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Claims for Patent: 4,843,086

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Claims for Patent: 4,843,086

Title: Tetrahydro-benzthiazoles, the preparation thereof and their use as intermediate products or as pharmaceuticals
Abstract:This invention relates to new tetrahydrobenzthiazoles of general formula ##STR1## wherein R.sub.1 represents a hydrogen atom, an alkyl group, an alkenyl or alkynyl group, an alkanoyl group, a phenyl alkyl or phenyl alkanoyl group, while the above mentioned phenyl nuclei may each be substituted by 1 or 2 halogen atoms. R.sub.2 represents a hydrogen atom or an alkyl group, R.sub.3 represents a hydrogen atom, an alkyl group a cycloalkyl group, an alkenyl or alkynyl group, an alkanoyl group, a phenyl alkyl or phenyl alkanoyl group, while the phenyl nucleus may be substituted by fluorine, chlorine or bromine atoms, R.sub.4 represents a hydrogen atom, an alkyl group, an alkyl or alkenyl group, or R.sub.3 and R.sub.4 together with the nitrogen atom between them represent a pyrrolidino, piperidino, hexamethyleneimino or morpholino group, the enantiomers and the acid addition salts thereof. The compounds of general formula I above in which one of the groups R.sub.1 or R.sub.3 or both groups R.sub.1 and R.sub.3 represent an acyl group are valuable intermediate products for preparing the other compounds of general formula I which have valuable pharmacological properties. The new compounds may be prepared using methods known per se.
Inventor(s): Griss, deceased; Gerhart (late of Biberach, DE), Schneider; Claus (Ingelheim am Rhein, DE), Hurnaus; Rudolf (Biberach, DE), Kobinger; Walter (Vienna, AT), Pichler; Ludwig (Vienna, AT), Bauer; Rudolf (Wiesbaden, DE), Mierau; Joachim (Mainz, DE), Hinzen; Dieter (Zornheim, DE), Schingnitz; Gunter (Bad Kreuznach, DE)
Assignee: Boehringer Ingelheim KG (Ingelheim am Rhein, DE)
Application Number:07/124,197
Patent Claims: 1. A method for lowering the blood pressure of a host which comprises administering a blood pressure lowering amount of a tetrahydro-benzthiazole of the formula: ##STR15## wherein R.sub.1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl or alkynyl group each having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, wherein the above mentioned phenyl nucleus may be substituted by 1 or 2 halogen atoms;

R.sub.2 is a hydrogen atom or an alkyl group with 1 to 4 carbon atoms;

R.sub.3 is a hydrogen atom, an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, whilst the phenyl nucleus may be substituted by fluorine, chlorine or bromine atoms; and,

R.sub.4 is a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms; or,

R.sub.3 and R.sub.4 together with the nitrogen atom between them form a pyrrolidino, piperidino, hexamethyleneimino or morpholino group; or, a pharmaceutically acceptable acid addition salt thereof.

2. The method of claim 1 wherein the group --NR.sub.3 R.sub.4 is in the 5- or 6-positions.

3. A method for lowering the blood pressure of a host which comprises administering a blood pressure lowering amount of a tetrahydro-benzthiazole of the formula: ##STR16## wherein R.sub.1 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an allyl, benzyl, 2-chloro-benzyl, 4-chloro-benzyl, 3,4-dichloro-benzyl or phenylethyl group;

R.sub.2 is a hydrogen atom, a methyl or ethyl group;

R.sub.3 is a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an allyl, propargyl, benzyl, chlorobenzyl, phenylethyl, cyclopentyl or cyclohexyl group; and,

R.sub.4 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or an allyl group; or,

R.sub.3 and R.sub.4 together with the nitrogen atom between them form a pyrrolidino, piperidino, hexamethyleneimino or morpholino group; or, a pharmaceutically acceptable acid addition salt thereof.

4. The method of claim 3 wherein the group --NR.sub.3 R.sub.4 is in the 6-position.

5. The method of claim 3 wherein,

R.sub.1 and R.sub.2 together with the nitrogen atom between them form an amino or allylamino group; and,

R.sub.3 and R.sub.4 together with the nitrogen atom between them form a dimethylamino, diethylamino, N-allyl-N-(4-chloro-benzyl)-amino, n-propylamino or pyrrolidino group.

6. A method for lowering the blood pressure of a host which comprises administering a blood pressure lowering amount of a compound of the formula: ##STR17## wherein R is a hydrogen atom, an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, whilst the phenyl nucleus may be substituted by fluorine, chlorine or bromine atoms; or, a pharmaceutically acceptable acid addition salt thereof.

7. The method of claim 6 wherein R is a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an allyl, propargyl, benzyl, chlorobenzyl, phenethyl, cyclopentyl, or cyclohexyl group.

8. The method of claim 7 wherein R is an alkyl group with 1 to 6 carbon atoms.

9. A method for lowering the blood pressure of a host which comprises administering a blood pressure lowering amount of 2-Amino-6-n-propylamino-4,5,6,7-tetrahydrobenzthiazole, or a pharmaceutically acceptable acid addition salt thereof.

