1434818-13-9

Basic information

• Product Name: benzenesulfonic acid (3S,5S)-5-(1-cyano-cyclopropylcarbamoyl)-1-(1-trifluoromethylcyclopropanecarbonyl)-pyrrolidin-3-yl ester
• Synonyms: benzenesulfonic acid (3S,5S)-5-(1-cyano-cyclopropylcarbamoyl)-1-(1-trifluoromethylcyclopropanecarbonyl)-pyrrolidin-3-yl ester
• CAS NO: 1434818-13-9
• Molecular Weight: 471.457
• Mol File: 1434818-13-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: benzenesulfonic acid (3S,5S)-5-(1-cyano-cyclopropylcarbamoyl)-1-(1-trifluoromethylcyclopropanecarbonyl)-pyrrolidin-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: benzenesulfonic acid (3S,5S)-5-(1-cyano-cyclopropylcarbamoyl)-1-(1-trifluoromethylcyclopropanecarbonyl)-pyrrolidin-3-yl ester(1434818-13-9)
• EPA Substance Registry System: benzenesulfonic acid (3S,5S)-5-(1-cyano-cyclopropylcarbamoyl)-1-(1-trifluoromethylcyclopropanecarbonyl)-pyrrolidin-3-yl ester(1434818-13-9)

Safety Data

• Hazardous Substances Data: 1434818-13-9(Hazardous Substances Data)

Upstream product

• 1434816-61-1 (2S,4R)-4-methanesulfonyloxy-1-(1-trifluoromethyl-cyclopropanecarbonyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 848074-36-2 1-(trifluoromethyl)cyclopropanecarbonyl chloride 
• 1434816-31-5 (2S,4S)-4-hydroxy-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyanocyclopropyl)amide 
• 98-09-9 benzenesulfonyl chloride 
• 277756-46-4 1-(trifluoromethyl)cyclopropanecarboxylic acid 
• 87250-97-3 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 
• 1434816-48-4 (1S,4S)-5-(1-trifluoromethyl-cyclopropanecarbonyl)-2-oxa-5-aza-bicyclo[2.2.1]heptan-3-one 

Downstream Products

• 1252637-46-9 (2S,4R)-4-[4-(2-methylpyridin-4-yl)-2-trifluoromethylbenzenesulfonyl]-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyanocyclopropyl)amide 
• 1434818-59-3 (2S,4R)-4-[4-(2-methylpyridin-4-yl)-2-trifluoromethylphenylsulfanyl]-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyanocyclopropyl)amide 
• 1252637-35-6 (2S,4R)-4-[4-(1-methyl-1H-pyrazol-4-yl)-2-trifluoromethyl-benzenesulfonyl]-1-(1-trifluoromethyl-cyclopropanecarbonyl)-pyrrolidine-2-carboxylic acid (1-cyanocyclopropyl)amide 
• 1434818-70-8 (2S,4R)-4-[4-(1-methyl-1H-pyrazol-4-yl)-2-trifluoromethylphenylsulfanyl]-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyanocyclopropyl)amide 
• 1252634-14-2 (2S,4R)-4-[2-chloro-4-((S)-2,2,2-trifluoro-1-methylethoxy)benzenesulfonyl]-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyano-cyclopropyl)amide 
• 1252637-36-7 (2S,4R)-4-(4-bromo-2-trifluoromethylbenzenesulfonyl)-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyanocyclopropyl)amide 
• 1252637-02-7 (2S,4R)-4-(4-fluoro-2-trifluoromethylbenzenesulfonyl)-1-(1-trifluoromethylcyclopropanecarbonyl)pyrrolidine-2-carboxylic acid (1-cyanocyclopropyl)amide 

Relevant articles and documents

NOVEL PYRROLIDINE DERIVATIVES

The invention relates to a compound of formula (I) wherein R1 and R2 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament against diabetes, atherosclerosis and other conditions linked to cathepsin.

PROCESS FOR THE PREPARATION OF 1-ACYL-4-PHENYLSULFONYLPROLINAMIDE DERIVATIVES AND NEW INTERMEDIATES

A novel process for the preparation of proline derivatives of formula (I) wherein,R1 is selected from C1-7-alkyl or from formula (II) wherein R4 is selected from C1-7-alkyl, halogen-C1-7-alkyl or from phenyl which is optionally substituted by halogen; R2 is selected from halogen or halogen-C1-7-alkyl; and R3 is selected from hydrogen, halogen, halogen-C1-7-alkyl, C1-7-alkoxy, halogen-C1-7-alkoxy or from a 5- or 6-membered heterocyclic ring containing one or two nitrogen atoms, the ring which is optionally substituted by C1-7-alkyl or halogen is described. The proline derivatives of the formula I are preferential inhibitors of the cysteine protease Cathepsin S and are therefore useful to treat metabolic diseases like diabetes, atherosclerosis, abdominal aortic aneurysm, peripheral arterial disease and diabetic nephropathy.