US2017305905A1PendingUtilityA1
Crystalline form of an anxiolytic compound
Est. expiryMar 15, 2033(~6.7 yrs left)· nominal 20-yr term from priority
A61P 9/10A61P 9/00A61P 25/20A61P 25/24A61P 25/18A61P 25/16A61P 25/22A61P 29/00A61P 25/28A61P 25/14A61P 25/04A61P 1/04A61P 25/00A61P 21/02A61P 21/00C07D 471/04C07B 2200/13
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Claims
Abstract
The present invention provides a crystalline Form B of compound 1, and pharmaceutically compositions thereof. The present invention also provides methods of treating a disease (e.g., a disease of the central nervous system) using the pharmaceutical compositions.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A method of preparing a crystalline Form B of compound I of formula:
the method comprising mixing a solution of compound 1 in methanol with an aqueous solution of a base to provide a mixture.
2 . The method of claim 1 , further comprising lowering the temperature of the mixture to provide a solid.
3 . The method of claim 2 , further comprising isolating the solid from the mixture.
4 . The method of claim 1 wherein the base is selected from the group consisting of Na 2 CO 3 and NaHCO 3 .
5 . The method of claim 4 wherein the base is Na 2 CO 3 .
6 . The method of claim 1 wherein Form B is prepared in greater than 99% purity.
7 . The method of claim 1 wherein the crystalline Form B is a hydrate.
8 . The method of claim 1 wherein the crystalline Form B is a hemihydrate.
9 . The method of claim 1 wherein the crystalline Form B is a non-stoichiometric hydrate.
10 . The method of claim 1 wherein the crystalline Form B is substantially free of amorphous compound 1.
11 . The method of claim 1 wherein the crystalline Form B is characterized by having four or more peaks in its XRPD pattern selected from those in the following table:
Angle
2-Theta °
13.94
14.52
16.27
16.60
17.62
18.76
19.02
19.29
19.64
22.32
22.77
23.02
23.16.
12 . The method of claim 1 wherein the crystalline Form B is characterized by a Raman spectrum with characteristic peaks selected from those in the following table:
Wavenumber
(cm −1 )
3322
3070
3007
2993
2963
2931
2910
2871
2842
1636
1611
1604
1508
1497
1478
1459
1446
1425
1393
1355
1344
1319
1304
1285
1271
1243
1225
1208
1150
1136
1112
1095
1064
1039
1025
1010
996
957
943
849
819
810
789
741
713
681
603
585
555
501
484
446
419
372
349
316
261
234
185
141.
13 . The method of claim 1 wherein the crystalline Form B is characterized by a DSC thermogram with an endotherm having a peak temperature (T max ) of about 176° C.
14 . The method of claim 1 wherein the crystalline Form B is characterized by a DSC thermogram with a ΔH of about 105 J/g.
15 . The method of claim 1 wherein the crystalline Form B is characterized by a glass transition (T g ) of about 71° C. after quench cooling.
16 . The method of claim 1 wherein the crystalline Form B is characterized by a ΔC p of about 0.48 J/(g° C.) after quench cooling.Cited by (0)
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