US 7,612,211 B2Granted

Benzimidazole TRPV1 inhibitors

AssigneeJanssen Pharmaceutica NV

InventorsWing S. Cheung, Daniel J. Parks, William H. Parsons, Sharmila Patel, Mark R. Player

Life of this patent

Estimating the term…

Abstract

The invention is directed to compounds of Formula (I): to pharmaceutical compositions containing such compounds and to methods of treatment using them.

Claims27

Dependent claims

A compound of Formula (I):

or a stereoisomeric, tautomeric or salt form thereof, wherein:
the dashed lines between positions 1, 2 and 3 in Formula (I) indicate the positions of a tautomeric double bond,
wherein when a double bond is formed between positions 1 and 2, then R3b is present, and
wherein, when a double bond is formed between positions 2 and 3, then R3a is present;
p is 0, 1 or 2;
q is 0, 1 or 2;
r is 0, 1, 2 or 3;
L is —X—C1-3alkyl- or —C1-3alkyl-Y—, wherein each instance of alkyl is optionally perfluorinated;
X and Y are each O, S, SO, SO2 or NR6;
A1 is selected from the group consisting of indanyl, 1,2,3,4-tetrahydro-naphthalenyl, phenyl, naphthyl, benzo[1,3]dioxolyl, pyridinyl and quinolinyl;
R1 is C1-6alkylsulfonyl, C1-6alkylsulfonylamino, aminosulfonyl or (C1-4alkyl)1-2aminosulfonyl,
wherein each instance of alkyl is optionally substituted with one, two or three substituents independently selected from the group consisting of C1-8alkoxy, amino, (C1-4alkyl)1-2amino, C1-6alkylcarbonylamino, C1-6alkoxycarbonylamino, aminocarbonylamino, (C1-6alkyl)1-2aminocarbonylamino, C1-6alkylsulfonylamino, halogen, oxo and hydroxy, and
wherein, each instance of alkyl and alkoxy is optionally perfluorinated;
R2 is each selected from the group consisting of halogen, C1-4alkyl, C1-4alkoxy, C1-4alkylsulfonyl, nitro, (C1-4alkyl)1-2amino and cyano, wherein each instance of alkyl and alkoxy is optionally perfluorinated;
R3a and R3b are each selected from the group consisting of hydrogen and C1-4alkyl;
R4 is each halogen, nitro, cyano, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkylthio, haloC1-6alkylthio, C1-6alkylsulfonyl, haloC1-6alkylsulfonyl, C3-8cycloalkyl, C3-8cycloalkyl-C1-4alkyl, C3-8cycloalkyl-C1-4alkoxy, C3-8cycloalkyl-oxy, amino, (C1-6alkyl)1-2amino, (C3-8cycloalkyl)1-2amino, (C3-8cycloalkyl-C1-4alkyl)1-2amino, cyano, C1-6alkylcarbonyl, C1-6alkoxy-carbonyl, C1-6alkoxy-carbonyl-C1-6alkyl, aminocarbonyl, (C1-6alkyl)1-2aminocarbonyl, C1-6alkylcarbonylamino, C1-6alkoxycarbonylamino, aminocarbonylamino, (C1-6alkyl)1-2aminocarbonylamino, C1-6alkylsulfonylamino, aminosulfonyl or (C1-4alkyl)1-2aminosulfonyl, wherein each instance of alkyl and alkoxy is optionally perfluorinated;
R5 is selected from the group consisting of halogen, hydroxy, C1-4alkyl, haloC1-4alkyl, hydroxyC1-4alkyl, C1-4alkoxy, C1-4alkylsulfonyl, nitro, C1-6alkylcarbonyl, C1-6alkoxycarbonyl, amino, (C1-4alkyl)1-2amino, C1-6alkylcarbonylamino, C1-6alkylsulfonylamino, aminosulfonyl, (C1-6alkyl)1-2aminosulfonyl, and cyano, wherein each instance of alkyl and alkoxy is optionally perfluorinated;
and
R6 is one substituent selected from the group consisting of hydrogen and optionally perfluorinated C1-4alkyl.

