IP Library Granted Patent US 9,796,710
Granted Patent B2
US 9,796,710 · App. 15/277,836 · Granted Oct 24, 2017

Dihydropyrrolopyridine inhibitors of ROR-gamma

Inventors: David A. Claremon (Maple Glen, PA); Lawrence Wayne Dillard (Yardley, PA); Chengguo Dong (Staten Island, NY); Yi Fan (Doylestown, PA); Lanqi Jia (Horsham, PA); Stephen D. Lotesta (Burlington, NJ); Andrew Marcus (Media, PA); Suresh B. Singh (Kendall Park, NJ); Colin M. Tice (Maple Glen, PA); Jing Yuan (Lansdale, PA); Wei Zhao (North Potomac, MD); Yajun Zheng (Hockessin, DE); Linghang Zhuang (Chalfont, PA)
Assignee: Vitae Pharmaceuticals, Inc.
C07D471/04
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Quick Facts
Patent No.
US 9,796,710
App. No.
15/277,836
Granted
Oct 24, 2017
Kind
B2
Abstract

Provided are novel compounds of Formula (I): pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, which are useful in the treatment of diseases and disorders mediated by ROR . Also provided are pharmaceutical compositions comprising the novel compounds of Formula (I) and methods for their use in treating one or more inflammatory, metabolic, autoimmune and other diseases or disorders.

Claims (30)

1. A compound of the Formula:

or a pharmaceutically acceptable salt thereof, wherein

R 2 is (C 1 -C 3 )alkyl, hydroxy(C 1 -C 3 )alkyl, halo(C 1 -C 3 )alkyl, benzyl, (C 1 -C 3 )alkoxy(C 1 -C 3 )alkyl, tetrahydropyranyl, or —CH 2 -tetrahydropyranyl;

R 3 and R 4 are each independently hydrogen or methyl;

Cy 1 is phenyl or pyridyl, each substituted with (C 1 -C 3 )alkylsulfonyl; and

Cy 2 is hydrogen, halo(C 1 -C 3 )alkyl, cyclohexyl, or tetrahydropyranyl, wherein the cyclohexyl and tetrahydropyranyl are each optionally substituted with one or more groups selected from halo(C 1 -C 3 )alkyl and C 1 -C 3 (alkoxy).

2. The compound of claim 1 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof.

4. The compound of claim 3 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof.

5. The compound of claim 4 , wherein Cy 2 is cyclohexyl or tetrahydropyranyl, each of which are optionally substituted with one or more groups selected from halo (C 1 -C 3 )alkyl and C 1 -C 3 (alkoxy).

6. The compound of claim 5 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof, wherein

X is CH or N;

Y 1 is O and Y 2 is CH 2 , Y 1 is CH 2 and Y 2 is O, or Y 1 and Y 2 are each CH 2 ;

R 9 is halo(C 1 -C 3 )alkyl; and

R 10 is (C 1 -C 3 )alkylsulfonyl.

7. The compound of claim 6 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof.

8. The compound of claim 7 , wherein the compound is of the Formula:

or a pharmaceutically acceptable salt thereof.

9. The compound of claim 8 , wherein R 2 is methyl, ethyl, benzyl, or isopropyl.

10. The compound of claim 9 , wherein R 2 is ethyl or isopropyl.

11. The compound of claim 10 , wherein R 9 is CF 3 ; and R 10 is SO 2 Et or SO 2 Me.

12. The compound of claim 1 , wherein the compound is selected from

or a pharmaceutically acceptable salt thereof.

13. A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

14. A method of treating psoriasis, psoriatic arthritis (PsA), inflammatory bowel disease (IBD), rheumatoid arthritis, juvenile rheumatoid arthritis, systemic lupus erythematosus (SLE), multiple sclerosis, ankylosing spondylitis, and asthma in a subject, comprising administering to the subject a therapeutically effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

Assignments (2)
CHANGE OF NAME Recorded Mar 20, 2019
From: VITAE PHARMACEUTICALS, INC.
To: VITAE PHARMACEUTICALS, LLC
Reel/Frame 050150/0044 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 4, 2017
From: CLAREMON, DAVID A.; DILLARD, LAWRENCE WAYNE; DONG, CHENGGUO; FAN, YI; JIA, LANQI; LOTESTA, STEPHEN D.; MARCUS, ANDREW; SINGH, SURESH B.; TICE, COLIN M.; YUAN, JING; ZHAO, WEI; ZHENG, YAJUN; ZHUANG, LINGHANG
To: VITAE PHARMACEUTICALS, INC.
Reel/Frame 041846/0131 →
Continuity (4)
Continuation PCTUS2015055420 · Oct 14, 2015
Provisional Application 62074406 · Nov 3, 2014
Provisional Application 62063912 · Oct 14, 2014
Related Publication 20170081327A1 · Mar 23, 2017