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Claims for Patent: 5,134,127

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Claims for Patent: 5,134,127

Title: Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof
Abstract:Sulfoalkyl ether cyclodextrin derivatives and their use as solubilizing agents for water insoluble drugs for oral, intranasal, or parenteral administration are disclosed.
Inventor(s): Stella; Valentino (Lawrence, KS), Rajewski; Roger (Lawrence, KS)
Assignee: University of Kansas (Lawrence, KS)
Application Number:07/469,087
Patent Claims: 1. A purified cyclodextrin derivative composition which comprises a cyclodextrin derivative of formula ##STR3## wherein: n is 4, 5 or 6;

R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are each, independently, O.sup.- or a O--(C.sub.2-6 alkylene)--SO.sub.3.sup.- group, and at least one of R.sub.1 and R.sub.2 is, independently, said O--(C.sub.2-6 alkylene)--SO.sub.3.sup.- group; and

S.sub.1, S.sub.2, S.sub.3, S.sub.4, S.sub.5, S.sub.6, S.sub.7, S.sub.8 and S.sub.9 are each, independently, a pharmaceutically acceptable cation, and wherein said composition shows an absence of underivatized cyclodextrin as measured by thin-layer chromatography.

2. The composition of claim 1, wherein R.sub.1, R.sub.2 and R.sub.3 are each, independently, said O--(C.sub.2-6 -alkylene)--SO.sub.3.sup.- group.

3. The composition of claim 1, wherein at least one of R.sub.1, R.sub.2 and R.sub.3 is, independently, a O--(CH.sub.2).sub.m --SO.sub.3.sup.- group, wherein m is 2, 3, 4, 5 or 6.

4. The composition of claim 1, wherein R.sub.1, R.sub.2 and R.sub.3 are each, independently a O--(CH.sub.2).sub.m --SO.sub.3.sup.- group, wherein m is 3 or 4.

5. The composition of claim 1, wherein:

at least one of R.sub.4, R.sub.6 and R.sub.8 is, independently, said O--(C.sub.2-6 -alkylene)--SO.sub.3.sup.- group; and

R.sub.5, R.sub.7 and R.sub.9 are all O.sup.-.

6. The composition of claim 2, wherein

at least one of R.sub.4, R.sub.6 and R.sub.8 is, independently, said O--(C.sub.2-6 -alkylene)--SO.sub.3.sup.- group; and

R.sub.5, R.sub.7 and R.sub.9 are all O.sup.-.

7. The composition of claim 2, wherein:

R.sub.4, R.sub.6 and R.sub.8 are each a O--(C.sub.2-6 -alkylene)--SO.sub.3.sup.- group; and

R.sub.5, R.sub.7 and R.sub.9 are all O.sup.-.

8. A composition comprising a drug complexed to a cyclodextrin derivative of formula (2): ##STR4## wherein: n=4, 5 or 6;

R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, and R.sub.9 are each at least one of R.sub.1 and R.sub.2 is, independently, said O--(C .sub.2-6 alkylene)--SO.sub.3.sup.- group; and

S.sub.1 to S.sub.9 are each, independently, a pharmaceutically acceptable cation;

wherein said composition contains not more than 5 wt. % of underivatized cyclodextrin.

9. The composition of claim 8, wherein R.sub.1, R.sub.2 and R.sub.3 are each, independently, said O--(C.sub.2-6 -alkylene)--SO.sub.3.sup.- group.

10. The composition of claim 8, wherein:

at least one of R.sub.4, R.sub.6 and R.sub.8 is, independently, said O--(C.sub.2-6 -alkylene)--SO.sub.3.sup.- group; and

R.sub.5, R.sub.7 and R.sub.9 are all O.sup.-.

11. The composition of claim 9, wherein:

at least one of R.sub.4, R.sub.6 and R.sub.8 is, independently, said O--(C.sub.2-6 -alkylene)--SO.sub.3.sup.- group; and

R.sub.5, R.sub.7 and R.sub.9 are all O.sup.-.

12. The composition of claim 11, wherein R.sub.4, R.sub.6 and R.sub.8 are each, independently, said O--(C.sub.2-6 -alkylene)--SO.sub.3.sup.- group.

13. The composition of claim 8, wherein said drug is one member selected from the group consisting of amobarbital, ampicillin, aspirin, beclomethasone, benzocaine, benzodiazepines, betamethasone, chlorambucil, chloramphenicol, chlorpromazine, clofibrate, coenzyme A, cortisone, cortisone acetate, cyclobarbital, dexamethasone, dexamethasone acetate, diazepam, digitoxon, digoxin, estradiol, 5-fluorouracil, flurbiprofen, griseofulvin, hydrocortisone, hydrocortisone acetate, ibuprofen, indomethanin, ketoprofen, methicillin, metronidazole, mitomycin, nitrazepam, nitroglycerin, penecillin, pentobarbital, phenopbarbital, phenobarbitone, phenyltoin, prednisolone, predisolone acetate, progesterone, prostaglandin A series, prostaglandin B series, prostaglandin E series, prostaglandin F series, reserpine, sulfacetamide sodium, testosterone, vitamin A, vitamin D3, vitamin E, vitamin K3, and warfarin.

