US 7,410,991 B2 · Pyrazolidinone compounds as ligands of the prostaglandin EP2 and/or EP4 receptors

Abstract

The invention provides substituted pyrazolidinone compounds, and methods of treatment and pharmaceutical compositions that utilize or comprise one or more such compounds. Compounds of the invention are useful for a variety of therapies, including treating or preventing preterm labor, dysmenorrhea, asthma, hypertension, infertility or fertility disorder, undesired blood clotting, preeclampsia or eclampsia, an eosinophil disorder, sexual dysfunction, osteporosis and other destructive bone disease or disorder, and other diseases and disorders associated with the prostaglandin EP2 and/or EP4 receptors.

Claims9

Dependent claims

A compound of the following Formula VI:

Wherein M is COX with X is OR′ and R′ is H;
D is (CH2)n″ wherein n″ is 2;
Q is (CH2)n′″ wherein n′″ is 0 or 1;
R5 is H or C1-C6 alkyl;
and
R6 is —CHR7—W, wherein R7 is H or C1-C6 alkyl;
W is phenyl.

4 more elements

A compound selected from the group consisting of:

4-[2-(2-(3-hydroxyoctyl)-5-oxopyrazolidin-1-yl)ethyl]benzoic acid;
4-{2-[2-(4-hydroxynon-2-ynyl)-5-oxopyrazolidin-1-yl]ethyl}benzoic acid;
4-{2-[2-(4-hydroxynonyl)-5-oxopyrazolidin-1-yl]ethyl }benzoic acid;
4-(2-{2-[(2Z)-4-hydroxynon-2-enyl]-5-oxopyrazolidin-1-yl)ethyl)benzoic acid;
4-(2-{2-[(2E)-4-hydroxynon-2-enyl]-5-oxopyrazolidin-1-yl)ethyl)benzoic acid;
4-{2-[2-(4-hydroxyoctyl)-5-oxopyrazolidin-1-yl]ethyl) benzoic acid;
4-{2-[2-(4-hydroxy-6-methylheptyl)-5-oxopyrazolidin-1-yl]ethyl}benzoic acid;
4-{2-[2-(4-hydroxy-5-methyloctyl)-5-oxopyrazolidin-1-yl)ethyl}benzoic acid;
4-{2-[2-(4-ethyl-4-hydroxyoctyl)-5-oxopyrazolidin-1-yl]ethyl}benzoic acid;
4-{2-[2-(4-hydroxy-4-methylheptyl)-5-oxopyrazolidin-1-yl]ethyl}benzoic acid;
4-(2-[2-(4-hydroxy-4,7-dimethyloctyl)-5-oxopyrazolidin-1-yl]ethyl}benzoic acid;
4-{2-[2-(3 -hydroxy-5-methylhexyl)-5-oxopyrazolidin-1-yl]ethyl) benzoic acid;
4-{2-[2-(3 -cyclobutyl-3-hydroxypropyl)-5-oxopyrazolidin-1-yl]ethyl}benzoic acid;
4-{2-[2-((4S)-hydroxynonyl)-5-oxopyrazolidin-1-yl]ethyl}benzoic acid;
4-{2-[2-((4R)-hydroxynonyl)-5-oxopyrazolidin-1-yl]ethyl }benzoic acid;
4-[2-(2-{4-[1-(cyclopropylmethyl)cyclobutyl]-4-hydroxybutyl)-5-oxopyrazolidin-1-yl)ethyl]benzoic acid;
4-(2-{2-[4-(1-ethylcyclobutyl)-4-hydroxybutyl]-5-oxopyrazolidin-1-yl)ethyl)benzoic acid;
4-(2-{2-[3-hydroxy-4-(3-methylphenyl)butyl]-5-oxopyrazolidin-1-yl)ethyl)benzoic acid;
4-{2-[2-(3-hydroxy-4-phenylbutyl)-5-oxopyrazolidin-1-yl]ethyl}benzoic acid;
4-(2-{2-[4-(3-iodophenyl)-3-hydroxybutyl]-5-oxopyrazolidin-1-yl}ethyl) benzoic acid;
4-(2-{2-[4-(3-bromophenyl)-3-hydroxybutyl]-5-oxopyrazolidin-1-yl)ethyl)benzoic acid;
4-[2-(2-{3-hydroxy-4-[3-(trifluoromethoxy)phenyl]butyl)-5-oxopyrazolidin-1-yl) ethyl]benzoic acid;
4-(2-{2-[4-(3-fluorophenyl)-3-hydroxybutyl]-5-oxopyrazolidin-1-yl }ethyl) benzoic acid;
4-[2-(2-{3-hydroxy-4-[3-(trifluoromethyl)phenyl]butyl}-5-oxopyrazolidin-1-yl) ethyl]benzoicacid;
4-(2-{2-[(3S, 4S)-3-hydroxy-4-phenylpentyl]-5-oxopyrazolidin-1-yl}ethyl) benzoic acid;
4-(2-(2-[4-(1,3-benzodioxol-5-yl)-3-hydroxybutyl]-5-oxopyrazolidin-1-yl}ethyl) benzoicacid;
4-(2-{2-[4-(3-chlorophenyl)-3-hydroxybutyl]-5-oxopyrazolidin-1-yl}ethyl) benzoic acid;
4-(2-{2-[(4R)-3-hydroxy-4-phenylpentyl]-5-oxopyrazolidin-1-yl)ethyl)benzoic acid;
and pharmaceutically acceptable salts thereof.

26 more elements

Dependencies are inferred from the claim text.

Facts

Application

10/492,910Filed 23 Oct 2002 · us provisional application

Priority

23 Oct 2001

Published

US 2004/0254233 A116 Dec 2004

Granted

12 Aug 2008

Term ends

Not estimatedThe source records don’t support an estimate.

Classification31 codes

A61K 31/4152
1,2-Diazoles: having oxo groups directly attached to the heterocyclic ring, e.g. antipyrine, phenylbutazone, sulfinpyrazone
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 5/24
Drugs for disorders of the endocrine system: of the sex hormones
A61P 7/00
Drugs for disorders of the blood or the extracellular fluid

Pyrazolidinone compounds as ligands of the prostaglandin EP2 and/or EP4 receptors

Life of this patent

Pyrazolidinone compounds as ligands of the prostaglandin EP2 and/or EP4 receptors

Life of this patent

Abstract

Claims9