditions arising from inflammatory responses. In particular, the present invention is directed to compounds that inhibit or block glycated protein produced induction of the signaling-associated inflammatory response in endothelial cells. The present invention relates to compounds that inhibit smooth muscle proliferation. In particular, the present invention is directed to compounds that inhibit smooth muscle cell proliferation by modulating HSPGs such as Perlecan. The present invention further relates to the use of compounds to treat vascular occlusive conditions characterized by smooth muscle proliferation such as restenosis and atherosclerosis.
Claims
exact text as granted — not AI-modified1 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 , in each occurrence, is selected independently from R 1A , R 1B , R 1C , or R 1D ;
b) R 1A is hydrogen, fluoride, chloride, bromide, iodide, or amino;
c) R 1B is selected from:
i) a substituted or an unsubstituted cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, or an unsubstituted alkyl, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl; or
ii) a substituted alkyl having up to 12 carbon atoms, wherein any substituent is selected independently from: an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
d) R 1C a substituted or an unsubstituted naphthyl, tetrahydronaphthyl, anthracenyl, aryloxide, or arylthiolate, wherein the aryl group in any of the aryloxide or arylthiolate is selected from a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, or an anthracenyl;
wherein any substituent on R 1C , in each occurrence, is selected independently from: a C 1 -C 12 alkoxy, a fluoride, a chloride, a bromide, or an iodide;
e) R 1D is furanyl, benzofuranyl, dibenzofuranyl, thienyl, pyrrolyl, indolinyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, isoxazolidinonyl, thiazolyl, benzothiazolyl, pyridinyl, quinolinyl, rhodaninyl, thiolactonyl, triazinyl, indonyl, pyrrolidinyl, N—(C 1 -C 12 alkyl)pyrrolidinyl, piperidinyl, homopiperidinyl, 2-(methoxymethyl)pyrrolidinyl, piperazinyl, 1,3-dioxolanyl, azepanyl, morpholinyl, tetrahydrofuranyl, decahydroquinolinyl, azabicyclo[3.2.1]octyl, azabicyclo[2.2.2]octyl, or azabicyclo[2.2.1]octyl;
f) G is NR 1 or O;
g) E is CH or N;
h) z is 0, 1, or 2;
i) X 1 is selected from hydrogen, fluoride, chloride, bromide, iodide, R 1B1 , R 1C , R 1D , NR 1 3 + , CN, NO 2 , CO 2 H, CO 2 R 1B2 , CO 2 R 1C , CO 2 R 1D , CH═CR 1 2 , C≡CR 1 , C(O)H, C(O)F, C(O)Br, C(O)I, C(O)R 1B3 , C(O)R 1C , C(O)R 1D , SO 2 H, SO 2 F, SO 2 Cl, SO 2 Br, SO 2 I, SO 2 R 1B , SO 2 R 1C , SO 2 R 1D , SO 2 OR 1 , NHC(O)R 1A , NHC(O)R 1B2 , NHC(O)R 1C , or NHC(O)R 1D , or X 1 and X 2 together is a fused phenyl, tolyl, xylyl, pyridine, dioxane, pyrrole, pyrrolidine, furan, or thiophene ring;
j) R 1B1 is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B1 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
k) R 1B2 is a substituted or an unsubstituted cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B2 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
l) R 1B3 is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkylthio, each of which having up to 12 carbon atoms and including linear or branched analogs thereof,
wherein any substituent on R 1B3 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
m) X 2 is selected from hydrogen; fluoride; chloride; bromide; iodide; R 1B ; R 1C ; R 1D ; CX x H 3-x , wherein X is a halogen and x is 0, 1, 2, or 3; OR 1 ; SR 1 ; NR 1 R 1E ; CN; C(O)OH, C(O)OR 1B2 ; C(O)OR 1C ; C(O)OR 1D ; NHC(O)R 1A ; NHC(O)R 1B2 ; NHC(O)R 1C ; NHC(O)R 1D ; 4-morpholinyl; 4-methyl-1-piperazinyl; OR 2 , wherein R 2 is selected from CH 2 OCH 3 , CH 2 OCH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CH 2 SCH 3 , or C(O)R 1 ; SR 3 , wherein R 3 is selected from CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CH 2 OCH 2 CH(CH 3 ) 2 , CH 2 NHC(O)CH 3 , or SR 1 ; OM or SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
n) R 1E , in each occurrence, is selected independently from fluoride, chloride, bromide, iodide, amino, R 1B , R 1C , or R 1D ;
o) either: 1) AY 1 in combination is fluoride, chloride, bromide, or iodide; or
2) A is NR 1 or O, and Y 1 is selected from:
a. R 1 , CR 4 3 , NR 4 2 , OR 4 , or SR 4 ; or
wherein n is an integer from 0 to 8 inclusive, m is an integer from 1 to 8 inclusive, Z 1 is independently selected from CR 1 or N, Z 2 is independently selected from CR 1 2 , NR 1 , O, or S, with the provisos that two O or S atoms are not located adjacent t to each other and no more than two Z 2 moieties are NR 1 ;
p) R 4 , in each occurrence, is selected independently from R 4A , R 4B , R 4C , or R 4D ;
q) R 4A is hydrogen, fluoride, chloride, bromide, iodide, or amino;
r) R 4B is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 10 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 4B , in each occurrence, is selected independently from: an amino, a di(C 1 -C 12 alkyl)amino, a C 1 -C 12 alkoxy, a C 1 -C 12 alkylthiolate, a fluoride, a chloride, a bromide, or an iodide;
s) R 4C a substituted or an unsubstituted naphthyl, tetrahydronaphthyl, anthracenyl, aryloxide, or arylthiolate, wherein the aryl group in any of the aryloxide or arylthiolate is selected from a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, or an anthracenyl;
wherein any substituent on R 4C , in each occurrence, is selected independently from: a C 1 -C 12 alkoxy, a fluoride, a chloride, a bromide, or an iodide; or
t) R 4D is furanyl, benzofuranyl, dibenzofuranyl, thienyl, pyrrolyl, indolinyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, isoxazolidinonyl, thiazolyl, benzothiazolyl, pyridinyl, quinolinyl, rhodaninyl, thiolactonyl, triazinyl, or indonyl;
u) either: 1) DY 2 in combination is fluoride, chloride, bromide, or iodide; or
2) D is NR 1 or O, and Y 2 is selected from R 1 ,
wherein Z 3 is selected independently from CR 4 or N, and Z 4 is selected independently from CR 1 2 , NR 1 , O, or S, with the provisos that two O or S atoms are not located adjacent to each other and no more than two Z 4 moieties are NR 1 ; and
with the further proviso that the compound excludes
N-Cycloheptyl-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine;
N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine;
[4-(4-Benzyl-piperazin-1-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-(4-methoxy-phenyl)-amine;
N-Cycloheptyl-6-morpholin-4-yl-N′-naphthalen-2-yl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-6-morpholin-4-yl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-6-morpholin-4-yl-N′-phenyl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-N′-(4-methoxy-phenyl)-6-morpholin-4-yl-[1,3,5]triazine-2,4-diamine;
N-Benzyl-N′-cycloheptyl-N″-(4-methoxy-phenyl)-N-methyl-[1,3,5]triazine-2,4,6-triamine;
N-(2-[1,3]Dioxolan-2-yl-ethyl)-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine; and
N-Cyclopropyl-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine.
