US2019177258A1PendingUtilityA1

New solid forms of cannabidiol and uses thereof

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Assignee: ARTELO BIOSCIENCES INCPriority: Dec 11, 2017Filed: Dec 10, 2018Published: Jun 13, 2019
Est. expiryDec 11, 2037(~11.4 yrs left)· nominal 20-yr term from priority
C07C 2601/16C07C 39/23C07B 2200/13C07D 241/12C07D 207/16A61K 31/658A61K 47/183A61K 9/14A61K 47/545A61K 31/05
67
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Claims

Abstract

Disclosed herein are cocrystals of cannabidiol and a coformer containing 5-6 membered rings comprised of carbon and nitrogen atoms, wherein the 5-6 membered rings can be unsaturated or saturated and the rings contain 1 to 2 nitrogen atoms. Cocrystals of cannabidiol and a coformer selected from L-proline, D-proline, tetramethylpyrazine, and 4,4′-dipyridyl are also disclosed herein

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A solid form comprising cannabidiol and the coformer L-proline. 
     
     
         2 . The solid form of  claim 1  having an x-ray diffraction pattern (XRPD) comprising one or more peaks at 5.3, 5.8, 9.4, 10.7, 11.1, 11.4, 11.7, 12.3, 15.4, 15.8, 16.4, 17.3, 18.7, 19.2, 19.4, 20.0, 20.8, 21.3, 23.1, and 24.5 degrees 2θ±0.2. 
     
     
         3 . The solid form of  claim 3  having an x-ray powder diffraction pattern substantially similar to  FIG. 2 . 
     
     
         4 . The solid form of  claim 1  wherein the molar ratio of cannabidiol to L-proline is about 1:1. 
     
     
         5 . The solid form of  claim 1 , which is crystalline. 
     
     
         6 . The solid form of  claim 1 , which is a cocrystal. 
     
     
         7 . The solid form of  claim 6 , wherein the cocrystal is anhydrous. 
     
     
         8 . The solid form of  claim 1  having a DSC thermogram with a peak onset of about 146.4° C. or a peak maximum at about 147.8° C. 
     
     
         9 . The solid form of  claim 8  having a DSC thermogram which is substantially similar to the DSC thermogram of  FIG. 3 . 
     
     
         10 . A pharmaceutical composition comprising the solid form of  claim 1 . 
     
     
         11 . The pharmaceutical composition of  claim 10 , further comprising a pharmaceutically acceptable excipient or carrier. 
     
     
         12 . A solid form comprising cannabidiol and the coformer D-proline. 
     
     
         13 . The solid form of  claim 12  having an x-ray diffraction pattern comprising one or more peaks at 5.2, 5.8, 9.4, 10.6, 11.2, 11.5, 12.4, 12.7, 15.3, 15.7, 16.4, 17.4, 18.7, 19.2, 19.4, 20.2, 20.7, 21.2, 23.3, 24.0, 24.6, 25.6, and 26.2 degrees 2θ±0.2. 
     
     
         14 . The solid form of  claim 13  having an x-ray powder diffraction pattern substantially similar to  FIG. 7 . 
     
     
         15 . The solid form of  claim 12  wherein the molar ratio of cannabidiol to D-proline is about 1:1. 
     
     
         16 . The solid form of  claim 12 , which is crystalline. 
     
     
         17 . The solid form of  claim 12 , which is a cocrystal. 
     
     
         18 . The solid form of  claim 17 , wherein the cocrystal is anhydrous. 
     
     
         19 . The solid form of  claim 12  having a DSC thermogram with a peak onset of about 154.3° C. or a peak maximum at about 155.5° C. 
     
     
         20 . The solid form of  claim 19  having a DSC thermogram which is substantially similar to the DSC thermogram of  FIG. 8   
     
     
         21 . A pharmaceutical composition comprising the solid form of  claim 12 . 
     
     
         22 . The pharmaceutical composition of  claim 21 , further comprising a pharmaceutically acceptable excipient or carrier. 
     
     
         23 . A solid form comprising cannabidiol and the coformer tetramethylpyrazine. 
     
     
         24 . The solid form of  claim 23  having an x-ray diffraction pattern comprising one or more peaks at about 9.1, 14.6, 18.3, and 19.6 degrees 2θ±0.2. 
     
     
         25 . The solid form of  claim 24  having an x-ray powder diffraction pattern substantially similar to  FIG. 12 . 
     
     
         26 . The solid form of  claim 23 , wherein the molar ratio of cannabidiol to tetramethylpyrazine is about 1:1. 
     
     
         27 . The solid form of  claim 23 , which is crystalline. 
     
     
         28 . The solid form of  claim 23 , which is a cocrystal. 
     
     
         29 . The solid form of  claim 23  having a DSC thermogram with a peak onset of approximately 89.9° C. or a peak maximum at about 92.8° C. 
     
     
         30 . The solid form of  claim 29  having a DSC thermogram which is substantially similar to the DSC thermogram of  FIG. 13

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