10. A method for lowering the blood pressure of a host which comprises administering a blood pressure lowering amount of 2-Amino-6-n-dimethylamino-4,5,6,7-tetrahydrobenzthiazole, or a pharmaceutically acceptable acid addition salt thereof.

11. A method for lowering the heart rate of a host which comprises administering a heart rate lowering amount of a tetrahydro-benzthiazole of the formula: ##STR18## wherein R.sub.1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl or alkynyl group each having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, wherein the above mentioned phenyl nucleus may be substituted by 1 or 2 halogen atoms;

R.sub.2 is a hydrogen atom or an alkyl group with 1 to 4 carbon atoms;

R.sub.3 is a hydrogen atom, an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, whilst the phenyl nucleus may be substituted by fluorine, chlorine or bromine atoms; and,

R.sub.4 is a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, an alkenyl or alkynyl group having 3 to 6 atoms; or,

R.sub.3 and R.sub.4 together with the nitrogen atom between them form a pyrrolidino, piperidino, hexamethyleneimino or morpholino group; or, a pharmaceutically acceptable acid addition salt thereof.

12. The method of claim 11 wherein the group --NR.sub.3 R.sub.4 is in the 5- or 6-positions.

13. A method for lowering the heart rate of a host which comprises administering a heart rate lowering amount of a tetrahydro-benzthiazole of the formula: ##STR19## wherein R.sub.1 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an allyl, benzyl, 2-chloro-benzyl, 4-chloro-benzyl, 3,4-dichloro-benzyl or phenylethyl group;

R.sub.2 is a hydrogen atom, a methyl or ethyl group;

R.sub.3 is a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an allyl, propargyl, benzyl, chlorobenzyl, phenylethyl, cyclopentyl or cyclohexyl group; and,

R.sub.4 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or an allyl group; or,

R.sub.3 and R.sub.4 together with the nitrogen atom between them form a pyrrolidino, piperidino, hexamethyleneimino or morpholino group; or, a pharmaceutically acid addition salt thereof.

14. The method of claim 13 wherein the group --NR.sub.3 R.sub.4 is in the 6-position.

15. The method of claim 13 wherein,

R.sub.1 and R.sub.2 together with the nitrogen atom between them form an amino or allylamino group; and,

R.sub.3 and R.sub.4 together with the nitrogen atom between them form a dimethylamino, diethylamino, N-allyl-N-(4-chloro-benzyl)-amino, n- propylamino or pyrrolidino group.

16. A method for lowering the heart rate of a host which comprises administering a heart rate lowering amount of a compound of the formula: ##STR20## wherein R is a hydrogen atom, an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, whilst the phenyl nucleus may be substituted by fluorine, chlorine or bromine atoms; or, a pharmaceutically acceptable acid addition salt thereof.

17. The method of claim 16 wherein R is a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an allyl, propargyl, benzyl, chlorobenzyl, phenethyl, cyclopentyl, or cyclohexyl group.

18. The method of claim 17 wherein R is an alkyl group with 1 to 6 carbon atoms.

19. A method for lowering the heart rate of a host which comprises administering a heart rate lowering amount of 2-Amino-6-n-propylamino-4,5,6,7-tetrahydro-benzthiazole, or a pharmaceutically acceptable acid addition salt thereof.

20. A method for lowering the heart rate of a host which comprises administering a heart rate lowering amount of 2-Amino-6-dimethylamino-4,5,6,7-tetrahydro-benzthiazole, or a pharmaceutically acceptable acid addition salt thereof.

21. A method for treating Parkinsonism or Parkinson's disease which comprises administering a therapeutically effective amount of a tetrahydro-benzthiazole of the formula: ##STR21## wherein R.sub.1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl or alkynyl group each having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, wherein the above mentioned phenyl nucleus may be substituted by 1 or 2 halogen atoms;

R.sub.2 is a hydrogen atom, an alkyl group with 1 to 4 carbon atoms;

R.sub.3 is a hydrogen tom, an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, whilst the phenyl nucleus may be substituted by fluorine, chlorine or bromine atoms; and,

R.sub.4 is a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms; or,

R.sub.3 and R.sub.4 together with the nitrogen atom between them form a piperidino, hexamethyleneimino or morpholino group; or, a pharmaceutically acceptable acid addition salt thereof.

22. The method of claim 21 wherein the group --NR.sub.3 R.sub.4 is in the 5- or 6-positions.

23. A method for treating Parkinsonism or Parkinson's disease which comprises administering a therapeutically effective amount of a tetrahydro-benzthiazole of the formula: ##STR22## wherein R.sub.1 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, an allyl, benzyl, 2-chloro-benzyl, 4-chloro-benzyl, 3,4-dichloro-benzyl or phenylethyl group;

R.sub.2 is a hydrogen atom, a methyl or ethyl group;

R.sub.3 is a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an allyl, propargyl, benzyl, chlorobenzyl, phenylethyl, cyclopentyl or cyclohexyl group; and,

R.sub.4 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or an allyl group; or,

R.sub.3 and R.sub.4 together with the nitrogen atom between them for a piperidino, hexamethyleneimino or morpholino group; or, a pharmaceutically acceptable acid addition salt thereof.