2 . A compound according to claim 1 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 H, m-SO 2 F, M-SO 2 Cl, m-SO 2 Br, m-SO 2 I, m-SO 2 R 1B , m-SO 2 R 1C , m-SO 2 R 1D , m-SO 2 OR 1 , m-NHC(O)R 1A , m-NHC(O)R 1B2 , m-NHC(O)R 1C , m-NHC(O)R 1D , or o-F, or X 1 and X 2 together is a fused phenyl, pyridine, or dioxane ring; and
X 2 is selected from H, o-F, o-Cl, o-Br, o-I, o-CF 3 , o-R 1B , o-R 1C , o-R 1D , p-OR 1 , p-SR 1 , p-NR 1 R 1E , p-F, p-Cl, p-Br, p-CF 3 , p-CN, p-C(O)OH, p-C(O)OR 1B2 , p-C(O)OR 1C , p-C(O)OR 1D , p-NHC(O)R 1A , p-NHC(O)R 1B2 , p-NHC(O)R 1C , p-NHC(O)R 1D , p-(4-morpholinyl), p-(4-methyl-1-piperazinyl), or p-OM or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca.
3 . A compound according to claim 1 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) A is NR 1 ;
b) Y 1 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
wherein n is 1 or 2;
wherein x is 3, 4, or 5;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
c) D is NR 1 ;
d) Y 2 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
(CHR 1A ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
and
e) R 1A , in each occurrence, is selected independently from a linear or a branched alkyl having up to 10 carbon atoms.
4 . A compound according to claim 1 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 H, m-SO 2 F, m-SO 2 Cl, m-SO 2 Br, m-SO 2 I, m-SO 2 R 1B , m-SO 2 R 1C , m-SO 2 R 1D , m-S 2 OR 1 , m-NHC(O)R 1A , m-NHC(O)R 1B2 , m-NHC(O)R 1C , m-NHC(O)R 1D , or o-F, or X 1 and X 2 together is a fused phenyl, pyridine, or dioxane ring;
b) X 2 is selected from H, o-F, o-Cl, o-Br, o-I, o-CF 3 , o-R 1B , o-R 1C , o-R 1D , p-OR 1 , p-SR 1 , p-NR 1 R 1E , p-F, p-Cl, p-Br, p-CF 3 , p-CN, p-C(O)OH, p-C(O)OR 1B2 , p-C(O)OR 1C , p-C(O)OR 1D , p-NHC(O)R 1A , p-NHC(O)R 1B2 , p-NHC(O)R 1C , p-NHC(O)R 1D , p-(4-morpholinyl), p-(4-methyl-1-piperazinyl), or p-OM or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
c) A is NR 1 ;
d) Y 1 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
wherein n is 1 or 2;
wherein x is 3, 4, or 5;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
e) D is NR 1 ;
f) Y 2 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
(CHR 1A ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
and
g) R 1A , in each occurrence, is selected independently from a linear or a branched alkyl having up to 10 carbon atoms.
5 . A compound according to claim 1 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 is in each occurrence independently selected from H, Me; or (CH 2 ) x CN, wherein x is 1 or 2;
b) E is CH;
c) n is 0;
d) X 1 is H or o-F, or X 1 and X 2 together is a fused benzene ring;
e) X 2 is H, o-CF 3 , p-OR 1 , p-F, or p-Cl;
f) AY 1 in combination is
and
g) DY 2 in combination is
6 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 1 .
7 . The pharmaceutical composition as claimed in claim 6 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
8 . The pharmaceutical composition as claimed in claim 6 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
9 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 , in each occurrence, is selected independently from R 1A , R 1B , R 1C , or R 1D ;
b) R 1A is hydrogen, fluoride, chloride, bromide, iodide, or amino;
c) R 1B is selected from:
i) a substituted or an unsubstituted cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 12 carbon atoms and including linear or branched analogs thereof,
wherein any substituent on R 1B , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl; or
ii) a substituted alkyl having up to 12 carbon atoms, wherein any substituent is selected independently from: an acyl, a formyl, an acyl halide, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
d) R 1C a substituted or an unsubstituted naphthyl, tetrahydronaphthyl, anthracenyl, aryloxide, or arylthiolate, wherein the aryl group in any of the aryloxide or arylthiolate is selected from a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, or an anthracenyl;
wherein any substituent on R 1C , in each occurrence, is selected independently from: a C 1 -C 12 alkoxy, a fluoride, a chloride, a bromide, or an iodide; or
e) R 1D is benzofuranyl, dibenzofuranyl, indolyl, indolinyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, isoxazolidinonyl, thiazolyl, benzothiazolyl, quinolinyl, rhodaninyl, thiolactonyl, triazinyl, indonyl, 2-(methoxymethyl)pyrrolidinyl, N—(C 1 -C 12 alkyl)pyrrolidinyl, 1,3-dioxolanyl, azepanyl, decahydroquinolinyl, azabicyclo[3.2.1]octyl, azabicyclo[2.2.2]octyl, or azabicyclo[2.2.1]octyl;
f) G is NR 1 or O;
g) E is CH or N;
h) z is 0, 1, or 2;
i) X 1 is selected from hydrogen, fluoride, chloride, bromide, iodide, R 1B1 , R 1C , R 1D , NR 1 3 + , CN, NO 2 , CO 2 H, CO 2 R 1B2 , CO 2 R 1C , CO 2 R 1D , CH═CR 1 2 , C≡CR 1 , C(O)H, C(O)F, C(O)Br, C(O)I, C(O)R 1B3 , C(O)R 1C , C(O)R 1D , SO 2 H, SO 2 F, SO 2 Cl, SO 2 Br, SO 2 I, SO 2 R 1B , SO 2 R 1C , SO 2 R 1D , SO 2 OR 1 , NHC(O)R 1A , NHC(O)R 1B2 , NHC(O)R 1C , or NHC(O)R 1D , or X 1 and X 2 together is a fused phenyl, tolyl, xylyl, pyridine, dioxane, pyrrole, pyrrolidine, furan, or thiophene ring;
j) R 1B1 is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B1 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
k) R 1B2 is a substituted or an unsubstituted cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B2 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
l) R 1B3 is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkylthio, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B3 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
