INDOLE DERIVATIVES

摘要

1391005 1,3,4,9 - Tetrahydro - (pyrano or thiopyrano) [3,4-6] indole derivatives AMERICAN HOME PRODUCTS CORP 1 June 1972 [1 June 1971] 25605/72 Heading C2C Novel compounds I in which R 1 is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl, phenyl, benzyl or 2- thienyl, R 2 , R 3 B 4 and B 5 are hydrogen or C 1-6 alkyl, R 7 is hydrogen, C 1-6 alkyl or C 2-6 alkenyl, X is oxygen or sulphur, Y is -CO-, or. (in which R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are hydrogen or C 1-6 alkyl), Z is hydroxy, C 1-4 alkoxy amino, mono- or di- (C 1-6 alkyl) amino or phenylamino and R 6 is hydrogen, C 1-6 alkyl, hydroxy, C 1-4 alkoxy, benzyloxy, C 2-6 alkanoyloxy nitro or halogen or R 6 is one to four substituents selected from halogen, C 1-6 alkyl, hydroxy, C 1-4 alkoxy benzyloxy, C 2-6 alkanyloxy, nitro, mercapto, C 1-6 alkylthio, halo C 1-6 (preferably trifluoromethyl) amino or;sulphamoyl and their addition salts are prepared by reacting a compound II in which X1 is hydroxy or mercapto with a compound R 1 -CO-Y-Z in the presence of an acid catalyst. Compounds I in which Z is hydroxy are also prepared by reacting compound II with a compound in which Y1 is CH 2 , -CR 8 C 9 -CH 2 -, or -CR 8 R 9 -CR 10 R 11 -CR 12 R 13 -CH 2 and R 17 is hydrogen or C 1-6 alkyl to form a compound IX which is hydrolysed to the corresponding primary alcohol which is oxidized to the aldehyde and then to the acid. Amide derivatives of Formula I are also prepared from the acids (Z is OH) by reaction with the ethylchloroformate and the appropriate amine or from the ester (Z is C 1-6 alkyl) by treatment with the amine. Compounds I in which R 7 is C 1-6 alkyl or C 2-6 alkenyl are also prepared by N-alkylation of compounds I in which R 7 is hydrogen. Compounds I show anti-inflammatory, analgesic, anti-bacterial and anti-fungal activity and form with a carrier a pharmaceutical composition which may be administered orally or parenterally or topically. Compounds I are also utilized in disinfectant and antiseptic wash solutions.