IP Library Granted Patent US 7,582,284
Granted Patent B2
US 7,582,284 · App. 10/413,457 · Granted Sep 1, 2009

Particulate materials

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Quick Facts
Patent No.
US 7,582,284
App. No.
10/413,457
Granted
Sep 1, 2009
Kind
B2
Abstract

The present invention relates to active substances in particulate form, to methods for preparing them, to formulations containing them and to uses of such substances and formulations. A preferred embodiment is directed to particulate suspensions having improved flocculation behavior in a suspension vehicle, such as a hydrofluoroalkane propellant used in metered dose inhalers.

Claims (70)

1. A composition of an aerosol formulation, comprising:

a particulate active substance of non-micronized, solid particles having a mass median aerodynamic diameter of less than 10 μm, suspended in a nonsolvent hydrofluorocarbon fluid vehicle at a concentration within a range from about 0.2% w/v to about 5% w/v, which formulation exhibits a flocculation volume of about 85% or greater, about 1 minute after mixing the particulate active substance and the vehicle, wherein the particulate active substance comprises a compound selected from the group consisting of salmeterol xinafoate, budesonide, salbutamol sulfate, dihydroergotamine mesylate, risperidone-(9-hydroxy)-palmitate, bromocriptine mesylate, and derivatives thereof and the nonsolvent hydrofluorocarbon fluid vehicle comprises 1,1,1,2-tetrafluoroethane (HFA 134a) or 1,1,1,2,3,3,3-heptafluoropropane (HFA 227ea).

2. The composition of claim 1 , wherein the vehicle is 1,1,1,2-tetrafluoroethane.

3. The composition of claim 2 , wherein the particulate active substance is suitable for delivery by inhalation.

4. The composition of claim 3 , consisting essentially of the particulate active substance and the vehicle.

5. The composition of claim 1 , wherein the particulate active substance is suspended in the vehicle at a concentration within a range from about 0.2% w/v to about 3% w/v.

6. The composition of claim 1 , wherein the particulate active substance is suspended in the vehicle at a concentration within a range from about 0.5% w/v to about 1.5% w/v.

7. The composition of claim 1 , wherein the relative standard deviation in a quantity of the particulate active substance delivered in each dose is no more than 15% over 100 successive equal volume doses.

8. The composition of claim 1 , wherein the relative standard deviation in a fine particle fraction of the delivered doses is no more than 15% over 100 successive equal volume doses.

9. The composition of claim 1 , wherein the relative standard deviation in a fine particle fraction contained in each dose is no more than 17% over 100 successive equal volume doses.

10. The composition of claim 1 , wherein the relative standard deviation in the mass median aerodynamic diameter of the particulate active substance contained in each dose is no more than 9.5% over 100 successive equal volume doses.

11. The composition of claim 1 , wherein a fine particle fraction contained in each dose is at least 25% over 100 successive equal volume doses.

12. The composition of claim 1 , wherein the mass median aerodynamic diameter of the particulate active substance delivered in each dose is 4 μm or less over 100 successive equal volume doses.

13. The composition of claim 1 , which is stable after storage at 25° C. and 60% relative humidity for a period of at least 12 months.

14. The composition of claim 1 , wherein the flocculation volume is about 35% or greater, about 5 minutes after mixing the particulate active substance and the vehicle.

15. The composition of claim 14 , wherein the flocculation volume is about 50% or greater, about 5 minutes after mixing the particulate active substance and the vehicle.

16. The composition of claim 15 , wherein the flocculation volume is about 50% or greater, about 10 minutes after mixing the particulate active substance and the vehicle.

17. The composition of claim 1 , wherein the particulate active substance further comprises a mass median diameter of less than 15 microns.

18. The composition of claim 17 , wherein the particulate active substance further comprises a mass median diameter of less than 10 microns.

19. The composition of claim 18 , wherein the particulate active substance comprises a mass median diameter of less than 5 microns.

20. The composition of claim 19 , wherein the particulate active substance comprises a mass median diameter of less than 3 microns.

21. The composition of claim 1 , wherein the particulate active substance is in a crystalline form.

22. The composition of claim 21 , wherein the crystalline form is significantly longer in one dimension than in at least one other dimension.

23. The composition of claim 1 , wherein the particulate active substance contains less than 200 ppm of a residual solvent.

24. The composition of claim 1 , wherein the particulate active substance is suitable for systemic delivery via the lung.

25. The composition of claim 1 , wherein the particulate active substance comprises budesonide.

26. A composition of an aerosol formulation, comprising:

a particulate active substance of non-micronized, solid particles having a mass median aerodynamic diameter of less than 5 μm, suspended in a nonsolvent hydrofluorocarbon fluid vehicle at a concentration within a range from about 0.2% w/v to about 5% w/v, which formulation exhibits a flocculation volume of greater than 85%, about 60 seconds after mixing the particulate active substance and the vehicle, wherein the particulate active substance comprises a compound selected from the group consisting of salmeterol xinafoate, budesonide, salbutamol sulfate, dihydroergotamine mesylate, risperidone-(9-hydroxy)-palmitate, bromocriptine mesylate, and derivatives thereof and the nonsolvent hydrofluorocarbon fluid vehicle comprises 1,1,1,2-tetrafluoroethane (HFA 134a) or 1,1,1,2,3,3,3-heptafluoropropane (HFA 227ea).

27. The composition of claim 26 , wherein the flocculation volume is greater than 50%, about 2 minutes after mixing the particulate active substance and the vehicle.

28. The composition of claim 27 , wherein the flocculation volume is greater than 85%, about 2 minutes after mixing the particulate active substance and the vehicle.

29. A composition of an aerosol formulation, comprising:

a particulate active substance of non-micronized, solid particles having a mass median aerodynamic diameter of less than 10 μm; and

a suspension containing the particulate active substance suspended in a nonsolvent hydrofluorocarbon fluid vehicle at a concentration within a range from about 0.2% w/v to about 3% w/v, wherein the suspension exhibits a flocculation volume of about 35% or greater, 5 minutes after mixing the particulate active substance and the vehicle, wherein the particulate active substance comprises a compound selected from the group consisting of salmeterol xinafoate, budesonide, salbutamol sulfate, dihydroergotamine mesylate, risperidone-(9-hvdroxv)-palmitate, bromocriptine mesylate, and derivatives thereof and the nonsolvent hydrofluorocarbon fluid vehicle comprises 1,1,1,2-tetrafluoroethane (HFA 134a) or 1,1,1,2,3,3,3-heptafluoropropane (HFA 227ea).

30. A composition of an aerosol formulation, comprising:

a particulate active substance of non-micronized, solid particles having a mass median aerodynamic diameter of less than 10 μm; and

a suspension containing the particulate active substance suspended in a nonsolvent hydrofluorocarbon fluid vehicle and having a flocculation volume of about 85% or greater, about 1 minute after mixing the particulate active substance and the vehicle, wherein the particulate active substance comprises a compound selected from the group consisting of salmeterol xinafoate, budesonide, salbutamol sulfate, dihydroergotamine mesylate, risperidone-(9-hydroxv)-palmitate, bromocriptine mesylate, and derivatives thereof and the nonsolvent hydrofluorocarbon fluid vehicle comprises 1,1,1,2-tetrafluoroethane (HFA 134a) or 1,1,1,2,3,3,3-heptafluoropropane (HFA 227ea).

31. The composition of claim 30 , wherein the particulate active substance comprises salmeterol xinafoate or salbutamol sulfate.

32. The composition of claim 30 , wherein the particulate active substance comprises dihydroergotamine mesylate.

33. The composition of claim 1 , wherein the particulate active substance comprises salmeterol xinafoate or salbutamol sulfate.

34. The composition of claim 1 , wherein the particulate active substance comprises dihydroergotamine mesylate.

35. The composition of claim 26 , wherein the particulate active substance comprises salmeterol xinafoate or salbutamol sulfate.

36. The composition of claim 26 , wherein the particulate active substance comprises dihydroergotamine mesylate.

37. The composition of claim 29 , wherein the particulate active substance comprises salmeterol xinafoate or salbutamol sulfate.

38. The composition of claim 29 , wherein the particulate active substance comprises dihydroergotamine mesylate.

39. A composition of an aerosol formulation, comprising:

a particulate active substance of non-micronized, solid particles having a mass median diameter of less than 15 μm, suspended in a nonsolvent hydrofluorocarbon fluid vehicle at a concentration within a range from about 0.2% w/v to about 5% w/v, wherein the formulation exhibits a flocculation volume of 35% or greater, about 1 minute after mixing the particulate active substance and the vehicle, wherein the particulate active substance comprises a compound selected from the group consisting of salmeterol xinafoate. budesonide. salbutamol sulfate. dihydroergotamine mesylate, risperidone-(9-hydroxy)-palmitate, bromocriptine mesylate, and derivatives thereof and the nonsolvent hydrofluorocarbon fluid vehicle comprises 1,1,1,2-tetrafluoroethane (HFA 134a) or 1,1,1,2,3,3,3-heptafluoropropane (HFA 227ea).

40. The composition of claim 39 , wherein the vehicle is 1,1,1,2-tetrafluoroethane.

41. The composition of claim 40 , wherein the particulate active substance is suitable for delivery by inhalation.

42. The composition of claim 39 , wherein the particulate active substance is suspended in the vehicle at a concentration within a range from about 0.2% w/v to about 3% w/v.

43. The composition of claim 42 , wherein the particulate active substance is suspended in the vehicle at a concentration within a range from about 0.5% w/v to about 1.5 % w/v.

44. The composition of claim 39 , wherein the flocculation volume is greater than 50%, about 1 minute after mixing the particulate active substance and the vehicle.

45. The composition of claim 43 , wherein the flocculation volume is greater than 75%, about 1 minute after mixing the particulate active substance and the vehicle.

46. The composition of claim 39 , wherein the flocculation volume is greater than 50%, about 90 seconds after mixing the particulate active substance and the vehicle.

47. The composition of claim 46 , wherein the flocculation volume is greater than 50%, about 2 minutes after mixing the particulate active substance and the vehicle.

48. The composition of claim 47 , wherein the flocculation volume is greater than 50%, about 4 minutes after mixing the particulate active substance and the vehicle.

49. The composition of claim 48 , wherein the flocculation volume is greater than 50%, about 5 minutes after mixing the particulate active substance and the vehicle.

50. The composition of claim 39 , wherein the flocculation volume is greater than 85%, about 1 minute after mixing the particulate active substance and the vehicle.

51. The composition of claim 47 , wherein the flocculation volume is greater than 85%, about 2 minutes after mixing the particulate active substance and the vehicle.

52. The composition of claim 47 , wherein the flocculation volume is greater than 85%, about 5 minutes after mixing the particulate active substance and the vehicle.

53. The composition of claim 47 , wherein the flocculation volume is greater than 85%, about 8 minutes after mixing the particulate active substance and the vehicle.

54. The composition of claim 47 , wherein the flocculation volume is greater than 85%, about 10 minutes after mixing the particulate active substance and the vehicle.

55. The composition of claim 39 , wherein the mass median diameter is less than 10 microns.

56. The composition of claim 55 , wherein the mass median diameter is less than 5 microns.

57. The composition of claim 39 , wherein the particulate active substance is in a crystalline form.

58. The composition of claim 39 , wherein the particulate active substance comprises salmeterol xinafoate or salbutamol sulfate.

59. The composition of claim 39 , wherein the particulate active substance comprises dihydroergotamine mesylate.

60. A composition of an aerosol formulation, comprising:

a particulate active substance of non-micronized, solid particles having a mass median aerodynamic diameter of less than 5 μm, suspended in a nonsolvent hydrofluorocarbon fluid vehicle, wherein the formulation exhibits a flocculation volume of 50% or greater, 1 minute after mixing the particulate active substance and the vehicle, wherein the particulate active substance comprises a compound selected from the group consisting of salmeterol xinafoate, budesonide, salbutamol sulfate, dihydroergotamine mesylate, risperidone-(9-hydroxy)-palmitate, bromocriptine mesylate, and derivatives thereof and the nonsolvent hydrofluorocarbon fluid vehicle comprises 1,1,1,2-tetrafluoroethane (HFA 134a) or 1,1,1,2,3,3,3-heptafluoropropane (HFA 227ea).

61. The composition of claim 60 , wherein the particulate active substance comprises salmeterol xinafoate or salbutamol sulfate.

62. The composition of claim 60 , wherein the particulate active substance comprises dihydroergotamine mesylate.

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Apr 17, 2020
From: TC LENDING, LLC, AS COLLATERAL AGENT
To: NEKTAR THERAPEUTICS
Reel/Frame 053180/0009 →
RELEASE OF SECURITY INTEREST RECORDED AT REEL 28571, FRAME 0141 Recorded Oct 14, 2015
From: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: NEKTAR THERAPEUTICS
Reel/Frame 036866/0700 →
GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS Recorded Oct 6, 2015
From: NEKTAR THERAPEUTICS
To: TC LENDING, LLC, AS COLLATERAL AGENT
Reel/Frame 036796/0562 →
GRANT OF SECURITY INTEREST Recorded Jul 17, 2012
From: NEKTAR THERAPEUTICS
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 028571/0141 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 22, 2012
From: NEKTAR THERAPEUTICS UK, LTD.
To: NEKTAR THERAPEUTICS
Reel/Frame 027912/0187 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 14, 2003
From: KORDIKOWSKI, ANDREAS; WALKER, STEPHEN ERNEST; YORK, PETER
To: NEKTAR THERAPEUTICS UK, LTD.
Reel/Frame 013797/0388 →