Claims
- 1. A compound selected from the group consisting of ##STR26## wherein Q is O, S, or NR.sup.10,
- R.sup.10 is selected from the group consisting of hydrogen, lower alkyl having up to 8 carbon atoms, lower alkenyl or lower alkynyl each having 3 to 8 carbon atoms, dialkylaminoalkyl having 4 to 12 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, cycloalkylalkyl having 4 to 12 carbon atoms, pyridylmethyl, aralkyl or substituted aralkyl each having 7 to 12 carbon atoms, aryloxyalkyl or substituted aryloxyalkyl each having 8 to 12 carbon atoms wherein each of said substituted aralkyl and substituted aryloxyalkyl groups contains 1 or 2 substituents selected from halogen, alkoxy, and alkyl, and each of said alkoxy and alkyl groups contains up to 6 carbon atoms,
- R.sup.11 is alkoxycarbonyl having 2 to 4 carbon atoms, aminoalkyl having 2 to 8 carbon atoms, or is independently selected from the foregoing group defined for R.sup.10,
- R.sup.12 is lower alkyl, lower alkenyl, lower alkynyl, lower alkylthio, lower alkylsulfinyl, or lower alkylsulfonyl each having up to 8 carbon atoms, hydrogen, thioxo, trifluoromethyl or halogen when R.sup.11 is hydrogen,
- R.sup.12 is lower alkylamino, di-lower alkylamino, lower alkoxyimino, lower alkyl, lower alkenyl, lower alkynyl, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, or lower alkoxy each having up to 8 carbon atoms, hydrogen, thioxo, trifluoromethyl, halogen, hydrazino, azido, cyano, hydroxy, or amino when R.sup.11 is other than hydrogen,
- R.sup.14 is selected from the group consisting of lower alkyl having up to 8 carbon atoms, lower alkenyl or lower alkynyl having 3 to 8 atoms, cycloalkyl having 3 to 6 carbon atoms, cycloalkylalkyl having 4 to 12 carbon atoms, pyridylmethyl, lower alkanoyl or lower alkenoyl or lower alkynoyl each having up to 8 carbon atoms, aroyl or substituted aroyl having 7 to 12 carbon atoms, 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 aroyl, substituted aralkyl, and substituted aryloxyalkyl groups contains 1 or 2 ring substituents selected from halogen, alkoxy, and alkyl, and each of said alkoxy and alkyl groups contains 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, 2 or 3,
- the pharmaceutically acceptable acid addition and quaternary ammonium salts of the foregoing compounds, and the pharmaceutically acceptable metal, ammonium, and amine salts of the foregoing compounds wherein R.sup.11 is hydrogen.
- 2. The compound of claim 1 having Formula XX wherein R.sup.11, R.sup.12, R.sup.6, R.sup.7, and R.sup.16 are hydrogen atoms, n is the integer 1, Q is 0, and R.sup.14 is the substituted aralkyl group.
- 3. The compound of claim 2, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)-one.
- 4. The compound of claim 2, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)-one hydrochloride.
- 5. The compound of claim 1 having Formula XX wherein 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, Q is 0, and R.sup.14 is the substituted aralkyl group.
- 6. The compound of claim 1 having formula XX wherein R.sup.11, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.12 is alkyl, Q is 0, and R.sup.14 is substituted aralkyl.
- 7. The compound of claim 6, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-2-methyl-3H-imidazo[1,2-a]purin-9(4H)-one.
- 8. The compound of claim 1 having Formula XX wherein R.sup.11, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.12 is halogen, Q is 0, and R.sup.14 is substituted aralkyl.
- 9. The compound of claim 1 having Formula XX wherein R.sup.11, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.12 is lower alkyl, R.sup.14 is lower alkanoyl, n is the integer 1, and Q is 0.
- 10. The compound of claim 1 having the Formula XX wherein R.sup.11, R.sup.12, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.14 is lower alkyl, n is the integer 1, and Q is 0.
- 11. The compound of claim 1 having the Formula XX wherein R.sup.11, R.sup.12, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.14 is pyridylmethyl, n is the integer 1, and Q is 0.