m) X 2 is selected from hydrogen; fluoride; chloride; bromide; iodide; R 1B ; R 1C ; R 1D ; CX x H 3-x , wherein X is a halogen and x is 0, 1, 2, or 3; OR 1 ; SR 1 ; NR 1 R 1E ; CN; C(O)OH, C(O)OR 1B2 ; C(O)OR 1C ; C(O)OR 1D ; NHC(O)R 1A ; NHC(O)R 1B2 ; NHC(O)R 1C ; NHC(O)R 1D ; 4-morpholinyl; 4-methyl-1-piperazinyl; OR 2 , wherein R 2 is selected from CH 2 OCH 3 , CH 2 OCH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CH 2 SCH 3 , or C(O)R 1 ; SR 3 , wherein R 3 is selected from CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CH 2 OCH 2 CH(CH 3 ) 2 , CH 2 NHC(O)CH 3 , or SR 1 ; OM or SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
n) R 1E , in each occurrence, is selected independently from fluoride, chloride, bromide, iodide, amino, R 1B , R 1C , or R 1D ;
o) either: 1) AY 1 in combination is fluoride, chloride, bromide, or iodide; or
2) A is NR 1 or O, and Y 1 is selected from:
a. R 1 , CR 4 3 , NR 4 2 , OR 4 , or SR 4 ; or
wherein n is an integer from 0 to 8 inclusive, m is an integer from 1 to 8 inclusive, Z 1 is independently selected from CR 1 or N, Z 2 is independently selected from CR 1 2 , NR 1 , O, or S, with the provisos that two O or S atoms are not located adjacent t to each other and no more than two Z 2 moieties are NR 1 ;
p) R 4 , in each occurrence, is selected independently from R 4A , R 4B , R 4C , or R 4D ;
q) R 4A is hydrogen, fluoride, chloride, bromide, iodide, or amino;
r) R 4B is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 10 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 4B , in each occurrence, is selected independently from: an amino, a C 1 -C 12 alkylthiolate, a fluoride, a chloride, a bromide, or an iodide;
s) R 4C a substituted or an unsubstituted naphthyl, tetrahydronaphthyl, anthracenyl, aryloxide, or arylthiolate, wherein the aryl group in any of the aryloxide or arylthiolate is selected from a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, or an anthracenyl;
wherein any substituent on R 4C , in each occurrence, is selected independently from: a C 1 -C 12 alkoxy, a fluoride, a chloride, a bromide, or an iodide; or
t) R 4D is benzofuranyl, dibenzofuranyl, indolyl, indolinyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, isoxazolidinonyl, thiazolyl, benzothiazolyl, quinolinyl, rhodaninyl, thiolactonyl, triazinyl, or indonyl;
u) either: 1) DY 2 in combination is fluoride, chloride, bromide, or iodide; or
2) D is NR or O, and Y 2 is selected from R 1 ,
wherein Z 3 is selected independently from CR 4 or N, and Z 4 is selected independently from CR 1 2 , NR 1 , O, or S, with the provisos that two O or S atoms are not located adjacent to each other and no more than two Z 4 moieties are NR 1 ; and
with the further proviso that the compound excludes
N-Cycloheptyl-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine;
N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine;
[4-(4-Benzyl-piperazin-1-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-(4-methoxy-phenyl)-amine;
N-Cycloheptyl-6-morpholin-4-yl-N′-naphthalen-2-yl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-6-morpholin-4-yl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-6-morpholin-4-yl-N′-phenyl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-N′-(4-methoxy-phenyl)-6-morpholin-4-yl-[1,3,5]triazine-2,4-diamine;
N-Benzyl-N′-cycloheptyl-N″-(4-methoxy-phenyl)-N-methyl-[1,3,5]triazine-2,4,6-triamine;
N-(2-[1,3]Dioxolan-2-yl-ethyl)-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine; and
N-Cyclopropyl-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine.
10 . A compound according to claim 9 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 H, m-SO 2 F, m-SO 2 Cl, m-SO 2 Br, m-SO 2 I, m-SO 2 R 1B , m-SO 2 R 1C , m-SO 2 R 1D , m-S 2 OR 1 , m-NHC(O)R 1A , m-NHC(O)R 1B2 , m-NHC(O)R 1C , m-NHC(O)R 1D , or o-F, or X 1 and X 2 together is a fused phenyl, pyridine, or dioxane ring;
b) X 2 is selected from H, o-F, o-Cl, o-Br, o-I, o-CF 3 , o-R 1B , o-R 1C , o-R 1D , p-OR 1 , p-SR 1 , p-NR 1 R 1E , p-F, p-Cl, p-Br, p-CF 3 , p-CN, p-C(O)OH, p-C(O)OR 1B2 , p-C(O)OR 1C , p-C(O)OR 1D , p-NHC(O)R 1A , p-NHC(O)R 1B2 , p-NHC(O)R 1C , p-NHC(O)R 1D , p-(4-morpholinyl), p-(4-methyl-1-piperazinyl), or p-OM or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
11 . A compound according to claim 9 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) A is NR 1 ;
b) Y 1 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
wherein n is 1 or 2;
wherein x is 3, 4, or 5;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
c) D is NR 1 ;
d) Y 2 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
and
e) R 1A , in each occurrence, is selected independently from a linear or a branched alkyl having up to 10 carbon atoms.
12 . A compound according to claim 9 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 H, m-SO 2 F, m-SO 2 Cl, m-SO 2 Br, m-SO 2 I, m-SO 2 R 1B , m-SO 2 R 1C , m-SO 2 R 1D , m-S 2 OR 1 , m-NHC(O)R 1A , m-NHC(O)R 1B2 , m-NHC(O)R 1C , m-NHC(O)R 1D , or o-F, or X 1 and X 2 together is a fused phenyl, pyridine, or dioxane ring;
b) X 2 is selected from H, o-F, o-Cl, o-Br, o-I, o-CF 3 , o-R 1B , o-R 1C , o-R 1D , p-OR 1 , p-SR 1 , p-NR 1 R 1E ,p-F, p-Cl, p-Br, p-CF 3 , p-CN, p-C(O)OH, p-C(O)OR 1B2 , p-C(O)OR 1C , p-C(O)OR 1D , p-NHC(O)R 1A , p-NHC(O)R 1B2 , p-NHC(O)R 1C , p-NHC(O)R 1D , p-(4-morpholinyl), p-(4-methyl-1-piperazinyl), or p-OM or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
c) A is NR 1 ;
d) Y 1 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
wherein n is 1 or 2;
wherein x is 3, 4, or 5;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
e) D is NR 1 ;
f) Y 2 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
and
g) R 1A , in each occurrence, is selected independently from a linear or a branched alkyl having up to 10 carbon atoms.
13 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 9 .
