US2005075348A1PendingUtilityA1
Functionalized heterocycles as modulators of chemokine receptor function and methods of use therefor
Est. expiryMar 12, 2021(expired)· nominal 20-yr term from priority
Inventors:Geraldine C. HarrimanKenneth G. CarsonDaniel L. FlynnMichael SolomonYuntao SongBharat Kalidas TrivediBruce D. RothChristine KolzLy PhamKuai-Lin Sun
C07D 401/06C07D 405/12A61P 31/18C07D 401/12C07D 491/04C07D 401/14C07D 491/08C07D 401/04C07D 487/04C07D 403/12C07D 209/42C07D 235/26
49
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Claims
Abstract
Disclosed are novel compounds having the formula or a physiologically acceptable salt, amide, ester or prodrug thereof. The compounds can be used to modulate (antagonize, agonize) chemokine receptor function. Also disclosed is a method for treating a patient having an inflammatory disease and/or viral infection comprising administering an effective amount of a compound of Formula I. In particular embodiments, the invention is a method for treating a patient infected with HIV.
Claims
exact text as granted — not AI-modified1 . A compound having the formula
or a physiologically acceptable salt, amide, ester or prodrug thereof, wherein:
G is CR 1 or N;
J is CR 2 or N;
H is CR 3 or N;
M is C—Y, CH—Y, N—Y or N;
Q is NR 4 , SR 4 , O, SO or SO 2 ;
X is hydrogen, halogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, oxygen, NR 5 , S, SR 5 or NR 5 R 6 ;
Y is
P is -A-L-nitrogen-containing heteroaryl, -A-L-substituted nitrogen-containing heteroaryl,
wherein a, b and c are each, independently, an integer from 0 to about 4, with the proviso that when a is 0, c is not 1 and when b is 0, c is not 1;
A is O, N(—R 12 ), a bond or is absent;
L is C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, a bond, or
wherein
* is the point of attachment to A; and
** is the point of attachment to N;
R 1 , R 2 , R 3 , R 11 , R 13 , R 14 , R 15 , R 16 and R 19 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, halogen, C 1 -C 8 alkoxy,
Z is aryl, substituted aryl, heteroaryl or substituted heteroaryl; R 22 and R 23 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl; or R 22 and R 23 taken together with the atoms to which they are bonded can form a three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 12 , R 17 and R 18 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl,
R 20 and R 2 , are independently hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl or alkylheteroaryl; or R 20 and R 21 taken together with the atoms to which they are bonded can form a three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur; Z′ is aryl, substituted aryl, heteroaryl or substituted heteroaryl; or
R 1 taken together with any one of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 or R 16 and the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
R 2 taken together with any one of R 3 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 or R 16 and the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
P taken together with either R 1 or R 2 and the atoms to which they are bonded form a five to about eight membered substituted nonaromatic ring that can contain a heteroatom selected from the group consisting of oxygen, nitrogen and sulfur;
any two of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 , taken together with the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
with the proviso that the compound does not have the formula:
wherein R 7 and R 8 are independently hydrogen, methyl, ethyl or isopropyl; k is zero or one; and R 4 is hydrogen, methyl, ethyl, n-propyl, n-butyl, pentyl, phenyl or substituted phenyl.
2 . The compound of claim 1 , wherein X is phenyl, substituted phenyl, pyridyl, C 1 -C 8 alkyl or substituted C 1 -C 8 alky.
3 . The compound of claim 2 , wherein X is —CH 3 or —CF 3 .
4 . The compound of claim 2 , wherein X is phenyl of substituted phenyl.
5 . The compound of claim 4 , wherein X is phenyl.
6 . The compound of claim 1 , wherein R 4 is hydrogen.
7 . The compound of claim 1 , wherein R 1 and R 2 independently, hydrogen, a halogen, —CH 3 , —CF 3 or —OCH 3 .
8 . The compound of claim 1 , wherein Y is
9 . The compound of claim 8 , wherein R 17 is C 1 -C 8 alkyl, phenyl, substituted phenyl or pyridyl.
10 . The compound of claim 8 , wherein R 17 is phenyl.
