Heterocyclic compound and use thereof
US-9221836-B2 · Dec 29, 2015 · US
3-heteroaroylamino-propionic acid derivatives and their use as pharmaceuticals
US9751858B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9751858-B2 |
| Application number | US-201615140350-A |
| Country | US |
| Kind code | B2 |
| Filing date | Apr 27, 2016 |
| Priority date | Jul 26, 2011 |
| Publication date | Sep 5, 2017 |
| Grant date | Sep 5, 2017 |
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- Title
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- Abstract
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Abstract
Official abstract text for this publication.
The present invention relates to compounds of the formula I, wherein Ht, G, R 10 , R 30 , R 40 , R 50 and R 60 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. They are inhibitors of the protease cathepsin A, and are useful for the treatment of diseases such as atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.
First claim
Opening claim text (preview).
The invention claimed is: 1. A compound selected from the group consisting of: 3-Cyclohexyl-3-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; 3-[(5-Methyl-2-phenyl-oxazole-4-carbonyl)-amino]-4-phenyl-butyric acid; (S)-3-[(5-Methyl-2-phenyl-oxazole-4-carbonyl)-amino]-3-o-tolyl-propionic acid; (S)-3-(2-Fluoro-phenyl)-3-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-(3-Fluoro-phenyl)-3-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-(4-Fluoro-phenyl)-3-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-{[2-(2-Fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-phenyl-propionic acid; (R)-3-{[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazole-5-carbonyl]-amino}-4-phenyl-butyric acid; (S)-3-{[5-(2-Fluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-p-tolyl-propionic acid; (R)-3-{[5-(2-Fluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-4-phenyl-butyric acid; (S)-3-{[5-(2-Fluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-phenyl-butyric acid; (S)-3-{[5-(2-Fluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-o-tolyl-propionic acid; (S)-3-{[5-(2-Fluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-m-tolyl-propionic acid; (S)-3-(2-Fluoro-phenyl)-3-{[5-(2-fluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-propionic acid; (S)-3-(3-Fluoro-phenyl)-3-{[5-(2-fluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-propionic acid; (S)-3-(4-Fluoro-phenyl)-3-{[5-(2-fluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-propionic acid; (S)-3-{[5-(2,3-Difluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-phenyl-propionic acid; (S)-3-[(1-Ethyl-5-phenyl-1H-pyrazole-3-carbonyl)-amino]-3-o-tolyl-propionic acid; (S)-3-[(5-Isopropyl-2-phenyl-oxazole-4-carbonyl)-amino]-3-phenyl-propionic acid; (S)-3-(4-Methoxy-phenyl)-3-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-(3-Methoxy-phenyl)-3-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-{[2-(2-Fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-o-tolyl-propionic acid; (S)-3-{[2-(2-Fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-m-tolyl-propionic acid; (S)-3-(3-Chloro-phenyl)-3-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (R)-3-{[2-(2-Fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-4-phenyl-butyric acid; (S)-3-{[2-(2-Fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-phenyl-butyric acid; (S)-3-{3-[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionylamino}-3-phenyl-propionic acid; (S)-3-(2-Chloro-phenyl)-3-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; 3-Cyclohexyl-3-[(5-isopropyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-(2-Fluoro-phenyl)-3-{[2-(2-fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-propionic acid; (S)-3-(3-Fluoro-phenyl)-3-{[2-(2-fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-propionic acid; (S)-3-(4-Fluoro-phenyl)-3-{[2-(2-fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-propionic acid; (S)-3-{[5-(2,3-Difluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-p-tolyl-propionic acid; (S)-3-{[5-(2,3-Difluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-m-tolyl-propionic acid; (S)-3-{[5-(2,3-Difluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-phenyl-butyric acid; (R)-3-{[5-(2,3-Difluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-4-phenyl-butyric acid; (S)-3-{[5-(2,3-Difluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-o-tolyl-propionic acid; (S)-3-{[5-(2,3-Difluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-(2-fluoro-phenyl)-propionic acid; (S)-3-{[5-(2,3-Difluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-(4-fluoro-phenyl)-propionic acid; 3-[(5-Isopropyl-2-phenyl-oxazole-4-carbonyl)-amino]-4-phenyl-butyric acid; (S)-3-[(5-Dimethylsulfamoyl-2-methyl-furan-3-carbonyl)-amino]-3-o-tolyl-propionic acid; (S)-3-(2-Fluoro-phenyl)-3-[(5-isopropyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-(4-Fluoro-phenyl)-3-[(5-isopropyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (R)-3-{3-[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionylamino}-4-phenyl-butyric