US2020317621A1PendingUtilityA1
Polymorphic forms of 3-[2-butyl-1-(2-diethylamino-ethyl)-1h-benzoimidazol-5-yl]-n-hydroxy-acrylamide and uses thereof
Est. expiryMay 2, 2036(~9.8 yrs left)· nominal 20-yr term from priority
Inventors:David F. Duncan
C07B 2200/13A61K 31/4184C07D 235/14C07D 235/08A61P 35/02
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exact text as granted — not AI-modified1 - 24 . (canceled)
25 . A process for the preparation of a crystalline polymorph of 3-[2-butyl-1-(2-diethylamino-ethyl)-1H-benzoimidazol-5-yl]-N-hydroxy-acrylamide dihydrochloride, the process comprising crystallizing 3-[2-butyl-1-(2-diethylamino-ethyl)-1H-benzoimidazol-5-yl]-N-hydroxy-acrylamide dihydrochloride from a mixture of acetonitrile and water.
26 . The process of claim 25 , wherein the process further comprises isolating the crystalline polymorph by filtration, without drying.
27 . The process of claim 25 , wherein the crystalline polymorph is characterized by X-ray powder diffraction peaks at least at 6.46, 20.26, and 26.68°2θ±0.1°2θ.
28 . The process of claim 27 , wherein the crystalline polymorph is further characterized by an X-ray powder diffraction peaks at 22.27°2θ±0.1°2θ.
29 . The process of claim 28 , wherein the crystalline polymorph is further characterized by at least two X-ray powder diffraction peaks at 9.78, 16.57, or 19.58°2θ±0.1°2θ.
30 . The process of claim 25 , wherein the crystalline polymorph presents itself as columnar particles.
31 . The process of claim 25 , wherein the crystalline polymorph comprises less than 5% by weight of the monohydrate polymorph.
32 . The process of claim 25 , wherein the crystalline polymorph comprises less than 3% by weight of the monohydrate polymorph.
33 . The process of claim 25 , wherein the crystalline polymorph comprises less than 1% by weight of the monohydrate polymorph.
34 . The process of claim 25 , wherein the crystalline polymorph comprises less than 0.5% by weight of the monohydrate polymorph.
35 . The process of claim 25 , wherein the crystalline polymorph comprises less than 5% by weight of amorphous 3-[2-butyl-1-(2-diethylamino-ethyl)-1H-benzoimidazol-5-yl]-N-hydroxy-acrylamide dihydrochloride.
36 . The process of claim 25 , wherein the crystalline polymorph comprises less than 3% by weight of amorphous 3-[2-butyl-1-(2-diethylamino-ethyl)-1H-benzoimidazol-5-yl]-N-hydroxy-acrylamide dihydrochloride.
37 . The process of claim 25 , wherein the crystalline polymorph comprises less than 1% by weight of amorphous 3-[2-butyl-1-(2-diethylamino-ethyl)-1H-benzoimidazol-5-yl]-N-hydroxy-acrylamide dihydrochloride.
38 . The process of claim 25 , wherein the crystalline polymorph comprises less than 0.5% by weight of amorphous 3-[2-butyl-1-(2-diethylamino-ethyl)-1H-benzoimidazol-5-yl]-N-hydroxy-acrylamide dihydrochloride.
39 . The process of claim 25 , wherein the process comprises:
suspending 3-[2-butyl-1-(2-diethylamino-ethyl)-1H-benzoimidazol-5-yl]-N-hydroxy-acrylamide dihydrochloride in acetonitrile; heating the suspension to reflux; adding water until the mixture is homogenous; and precipitating the crystalline polymorph from the solution by cooling and/or reducing the volume of the solution.
40 . A process for the preparation of a crystalline polymorph of 3-[2-butyl-1-(2-diethylamino-ethyl)-1H-benzoimidazol-5-yl]-N-hydroxy-acrylamide dihydrochloride, the process comprising crystallizing 3-[2-butyl-1-(2-diethylamino-ethyl)-1H-benzoimidazol-5-yl]-N-hydroxy-acrylamide dihydrochloride from a mixture of ethanol and water.
41 . The process of claim 40 , wherein the crystalline polymorph is characterized by X-ray powder diffraction peaks at least at 6.46, 20.26, and 26.68°2θ±0.1°2θ.
42 . The process of claim 41 , wherein the crystalline polymorph is further characterized by an X-ray powder diffraction peaks at 22.27°2θ±0.1°2θ.
43 . The process of claim 42 , wherein the crystalline polymorph is further characterized by at least two X-ray powder diffraction peaks at 9.78, 16.57, or 19.58°2θ±0.1°2θ.Join the waitlist — get patent alerts
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