11 . The compound of claim 1 , wherein Y is
wherein R 20 and R 21 are independently hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl; or
R 20 and R 21 taken together with the carbon atom to which they are bonded form a three to about eight membered ring which can contain one to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur; and
Z′ is selected from the group consisting of aryl, substituted aryl, heteroaryl and substituted heteroaryl.
12 . The compound of claim 11 , wherein Y is
13 . The compound of claim 1 , wherein Y is
14 . The compound of claim 13 , wherein R 17 is C 1 -C 8 alkyl, phenyl, substituted phenyl or pyridyl.
15 . The compound of claim 13 , wherein R 17 is phenyl.
16 . The compound of claim 1 , wherein L is
wherein
* is the point of attachment to A;
** is the point of attachment to N; and
A is a bond.
17 . The compound of claims 1 , wherein P is
R 7 and R 8 are ethyl; and
L is
18 . The compound of claim 1 , wherein P is
R 7 and R 8 are ethyl;
L is
and Y is
wherein R 20 and R 21 are independently hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, or
R 20 and R 21 taken together with the carbon atom to which they are bonded form a three to about eight membered ring which can contain one to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur; and
Z′ is selected from the group consisting of aryl, substituted aryl, heteroaryl and substituted heteroaryl.
19 . The compound of claim 1 , wherein P is
R 7 and R 8 taken together with the nitrogen atom to which they are bonded form a three to about eight membered cyclic ring which can contain one or two additional heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
L is
and Y is
wherein R 20 and R 21 are independently hydrogen, C 1 -C 8 alky, substituted C 1 -C 8 alkyl, or
R 20 and R 21 taken together with the carbon atom to which they are bonded form a three to about eight membered ring which can contain one to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur; and
Z′ is selected from the group consisting of aryl, substituted aryl, heteroaryl and substituted heteroaryl.
20 . The compound of claim 1 , wherein
X is methyl or trifluoromethyl; A is a bond; R 4 is hydrogen; and Y is
21 . The compound of claim 1 , wherein said compound has the formula
22 . The compound of claim 22 , wherein R 4 is hydrogen.
23 . The compound of claim 1 , wherein said compound has the formula
wherein
M is N—Y or CH—Y; and
X is oxygen, S or SR 5 .
24 . The compound of claim 23 , wherein X is oxygen.
25 . The compound of claim 23 , wherein R 4 is hydrogen.
26 . The compound of claim 1 , wherein said compound has the formula
wherein
M is C—Y or N; and
X is hydrogen, halogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, SR 5 or NR 5 R 6 .
27 . The compound of claim 26 , wherein X is phenyl.
28 . The compound of claim 26 , wherein R 4 is hydrogen.
29 . The compound of claim 1 , wherein said compound has the formula
30 . The compound of claim 29 , wherein X is O, S or NR 5 .
31 . The compound of claim 29 , wherein R 4 is hydrogen.
32 . The compound of claim 29 , wherein
X is oxygen, R 4 is hydrogen; and Y is R 20 and R 21 are independently hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, or R 20 and R 21 taken together with the carbon atom to which they are bonded form a three to about eight membered ring which can contain one to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur; and Z′ is selected from the group consisting of aryl, substituted aryl, heteroaryl and substituted heteroaryl.
33 . The compound of claim 1 , wherein said compound has the formula
34 . The compound of claim 33 , wherein R 4 is hydrogen.
35 . The compound of claim 33 , wherein X is phenyl, substituted phenyl, pyridyl, C 1 -C 8 alkyl, —CH 3 or —CF 3 .
36 . The compound of claim 1 , wherein said compound has a formula selected from
wherein
n is an integer from zero to about three;
m is zero or one;
W is CH 2 or C(═O); and
Q is CH 2 , NR 18 , O or S.
