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US 6,632,816 B1Granted
Aromatic derivatives as HIV aspartyl protease inhibitors
AssigneePharmacor Inc.
InventorsBrent Richard Stranix, Jean-François Lavallée, Nicolas LeBerre, Valérie Perron
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Abstract
The present invention provides HIV aspartyl protease inhibitors of the formula; and when the compound of formula I comprises an amino group, pharmaceutically acceptable ammonium salts thereof, wherein n is 3 or 4, wherein R1 may be, for example, iso-butyl, wherein X and Y, same or different, may be, for example, NH2 and F, and wherein R2 and R3 are as defined herein.
Claims62
A compound of formula I
- and when the compound of formula I comprises an amino group, pharmaceutically acceptable ammonium salts thereof,
- wherein n is 3 or 4,
- wherein X and Y, the same or different, are selected from the group consisting of H, a straight alkyl group of 1 to 6 carbon atoms, a branched alkyl group of 3 to 6 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, F, Cl, Br, I, —CF3, —OCF3, —CN, —NO2, —NR4R5, —NHCOR4, —OR4, —SR4, —COOR4, —COR4, and —CH2OH or X and Y together define an alkylenedioxy group selected from the group consisting of a methylenedioxy group of formula —OCH2O— and an ethylenedioxy group of formula —OCH2CH2O—,
- wherein R1 is selected from the group consisting of a straight alkyl group of 1 to 6 carbon atoms, a branched alkyl group of 3 to 6 carbon atoms, a cycloalkylalkyl group having 3 to 6 carbon atoms in the cycloalkyl part thereof and 1 to 3 carbon atoms in the alkyl part thereof,
- wherein R2 is selected from the group consisting of H, a straight alkyl group of 1 to 6 carbon atoms, a branched alkyl group of 3 to 6 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, and a group of formula R2A—CO—, R2A being selected from the group consisting of a straight or branched alkyl group of 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a cycloalkylalkyl group having 3 to 6 carbon atoms in the cycloalkyl part thereof and 1 to 3 carbon atoms in the alkyl part thereof, an alkyloxy group of 1 to 6 carbon atoms, tetrahydro-3-furanyloxy, —CH2OH, —CF3, —CH2CF3, —CH2CH2CF3, pyrrolidinyl, piperidinyl, 4-morpholinyl, CH3O2C—, CH3O2CCH2—, Acetyl-OCH2CH2—, HO2CCH2—, 3-hydroxyphenyl, 4-hydroxyphenyl, 4-CH3OC6H4CH2—, CH3NH—, (CH3)2N—, (CH3CH2)2N—, (CH3CH2CH2)2N—, HOCH2CH2NH—, CH3OCH2O—, CH3OCH2CH2O—, C6H5CH2O—, 2-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl-, 2-pyrazinyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 2-quinoxalinyl, a phenyl group of formula
- a picolyl group selected from the group consisting of
- a picolyloxy group selected from the group consisting of
- a substituted pyridyl group selected from the group consisting of
- a group selected from the group consisting of
- wherein X′ and Y′, the same or different, are selected from the group consisting of H, a straight alkyl group of 1 to 6 carbon atoms, a branched alkyl group of 3 to 6 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, F, Cl, Br, I, —CF3, —NO2, —NR4R5, —NHCOR4, —OR4, —SR4, —COOR4, —COR4 and —CH2OH,
- wherein R4 and R5, the same or different, are selected from the group consisting of H, a straight alkyl group of 1 to 6 carbon atoms, a branched alkyl group of 3 to 6 carbon atoms, and a cycloalkyl group of 3 to 6 carbon atoms,
- wherein R3 is selected from the group consisting of a diphenylmethyl group of formula IV
- a naphthyl-1-CH2— group of formula V
- a naphthyl-2-CH2— group of formula VI
- a biphenylmethyl group of formula VII
- and an anthryl-9-CH2— group of formula VIII
13 more elements
A compound of formula II,
- and when the compound of formula II comprises an amino group, pharmaceutically acceptable ammonium salts thereof,
- wherein n is 3 or 4,
- wherein X and Y, the same or different, are selected from the group consisting of H, a straight alkyl group of 1 to 6 carbon atoms, a branched alkyl group of 3 to 6 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, F, Cl, Br, I, —CF3, —OCF3, —CN, —NO2, —NR4R5, —NHCOR4, —OR4, —SR4, —COOR4, —COR4, and —CH2OH or X and Y together together define an alkylenedioxy group selected from the group consisting of a methylenedioxy group of formula —OCH2O— and an ethylenedioxy group of formula —OCH2CH2O—,
- wherein R1 is selected from the group consisting of a straight alkyl group of 1 to 6 carbon atoms, a branched alkyl group of 3 to 6 carbon atoms, a cycloalkylalkyl group having 3 to 6 carbon atoms in the cycloalkyl part thereof and 1 to 3 carbon atoms in the alkyl part thereof,
- wherein R2 is selected from the group consisting of H, a straight alkyl group of 1 to 6 carbon atoms, a branched alkyl group of 3 to 6 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, and a group of formula R2A—CO—, R2A being selected from the group consisting of a straight or branched alkyl group of 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a cycloalkylalkyl group having 3 to 6 carbon atoms in the cycloalkyl part thereof and 1 to 3 carbon atoms in the alkyl part thereof, an alkyloxy group of 1 to 6 carbon atoms, tetrahydro-3-furanyloxy, —CH2OH, —CF3, —CH2CF3, —CH2CH2CF3, pyrrolidinyl, piperidinyl, 4-morpholinyl, CH3O2C—, CH3O2CCH2—, Acetyl-OCH2CH2—, HO2CCH2—, 3-hydroxyphenyl, 4-hydroxyphenyl, 4-CH3OC6H4CH2—, CH3NH—, (CH3)2N—, (CH3CH2)2N—, (CH3CH2CH2)2N—, HOCH2CH2NH—, CH3OCH2O—, CH3OCH2CH2O—, C6H5CH2O—, 2-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl-, 2-pyrazinyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 2-quinoxalinyl, a phenyl group of formula
- a picolyl group selected from the group consisting of
- a picolyloxy group selected from the group consisting of
- a substituted pyridyl group selected from the group consisting of
- a group selected from the group consisting of
- wherein X′ and Y′, the same or different, are selected from the group consisting of H, a straight alkyl group of 1 to 6 carbon atoms, a branched alkyl group of 3 to 6 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, F, Cl, Br, I, —CF3, —NO2, —NR4R5, —NHCOR4, —OR4, —SR4, —COOR4, —COR4 and —CH2OH,
- wherein R4 and R5, the same or different, are selected from the group consisting of H, a straight alkyl group of 1 to 6 carbon atoms, a branched alkyl group of 3 to 6 carbon atoms, and a cycloalkyl group of 3 to 6 carbon atoms,
- wherein R3 is selected from the group consisting of a diphenylmethyl group of formula IV
- a naphthyl-1-CH2— group of formula V
- a naphthyl-2-CH2— group of formula VI
- a biphenylmethyl group of formula VII
- and an anthryl-9-CH2— group of formula VIII
13 more elements
Dependencies are inferred from the claim text.