Biologically active cannabidiol analogs

Patent metadata

Field	Value
Publication number	US-11337950-B2
Application number	US-202016896239-A
Country	US
Kind code	B2
Filing date	Jun 9, 2020
Priority date	Jan 29, 2016
Publication date	May 24, 2022
Grant date	May 24, 2022

Abstract

Biologically active cannabidiol analogs comprising a compound of the formulawherein one of R1 or R2 or both is/are the residue of a moiety formed by the reaction of an amino group of the amino acid ester of R1 or R2 or both with a dicarboxylic acid or a dicarboxylic acid derivative and the other R1 or R2 (in the case of the mono) is the residue of a dicarboxylic acid or dicarboxylic acid derivative or Hydrogen (H), (i.e. underivatized), and salts thereof. These CBD analogs are be useful in pain management in oncology and other clinical settings in which neuropathy is presented. Furthermore, these CBD-analogs are useful in blocking the addictive properties of opiates.

First claim

What we claim is:

1. A pharmaceutical composition for analgesic treatment comprising a biologically active cannabidiol analog
or a pharmaceutically acceptable salt thereof;
wherein the analog is CBD-Di-Alaninate-Di-Hemisuccinate, CBD-Di-Valinate-Di-Hemisuccinate, CBD-Monovalinate-Di-Hemisuccinate, or CBD-Mono-Valinate-Mono-Hemisuccinate having the formula

wherein at least one R 1 and R 2 is:

and the other of R 1 and R 2 is H, or both of R 1 and R 2 are:

2. The pharmaceutical composition of claim 1 wherein the analog is CBD-Divalinate-Di-Hemisuccinate, having the formula

3. The pharmaceutical composition of claim 1 wherein the analog is CBD-Monovalinate-Di-Hemisuccinate, having the formula

4. The pharmaceutical composition of claim 1 wherein the analog is CBD-Monovalinate-Mono-Hemisuccinate, having the formula

wherein at least one R 1 and R 2 is:

and the other of R 1 and R 2 is H, or both of R 1 and R 2 are:

5. The pharmaceutical composition of claim 1 comprising the biologically active cannabidiol analog of claim 1 in a pharmaceutically acceptable carrier.

6. The pharmaceutical composition of claim 4 comprising the biologically active cannabidiol analog of claim 4 in a pharmaceutically acceptable carrier.

7. The pharmaceutical composition for analgesic treatment in combination with a sub-analgesic dose of morphine in cisplatin induced neuropathy comprising the biologically active cannabidiol analog of claim 1 in a pharmaceutically acceptable carrier.

8. The pharmaceutical composition of claim 7 , wherein the sub-analgesic dose of morphine is 0.1 mg per kg of body weight of a subject treated with the pharmaceutical composition.

9. The pharmaceutical composition of claim 7 , wherein the biologically active cannabidiol analog is present in an amount of 2.0 mg per kg of body weight of a subject treated with the pharmaceutical composition.

10. The pharmaceutical composition of claim 1 , wherein the pharmaceutical composition is in the form of a suppository.

Assignees

• Univ Mississippi

Inventors

• Elsohly Mahmoud A
• Majumdar Soumyajit
• Gul Waseem
• Ashfaq Mohammad Khalid
• Sufka Kenneth Joseph
• Harris Hannah Marie

Classifications

• A61K31/223 Primary

  of alpha-aminoacids · CPC title

• A61K31/658

  o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• C07C233/47

  having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton · CPC title