37 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
5-[2-(4-tert-Butoxycarbonyl-piperazin-1-yl)-ethoxy]-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 1-[2-(3-Benzyloxycarbonyl-2-methyl-1H-indole-5-yloxy)-ethyl]-piperazin-1-ium; chloride; 2-Methyl-5-[2-(4-methyl-piperazin-1-yl)-ethoxy]-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-[2-(3-methyl-pyrrolidin-1-yl)-ethoxy]-1H-indole-3-carboxylic acid benzyl ester; 1-[2-(3-Benzyloxycarbonyl-2-methyl-1H-indole-5-yloxy)-ethyl]-3-phenyl-pyrrolidinium; chloride; 5-(2-Diisopropylamino-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 1-Benzyl-5-(2-diethylamino-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 1-Methyl-5-(2-diethylamino-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-(1-Diethylcarbamoyl-propoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(4-pyrrolidin-1-yl-butoxy)-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(4-pyrrolidin-1-yl-butoxy)-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(2-piperidin-1-yl-ethoxy)-1H-indole-3-carboxylic acid benzyl ester; 5-(2-Diethylamino-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-(2-Diethylamino-ethyl)-2-phenyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-[2-(3,3,4,4-tetramethyl-pyrrolidin-1-yl)-ethoxy]-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-[2-(2-phenyl-pyrrolidin-1-yl)-ethoxy]-1H-indole-3-carboxylic acid benzyl ester;
5-[2-((R)-3-Hydroxymethyl-pyrrolidin-1-yl)-ethoxy]-2-methyl-1H-indole-3-carboxylic acid benzyl ester;
2-Methyl-5-[2-(2-pyridin-3-yl-pyrrolidin-1-yl)-ethoxy]-1H-indole-3-carboxylic acid benzyl ester; 5-(2-Dipropylamino-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-(2-Diethylamino-ethyl)-2-trifluoromethyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(2-pyrrolidine-1-yl-ethylamino)-1H-indole-3-carboxylic acid benzyl ester; 5-Amino-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-[Bis-(2-pyrrolidine-1-yl-ethyl)-amino)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-[Acetyl-(2-pyrrolidine-1-yl-ethyl)-amino)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(4-phenyl-piperazin-1-yl)-1H-indole-3-carboxylic acid benzyl ester;
38 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
5-[2-(4-Hydroxy-piperidine-1-yl)-ethoxy]-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-[2-(2-methyl-pyrrolidin-1-yl)-ethoxy]-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-[2-(2-oxa-6-aza-bicyclo[2.2.1]hept-6-yl)-ethoxy]-1H-indole-3-carboxylic acid benzyl ester; 5-{2-[3-(Acetyl-methyl-amino)-pyrrolidin-1-yl)-ethoxy}-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-[2-(2,5-Dimethyl-pyrrolidin-1-yl)-ethoxy]-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-[2-(3-Dimethylamino-pyrrolidin-1-yl)-ethoxy]-2-methyl-1H-indole-3-carboxylic acid benzyl ester, dihydrochloride; 2-Methyl-5-[2-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-ethoxy]-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-[2-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-ethyl]-1H-indole-3-carboxylic acid benzyl ester; 5-[2-((R)-2-Methoxymethyl-pyrrolidin-1-yl)-ethyl]-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-1H-indole-3-carboxylic acid benzyl ester; 5-[2-((R)-2-Hydroxymethyl-pyrrolidin-1-yl)-ethyl]-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-[2-((S)-2-Methoxymethyl-pyrrolidin-1-yl)-ethyl]-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-(2-Azetidin-1-yl-ethyl]-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-[2-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)-ethyl]-1H-indole-3-carboxylic acid benzyl ester; 5-{2-[3-(Acetyl-methyl-amino)-pyrrolidin-1-yl)-ethyl}-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-[2-(4-Hydroxy-piperidine-1-yl)-ethyl]-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(3-pyrrolidin-1-yl-propoxy)-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(1-methyl-piperidin-2-yl-methoxy)-1H-indole-3-carboxylic acid benzyl ester; 5-(1-Diethylcarbamoyl-1-methyl-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-7-pyrrolidin-1-yl-methyl-3,7,8,9-tetrahydro-pyrano[3,2-e]indole-1-carboxylic acid benzyl ester; 2-Methyl-5-(2-methyl-2-pyrrolidin-1-yl-propoxy)-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(1-methyl-piperidin-3-ylmethoxy)-1H-indole-3-carboxylic acid benzyl ester; 5-(1-Benzyl-pyrrolidin-3-yloxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-(1-Ethyl-pyrrolidin-3-yloxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(pyrrolidin-3-yloxy)-1H-indole-3-carboxylic acid benzyl ester, hydrochloride;
39 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
5-(1-Isopropyl-pyrrolidin-3-yloxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-Carbamimidoylmethoxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-(2-Imino-2-pyrrolidin-1-yl-ethoxy)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-pyridin-3-yl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-pyridin-3-yl-indole-1,3-dicarboxylic acid 3-benzyl ester 1-tert-butyl ester; 5-(3-Diethylamino-propyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-(3-Dimethylamino-prop-1-ynyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-((Z)-3-Dimethylamino-propenyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-(1-Ethyl-pyrrolidin-3-yl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(2-pyrrolidin-1-yl-ethyl)-1H-indole-3-carboxylic acid benzyl ester hydrochloride; 2-Methyl-5-(2-pyrrolidin-1-yl-ethyl)-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-[2-(4-methyl-piperazin-1-yl)-ethyl]-1H-indole-3-carboxylic acid benzyl ester; 5-[2-(Cyclohexyl-methyl-amino)-ethyl]-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(2-piperidin-1-yl-ethyl)-1H-indole-3-carboxylic acid benzyl ester; 5-(2-Diisobutylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(2-methylamino-ethyl)-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-{2-[methyl-(tetrahydro-pyran-4-yl)-amino]-ethyl}-1H-indole-3-carboxylic acid benzyl ester; 5-Aminomethyl-2-methyl-1H-indole-3-carboxylic acid benzyl ester, hydrochloride; 5-(tert-Butoxycarbonylamino-methyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-Diethylaminomethyl-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-phenyl-ethyl ester, hydrochloride; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-phenyl-ethyl ester; 5-(2-Dimethylamino-ethoxy)-2-methyl-1H-indole-3-carboxylic acid (S)-1-phenyl-ethyl ester; 2-Methyl-5-(2-morpholin-4-yl-ethoxy)-1H-indole-3-carboxylic acid 1-phenyl ethyl ester hydrochloride; 2-Methyl-5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-3-carboxylic acid-1-phenyl ethyl ester hydrochloride;
