IP Library Granted Patent US 9,108,961
Granted Patent B2
US 9,108,961 · App. 14/184,453 · Granted Aug 18, 2015

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

Inventors: Patricia Oliver-Shaffer (Acton, MA); Gideon Shapiro (Gainesville, FL); Richard Chesworth (Concord, MA); Muneki Kishida (Osaka, JP); Takayuki Ishige (Osaka, JP)
Assignee: Forum Pharmaceuticals, Inc.
C07D453/02
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Quick Facts
Patent No.
US 9,108,961
App. No.
14/184,453
Granted
Aug 18, 2015
Kind
B2
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 (20)

1. A method of improving cognition in a patient suffering from Schizophrenia, comprising administering to the patient a crystalline Form I of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate.

2. The method of claim 1 , wherein the crystalline Form I of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate is characterized by an x-ray powder diffraction pattern 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.

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

4. The method of claim 2 , wherein the crystalline Form I is characterized by an x-ray powder diffraction pattern with at least eight peaks selected from the group of peaks.

5. The method of claim 2 , wherein the crystalline Form I is characterized by an x-ray powder diffraction pattern with all of the peaks selected from the group of peaks.

6. The method of claim 1 , wherein the method further treats cognitive loss in the patient.

7. The method of claim 6 , wherein the patient is over age 60.

8. The method of claim 6 , wherein the patient further suffers from age-related memory loss.

9. A method of improving cognition in a patient suffering from Alzheimer's Disease, comprising administering to the patient a pharmaceutical composition comprising a crystalline Form I of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate.

10. The method of claim 9 , wherein the crystalline Form I of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate is characterized by an x-ray powder diffraction pattern 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.

11. The method of claim 10 , wherein the crystalline Form I is characterized by an x-ray powder diffraction pattern with at least six peaks selected from the group of peaks.

12. The method of claim 10 , wherein the crystalline Form I is characterized by an x-ray powder diffraction pattern with at least eight peaks selected from the group of peaks.

13. The method of claim 10 , wherein the crystalline Form I is characterized by an x-ray powder diffraction pattern with all of the peaks selected from the group of peaks.

14. The method of claim 9 , wherein the method further treats cognitive loss in the patient.

15. The method of claim 14 , wherein the patient is over age 60.

16. The method of claim 14 , wherein the patient further suffers from age-related memory loss.

Assignments (5)
SECURITY INTEREST Recorded Jul 5, 2016
From: FORUM PHARMACEUTICALS INC.
To: FMR LLC
Reel/Frame 039254/0828 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2014
From: KISHIDA, MUNEKI; ISHIGE, TAKAYUKI
To: MITSUBISHI TANABE PHARMA CORPORATION
Reel/Frame 032933/0213 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2014
From: OLIVER-SHAFFER, PATRICIA; SHAPIRO, GIDEON; CHESWORTH, RICHARD
To: ENVIVO PHARMACEUTICALS, INC.
Reel/Frame 032933/0319 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 20, 2014
From: MITSUBISHI TANABE PHARMA CORPORATION
To: ENVIVO PHARMACEUTICALS, INC.
Reel/Frame 032933/0485 →
CHANGE OF NAME Recorded Apr 21, 2014
From: ENVIVO PHARMACEUTICALS, INC.
To: FORUM PHARMACEUTICALS, INC.
Reel/Frame 032722/0659 →
Continuity (4)
Continuation 13698759
Provisional Application 61345363 · May 17, 2010
Provisional Application 61352092 · Jun 7, 2010
Related Publication 20140249179A1 · Sep 4, 2014