Adenylyl cyclase inhibitors for neuropathic and inflammatory pain

Patent metadata

Field	Value
Publication number	US-10100001-B2
Application number	US-201615044660-A
Country	US
Kind code	B2
Filing date	Feb 16, 2016
Priority date	Feb 16, 2015
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

The invention generally relates to adenylyl cyclase inhibitor compounds and methods for treating neuropathic or inflammatory pain by using those compounds.

First claim

What is claimed is:

1. A compound of formula (I):

wherein:
X is nitrogen;
n is 1;
R 1 is an alkyl substituted by a fused heterocycloalkenyl, wherein said fused heterocycloalkenyl is substituted at the heteroatom by alkyl, wherein said fused heterocycloalkenyl is

R 2 is a branched or unbranched alkyl substituted by aryl, wherein the aryl is optionally substituted by halo, NO 2 , or alkoxy, wherein said aryl is phenyl;
R 3 is

wherein Ar is phenyl optionally substituted at any ring position by alkyl, halo, COOR 4 , NO 2 , alkoxy, OOR 4 , or haloalkyl; and
R 4 is alkyl.

2. A compound of formula (I):

wherein:
X is nitrogen;
n is 1;
R 1 is an alkyl substituted by a fused heterocycloalkenyl, wherein said fused heterocycloalkenyl is

R 2 is a branched or unbranched alkyl substituted by aryl, wherein the aryl is optionally substituted by halo, NO 2 , or alkoxy, wherein said aryl is phenyl; and
R 3 is

wherein Ar is phenyl substituted by iodine, chlorine, bromine, or COOR 6 , wherein R 6 is alkyl.

3. A method of treating neuropathic or inflammatory pain, the method comprising administering a pharmaceutical composition comprising a compound of formula (I) and a pharmaceutically acceptable carrier to a patient:

wherein:
X is nitrogen;
n is 1;
R 1 is an alkyl substituted by an indolyl, wherein the nitrogen of the indolyl is optionally substituted by alkyl;
R 2 is an alkyl substituted by aryl, wherein the aryl is optionally substituted by halo, NO 2 , or alkoxy, wherein said aryl is phenyl or naphthyl; and
R 3 is

wherein Ar is a phenyl optionally substituted at any ring position by alkyl, halo, COOR 4 , NO 2 , alkoxy, OOR 4 , or haloalkyl; and
R 4 is alkyl.

Assignees

• Purdue Research Foundation

Inventors

• Dai Mingji
• Watts Val J
• Ye Zhishi

Classifications

• C07D223/16

  Benzazepines; Hydrogenated benzazepines · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C07C211/27

  having amino groups linked to the six-membered aromatic ring by saturated carbon chains · CPC title

• C07C311/16

  having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom · CPC title

• C07C211/28 Primary

  having amino groups linked to the six-membered aromatic ring by unsaturated carbon chains · CPC title