GB1306230A - - Google Patents

Abstract

1306230 Indole derivatives NOOV TERAPEUTISK LABORATORIUM AS 14 May 1970 26683/69 Heading C2C Novel compounds of Formula I and salts in which the benzene ring may carry one or more substituents each selected from lower alkyl radicals containing from 1 to 3 carbon atoms, halogen atoms, OR<SP>5</SP> in which R<SP>5</SP> represents a hydrogen atom, a lower alkyl radical containing from 1 to 3 carbon atoms, or a benzyl radical, and -NHCOCH 3 , R<SP>1</SP> represents a hydrogen atom, a lower alkyl radical containing from 1 to 6 carbon atoms, optionally substituted by a phenyl or substituted phenyl radical or a cycloalkyl radical containing from 5 to 7 carbon atoms, a lower alkanoyl radical containing from 2 to 4 carbon atoms, or a benzoyl or substituted benzoyl radical, R<SP>2</SP> represents a hydrogen atom, a lower alkyl radical containing from 1 to 4 carbon atoms, or a benzyl or phenyl radical, each of R<SP>3</SP> and R<SP>4</SP> represents a hydrogen atom, a lower alkyl radical containing from 1 to 6 carbon atoms, a cyclo-alkyl radical containing from 5 to 7 carbon atoms, or a benzyl radical in which the phenyl moiety may be substituted, or R<SP>3</SP> and R<SP>4</SP> together with the attached nitrogen atom represent a heterocyclic ring, and A represents a straight or branched alkylene radical containing from 2 to 4 carbon atoms, with the proviso that one or both of the substituents R<SP>3</SP> and R<SP>4</SP> cannot represent hydrogen when the benzene ring in Formula I carries a halogen and/or benzyloxy substituent or when R<SP>1</SP> represents an acyl radical, are prepared by one of the following methods: (a) reacting a compound of Formula III with a compound X<SP>1</SP>-A-N(R 3 )R 4 where X<SP>1</SP> is halogen or a functionally equivalent group, (b) hydrolysing and decarboxylating a compound of Formula V simultaneously acylating it in the 1-position, (c) by hydrolysis of a compound of Formula I above wherein R<SP>1</SP> is acyl to give the compound where R<SP>1</SP> is H, (d) reaction of a compound of Formula I where R<SP>1</SP> is H and R<SP>3</SP>, R<SP>4</SP> and R<SP>5</SP> are not H with a compound R<SP>1</SP>X<SP>1</SP>, (e) conversion of one of the -N(R 3 )R 4 groups into another by standard means, or (f) reductively alkylating an amine HN(R 3 )R 4 with an indole of formula and optionally in all cases forming or converting a salt. 5-Acetamido-1-acetylindoxyl is prepared by action of sodium sulphite in aqueous ethanol on 5-acetamido-1,3-diacetylindoxyl obtained by reduction of 1,3-diacetyl-5-nitroindoxyl in acetic anhydride by hydrogenation using Raney nickel. 3-(Acetonyloxy)-1-acetylindole is prepared reacting 1-acetylindoxyl with chloro-2-propanone. Pharmacological preparations having analgesic, anti-inflammatory, sedative or stimulant activity, comprise as active ingredient a compound of Formula I above.