Claims
- 1. A compound of the formula ##STR82## wherein --- indicates the presence of a single or double bond; HET is selected from the group consisting of ##STR83## R is hydrogen, alkyl, alkenyl, cycloalkylalkyl, arylalkyl, ##STR84## in which R.sup.2 is alkyl or arylalkyl; R.sup.1 is hydrogen, alkyl, or NR.sup.3 R.sup.4 in which R.sup.3 is hydrogen or alkyl and R.sup.4 is hydrogen, alkyl, alkenyl, cycloalkylalkyl, arylalkyl, ##STR85## n=0, 1 or 2; and corresponding geometric and optical isomers thereof; or a pharmaceutically acceptable acid addition salt thereof.
- 2. A compound according to claim 1, in which R and R.sup.4 are each independently hydrogen, alkyl, alkenyl, cycloalkylalkyl, ##STR86## or phenylalkyl in which phenyl is substituted by one to four substituents selected from alkyl, alkoxy, halogen or trifluoromethyl or a pharmaceutically acceptable acid addition salt thereof.
- 3. A compound according to claim 2, wherein R is hydrogen, alkyl, alkenyl, cyclopropylmethyl, ##STR87## benzyl or phenylethyl and R.sup.1 is hydrogen or NR.sup.3 R.sup.4 in which R.sup.3 is hydrogen or alkyl and R.sup.4 is hydrogen, alkyl, benzyl, ##STR88## in which R.sup.2 is alkyl or arylalkyl, or a pharmaceutically acceptable acid addition salt thereof.
- 4. A compound according to claim 3, wherein R is hydrogen, methyl, ethyl, allyl, n-propyl, n-butyl, cyclopropylmethyl, ##STR89## benzyl or phenylethyl and R.sup.1 is hydrogen or NR.sup.3 R.sup.4 in which R.sup.3 is hydrogen or alkyl and R.sup.4 is hydrogen, methyl, ethyl, n-propyl, ##STR90## in which R.sup.2 is alkyl or arylalkyl or a pharmaceutically acceptable acid addition salt thereof.
- 5. A compound according to claim 4, wherein R is hydrogen, methyl, ethyl, allyl, n-propyl, n-butyl, cyclopropylmethyl, benzyl or phenylethyl and R.sup.1 is hydrogen or NR.sup.3 R.sup.4 in which R.sup.3 is hydrogen and R.sup.4 is hydrogen, ##STR91## in which R.sup.2 is alkyl or arylalkyl or a pharmaceutically acceptable acid addition salt thereof.
- 6. A compound according to claim 5, and being (.+-.) 4,5,5a,6,7,8-hexahydro-6-propylthiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 7. A compound according to claim 5, and being (.+-.) trans-4,5,5a,6,7,8,9,9a-octahydrothiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 8. A compound according to claim 5, and being (.+-.) trans-4,5,5a,6,7,8,9,9a-octahydro-6-propylthiazolo[4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 9. A compound according to claim 5, and being (+) 4,5,5a,6,7,8-hexahydro-6-propylthiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 10. A compound according to claim 5, and being (-) 4,5,5a,6,7,8-hexahydro-6-propylthiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 11. A compound according to claim 5, and being (.+-.) 4,5,5a,6,7,8-hexahydrothiazolo[4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 12. A compound according to claim 5, and being (+) 4,5,5a,6,7,8-hexahydrothiazolo[4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 13. A compound according to claim 5, and being (-) 4,5,5a,6,7,8-hexahydrothiazolo[4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 14. A compound according to claim 5, and being (.+-.) 4,5,5a,6,7,8-hexahydro-6-methylthiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 15. A compound according to claim 5, and being (+) 4,5,5a,6,7,8-hexahydro-6-methylthiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 16. A compound according to claim 5, and being (-) 4,5,5a,6,7,8-hexahydro-6-methylthiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 17. A compound according to claim 5, and being (.+-.) 6-ethyl-4,5,5a,6,7,8-hexahydrothiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 18. A compound according to claim 5, and being (+) 6-ethyl-4,5,5a,6,7,8-hexahydrothiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 19. A compound according to claim 5, and being (-) 6-ethyl-4,5,5a,6,7,8-hexahydrothiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 20. A compound according to claim 5, and being (.+-.) 6-butyl-4,5,5a,6,7,8-hexahydrothiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 21. A compound according to claim 5, and being (+) 6-butyl-4,5,5a,6,7,8-hexahydrothiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 22. A compound according to claim 5, and being (-) 6-butyl-4,5,5a,6,7,8-hexahydrothiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 23. A compound according to claim 5, and being (.+-.) 4,5,5a,6,7,8-hexahydro-6-(2-propenyl) thiazolo[4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 24. A compound according to claim 5, and being (+) 4,5,5a,6,7,8-hexahydro-6-(2-propenyl) thiazolo[4,5-]f-quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 25. A compound according to claim 5, and being (-) 4,5,5a,6,7,8-hexahydro-6-(2-propenyl) thiazolo[4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 26. A compound according to claim 5, and being (.+-.) 6-(cyclopropylmethyl)-4,5,5a,6,7,8-hexahydrothiazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 27. A compound according to claim 5, and being (.+-.) 4,5,5a,6,7,8-hexahydro-6-(2-phenylethyl) thiazolo[4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 28. A compound according to claim 5, and being (+) 4,5,5a,6,7,8-hexahydro-6-(2-phenylethyl) thiazolo[4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 29. A compound according to claim 5, and being (.+-.) 4,5,5a,6,7,8-hexahydro-6-(phenylmethyl) thiazolo[4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 30. A compound according to claim 5, and being (.+-.) N-(4,5,5a,6,7,8-hexahydro-6-methylthiazolo [4,5-f]quinolin-2-yl)-2-methylpropanamide or a pharmaceutically acceptable acid addition salt thereof.
