CYCLOALKANECARBOXYLIC ACID AMIDE DERIVATIVE

• Main Authors: TOKUTAKE YOSHIKI, SATO MASAAKI, AKAHA SATOSHI, MUKOYAMA HARUNOBU, KOBAYASHI JUNICHI, TSUYUKI SHOGO
• Format: Patent
• Language: English
• Published: 16.01.2001
• Edition: 7
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS

PROBLEM TO BE SOLVED: To obtain the subject new compound having cysteine protease inhibitory action, and useful as a prophylactic/therapeutic agent for diseases including osteoporosis, rheumatism and Alzheimer's disease, immunosuppressive agent, inhibitor for diseases including apoptosis, carcino metastasis and cataractogenesis, or the like. SOLUTION: This new compound is a compound of formula I [R1 is a lower alkyl; Y is a lower alkylene; R2 is OH, a (substituted) aryl or aryl-lower alkoxy; Z is O, imino or a group of formula II; R3 is H, a lower alkyl, pyridyl, a group of formula III (m is 1-6) or the like; n is 1-3; the asterisked C denotes C with R-configuration, C with S-configuration or the like], e.g. (R)-3-(trans-4- isopropylcyclohexylcarbonylamino)-2-oxo-4-phenylbutyric acid ethyl ester. The compound of formula I is obtained by oxidation of a compound of formula IV in one of various solvents (e.g. methylene chloride) in the presence of an oxidizing agent (e.g. sodium hypochlorite, pyridinium dichromate) pref. at room temperature to 50 deg.C for one hour to one day.