14 . The pharmaceutical composition as claimed in claim 13 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
15 . The pharmaceutical composition as claimed in claim 13 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
16 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 , in each occurrence, is selected independently from R 1A , R 1B , R 1C , or R 1D ;
b) R 1A is hydrogen, fluoride, chloride, bromide, iodide, or amino;
c) R 1B is selected from:
i) a substituted or an unsubstituted cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl; or
ii) a substituted alkyl having up to 12 carbon atoms, wherein any substituent is selected independently from: an acyl, a formyl, an acyl halide, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
d) R 1C a substituted or an unsubstituted naphthyl, tetrahydronaphthyl, anthracenyl, aryloxide, or arylthiolate, wherein the aryl group in any of the aryloxide or arylthiolate is selected from a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, or an anthracenyl;
wherein any substituent on R 1C , in each occurrence, is selected independently from: a C 1 -C 12 alkoxy, a fluoride, a chloride, a bromide, or an iodide; or
e) R 1D is benzofuranyl, dibenzofuranyl, indolinyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, isoxazolidinonyl, thiazolyl, benzothiazolyl, quinolinyl, rhodaninyl, thiolactonyl, triazinyl, indonyl, 2-(methoxymethyl)pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, 1,3-dioxolanyl, azepanyl, decahydroquinolinyl, azabicyclo[3.2.1]octyl, azabicyclo[2.2.2]octyl, or azabicyclo[2.2.1]octyl;
f) G is NR 1 or O;
g) E is CH or N;
h) z is 0, 1, or 2;
i) X 1 is selected from hydrogen, fluoride, chloride, bromide, iodide, R 1B1 , R 1C , R 1D , NR 1 3 + , CN, NO 2 , CO 2 H, CO 2 R 1B2 , CO 2 R 1C , CO 2 R 1D , CH═CR 1 2 , C≡CR 1 , C(O)H, C(O)F, C(O)Br, C(O)I, C(O)R 1B3 , C(O)R 1C , C(O)R 1D , SO 2 H, SO 2 F, SO 2 Cl, SO 2 Br, SO 2 I, SO 2 R 1B , SO 2 R 1C , SO 2 R 1D , SO 2 OR 1 , NHC(O)R 1A , NHC(O)R 1B2 , NHC(O)R 1C , or NHC(O)R 1D , or X 1 and X 2 together is a fused phenyl, tolyl, xylyl, pyridine, dioxane, pyrrole, pyrrolidine, furan, or thiophene ring;
j) R 1B1 is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B1 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
k) R 1B2 is a substituted or an unsubstituted cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B2 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
l) R 1B3 is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkylthio, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B3 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
m) X 2 is selected from hydrogen; fluoride; chloride; bromide; iodide; R 1B ; R 1C ; R 1D ; CX x H 3-x , wherein X is a halogen and x is 0, 1, 2, or 3; OR 1 ; SR 1 ; NR 1 R 1E ; CN; C(O)OH, C(O)OR 1B2 ; C(O)OR 1C ; C(O)OR 1D ; NHC(O)R 1A ; NHC(O)R 1B2 ; NHC(O)R 1C ; NHC(O)R 1D ; 4-morpholinyl; 4-methyl-1-piperazinyl; OR 2 , wherein R 2 is selected from CH 2 OCH 3 , CH 2 OCH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CH 2 SCH 3 , or C(O)R 1 ; SR 3 , wherein R 3 is selected from CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CH 2 OCH 2 CH(CH 3 ) 2 , CH 2 NHC(O)CH 3 , or SR 1 ; OM or SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
n) R 1E , in each occurrence, is selected independently from fluoride, chloride, bromide, iodide, amino, R 1B , R 1C , or R 1D ;
o) either: 1) AY 1 in combination is fluoride, chloride, bromide, or iodide; or
2) A is NR 1 or O, and Y 1 is selected from:
a. R 1 , CR 4 3 , NR 4 2 , OR 4 , or SR 4 ; or
wherein n is an integer from 0 to 8 inclusive, m is an integer from 1 to 8 inclusive, Z 1 is independently selected from CR 1 or N, Z 2 is independently selected from CR 1 2 , NR 1 , O, or S, with the provisos that two O or S atoms are not located adjacent t to each other and no more than two Z 2 moieties are NR 1 ;
p) R 4 , in each occurrence, is selected independently from R 4A , R 4B , R 4C , or R 4D ;
q) R 4A is hydrogen, fluoride, chloride, bromide, iodide, or amino;
r) R 4B is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 10 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 4B , in each occurrence, is selected independently from: an amino, a C 1 -C 12 alkylthiolate, a fluoride, a chloride, a bromide, or an iodide;
s) R 4C a substituted or an unsubstituted naphthyl, tetrahydronaphthyl, anthracenyl, aryloxide, or arylthiolate, wherein the aryl group in any of the aryloxide or arylthiolate is selected from a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, or an anthracenyl;
wherein any substituent on R 4C , in each occurrence, is selected independently from: a C 1 -C 12 alkoxy, a fluoride, a chloride, a bromide, or an iodide; or
t) R 4D is benzofuranyl, dibenzofuranyl, indolinyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, isoxazolidinonyl, thiazolyl, benzothiazolyl, quinolinyl, rhodaninyl, thiolactonyl, triazinyl, or indonyl;
u) either: 1) DY 2 in combination is fluoride, chloride, bromide, or iodide; or
2) D is NR 1 or O, and Y 2 is selected from R 1 ,
wherein Z 3 is selected independently from CR 4 or N, and Z 4 is selected independently from CR 1 2 , NR 1 , O, or S, with the provisos that two O or S atoms are not located adjacent to each other and no more than two Z 4 moieties are NR 1 ; and
with the further proviso that the compound excludes
N-Cycloheptyl-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine;
N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine;
[4-(4-Benzyl-piperazin-1-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-(4-methoxy-phenyl)-amine;
N-Cycloheptyl-6-morpholin-4-yl-N′-naphthalen-2-yl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-6-morpholin-4-yl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-6-morpholin-4-yl-N′-phenyl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-N′-(4-methoxy-phenyl)-6-morpholin-4-yl-[1,3,5]triazine-2,4-diamine;
N-Benzyl-N′-cycloheptyl-N″-(4-methoxy-phenyl)-N-methyl-[1,3,5]triazine-2,4,6-triamine;
N-(2-[1,3]Dioxolan-2-yl-ethyl)-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine; and
N-Cyclopropyl-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine.
17 . A compound according to claim 16 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 H, m-SO 2 F, m-SO 2 Cl, m-SO 2 Br, m-SO 2 I, m-SO 2 R 1B , m-SO 2 R 1C , m-SO 2 R 1D , m-S 2 OR 1 , m-NHC(O)R 1A , m-NHC(O)R 1B2 , m-NHC(O)R 1C , m-NHC(O)R 1D , or o-F, or X 1 and X 2 together is a fused phenyl, pyridine, or dioxane ring;
b) X 2 is selected from H, o-F, o-Cl, o-Br, o-I, o-CF 3 , o-R 1B , o-R 1C , o-R 1D , p-OR 1 , p-SR 1 , p-NR 1 R 1E , p-F, p-Cl, p-Br, p-CF 3 , p-CN, p-C(O)OH, p-C(O)OR 1B2 , p-C(O)OR 1C , p-C(O)OR 1D , p-NHC(O)R 1A , p-NHC(O)R 1B2 , p-NHC(O)R 1C , p-NHC(O)R 1D , p-(4-morpholinyl), p-(4-methyl-1-piperazinyl), or p-OM or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
18 . A compound according to claim 16 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) A is NR 1 ;
b) Y 1 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
wherein n is 1 or 2;
wherein x is 3, 4, or 5;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
c) D is NR 1 ;
d) Y 2 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
and
e) R 1A , in each occurrence, is selected independently from a linear or a branched alkyl having up to 10 carbon atoms.
19 . A compound according to claim 16 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 H, m-SO 2 F, m-SO 2 Cl, m-SO 2 Br, m-SO 2 I, m-SO 2 R 1B , m-SO 2 R 1C , m-SO 2 R 1D , m-S 2 OR 1 , m-NHC(O)R 1A , m-NHC(O)R 1B2 , m-NHC(O)R 1C , m-NHC(O)R 1D , or o-F, or X 1 and X 2 together is a fused phenyl, pyridine, or dioxane ring;
b) X 2 is selected from H, o-F, o-Cl, o-Br, o-I, o-CF 3 , o-R 1B , o-R 1C , o-R 1D , p-OR 1 , p-SR 1 , p-NR 1 R 1E , p-F, p-Cl, p-Br, p-CF 3 , p-CN, p-C(O)OH, p-C(O)OR 1B2 , p-C(O)OR 1C , p-C(O)OR 1D , p-NHC(O)R 1A , p-NHC(O)R 1B2 , p-NHC(O)R 1C , p-NHC(O)R 1D , p-(4-morpholinyl), p-(4-methyl-1-piperazinyl), or p-OM or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
c) A is NR 1 ;
d) Y 1 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
wherein n is 1 or 2;
wherein x is 3, 4, or 5;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from I to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from I to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
e) D is NR 1 ;
f) Y 2 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl,
and
g) R 1A , in each occurrence, is selected independently from a linear or a branched alkyl having up to 10 carbon atoms.
20 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 16 .
