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Claims for Patent: 4,855,290

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Claims for Patent: 4,855,290

Title: Derivatives of quinuclidine
Abstract:Quinuclidine derivatives having the general formula (I) ##STR1## and geometrical isomers, enantiomers, diastereoisomers, racemates and/or acid addition salts thereof, wherein Z represents the group >CR.sup.1 R.sup.2 or two hydrogen atoms; and R.sup.1 and R.sup.2, which may be identical or different, are each alkyl, cyclopentyl, cyclohexyl, aryl, or diarylmethylol, or alkyl which is substituted by one or more aryl groups, or one of R.sup.1 and R.sup.2 may be hydrogen.
Inventor(s): Fisher; Abraham (Holon, IL), Karton; Ishai (Ness-Ziona, IL), Heldman; Eliahu (Rehovot, IL), Levy; Aharon (Moshav Beith Hanan, IL), Grunfeld; Yona (Rehovot, IL)
Assignee: State of Israel, represented by Prime Minister's Office, Israel (Ness-Ziona, IL)
Application Number:06/853,404
Patent Claims: 1. A compound of the formula (I) ##STR5## and geometrical isomers, enantiomers, diastereoisomers, racemates and/or acid addition salts thereof, wherein R.sup.1 is selected from the group consisting of hydrogen, lower alkyl, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and lower alkyl which is substituted by one or two phenyl groups and R is selected from the group consisting of lower alkyl, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and lower alkyl which is substituted by one or two phenyl groups.

2. A compound according to claim 1, wherein R.sup.1 is hydrogen, and R.sup.2 is selected from the group consisting of lower alkyl, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and lower alkyl which is substituted by one or two phenyl groups.

3. A compound according to claim 1, wherein R.sup.1 is selected from the group consisting of lower alkyl, cyclopentyl and cyclohexyl, and R.sup.2 is selected from the group consisting of lower alkyl, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and lower alkyl which is substituted by one or two phenyl groups.

4. A compound according to claim 1, wherein R.sup.1 is phenyl, and R.sup.2 is selected from the group consisting of phenyl, diphenylmethylol and lower alkyl which is substituted by one or two phenyl groups.

5. A compound according to claim 2, wherein R.sup.1 is hydrogen and R.sup.2 is methyl.

6. A compound according to claim 2, wherein R.sup.1 is hydrogen and R.sup.2 is phenyl.

7. A compound according to claim 2, wherein R.sup.1 is hydrogen and R.sup.2 is diphenylmethyl.

8. A compound according to claim 2, wherein R.sup.1 is hydrogen and R.sup.2 is selected from the group consisting of ethyl, propyl and diphenylmethylol.

9. A compound according to claim 3, wherein R.sup.1 is methyl and R.sup.2 is phenyl.

10. A compound according to claim 3, wherein R.sup.2 is phenyl and R.sup.1 is selected from the group consisting of ethyl and cyclohexyl.

11. A compound according to claim 4, wherein R.sup.1 and R.sup.2 are each phenyl.

12. The geometrical isomer of the compound according to claim 5, the hydrochloric acid salt of which has the relatively lower melting-point (the cis-isomer).

13. The geometrical isomer of the compound according to claim 5, the hydrochloric acid salt of which has the relatively higher melting-point (the trans-isomer).

14. The hydrochloric acid salt of the compound according to claim 5.

15. The relatively lower melting-point geometrical isomer (the cis-isomer) of the compound according to claim 14.

16. The relatively higher melting-point geometrical isomer (the trans-isomer) of the compound according to claim 14.

17. A pharmaceutical composition comprising a compound of formula (I) according to claim 1, or a pharmaceutically compatible acid addition salt thereof, together with an inert carrier or diluent.

18. A pharmaceutical composition according to claim 17, which is in a form suitable for oral, rectal or parenteral administration, or for administration by insufflation.

19. A pharmaceutical composition according to claim 17, which is in a form suitable for transdermal administration.

20. A pharmaceutical composition according to claim 17, which is in unit dosage form.

21. A pharmaceutical composition for transdermal administration, comprising a compound of formula (I) according to claim 1, or a pharmaceutically compatible acid addition salt thereof, and a low molecular weight fatty acid.

22. A pharmaceutical composition according to claim 17, wherein the compound of formula (I) is that in which R.sup.1 is phenyl, and R.sup.2 is selected from the group consisting of ethyl, cyclohexyl and phenyl.

23. A pharmaceutical composition according to claim 17, wherein the compound of formula (I) is that in which R is hydrogen, and R.sup.2 is selected from the group consisting of methyl and ethyl.

24. A pharmaceutical composition according to claim 17, wherein the compound of formula (I) is that defined in claim 12.

25. A pharmaceutical composition according to claim 24, further comprising one or more compounds selected from the group consisting of physostigmine, tetrahydroaminoacridine, choline, lecithin, piracetam, aniracetam, pramiracetam, oxiracetam, 4-aminopyridine, 3,4-diaminopyridine and somatostatin.

