Growth stimulating factors

• US 5,955,624 A
• Filed: 06/07/1995
• Issued: 09/21/1999
• Est. Priority Date: 08/03/1994
• Status: Expired due to Fees

• Current Assignee: Cell Therapeutics, Inc.
• Original Assignee: Cell Therapeutics, Inc.
• Inventors: Hakomori, Sen-Itiroh, Nudelman, Edward
• Primary Examiner(s): Geist, Gary
• Assistant Examiner(s): Carr, Deborah D.
• Application Number:
  US08/473,901
• Time in Patent Office: 1,567 Days
• Field of Search: 554/227, 514/546, 514/547, 514/549, 514/552, 514/715, 514/722, 514/723
• US Class Current: 554/227
• CPC Class Codes: A61K 2300/00 Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
• CPC Class Codes: A61K 31/047 having two or more hydroxy groups, e.g. sorbitol
• CPC Class Codes: A61K 31/075 Ethers or acetals
• CPC Class Codes: A61K 31/08 acyclic, e.g. paraformaldehyde
• CPC Class Codes: A61K 31/121 acyclic
• CPC Class Codes: A61K 31/23 of acids having a carboxyl group bound to a chain of seven or more carbon atoms
• CPC Class Codes: A61K 31/231 having one or two double bonds
• CPC Class Codes: A61K 31/232 having three or more double bonds, e.g. etretinate
• CPC Class Codes: A61K 31/365 Lactones
• CPC Class Codes: A61K 31/445 Non condensed piperidines, e.g. piperocaine
• CPC Class Codes: A61K 31/47 Quinolines; Isoquinolines
• CPC Class Codes: A61K 31/57 substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
• CPC Class Codes: A61K 31/685 one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
• CPC Class Codes: A61K 31/7012 Compounds having a free or esterified carboxyl group attached, directly or through a carbon chain, to a carbon atom of the saccharide radical, e.g. glucuronic acid, neuraminic acid gluconic acid A61K31/191; ascorbic acid A61K31/375
• CPC Class Codes: A61K 38/13 Cyclosporins
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca

Abstract

Alk-1-enyl glycerol derivatives and method of preparing same. The derivatives stimulate cell and tissue growth.

Claims

1. A pharmaceutical composition comprising an angiogenic effective amount of an isolated alk-1-enyl glycerol derivative of the formula:

##STR15## wherein n is 0-23 and X and Y are independently H or an acyl group having from 2 to 26 carbon atoms, and a pharmaceutically acceptable carrier, diluent or exipient.

2. The pharmaceutical composition of claim 1, wherein n is 13 or 15.

3. The pharmaceutical composition of claim 1, wherein X is an acyl group and Y is H.

4. The pharmaceutical composition of claim 3, wherein said acyl group comprises 20 carbon atoms.

5. The pharmaceutical composition of claim 4, wherein said 20 carbon atom acyl group is an arachidonate group.

6. The pharmaceutical composition of claim 1, wherein X and Y arc acyl groups.

7. The pharmaceutical composition of claim 6, wherein Y comprises 20 carbon atoms.

8. The pharmaceutical composition of claim 7, wherein said 20 carbon atom acyl group is an arachidonate group.

9. The pharmaceutical composition of claim 7, wherein X is an acyl group comprising 16 or 18 carbon atoms.

10. The pharmaceutical composition of claim 8, wherein X is an acyl group comprising 16 or 18 carbon atoms.

11. The pharmaceutical composition of claim 1, wherein X and Y are both H.

12. The pharmaceutical composition of claim 11, wherein n is 13 or 15.

13. The pharmaceutical composition of claim 1, wherein Y is an acyl group and X is a H.

14. The pharmaceutical composition of claim 13, wherein said acyl group comprises 20 carbon atoms.

15. The pharmaceutical composition of claim 14, wherein said 20 carbon atom acyl group is an arachidonate group.

16. A pharmaceutical composition comprising an angiogenic effective amount of an isolated alk-1-enyl glycerol derivative of the formula:

##STR16## wherein n is 0-23 and X and Y are independently H or an acyl group having from 2 to 26 carbon atoms, a pharmaceutically acceptable carrier, diluent or excipient and a potentiator, wherein the potentiator stimulates activity of the alk-1-enyl glycerol derivatives.

17. The pharmaceutical composition of claim 16, wherein n is 13 or 15.

18. The pharmaceutical composition of claim 16, wherein X is an acyl group and Y is H.

19. The pharmaceutical composition of claim 18, wherein said acyl group comprises 20 carbon atoms.

20. The pharmaceutical composition of claim 19, wherein said 20 carbon atom acyl group is an arachidonate group.

21. The pharmaceutical composition of claim 16, wherein X and Y are acyl groups.

22. The pharmaceutical composition of claim 21, wherein Y comprises 20 carbon atoms.

23. The pharmaceutical composition of claim 22, wherein said 20 carbon atom acyl group is an arachidonate group.

24. The pharmaceutical composition of claim 22, wherein X is an acyl group comprising 16 or 18 carbon atoms.

25. The pharmaceutical composition of claim 16, wherein X and Y are both H.

26. The pharmaceutical composition of claim 25, wherein n is 13 or 15.

27. The pharmaceutical composition of claim 16, wherein Y is an acyl group and X is a H.

28. The pharmaceutical composition of claim 27, wherein said acyl group comprises 20 carbon atoms.

29. The pharmaceutical composition of claim 28, wherein said 20 carbon atom acyl group is an arachidonate group.

30. The pharmaceutical composition of claim 16, wherein the potentiator is a glycerol phospholipid or a disialyl ganglioside.

31. The pharmaceutical composition of claim 30, wherein the potentiator is a disialyl ganglioside.

32. The pharmaceutical composition of claim 31, wherein said disialyl ganglioside is GD₃.

33. The pharmaceutical composition of claim 16, wherein the potentiator is a glycerol phospholipid.

34. The pharmaceutical composition of claim 33, wherein said glycerol phospholipid is lysophosphatidyl serine.

35. The pharmaceutical composition of claim 33, wherein X and Y are both H and n is 13 or 15.