IP Library › Granted Patent US 8,741,877
Granted Patent B2
US 8,741,877 · App. 13/778,038 · Granted Jun 3, 2014

Polylactides compositions and uses thereof

Inventors: Michael Moller (Geneva, CH); Thomas Trimaille (Marseilles, FR); Robert Gurny (Geneva, CH)
Assignee: University of Geneva
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Quick Facts
Patent No.
US 8,741,877
App. No.
13/778,038
Granted
Jun 3, 2014
Kind
B2
Abstract

The present invention provides compositions and methods relating to polylactides which may be used for drug delivery (e.g., parenteral delivery), wherein an organic solvent is not required.

Claims (42)

1. A method of drug delivery, comprising administering a pharmaceutical composition comprising a drug and a polylactide to a subject, wherein the polylactide has the structure:

wherein R 1 , R 2 , R 3 , and R 4 are each independently chosen from the group consisting of unsubstituted C 1-20 alkyl, H, C 2-20 alkenyl, and —(CH 2 ) y —(C 6 H 5 ); wherein y=1-20; wherein n is 2 to 100; wherein X is hydrogen or —C(O)—CH═CH 2 ; wherein at least one of R 1 , R 2 , R 3 , and R 4 is C 4-20 unsubstituted alkyl, C 2-20 alkenyl, or —(CH 2 ) y —(C 6 H 5 ); wherein y=1-20; wherein Y is —OH, C 1-12 alkoxy, benzyloxy, or —O—(CH 2 —CH 2 —O) p —CH 3 ; wherein p is 1 to 700; and

wherein if Y is —OH, C 1-12 alkoxy, or benzyloxy, then the polylactide has a Tg value of less than 15° C.

2. The method of claim 1 , wherein the pharmaceutical composition is formulated for parenteral, oral, topical, buccal, rectal, sublingual, intravenous, intradermal, transdermal, intrathecal, intraarterial, intraperitoneal, intranasal, mucosal, intravaginal, intrarectal, intramuscular, inhalation, injection, infusion, subcutaneous, or topical administration.

3. The method of claim 2 , wherein the pharmaceutical composition is formulated for parenteral injection.

4. The method of claim 2 , wherein the pharmaceutical composition is formulated for topical administration.

5. The method of claim 4 , wherein the pharmaceutical composition is formulated as an ointment, paste, or cream.

6. The method of claim 2 , wherein the pharmaceutical composition is formulated for oral administration.

7. The method of claim 2 , wherein the pharmaceutical composition is formulated as a powder or a tablet.

8. The method of claim 1 , wherein n is 2 to 75.

9. The method of claim 8 , wherein n is 2 to 50.

10. The method of claim 1 , wherein Y is —OH.

11. The method of claim 1 , wherein Y is —O—(CH 2 —CH 2 —O) p —CH 3 .

12. The method of claim 11 , wherein p is 1 to 250.

13. The method of claim 8 , wherein R 1 and R 3 are hydrogen; and R 2 and R 4 are C 4-20 alkyl.

14. The method of claim 13 , wherein R 2 and R 4 are —(CH 2 ) m —CH 3 , wherein m is from 3-19.

15. The method of claim 14 , wherein m is from 3 to 12.

16. The method of claim 1 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —(CH 2 ) m —CH 3 or —CH 3 , wherein m=3-12.

17. The method of claim 16 , wherein m=3-9.

18. The method of claim 1 , wherein m=4-6.

19. The method of claim 1 , wherein m=5.

20. The method of claim 9 , wherein n is 2 to 25.

21. The method of claim 1 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —(CH 2 ) m —CH 3 , wherein m=3-12.

22. The method of claim 1 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —CH 2 —(C 6 H 5 ) or —CH 3 .

23. The method of claim 1 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —CH 2 —(C 6 H 5 ).

24. The method of claim 1 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —CH(CH 3 ) 2 or —CH 3 .

25. The method of claim 1 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —(CH 2 ) 3 —CH 3 or —CH 3 .

26. The method of claim 1 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —(CH 2 ) 5 —CH 3 or —CH 3 .

27. The method of claim 26 , wherein the pharmaceutical composition is formulated for parenteral injection, rectal administration, topical administration, or oral administration.

28. The method of claim 1 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —(CH 2 ) 5 —CH 3 .

29. The method of claim 1 , wherein the subject is a mammal.

30. The method of claim 29 , wherein the mammal is a human.

31. The method of claim 29 , wherein the pharmaceutical composition is administered via parenteral injection, orally, topically, buccally, rectally, sublingually, intravenously, intradermally, intrathecally, intraarterially, intraperitoneally, intranasally, intravaginally, intramuscularly, subcutaneously, mucosally, via inhalation, via injection, via an infusion, via a catheter, via a lavage, in a creme, or in a lipid composition.

32. The method of claim 31 , wherein the pharmaceutical composition is administered via injection.

33. The method of claim 31 , wherein the pharmaceutical composition is administered topically.

34. The method of claim 31 , wherein the pharmaceutical composition is administered rectally or orally.

35. The method of claim 31 , wherein Y is —OH.

36. The method of claim 35 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —(CH 2 ) 5 —CH 3 or —CH 3 .

37. The method of claim 35 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —(CH 2 ) 5 —CH 3 .

38. The method of claim 1 , wherein Y is —O—(CH 2 —CH 2 —O) p —CH 3 .

39. The method of claim 38 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —(CH 2 ) 5 —CH 3 or —CH 3 .

40. The method of claim 38 , wherein R 1 and R 3 are hydrogen; and wherein R 2 and R 4 are —(CH 2 ) 5 —CH 3 .

Continuity (4)
Continuation 11912102
Provisional Application 60674103 · Apr 22, 2005
Provisional Application 60750141 · Dec 14, 2005
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