21 . The pharmaceutical composition as claimed in claim 20 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
22 . The pharmaceutical composition as claimed in claim 20 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
23 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 , in each occurrence, is selected independently from R 1A , R 1B , R 1C , or R 1D .
b) R 1A is hydrogen, fluoride, chloride, bromide, iodide, or amino;
c) R 1B is selected from:
i) a substituted or an unsubstituted cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl; or
ii) a substituted alkyl having up to 12 carbon atoms, wherein any substituent is selected independently from: an acyl, a formyl, an acyl halide, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
d) R 1C a substituted or an unsubstituted naphthyl, tetrahydronaphthyl, anthracenyl, aryloxide, or arylthiolate, wherein the aryl group in any of the aryloxide or arylthiolate is selected from a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, or an anthracenyl;
wherein any substituent on R 1C , in each occurrence, is selected independently from: a C 1 -C 12 alkoxy, a fluoride, a chloride, a bromide, or an iodide; or
e) R 1D is benzofuranyl, dibenzofuranyl, indolinyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, isoxazolidinonyl, thiazolyl, benzothiazolyl, quinolinyl, rhodaninyl, thiolactonyl, triazinyl, indonyl, 2-(methoxymethyl)pyrrolidinyl, N—(C,-C 12 alkyl)pyrrolidinyl, 1,3-dioxolanyl, azepanyl, decahydroquinolinyl, azabicyclo[3.2.1]octyl, azabicyclo[2.2.2]octyl, or azabicyclo[2.2.1]octyl;
f) G is NR 1 or O;
g) E is CH or N;
h) z is 0, 1, or 2;
i) X 1 is selected from hydrogen, fluoride, chloride, bromide, iodide, R 1B1 , R 1C , R 1D , NR 1 3 + , CN, NO 2 , CO 2 H, CO 2 R 1B2 , CO 2 R 1C , CO 2 R 1D , CH═CR 1 2 , C≡CR 1 , C(O)H, C(O)F, C(O)Br, C(O)I, C(O)R 1B3 , C(O)R 1C , C(O)R 1D , SO 2 H, SO 2 F, SO 2 Cl, SO 2 Br, SO 2 I, SO 2 R 1B , SO 2 R 1C , SO 2 R 1D , SO 2 OR 1 , NHC(O)R 1A , NHC(O)R 1B2 , NHC(O)R 1C , or NHC(O)R 1D , or X 1 and X 2 together is a fused phenyl, tolyl, xylyl, pyridine, dioxane, pyrrole, pyrrolidine, furan, or thiophene ring;
j) R 1B1 is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B1 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
k) R 1B2 is a substituted or an unsubstituted cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B2 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
l) R 1B3 is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkylthio, each of which having up to 12 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 1B3 , in each occurrence, is selected independently from: a C 1 -C 12 alkyl, an acyl, a formyl, an acyl halide, a hydroxyl, an amino, a di(C 1 -C 12 alkyl)amino, a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, an anthracenyl, a C 3 -C 10 cycloalkyl, a fluoride, a chloride, a bromide, an iodide, a cyano, a C 1 -C 12 alkoxy, a nitro, a C 2 -C 12 alkenyl, a C 2 -C 12 alkynyl, a furanyl, a pyrrolidinyl, an N—(C 1 -C 12 alkyl)pyrrolidinyl, a piperidinyl, an imidazolyl, a pyrazolyl, a dioxolanyl, or a pyridinyl;
m) X 2 is selected from hydrogen; fluoride; chloride; bromide; iodide; R 1B ; R 1C ; R 1D ; CX x H 3-x , wherein X is a halogen and x is 0, 1, 2, or 3; OR 1 ; SR 1 ; NR 1 R 1E ; CN; C(O)OH, C(O)OR 1B2 ; C(O)OR 1C ; C(O)OR 1D ; NHC(O)R 1A ; NHC(O)R 1B2 ; NHC(O)R 1C ; NHC(O)R 1D ; 4-morpholinyl; 4-methyl-1-piperazinyl; OR 2 , wherein R 2 is selected from CH 2 OCH 3 , CH 2 OCH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CH 2 SCH 3 , or C(O)R 1 ; SR 3 , wherein R 3 is selected from CH 2 OCH 3 , CH 2 OCH 2 CH 2 OCH 3 , CH 2 OCH 2 CH(CH 3 ) 2 , CH 2 NHC(O)CH 3 , or SR 1 ; OM or SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
n) R 1E , in each occurrence, is selected independently from fluoride, chloride, bromide, iodide, amino, R 1B , R 1C , or R 1D ;
o) either: 1) AY 1 in combination is fluoride, chloride, bromide, or iodide; or
2) A is NR 1 or O, and Y 1 is selected from:
a. R 1 , CR 4 3 , NR 4 2 , OR 4 , or SR 4 ; or
wherein n is an integer from 0 to 8 inclusive, m is an integer from 1 to 8 inclusive, Z, is independently selected from CR 1 or N, Z 2 is independently selected from CR 1 2 , NR 1 , O, or S, with the provisos that two O or S atoms are not located adjacent t to each other and no more than two Z 2 moieties are NR 1 ;
p) R 4 , in each occurrence, is selected independently from R 4A , R 4B , R 4C , or R 4D ;
q) R 4A is hydrogen, fluoride, chloride, bromide, iodide, or amino;
r) R 4B is a substituted or an unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkadienyl, alkynyl, aralkyl, aralkenyl, aralkynyl, alkoxy, alkylthio, alkylamino, or dialkylamino, each of which having up to 10 carbon atoms and including linear or branched analogs thereof;
wherein any substituent on R 4B , in each occurrence, is selected independently from: an amino, a di(C 1 -C 12 alkyl)amino, a C 1 -C 12 alkoxy, a C 1 -C 12 alkylthiolate, a fluoride, a chloride, a bromide, or an iodide;
s) R 4C a substituted or an unsubstituted naphthyl, tetrahydronaphthyl, anthracenyl, aryloxide, or arylthiolate, wherein the aryl group in any of the aryloxide or arylthiolate is selected from a phenyl, a tolyl, a xylyl, a naphthyl, a tetrahydronaphthyl, or an anthracenyl;
wherein any substituent on R 4C , in each occurrence, is selected independently from: a C 1 -C 12 alkoxy, a fluoride, a chloride, a bromide, or an iodide; or
t) R 4D is furanyl, benzofuranyl, dibenzofuranyl, indolyl, thienyl, pyrrolyl, indolinyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, isoxazolidinonyl, thiazolyl, benzothiazolyl, pyridinyl, quinolinyl, rhodaninyl, thiolactonyl, triazinyl, or indonyl;
wherein Z 3 is selected independently from CR 4 or N, and Z 4 is selected independently from CR 1 2 , NR 1 , O, or S, with the provisos that two O or S atoms are not located adjacent to each other and no more than two Z 4 moieties are NR 1 ; and
with the further proviso that the compound excludes
N-Cycloheptyl-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine;
N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-N″-methyl-N″-(1-methyl-piperidin-4-yl)-[1,3,5]triazine-2,4,6-triamine;
[4-(4-Benzyl-piperazin-1-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-(4-methoxy-phenyl)-amine;
N-Cycloheptyl-6-morpholin-4-yl-N′-naphthalen-2-yl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-N′-(3-fluoro-4-methoxy-phenyl)-6-morpholin-4-yl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-6-morpholin-4-yl-N′-phenyl-[1,3,5]triazine-2,4-diamine;
N-Cycloheptyl-N′-(4-methoxy-phenyl)-6-morpholin-4-yl-[1,3,5]triazine-2,4-diamine;
N-Benzyl-N′-cycloheptyl-N″-(4-methoxy-phenyl)-N-methyl-[1,3,5]triazine-2,4,6-triamine;
N-(2-[1,3]Dioxolan-2-yl-ethyl)-N′-methyl-N′-(I -methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine; and
N-Cyclopropyl-N′-methyl-N′-(1-methyl-piperidin-4-yl)-N″-naphthalen-2-yl-[1,3,5]triazine-2,4,6-triamine.