- 31. A compound according to claim 5, and being (+) N-(4,5,5a,6,7,8-hexahydro-6-methylthiazolo [4,5-f]quinolin-2-yl)-2-methylpropanamide or a pharmaceutically acceptable acid addition salt thereof.
- 32. A compound according to claim 5, and being (-) N-(4,5,5a,6,7,8-hexahydro-6-methylthiazolo [4,5-f]quinolin-2-yl)-2-methylpropanamide or a pharmaceutically acceptable acid addition salt thereof.
- 33. A compound according to claim 5, and being (.+-.) N-(4,5,5a,6,7,8-hexahydro-6-propylthiazolo [4,5-f]quinolin-2-yl)acetamide or a pharmaceutically acceptable acid addition salt thereof.
- 34. A compound according to claim 5, and being (.+-.) N-(4,5,5a,6,7,8-hexahydro-6-methylthiazolo [4,5-f]quinolin-2-yl)acetamide or a pharmaceutically acceptable acid addition salt thereof.
- 35. A compound according to claim 5, and being (+) N-(4,5,5a,6,7,8-hexahydro-6-methylthiazolc [4,5-f]quinolin-2-yl)acetamide or a pharmaceutically acceptable acid addition salt thereof.
- 36. A compound according to claim 5, and being (-) N-(4,5,5a,6,7,8-hexahydro-6-methylthiazolo [4,5-f]quinolin-2-yl)acetamide or a pharmaceutically acceptable acid addition salt thereof.
- 37. A compound according to claim 5, and being (+) N-(4,5,5a,6,7,8-hexahydro-6-propylthiazolo [4,5-f]quinolin-2-yl)acetamide or a pharmaceutically acceptable acid addition salt thereof.
- 38. A compound according to claim 5, and being (-) N-(4,5,5a,6,7,8-hexahydro-6-propylthiazolo [4,5-f]quinolin-2-yl)acetamide or a pharmaceutically acceptable acid addition salt thereof.
- 39. A compound according to claim 5, and being (.+-.) N-[4,5,5a,6,7,8-hexahydro-6-(2-propenyl) thiazolo[4,5-f]quinolin-2-yl]acetamide or a pharmaceutically acceptable acid addition salt thereof.
- 40. A compound according to claim 5, and being (+) N-[4,5,5a,6,7,8-hexahydro-6-(2-propenyl) thiazolo[4,5-f]quinolin-2-yl]acetamide or a pharmaceutically acceptable acid addition salt thereof.
- 41. A compound according to claim 5, and being (-) N-[4,5,5a,6,7,8-hexahydro-6-(2-propenyl) thiazolo[4,5-f]quinolin-2-yl]acetamide or a pharmaceutically acceptable acid addition salt thereof.
- 42. A compound according to claim 5, and being (.+-.) N-(4,5,5a,6,7,8-hexahydro-6-propylthiazolo [4,5-f]quinolin-2-yl)-2-methylpropanamide or a pharmaceutically acceptable acid addition salt thereof.
- 43. A compound according to claim 5, and being (+) N-(4,5,5a,6,7,8-hexahydro-6-propylthiazolo [4,5-f]quinolin-2-yl)-2-methylpropanamide or a pharmaceutically acceptable acid addition salt thereof.
- 44. A compound according to claim 5, and being (-) N-(4,5,5a,6,7,8-hexahydro-6-propylthiazolo [4,5-f]quinolin-2-yl)-2-methylpropanamide or a pharmaceutically acceptable acid addition salt thereof.
- 45. A compound according to claim 5, and being (.+-.) trans-4,5,5a,6,7,8,9,9a-octahydro-6-propylthiazolo[5,4-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 46. A compound according to claim 5, and being (+) trans-4,5,5a,6,7,8,9,9a-octahydro-6-propylthiazolo[5,4-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 47. A compound according to claim 5, and being (-) trans-4,5,5a,6,7,8,9,9a-octahydro-6-proylthioazolo[5,4-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 48. A compound according to claim 5, and being (.+-.) 4,5,5a,6,7,8-hexahydro-6-propylthiazolo [5,4-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 49. A compound according to claim 5, and being (.+-.) 4,5,5a,6,7,8-hexahydro-6-propyloxazolo [5,4-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 50. A compound according to claim 5, and being (.+-.) 4,5,5a,6,7,8-hexahydro-6-propyloxazolo [4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 51. A compound according to claim 5, and being (.+-.) trans-4,5,5a,6,7,8,9,9a-octahydro-6-propyloxazolo[4,5-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 52. A compound according to claim 5, and being (.+-.) trans-4,5,5a,6,7,8,9,9a-octahydro-6-propyloxazolo[5,4-f]quinolin-2-amine or a pharmaceutically acceptable acid addition salt thereof.
- 53. A method of treating psychoses, hypertension, galactorrhea, amenorrhea, menstrual disorders, sexual dysfunction, Parkinson's disease, Huntington's chorea or depression comprising administering to a host suffering therefrom a therapeutic effective amount of a compound according to claim 1 in unit dosage form.
- 54. A method of treating schizophrenia comprising administering to a host suffering therefrom a therapeutic effective amount of a compound according to claim 1 in unit dosage form.
- 55. A pharmaceutical composition adapted for administration as a dopaminergic, antipsychotic or antihypertensive agent comprising a therapeutic effective amount of a compound according to claim 1 in admixture with a pharmaceutically acceptable excipient, diluent or carrier.
Parent Case Info
This is a continuation-in-part of U.S. application Ser. No. 907,445 filed Sept. 15, 1986 and now abandoned.
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
907445 |
Sep 1986 |
|