US 8,580,841 B2 · Substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives useful in the treatment of autoimmune and inflammatory disorders

Abstract

The present invention relates to certain substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives of Formula (Ia): and pharmaceutically acceptable salts thereof, which exhibit useful pharmacological properties, for example, as agonists of the S1P1 receptor. Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the treatment of S1P1 receptor-associated disorders, for example, psoriasis, rheumatoid arthritis, Crohn's disease, transplant rejection, multiple sclerosis, systemic lupus erythematosus, ulcerative colitis, type I diabetes, acne, microbial infections or diseases and viral infections or diseases.

Claims51

Dependent claims

A compound selected from compounds of Formula (Ia) and pharmaceutically acceptable salts, solvates and hydrates thereof:

wherein:
m is 1;
n is 1 or 2;
Y is N or CR1;
Z is N or CR4;
R1, R2, and R4 are each independently selected from the group consisting of H, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylamino, C1-C6 alkylsulfonyl, C1-C6 alkylthio, carboxamide, cyano, C3-C7 cycloalkoxy, C3-C7 cycloalkyl, C1-C6 haloalkoxy, C1-C6 haloalkyl, halogen, heteroaryl and heterocyclyl, wherein said C1-C6 alkyl and C1-C6 alkoxy are each optionally substituted with one or two substituents selected from C3-C7 cycloalkyl and halogen;
and
R3 is C3-C7 cycloalkyl.

5 more elements

Dependencies are inferred from the claim text.

Facts

Application

13/055,333Filed 22 Jul 2009 · us provisional application

Priority

23 Jul 2008

Published

US 2011/0130409 A12 Jun 2011

Granted

12 Nov 2013

Term ends

Not estimatedThe source records don’t support an estimate.

Classification46 codes

C07D 209/94
[b, c]- or [b, d]-condensed: containing carbocyclic rings other than six-membered
A61K 31/137
Having aromatic rings , e.g. ketamine, nortriptyline: arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
A61K 31/198
The amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine,…:…
A61K 31/404
Condensed with carbocyclic rings, e.g. carbazole: indoles, e.g. pindolol

Substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives useful in the treatment of autoimmune and inflammatory disorders

Life of this patent

Substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives useful in the treatment of autoimmune and inflammatory disorders

Life of this patent

Abstract

Claims51