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US 7,586,008 B2Granted
Propofol analogs, process for their preparation, and methods of use
AssigneeAbraxis BioScience, LLC
InventorsChunlin Tao, Cheng Zhi Yu, Neil P. Desai, Vuong Trieu
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Abstract
The invention provides para substituted dialkylphenol derivatives of propofol. The invention further provides pharmaceutical compositions comprising such analogs, methods for preparing such analogs, and methods of using such analogs to induce general anesthesia, sedation, and/or hypnotic or sleep effects in a patient.
Claims28
A compound of the formula
- wherein
- X is C═O and Y═H, R1 is C4-C20 aryl, R2 is hydrogen, and R3 is methyl, ethyl or propyl with the proviso that R1 is not phenyl.
A compound of the formula
- wherein
- R1 is selected from the group consisting of 4-fluorophenyl, 3-fluorophenyl, 2-fluorophenyl, 4-bromophenyl, 3-bromophenyl, 2-bromophenyl, 4-chlorophenyl, 3-chlorophenyl, 2-chlorophenyl, 4-trifluoromethylphenyl, 3-trifluoromethylphenyl, 2-trifluoromethylphenyl, 4-methoxyphenyl, 3-methoxyphenyl, 2-methoxyphenyl, 4-nitrophenyl, 3-nitrophenyl, 2-nitrophenyl, 4-cyanophenyl, 3-cyanophenyl, 2-methylphenyl, 4-methylphenyl, 3-chloromethylphenyl, 2-iodophenyl, 4-iodophenyl, 4-trifluoromethoxyphenyl, 3-propylphenyl, 2-ethylphenyl, 4-bromomethylphenyl, 4-dimethylaminophenyl, 4-biphenyl, 1-naphthalenyl, 2-naphthalenyl, 2-furanyl, 5-nitro-2-furanyl, 2-thiophenyl, 3,4-methylenedioxyphenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 3,5-dichlorophenyl, 2,5-bis(trifluoromethyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, 4-chloro-3-nitrophenyl, 5-bromo-2-methoxyphenyl, 4-methyl-3-nitrophenyl, 2-fluoro-3-trifluoromethylphenyl, 2-fluoro-5-trifluoromethylphenyl, 2-fluoro-6-trifluoromethylphenyl, 3-fluoro-4-trifluoromethylphenyl, 3-fluoro-5-trifluoromethylphenyl, 2,4-dimethoxyphenyl, 2,6-dimethoxyphenyl, 3,4-dimethoxyphenyl, 3,5-dimethoxyphenyl, 3,5-dichloro-4-methoxyphenyl, 2,3,4-trifluorophenyl, 2,3,6-trifluorophenyl, 2,4,5-trifluorophenyl, 2,4,6-trichlorophenyl, 2,4-dichloro-5-fluorophenyl, 3,4,5-trimethoxyphenyl, 2,4,5-trifluoro-3-methoxyphenyl, 2,3,4,5-tetrafluorophenyl, and pentafluorophenyl;
- R2 and R3 are C1-C6 alkyl;
- X is C═O, C═S, C═C, CR4R5, C(OR6)R7 or C═N—OR8;
- Y is hydrogen, COR4, COOR4, CONR4R5, COSR4 or phosphate;
- wherein R4, R5, R6, R7 and R8 are hydrogen or C1-C6 alkyl.
3 more elements
A compound of the formula
- wherein Y is phosphate;
- R1 is hydrogen, C1-C6 alkyl, or C4-C20 aryl;
- R2 and R3 are C1-C6 alkyl;
- X is C═O, C═S, C═C, CR4R5, C(OR6)R7 or C═N—OR8;
- wherein R4, R5, R6, R7 and R8 are hydrogen or C1-C6 alkyl;
- except when X is C═O and R2 and R3 are methyl, then R1 is not phenyl.
3 more elements
A compound of the formula
- wherein X is C═O, R1 is 4-chlorophenyl, and R2 and R3 are each methyl;
- Y is hydrogen, COR4, COOR4, CONR4R5, COSR4 or phosphate;
- and
- R4, R5, R6, R7 and R8 are hydrogen or C1-C6 alkyl.
1 more element
A compound of the formula
- wherein X is C═O and Y is H, R1 is 4-chlorophenyl, and R2 and R3 are each methyl;
- and
- R4, R5, R6, R7 and R8 are hydrogen or C1-C6 alkyl.
A compound of the formula
- wherein X is C═O, R1 is 4-trifluoromethylphenyl, and R2 and R3 are each methyl;
- Y is hydrogen, COR4, COOR4, CONR4R5, COSR4 or phosphate;
- and
- R4, R5, R6, R7 and R8 are hydrogen or C1-C6 alkyl.
1 more element
A compound of the formula
- wherein X is C═O and Y is H, R1 is 4-trifluoromethylphenyl, and R2 and R3 are each methyl;
- and
- R4, R5, R6, R7 and R8 are hydrogen or C1-C6 alkyl.
A compound of the formula
- wherein X is C═O, R1 is 4-iodophenyl, and R2 and R3 are each methyl;
- Y is hydrogen, COR4, COOR4, CONR4R5, COSR4 or phosphate;
- and
- R4, R5, R6, R7 and R8 are hydrogen or C1-C6 alkyl.
1 more element
A compound of the formula
- wherein X is C═O and Y is H, R1 is 4-iodophenyl, and R2 and R3 are each methyl;
- and
- R4, R5, R6, R7 and R8 are hydrogen or 1-6 alkyl.
Dependencies are inferred from the claim text.