IP Library Granted Patent US 10,087,184
Granted Patent B2
US 10,087,184 · App. 15/709,903 · Granted Oct 2, 2018

Dihydropyrrolopyridine inhibitors of RORγ

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 10,087,184
App. No.
15/709,903
Granted
Oct 2, 2018
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 γ . 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 method of treating dry eye in a subject, comprising administering to the subject a therapeutically effective amount of a compound having the formula:

or a pharmaceutically acceptable salt thereof.

2. A method of treating dry eye in a subject, comprising administering to the subject a therapeutically effective amount of a compound having 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).

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

or a pharmaceutically acceptable salt thereof.

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

or a pharmaceutically acceptable salt thereof.

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

or a pharmaceutically acceptable salt thereof.

6. The method of claim 5 , 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).

7. The method of claim 6 , 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 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.

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

or a pharmaceutically acceptable salt thereof.

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

or a pharmaceutically acceptable salt thereof.

10. The method of claim 9 , wherein R 2 is methyl, ethyl, benzyl, or isopropyl.

11. The method of claim 10 , wherein R 2 is ethyl or isopropyl.

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

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

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 Oct 16, 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 043871/0903 →
Continuity (5)
Continuation 15277836 · Sep 27, 2016
Continuation PCTUS2015055420 · Oct 14, 2015
Provisional Application 62074406 · Nov 3, 2014
Provisional Application 62063912 · Oct 14, 2014
Related Publication 20180222902A1 · Aug 9, 2018