3-AZABICYCLOHEXANE COMPOUND INTERMEDIATES FOR PRODUCING ANTIBACTERIAL COMPOUNDS

• Main Author: BRIGHTY, KATHERINE E
• Format: Patent
• Language: English; French
• Published: 28.07.1998
• Edition: 6
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; 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

Disclosed are 3-azabicyclohexane compounds of the formula: (wherein Y2 is hydrogen, benzyl or benzyloxycarbonyl; R is R15 or R19; R' is hydrogen or R18, with the proviso that R' is R18 when R is R19 and R' is hydrogen when R is R15; R15 is carboxyl, hydroxymethyl, CHO, CH2NR11R12 or NR11R12 wherein R11 is hydrogen, methyl, or ethyl, and R12 is hydrogen, C1-C6 acyl, C2-C6 alkoxycarbonyl, optionally substituted benzyloxycarbonyl, aryloxycarbonyl, silyl, trityl, tetrahydropyranyl, vinyloxycarbonyl, O-nitrophenylsulfonyl, diphenylphosphonyl, p-toluenesulfonyl, or benzyl; R18 is methyl, cyano, hydroxymethyl, or CH2NR11R12; and R19 is methyl, carboxyl, hydroxymethyl, CHO, hydroxymethyl, tetrahydropyranyl ether, CH2NR11R12, or NR11R12, wherein R11 is hydrogen, methyl or ethyl and R12 is hydrogen, C1-C6 acyl, C2-C6 alkoxycarbonyl, optionally substituted benzyloxycarbonyl, aryloxycarbonyl, silyl, trityl, tetrahydropyranyl, vinyloxycarbonyl, O-nitrophenylsulfonyl, diphenylphosphonyl, p-toluenesulfonyl, or benzyl) which are useful as intermediates for producing antibacterial compounds of the formula: (wherein R1 is H or alkyl; Y is alkyl, cyclopropyl or substituted phenyl; W is H, halo, alkyl, alkoxy, NH2 or NHCH3; A is CH, CF, CC1, COCH3, CCH3, CCN or N; or A is C forming a ring with Y; and R2 means a group formed by removing Y2 from the 3-azabicyclohexane compound of the above formula, among others).