# US 9,518,044 B2 · Prostaglandin receptor EP2 antagonists, derivatives, compositions, and uses related thereto

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- Number: US 9,518,044 B2
- Document ID: US9518044B2
- Status: Granted
- Kind: B2
- Application number: 14/126,689
- Filed: 2012-06-19
- Published: 2014-06-26
- Granted: 2016-12-13
- Earliest claimed: 2011-06-20
- Assignees: Emory University
- Applicants: Jianxiong Jiang; Thota Ganesh; Yuhong Du; Pahk Thepchatri; Yi Quan; Ray J. Dingledine
- Inventors: Jianxiong Jiang; Thota Ganesh; Yuhong Du; Pahk Thepchatri; Yi Quan; Ray J. Dingledine
- Web page: https://patentgrep.com/patent/US9518044B2

## CPC

- C07D 405/12: linked by a chain containing hetero atoms as chain links
- A61K 31/404: Indoles, e.g. pindolol
- A61K 31/4184: condensed with carbocyclic rings, e.g. benzimidazoles
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 11/06: Antiasthmatics
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- C07D 209/08: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C07D 235/08: Radicals containing only hydrogen and carbon atoms
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention is directed to compounds of Formula IC: wherein the substituents are described herein. These compounds and their pharmaceutically acceptable salts thereof are prostaglandin receptor EP2 antagonists.

## Claims

### Claim 1

A pharmaceutical composition comprising a compound of Formula IC,
or pharmaceutically acceptable salt or prodrug thereof, wherein:
W is CH or N;
n is 1, 2, 3, or 4;
Y1, Y2, Y3, Y4, and Y5 are each, the same or different, hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl;
X1, X2, X3, and X4 are each, the same or different, hydrogen, alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl;
X5 is alkyl, wherein X5 is optionally substituted with one or more, the same or different, halogen.

### Claim 2 (depends on 1)

The composition of claim 1, wherein n is 2.

### Claim 3 (depends on 1)

A compound of Formula IC as in claim 1, selected from the group consisting of:
N-(2-(2-methyl-1H-indol-1-yl)ethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide,
3-(3,4-dimethoxyphenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)acrylamide,
N-(2-(2-methyl-1H-benzo[d]imidazol-1-yl)ethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide,
3-(3,4-dimethoxyphenyl)-N-(2-(2-methyl-1H-benzo[d]imidazol-1-yl)ethyl)acrylamide,
3-(benzo[d][1,3]dioxol-5-yl)-N-(2-(2-methyl-1H-benzo[d]imidazol-1-yl)ethyl)acrylamide,
N-(2-(5-fluoro-2-methyl-1H-indol-1-yl)ethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide,
3-(3,4-dimethoxyphenyl)-N-(2-(5-fluoro-2-methyl-1H-indol-1-yl)ethyl)acrylamide,
N-(2-(5-fluoro-2-(trifluoromethyl)-1H-indol-1-yl)ethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide,
3-(3,4-dimethoxyphenyl)-N-(2-(5-fluoro-2-(trifluoromethyl)-1H-indol-1-yl)ethyl)acrylamide,
N-(3-(2-methyl-1H-indol-1-yl)propyl)-3-(3,4,5-trimethoxyphenyl)acrylamide,
N-methyl-N-(2-(2-methyl-1H-indol-1-yl)ethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide,
3-(4-methoxyphenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)acrylamide,
N-(2-(5-fluoro-2-methyl-1H-indol-1-yl)ethyl)-3-(4-methoxyphenyl)acrylamide,
3-(benzo[d][1,3]dioxol-5-yl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)acrylamide,
3-(4-ethoxy-3-methoxyphenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)acrylamide,
3-(4-isobutylphenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)acrylamide,
3-(3,4-difluorophenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)acrylamide,
3-(3,4-difluorophenyl)-N-(2-(5-fluoro-2-methyl-1H-indol-1-yl)ethyl)acrylamide,
N-(2-(2-methyl-1H-indol-1-yl)ethyl)-3-(3,4,5-trifluorophenyl)acrylamide,
N-(2-(5-fluoro-2-methyl-1H-indol-1-yl)ethyl)-3-(3,4,5-trifluorophenyl)acrylamide,
3-(3-bromo-4,5-dimethoxyphenyl)-N-(2-(5-fluoro-2-methyl-1H-indol-1-yl)ethyl)acrylamide,
3-(4-chloro-3-methoxyphenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)acrylamide,
3-(4-chloro-3-methoxyphenyl)-N-(2-(5-fluoro-2-methyl-1H-indol-1-yl)ethyl)acrylamide,
3-(5-bromo-2,4-dimethoxyphenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)acrylamide,
N-(2-(2-(trifluoromethyl)-1H-indol-1-yl)ethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide,
3-(3,5-dimethoxyphenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)acrylamide,
3-(4-fluoro-3,5-dimethylphenyl)-N-(2-(2-(trifluoromethyl)-1H-indol-1-yl)ethyl)acrylamide, and
3-(4-fluoro-3,5-dimethylphenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)acrylamide or salts thereof.