24 . A compound according to claim 23 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 H, m-SO 2 F, m-SO 2 Cl, m-SO 2 Br, m-SO 2 I, m-SO 2 R 1B , m-SO 2 R 1C , m-SO 2 R 1D , m-S 2 OR 1 , m-NHC(O)R 1A , m-NHC(O)R 1B2 , m-NHC(O)R 1C , m-NHC(O)R 1D , or o-F, or X 1 and X 2 together is a fused phenyl, pyridine, or dioxane ring;
b) X 2 is selected from H, o-F, o-Cl, o-Br, o-I, o-CF 3 , o-R 1B , o-R 1C , o-R 1D , p-OR 1 , p-SR 1 , p-NR 1 R 1E , p-F, p-Cl, p-Br, p-CF 3 , p-CN, p-C(O)OH, p-C(O)OR 1B2 , p-C(O)OR 1C , p-C(O)OR 1D , p-NHC(O)R 1A , p-NHC(O)R 1B2 , p-NHC(O)R 1C , p-NHC(O)R 1D , p-(4-morpholinyl), p-(4-methyl-1-piperazinyl), or p-OM or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
25 . A compound according to claim 23 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) A is NR 1 ;
b) Y 1 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
wherein n is 1 or 2;
wherein x is 3, 4, or 5;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
c) D is NR 1 ;
d) Y 2 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
(CHR 1A ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
and
e) R 1A , in each occurrence, is selected independently from a linear or a branched alkyl having up to 10 carbon atoms.
26 . A compound according to claim 23 having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 H, m-SO 2 F, m-SO 2 Cl, m-SO 2 Br, m-SO 2 I, m-SO 2 R 1B , m-SO 2 R 1C , m-SO 2 R 1D , m-S 2 OR 1 , m-NHC(O)R 1A , m-NHC(O)R 1B2 , m-NHC(O)R 1C , m-NHC(O)R 1D , or o-F, or X 1 and X 2 together is a fused phenyl, pyridine, or dioxane ring;
b) X 2 is selected from H, o-F, o-Cl, o-Br, o-I, o-CF 3 , o-R 1B , o-R 1C , o-R 1D , p-OR 1 , p-SR 1 , p-NR 1 R 1E , p-F, p-Cl, p-Br, p-CF 3 , p-CN, p-C(O)OH, p-C(O)OR 1B2 , p-C(O)OR 1C , p-C(O)OR 1D , p-NHC(O)R 1A , p-NHC(O)R 1B2 , p-NHC(O)R 1C , p-NHC(O)R 1D , p-(4-morpholinyl), p-(4-methyl-1-piperazinyl), or p-OM or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
c) A is NR 1 ;
d) Y is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
wherein n is 1 or 2;
wherein x is 3, 4, or 5;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
e) D is NR 1 ;
f) Y 2 is selected from: a linear or a branched alkyl having up to 10 carbon atoms; a cycloalkyl having up to 10 carbon atoms; CH 2 CF 3 ;
(CHR 1 ) x NR 1A 2 , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x OR 1A , wherein x is an integer from 1 to 6, inclusive; (CHR 1A ) x Z 1 wherein x is an integer from 1 to 6, inclusive and Z 1 is selected from
pyrrolidinyl, piperidinyl, or
and
g) R 1A , in each occurrence, is selected independently from a linear or a branched alkyl having up to 10 carbon atoms.
27 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 23 .
28 . The pharmaceutical composition as claimed in claim 27 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
29 . The pharmaceutical composition as claimed in claim 27 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
30 . A compound having the formula
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 , in each occurrence, is selected independently from H, a linear or a branched alkyl with up to 10 carbon atoms, or a cycloalkyl with up to 10 carbon atoms;
b) X 1 is selected from m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 R 1 , or m-SO 2 OR 1 , or X 1 and X 2 together is a fused benzene, pyridine, or dioxane ring;
c) X 2 is selected from p-OR 1 , p-SR 1 , p-NR 1 R 1Q , p-OM, or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
wherein R 1Q is a linear or a branched alkyl with up to 10 carbon atoms or a cycloalkyl with up to 10 carbon atoms;
d) Y 1 is selected from cycloalkyl with up to 10 carbon atoms; linear or branched alkyl with up to 10 carbon atoms; CH 2 R 2 , wherein R 2 is a cycloalkyl with up to 10 carbon atoms; or
wherein n is 1 or 2; and
e) DY 2 in combination is selected from F, Cl, Br, I, or OR 1 , or
D is NR 1 and Y 2 is selected from R 1
31 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 30 .
32 . The pharmaceutical composition as claimed in claim 31 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
33 . The pharmaceutical composition as claimed in claim 31 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
34 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 , in each occurrence, is selected independently from H, a linear or a branched alkyl with up to 10 carbon atoms, or a cycloalkyl with up to 10 carbon atoms;
b) E is CH or N;
c) n is 0, 1, or 2;
d) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 R 1 , or m-SO 2 OR 1 , or X 1 and X 2 together is a fused benzene or pyridine ring;
e) X 2 is selected from H, o-Cl, o-Br, p-OR 1 , p-SR 1 , p-NR 1 R 1Q , p-F, p-Cl, p-Br, p-CF 3 , p-C(O)OR 1 , p-OM, or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
wherein R 1Q is a linear or a branched alkyl with up to 10 carbon atoms or a cycloalkyl with up to 10 carbon atoms;
f) A is NR 1 and Y 1 is selected from a cycloalkyl with up to 10 carbon atoms or a linear or a branched alkyl with up to 10 carbon atoms; or
AY 1 in combination is selected from F, Cl, Br, I,
and
g) DY 2 in combination is F, Cl, Br, I; or
D is NR 1 and Y 2 is selected from
or (CHR 1 ) x NR 1 2 , wherein x is an integer from 1 to 6, inclusive.
35 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 34 .
36 . The pharmaceutical composition as claimed in claim 35 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
37 . The pharmaceutical composition as claimed in claim 35 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
38 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 , in each occurrence, is selected independently from H, a linear or a branched alkyl with up to 10 carbon atoms, or a cycloalkyl with up to 10 carbon atoms;
b) E is CH or N;
c) n is 0, 1, or 2;
d) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 R 1 , or m-SO 2 OR 1 , or X 1 and X 2 together is a fused benzene or pyridine ring;
e) X 2 is selected from H, o-Cl, o-Br, p-OR 1 , p-SR 1 , p-NR 1 R 1Q , p-F, p-Cl, p-Br, p-CF 3 , p-C(O)OR 1 , p-OM, or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
wherein R 1Q is a linear or a branched alkyl with up to 10 carbon atoms or a cycloalkyl with up to 10 carbon atoms;
f) AY 1 in combination is selected from F, Cl, Br, I,
A is selected from NR 1 and Y 1 is selected from a cycloalkyl with up to 10 carbon atoms, a linear or a branched alkyl with up to 10 carbon atoms; or
A is selected from O and Y 1 is selected from R 1 or CH 2 R 1 ; and
g) DY 2 is a halogen, or D is NR 1 and Y 2 is selected from
39 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 38 .
