IP Library Granted Patent US 11,299,458
Granted Patent B2
US 11,299,458 · App. 16/993,648 · Granted Apr 12, 2022

Crystalline compounds

Inventors: Anthony Alexander McKinney (Newton Center, MA); Franklin Bymaster (Brownsburg, IN); Walter Piskorski (Nashua, NH); Fred J. Fleitz (Germantown, WI); Yonglai Yang (Hockessin, DE); David A. Engers (West Lafayette, IN); Valeriya Smolenskaya (West Lafayette, IN); Venkat Kusukuntla (Germantown, WI)
Assignee: OTSUKA AMERICA PHARMACEUTICAL, INC.
C07D209/52C07C211/17
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Quick Facts
Patent No.
US 11,299,458
App. No.
16/993,648
Granted
Apr 12, 2022
Kind
B2
Abstract

The present invention relates to crystalline forms of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride and compositions comprising the same and methods of making and using the same.

Claims (10)

1. A process for making Crystalline Form B of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride, wherein the process comprises seeding a solution or slurry of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride with Crystalline Form B of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride, wherein the Crystalline Form B exhibits an X-ray powder diffraction (XRPD) pattern comprising d-spacing (Å) values of 14.6, 5.1, 4.7, 4.6, and 3.6.

2. The process of claim 1 , wherein the solution or slurry is seeded while the temperature of the solution or slurry is above room temperature.

3. The process of claim 1 , wherein the Crystalline Form B exhibits an X-ray powder diffraction (XRPD) pattern measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å substantially as shown in any figure selected from FIGS. 40 and 48 .

4. The process of claim 2 , wherein the Crystalline Form B exhibits an X-ray powder diffraction (XRPD) pattern measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å substantially as shown in any figure selected from FIGS. 40 and 48 .

5. The process of claim 1 further comprising isolating the Crystalline Form B.

6. The process of claim 2 further comprising isolating the Crystalline Form B.

7. The process of claim 3 further comprising isolating the Crystalline Form B.

8. The process of claim 4 further comprising isolating the Crystalline Form B.

9. A process for making a pharmaceutical composition comprising Crystalline Form B of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride, wherein the process comprises isolating Crystalline Form B of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride and admixing the isolated Crystalline Form B with a pharmaceutically acceptable diluent or carrier, wherein the Crystalline Form B exhibits an X-ray powder diffraction (XRPD) pattern comprising d-spacing (Å) values of 14.6, 5.1, 4.7, 4.6, and 3.6.

10. The process of claim 9 , wherein the Crystalline Form B exhibits an X-ray powder diffraction (XRPD) pattern measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å substantially as shown in any figure selected from FIGS. 40 and 48 .

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: KUSUKUNTLA, VENKAT
To: NEUROVANCE, INC.
Reel/Frame 053842/0406 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: FLEITZ, FRED J.
To: NEUROVANCE, INC.
Reel/Frame 053842/0496 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: MCKINNEY, ANTHONY ALEXANDER; BYMASTER, FRANKLIN; PISKORSKI, WALTER
To: NEUROVANCE, INC.
Reel/Frame 053839/0775 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: YANG, YONGLAI; SMOLENSKAYA, VALERIYA; ENGERS, DAVID A.
To: AMRI SSCI, LLC
Reel/Frame 053840/0189 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: AMRI SSCI, LLC
To: NEUROVANCE, INC.
Reel/Frame 053841/0739 →
MERGER Recorded Sep 22, 2020
From: NEUROVANCE, INC.
To: OTSUKA AMERICA PHARMACEUTICAL, INC.
Reel/Frame 053843/0664 →
Continuity (6)
Continuation 16298179 · Mar 11, 2019
Continuation 15820241 · Nov 21, 2017
Continuation 15611580 · Jun 1, 2017
Continuation 15186415 · Jun 17, 2016
Provisional Application 62181174 · Jun 17, 2015
Related Publication 20210198198A1 · Jul 1, 2021
Cited By (1)
US 12,502,358