2-oxindole compounds

Patent metadata

Field	Value
Publication number	US-11434230-B2
Application number	US-202016932114-A
Country	US
Kind code	B2
Filing date	Jul 17, 2020
Priority date	Jan 20, 2016
Publication date	Sep 6, 2022
Grant date	Sep 6, 2022

Abstract

Oxindole compounds useful for the treatment of CCR(9) mediated conditions or diseases are provided.

First claim

What is claimed is:

1. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound having a formula selected from the group consisting of (Ia1), (Ia2), and (Ia3):

or a pharmaceutically acceptable salt thereof, wherein
Ar is a 5- to 10-membered aromatic or heteroaromatic ring, optionally substituted with from one to three R 3 ;
L 1 is selected from the group consisting of a bond, C 1-6 alkylene, and C 1-6 heteroalkylene,
L 2 is selected from the group consisting of a bond, C 1-6 alkylene, and C 1-6 heteroalkylene,
each R 1 is independently selected from the group consisting of halogen, cyano, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 haloalkyl, C 1-6 haloalkoxy, C 3-6 cycloalkyl, and C 2-6 alkenyl, wherein the alkyl, cycloalkyl and alkenyl portions are optionally substituted with from one to three members selected from fluoro, OH, CN, C 1-3 alkyl, C 1-3 haloalkyl, and C 1-3 alkoxy;
each R 3 is independently selected from the group consisting of halogen, cyano, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 haloalkyl, C 1-6 haloalkoxy, C 3-6 cycloalkyl, and C 2-6 alkenyl; and
the subscript n is an integer of from 0 to 3.

2. The pharmaceutical composition claim 1 , wherein Ar is selected from phenyl, pyridyl, and quinolinyl, each of which is optionally substituted with from one to two R 3 .

3. The pharmaceutical composition claim 1 , wherein L 1 is selected from the group consisting of a bond, —CH 2 — and —CH(CH 3 )—.

4. The pharmaceutical composition claim 1 , wherein L 2 is selected from the group consisting of a bond, —O—CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —, —CH 2 CH 2 —, —CH 2 —, and —CH 2 CH 2 CH 2 —.

5. The pharmaceutical composition of claim 1 , wherein n is 1 or 2.

6. The pharmaceutical composition claim 1 , wherein Ar is selected from the group consisting of 1,3-phenylene and 1,4-phenylene, each of which is optionally substituted with from one to two R 3 .

7. The pharmaceutical composition claim 1 , wherein R 1 is selected from the group consisting of halogen, cyano, C 1-3 alkyl, C 1-3 alkoxy, C 1-3 haloalkyl, C 1-3 haloalkoxy, C 3-5 cycloalkyl, and C 2-3 alkenyl.

8. The pharmaceutical composition claim 1 , wherein R 1 is selected from the group consisting of chloro, methyl, cyano, ethyl, cyclopropyl, trifluoromethyl and trifluoromethoxy.

9. The pharmaceutical composition claim 1 , wherein the compound has a formula selected from the group consisting of:

or a pharmaceutically acceptable salt thereof, wherein said compound is at least 90% free of other isomers.

10. The pharmaceutical composition of claim 1 , wherein R 1 is chloro.

11. The pharmaceutical composition of claim 1 , wherein the compound has the formula

or a pharmaceutically acceptable salt thereof.

12. The pharmaceutical composition of claim 1 , wherein the compound has the formula

or a pharmaceutically acceptable salt thereof.

13. The pharmaceutical composition of claim 1 , wherein the compound has the formula

or a pharmaceutically acceptable salt thereof.

14. The pharmaceutical composition of claim 1 , wherein the compound has the formula

or a pharmaceutically acceptable salt thereof.

Assignees

• Chemocentryx Inc

Inventors

• Chen Xi
• Dragoli Dean R
• Fan Pingchen
• Leleti Manmohan Reddy
• Lui Rebecca M
• Malathong Viengkham
• Powers Jay P
• Singh Rajinder
• Tanaka Hiroko
• Yang Ju
• Yu Chao
• Zhang Penglie

Classifications

• A61K31/404 Primary

  Indoles, e.g. pindolol · CPC title

• C07D209/34 Primary

  in position 2 · CPC title

• C07D405/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D405/14 Primary

  containing three or more hetero rings · CPC title