26. A pharmaceutical composition according to claim 17, wherein the compound of formula (I) is that in which R.sup.2 is selected from the group consisting of lower alkyl containing at least three carbon atoms, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and lower alkyl substituted by one or two phenyl groups, and R.sup.1 is selected from the group consisting of hydrogen, lower alkyl, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and lower alkyl substituted by one or two phenyl groups.

27. A pharmaceutical composition according to claim 26, wherein the compound formula (I) is that in which R.sup.1 is ethyl and R.sup.2 is phenyl.

28. A pharmaceutical composition according to claim 26, wherein the compound of formula (I) is that in which R.sup.1 is hydrogen and R.sup.2 is diphenylmethyl.

29. A pharmaceutical composition according to claim 26, wherein the compound of formula (I) is that in which R.sup.1 is hydrogen, and R.sup.2 is selected from the group consisting of propyl, phenyl, and diphenylmethylol.

30. A method for treating diseases of the central nervous system in mammals, comprising administering to the mammal a compound of formula (I) according to claim 1 or a pharmaceutically compatible acid addition salt thereof.

31. A method for treating diseases of the central nervous system in mammals, comprising administering to the mammal a pharmaceutical composition according to in claim 17.

32. A method for treating diseases of the central nervous system is mammals, comprising transdermal administration to the mammal of a compound of formula (I) according to claim 1 or a pharmaceutically compatible acid addition salt thereof.

33. A method for treating diseases due to a deficiency in the central cholinergic system in mammals, comprising administering to the mammal a compound according to claim 2, wherein R.sup.1 is hydrogen and R.sup.2 is methyl, or geometrical isomers, enantiomers, racemates or acid addition salts thereof.

34. A method for treating diseases due to a deficiency in the central cholinergic system in mammals, comprising administering to the mammal a pharmaceutical composition containing a compound according to claim 2, wherein R.sup.1 is hydrogen and R.sup.2 is methyl, or geometrical isomers, enantiomers, racemates or acid addition salts thereof, together with an inert carrier or diluent.

35. A method for treating diseases due to a deficiency in the central cholinergic system in mammals, comprising transdermal administration to the mammal of a compound according to claim 2, wherein R.sup.1 is hydrogen and R.sup.2 is methyl, or geometrical isomers, enantiomers, racemates or acid addition salts thereof.

36. A method for treating diseases due to cholinergic hyperfunction in mammals, comprising administering to the mammal a compound of formula (I) according to claim 1 or a pharmaceutically compatible acid addition salt thereof, wherein R.sup.2 is selected from the group consisting of lower alkyl containing at least three carbon atoms, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and lower alkyl substituted by one or two phenyl groups, and R.sup.1 is selected from the group consisting of hydrogen, lower alkyl, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and alkyl substituted by one or two phenyl groups.

37. A method for treating diseases due to cholinergic hyperfunction in mammals, comprising administering to the mammal a pharmaceutical composition containing a compound of formula (I) according to claim 1 or a pharmaceutically compatible acid addition salt thereof, wherein R.sup.2 is selected from the group consisting of lower alkyl containing at least three carbon atoms, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and lower alkyl substituted by one or two phenyl groups, and R.sup.1 is selected from the group consisting of hydrogen, lower alkyl, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and alkyl substituted by one or two phenyl groups, together with an inert carrier or diluent.

38. A method for treating diseases due to cholinergic hyperfunction in mammals, comprising transdermal administration to the mammal of a compound of formula (I) or a pharmaceutically compatible acid addition salt thereof, wherein R.sup.2 is selected from the group consisting of lower alkyl containing at least three carbon atoms, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and lower alkyl substituted by one or two phenyl groups, and R.sup.1 is selected from the group consisting of hydrogen, lower alkyl, cyclopentyl, cyclohexyl, phenyl, diphenylmethylol and lower alkyl substituted by one or two phenyl groups.

39. A method of treating diseases due to cholinergic hyperfunction in mammals, comprising administering to the mammal a compound according to claim 7, or a pharmaceutically compatible acid addition salt thereof.

40. A method for treating diseases due to cholinergic hyperfunction in mammals, comprising administering to the mammal a pharmaceutical composition containing a compound according to claim 7, or a pharmaceutically compatible acid addition salt thereof, together with an inert carrier or diluent.

41. A method for treating diseases due to a deficiency in the central cholinergic system in mammals, comprising transdermal administration to the mammal of a compound according to claim 7, or a pharmaceutically compatible acid addition salt thereof.

42. A method for treating diseases due to cholinergic hyperfunction in mammals, comprising administering to the mammal a compound according to claim 9, or a pharmaceutically compatible acid addition salt thereof.

