Synthetic cannabinoid analogs, pharmaceutical compositions, and methods of treating bacterial infections and other disorders
AssigneeMiralogx LLC
InventorJonnie R. Williams, SR.
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Abstract
Cannabinoid analogs disclosed herein may exhibit antibacterial and anti-inflammatory properties. Pharmaceutical compositions comprising the cannabinoid analogs may be used to treat bacterial infections, including methicillin-resistant Staphylococcus aureus (MRSA) infections, as well as various disorders associated with chronic inflammation, such as arthritis. In some aspects, a pharmaceutical composition may be administered to an individual who has been exposed or is at risk of exposure to Bacillus anthracis or Bacillus anthracis spores.
Claims30
-5. (canceled)
A compound having a structure of Formula (VI):
- wherein R1, R2, R3 and R4 are each independently selected from the group consisting of H, OH, protected hydroxyl, alkyl, alkenyl, alkynyl, acyl, aryl, heteroaryl, cycloalkyl, and heterocycle;
- wherein the alkyl, alkenyl, alkynyl or acyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, OH, alkyl, —O-alkyl, NRARB, —S-alkyl, —SO-alkyl, —SO2-alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, and heterocycle;
- wherein RA and RB are each independently selected from hydrogen and C1-4 alkyl;
- wherein the aryl or heteroaryl, whether alone or as part of a substituent group, is optionally substituted with one or more substituents independently selected from the group consisting of halogen, —OH, alkyl, —O-alkyl, —COH, —C(O)—C1-4 alkyl, —C(O)O C1-4 alkyl, —NRCRD, —S-alkyl, —SO-alkyl and —SO2-alkyl;
- wherein RC and RD are each independently selected from hydrogen and C1-4 alkyl;
- or a pharmaceutically acceptable salt, ester or ether thereof.
(canceled)
-20. (canceled)
A compound having a structure of Formula (VII):
- wherein R2, R3 and R4 are each independently selected from the group consisting of H, OH, protected hydroxyl, alkyl, alkenyl, alkynyl, acyl, aryl, heteroaryl, cycloalkyl, and heterocycle;
- wherein the alkyl, alkenyl, alkynyl or acyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, OH, alkyl, —O-alkyl, NRARB, —S-alkyl, —SO-alkyl, —SO2-alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, and heterocycle;
- wherein RA and RB are each independently selected from hydrogen and C1-4 alkyl;
- wherein the aryl or heteroaryl, whether alone or as part of a substituent group, is optionally substituted with one or more substituents independently selected from the group consisting of halogen, —OH, alkyl, —O-alkyl, —COH, —C(O)—C1-4 alkyl, —C(O)O—C1-4 alkyl, NRCRD, —S-alkyl, —SO-alkyl and —SO2-alkyl;
- wherein RC and RD are each independently selected from hydrogen and C1-4 alkyl;
- or a pharmaceutically acceptable salt, ester or ether thereof.
A compound having a structure selected from the group consisting of:
- or a pharmaceutically acceptable salt, ester or ether thereof.
A method of treating a bacterial infection comprising administering to an individual in need thereof a therapeutically effective amount of a compound of Formula (I):
- wherein R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from the group consisting of H, OH, protected hydroxyl, alkyl, alkenyl, alkynyl, acyl, aryl, heteroaryl, cycloalkyl, and heterocycle;
- wherein the alkyl, alkenyl, alkynyl or acyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, —OH, alkyl, —O-alkyl, NRARB, —S-alkyl, —SO-alkyl, —SO2-alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, and heterocycle;
- wherein RA and RB are each independently selected from hydrogen and C1-4 alkyl;
- wherein the aryl or heteroaryl, whether alone or as part of a substituent group, is optionally substituted with one or more substituents independently selected from the group consisting of halogen, OH, alkyl, —O-alkyl, —COH, —C(O)—C1-4 alkyl, —C(O)O—C1-4 alkyl, —NRCRD, —S-alkyl, —SO-alkyl and —SO2-alkyl;
- wherein RC and RD are each independently selected from hydrogen and C1-4 alkyl;
- or a pharmaceutically acceptable salt, ester or ether thereof.
A method of treating a viral infection comprising administering to an individual in need thereof a therapeutically effective amount of a compound of Formula (I):
- wherein R1, R2, R3, R4, R5, R6, R7, and R8 are each independently selected from the group consisting of H, OH, protected hydroxyl, alkyl, alkenyl, alkynyl, acyl, aryl, heteroaryl, cycloalkyl, and heterocycle;
- wherein the alkyl, alkenyl, alkynyl or acyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, —OH, alkyl, —O-alkyl, NRARB, —S-alkyl, —SO-alkyl, —SO2-alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, and heterocycle;
- wherein RA and RB are each independently selected from hydrogen and C1-4 alkyl;
- wherein the aryl or heteroaryl, whether alone or as part of a substituent group, is optionally substituted with one or more substituents independently selected from the group consisting of halogen, OH, alkyl, —O-alkyl, —COH, —C(O)—C1-4 alkyl, —C(O)O—C1-4 alkyl, NRCRD, —S-alkyl, —SO-alkyl and —SO2-alkyl;
- wherein RC and RD are each independently selected from hydrogen and C1-4 alkyl;
- or a pharmaceutically acceptable salt, ester or ether thereof.
Dependencies are inferred from the claim text.