40 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
2-Methyl-5-(pyrrolidin-1-yl-ethoxy)-1H-indole-3-carboxylic acid benzyl ester; 2-Methyl-5-(1-methyl-2-pyrrolidin-1-yl-propoxy)-1H-indole-3-carboxylic acid benzyl ester; 5-(2-Cyclohexylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-(2-tert-Butoxycarbonylamino ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-bromophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-(2-methyl-2-propyl)phenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2-chlorophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2,6-dichlorophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 3,5-dichloro-benzyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-bromophenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(3-fluorophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(3-fluorophenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2-chlorophenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2,6-dichlorophenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(3-fluorophenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2-chlorophenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2,6-dichlorophenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-(S)-1-phenyl-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 3,5-dichloro-benzyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(3-fluorophenyl)-ethyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2-chlorophenyl)-ethyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2,6-dichlorophenyl)-ethyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 3,5-dichloro-benzyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-(S)-1-phenyl-ethyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(3-fluorophenyl)-ethyl ester;
41 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2-chlorophenyl)-ethyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2,6-dichlorophenyl)-ethyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid 3,5-dichloro-benzyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid-(S)-1-phenyl-ethyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 3-nitro-4-methyl-benzyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 3-nitro-4-methyl-benzyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 3-nitro-4-methyl-benzyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 3-nitro-4-methyl-benzyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-fluorophenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-fluorophenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-fluorophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 2-biphenyl methyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 2-biphenyl methyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 2-biphenyl methyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 2-biphenyl methyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(3-chlorophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2-trifluoromethyl-phenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2-bromophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2,4-dichlorophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-chlorophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 5,6,7,8-tetrahydronaphth-5-yl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid indan-1-yl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-methyl-1-cyclopentyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-methyl-1-cyclohexyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2-bromophenyl)-ethyl ester;
42 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-bromophenyl)-ethyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-(2-methyl-2-propyl)phenyl)-ethyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2,4-dichlorophenyl)-ethyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-chlorophenyl)-ethyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1,2,3,4-tetrahydronaphth-1-yl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic indan-1-yl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-methyl-1-cyclopentyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-methyl-1-cyclohexyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2-bromophenyl)-ethyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-bromophenyl)-ethyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-(2-methyl-2-propyl)phenyl)-ethyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(2,4-dichlorophenyl)-ethyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid-1-(4-chlorophenyl)-ethyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid (1,2,3,4-tetrahydronaphthyl-1-yl) ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid (1-indanyl) ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2-bromophenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(4-bromophenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(4-t-butylphenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-H-indole-3-carboxylic acid 1-(2,4-dichlorophenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(4-chlorophenyl)-ethyl ester; 5-(2-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (1,2,3,4-tetrahydronaphthyl-1-yl) ester; 5-(2-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (1-indanyl) ester; 5-(2-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (1-methylcyclopetan-1-yl) ester; 5-(2-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (1-methylcyclohex-1-yl) ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(4-bromophenyl)-ethyl ester;