40 . The pharmaceutical composition as claimed in claim 39 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
41 . The pharmaceutical composition as claimed in claim 39 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
42 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 , in each occurrence, is selected independently from H, a linear or a branched alkyl with up to 10 carbon atoms, or a cycloalkyl with up to 10 carbon atoms; or (CH 2 ) x CN, wherein x is an integer from 0 to 6, inclusive;
b) E is CH or N;
c) n is 0, 1, or 2;
d) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 R 1 , m-SO 2 OR 1 , m-NHC(O)R 1 , or o-F, or X 1 and X 2 together is a fused benzene, pyridine, or dioxane ring;
e) X 2 is selected from H, o-Cl, o-Br, o-CF 3 , o-R 1 , p-OR 1 , p-SR 1 , p-NR 1 R 1Q , p-F, p-Cl, p-Br, p-CF 3 , p-CN, p-C(O)OR 1 , p-NHC(O)R 1 , p-(4-morpholinyl), or p-(4-methyl-1-piperazinyl);
wherein R 1Q is a linear or a branched alkyl with up to 10 carbon atoms or a cycloalkyl with up to 10 carbon atoms;
f) AY 1 in combination is F, Cl, Br, I, or
wherein x is 3, 4, or 5;
A is NR 1 and Y 1 is selected from a cycloalkyl with up to 10 carbon atoms; a cycloalkyl with up to 10 carbon atoms substituted with R 1 ; a linear or a branched alkyl with up to 10 carbon atoms; CH 2 R 1 ; (CHR 1 ) y OR 1 , wherein y is an integer from 1 to 6, inclusive; or
or
A is O and Y 1 is selected from (CHR 1 ) y OR 1 , wherein y is an integer from 1 to 6, inclusive, or
and
g) DY 2 in combination is F; Br; I; or
wherein Z 2 is selected from R 1 , C(O)R 1 , C(O)OR 1 , pyridinyl, phenyl, tolyl, xylyl,
wherein q is an integer from 0 to 6, inclusive; or
D is NR 1 and Y 2 is selected from
a cycloalkyl with up to 10 carbon atoms; a cycloalkyl with up to 10 carbon atoms substituted with R 1 ; a linear or a branched alkyl with up to 10 carbon atoms; CH 2 R 1 ;
wherein x is 3, 4, or 5;
CH 2 CF 3 ; (CHR 1 ) z NR 1 2 , wherein z is an integer from 1 to 6, inclusive;
wherein x is 3, 4, or 5;
43 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 42 .
44 . The pharmaceutical composition as claimed in claim 43 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
45 . The pharmaceutical composition as claimed in claim 43 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
46 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 , in each occurrence, is selected independently from H, a linear or a branched alkyl with up to 10 carbon atoms, or a cycloalkyl with up to 10 carbon atoms; or (CH 2 ) x CN, wherein x is an integer from 0 to 6, inclusive;
b) E is CH or N;
c) n is 0, 1, or 2;
d) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 R 1 , m-SO 2 OR 1 , m-NHC(O)R 1 , or o-F, or X 1 and X 2 together is a fused benzene, pyridine, or dioxane ring;
e) X 2 is selected from H, o-Cl, o-Br, o-CF 3 , o-R 1 , p-OR 1 , p-SR 1 , p-NR 1 R 1Q , p-F, p-Cl, p-Br, p-CF 3 , p-CN, p-C(O)OR 1 , p-NHC(O)R 1 , p-(4-morpholinyl), or p-(4-methyl-1-piperazinyl);
wherein R 1Q is a linear or a branched alkyl with up to 10 carbon atoms or a cycloalkyl with up to 10 carbon atoms;
f) AY 1 in combination is F; Cl; Br; I; or
wherein x is 3, 4, or 5; or
A is NR 1 or O and Y 1 is selected from a cycloalkyl with up to 10 carbon atoms; a cycloalkyl with up to 10 carbon atoms substituted with R 1 ; a linear or a branched alkyl with up to 10 carbon atoms; CH 2 R 1 ; (CHR 1 ) y OR 1 , wherein y is an integer from 1 to 6, inclusive; or
and
g) DY 2 in combination is F; Br; I; or
wherein Z 2 is selected from R 1 , C(O)R 1 , C(O)OR 1 , pyridinyl, phenyl, tolyl, xylyl,
wherein q is an integer from 0 to 6, inclusive; or
D is NR 1 and Y 2 is selected from
a cycloalkyl with up to 10 carbon atoms; a cycloalkyl with up to 10 carbon atoms substituted with R 1 ; a linear or a branched alkyl with up to 10 carbon atoms; CH 2 R 1 ;
wherein x is 3, 4, or 5;
CH 2 CF 3 ; (CHR 1 ) z NHR 1 , wherein z is an integer from 1 to 6, inclusive;
47 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 46 .
48 . The pharmaceutical composition as claimed in claim 47 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
49 . The pharmaceutical composition as claimed in claim 47 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
50 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 , in each occurrence, is selected independently from H, a linear or a branched alkyl with up to 10 carbon atoms, or a cycloalkyl with up to 10 carbon atoms;
b) X 1 is selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 R 1 , or m-SO 2 OR 1 ;
c) X 2 is selected from o-R 1 , p-OR 1 , p-SR 1 , p-NR 1 R 1Q , p-OM, or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
d) R 1Q is a linear or a branched alkyl with up to 10 carbon atoms or a cycloalkyl with up to 10 carbon atoms;
e) Y 1 is selected from cycloalkyl with up to 10 carbon atoms or
and
f) Y 2 is selected from a linear or a branched alkyl with up to 10 carbon atoms, a cycloalkyl with up to 10 carbon atoms, or
and R 2 is H; or
NY 2 R 2 in combination is selected from
wherein x is 3, 4, or 5;
wherein q is an integer from 0 to 6, inclusive; or
wherein Z 2 is R 1 or
51 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 50 .
52 . The pharmaceutical composition as claimed in claim 51 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
53 . The pharmaceutical composition as claimed in claim 51 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
54 . A compound having the formula
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) R 1 , in each occurrence, is selected independently from H, a linear or a branched alkyl with up to 10 carbon atoms, or a cycloalkyl with up to 10 carbon atoms;
b) X 1 is in each occurrence independently selected from H, m-F, m-Cl, m-Br, m-I, m-CN, m-NO 2 , m-SO 2 R 1 , or m-SO 2 OR 1 ;
c) X 2 is in each occurrence independently selected from o-CH 3 , p-OR 1 , p-SR 1 , p-NR 1 R 1Q , or p-OM or p-SM, wherein M is selected from Li, Na, K, 0.5 Mg, or 0.5 Ca;
wherein R 1Q is a linear or a branched alkyl with up to 10 carbon atoms or a cycloalkyl with up to 10 carbon atoms;
d) Y is selected from a cycloalkyl with up to 10 carbon atoms, or
wherein n is 1 or 2; and
e) Y 2 is selected from
55 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 54 .
56 . The pharmaceutical composition as claimed in claim 55 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
57 . The pharmaceutical composition as claimed in claim 55 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
58 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) G is NH;
b) E is CH;
c) z is 0;
d) X 1 is —H, p-Cl, m-F, p-trifluoromethoxy, p-Br, p-C(O)OEt, p-Ph, m-Cl, m-Br, p-dimethylamino, p-diethylamino, p-NC(O)Me, m-NC(O)Me, m-Me, p-Me, or X 1 and X 2 together is a fused phenyl, pyridine, dioxane;
e) X 2 is —H, m-Cl, p-F, p-Cl, m-C(O)OEt, o-F, o-Cl, o-Br, p-4-morpholinyl, p-4-methyl-1-piperazinyl, m-OMe, m-OEt, o-OH, m-SMe, o-Me, p-OMe, or p-OPh;
A is NH or O;
AY 1 in combination is
and
D is NH or NMe;
DY 2 in combination is
59 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 58 .