43. A method for treating diseases due to cholinergic hyperfunction in mammals, comprising administering to the mammal a pharmaceutical composition containing a compound according to claim 9, or a pharmaceutically compatible acid addition salt thereof, together with an inert carrier or diluent.

44. A method for treating diseases due to cholinergic hyperfunction in mammals, comprising transdermal administration to the mammal of a compound according to claim 9, or a pharmaceutically compatible acid addition salt thereof.

45. A method for treating senile dementia of Alzheimer's type, comprising administering to a patient a compound according to claim 13, or pharmaceutically compatible acid addition salt thereof.

46. A method for treating senile dementia of Alzheimer's type, comprising administering to a patient a pharmaceutical composition containing a compound according to claim 12, or a pharmaceutically compatible acid addition salt thereof, together with an inert carrier or diluent.

47. A method for treating senile dementia of Alzheimer's type, comprising transdermal administration to a patient of a compound according to claim 12, or a pharmaceutically compatible acid addition salt thereof.

48. A method according to claim 45 wherein there is coadministered with said compound, one or more compounds selected from the group consisting of physostigmine, tetrahydroaminoacridine, choline, lecithin, piracetam, aniracetam, pramiracetam, oxiracetam, 4-aminopyridine, 3,4-diaminopyridine and somatostatin.

49. A method according to claim 46 wherein there is coadministered with said compound, one or more compounds selected from the group consisting of physostigmine, tetrahydroaminoacridine, choline, lecithin, piracetam, aniracetam, pramiracetam, oxiracetam, 4-aminopyridine, 3,4-diaminopyridine and somatostatin.

50. A method according to claim 47 wherein there is coadministered with said compound, one or more compounds selected from the group consisting of physostigmine, tetrahydroaminoacridine, 4-aminopyridine and 3,4-diaminopyridine.

51. A pharmaceutical composition in unit dosage form comprising a compound of formula (I) according to claim 1, or a pharmaceutically compatible acid addition salt thereof, in an amount ranging from about 0.5 to about 500 mg., together with an inert carrier or diluent.

52. A pharmaceutical composition according to claim 51 comprising the said compound, or a pharmaceutically compatible acid addition salt thereof, in an amount in the range of about 5 to about 100 mg.

53. A pharmaceutical composition according to claim 52 comprising the said compound, or a pharmaceutically compatible acid addition salt thereof, in an amount in the range of about 10 to about 50 mg.

54. A pharmaceutical composition according to claim 51, further comprising one or more compounds selected from the group consisting of physostigmine, tetrahydroaminoacridine, choline, lecithin, piracetam, aniracetam, pramiracetam, oxiracetam, 4-aminopyridine, 3,4-diaminopyridine and somatostatin.

55. A pharmaceutical composition according to claim 51, wherein the composition is adapted for oral administration.

56. A pharmaceutical composition according to claim 51, wherein the composition is adapted for parenteral administration.

57. A method for treating senile dementia of Alzheimer's type, comprising orally administering to a patient a compound according to claim 12, or a pharmaceutically compatible acid addition salt thereof, in an amount ranging from about 0.1 to about 60 mg./kg. body weight.

58. A method according to claim 57 wherein said amount ranges from about 0.5 to about 10 mg./kg. body weight.

59. A method according to claim 58 wherein said amount ranges from about 1 to about 5 mg./kg. body weight.

60. A method according to claim 57, wherein there is coadministered with the said compound, one or more compounds selected from the group consisting of physostigmine, tetrahydroaminoacridine, choline, lecithin, piracetam, aniracetam, pramiracetam, oxiracetam, 4-aminopyridine, 3,4-diaminopyridine and somatostatin.

61. A method according to claim 59, wherein administration is by means of a pharmaceutical composition in unit dosage form comprising the said compound in an amount about 0.5 to about 500 mg., together with an inert carrier or diluent.

62. A method for treating senile dementia of Alzheimer's type, comprising parenterally administering to a patient a compound according to claim 12, or a pharmaceutically compatible acid addition salt thereof, in an amount ranging from about 0.01 to about 40 mg./kg. body weight.

63. A method according to claim 62 wherein said amount ranges from about 0.05 to about 5 mg./kg. body weight.

64. A method according to claim 63 wherein said amount ranges from about 0.1 to about 2 mg./kg. body weight.

65. A method according to claim 62, wherein there is coadministered with the said compound, one or more compounds selected from the group consisting of physostigmine, tetrahydroaminoacridine, choline, lecithin, piracetam, aniracetam, pramiracetam, oxiracetam, 4-aminopyridine, 3,4-diaminopyridine and somatostatin.

66. A method according to claim 62, wherein administration is by means of a pharmaceutical composition in unit dosage form comprising the said compound in an amount ranging from about 0.5 to about 500 mg., together with an inert carrier or diluent.

67. The compound 3-hydroxy-3-mercaptomethyl quinuclidine.
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