Crystalline form of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate

• US 8,710,227 B2
• Filed: 05/17/2011
• Issued: 04/29/2014
• Est. Priority Date: 05/17/2010
• Status: Expired due to Fees

• Current Assignee: Forum Pharmaceuticals Inc.
• Original Assignee: Envivo Pharmaceuticals, Inc.
• Inventors: Oliver-Shaffer, Patricia, Shapiro, Gideon, Chesworth, Richard, Kishida, Muneki, Ishige, Takayuki
• Primary Examiner(s): REESE, HEIDI L
• Application Number:
  US13/698,759
• Publication Number:
  US 20130183380A1
• Time in Patent Office: 1,078 Days
• Field of Search: None
• US Class Current: 546/133
• CPC Class Codes: A61K 31/439 the ring forming part of a bridged ring system, e.g. quinuclidine 8-azabicyclo [3.2.1] octanes A61K31/46
• CPC Class Codes: A61K 9/4833 Encapsulating processes; Filling of capsules mechanical aspects A61J3/07
• CPC Class Codes: A61K 9/4841 Filling excipients; Inactive ingredients
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/14 for treating abnormal movements, e.g. chorea, dyskinesia
• CPC Class Codes: A61P 25/16 Anti-Parkinson drugs
• CPC Class Codes: A61P 25/18 Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
• 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 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07B 2200/13 Crystalline forms, e.g. polymorphs
• CPC Class Codes: C07D 453/02 containing not further condensed quinuclidine ring systems
• CPC Class Codes: C30B 29/54 Organic compounds
• CPC Class Codes: C30B 7/08 by cooling of the solution

Abstract

Crystalline Forms I and II of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate and compositions, methods of manufacture and therapeutic uses thereof are described.

Claims

1. A crystalline Form I of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate, characterized by an x-ray powder diffraction pattern having having peaks expressed as 2Θ

at;

i) one or both of 17.48 and 20.58 ±

0.20 degrees when measured against an internal silicon standard; and

ii) at least four peaks selected from a group of peaks consisting of;

4.50, 9.04, 14.60, 15.14, 15.80, 16.60, 18.16, 18.44, 19.48, 21.74 and 25.46±

0.20 degrees when measured against an internal silicon standard.

2. The crystalline Form I of claim 1, characterized by an x-ray powder diffraction pattern, wherein at least six peaks are selected from the group of peaks.

3. The crystalline Form I of claim 1, characterized by an x-ray powder diffraction pattern, wherein at least eight peaks are selected from the group of peaks.

4. The crystalline Form I of claim 1, characterized by an x-ray powder diffraction pattern, wherein all of the peaks are selected from the group of peaks.

10. A pharmaceutical composition comprising the crystalline Form I of claim 2.

11. The pharmaceutical composition of claim 10, wherein the pharmaceutical composition is for the treatment of cognitive loss in a subject suffering from Alzheimer'"'"'s disease.

12. The pharmaceutical composition of claim 10, wherein the pharmaceutical composition is for the treatment of cognitive loss in a subject suffering from Schizophrenia.

13. The pharmaceutical composition of claim 10, wherein the pharmaceutical composition is for the improvement of cognition in a subject suffering from Alzheimer'"'"'s disease.

14. The pharmaceutical composition of claim 10, wherein the pharmaceutical composition is for the improvement of cognition in a subject suffering from Schizophrenia.

15. A pharmaceutical composition comprising the crystalline Form I of claim 3.

16. The pharmaceutical composition of claim 15, wherein the pharmaceutical composition is for the treatment of cognitive loss in a subject suffering from Alzheimer'"'"'s disease.

17. The pharmaceutical composition of claim 15, wherein the pharmaceutical composition is for the treatment of cognitive loss in a subject suffering from Schizophrenia.

18. The pharmaceutical composition of claim 15, wherein the pharmaceutical composition is for the improvement of cognition in a subject suffering from Alzheimer'"'"'s disease.

19. The pharmaceutical composition of claim 15, wherein the pharmaceutical composition is for the improvement of cognition in a subject suffering from Schizophrenia.

20. A pharmaceutical composition comprising the crystalline Form I of claim 4.

21. The pharmaceutical composition of claim 20, wherein the pharmaceutical composition is for the treatment of cognitive loss in a subject suffering from Alzheimer'"'"'s disease.

22. The pharmaceutical composition of claim 20, wherein the pharmaceutical composition is for the treatment of cognitive loss in a subject suffering from Schizophrenia.

23. The pharmaceutical composition of claim 20, wherein the pharmaceutical composition is for the improvement of cognition in a subject suffering from Alzheimer'"'"'s disease.

24. The pharmaceutical composition of claim 20, wherein the pharmaceutical composition is for the improvement of cognition in a subject suffering from Schizophrenia.

5. A pharmaceutical composition comprising the crystalline Form I.

6. The pharmaceutical composition of claim 5, wherein the pharmaceutical composition is for the treatment of cognitive loss in a subject suffering from Alzheimer'"'"'s disease.

7. The pharmaceutical composition of claim 5, wherein the pharmaceutical composition is for the treatment of cognitive loss in a subject suffering from Schizophrenia.

8. The pharmaceutical composition of claim 5, wherein the pharmaceutical composition is for the improvement of cognition in a subject suffering from Alzheimer'"'"'s disease.

9. The pharmaceutical composition of claim 5, wherein the pharmaceutical composition is for the improvement of cognition in a subject suffering from Schizophrenia.