14. A pharmaceutically acceptable composition comprising a pharmaceutically acceptable carrier and a clathrate complex comprising a drug complexed to a cyclodextrin derivative of formula (2): ##STR5## wherein: n=4, 5 or 6;

R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are each independently O.sup.- or a O--(C.sub.2-6 alkylene)--SO.sub.3.sup.- group, and at least one of R.sub.1 and R.sub.2 is, independently, said O--(C.sub.2-6 alkylene)--SO.sub.3.sup.- group; and

S.sub.1 to S.sub.9 are each, independently, a pharmaceutically acceptable cation;

wherein said composition contains not more than 5 wt. % of underivatized cyclodextrin.

15. The composition of claim 14, wherein said carrier is a parenterally suitable carrier.

16. A delayed release pharmaceutical composition, comprising a drug complexed to a purified cyclodextrin derivative of formula (2): ##STR6## wherein: n=4, 5 or 6;

R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are each independently O.sup.- or a O--(C.sub.2-6 alkylene)SO.sub.3.sup.- group, and at least one of R.sub.1 and R.sub.2 is, independently said O--(C.sub.2-6 alkylene)--SO.sub.3.sup.- group; and

S.sub.1 to S.sub.9 are each, independently, a pharmaceutically acceptable cation.

17. The composition according to claim 1, wherein n is 5.

18. The composition according to claim 17, wherein said C.sub.2-6 alkylene is a C.sub.3 alkylene.

19. The composition according to claim 17, wherein said C.sub.2-6 is a C.sub.4 alkylene.

20. The composition according to claim 18, wherein said cyclodextrin derivatives in said composition contain an average of about one O--(C.sub.2 -C.sub.6 alkylene)--SO.sub.3.sup.- group per cyclodextrin molecule.

21. The composition according to claim 18, wherein said cyclodextrin derivatives in said composition contain an average of about 3.6 O--(C.sub.2 -C.sub.6 alkylene)--SO.sub.3.sup.- group per cyclodextrin molecule.

22. The composition according to claim 18, wherein said cyclodextrin derivatives in said composition contain an average of about 7 O--(C.sub.2 -C.sub.6 alkylene)--SO.sub.3.sup.- group per cyclodextrin molecule.

23. The composition according to claim 19, wherein said cyclodextrin derivatives in said composition contain an average of about one O--(C.sub.2 -C.sub.6 alkylene)--SO.sub.3.sup.- group per cyclodextrin molecule.

24. The composition according to claim 19, wherein said cyclodextrin derivatives in said composition contain an average of about 4.7 O--(C.sub.2 -C.sub.6 alkylene)--SO.sub.3.sup.- group per cyclodextrin molecule.

25. The composition according to claim 19, wherein said cyclodextrin derivatives in said composition contain an average of about 7 O--(C.sub.2 -C.sub.6 alkylene)--SO.sub.3.sup.- group per cyclodextrin molecule.

26. The composition according to claim 1, wherein said composition contains less than 5% underivatized cyclodextrin.

27. The composition according to claim 26, wherein said composition contains less than 2% underivatized cyclodextrin.

28. The composition according to claim 2, wherein said composition contains less than 5% underivatized cyclodextrin.

29. The composition according to claim 28, wherein said composition contains less than 2% underivatized cyclodextrin.

30. The composition according to claim 17, wherein said composition contains less than 5% .beta.-cyclodextrin.

31. The composition according to claim 30, wherein said composition contains less than 2% .beta.-cyclodextrin.

32. The composition according to claim 18, wherein said composition contains less than 5% .beta.-cyclodextrin.

33. The composition according to claim 32, wherein said composition contains less than 2% .beta.-cyclodextrin.

34. The composition according to claim 19, wherein said composition contains less than 5% .beta.-cyclodextrin.

35. The composition according to claim 34, wherein said composition contains less than 2% .beta.-cyclodextrin.

36. The composition according to claim 8, wherein n is 5.

37. The composition according to claim 36, wherein said C.sub.2-6 alkylene is a C.sub.3 alkylene.

38. The composition according to claim 36, wherein said C.sub.2-6 is a C.sub.4 alkylene.

39. The composition according to claim 37, wherein said cyclodextrin derivatives in said composition contain an average of about 1, 3.6 or 7 O--(C.sub.2 -C.sub.6 alkylene)--SO.sub.3.sup.- groups per cyclodextrin molecule.

40. The composition according to claim 38, wherein said cyclodextrin derivatives in said composition contain an average of about 1, 4.7 or 7 O--(C.sub.2 -C.sub.6 alkylene)--SO.sub.3.sup.- groups per cyclodextrin molecule.

41. The composition according to claim 14, wherein n is 5.

42. The composition according to claim 14, wherein C.sub.2-6 alkylene is a C.sub.3 alkylene.

43. The composition according to claim 19, wherein said C.sub.2-6 is a C.sub.4 alkylene.

44. The composition according to claim 42, wherein said cyclodextrin derivatives in said composition contain an average of about 1, 3.6 or 7 O--(C.sub.2 -C.sub.6 alkylene)--SO.sub.3.sup.- groups per cyclodextrin molecule.

45. The composition according to claim 43, wherein said cyclodextrin derivatives in said composition contain an average of about 1, 4.7 or 7 O--(C.sub.2 -C.sub.6 alkylene)--SO.sub.3.sup.- groups per cyclodextrin molecule.
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