Pharmaceutical composition comprising 11-deoxy-prostaglandin compound and method for stabilizing the compound

1. A pharmaceutical composition comprising a 11-deoxy-prostaglandin compound represented by formula (III):

wherein L is hydrogen, hydroxy, halogen, lower alkyl, hydroxy(lower)alkyl, lower alkanoyloxy or oxo, wherein the five-membered ring may optionally have at least one double bond;

A is —CH 3 , —CH 2 OH, —COCH 2 OH, —COOH or a functional derivative thereof;

B is single bond, —CH 2 —CH 2 —, —CH═CH—, —C≡C—, —CH 2 —CH 2 —CH 2 —, —CH═CH—CH 2 —, —CH 2 —CH═CH—, —C≡C—CH 2 — or —CH 2 —C≡C—;

R 1 is a saturated or unsaturated bivalent lower or medium aliphatic hydrocarbon, which is unsubstituted or substituted with halogen, lower alkyl, hydroxy, oxo, aryl or heterocyclic group, and at least one of carbon atom in the aliphatic hydrocarbon is optionally substituted by oxygen, nitrogen or sulfur;

R 2 is a single bond or lower alkylene;

R 3 is lower alkyl, lower alkoxy, lower alkanoyloxy, cyclo(lower)alkyl, cyclo(lower)alkyloxy, aryl, aryloxy, heterocyclic group or heterocyclic-oxy group, and at least one carbon atom in the aliphatic hydrocarbon is optionally substituted by oxygen, nitrogen or sulfur;

X 1 and X 2 are hydrogen, lower alkyl, or halogen; and

Z is ═O, and

a fatty acid ester derived from (1) a fatty acid and (2) glycerine.

2. The composition as described in claim 1 , wherein said 11-deoxy-prostaglandin compound is a 11-deoxy-13,14-dihydro-prostaglandin compound.

3. The composition as described in claim 1 , wherein said 11-deoxy-prostaglandin compound is a 11-deoxy-15-keto-prostaglandin compound.

4. The composition as described in claim 1 , wherein said 11-deoxy-prostaglandin compound is a 11-deoxy-13,14-dihydro-15-keto-prostaglandin compound.

5. The composition as described in claim 1 , wherein said 11-deoxy-prostaglandin compound is a 11-deoxy-16-mono or dihalogen-prostaglandin compound.

6. The composition as described in claim 1 , wherein said 11-deoxy-prostaglandin compound is a 11-deoxy-13,14-dihydro-16-mono or dihalogen-prostaglandin compound.

7. The composition as described in claim 1 , wherein said 11-deoxy-prostaglandin compound is a 11-deoxy-15-keto-16-mono or dihalogen-prostaglandin compound.

8. The composition as described in claim 1 , wherein said 11-deoxy-prostaglandin compound is a 11-deoxy-13,14-dihydro-15-keto-16-mono or dihalogen-prostaglandin compound.

9. The composition as described in claim 1 , wherein said 11-deoxy-prostaglandin compound is a 11-deoxy-13,14-dihydro-15-keto-16-mono or difluoro-prostaglandin compound.

10. The composition as described in claim 1 , wherein said 11-deoxy-prostaglandin compound is a 11-deoxy-13,14-dihydro-15-keto-16-mono or dihalogen-prostaglandin E or F compound.

11. The composition as described in claim 1 , wherein said prostaglandin compound is 11-deoxy-13,14-dihydro-15-keto-16-mono or difluoro-prostaglandin E or F compound.

12. The composition as described in claim 1 , wherein said 11-deoxy-prostaglandin compound is a 11-deoxy-13,14-dihydro-15-keto-16,16-difluoro-prostaglandin E 1 compound.

13. The composition as described in claim 1 , wherein said fatty acid ester is a glyceride of a fatty acid having 6-24 carbon atoms.

14. The composition as described in claim 1 , wherein said fatty acid ester is a glyceride of a fatty acid having 6-20 carbon atoms.

15. The composition as described in claim 1 , wherein said fatty acid ester is a mixture of two or more glycerides.

16. The composition as described in claim 1 , wherein said fatty acid ester is mixed with an oil vehicle other than fatty acid ester.

17. The composition as described in claim 16 , wherein said oil vehicle is a mineral oil.

18. The composition as described in claim 1 , wherein L is oxo.

19. The composition as described in claim 1 , wherein A is —COOH.

20. The composition as described in claim 1 , wherein X 1 and X 2 are both halogen.

21. The composition as described in claim 20 , wherein the halogen is fluorine.

22. The composition as described in claim 1 , wherein R 1 is C6-8 aliphatic hydrocarbon.

23. The composition as described in claim 1 , wherein R 1 is selected from the following group:

—CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —,

—CH 2 —CH═CH—CH 2 —CH 2 —CH 2 —,

—CH 2 —CH 2 —CH 2 —CH 2 —CH═CH—,

—CH 2 —C≡C—CH 2 —CH 2 —CH 2 —,

—CH 2 —CH 2 —CH 2 —CH 2 —CH(CH 3 )—CH 2 —,

—CH 2 —CH 2 —CH 2 —CH 2 —O—CH 2 —,

—CH 2 —CH═CH—CH 2 —O—CH 2 —,

—CH 2 —C≡C—CH 2 —O—CH 2 —,

—CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —,

—CH 2 —CH═CH—CH 2 —CH 2 —CH 2 —CH 2 —,

—CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH═CH—,

—CH 2 —C≡C—CH 2 —CH 2 —CH 2 —CH 2 —,

—CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH(CH 3 )—CH 2 —,

—CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —,

—CH 2 —CH═CH—CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —,

—CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH═CH—,

—CH 2 —C≡C—CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —, and

—CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH(CH 3 )—CH 2 —.

24. The composition as described in claim 1 , wherein R 1 is —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —.

25. The composition as described in claim 1 , which is in a dosage form suitable for oral administration.

26. The composition as described in claim 1 , which is formulated as a capsule.