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Last Updated: March 28, 2024

Details for Patent: 6,037,364


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Title: Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents
Abstract:The invention relates to the use of derivatives of F-type prostaglandins as ocular hypotensives. The PGF derivatives used in accordance with the invention are represented by the following formula I: ##STR1## wherein wavy line attachments indicate either the alpha (.alpha.) or beta (.beta.) configuration; dashed bonds represent a double bond, or a single bond, R is a substituted heteroaryl radical, R.sup.1 is hydrogen or a lower alkyl radical having up to six carbon atoms, X is selected from the group consisting of --OR.sup.1 and --N(R.sup.1).sub.2, Y is .dbd.O or represents 2 hydrogen radicals. Certain of the compounds represented by Formula I comprise another aspect of the present invention.
Inventor(s): Burk; Robert M. (Laguna Beach, CA)
Assignee: Allergan Sales, Inc. (Irvine, CA)
Filing Date:Apr 20, 1999
Application Number:09/295,003
Claims:1. A method of treating a pathophysiological disease selected from the group consisting of acute myocardial infarction, vascular thrombosis, pulmonary hypertension, ischemic heart disease, congestive heart failure, and angina pectoris which comprises administering to a mammal having said disease a therapeutically effective amount of a compound represented by formula I: ##STR36## wherein the hatched segments represent .alpha. bonds, the solid triangle represents a .beta. bond, wavy line attachments indicate either the alpha (.alpha.) or beta (.beta.) configuration; dashed bonds represent a double bond or a single bond, R is a substituted hetero aryl radical, R.sup.1 is hydrogen or a lower alkyl radical having up to six carbon atoms, X is selected from the group consisting of --OR.sup.1 and --N(R.sup.1).sub.2, Y is.dbd.O or represents 2 hydrogen radicals.

2. The method of claim 1 wherein the substituent on the heteroaryl radical is selected from the group consisting of lower alkyl, halogen, trifluoromethyl (CF.sub.3), COR.sub.1, COCF.sub.3, SO.sub.2 NR.sub.1, SO.sub.2 NH.sub.2, NO.sub.2 and CN.

3. The method of claim 2 wherein said compound is represented by formula II: ##STR37## wherein Z is selected from the group consisting of O and S, A is selected from the group consisting of N, --CH, and C, R.sup.2 is selected from the group consisting of hydrogen, halogen and lower alkyl having from 1 to 6 carbon atoms, R.sup.3 and R.sup.4 are selected from the group consisting of hydrogen, halogen, lower alkyl having from 1 to 6 carbon atoms, or, together with, ##STR38## R.sup.3 and R.sup.4 forms a condensed aryl ring and provided at least one of R.sup.2, R.sup.3 and R.sup.4 is not hydrogen.

4. The method of claim 3 wherein said compound represented by formula III: ##STR39## wherein R.sup.5 hydrogen or methyl.

5. The method of claim 4 wherein X is --OH or --NH.sub.2.

6. The method of claim 4 wherein Y is.dbd.O and X is --OH.

7. The method of claim 4 wherein Y is.dbd.O and X is --NH.sub.2.

8. The method of claim 4 wherein Z is S.

9. The method of claim 8 wherein at least one of R.sup.2, R.sup.3 and R.sup.4 are selected from the group consisting of halogen, lower alkyl having from 1 to 4 carbon atoms and lower alkoxy having from 1 to 4 carbon atoms.

10. The method of claim 8 wherein at least one of R.sup.2, R.sup.3 and R.sup.4 is selected from the group consisting of chloro and bromo.

11. The method of claim 8 wherein at least one of R.sup.2, R.sup.3 and R.sup.4 are chloro.

12. The method of claim 11 wherein at least two of R.sup.2, R.sup.3 and R.sup.4 are chloro.

13. The method of claim 4 wherein Y is.dbd.O, X is --OH or --NH.sub.2 and Z is S.

14. The method of claim 13 wherein at least one of R.sup.2, R.sup.3 and R.sup.4 is selected from the group consisting of chloro and bromo.

15. The method of claim 13 wherein at least one of R.sup.2, R.sup.3 and R.sup.4 are bromo or at least two of R.sup.2, R.sup.3 and R.sup.4 are chloro.

16. The method of claim 15 wherein said compound is 7-[3.alpha.,5.alpha.-Dihydroxy-2-(3.alpha.-hydroxy-5-(2-(4-bromo)thienyl)- 1E-pentenyl)cyclopentyl]-5Z-heptenoic acid.

17. The method of claim 15 wherein said compound is 7-[3.alpha.,5.alpha.-Dihydroxy-2-(3.alpha.-hydroxy-5-(3-(2, 5-dichloro)thienyl-1E -pentenyl)cyclopentyl]-5Z-heptenoic acid.

18. The method of claim 15 wherein said compound is 7-[3.alpha.,5.alpha.-Dihydroxy-2-(3.alpha.-hydroxy-5-(2-(5-bromo)thienyl)- 1E-pentenyl)cyclopentyl]-5Z-heptenoic acid.

19. The method of claim 15 wherein said compound is 7-[3.alpha.,5.alpha.-Dihydroxy-2-(3.alpha.-hydroxy-5-(2-(3-chloro)thienyl) -1E-pentenyl)cyclopentyl]-5Z-heptenoic acid.

20. The method of claim 15 wherein said compound is 7-[3.alpha.,5.alpha.-Dihydroxy-2-(3.alpha.-hydroxy-5-(3-(2-chloro)thienyl- 1E-pentenyl)cyclopentyl]-5Z-heptenoic acid.

21. The method of claim 15 wherein said compound is 7-[3.alpha.,5.alpha.-Dihydroxy-2-(3.alpha.-hydroxy-5-(3-(2, 5-dichloro)thienyl)-1E -pentenyl)cyclopentyl]-5Z-heptenamide.

22. The method of claim 13 wherein at least one of R.sup.2, R.sup.3 and R.sup.4 is a lower alkyl radical having from 1 to 4 carbon atoms.

23. The method of claim 22 wherein at least one of R.sup.2, R.sup.3 and R.sup.4 are ethyl, propyl or butyl.

24. The method of claim 23 wherein said compound is 7-[3.alpha.,5.alpha.-Dihydroxy-2-(3.alpha.-hydroxy-5-(2-(5 ethyl)thienyl)-1E-pentenyl)cyclopentyl]-5Z-heptenoic acid.

25. The method of claim 23 wherein said compound is 7-[3.alpha.,5.alpha.-Dihydroxy-2-(3.alpha.-hydroxy-5-(2-(5-propyl)thienyl) -1-pentenyl)cyclopentyl]-5Z-heptenoic acid.

26. The method of claim 24 wherein said compound is 7-[360 ,5.alpha.-Dihydroxy-2-(3.alpha.-hydroxy-5-(2-(5-butyl)thienyl-1E -pentenyl)cyclopentyl]-5Z- heptenoic acid.

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