acid; (S)-3-{3-[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionylamino}-3-m-tolyl-propionic acid; (S)-3-{3-[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionylamino}-3-phenyl-butyric acid; (S)-3-{3-[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionylamino}-3-p-tolyl-propionic acid; (S)-3-{3-[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionylamino}-3-o-tolyl-propionic acid; (S)-3-(4-Fluoro-phenyl)-3-{3-[3-(2-fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionylamino}-propionic acid; (S)-3-(2-Fluoro-phenyl)-3-{3-[3-(2-fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionylamino}-propionic acid; (S)-3-(3-Fluoro-phenyl)-3-{3-[3-(2-fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionylamino}-propionic acid; (S)-3-(3-Chloro-phenyl)-3-{[2-(2-fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-propionic acid; 3-(2-Chloro-phenyl)-3-{[2-(2-fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-propionic acid; (S)-3-(4-Chloro-phenyl)-3-{[2-(2-fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-propionic acid; (S)-3-{[1-Methyl-4-(propane-1-sulfonylamino)-1H-pyrazole-3-carbonyl]-amino}-3-o-tolyl-propionic acid; (S)-3-[(5-Isopropyl-2-phenyl-oxazole-4-carbonyl)-amino]-3-(3-methoxy-phenyl)-propionic acid; (S)-3-(2,3-Dimethoxy-phenyl)-3-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-(2-Chloro-phenyl)-3-[(5-isopropyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; 3-Cyclohexyl-3-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-{3-[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionylamino}-3-(4-methoxy-phenyl)-propionic acid; (S)-3-(3-Chloro-phenyl)-3-{3-[3-(2-fluoro-phenyl)-[1,2,4]oxadiazol-5-yl]-propionylamino}-propionic acid; (S)-3-(2,4-Dichloro-phenyl)-3-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-(2,3-Dichloro-phenyl)-3-[(5-methyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-3-o-tolyl-propionic acid; (S)-3-[(5-Methyl-2-phenyl-oxazole-4-carbonyl)-amino]-3-(2-trifluoromethyl-phenyl)-propionic acid; (S)-3-(3-Fluoro-phenyl)-3-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-{[5-(2-Fluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-(2-trifluoromethyl-phenyl)-propionic acid; (S)-3-{[5-(2-Fluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-(3-trifluoromethyl-phenyl)-propionic acid; (S)-3-{[2-(2-Fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(3-trifluoromethyl-phenyl)-propionic acid; (S)-3-{[2-(2-Fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(4-trifluoromethyl-phenyl)-propionic acid; (S)-3-(2,3-Dichloro-phenyl)-3-{[2-(2-fluoro-phenyl)-5-methyl-oxazole-4-carbonyl]-amino}-propionic acid; (S)-3-{[4-(2,2-Dimethyl-propane-1-sulfonylamino)-1-methyl-1H-pyrazole-3-carbonyl]-amino}-3-o-tolyl-propionic acid; (S)-3-(3-Chloro-phenyl)-3-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-(2-Chloro-phenyl)-3-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-[(1-Benzyl-5-phenyl-1H-pyrazole-3-carbonyl)-amino]-3-o-tolyl-propionic acid; (S)-3-(4-Chloro-phenyl)-2-{[5-(4-trifluoromethyl-pyridin-3-yl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-propionic acid; (S)-3-{[1-Ethyl-5-(2-propyl-piperidine-1-carbonyl)-1H-pyrazole-3-carbonyl]-amino}-3-phenyl-propionic acid; (S)-3-{[5-(2,3-Difluoro-phenyl)-[1,2,4]oxadiazole-3-carbonyl]-amino}-3-(2-trifluoromethyl-phenyl)-propionic acid; (S)-3-(2,3-Dichloro-phenyl)-3-[(5-isopropyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-(2,4-Dichloro-phenyl)-3-[(5-isopropyl-2-phenyl-oxazole-4-carbonyl)-amino]-propionic acid; (S)-3-[(4-Cyclohexylmethanesulfonylamino-1-methyl-1H-pyrazole-3-carbonyl)-amino]-3-phenyl-propionic acid; (S)-3-{3-[3-(2-Fluoro-phenyl)-[1,2,4]oxadiazol-5-
Assignees
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Drugs for disorders of the cardiovascular system · CPC title
for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis · CPC title
Vasodilators for multiple indications · CPC title
Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure · CPC title
Drugs for immunological or allergic disorders · CPC title
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- What does patent US9751858B2 cover?
- The present invention relates to compounds of the formula I, wherein Ht, G, R 10 , R 30 , R 40 , R 50 and R 60 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. They are inhibitors of the protease cathepsin A, and are useful for the treatment of diseases such as atherosclerosis, heart failure, renal diseases, liver diseas…
- Who is the assignee on this patent?
- Sanofi Sa
- What technology area does this patent fall under?
- Primary CPC classification C07D233/90. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Sep 05 2017 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 8 related publications on this page (citations in our corpus or others sharing the same primary CPC).