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Details for Patent: 5,900,475

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Details for Patent: 5,900,475

Title: Hydrophobic sequestrant for cholesterol depletion
Abstract:The present invention relates to a poly(allylamine) polymer and, more generally, a hydrocarbon amine polymer. Preferably, these polymers are crosslinked. The present invention also relates to methods of forming these polymers and methods for their use. Further, the present invention relates to alkylating agents that can be employed to form the polymers and to methods for forming the alkylating agents Generally, the polymer sequestrant includes a substituent bound to an amine of the polymer. The substituent includes a quaternary amine-containing moiety having one, two or three terminal hydrophobic substituents. A method of preparing quaternary amine-containing alkylating agents includes reacting an unsymmetrical dihalide with a tertiary amine having at least one hydrophobic substituent. A method for binding bile salts of bile acids in a mammal includes orally administering to the mammal a therapeutically-effective amount of the polymer sequestrant.
Inventor(s): Mandeville, III; W. Harry (Lynnfield, MA), Holmes-Farley; Stephen Randall (Arlington, MA), Petersen; John S. (Acton, MA)
Assignee: GelTex Pharmaceuticals, Inc. (Waltham, MA)
Filing Date:Jun 06, 1996
Application Number:08/659,264
Claims:1. A crosslinked poly(allylamine) polymer, comprising a substituent bound to an amine of said polymer, the substituent including a quaternary amine-containing moiety, wherein a quaternary amine nitrogen of said moiety is bound to the amine of the polymer by an alkylene having three or more carbons and wherein at least one of three terminal substituents of the quaternary amine is a hydrophobic alkyl group having from six to about twenty-four carbons and the remaining terminal substituents are each independently an alkyl group having between one and about five carbons.

2. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has three carbons, the hydrophobic alkyl group is an octyl group and the remaining terminal substituents are methyl groups.

3. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has three carbons, the hydrophobic alkyl group is a decyl group and the remaining terminal substituents are methyl groups.

4. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has three carbons, the hydrophobic alkyl group is a dodecyl group and the remaining terminal substituents are methyl groups.

5. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has four carbons, the hydrophobic alkyl group is an octyl group and the remaining terminal substituents are methyl groups.

6. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has four carbons, the hydrophobic alkyl group is a decyl group and the remaining terminal substituents are methyl groups.

7. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has four carbons, the hydrophobic alkyl group is a dodecyl group and the remaining terminal substituents are methyl groups.

8. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has five carbons, the hydrophobic alkyl group is an octyl group and the remaining terminal substituents are methyl groups.

9. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has five carbons, the hydrophobic alkyl group is a decyl group and the remaining terminal substituents are methyl groups.

10. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has five carbons, the hydrophobic alkyl group is a dodecyl group and the remaining terminal substituents are methyl groups.

11. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has six carbons, the hydrophobic alkyl group is an octyl group and the remaining terminal substituents are methyl groups.

12. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has six carbons, the hydrophobic alkyl group is a decyl group and the remaining terminal substituents are methyl groups.

13. The crosslinked poly(allylamine) polymer of claim 1, wherein said alkylene has six carbons, the hydrophobic alkyl group is a dodecyl group and the remaining terminal substituents are methyl groups.

14. A crosslinked poly(allylamine) polymer formed by a method comprising the step of reacting a crosslinked poly(allylamine) with a quaternary amine-containing compound having the formula ##STR11## wherein, R represents an alkyl group, at least one of which has from six to about twenty-four carbons and the remainder of which each independently have from one to about five carbons,

n is an integer having a value of three or more,

X is a leaving group, and

Y is a negatively-charged counterion.

15. The crosslinked poly(allylamine) polymer of claim 14, wherein n is from 3 to about 6.

16. The crosslinked poly(allylamine) polymer of claim 15, wherein n is 3, at least one alkyl is an octyl group and the remaining alkyl groups are methyl groups.

17. The crosslinked poly(allylamine) polymer of claim 15, wherein n is 3, at least one alkyl is a decyl group and the remaining alkyl groups are methyl groups.

18. The crosslinked poly(allylamine) polymer of claim 15, wherein n is 3, at least one alkyl group is a dodecyl group and the remaining alkyl groups are methyl groups.

19. The crosslinked poly(allylamine) polymer of claim 15, wherein n is 4, at least one alkyl group is an octyl group and the remaining alkyl groups are methyl groups.

20. The crosslinked poly(allylamine) polymer of claim 15, wherein n is 4, at least one alkyl group is a decyl group and the remaining alkyl groups are methyl groups.