16 more elements

A compound of Formula (Ia):

or a stereoisomeric, tautomeric or salt form thereof, wherein:
p is 0, 1 or 2;
r is 0, 1, 2 or 3;
L is —X—C1-3alkyl- or —C1-3alkyl-Y—, wherein each instance of alkyl is optionally perfluorinated;
X and Y are each O, S, SO, SO2 or NR6;
A1 is selected from the group consisting of indanyl, 1,2,3,4-tetrahydro-naphthalenyl, phenyl, naphthyl, benzo[1,3]dioxolyl, pyridinyl and quinolinyl;
R1 is C1-6alkylsulfonyl, C1-6alkylsulfonylamino, aminosulfonyl or (C1-4alkyl)1-2aminosulfonyl,
wherein each instance of alkyl is optionally substituted with one, two or three substituents independently selected from the group consisting of C1-8alkoxy, amino, (C1-4alkyl)1-2amino, C1-6alkylcarbonylamino, C1-6alkoxycarbonylamino, aminocarbonylamino, (C1-6alkyl)1-2aminocarbonylamino, C1-6alkylsulfonylamino, halogen, oxo and hydroxy;
R3b is selected from the group consisting of hydrogen and C1-4alkyl;
R4 is each halogen, nitro, cyano, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkylthio, haloC1-6alkylthio, C1-6alkylsulfonyl, haloC1-6alkylsulfonyl, C3-8cycloalkyl, C3-8cycloalkyl-C1-4alkyl, C3-8cycloalkyl-C1-4alkoxy, C3-8cycloalkyl-oxy, amino, (C1-6alkyl)1-2amino, (C3-8cycloalkyl)1-2amino, (C3-8cycloalkyl-C1-4alkyl)1-2amino, cyano, C1-6alkylcarbonyl, C1-6alkoxy-carbonyl, C1-6alkoxy-carbonyl-C1-6alkyl, aminocarbonyl, (C1-6alkyl)1-2aminocarbonyl, C1-6alkylcarbonylamino, C1-6alkoxycarbonylamino, aminocarbonylamino, (C1-6alkyl)1-2aminocarbonylamino, C1-6alkylsulfonylamino, aminosulfonyl or (C1-4alkyl)1-2aminosulfonyl;
R5 is selected from the group consisting of halogen, hydroxy, C1-4alkyl, haloC1-4alkyl, hydroxyC1-4alkyl, C1-4alkoxy, C1-4alkylsulfonyl, nitro, C1-6alkylcarbonyl, C1-6alkoxycarbonyl, amino, (C1-4alkyl)1-2amino, C1-6alkylcarbonylamino, C1-6alkylsulfonylamino, aminosulfonyl, (C1-6alkyl)1-2aminosulfonyl and cyano;
and
R6 is one substituent selected from the group consisting of hydrogen and C1-4alkyl.

10 more elements

A compound selected from the group consisting of:

