Claims
- 1. The method for relieving bronchospasm in a mammal suffering therefrom which comprises administering to said mammal a non-toxic bronchodilator effective dose of a compound selected from the group consisting of ##STR27## wherein R.sup.11 is hydrogen or lower alkyl up to 8 carbon atoms,
- R.sup.12 is hydrogen, lower alkyl up to 8 carbon atoms or halogen when R.sub.11 is hydrogen,
- R.sub.14 is selected from the group consisting of lower alkyl having up to 8 carbon atoms, cycloalkylalkyl having 4 to 12 carbon atoms, pyridylmethyl, aralkyl or substituted aralkyl having 7 to 12 carbon atoms, aryloxyalkyl or substituted aryloxyalkyl having 8 to 12 carbon atoms wherein each of said substituted aralkyl and substituted aryloxyalkyl groups contains 1 or 2 non-sterically hindered ring substituents selected from halogen and alkoxy having up to 6 carbon atoms,
- R.sup.6 and R.sup.7 are attached to ring carbon atoms and are selected from hydrogen, methyl, and ethyl,
- R.sup.16 represents hydrogen or a double bond between adjacent ring carbon atoms,
- n is the integer 1 and the pharmaceutically acceptable acid addition salts thereof.
- 2. The method for exerting a vasodilator effect in a mammal which comprises administering to a mammal in need of vasodilation a non-toxic vasodilator effective dose of a compound selected from the group consisting of ##STR28## wherein R.sup.11 is hydrogen or lower alkyl up to 8 carbon atoms,
- R.sup.12 is hydrogen, lower alkyl having up to 8 carbon atoms or halogen when R.sup.11 is hydrogen,
- R.sup.14 is selected from the group consisting of lower alkyl having up to 8 carbon atoms, cycloalkylalkyl having 4 to 12 carbon atoms, pyridylmethyl, aralkyl or substituted aralkyl having 7 to 12 carbon atoms, aryloxyalkyl or substituted aryloxyalkyl having 8 to 12 carbon atoms wherein each of said substituted aralkyl and substituted aryloxyalkyl groups contains 1 or 2 non-sterically hindered ring substituents selected from halogen and alkoxy having up to 6 carbon atoms,
- R.sup.6 and R.sup.7 are attached to ring carbon atoms and are selected from hydrogen, methyl, and ethyl,
- R.sup.16 represents hydrogen or a double bond between adjacent ring carbon atoms,
- n is the integer 1 and the pharmaceutically acceptable acid additon salts thereof.
- 3. The method of claims 1 or 2 wherein in said compound R.sup.11, R.sup.12, R.sup.6, R.sup.7, and R.sup.16 are hydrogen atoms, n is the integer 1, and R.sup.14 is the substituted aralkyl group.
- 4. The method of claims 1 or 2 wherein said compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)one.
- 5. The method of claims 1 or 2 wherein said compound is 4-[(4-chlorophenyl)methyl]-1-6,7-dihydro -3H-imidazo[1,2-a]purin-9(4H)-one hydrochloride.
- 6. The method of claims 1 or 2 wherein in said compound R.sup.11 is lower alkyl, R.sup.12, R.sup.6 , R.sup.7, and R.sup.16 are hydrogen, n is the integer 1, and R.sup.14 is the substituted aralkyl group.
- 7. The method of claims 1 or 2 wherein in said compound R.sup.11, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.12 is alkyl, n is the integer 1, and R.sup.14 is substituted aralkyl.
- 8. The method of claims 1 or 2 wherein said compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-2-methyl-3H-imidazo[1,2-a]purin-9(4H-one.
- 9. The method of claims 1 or 2 wherein in said compound R.sub.11, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.12 is halogen, n is the integer 1, and R.sup.14 is substituted aralkyl.
- 10. The method of claims 1 or 2 wherein in said compound R.sup.11, R.sup.12, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.14 is lower alkyl, and n is the integer 1.
- 11. The method of claims 1 or 2 wherein in said compound R.sup.11, R.sub.12, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.14 is pyridylmethyl, and n is the integer 1.
- 12. The method of claims 1 or 2 wherein in said compound R.sup.11, R.sup.12, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.14 is aralkyl, and n is the integer 1.
- 13. The method of claims 1 or 2 wherein in said compound R.sup.11, R.sup.12, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.14 is aryloxyalkyl, and n is the integer 1.
- 14. The method of claims 1 or 2 wherein in said compound is 6,7-dihydro-2-methyl-4-(2-phenoxyethyl) imidazo[1,2-a]purin-9(4H)-one.
- 15. The method of claims 1 or 2 wherein said compound is 6,7-dihydro-2-methylethyl)-4-(2methylpropyl)-3Himidazo[1,2-a]-purin-9(4H)-one.
- 16. The method of claims 1 or 2 wherein said compound is 6,7-dihydro-2-methyl-4-(2-methylpropyl)3H-imidazo[1,2-a]purin-9(4H)-one.
