Claims
- 1. A compound selected from the group consisting of an optically active compound of the formula: ##SPC12##
- and a racemic mixture of that formula and the mirror image thereof wherein R is selected from the group consisting of methyl and phenyl; Z is a divalent radical selected from the group consisting of those of the formulae: ##EQU9## wherein m is an integer from 1 to 8, inclusive, p is an integer from 2 to 4, inclusive, q is an integer from 3 to 6, inclusive, R.sub.4 is an alkyl group having up to 3 carbon atoms, and R.sub.5 is an alkyl group having up to 4 carbon atoms, phenyl or fluoro; R.sub.1 is selected from the group consisting of a straight chain alkyl group having from 3 to 10 carbon atoms, a straight chain alkyl group having from 3 to 6 carbon atoms and having one branched alkyl group having up to 4 carbon atoms, a straight chain alkenyl group having from 3 to 6 carbon atoms, a straight chain .omega.-haloalkyl group having from 3 to 6 carbon atoms, a straight chain .omega.-phenylalkyl group having from 1 to 4 carbon atoms in the chain, a straight chain .omega.-(cycloalkyl)alkyl group having from 1 to 4 carbon atoms in the chain and from 5 to 7 carbon atoms in cycloalkyl, and moieties of the formulae:
- --(CH.sub.2).sub.p --S--R.sub.4 and --(CH.sub.2).sub.p --O--R.sub.4
- wherein p and R.sub.4 are as hereinabove defined; and the pharmaceutically acceptable anionic salts thereof.
- 2. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is n-hexyl, and Z is --(CH.sub.2).sub.6 --; 4-methylpiperazyl amide of l-9-oxo-13-trans-prostenoic acid.
- 3. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is n-hexyl, and Z is --(CH.sub.2).sub.6 --; 4-methylpiperazyl amide of dl-9-oxo-13-trans-prostenoic acid.
- 4. The optically active compound according to claim 4 wherein R is phenyl, R.sub.1 is n-hexyl, and Z is --(CH.sub.2).sub.6 --; 4-phenylpiperazyl amide of l-9-oxo-13-trans-prostenoic acid.
- 5. The racemic mixture according to claim 1 wherein R is phenyl, R.sub.1 is n-hexyl, and Z is --(CH.sub.2).sub.6 --; 4-phenylpiperazyl amide of dl-9-oxo-13-trans-prostenoic acid.
- 6. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is n-hexyl, and Z is --(CH.sub.2).sub.4 --O--CH.sub.2 --; 4-methylpiperazyl amide of l-9-oxo-3-oxa-13-trans-prostenoic acid.
- 7. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is n-hexyl, Z is --(CH.sub.2).sub.4 --O--CH.sub.2 --; 4-methylpiperazyl amide of dl-9-oxo-3-oxa-13-trans-prostenoic acid.
- 8. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is n-hexyl, and Z is --(CH.sub.2).sub.4 --S--CH.sub.2 --; 4-methylpiperazyl amide of l-9-oxo-3-thia-13-trans-prostenoic acid.
- 9. The racemic mixture according to claim 1 where R is methyl, R.sub.1 is n-hexyl, and Z is --(CH.sub.2).sub.4 --S--CH.sub.2 --; 4-methylpiperazyl amide of dl-9-oxo-3-trans-prostenoic acid.
- 10. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is n-hexyl, and Z is ##EQU10## 4-methylpiperazyl amide of l-9-oxo-2-ethyl-13-trans-prostenoic acid.
- 11. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is n-hexyl, and Z is ##EQU11## 4-methylpiperazyl amide of dl-9-oxo-2-ethyl-13-trans-prostenoic acid.
- 12. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is n-hexyl, and Z is ##EQU12## 4-methylpiperazyl amide of l-9-oxo-5-cis,13-trans-prostadienoic acid.
- 13. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is n-hexyl, and Z is ##EQU13## 4-methylpiperazyl amide of dl-9-oxo-5-cis,13-trans-prostadienoic acid.
- 14. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is n-hexyl, and Z is --(CH.sub.2).sub.5 --CHF--; 4-methylpiperazyl amide of l-9-oxo-2-fluoro-13-trans-prostenoic acid.
