US2019345087A1PendingUtilityA1
Bio-stable cannabinoid compounds and methods for enhancing their physiological concentration
Est. expiryNov 15, 2036(~10.3 yrs left)· nominal 20-yr term from priority
C07C 2601/16C12P 7/22C12Y 121/03008C12N 9/0004C07C 65/28C07C 43/23A61P 25/00
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Claims
Abstract
The present disclosure provides biostable cannabinoid compounds according to Formula and methods for synthesizing and enhancing the biological concentrations of the compounds, where R 1 , R 2 , and R 3 are defined as set forth in the disclosure.
Claims
exact text as granted — not AI-modifiedWe claim:
1 . A pharmaceutical composition comprising a compound according to Formula I or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof:
wherein
R 1 is —H, —COOR 4 , or —(CH 2 ) n COOH;
R 2 is selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl;
R 3 is (C 1 -C 10 )halo alkyl, (C 3 -C 10 )cycloalkyl, (C 3 -C 10 )cycloalkyl-(C 1 -C 10 )alkylene, —CH 2 —CH 2 —[O—CH 2 —CH 2 —] m O—CH 2 —CH 2 —R b , —(CHR a ) q —NH 2 , and —(CHR a ) q —NH + 3 X − ;
R a is selected from the group consisting of —H, —OH, halogen, (C 1 -C 5 ) alkyl, and alkoxy;
R b is selected from the group consisting of —OH, —O(C 1 -C 5 ) alkyl, —(C 2 -C 6 ) alkene, azide, and —(C 2 -C 6 ) alkyne;
R 4 is —H or (C 1 -C 10 )
X is a counter ion derived from a pharmaceutically acceptable acid; and
n, m and q are each independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 and a pharmaceutically acceptable carrier.
2 . The pharmaceutical composition according to claim 1 , wherein R 1 is —H and R 2 is propyl or pentyl.
3 . The pharmaceutical composition according to claim 1 , wherein R 3 is (C 1 -C 10 )haloalkyl, —CH 2 —CH 2 —[O—CH 2 —CH 2 —] m O—CH 2 —CH 2 —OH, —(CH 2 ) q —NH 2 , or —(CH 2 ) q —NH + 3 X − .
4 . The pharmaceutical composition according to claim 3 , wherein R 3 is (C 1 -C 10 )haloalkyl.
5 . The pharmaceutical composition according to claim 4 , wherein R 3 is fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, fluoropropyl, fluorobutyl, fluoro-t-butyl, 1,1-difluoro-t-butyl, 1,2-difluoro-t-butyl, 1,2,3-trifluoro-t-butyl, and 1,1,2-trifluoro-t-butyl.
6 . The pharmaceutical composition according to claim 3 , wherein R 3 is —(CH 2 ) 2 —[O—CH 2 —CH 2 —] m O—(CH 2 ) 2 —OH and m is 2 or 3.
7 . The pharmaceutical composition according to claim 3 , wherein R 3 is —(CHR a ) q —NH + 3 X − and R a is —H.
8 . The pharmaceutical composition according to claim 7 , wherein R 3 is —(CH 2 ) 4 —NH + 3 X − , —(CH 2 ) 5 —NH + 3 X − , —(CH 2 ) 6 —NH + 3 X − , or —(CH 2 ) 7 —NH + 3 X − .
9 . The pharmaceutical composition according to claim 1 , wherein the compound, or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, is one selected from the following table:
10 . A compound, or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, selected from the following table:
11 . The compound, or a pharmaceutically acceptable salt, solvate, or stereoisomer thereof, according to claim 10 , selected from the following table:
12 . A method for producing a compound according to Formula IIa or a pharmaceutically acceptable salt, solvate, or stereoisorner thereof,
comprising:
(i) contacting a compound of Formula III
with a recombinant cannabinoid synthase in the presence of a solvent to produce a compound according to Formula II
and then
(ii) contacting the Formula II compound with a suitable Y—R 8 group to produce a compound according to Formula IIa;
wherein
R 5 is —COOR 9 , or
(CH 2 ) n COOH;
R 6 is selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl;
R 7 is —H;
R 8 is is optionally substituted (C 1 -C 10 ) alkyl, (C 1 -C 10 )haloalkyl, optionally substituted (C 3 -C 10 )aryl, optionally substituted (C 3 -C 10 )cycloalkyl, optionally substituted (C 3 -C 10 )aryl-(C 1 -C 10 )alkylene, optionally substituted (C 3 -C 10 )cycloalkyl-(C 1 -C 10 )alkylene, optionally substituted —CH 2 —CH 2 —[O—CH 2 —CH 2 —] m O—CH 2 —CH 2 —R b , optionally substituted. —(CHR a ) q —NH 2 , and optionally substituted —(CHR a ) q —NH + 3 X − ;
R a is selected from the group consisting of —H,
OH, halogen, (C 1 -C 5 ) alkyl, and alkoxy;
R b is selected from the group consisting of
OH, -O(C 1 -C 5 ) alkyl,
(C 2 -C 6 ) alkene, azide, and —(C 2 -C 6 ) alkyne;
R 9 is —H or (C 1 -C 10 ) alkyl;
X is a counter ion derived from a pharmaceutically acceptable acid;
Y is a leaving group; and
n, m and q are each independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
13 . The method of claim 9 , wherein the recombinant cannabinoid synthase is a recombinant cannabidiolic acid synthase (CBDA synthase).Cited by (0)
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