21. The crosslinked poly(allylamine) polymer of claim 15, wherein n is 4, at least one alkyl group is a dodecyl group and the remaining alkyl groups are methyl groups.

22. The crosslinked poly(allylamine) polymer of claim 15, wherein n is 5, at least one alkyl group is an octyl group and the remaining alkyl groups are methyl groups.

23. The crosslinked poly(allylamine) polymer of claim 15, wherein n is 5, at least one alkyl group is a decyl group and the remaining alkyl groups are methyl groups.

24. The crosslinked poly(allylamine) polymer of claim 15, wherein n is 5, at least one alkyl group is a dodecyl group and the remaining alkyl groups are methyl. groups.

25. The crosslinked poly(allylamine) polymer of claim 15, wherein n is 6, at least one alkyl group is an octyl group and the remaining alkyl groups are methyl groups.

26. The crosslinked poly(allylamine) polymer of claim 15 wherein n is 6, at least one alkyl is a decyl group and the remaining alkyl groups are methyl groups.

27. The crosslinked poly(allylamine) polymer of claim 15, wherein n is 6, at least one alkyl group is a dodecyl group and the remaining alkyl groups are methyl groups.

28. A hydrocarbon amine polymer, comprising a substituent bound to an amine of said polymer, the substituent including a quaternary amine-containing moiety, wherein a quaternary amine nitrogen of said moiety is bound to the amine of the polymer by an alkylene having three or more carbons and wherein at least two of three terminal substituents of the quaternary amine are each a hydrophobic alkyl group having from six to about twenty-four carbons and the other terminal substituent is an alkyl group having from one to about five carbons.

29. The hydrocarbon amine polymer of claim 28, wherein the polymer is crosslinked.

30. A hydrocarbon amine polymer, comprising a substituent bound to an amine of said polymer, the substituent including a quaternary amine-containing moiety, wherein a quaternary amine nitrogen of said moiety is bound to the amine of the polymer by an alkylene having three or more carbons and wherein three terminal substituents of the quaternary amine are hydrophobic alkyl groups having from six to about twenty-four carbons.

31. The hydrocarbon amine polymer of claim 30, wherein the polymer is crosslinked.

32. A crosslinked hydrocarbon amine polymer formed by a method comprising the step of reacting a crosslinked hydrocarbon amine polymer with a quaternary amine-containing compound having the formula: ##STR12## wherein, R represents an alkyl group, at least one of which has from six to about twenty-four carbons, and the remainder of which each independently have from one to about five carbons,

n is an integer having a value of three or more,

X is a leaving group, and

Y is a negatively-charged counterion.

33. The crosslinked hydrocarbon amine polymer of claim 32, wherein the polymer is a poly(vinylamine) polymer.

34. The crosslinked hydrocarbon amine polymer of claim 32, wherein the polymer is a poly(allylamine) polymer.

35. The crosslinked hydrocarbon amine polymer of claim 32, wherein the polymer is a poly(ethylenimine) polymer.

36. A method for binding bile salts in a mammal, comprising the step of orally administering to the mammal a therapeutic amount of a crosslinked poly(allylamine) polymer having a substituent bound to an amine of said polymer, the substituent including a quaternary amine-containing moiety, wherein a quaternary amine nitrogen of said moiety is bound to the amine of the polymer by an alkylene having three or more carbons and wherein at least one of three terminal substituents of the quaternary amine is a hydrophobic alkyl group having from six to about twenty-four carbons and the remaining terminal substituents are each independently an alkyl group having from one to about five carbons.

37. A method for binding bile salts in a mammal, comprising the step of orally administering to the mammal a therapeutic amount of a hydrocarbon amine polymer having a substituent bound to an amine of said polymer, the substituent including a quaternary amine containing moiety, wherein a quaternary amine nitrogen of said moiety is bound to the amine of the polymer by an alkylene having three or more carbons and wherein at least two of three terminal substituents of the quaternary amine are hydrophobic alkyl groups having from six to about twenty-four carbons and the remaining terminal substituent is an alkyl group having from one to about five carbons.

38. A method for reducing blood cholesterol in a mammal, comprising the step of orally administering to the mammal a therapeutic amount of a crosslinked poly(allylamine) polymer having a substituent bound to an amine of said polymer, the substituent including a quaternary amine-containing moiety, wherein a quaternary amine nitrogen of said moiety is bound to the amine of the polymer by an alkylene having three or more carbons and wherein at least one of three terminal substituents of the quaternary amine is a hydrophobic alkyl group having from six to about twenty-four carbons and the remaining terminal substituents are each independently an alkyl group having from one to about five carbons.

