Fatty acid amide hydrolase inhibitors

• US 9,034,849 B2
• Filed: 02/01/2011
• Issued: 05/19/2015
• Est. Priority Date: 02/03/2010
• Status: Active Grant

• Current Assignee: Infinity Pharmaceuticals, Inc.
• Original Assignee: Infinity Pharmaceuticals, Inc.
• Inventors: Austad, Brian C., Grenier, Louis, Grogan, Michael J., Liu, Tao, Lo, Ching Kam, Martinot, Theodore A., Yu, Lin-Chen
• Primary Examiner(s): Ricci, Craig
• Assistant Examiner(s): BARSKY, JARED
• Application Number:
  US13/019,262
• Publication Number:
  US 20110201574A1
• Time in Patent Office: 1,568 Days
• Field of Search: None
• US Class Current: 514/64
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 1/02 Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 1/08 for nausea, cinetosis or vertigo; Antiemetics
• CPC Class Codes: A61P 13/10 of the bladder
• CPC Class Codes: A61P 15/00 Drugs for genital or sexual disorders for disorders of sex hormones A61P5/24; Contraceptives
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 17/04 Antipruritics
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 21/00 Drugs for disorders of the muscular or neuromuscular system
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/08 Antiepileptics; Anticonvulsants
• CPC Class Codes: A61P 25/20 Hypnotics; Sedatives
• CPC Class Codes: A61P 25/28 for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: A61P 25/36 Opioid-abuse
• CPC Class Codes: A61P 27/06 Antiglaucoma agents or miotics
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 3/00 Drugs for disorders of the metabolism of the blood or the extracellular fluid A61P7/00
• CPC Class Codes: A61P 3/04 Anorexiants; Antiobesity agents
• CPC Class Codes: A61P 37/00 : Drugs for immunological or allergic disorders
• CPC Class Codes: A61P 37/02 : Immunomodulators
• CPC Class Codes: A61P 43/00 : Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 9/00 : Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/10 : for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: A61P 9/12 : Antihypertensives
• CPC Class Codes: C07B 2200/13 : Crystalline forms, e.g. polymorphs
• CPC Class Codes: C07F 5/025 : Boronic and borinic acid compounds
• CPC Class Codes: C07F 5/05 : Cyclic compounds having at least one ring containing boron but no carbon in the ring

Abstract

The present invention provides fatty acid amide hydrolase inhibitors, solid forms thereof, compositions thereof, and methods of making and using the same.

Claims

1. A solid form comprising a crystalline compound of formula 1:

2. The solid form of claim 1, wherein the solid form is substantially free of a compound of formula IMP-1, formula IMP-2, formula IMP-3, or formula IMP-4:

3. The solid form of claim 2, wherein the solid form is substantially free of an amorphous compound of formula 1.

4. The solid form of claim 2, wherein the solid form is substantially free of the compound of formula IMP-1.

5. The solid form of claim 4, wherein the solid form has less than about 0.05% a/a of the compound of formula IMP-1.

6. The solid form of claim 2, wherein the solid form is substantially free of the compound of formula IMP-2.

7. The solid form of claim 6, wherein the solid form has less than about 0.05% a/a of the compound of formula IMP-2.

8. The solid form of claim 2, wherein the solid form is substantially free of the compound of formula IMP-3.

9. The solid form of claim 8, wherein the solid form has less than about 0.05% a/a of the compound of formula IMP-3.

10. The solid form of claim 2, wherein the solid form is substantially free of the compound of formula IMP-4.

11. The solid form of claim 10, wherein the solid form has less than about 0.05% a/a of the compound of formula IMP-4.

12. The solid form of claim 1, wherein the solid form is substantially free of other crystal forms of formula 1.

13. The solid form of claim 1 having an X-ray powder diffraction pattern further comprising peaks at approximate peak positions of 24.68±

0.10 and 25.48±

0.10 degrees 2θ

.

14. The solid form of claim 13 having an X-ray powder diffraction pattern further comprising peaks at approximate peak positions of 9.68±

0.10 and 29.08±

0.10 degrees 2θ

.

15. The solid form of claim 14 having an X-ray powder diffraction pattern further comprising peaks at approximate peak positions of 4.83±

0.10, 16.12±

0.10, 16.92±

0.10, 17.75±

0.10, 18.58±

0.10, 18.89±

0.10, 19.34±

0.10, 19.69±

0.10, 21.01±

0.10, 22.46±

0.10, 23.67±

0.10, 24.33±

0.10, 25.16±

0.10, 25.96±

0.10, 26.48±

0.10, 29.43±

0.10, and 29.84±

0.10.

16. The solid form of claim 1, which has unit cell parameters consistent with the following approximate unit cell parameters:

a=5.45 Å

;

b=5.16 Å

;

c=36.12 Å

;

α

=90°

;

β

=90°

;

γ

=90°

;

V=1016.5 Å

³, and Z=4.

17. The solid form of claim 1, wherein the solid form is substantially free of one or more anhydrides of the compounds of formula 1.

18. The solid form of claim 17, wherein the one or more anhydrides is Compound 2:

27. A pharmaceutical composition comprising the solid form of claim 1 and a pharmaceutically acceptable excipient.

28. A pharmaceutical composition comprising the solid form of claim 2 and a pharmaceutically acceptable excipient.

19. A solid form comprising a crystalline compound of formula 2:

20. The solid form according to claim 19, wherein the solid form is substantially free of a compound of formula IMP-1, formula IMP-2, formula IMP-3, or formula IMP-4:

21. The solid form of claim 20, wherein the solid form is substantially free of an amorphous compound of formula 2.

22. The solid form of claim 19, wherein the solid form is substantially free of other crystalline forms of the compound of formula 2.

23. The solid form of claim 19, wherein the solid form is substantially free of a crystalline compound of formula 1:

24. The solid form of claim 19 having an X-ray powder diffraction pattern further comprising a peak at approximately 17.69±

0.10 degrees 2θ

.

25. The solid form of claim 19 having an X-ray powder diffraction pattern further comprising peaks at approximate peak positions of 9.64±

0.10, 11.20±

0.10, 13.14±

0.10, 14.67±

0.10, 15.19±

0.10, 16.85±

0.10, 17.27±

0.10, 17.44±

0.10, 17.69±

0.10, 17.96±

0.10, 18.55±

0.10, 19.04±

0.10, 21.57±

0.10, 22.47±

0.10, 22.68±

0.10, 23.37±

0.10, 24.45±

0.10, 24.66±

0.10, 25.14±

0.10, 25.49±

0.10, and 27.71±

0.10 degrees 2θ

.

26. The solid form of claim 19 having an X-ray powder diffraction pattern further comprising peaks at approximate peak positions of 9.64±

0.10, 11.20±

0.10, 11.51±

0.10, 13.14±

0.10, 14.67±

0.10, 15.19±

0.10, 16.85±

0.10, 17.27±

0.10, 17.44±

0.10, 17.69±

0.10, 17.96±

0.01, 18.55±

0.10, 19.04±

0.10, 19.42±

0.10, 20.36±

0.10, 20.84±

0.10, 21.57±

0.10, 22.47±

0.10, 22.68±

0.10, 22.99±

0.10, 23.37±

0.10, 24.45±

0.10, 24.66±

0.10, 25.14±

0.10, 25.49±

0.10, 27.71±

0.10, 28.26±

0.10, and 29.03±

0.10 degrees 2θ

.

29. A pharmaceutical composition comprising the solid form of claim 19 and a pharmaceutically acceptable excipient.