60 . The pharmaceutical composition as claimed in claim 59 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
61 . The pharmaceutical composition as claimed in claim 59 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
62 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) G is NH;
b) E is CH;
c) z is 0;
d) X 1 is —H, p-Cl, m-F, p-trifluoromethoxy, p-Br, p-C(O)OEt, p-Ph, m-Cl, m-Br, p-dimethylamino, p-diethylamino, p-NC(O)Me, m-NC(O)Me, m-Me, p-Me, or X 1 and X 2 together is a fused phenyl, pyridine, dioxane;
e) X 2 is —H, m-Cl, p-F, p-Cl, m-C(O)OEt, o-F, o-Cl, o-Br, p-4-morpholinyl, p-4-methyl-1-piperazinyl, m-OMe, m-OEt, o-OH, m-SMe, o-Me,p-OMe, or p-OPh;
A is NH or O;
AY 1 in combination is
D is NH or NMe;
DY in combination is
63 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 62 .
64 . The pharmaceutical composition as claimed in claim 63 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
65 . The pharmaceutical composition as claimed in claim 63 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
66 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) G is NH;
b) E is CH;
c) z is O;
d) X 1 is —H, p-Cl, m-F, p-trifluoromethoxy, p-Br, p-C(O)OEt, p-Ph, m-Cl, m-Br, p-dimethylamino, p-diethylamino, p-NC(O)Me, m-NC(O)Me, m-Me, p-Me, or X 1 and X 2 together is a fused phenyl, pyridine, dioxane;
e) X 2 is —H, m-Cl, p-F, p-Cl, m-C(O)OEt, o-F, o-Cl, o-Br, p-4-morpholinyl, p-4-methyl-1-piperazinyl, m-OMe, m-OEt, o-OH, m-SMe, o-Me,p-OMe, or p-OPh;
A is NH or O;
AY 1 in combination is
D is NH or NMe;
DY 2 in combination is
67 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 66 .
68 . The pharmaceutical composition as claimed in claim 67 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
69 . The pharmaceutical composition as claimed in claim 67 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
70 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) G is NH;
b) E is CH;
c) z is 0;
d) X 1 is -H, p-Cl, m-F, p-trifluoromethoxy, p-Br, p-C(O)OEt, p-Ph, m-Cl, m-Br, p-dimethylamino, p-diethylamino, p-NC(O)Me, m-NC(O)Me, m-Me, p-Me, or X 1 and X 2 together is a fused phenyl, pyridine, dioxane;
e) X 2 is -H, m-Cl, p-F, p-Cl, m-C(O)OEt, o-F, o-Cl, o-Br, p-4-morpholinyl, p-4-methyl-1-piperazinyl, m-OMe, m-OEt, o-OH, m-SMe, o-Me, p-OMe, or p-OPh;
A is NH or O;
AY 1 in combination is
D is NH or NMe;
DY2 in combination is chiral
71 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 70 .
72 . The pharmaceutical composition as claimed in claim 71 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
73 . The pharmaceutical composition as claimed in claim 71 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
74 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) G is NH;
b) E is CH;
c) z is 0;
d) X 1 is p-Ph, p-dimethylamino, p-diethylamino, p-NHC(O)Me, m-NHC(O)Me, or X 1 and X 2 together is a fused phenyl, pyridine, dioxane;
e) X 2 is —H, m-Cl, p-F, p-Cl, m-C(O)OEt, o-F, o-Cl, o-Br, p-4-morpholinyl, p-4-methyl-1-piperazinyl, m-OMe, m-OEt, o-OH, m-SMe, o-Me, p-OMe, or p-OPh;
A is NH or O;
AY 1 in combination is
D is NH or NMe;
DY 2 in combination is
75 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 74 .
76 . The pharmaceutical composition as claimed in claim 75 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
77 . The pharmaceutical composition as claimed in claim 75 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
78 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) G is NH;
b) E is CH;
c) z is 0;
d) X 1 is -H, p-Cl, m-F, p-trifluoromethoxy, p-Br, p-C(O)OEt, p-Ph, m-Cl, m-Br, p-dimethylamino, p-diethylamino, p-NC(O)Me, m-NC(O)Me, m-Me, p-Me, or X 1 and X 2 together is a fused phenyl, pyridine, dioxane;
e) X 2 is p-4-morpholinyl, p-4-methyl-1-piperazinyl, m-SMe, or p-OPh;
A is NH or O;
AY 1 in combination is
D is NH or NMe;
DY 2 in combination is
79 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 78 .
80 . The pharmaceutical composition as claimed in claim 79 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
81 . The pharmaceutical composition as claimed in claim 79 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
82 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) G is NH;
b) E is CH;
c) z is 0;
d) X 1 is p-Ph, p-dimethylamino, p-diethylamino, p-NHC(O)Me, m-NHC(O)Me, or X 1 and X 2 together is a fused phenyl, pyridine, dioxane;
e) X 2 is -H, m-Cl, p-F, p-Cl, m-C(O)OEt, o-F, o-Cl, o-Br, p-4-morpholinyl, p-4-methyl-1-piperazinyl, m-OMe, m-OEt, o-OH, m-SMe, o-Me, p-OMe, or p-OPh;
A is NH or O;
AY 1 in combination is
D is NH or NMe;
DY 2 in combination is
83 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 82 .
84 . The pharmaceutical composition as claimed in claim 83 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
85 . The pharmaceutical composition as claimed in claim 83 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.
86 . A compound having the formula:
or a stereoisomer, an enantiomer, a diastereomer, a racemic mixture, a salt, or any combination thereof, wherein:
a) G is NH;
b) E is CH;
c) z is 0;
d) X 1 is -H, p-Cl, m-F, p-trifluoromethoxy, p-Br, p-C(O)OEt, p-Ph, m-Cl, m-Br, p-dimethylamino, p-diethylamino, p-NC(O)Me, m-NC(O)Me, m-Me, p-Me, or X 1 and X 2 together is a fused phenyl, pyridine, dioxane;
e) X 2 is p-4-morpholinyl, p-4-methyl-1-piperazinyl, m-SMe, or p-OPh;
A is NH or O;
AY 1 in combination is
D is NH or NMe;
DY 2 in combination is
87 . A pharmaceutical composition comprising a pharmaceutically acceptable carrier and at least one compound according to claim 86 .
88 . The pharmaceutical composition as claimed in claim 87 , further comprising at least one of the following:
a pharmaceutically acceptable auxiliary; a pharmaceutically acceptable preservative; a pharmaceutically acceptable excipient; or any combination thereof.
89 . The pharmaceutical composition as claimed in claim 87 , wherein the pharmaceutical composition is in the form of a tablet, a capsule, a cachet, a powder, a granule, a solution, a suspension, an emulsion, a bolus, a lozenge, a suppository, a pessary, a tampon, a cream, a gel, a paste, a foam, a spray, an aerosol, a microcapsule, a liposome, a transdermal patch, a pastille, a paste, or a mouthwash.Join the waitlist — get patent alerts
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