Crystalline forms of 3-biphenyl-4-yl-(2S)-[(4'-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid, and methods of use
OwnerEric Benjamin, Devi Gohimukkulainventors
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Abstract
The present invention relates to crystalline Forms of 3-biphenyl-4-yl-(2S)-[(4′-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid. In one embodiment, the present invention provides polymorphic Forms I, II, and III of 3-biphenyl-4-yl-(2S)-[(4′trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid.
Claims42
A polymorph of 3-biphenyl-4-yl-(2S)-[(4′-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid, Form I, having the following characteristics:
- (a) X-ray powder diffractions peaks expressed in degrees-2θ at about 18.0, and 19.6;
- and
- (b) a differential scanning calorimetry thermogram comprising at least an exothermic peak at about 236° C. and an endothermic peak at about 294° C.
A polymorph of 3-biphenyl-4-yl-(2S)-[(4′-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid, Form I, having the following characteristics:
- (a) having at least three X-ray powder diffraction peaks expressed in degrees-2θ selected from the group consisting of:
- 18.0, 19.6, 20.1, 21.1;
- and
- (b) having solid state 13C NMR spectrum comprising at least two peaks selected from 173.7, 170.7, 58.0 and 35.6 ppm.
A polymorph of 3-biphenyl-4-yl-(2S)-[(4′-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid, Form II, having the following characteristics:
- (a) an X-ray powder diffraction peak expressed in degrees-2θ at about 16.7;
- and
- (b) a differential scanning calorimetry thermogram comprising at least an exothermic peak at about 243° C. and an endothermic peak at about 294° C.
A polymorph of 3-biphenyl-4-yl-(2S)-[(4′-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid, Form II, having the following characteristics:
- (a) having at least three X-ray powder diffraction peaks expressed in degrees-2θ selected from the group consisting of:
- 16.7, 20.0, 21.5, and 26.8;
- and
- (b) having solid state 13C NMR spectrum comprising at least two peaks selected from 180.0, 168.2, 55.6, and 38.4 ppm.
A method for producing a polymorph of 3-biphenyl-4-yl-(2S)-[(4′-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid comprising:
- dissolving 3-biphenyl-4-yl-(2S)-[(4′-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid in a solvent system comprising a solvent selected from the group consisting of:
- an alcoholic solvent, acetone, ethyl acetate, THF, HPCD, DMA, water, and mixtures thereof, and recovering the precipitate from the solvent system.
A polymorph of 3-biphenyl-4-yl-(2S)-[(4′-trifluoromethyl-biphenyl-4-carbonyl)-amino]-propionic acid, Form III, having the following characteristics:
- (a) having at least two X-ray powder diffractions peaks expressed in degrees-2θ selected from 15.7, 22.3, and 22.7;
- and
- (b) a differential scanning calorimetry thermogram comprising an endothermic peak at about 294° C.
Dependencies are inferred from the claim text.