2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-trifluoromethanesulfonyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(2-fluoro-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(3-fluoro-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-fluoro-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(3-chloro-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-chloro-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-bromo-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(2,4-difluoro-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(3,4-difluoro-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(3-chloro-4-fluoro-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-fluoro-3-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(3-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(2,3,4-trifluoro-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(3-trifluoromethoxy-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-trifluoromethoxy-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
N-methyl-2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-chloro-phenoxymethyl)-1H-benzoimidazol-5-yl]-N-methyl-benzenesulfonamide,
2-[2-(4-methanesulfonyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-N-methyl-benzenesulfonamide,
N-methyl-2-[2-(4-trifluoromethanesulfonyl-phenoxymethyl)-1H-benzoimidazol-5 yl]-benzenesulfonamide,
2-(2-phenoxymethyl-1H-benzoimidazol-5-yl)-benzenesulfonamide,
2-(2-p-tolyloxymethyl-1H-benzoimidazol-5-yl)-benzenesulfonamide,
2-[2-(4-isopropyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(3,4-dichloro-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-chloro-3-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(3,5-bis-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-tert-butyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-ethoxy-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-trifluoromethylsulfanyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-acetyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(naphthalen-2-yloxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(quinolin-6-yloxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(pyridin-4-yloxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(5-trifluoromethyl-pyridin-2-yloxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[1-methyl-2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-trifluoromethyl-phenylsulfanylmethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-chloro-phenylsulfanylmethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-trifluoromethoxy-phenylsulfanylmethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-trifluoromethyl-benzenesulfonylmethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-chloro-benzenesulfonylmethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-trifluoromethoxy-benzenesulfonylmethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-{2-[(4-trifluoromethyl-phenylamino)-methyl]-1H-benzoimidazol-5-yl}-benzenesulfonamide,
2-{2-[(4-trifluoromethoxy-phenylamino)-methyl]-1H-benzoimidazol-5-yl}-benzenesulfonamide,
2-[2-(4-isopropyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-N-methyl-benzenesulfonamide,
N-methyl-2-[2-(3-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
5-(2-methanesulfonyl-phenyl)-2-phenoxymethyl-1H-benzoimidazole,
2-(2-fluoro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(3-fluoro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(4-fluoro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(2-chloro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(3-chloro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(4-chloro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(3-bromo-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(4-bromo-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(2,4-difluoro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(3,4-difluoro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(2,4-dichloro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(3,4-dichloro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(4-chloro-2-fluoro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(3-chloro-4-fluoro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
5-(2-methanesulfonyl-phenyl)-2-(3,4,5-trifluoro-phenoxymethyl)-1H-benzoimidazole,
5-(2-methanesulfonyl-phenyl)-2-(2,4,5-trifluoro-phenoxymethyl)-1H-benzoimidazole,
5-(2-methanesulfonyl-phenyl)-2-(2,3,4-trifluoro-phenoxymethyl)-1H-benzoimidazole,
2-(2-fluoro-3-trifluoromethyl-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(4-fluoro-3-trifluoromethyl-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(3,5-bis-trifluoromethyl-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