43 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2-bromophenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(4-t-butylphenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,4-dichlorophenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(4-chlorophenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (1,2,3,4-tetrahydronaphthyl-1-yl) ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (1-indanyl) ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (1-methylcyclopetan-1-yl) ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (1-methylcyclohex-1-yl) ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(3-methoxyphenyl)-ethyl ester; 5-(2-Piperidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(3-methoxyphenyl)-ethyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(3-methoxyphenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(3-methoxyphenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(3-methoxyphenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,5-dimethylphenyl)-ethyl ester; 5-(2-Piperidinyl-ethyl)-2-methyl-1H-indole-3-carboxylic 1-(2,5-dimethylphenyl)-ethyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,5-dimethylphenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,5-dimethylphenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,5-dimethylphenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,4-dimethylphenyl)-ethyl ester; 5-(2-Piperidinyl-ethyl)-2-methyl-1H-indole-3-carboxylic 1-(2,4-dimethylphenyl)-ethyl ester; 5-(2-(4-Hydroxy-piperidino)-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,4-dimethylphenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,4-dimethylphenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,4-dimethylphenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(3,4-dichlorophenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(3,4-dichlorophenyl)-ethyl ester;
44 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
5-(2-Piperidinyl-ethyl)-2-methyl-1H-indole-3-carboxylic 1-(3,4-dichlorophenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(3,4-dichlorophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2-methylphenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2-methylphenyl)-ethyl ester; 5-(2-Piperidinyl-ethyl)-2-methyl-1H-indole-3-carboxylic 1-(2-methylphenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2-methylphenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,3,4,5-tetrafluorophenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,3,4,5-tetrafluorophenyl)-ethyl ester; 5-(2-Piperidinyl-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,3,4,5-tetrafluorophenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,3,4,5-tetrafluorophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,6-dimethylphenyl)-ethyl ester; 5-(2-Pyrrolidino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,6-dimethylphenyl)-ethyl ester; 5-(2-Piperidinyl-ethyl)-2-methyl-1H-indole-3-carboxylic 1-(2,6-dimethylphenyl)-ethyl ester; 5-(2-N-Cyclohexyl-N-methyl-amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(2,6-dimethylphenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid 1-(S)-(4-fluorophenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; and 2-Methyl-5-(2-pyrrolidin-1-yl-ethyl)-1H-indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester.
45 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
5-(2-Amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester hydrochloride; 5-(2-Diethylamino-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester hydrochloride; 2-Methyl-5-(2-pyrrolidin-1-yl-ethyl)-1H-indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; 2-Methyl-5-(2-piperidin-1-yl-ethyl)-1H-indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; 2-Methyl-5-(2-piperidin-1-yl-ethyl)-1H-indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; 5-[2-(4-Hydroxy-piperidin-1-yl)-ethyl]-2-methyl-1H-indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; 5-[2-(4-Hydroxy-piperidin-1-yl)-ethyl]-2-methyl-1H-indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; 5-[2-(Cyclohexyl-methyl-amino)-ethyl]-2-methyl-1H-indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; 5-[2-(Cyclohexyl-methyl-amino)-ethyl]-2-methyl-1H-indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; 5-(1-Ethyl-piperidin-4-yl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; 5-(1-Ethyl-piperidin-4-yl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; 5-[1-(1-Ethyl-piperidin-4-yl)-1-methyl-ethyl]-2-methyl-1H-indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; 5-[1-(1-Ethyl-piperidin-4-yl)-1-methyl-ethyl]-2-methyl-1H-indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; 5-(1-Ethyl-4-methyl-piperidin-4-yl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; 5-(1-Ethyl-4-methyl-piperidin-4-yl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; 5-(1-Isopropyl-pyrrolidin-3-yl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; 5-(1-Isopropyl-pyrrolidin-3-yl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; 5-(1-Ethyl-1-aza-spiro[4.4]non-7-yl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; 5-(1-Ethyl-1-aza-spiro[4.4]non-7-yl)-2-methyl-1H-indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; 2-Methyl-7-(2-propyl)-1H-azepino[5,6-h]indole-3-carboxylic acid benzyl ester; 7-Isopropyl-2-methyl-1,5,6,7,8,9-hexahydro-azepino[4,5-f]indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; and 7-Isopropyl-2-methyl-1,5,6,7,8,9-hexahydro-azepino[4,5-f]indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester.