24. The method of claim 21 wherein the group --NR.sub.3 R.sub.4 is in the 6-position.

25. The method of claim 21 wherein,

R.sub.1 and R.sub.2 together with the nitrogen atom between them form an amino or allylamino group; and,

R.sub.3 and R.sub.4 together with the nitrogen atom between them form a dimethylamino, diethylamino, N-allyl-N-(4-chloro-benzyl)-amino, or n- propylamino group.

26. A method for treating Parkinsonism or Parkinson's disease which comprises administering a therapeutically effective amount of a compound of the formula: ##STR23## wherein R is a hydrogen atom, an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, whilst the phenyl nucleus may be substituted by fluorine, chlorine or bromine atoms; or, a pharmaceutically acceptable acid addition salt thereof.

27. The method of claim 26 wherein R is a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an allyl, propargyl, benzyl, chlorobenzyl, phenethyl, cyclopentyl, or cyclohexyl group.

28. The method of claim 27 wherein R is an alkyl group with 1 to 6 carbon atoms.

29. A method for treating Parkinsonism or Parkinson's disease which comprises administering a therapeutically effective amount of 2-Amino-6-n-propylamino-4,5,6,7-tetrahydro-benzthiazole, or a pharmaceutically acceptable acid addition salt thereof.

30. A method for treating Parkinsonism or Parkinson's disease which comprises administering a therapeutically effective amount of 2-Amino-6-dimethylamino-4,5,6,7-tetrahydro-benzthiazole, or a pharmaceutically acceptable acid addition salt thereof.

31. A method for treating schizophrenia which comprises administering a therapeutically effective amount of a tetrahydro-benzthiazole of the formula: ##STR24## wherein R.sub.1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl or alkynyl group each having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, wherein the above mentioned phenyl nucleus may be substituted by 1 to 2 halogen atoms;

R.sub.2 is a hydrogen atom or an alkyl group with 1 to 4 carbon atoms;

R.sub.3 is a hydrogen atoms, an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, whilst the phenyl nucleus may be substituted by fluorine, chlorine or bromine atoms; and,

R.sub.4 is a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms; or,

R.sub.3 and R.sub.4 together with the nitrogen atom between them form a pyrrolidino, piperidino, hexamethyleneimino or morpholino group; or, a pharmaceutically acceptable addition salt thereof.

32. The method of claim 31 wherein the group --NR.sub.3 R.sub.4 is in the 5- or 6-position.

33. A method for treating schizophrenia which comprises administering a therapeutically effective amount of a tetrahydro-benzthiazole of the formula: ##STR25## wherein R.sub.1 is a hydrogen atom an alkyl group having 1 to 3 carbon atoms, an allyl, benzyl, 2-chloro-benzyl, 4-chloro-benzyl, 3,4-dichloro-benzyl or phenylethyl group;

R.sub.2 is a hydrogen atom, a methyl or ethyl group;

R.sub.3 is a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an allyl, propargyl, benzyl, chlorobenzyl, phenylethyl, cyclopentyl or cyclohexyl group; and,

R.sub.4 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or an allyl group; or,

R.sub.3 and R.sub.4 together with the nitrogen atom between them form a pyrrolidino, piperidino, hexamethyleneimino or morpholino group; or, a pharmaceutically acceptable acid addition salt thereof.

34. The method of claim 33 wherein the group --NR.sub.3 R.sub.4 is in the 6-position.

35. The method of claim 33 wherein

R.sub.1 and R.sub.2 together with the nitrogen atom between them form an amino or allylamino group; and,

R.sub.3 and R.sub.4 together with the nitrogen atom between them form a dimethylamino, diethylamino, N-allyl-N-(4-chloro-benzyl)-amino, n- propylamino or pyrrolidino group.

36. A method for treating schizophrenia which comprises administer a therapeutically effective amount of a compound of the formula: ##STR26## wherein R is a hydrogen atom, an alkyl group with 1 to 7 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an alkenyl or alkynyl group having 3 to 6 carbon atoms, a phenyl alkyl group having 1 to 3 carbon atoms in the alkyl part, whilst the phenyl nucleus may be substituted by fluorine, chlorine or bromine atoms; or, a pharmaceutically acceptable acid addition salt thereof.

37. The method of claim 36 wherein R is a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, an allyl, propargyl, benzyl, chlorobenzyl, phenethyl, cyclopentyl, or cyclohexyl group.

38. The method of claim 37 wherein R is an alkyl group with 1 to 6 carbon atoms.

39. A method for treating schizophrenia which comprises administering a therapeutically effective amount of 2-Amino-6-n-propylamino-4,5,6,7-tetrahydro-benzthiazole, or a pharmaceutically acceptable acid addition salt thereof.

40. A method for treating schizophrenia which comprises administering a therapeutically effective amount of 2-Amino-6-dimethylamino-4,5,6,7-tetrahydro-benzthiazole, or a pharmaceutically acceptable acid addition salt thereof.
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