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Last Updated: March 28, 2024

Claims for Patent: 9,963,459


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Summary for Patent: 9,963,459
Title:Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-alpla]pyrrolo[2,3-e]-pyrazin-8-YL)-N-(2- ,2,2-Trifluoroethyl)pyrrol and solid state forms thereof
Abstract: The present disclosure relates to processes for preparing (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide, solid state forms thereof, and corresponding pharmaceutical compositions, methods of treatment (including treatment of rheumatoid arthritis), kits, methods of synthesis, and products-by-process.
Inventor(s): Jayanth; Jayanthy (Buffalo, IL), Marroum; Patrick J. (Springfield, VA), Mayer; Peter T. (Libertyville, IL), Mohamed; Mohamed-Eslam F. (Gurnee, IL), Othman; Ahmed A. (Waukegan, IL)
Assignee: AbbVie Inc. (North Chicago, IL)
Application Number:15/857,892
Patent Litigation and PTAB cases: See patent lawsuits and PTAB cases for patent 9,963,459
Patent Claims: 1. An extended release solid dosage form comprising a) (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide or a pharmaceutically acceptable salt thereof, in an amount sufficient to deliver about 15 mg of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide freebase equivalent; b) an acidic pH modifier; and c) a release control polymer.

2. The extended release solid dosage form of claim 1, wherein the release control polymer is a hydrophilic polymer and wherein the acidic pH modifier is an organic acid.

3. The extended release solid dosage form of claim 2, wherein the organic acid is present in an amount from about 10 w/w % to about 35 w/w %.

4. The extended release solid dosage form of claim 3, wherein the organic acid is tartaric acid.

5. The extended release solid dosage form of claim 2, wherein the extended release formulation provides for the release of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide or a pharmaceutically acceptable salt thereof upon entry into a use environment at a rate substantially independent of the pH of the use environment, wherein the use environment has a pH range from about 1.2 to about 6.8.

6. The extended release solid dosage form of claim 5, wherein the organic acid is present in an amount from about 10 w/w % to about 35 w/w %.

7. The extended release solid dosage form of claim 6, wherein the organic acid is tartaric acid.

8. The extended release solid dosage form of claim 2, wherein the extended release solid dosage form, when added to a test medium comprising 900 mL of 50 mM pH 6.8 sodium phosphate buffer at 37.degree. C..+-.0.5.degree. C. in a standard USP rotating paddle apparatus when the paddles are rotated at 75 rpm.+-.4%, dissolves from about 50% to about 90% of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-- (2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide or a pharmaceutically acceptable salt thereof after about 8 hours.

9. The extended release solid dosage form of claim 8, wherein the organic acid is present in an amount from about 10 w/w % to about 35 w/w %.

10. The extended release solid dosage form of claim 9, wherein the organic acid is tartaric acid.

11. An extended release solid dosage form comprising a) (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide in an amount sufficient to deliver about 15 mg of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide freebase equivalent; b) an acidic pH modifier; and c) a release control polymer.

12. The extended release solid dosage form of claim 11, wherein the release control polymer is a hydrophilic polymer and wherein the acidic pH modifier is an organic acid.

13. The extended release solid dosage form of claim 12, wherein the organic acid is present in an amount from about 10 w/w % to about 35 w/w %.

14. The extended release solid dosage form of claim 13, wherein the organic acid is tartaric acid.

15. The extended release solid dosage form of claim 12, wherein the extended release formulation provides for the release of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide upon entry into a use environment at a rate substantially independent of the pH of the use environment, wherein the use environment has a pH range from about 1.2 to about 6.8.

16. The extended release solid dosage form of claim 15, wherein the organic acid is present in an amount from about 10 w/w % to about 35 w/w %.

17. The extended release solid dosage form of claim 16, wherein the organic acid is tartaric acid.

18. The extended release solid dosage form of claim 12, wherein the extended release solid dosage form, when added to a test medium comprising 900 mL of 50 mM pH 6.8 sodium phosphate buffer at 37.degree. C..+-.0.5.degree. C. in a standard USP rotating paddle apparatus when the paddles are rotated at 75 rpm.+-.4%, dissolves from about 50% to about 90% of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-- (2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide after about 8 hours.

19. The extended release solid dosage form of claim 18, wherein the organic acid is present in an amount from about 10 w/w % to about 35 w/w %.

20. The extended release solid dosage form of claim 19, wherein the organic acid is tartaric acid.

21. An extended release solid dosage form comprising a) a crystalline hemihydrate of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide) is present in an amount sufficient to deliver about 15 mg of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide freebase equivalent; b) an acid pH modifier; and c) a release control polymer; wherein the crystalline hemihydrate of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide has an X-ray powder diffraction pattern characterized by peaks at 13.4.+-.0.2, 15.1.+-.0.2, and 21.7.+-.0.2 degrees two theta when measured at about 25.degree. C. with monochromatic K.alpha.1 radiation.

22. The extended release solid dosage form of claim 21, wherein the release control polymer is a hydrophilic polymer and wherein the acidic pH modifier is an organic acid.

23. The extended release solid dosage form of claim 22, wherein the organic acid is present in an amount from about 10 w/w % to about 35 w/w %.

24. The extended release solid dosage form of claim 23, wherein the organic acid is tartaric acid.

25. The extended release solid dosage form of claim 22, wherein the extended release formulation provides for the release of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide upon entry into a use environment at a rate substantially independent of the pH of the use environment, wherein the use environment has a pH range from about 1.2 to about 6.8.

26. The extended release solid dosage form of claim 25, wherein the organic acid is present in an amount from about 10 w/w % to about 35 w/w %.

27. The extended release solid dosage form of claim 26, wherein the organic acid is tartaric acid.

28. The extended release solid dosage form of claim 22, wherein the extended release solid dosage form, when added to a test medium comprising 900 mL of 50 mM pH 6.8 sodium phosphate buffer at 37.degree. C..+-.0.5.degree. C. in a standard USP rotating paddle apparatus when the paddles are rotated at 75 rpm.+-.4%, dissolves from about 50% to about 90% of the crystalline hemihydrate of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-- trifluoroethyl)pyrrolidine-1-carboxamide after about 8 hours.

29. The extended release solid dosage form of claim 28, wherein the organic acid is present in an amount from about 10 w/w % to about 35 w/w %.

30. The extended release solid dosage form of claim 29, wherein the organic acid is tartaric acid.

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