46 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
6-(2-Diethylamino-ethyl)-2-oxo-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 2-Oxo-6-(2-pyrrolidin-1-yl-ethyl)-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 2-Oxo-6-(2-piperidin-1-yl-ethyl)-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 6-[2-(Cyclohexyl-methyl-amino)-ethyl]-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 6-{2-[4-(Furan-2-carbonyl)-piperazin-1-yl]-ethyl}-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; {4-[2-(3-Benzylcarbamoyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-ethyl]-piperazin-1-yl}-acetic acid ethyl ester; 6-{2-[4-(Isopropylcarbamoyl-methyl)-piperazin-1-yl]ethyl}-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 2-Oxo-6-{2-[4-(3-phenyl-alkyl)-piperazin-1-yl]-ethyl}-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 2-Oxo-6-[2-(4-pyridin-2-yl-piperazin-1-yl)-ethyl]-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 6-{2-[4-(4-Acetyl-phenyl)-piperazin-1-yl]-ethyl}-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 2-Oxo-6-[2-(4-phenethyl-piperazin-1-yl)-ethyl]-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 6-{2-[4-(2-Cyclohexyl-ethyl)-piperazin-1-yl]-ethyl}-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 6-[2-(4-Benzyl-piperidin-1-yl)-ethyl]-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 6-{2-[4-(2-Morpholin-4-yl-2-oxo-ethyl)-piperazin-1-yl]-ethyl}-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid phenethyl-amide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid isopropylamide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid (2,4-dimethoxy-phenyl)-amide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid propylamide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid (4-isopropyl-phenyl)-amide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid naphthalen-1-ylamide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid (4-fluoro-phenyl)-amide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid 2-chloro-benzylamide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid (4-chloro-phenyl)-amide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid 2-methyl-benzylamide;
47 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid 4-methoxy-benzylamide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid (3-chloro-phenyl)-amide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid (2-ethoxy-phenyl)-amide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid (4-benzyloxy-phenyl)-amide; 4-[2-(3-Benzylcarbamoyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester; 2-Oxo-6-(2-pyrrolidin-1-yl-ethyl)-2,3-dihydro-benzoimidazole-1-carboxylic acid (1-phenyl-ethyl)-amide; 6-(2-Diethylamino-ethyl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid (1S-phenyl-ethyl)-amide; 2-Oxo-6-{2-[4-(2-oxo-2,3-dihydro-benzoimidazole-1-yl)-piperidin-1-yl]-ethyl)-2,3-dihydro-benzoimidazole-1-carboxylic acid benzylamide; and 2-Oxo-6-(2-pyrrolidin-1-yl-ethyl)-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butylamide.
48 . The compound of claim 1 , wherein said compound is selected from the group consisting of:
2-Methyl-6-pyrrolidin-1-yl-5,6,7,8-tetrahydro-1H-benz[f]indole-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; 2-Methyl-6-pyrrolidin-1-yl-5,6,7,8-tetrahydro-1H-benz[f]indole-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; 6-Diethylamino-2-methyl-1,5,6,7-tetrahydro-1-aza-s-indacene-3-carboxylic acid (S)-1-(4-fluoro-phenyl)-ethyl ester; 6-Diethylamino-2-methyl-1,5,6,7-tetrahydro-1-aza-s-indacene-3-carboxylic acid (S)-1-pyridin-4-yl-ethyl ester; and 2-Methyl-6-pyrrolidino-5,6,7,8-tetrahydrobenzo[h]-1H-indole-3-carboxylic acid benzyl ester.