5-(2-methanesulfonyl-phenyl)-2-(2-trifluoromethyl-phenoxymethyl)-1H-benzoimidazole,
5-(2-methanesulfonyl-phenyl)-2-(3-trifluoromethyl-phenoxymethyl)-1H-benzoimidazole,
5-(2-methanesulfonyl-phenyl)-2-p-tolyloxymethyl-1H-benzoimidazole,
2-(4-isopropyl-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(4-tert-butyl-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
1-{4-[5-(2-methanesulfonyl-phenyl)-1H-benzoimidazol-2-ylmethoxy]-phenyl}-ethanone,
5-(2-methanesulfonyl-phenyl)-2-(naphthalen-2-yloxymethyl)-1H-benzoimidazole,
2-(4-ethoxy-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
5-(2-methanesulfonyl-phenyl)-2-(4-trifluoromethanesulfide-phenoxymethyl)-1H-benzoimidazole,
4-[5-(2-methanesulfonyl-phenyl)-1H-benzoimidazol-2-ylmethoxy]-benzonitrile,
5-(2-methanesulfonyl-phenyl)-2-(4-trifluoromethoxy-phenoxymethyl)-1H-benzoimidazole,
2-(4-methanesulfonyl-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
5-(2-methanesulfonyl-phenyl)-2-(4-trifluoromethanesulfonyl-phenoxymethyl)-1H-benzoimidazole,
5-(2-methanesulfonyl-phenyl)-2-(5,6,7,8-tetrahydro-naphthalen-2-yloxymethyl)-1H-benzoimidazole,
3-{4-[5-(2-methanesulfonyl-phenyl)-1H-benzoimidazol-2-ylmethoxy]-phenyl}-propionic acid methyl ester,
2-(2,4-dimethyl-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(3,5-dimethyl-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(indan-5-yloxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(benzo[1,3]dioxol-5-yloxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
2-(3,5-dichloro-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole,
N-{3-[5-(2-methanesulfonyl-phenyl)-1H-benzoimidazol-2-ylmethoxy]-phenyl}-acetamide,
N-{4-[5-(2-methanesulfonyl-phenyl)-1H-benzoimidazol-2-ylmethoxy]-phenyl}-acetamide,
5-(2-methanesulfonyl-phenyl)-2-(4-methoxy-phenoxymethyl)-1H-benzoimidazole,
5-(2-methanesulfonyl-phenyl)-2-(3-methoxy-phenoxymethyl)-1H-benzoimidazole,
5-(2-methanesulfonyl-phenyl)-2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazole,
5-(3-methanesulfonyl-phenyl)-2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazole,
5-(4-methanesulfonyl-phenyl)-2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazole,
N-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-methanesulfonamide,
N-{3-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-methanesulfonamide,
N-{4-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-methanesulfonamide,
3-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
4-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
N,N-dimethyl-2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
N-methyl-4-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
N,N-dimethyl-3-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide
N,N-dimethyl-4-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide
4-trifluoromethyl-2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
5-trifluoromethyl-2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
4-fluoro-2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2,4-difluoro-6-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-trifluoromethyl-benzylamino)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-{2-[methyl-(4-trifluoromethyl-benzyl)-amino]-1H-benzoimidazol-5-yl}-benzenesulfonamide,
2-[2-(4-trifluoromethyl-benzyloxy)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-{2-[difluoro-(4-trifluoromethyl-phenoxy)-methyl]-1H-benzoimidazol-5-yl}-benzenesulfonamide,
2-{2-[difluoro-(4-trifluoromethyl-phenoxy)-methyl]-1H-benzoimidazol-5-yl}-N-methyl-benzenesulfonamide,
2-{2-[difluoro-(4-trifluoromethyl-phenoxy)-methyl]-1H-benzoimidazol-5-yl}-N,N-dimethyl-benzenesulfonamide,
2-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonyl}-ethanol,
2-{2-[1-(4-trifluoromethyl-phenoxy)-ethyl]-1H-benzoimidazol-5-yl}-benzenesulfonamide,
2-{2-[1-(4-trifluoromethyl-phenoxy)-propyl]-1H-benzoimidazol-5-yl}-benzenesulfonamide,
5-(2-trifluoromethanesulfonyl-phenyl)-2-(4-trifluoromethyl-phenoxymethyl)-H-benzoimidazole,
2-methyl-1-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonyl}-propan-2-ol,
1-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonyl}-propan-2-ol,
2-{2-[2-(4-trifluoromethanesulfonyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonyl}-ethanol,
2-{2-[2-(4-methanesulfonyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonyl}-ethanol,
2-[2-(4-cyclopropyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-benzenesulfonamide,
2-[2-(4-cyclopropyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-N-methyl-benzenesulfonamide,
2-[2-(4-cyclopropyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-N,N-dimethyl-benzenesulfonamide,
2-(4-cyclopropyl-phenoxymethyl)-5-(2-methanesulfonyl-phenyl)-1H-benzoimidazole, and
N-{2-[2-(4-cyclopropyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-methanesulfonamide.

