US2023219887A1PendingUtilityA1

Solid forms comprising an oxime ether compound, compositions and methods of use thereof

Assignee: NOVARTIS AGPriority: Mar 9, 2017Filed: Mar 17, 2023Published: Jul 13, 2023
Est. expiryMar 9, 2037(~10.6 yrs left)· nominal 20-yr term from priority
C07D 205/04A61K 9/2054A61K 31/397C07B 2200/13A61K 9/20A61K 9/48
70
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Claims

Abstract

Provided herein are formulations, processes, solid forms and methods of use relating to (E)-1-(4-(1-(((4-cyclohexyl-3-(trifluoromethyl)benzyl)oxy)imino)ethyl)-2-ethylbenzyl)azetidine-3-carboxylic acid.

Claims

exact text as granted — not AI-modified
1 - 124 . (canceled) 
     
     
         125 . A solid form of (E)-1-(4-(1-(((4-cyclohexyl-3-(trifluoromethyl)benzyl)oxy)imino)ethyl)-2-ethylbenzyl)azetidine-3-carboxylic acid selected from the group consisting of Form D, Form E, Form J, Form K, Form L, Form M, Form N, and mixtures of any of the foregoing. 
     
     
         126 . The solid form of  claim 125 , wherein the solid form is Form D and has an X-ray powder diffraction pattern comprising three or more peaks at 2.8, 3.7, 7.3, 11.0, 14.4, 16.4, 18.3, 20.8, or 22.9° 2θ (±0.2° 2θ). 
     
     
         127 . The solid form of  claim 126 , wherein the solid form is Form D and has an X-ray powder diffraction pattern comprising three or more peaks at 3.7, 7.3, 11.0, 18.3, or 22.9° 2θ (±0.2° 2θ). 
     
     
         128 . The solid form of  claim 125 , wherein the solid form is Form E and has an X-ray powder diffraction pattern comprising three or more peaks at 3.9, 7.7, 9.9, 11.6, 12.1, 14.3, 15.5, 17.3, 18.2, 19.3, 20.9, 21.7, 23.3, 24.5, 25.3, or 32.0° 2θ (±0.2° 2θ). 
     
     
         129 . The solid form of  claim 128 , wherein the solid form is Form E and has an X-ray powder diffraction pattern comprising three or more peaks at 3.9, 7.7, 11.6, 14.3, 20.9, or 24.5° 2θ (±0.2° 2θ). 
     
     
         130 . The solid form of  claim 125 , wherein the solid form is Form J and has an X-ray powder diffraction pattern comprising three or more peaks at 7.9, 11.5, 11.9, 13.4, 13.8, 14.0, 15.7, 17.4, 18.9, 19.6, 20.0, 21.0, 21.4, or 23.5° 2θ (±0.2° 2θ). 
     
     
         131 . The solid form of  claim 130 , wherein the solid form is Form J and has an X-ray powder diffraction pattern comprising three or more peaks at 7.9, 11.9, 13.4, 15.7, 17.4, or 20.0° 2θ (±0.2° 2θ). 
     
     
         132 . The solid form of  claim 125 , wherein the solid form is Form K and has an X-ray powder diffraction pattern comprising three or more peaks at 7.3, 8.0, 10.0, 10.9, 11.5, 12.0, 13.4, 14.1, 15.7, 17.5, 19.0, 20.1, 21.3, or 23.5° 2θ (±0.2° 2θ). 
     
     
         133 . The solid form of  claim 132 , wherein the solid form is Form K and has an X-ray powder diffraction pattern comprising three or more peaks at 7.3, 8.0, 10.0, 10.9, 12.0, 17.5, or 20.1° 2θ (±0.2° 2θ). 
     
     
         134 . The solid form of  claim 125 , wherein the solid form is Form L and has an X-ray powder diffraction pattern comprising three or more peaks at 11.5, 12.0, 13.4, 15.7, 17.5, 19.0, 19.6, 20.1, 21.0, 21.3, or 23.5° 2θ (±0.2° 2θ). 
     
     
         135 . The solid form of  claim 134 , wherein the solid form is Form L and has an X-ray powder diffraction pattern comprising three or more peaks at 11.5, 12.0, 13.4, 17.5, 20.1, or 21.3° 2θ (±0.2° 2θ). 
     
     
         136 . The solid form of  claim 125 , wherein the solid form is Form M and has an X-ray powder diffraction pattern comprising three or more peaks at 7.2, 8.0, 9.5, 10.9, 11.5, 12.0, 13.4, 15.7, 16.4, 17.5, 18.2, 19.0, 19.5, 20.1, 20.7, 21.3, 22.8, or 23.4° 2θ (±0.2° 2θ). 
     
     
         137 . The solid form of  claim 136 , wherein the solid form is Form M and has an X-ray powder diffraction pattern comprising three or more peaks at 7.2, 9.5, 12.0, 16.4, 18.2, or 22.8° 2θ (±0.2° 2θ). 
     
     
         138 . The solid form of  claim 125 , wherein the solid form is Form N and has an X-ray powder diffraction pattern comprising three or more peaks 11.6, 12.0, 13.5, 13.8, 14.0, 14.6, 15.8, 16.2, 17.7, 19.2, 19.6, 20.1, 21.6, 21.7, 23.2, 23.7, or 24.1° 2θ (±0.2° 2θ). 
     
     
         139 . The solid form of  claim 138 , wherein the solid form is Form N and has an X-ray powder diffraction pattern comprising three or more peaks 12.0, 13.5, 17.7, 20.1, 21.6, or 23.7° 2θ (±0.2° 2θ). 
     
     
         140 . A pharmaceutical composition comprising the solid form of  claim 125  and pharmaceutically acceptable carrier or excipient. 
     
     
         141 . The pharmaceutical composition of  claims 140 , which is a single unit dosage form. 
     
     
         142 . The pharmaceutical composition of  claim 140 , which is selected from a tablet and a capsule. 
     
     
         143 . A method of treating multiple sclerosis, wherein the method comprises administering to a patient in need thereof a therapeutically effective amount of a solid form of  claim 125 . 
     
     
         144 . A method of treating multiple sclerosis, wherein the method comprises administering to a patient in need thereof a therapeutically effective amount of a pharmaceutical composition according to  claim 140 .

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