This invention is concerned with novel and pharmaceutically active indole derivatives having the structure: ##SPC1## And the salts thereof with physiologically acceptable acids, in which Each of X and Y is selected from the group consisting of hydrogen, hydroxy, lower alkyl having 1-3 carbon atoms and lower alkoxy having 1-3 carbon atoms, R.sup.1 is selected from the group consisting of hydrogen, lower alkyl having 1-4 carbon atoms and benzyl, R.sup.2 is selected from the group consisting of hydrogen, lower alkyl having 1-4 carbon atoms, benzyl and phenyl, R.sup.3 is selected from the group consisting of hydrogen, lower alkyl having 1-8 carbon atoms, cycloalkyl having 5 or 6 carbon atoms, benzyl and 2-phenylethyl, and A is a straight or branched alkylene chain containing from 2 to 4 carbon atoms.
This application is a continuation-in-part of co-pending applications Ser. No. 39,863 filed May 22, 1970 (now abandoned), Ser. No. 201,550 filed May 20, 1970 and Ser. No. 287,311 filed Sept. 8, 1972.
Indole derivatives of formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may be hydrogen or lower alkyl optionally substituted by halogen; X represents oxygen or sulfur; A.sup.1 represents a straight or branched alkylene chain containing from 2 to 4 carbon atoms; R.sup.5 is hydrogen or a straight or branched alkyl group; A.sup.2 is a straight or branched, saturated or unsaturated hydrocarbon chain containing from 2 to 6 carbon atoms; and R.sup.6 is selected from a group consisting of various structures, have been found to exhibit central nervous system activities.
Compounds of formula (I) or a salt thereof: ##STR1## R.sup.1 is hydrogen, halogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, COC.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy, hydroxyC.sub.1-6 alkyl, hydroxyC.sub.1-6 alkoxy, C.sub.1-6 alkoxyC.sub.1-6 alkoxy, acyl, nitro, trifluoromethyl, cyano, CHO, SR.sup.9, SOR.sup.9, SO.sub.2 R.sup.9, SO.sub.2 NR.sup.10 R.sup.11, CO.sub.2 R.sup.10, NR.sup.10 SO.sub.2 R.sup.11, CONR.sup.10 R.sup.11, CO.sub.2 NR.sup.10 R.sup.11, CONR.sup.10 (CH.sub.2).sub.p CO.sub.2 R.sup.11, (CH.sub.2).sub.p NR.sup.10 R.sup.11, (CH.sub.2).sub.p CONR.sup.10 R.sup.11, (CH.sub.2).sub.p NR.sup.10 COR.sup.11, (CH.sub.2).sub.p CO.sub.2 C.sub.1-6 alkyl, CO.sub.2 (CH.sub.2).sub.p OR.sup.10, CONHNR.sup.10 R.sup.11, NR.sup.10 R.sup.11, NR.sup.10 CO.sub.2 R.sup.11, NR.sup.10 CONR.sup.10 R.sup.11, CR.sup.10 .dbd.NOR.sup.11, CNR.sup.10 .dbd.NOR.sup.11, where R.sup.10 and R.sup.11 are independently hydrogen or C.sub.1-6 alkyl and p is 1 to 4; R.sup.2 and R.sup.3 are independently hydrogen, halogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkenyl, C.sub.1-6 alkoxy, acyl, aryl, acyloxy, hydroxy, nitro, trifluoromethyl, cyano, hydroxyC.sub.1-6 alkyl, C.sub.1-6 alkylOC.sub.1-6 alkyl, CO.sub.2 R.sup.10, CONR.sup.10 R.sup.11, NR.sup.10 R.sup.11 where R.sup.10 and R.sup.11 are independently hydrogen or C.sub.1-6 alkyl; R.sup.4 and R.sup.5 are independently hydrogen or C.sub.1-6 alkyl; R.sup.6 is hydrogen, halogen, hydroxy, C.sub.1-6 alkyl or C.sub.1-6 alkoxy; R.sup.7 and R.sup.8 are independently hydrogen, C.sub.1-6 alkyl, aralkyl, or together with the nitrogen atom to which they are attached form an optionally substituted 5-7-membered heterocyclic ring containing one or two heteroatoms selected from oxygen, nitrogen or sulphur; A is oxygen, S(O).sub.q where q is 0, 1 or 2, CR.sup.4 .dbd.CR.sup.5 or CR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are independently hydrogen or C.sub.1-6 alkyl, or A is NR.sup.12 where R.sup.12 is hydrogen or C.sub.1-6 alkyl; B is (CR.sup.13 R.sup.14).sub.q where q is 2, 3 or 4 and R.sup.13 and R.sup.14 are independently hydrogen or C.sub.1-6 alkyl or B is (CR.sup.13 R.sup.14).sub.r --D where r is 0, 1, 2 or 3 and D is oxygen, sulphur or CR.sup.13 .dbd.CR.sup.14 ; m is 1 to 4; and n is 1 or 2, exhibit 5HT.sub.1D antagonist activity.
2-oxyindole derivatives represented by the following general formula: ##STR1## where R.sub.1 is selected from the group consisting of hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, benzyl and phenethyl; A is --CH.dbd.CH-- or ##STR2## wherein R.sub.2 or R.sub.3 may be the same or different and are selected from the group consisting of hydrogen and C.sub.1-4 alkyl; R.sub.6 and R.sub.7 may be the same or different and are selected from the group consisting of hydrogen, C.sub.1-4 alkyl, benzyl, phenethyl and together with the nitrogen atom, a heterocyclic group selected from the group consisting of a piperidino, morpholino, piperazino or thiazolino group; and m and n each are zero or a positive integer with m+n being no more than 11. The 2-oxyindole derivatives have excellent effects on the inhibition of platelet aggregation.