122 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/954,647Filed 12 Dec 2007 · us provisional application
Priority: 15 Dec 2006
Published: US 2008/0146637 A119 Jun 2008
Granted: 3 Nov 2009
Term ends: Not estimatedThe source records don’t support an estimate.

Classification13 codes

C07D 235/12
With only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2: radicals substituted by oxygen atoms
A61P 17/02
Drugs for dermatological disorders: for treating wounds, ulcers, burns, scars, keloids, or the like
A61P 25/04
Drugs for disorders of the nervous system: centrally acting analgesics, e.g. opioids
A61P 29/00
Non-central analgesic, antipyretic or antiinflammatory agents

Family

Application60/870,212Us provisional application · filed 15 Dec 2006
US 2008/0146637 A1Pre-grant publication · published 19 Jun 2008
US 7,612,211 B2This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

Open elsewhere

Building an agent or pulling many patents? Use the API or MCP server instead of scraping pages. Get an API key

patentgrep

Loading patent…

Abstract

The invention is directed to compounds of Formula (I): to pharmaceutical compositions containing such compounds and to methods of treatment using them.

A compound of Formula (I):

or a stereoisomeric, tautomeric or salt form thereof, wherein:
the dashed lines between positions 1, 2 and 3 in Formula (I) indicate the positions of a tautomeric double bond,
wherein when a double bond is formed between positions 1 and 2, then R3b is present, and
wherein, when a double bond is formed between positions 2 and 3, then R3a is present;
p is 0, 1 or 2;
q is 0, 1 or 2;
r is 0, 1, 2 or 3;
L is —X—C1-3alkyl- or —C1-3alkyl-Y—, wherein each instance of alkyl is optionally perfluorinated;
X and Y are each O, S, SO, SO2 or NR6;
A1 is selected from the group consisting of indanyl, 1,2,3,4-tetrahydro-naphthalenyl, phenyl, naphthyl, benzo[1,3]dioxolyl, pyridinyl and quinolinyl;
R1 is C1-6alkylsulfonyl, C1-6alkylsulfonylamino, aminosulfonyl or (C1-4alkyl)1-2aminosulfonyl,
wherein each instance of alkyl is optionally substituted with one, two or three substituents independently selected from the group consisting of C1-8alkoxy, amino, (C1-4alkyl)1-2amino, C1-6alkylcarbonylamino, C1-6alkoxycarbonylamino, aminocarbonylamino, (C1-6alkyl)1-2aminocarbonylamino, C1-6alkylsulfonylamino, halogen, oxo and hydroxy, and
wherein, each instance of alkyl and alkoxy is optionally perfluorinated;
R2 is each selected from the group consisting of halogen, C1-4alkyl, C1-4alkoxy, C1-4alkylsulfonyl, nitro, (C1-4alkyl)1-2amino and cyano, wherein each instance of alkyl and alkoxy is optionally perfluorinated;
R3a and R3b are each selected from the group consisting of hydrogen and C1-4alkyl;
R4 is each halogen, nitro, cyano, C1-6alkyl, C1-6alkoxy, haloC1-6alkyl, haloC1-6alkoxy, C1-6alkoxy-C1-6alkyl, C1-6alkylthio, haloC1-6alkylthio, C1-6alkylsulfonyl, haloC1-6alkylsulfonyl, C3-8cycloalkyl, C3-8cycloalkyl-C1-4alkyl, C3-8cycloalkyl-C1-4alkoxy, C3-8cycloalkyl-oxy, amino, (C1-6alkyl)1-2amino, (C3-8cycloalkyl)1-2amino, (C3-8cycloalkyl-C1-4alkyl)1-2amino, cyano, C1-6alkylcarbonyl, C1-6alkoxy-carbonyl, C1-6alkoxy-carbonyl-C1-6alkyl, aminocarbonyl, (C1-6alkyl)1-2aminocarbonyl, C1-6alkylcarbonylamino, C1-6alkoxycarbonylamino, aminocarbonylamino, (C1-6alkyl)1-2aminocarbonylamino, C1-6alkylsulfonylamino, aminosulfonyl or (C1-4alkyl)1-2aminosulfonyl, wherein each instance of alkyl and alkoxy is optionally perfluorinated;
R5 is selected from the group consisting of halogen, hydroxy, C1-4alkyl, haloC1-4alkyl, hydroxyC1-4alkyl, C1-4alkoxy, C1-4alkylsulfonyl, nitro, C1-6alkylcarbonyl, C1-6alkoxycarbonyl, amino, (C1-4alkyl)1-2amino, C1-6alkylcarbonylamino, C1-6alkylsulfonylamino, aminosulfonyl, (C1-6alkyl)1-2aminosulfonyl, and cyano, wherein each instance of alkyl and alkoxy is optionally perfluorinated;
and
R6 is one substituent selected from the group consisting of hydrogen and optionally perfluorinated C1-4alkyl.

16 more elements

Facts

Application

11/954,647Filed 12 Dec 2007 · us provisional application

Priority

15 Dec 2006

Published

US 2008/0146637 A119 Jun 2008

Granted

3 Nov 2009

Term ends

Not estimatedThe source records don’t support an estimate.

Classification13 codes

C07D 235/12
With only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2: radicals substituted by oxygen atoms
A61P 17/02
Drugs for dermatological disorders: for treating wounds, ulcers, burns, scars, keloids, or the like
A61P 25/04
Drugs for disorders of the nervous system: centrally acting analgesics, e.g. opioids
A61P 29/00
Non-central analgesic, antipyretic or antiinflammatory agents