49 . A pharmaceutical composition comprising a compound of claim 1 and a physiologically acceptable vehicle, excipient, carrier or adjuvant.
50 . A method for modulating the activity of a chemokine receptor in a patient -comprising administering to a patient in need thereof an effective amount of a compound having the formula
or a physiologically acceptable salt, amide, ester or prodrug thereof, wherein:
G is CR 1 or N;
J is CR 2 or N;
H is CR 3 or N;
M is C—Y, CH—Y, N—Y or N;
Q is NR 4 , SR 4 , O, SO or SO 2 ;
X is hydrogen, halogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, oxygen, NR 5 , S, SR 5 or NR 5 R 6 ;
Y is
P is -A-L-nitrogen-containing heteroaryl, -A-L-substituted nitrogen-containing heteroaryl,
wherein a, b and c are each, independently, an integer from 0 to about 4, with the proviso that when a is 0, c is not 1 and when b is 0, c is not 1;
A is O, N(—R 12 ), a bond or is absent;
L is C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, a bond, or
wherein
* is the point of attachment to A; and
** is the point of attachment to N;
R 1 , R 2 , R 3 , R 11 , R 13 , R 14 , R 15 , R 16 and R 19 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, halogen, C 1 -C 8 alkoxy,
Z is aryl, substituted aryl, heteroaryl or substituted heteroaryl; R 22 and R 23 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl; or R 22 and R 23 taken together with the atoms to which they are bonded can form a three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 12 , R 17 and R 18 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl,
R 20 and R 21 are independently hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl or alkylheteroaryl; or R 20 and R 21 taken together with the atoms to which they are bonded can form a three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur; Z′ is aryl, substituted aryl, heteroaryl or substituted heteroaryl; or
R 1 taken together with any one of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 or R 16 and the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
R 2 taken together with any one of R 3 , R 7 , R 8 , R 19 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 or R 16 and the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
P taken together with either R 1 or R 2 and the atoms to which they are bonded form a five to about eight membered substituted nonaromatic ring that can contain a heteroatom selected from the group consisting of oxygen, nitrogen and sulfur; and
any two of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 , taken together with the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur.
51 . The method of claim 42 , wherein said chemokine receptor is CCR5.
52 . A method for treating a patient having an inflammatory disease comprising administering to said patient an effective amount of a compound having the formula
or a physiologically acceptable salt, amide, ester or prodrug thereof, wherein:
G is CR 1 or N;
J is CR 2 or N;
H is CR 3 or N;
M is C—Y, CH—Y, N—Y or N;
Q is NR 4 , SR 4 , O, SO or SO 2 ;
X is hydrogen, halogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, oxygen, NR 5 , S, SR 5 or NR 5 R 6 ;
Y is
P is -A-L-nitrogen-containing heteroaryl, -A-L-substituted nitrogen-containing heteroaryl,
wherein a, b and c are each, independently, an integer from 0 to about 4, with the proviso that when a is 0, c is not 1 and when b is 0, c is not 1;
A is O, N(—R 12 ), a bond or is absent;
L is C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, a bond, or
wherein
* is the point of attachment to A; and
** is the point of attachment to N;
R 1 , R 2 , R 3 , R 11 , R 13 , R 14 , R 15 , R 16 and R 19 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, halogen, C 1 -C 8 alkoxy,
Z is aryl, substituted aryl, heteroaryl or substituted heteroaryl; R 22 and R 23 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl; or R 22 and R 23 taken together with the atoms to which they are bonded can form a three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 12 , R 17 and R 18 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl,
R 20 and R 21 are independently hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl or alkylheteroaryl; or R 20 and R 21 taken together with the atoms to which they are bonded can form a three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur; Z′ is aryl, substituted aryl, heteroaryl or substituted heteroaryl; or
R 1 taken together with any one of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 or R 16 and the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
R 2 taken together with any one of R 3 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 or R 16 and the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
P taken together with either R 1 or R 2 and the atoms to which they are bonded form a five to about eight membered substituted nonaromatic ring that can contain a heteroatom selected from the group consisting of oxygen, nitrogen and sulfur; and
any two of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 , taken together with the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur.
