Ketamine derivatives and compositions thereof
AssigneeXw Laboratories Inc.
InventorsJia-Ning Xiang, Xuesong Xu, Hao-Wei Shih, Wai-Si Eng
Life of this patent
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Abstract
Ketamine derivatives and pharmaceutical compositions thereof are disclosed. When administered orally the ketamine derivatives provide increased bioavailability of ketamine in the systemic circulation. The ketamine derivatives can be used to treat neurological diseases, psychological diseases and pain.
Claims30
A method of providing a therapeutically effective concentration of ketamine in a patient's blood for treating pain comprising administering to the patient in need thereof, a compound of Formula (1):
- or a pharmaceutically acceptable salt thereof, wherein,
- R1 is selected from hydrogen and C1-6 alkyl;
- and
- R2 is selected from a moiety of Formula (2), a moiety of Formula (3), a moiety of Formula (4), and a moiety of Formula (5):
- wherein,
- R3 is selected from hydrogen, C1-6 alkyl, C7-12 alkylarene, and substituted C7-12 alkylarene;
- R4 is selected from hydrogen and C1-6 alkyl;
- R5 is selected from hydrogen, C1-6 alkyl, —C(═O)—R10, and —C(═O)—O—R10, wherein R10 is selected from C1-6 alkyl, C3-6 cycloalkyl, and —CF3;
- R6 is selected from C1-6 alkyl and C1-6 alkoxy;
- n is an integer from 0 to 3;
- R7 is selected from C1-6 alkyl, —C(═O)—R11, and —C(═O)—O—R10, wherein,
- R10 is selected from C1-6 alkyl and C3-6 cycloalkyl;
- and
- R11 is selected from —NH2, —CF3, C1-6 alkyl, and C3-6 cycloalkyl;
- and
- R9 is selected from hydrogen and C1-3 alkyl.
A method of treating pain in a patient comprising administering to a patient in need thereof, a therapeutically effective amount of the compound of Formula (1):
- or a pharmaceutically acceptable salt thereof, wherein,
- R1 is selected from hydrogen and C1-6 alkyl;
- and
- R2 is selected from a moiety of Formula (2), a moiety of Formula (3), a moiety of Formula (4), and a moiety of Formula (5):
- wherein,
- R3 is selected from hydrogen, C1-6 alkyl, C7-12 alkylarene, and substituted C7-12 alkylarene;
- R4 is selected from hydrogen and C1-6 alkyl;
- R5 is selected from hydrogen, C1-6 alkyl, —C(═O)—R10, and —C(═O)—O—R10 wherein R10 is selected from C1-6 alkyl, C3-6 cycloalkyl, and —CF3;
- R6 is selected from C1-6 alkyl and C1-6 alkoxy;
- n is an integer from 0 to 3;
- R7 is selected from C1-6 alkyl, —C(═O)—R11, and —C(═O)—O—R10, wherein,
- R10 is selected from C1-6 alkyl and C3-6 cycloalkyl;
- and
- R11 is selected from —NH2, —CF3, C1-6 alkyl, and C3-6 cycloalkyl;
- and
- R9 is selected from hydrogen and C1-3 alkyl.
A method of providing a therapeutically effective concentration of ketamine in a patient's blood for treating pain comprising administering to the patient in need thereof, a pharmaceutical composition comprising a compound of Formula (1):
- or a pharmaceutically acceptable salt thereof, wherein,
- R1 is selected from hydrogen and C1-6 alkyl;
- and
- R2 is selected from a moiety of Formula (2), a moiety of Formula (3), a moiety of Formula (4), and a moiety of Formula (5):
- wherein,
- R3 is selected from hydrogen, C1-6 alkyl, C7-12 alkylarene, and substituted C7-12 alkylarene;
- R4 is selected from hydrogen and C1-6 alkyl;
- R5 is selected from hydrogen, C1-6 alkyl, —C(═O)—R10, and —C(═O)—O—R10 wherein R10 is selected from C1-6 alkyl, C3-6 cycloalkyl, and —CF3;
- R6 is selected from C1-6 alkyl and C1-6 alkoxy;
- n is an integer from 0 to 3;
- R7 is selected from C1-6 alkyl, —C(═O)—R11, and —C(═O)—O—R10, wherein,
- R10 is selected from C1-6 alkyl and C3-6 cycloalkyl;
- and
- R11 is selected from —NH2, —CF3, C1-6 alkyl, and C3-6 cycloalkyl;
- and
- R9 is selected from hydrogen and C1-3 alkyl.
A method of treating pain in a patient comprising administering to a patient in need thereof, a therapeutically effective amount of a pharmaceutical composition comprising the compound of Formula (1):
- or a pharmaceutically acceptable salt thereof, wherein,
- R1 is selected from hydrogen and C1-6 alkyl;
- and
- R2 is selected from a moiety of Formula (2), a moiety of Formula (3), a moiety of Formula (4), and a moiety of Formula (5):
- wherein,
- R3 is selected from hydrogen, C1-6 alkyl, C7-12 alkylarene, and substituted C7-12 alkylarene;
- R4 is selected from hydrogen and C1-6 alkyl;
- R5 is selected from hydrogen, C1-6 alkyl, —C(═O)—R10, and —C(═O)—O—R10 wherein R10 is selected from C1-6 alkyl, C3-6 cycloalkyl, and —CF3;
- R6 is selected from C1-6 alkyl and C1-6 alkoxy;
- n is an integer from 0 to 3;
- R7 is selected from C1-6 alkyl, —C(═O)—R11, and —C(═O)—O—R10, wherein,
- R10 is selected from C1-6 alkyl and C3-6 cycloalkyl;
- and
- R11 is selected from —NH2, —CF3, C1-6 alkyl, and C3-6 cycloalkyl;
- and
- R9 is selected from hydrogen and C1-3 alkyl.
Dependencies are inferred from the claim text.