- 17. The method of claims 1 or 2 wherein said compound is 6,7-dihydro-2-(1-methylethyl)-4-(2-phenoxyethyl)-3H-imidazo[1,2-a]purin-9(4H)-one.
- 18. The method of claims 1 or 2 wherein said compound is 4 [(4-chlorophenyl)methyl]-6,7-dihydro-6-methyl-3H-imidazo[1,2a]purin-9(4H)-one.
- 19. The method of claims 1 or 2 wherein said compound is 4[-(4-chlorophenyl)methyl]-6,7-dihydro-2,6-dimethyl-3H-imidazo[-1,2-a]-purin-9(4H-one.
- 20. The method of claims 1 or 2 wherein said compound is 4[(4-chlorophenyl)methyl]-6,7-dihydro-1,6-dimethyl-1H-imidazo[1,2-a]purin-9(4H-one.
- 21. The method of claims 1 or 2 wherein said compound is 4-[(4-chlorophenyl)methyl[-6,7-dihydro-1,2,6-trimethyl-1H-imidazo[1,2-a]purin-9(4H-one.
- 22. The method of claims 1 or 2 wherein said compound is 6,7-dihydro-6-methyl-4-(2-methylpropyl)-3H-imidazo[1,2-a]purin-9(4H)-one.
- 23. The method of claims 1 or 2 wherein said compound is selected from the group consisting of 4-[(4-chlorophenyl)methyl]-6,7-dihydro-6,6-dimethyl-3H-imidazo]1,2a]purin-9(4H)-one and a pharmaceutically acceptable acid additon salt thereof.
- 24. The method of claims 1 or 2 wherein said compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-6,6-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one.
- 25. The method of claims 1 or 2 wherein said compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-6,7-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one.
- 26. The method of claims 1 or 2 wherein said compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-trans-6,7-dimethyl-3H-imidazo[1,2-a]purin-9(4H-one.
- 27. The method of claims 1 or 2 wherein said compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-cis-6,7-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one.
- 28. The method of claims 1 or 2 wherein in said compound n is 1, R.sup.16 is hydrogen, and R.sup.6 and R.sup.7 are methyl or ethyl.
- 29. The method of claims 1 or 2 wherein said compound is selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR29## wherein R.sup.6, R.sup.7, R.sup.11 and R.sup.12 are selected from the group consisting of hydrogen and methyl.
- 30. The method of claims 1 or 2 wherein said compound is selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR30## wherein R.sup.12 is lower alkyl.
- 31. The method of claims 1 or 2 wherein said compound is selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR31## wherein R.sup.12 is hydrogen or lower alkyl.
- 32. The method of claim 1 or 2 wherein said compound is selected from the group consisting of
- (a) 4-[(3-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)-one;
- (b) 4-[(2-chlorphenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)-one;
- (c) 4-[(4-fluorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)-one;
- (d) 4-(2-pyridylmethyl)-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)-one;
- (e) 4-[2-(3,4-dimethoxyphenyl)ethyl]-6,7-dihydroxy-3H-imidazo[1,2-a]purin-9(4H)-one;
- (f) 6,7-dihydro-4-(2-phenoxyethyl)-3H-imidazo[1,2a]purin-9(4H)-one;
- (g) 4-[(4-chlorophenyl)methyl]-2-ethyl-6,7-dihydroimidazo[1,2-a]purin-9(4H)-one;
- (h) 2-bromo-4-[(4-chlorophenyl)methyl]-6,7-dihydro-3-H-imidazo[1,2-a]purin-9(4H)-one;
- (i) 6,7-dihydro-2-methyl-4-octyl-3H-imidazo[1,2-a]purin-9(4H)-one;
- (j) 6,7-dihydro-2-(1-methylethyl)-4-octylimidazo[1,2-a]purin-9(4H)-one;
- (k) 4-[2-(4-chlorophenoxy)ethyl]-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)-one;
- (l) 4-(cyclohexylmethyl)-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)-one; and
- (m) 4-[(4-chlorphenyl)methyl]-6,7-dihydro-1-methyl-1H-imidazo[1,2-a]purin9(4H-one.
REFERENCE TO RELATED APPLICATION
This application is a division of co-pending application Ser. No. 209,791 filed Nov. 24, 1980 (now U.S. Pat. No. 4,366,156) which is a division of Ser. No. 017,771 filed Mar. 5, 1979 (now U.S. Pat. No. 4,298,734) which is a continuation-in-part of Ser. No. 869,203 filed Jan. 13, 1978 and abandoned Mar. 17, 1979, which in turn is a continuation-in-part of Ser. No. 768,291 filed Feb. 14, 1977 and abandoned Oct. 13, 1978.
Divisions (2)
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Number |
Date |
Country |
Parent |
209791 |
Nov 1980 |
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Parent |
017771 |
Mar 1979 |
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Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
869203 |
Jan 1978 |
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Parent |
768291 |
Feb 1977 |
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