39. A method for treating atherosclerosis in a mammal, comprising the step of orally administering to the mammal a therapeutic amount of a crosslinked poly(allylamine) polymer having a substituent bound to an amine of said polymer, the substituent including a quaternary amine-containing moiety, wherein a quaternary amine nitrogen of said moiety is bound to the amine of the polymer by an alkylene having three or more carbons and wherein at least one of three terminal substituents of the quaternary amine is a hydrophobic alkyl group having from six to about twenty-four carbons and the remaining terminal substituents are each independently an alkyl group having from one to about five carbons.

40. A method for treating hypercholesterolemia in a mammal, comprising the step of orally administering to the mammal a therapeutic amount of a crosslinked poly(allylamine) polymer having a substituent bound to an amine of said polymer, the substituent including a quaternary amine-containing moiety, wherein a quaternary amine nitrogen of said moiety is bound to the amine of the polymer by an alkylene having three or more carbons and wherein at least one of three terminal substituents of the quaternary amine is a hydrophobic alkyl group having from six to about twenty-four carbons and the remaining terminal substituents are each independently an alkyl group having between one and about five carbons.

41. A method for reducing plasma lipid content of a mammal, comprising the step of orally administering to the mammal a therapeutic amount of a crosslinked poly(allylamine) polymer having a substituent bound to an amine of said polymer, the substituent including a quaternary amine-containing moiety, wherein a quaternary amine nitrogen of said moiety is bound to the amine of the polymer by an alkylene having three or more carbons and wherein at least one of three terminal substituents of the quaternary amine is a hydrophobic alkyl group having between six and about twenty-four carbons and the remaining terminal substituents are each independently an alkyl group having from one to about five carbons.

42. A poly(allylamine) polymer, comprising a substituent bound to an amine of said polymer, the substituent including a quaternary amine-containing moiety, wherein a quaternary amine nitrogen of said moiety is bound to the amine of the polymer by an alkylene having three or more carbons and wherein at least one of three terminal substituents of the quaternary amine is a hydrophobic alkyl group having from six to about twenty-four carbons and the remaining terminal substituents are each independently an alkyl group having from one to about five carbons.

43. The poly(allylamine) polymer of claim 42, wherein said alkylene has three carbons, the hydrophobic alkyl group is an octyl group and the remaining terminal substituents are methyl groups.

44. The poly(allylamine) polymer of claim 42, wherein said alkylene has three carbons, the hydrophobic alkyl group is a decyl group and the remaining terminal substituents are methyl groups.

45. The poly(allylamine) polymer of claim 42, wherein said alkylene has three carbons, the hydrophobic alkyl group is a dodecyl group and the remaining terminal substituents are methyl groups.

46. The poly(allylamine) polymer of claim 42, wherein said alkylene has four carbons, the hydrophobic alkyl group is a octyl group and the remaining terminal substituents are methyl groups.

47. The poly(allylamine) polymer of claim 42, wherein said alkylene has four carbons, the hydrophobic alkyl group is a decyl group and the remaining terminal substituents are methyl groups.

48. The poly(allylamine) polymer of claim 42, wherein said alkylene has four carbons, the hydrophobic alkyl group is an dodecyl group and the remaining terminal substituents are methyl groups.

49. The poly(allylamine) polymer of claim 42, wherein said alkylene has five carbons, the hydrophobic alkyl group is an octyl group and the remaining terminal substituents are methyl groups.

50. The poly(allylamine) polymer of claim 42, wherein said alkylene has five carbons, the hydrophobic alkyl group is a decyl group and the remaining terminal substituents are methyl groups.

51. The poly(allylamine) polymer of claim 42, wherein said alkylene has five carbons, the hydrophobic alkyl group is a dodecyl group and the remaining terminal substituents are methyl groups.

52. The poly(allylamine) polymer of claim 42, wherein said alkylene has six carbons, the hydrophobic alkyl group is an octyl group and the remaining terminal substituents are methyl groups.

53. The poly(allylamine) polymer of claim 42, wherein said alkylene has six carbons, the hydrophobic alkyl group is a decyl group and the remaining terminal substituents are methyl groups.

54. The poly(allylamine) polymer of claim 42, wherein said alkylene has six carbons, the hydrophobic alkyl group is a dodecyl group and the remaining terminal substituents are methyl groups.
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