Patent GB-1368809-A (GB)
Title: O-esters of hexafuranoses and a process for their manufacture
IPC: C07H15/04
Filed: 1971-10-29
Abstract: 1368809 0-esters of hexafuranoses CIBAGEIGY AG 29 Oct 1971 [13 Nov 1970 20 July 1971] 50374/71 Heading C2C Novel compounds I and the salts thereof in which R A  is hydrogen or OR 6  and at least one of the symbols R 1  to R 6  is an acyl radical (II) in which Ar<SP>1</SP> is a phenyl radical optionally substituted by one or more substituents selected from cycloalkyl, cycloalkenyl, aryl, aryl-C 1-7  alkyl, cyoloalkyl-C 1-7  alkyl, C 1-7  alkoxy, C 2-7  alkenyloxy, C 1-7  alkylmercapto, phenoxy, phenylmercapto, halogen, trifluoromethyl, nitrile, nitro hydroxyl, mercapto, C 1-7  alkylamino, di- (C 1-7  alkyl)-amino, C 2-7  alkyleneamino (in which the carbon chain may be interrupted by one or more oxygen sulphur or nitrogen atoms; the nitrogen atoms themselves optionally being substituted by one or more C 1-7  alkyl or C 1-7  alkanoyl groups), C 2-7  alkenylene amino, C 1-7  alkanoylamino, carbamoyl N-C 1-7  alkylcarbamoyl, N,N - di - (C 1-7  alkyl) carbamoyl sulphamonyl, N-C 1-7  alkylsulphamoyl, N,N-di-(C 1-7  alkyl)sulphamoyl, C 1-7  alkylsulphonyl, C 1-7  alkylsulphenyl, benzoyl, 1,2,3,4-tetrahydroquinolinyl - (1), 1,2,3,4 - tetrahydroisoquinolinyl- (2)-, phenoxazinyl-(10), phenothiazinyl-(10), indolinyl - (1), 10,11 - dihydro - 5H - dibenz[6,f]- azepinyl - (5), #<SP>4</SP> - oxazolinyl - (3), #<SP>4</SP> - isoxazolinyl - (2), #<SP>4</SP> - thiazolinyl - (3), 2H - 1,2 - thiazinyl - (2), 3,4 -, 3,6- or 5,6 - dihydro - 2H -, 1, 2 - thiazinyl - (2), 2,3 - dihydro - 4H - 1,2- oxazinyl - (3), 4H - 1,4 - oxazinyl - (4), 2,3- dihydro - 1,4 - oxazinyl - (4), 2H - 1,2 - oxazinyl- (2), 5,6 - dihydro - 1,2 - oxazinyl - (2), pyrrolyl- (1), isoindolinyl - (2), 3,6 - dihydro - 2H - 1,2- oxazinyl - (2), 1 - oxo - isoindolinyl - (2), C 1-7  alkyl or C 2-7  alkenyl and in which two C 1-7  alkyl groups ortho to each other can form an alkylene or alkenylene group and the phenyl radical substituent of Ar<SP>1</SP> may itself be substituted by one or more substitutents selected from C 1-7  alkyl, C 1-7  alkoxy, trifluoromethyl and halogen, R and R<SP>1</SP> are hydrogen, C 1-7  alkyl, C 2-7  alkenyl, C 2-7  alkinyl, C 1-7  alkylidene, C 2-7  alkenylidene or C 2-7  alkinylidene, cycloalkyl or optionally substituted phenyl-C 1-7  alkyl or phenyl or R and R<SP>1</SP> together can denote C 1-7  alkylene or C 2-7  alkenylidene bonded to two adjacent C atoms of A<SP>1</SP> and A<SP>1</SP> is C 1-3  alkylene or alkenylene and of the remaining symbols R 1  is hydrogen or a C 1-7  alkyl, C 2-7  alkenyl, cycloalkyl, cycloalkyl-C 1-7  alkyl or phenyl-C 1-7  alkyl radical which radicals may be substituted, or the acyl radical of a C 1-7  alkane mono- or di-carboxylic C 2-7  alkene mono- or di-carboxylic acid and each R 2 , R 3 , R 5  and R 6  is hydrogen or C 1-7  alkyl, C 2-7  alkenyl, phenyl-C 1-7  alkyl, cycloalkyl or cycloalkyl-C 1-7  alkyl radicals which radicals may be substituted or the acyl radical of a C 1-7  alkane mono or dicarboxylic or C 2-7  alkene mono- or di-carboxylic acid with the proviso that if only R 2  represents a group II then this radical is not the acyl radical or a phenyl-, C 1-7  alkoxyphenyl-, C 1-7  alkylphenyl-, trifluoromethylphenyl-, or halogenophenyl-aliphatic carboxylic acid, are prepared by esterifying a free or reactive hydroxyl group with an acid derivative corresponding to the group II. More specifically Ar<SP>1</SP> is phenyl optionally substituted by phenyl, cyclohexyl or cyclohexenyl or by chloro and pyrrolinyl A<SP>1</SP> is methylene or vinylene, R is hydrogen, R<SP>1</SP> is methyl and the remaining groups R 2 , R 3 , R 5  and R 6  are C 1-7  alkyl or benzyl or p-chlorobenzyl. The hexanfuranose moiety is glucofuranose iodofuranose or 6-deoxy-glucofuranose. Compounds I are anti-inflammatory and analgesic agents and form with a carrier a pharmaceutical composition which may be administered orally, parenterally or topically.