53 . A method for treating a patient infected by HIV comprising administering to said patient an effective amount of a compound having the formula
or a physiologically acceptable salt, amide, ester or prodrug thereof, wherein:
G is CR 1 or N;
J is CR 2 or N;
H is CR 3 or N;
M is C—Y, CH—Y, N—Y or N;
Q is NR 4 , SR 4 , O, SO or SO 2 ;
X is hydrogen, halogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, oxygen, NR 5 , S, SR 5 or NR 5 R 6 ;
Y is
P is -A-L-nitrogen-containing heteroaryl, -A-L-substituted nitrogen-containing heteroaryl,
wherein a, b and c are each, independently, an integer from 0 to about 4, with the proviso that when a is 0, c is not 1 and when b is 0, c is not 1;
A is O, N(—R 12 ), a bond or is absent;
L is C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, a bond, or
wherein
* is the point of attachment to A; and
** is the point of attachment to N;
R 1 , R 2 , R 3 , R 11 , R 13 , R 14 , R 15 , R 16 and R 19 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, halogen, C 1 -C 8 alkoxy,
Z is aryl, substituted aryl, heteroaryl or substituted heteroaryl; R 22 and R 23 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl; or R 22 and R 23 taken together with the atoms to which they are bonded can form a three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 12 , R 17 and R 18 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl,
R 20 and R 21 are independently hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl or alkylheteroaryl; or R 20 and R 21 taken together with the atoms to which they are bonded can form a three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur; Z′ is aryl, substituted aryl, heteroaryl or substituted heteroaryl; or
R 1 taken together with any one of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 or R 16 and the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
R 2 taken together with any one of R 3 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 or R 16 and the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
P taken together with either R 1 or R 2 and the atoms to which they are bonded form a five to about eight membered substituted nonaromatic ring that can contain a heteroatom selected from the group consisting of oxygen, nitrogen and sulfur; and
any two of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 , taken together with the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur.
54 . A method for inhibiting progression to AIDS or ARC in a patient infected with HIV comprising administering to said patient an effective amount of a compound having the formula
or a physiologically acceptable salt, amide, ester or prodrug thereof, wherein:
G is CR 1 or N;
J is CR 2 or N;
H is CR 3 or N;
M is C—Y, CH—Y, N—Y or N;
Q is NR 4 , SR 4 , O, SO or SO 2 ;
X is hydrogen, halogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, oxygen, NR 5 , S, SR 5 or NR 5 R 6 ;
Y is
P is -A-L-nitrogen-containing heteroaryl, -A-L-substituted nitrogen-containing heteroaryl,
wherein a, b and c are each, independently, an integer from 0 to about 4, with the proviso that when a is 0, c is not 1 and when b is 0, c is not 1;
A is O, N(—R 12 ), a bond or is absent;
L is C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, a bond, or
wherein
* is the point of attachment to A; and
** is the point of attachment to N;
R 1 , R 2 , R 3 , R 11 , R 13 , R 14 , R 15 , R 16 and R 19 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl, halogen, C 1 -C 8 alkoxy,
Z is aryl, substituted aryl, heteroaryl or substituted heteroaryl; R 22 and R 23 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl; or R 22 and R 23 taken together with the atoms to which they are bonded can form a three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 12 , R 17 and R 18 are independently, hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl, alkylheteroaryl,
R 20 and R 2 , are independently hydrogen, C 1 -C 8 alkyl, substituted C 1 -C 8 alkyl, C 2 -C 8 alkenyl, substituted C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, substituted C 2 -C 8 alkynyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylalkyl, alkylaryl, heteroarylalkyl or alkylheteroaryl; or R 20 and R 21 taken together with the atoms to which they are bonded can form a three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur; Z′ is aryl, substituted aryl, heteroaryl or substituted heteroaryl; or
R 1 taken together with any one of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 or R 16 and the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
R 2 taken together with any one of R 3 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 or R 16 and the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
P taken together with either R 1 or R 2 and the atoms to which they are bonded form a five to about eight membered substituted nonaromatic ring that can contain a heteroatom selected from the group consisting of oxygen, nitrogen and sulfur; and
any two of R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 , taken together with the atoms to which they are bonded form a substituted or unsubstituted three to about eight membered cyclic ring which can contain zero to about three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur.Join the waitlist — get patent alerts
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