DE35259T1 - Tetrahydrothiopyrano (3,2-b) indole derivatives, processes for their preparation and pharmaceutical compositions containing these compounds - Google Patents

Claims (7)

Claims 1
in which R is a hydrogen atom, a C., - alkyl, C _? _, - alkenyl, C ~ _, - alkynyl, C _7-1 "-aralkyl- or C" _. -Acyl radical, or the remainder 5 -Y-N represents in which Y is a C ₁ alkylene or C _.- _{1-.-Oxoalkylenrest} and R and R are each a hydrogen atom or a C ₁ _, - mean alkyl; R represents a hydrogen atom or a C ₁ , -alkyl radical; R is a hydrogen atom or a C ₁ _ _f -alkyl radical or the radical -Y-N represents, in which Y, R and R have the meanings given above;
or , R -N ' a pyrrolidino, piperidinyl or piperazinyl group, ,;, a 4-e-alkylpiperazinyl radical or a morpholino group ; ■; .. means; R denotes a hydrogen atom or a C., alkyl radical and η has the value 0, 1 or 2 and their pharmaceutically acceptable salts. 2. A compound according to claim 1, in which the C _7-12 aralkyl radical is a phenyl-C, ._, - alkyl radical. 3. A compound according to claim 1, in which the C,.,. -Acyl radical represents a radical R CO, in which R is a C, ^ -alkyl radical, represents a phenyl group or a substituted phenyl group. 4. A compound according to claim 1, in which R is hydrogen means. 4 5. A compound according to claim 1, in which R is a methyl group. 6. A compound according to claim 1, in which η is zero. 7. A compound according to claim 1, in which η is 1. 8. A compound according to claim 4, in which R is a hydrogen atom or a C._ _fi -alkyl radical. 9. A compound according to claim 8, in which R represents a methyl group. 10. A compound according to claim 8, in which R is a hydrogen atom and R is a C 1, - alkyl radical. I -D ³ "003575-9 2 ■ 11. A compound according to claim 8, in which R is a Cj_g alkyl rest and R. a N, N-Di-C -alkylaminoäthylrest meaning J I * - υ ten .: 12. A compound according to claim 8, in which R and R each represent a C ₁ -alkyl radical. I - D 13. A compound according to claim 10, in which R is methyl means.
10 14. A compound according to claim 11, in which R is methyl and R is a Ν, Ν-diethylaminoethyl group. 2 3 15. A compound according to claim 12, in which R and R are each one Mean methyl group. 16. The compound of claim 1 which is 4-methylaminomethyl-5-methyl-2,3,4,5-tetrahydrothiopyrano [3 , 2-b] indole. ' 17. A compound according to claim 1, namely 4-methylaminomethyl 5-ethyl-2,3,4,5-tetrahydrothiopyrano [3,2-b] indole. 18. Compound according to claim 1, namely 4-dimethylaminomethyl 5-methyl-2,3,4,5-tetrahydrothiopyrano [3,2-b] indole. 25th 19. The compound of claim 1 which is 4-methylaminomethyl-5-methyl-2,3,4,5-tetrahydrothiopyrano [3,2-b] indole-1-oxide. 20. The compound of claim 1 which is 4-methylaminomethyl-30 5-allyl-2,3,4,5-tetrahydrothiopyrano [3,2-b] indole. 21. A compound according to claim 1, namely 4-N-methyl-N- (N, N-diethylaminoethyl) aminomethyl-S-methyl ^, 3,4,5-tetrahydrothiopyrano 13,2-b] indole. L J 22. Process for the preparation of a compound of the general Formula I. 10 20th (D 12 3 4
in which R, R, R, R and η are the above have a meaning
* characterized in that one (a) a compound of the general formula II 15 Hu) R ¹ ..CHO in which R has the meaning given above, a reaction with ammonia or a primary or secondary amine under reductive conditions or subject to a subsequent reduction, if necessary. (b) a compound of the general formula I in which R. represents a hydrogen atom, a reaction to introduce a substituent at the 5-position subject, (c) Subjecting a compound of the general formula I in which η has the value O to an oxidation with a peracid, the corresponding oxide or dioxide being obtained and
(d) a compound of the general formula I for modifying its substituents of a corresponding one Reaction subjects. U -J ^Γ - 5 - 23. Medicaments containing at least one compound according to claims 1 to 21 and pharmaceutically acceptable Carrier.