Thiocolchicine derivatives, method of making and methods of use thereof
View Patent ↗Disclosed herein are thiocolchicine derivatives suitable for use as muscle relaxants, methods of making the derivatives, and compositions comprising the derivatives.
1. A compound according to structure (I)
wherein R is
b.) an amino acid derivative linked through the carboxylate group selected from the group consisting of alanine and tyrosine;
c.) —CH 2 —O(C═O)R 2 where R 2 is methyl, ethyl, n-propyl, isopropyl and * is in the S configuration;
d.) —C(═O)R 3 , where R 3 is pyridyl and * is in the S configuration; or
f.) —C(═O)(CH 2 ) x SO 3 R 4 where R 4 is hydrogen or C 1 -C 3 alkyl, x is 1 or 2 and * is in the S configuration;
or a pharmaceutically acceptable salt, crystalline form, non-crystalline form, or stereoisomer thereof.
2. The compound of claim 1 , wherein R is
b.) an amino acid derivative linked through the carboxylate group selected from the group consisting of alanine and tyrosine,
or a pharmaceutically acceptable salt, crystalline form, or non-crystalline form thereof.
3. The compound of claim 1 , comprising the S isomer, wherein R is
c.) —CH 2 —O(C═O)R 2 where R 2 is methyl, ethyl, n-propyl, or isopropyl,
or a pharmaceutically acceptable salt, crystalline form, or non-crystalline form thereof.
4. The compound of claim 1 , comprising the S isomer, wherein R is
d.) —C(═O)R 3 , where R 3 is pyridyl,
or a pharmaceutically acceptable salt, crystalline form, or non-crystalline form thereof.
5. The compound of claim 1 , comprising the S isomer, wherein R is
f.) —C(═O)(CH 2 ) x SO 3 R 4 where R 4 is hydrogen or C 1 -C 3 alkyl and x is 1 or 2,
or a pharmaceutically acceptable salt, crystalline form, or non-crystalline form thereof.
6. The compound of claim 1 , wherein the compound is