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US 6,610,689 B2Granted
HIV protease inhibitors based on amino acid derivatives
AssigneePharmacor Inc.
InventorsBrent Richard Stranix, Gilles Sauvé, Abderrahim Bouzide, Alexandre Coté, Gervais Bérubé, