Levalbuterol salt

US 20040115136A1
Filed: 12/08/2003
Published: 06/17/2004
Est. Priority Date: 12/10/2002
Status: Active Grant

First Claim

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1. Levalbuterol L-tartrate.

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Abstract

Levalbuterol L-tartrate affords crystals possessing properties desirable for use in a metered dose inhaler.

7 Citations

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29 Claims

1. Levalbuterol L-tartrate.
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 15, 17)
- - 2. Levalbuterol L-tartrate as claimed in claim 1, which is in crystalline form.
  - 3. Levalbuterol L-tartrate as claimed in claim 2, containing from 0.3 to 0.7% ethanol.
  - 4. Levalbuterol L-tartrate as claimed in claim 2, which is in micronized form.
  - 5. Levalbuterol L-tartrate as claimed in claim 4, which is in the form of needle-like particles.
  - 6. A pharmaceutical composition, which comprises levalbuterol L-tartrate as claimed in claim 1, together with a pharmaceutically acceptable carrier.
  - 7. A pharmaceutical composition as claimed in claim 6, which is an aerosol formulation adapted for administration using a metered dose inhaler, the aerosol formulation comprising levalbuterol L-tartrate in crystalline form and a propellant.
  - 8. A pharmaceutical composition as claimed in claim 7, in which the propellant is 1,1,1,2-tetrafluoroethane.
  - 9. A pharmaceutical composition as claimed in claim 7, which further comprises a surfactant.
  - 10. A pharmaceutical composition as claimed in claim 7, which further comprises a co-solvent.
  - 11. A pharmaceutical composition as claimed in claim 10, in which the co-solvent is ethanol.
  - 15. A metered dose inhaler comprising a canister containing an aerosol formulation as defined in claim 7, a metering valve and a valve stem.
  - 17. A pharmaceutical composition as claimed in claim 6, which is adapted for administration using a dry powder inhaler or insufflator.

12. An aerosol formulation adapted for administration using a metered dose inhaler, the aerosol formulation comprising levalbuterol L-tartrate crystals in the form of micronized, needle-like particles, and a propellant.
- View Dependent Claims (13, 14, 16)
- - 13. An aerosol formulation as claimed in claim 12, in which the propellant is 1,1,1,2-tetrafluoroethane.
  - 14. An aerosol formulation as claimed in claim 13, which further comprises from 2 to 6% by weight of ethanol as a co-solvent.
  - 16. A metered dose inhaler comprising a canister containing an aerosol formulation as defined in claim 12, a metering valve and a valve stem.

18. A process for the preparation of levalbuterol L-tartrate crystals, which comprises combining a solution of levalbuterol with a solution of L-tartaric acid and recovering levalbuterol L-tartrate crystals.
- View Dependent Claims (19, 20, 21, 22, 23, 25)
- - 19. A process as claimed in claim 18, in which the solvent in each solution comprises ethanol.
  - 20. A process as claimed in claim 18, in which the crystallization conditions are selected so as to provide crystals having a length of 10 to 50 microns and a width of 0.2 to 4 microns.
  - 21. A process as claimed in claim 18, in which the levalbuterol L-tartrate has been prepared by hydrogenating R-benzylalbuterol in the presence of palladium on carbon.
  - 22. A process as claimed in claim 21, in which the hydrogenation has been conducted under conditions selected to effect conversion of at least 99.9% of the R-benzylalbuterol without over reduction of other functional groups.
  - 23. A process as claimed in claim 18, in which the crystals are dried and micronized, the crystallization and drying conditions being selected so as to afford needle-like particles after micronization.
  - 25. Levalbuterol L-tartrate crystals whenever obtained by the process of claim 18.

24. A process for the preparation of levalbuterol L-tartrate crystals, which comprises combining a solution of levalbuterol with a solution of L-tartaric acid, recovering levalbuterol L-tartrate crystals, and then drying and micronizing the recovered crystals, the crystallization and drying conditions being selected so as to afford needle-like particles after micronization.
- View Dependent Claims (26)
- - 26. Levalbuterol L-tartrate crystals whenever obtained by the process of claim 24.

27. A method of effecting bronchodilation in a patient in need of treatment, which comprises administering to said patient an effective amount of levalbuterol L-tartrate.
- View Dependent Claims (28, 29)
- - 28. A method as claimed in claim 27, in which micronized crystals of levalbuterol L-tartrate are administered by inhalation using a metered dose inhaler.
  - 29. A method as claimed in claim 28, in which the micronized crystals of levalbuterol L-tartrate are in the form of needle-like particles.

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Current Assignee
Lupin Inc. (Lupin Limited)
Original Assignee
Sepracor Incorporated
Inventors
McGlynn, Paul, Sturge, Craig, Bakale, Roger

Granted Patent

US 7,256,310 B2
Time in Patent Office

Days
Field of Search
US Class Current

424/46
CPC Class Codes

A61K 31/205   Amine addition salts of org...

A61K 9/008   comprising drug dissolved o...

A61K 9/14   Particulate form, e.g. powd...

A61M 15/002   with air flow regulating means

A61M 15/009   using medicine packages wit...

A61M 2202/0484   Alcohol

A61M 2202/0488   Surfactant, e.g. for the lung

A61M 2202/064   Powder

A61P 11/00   Drugs for disorders of the ...

A61P 11/06   Antiasthmatics

A61P 11/08   Bronchodilators

C07B 2200/07   Optical isomers

C07B 2200/13   Crystalline forms, e.g. pol...

C07C 215/60   the chain having two carbon...

C07C 59/255   Tartaric acid

C09K 3/30   for aerosols aerosol contai...

Levalbuterol salt

First Claim

5 Assignments

0 Petitions

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Abstract

7 Citations

29 Claims

Specification

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Levalbuterol salt

First Claim

5 Assignments

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Subscription Required

0 Petitions

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Accused Products

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Abstract

7 Citations

29 Claims

Specification

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Solutions

Use Cases

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