- 15. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is n-hexyl, and Z is --(CH.sub.2).sub.5 --CHF; 4-methylpiperazyl amide of dl-9-oxo-2-fluoro-13-trans-prostenoic acid.
- 16. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is --(CH.sub.2).sub.3 Cl, and Z is ##EQU14## 4-methylpiperazyl amide of l-9-oxo-2-phenyl-17-chloro-18,19,20-trinor-13-trans-prostenoic acid.
- 17. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is --(CH.sub.2).sub.3 Cl, and Z is ##EQU15## 4-methylpiperazyl amide of dl-9-oxo-2-phenyl-17-chloro-18,19,20-trinor-13-trans-prostenoic acid.
- 18. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is --(CH.sub.2).sub.3 Cl, and Z is ##EQU16## 4-methylpiperazyl amide of l-9-oxo-2-methyl-17-chloro-18,19,20-trinor-13-trans-prostenoic acid.
- 19. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is --(CH.sub.2).sub.3 Cl, and Z is ##EQU17## 4-methylpiperazyl amide of dl-9-oxo-2-methyl-17-chloro-18,19,20-trinor-13-trans-prostenoic acid.
- 20. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is n-propyl, and Z is ##EQU18## 4-methylpiperazyl amide of l-9-oxo-3,3-dimethyl-18,19,20-trinor-13-trans-prostenoic acid.
- 21. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is n-propyl, and Z is ##EQU19## 4-methylpiperazyl amide of dl-9-oxo-3,3-dimethyl-18,19,20-trinor-13-trans-prostenoic acid.
- 22. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is --CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2, and Z is ##EQU20## 4-methylpiperazyl amide of l-9-oxo-3,3,17-trimethyl-19,20-dinor-13-trans-prostenoic acid.
- 23. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is --CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2, and Z is ##EQU21## 4-methylpiperazyl amide of dl-9-oxo-3,3,17-trimethyl-19,20-dinor-13-trans-prostenoic acid.
- 24. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is .beta.-phenethyl, and Z is ##EQU22## 4-methylpiperazyl amide of l-9-oxo-3,3-dimethyl-16-phenyl-17,18,19,20-tetranor-13-trans-prostenoic acid.
- 25. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is .beta.-phenethyl, and Z is ##EQU23## 4-methylpiperazyl amide of dl-9-oxo-3,3-dimethyl-16-phenyl-17,18,19,20-tetranor-13-trans-prostenoic acid.
- 26. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is cyclohexylmethyl, and Z is ##EQU24## 4-methylpiperazyl amide of l-9-oxo-2-methyl-16,20-methano-13-trans-prostenoic acid.
- 27. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is cyclohexylmethyl, and Z is ##EQU25## 4-methylpiperazyl amide of dl-9-oxo-2-methyl-16,20-methano-13-trans-prostenoic acid.
- 28. The optically active compound according to claim 1 wherein R is methyl, R.sub.1 is --(CH.sub.2).sub.3 --C.sub.6 H.sub.5, and Z is --(CH.sub.2).sub.6 --; 4-methylpiperazyl amide of l-9-oxo-17-phenyl-18,19,20-trinor-13-trans-prostenoic acid.
- 29. The racemic mixture according to claim 1 wherein R is methyl, R.sub.1 is --(CH.sub.2).sub.3 --C.sub.6 H.sub.5, and Z is --(CH.sub.2).sub.6 --; 4-methylpiperazyl amide of dl-9-oxo-17-phenyl-18,19,20-trinor-13-trans-prostenoic acid.
Parent Case Info
This application is a C-I-P of Ser. No. 365,806, filed May 31, 1973, which is a continuation of Ser. No. 162,712, filed July 14, 1971, both abandoned.
Non-Patent Literature Citations (2)
Entry |
horton, Physiological Rev., vol. 49, pp. 122-161 (1969). |
Shaw et al., Research in Prostaglandins, Worcester Foundation for Experimental Biology, vol. 1, pp. 1-41, June, 1971. |
Continuations (1)
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Number |
Date |
Country |
Parent |
162712 |
Jul 1971 |
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Continuation in Parts (1)
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Number |
Date |
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Parent |
365806 |
May 1973 |
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