- 12. The compound of claim 1 having the Formula XX wherein R.sup.11, R.sup.12, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.14 is aralkyl, n is the integer 1, and Q is 0.
- 13. The compound of claim 1 having Formula XX wherein R.sup.11, R.sup.12, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.14 is arlyoxyalkyl, n is the integer 1 and Q is 0.
- 14. The compound of claim 1 having Formula XX wherein R.sup.11, R.sup.6, R.sup.7, and R.sup.16 are hydrogen, R.sup.12 is loweralkylamino, R.sup.14 is substituted aralkyl, n is the integer 1, and Q is 0.
- 15. The compound of claim 1 having Formula XX, 6,7-dihydro-2-methyl-4-(2-phenoxyethyl)imidazo[1,2-a]purin-9(4H)-one.
- 16. The compound of claim 1 having Formula XX, 6,7-dihydro-2-(1-methylethyl)-4-(2-methylpropyl)-3H-imidazo[1,2-a]purin-9(4H)-one.
- 17. The compound of claim 1 having Formula XX, 6,7-dihydro-2-methyl-4-(2-methylpropyl)-3H-imidazo[1,2-a]purin-9(4H-one.
- 18. The compound of claim 1 having Formula XX, 6,7-dihydro-2-(1-methylethyl)-4-(2-phenoxyethyl)-3H-imidazo[1,2-a]purin-9(4H)-one.
- 19. The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-6-methyl-3H-imidazo[1,2-a]purin-9(4H)-one.
- 20. The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-2,6-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one.
- 21. The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-1,6-dimethyl-1H-imidazo[1,2-a]purin-9(4H)-one.
- 22. The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-1,2,6-trimethyl-1H-imidazo[1,2-a]purin9(4H)-one.
- 23. The compound of claim 1 having Formula XX, 6,7-dihydro-6-methyl-4-(2-methylpropyl)-3H-imidazo[1,2-a]purin-9(4H)-one.
- 24. The compound of claim 1 having Formula XX selected from the group consisting of 4-[(4-chlorophenyl)methyl]-6,7-dihydro-6,6-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one and a pharmaceutically acceptable acid addition salt thereof.
- 25. The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-6,6-dimethyl-3H-imidazo[1,2-a]-purin-9(4H)-one.
- 26. The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-6,7-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one.
- 27. The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-trans-6,7-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one.
- 28. The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-cis-6,7-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one.
- 29. The compound of claim 1 having Formula XX wherein Q is oxo, n is 1, R.sup.16 is hydrogen, and R.sup.6 and R.sup.7 are methyl or ethyl.
- 30. A compound selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR27## wherein R.sup.6, R.sup.7, R.sup.11 and R.sup.12 are selected from the group consisting of hydrogen and methyl.
- 31. A compound selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR28## wherein R.sup.12 is lower alkyl of up to 8 carbon atoms.
- 32. A compound selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR29## wherein R.sup.12 is hydrogen or lower alkyl of up to 8 carbon atoms.
REFERENCE TO RELATED APPLICATION
This application is a continuation-in-part of co-pending application Ser. No. 869,203 filed Jan. 13, 1978 and now abandoned, which in turn is a continuation-in-part of application Ser. No. 768,291 filed Feb. 14, 1977 and abandoned Oct. 13, 1978.
US Referenced Citations (4)
Non-Patent Literature Citations (5)
Entry |
Hardtman et al., J. Med. Chem. 18, pp. 447-453 (1975). |
Seidehamel Abst. of Papers 175th Mat. ACS Mtg. 3/13/78, Abstr. No. 8, Med. Chem. Section. |
Seidehamel et al., Amer. Chem. Soc. Symposium Series 118, 1980, pp. 293-297. |
Temple J. Med. Chem., vol. 23, pp. 1188-1198 (1980). |
Kamiya et al., Japanese Pat. 74-28,760, cited in C.A., vol. 182, (1975), Abst. No. 140,190e. |
Continuation in Parts (2)
|
Number |
Date |
Country |
Parent |
869203 |
Jan 1978 |
|
Parent |
768291 |
Feb 1977 |
|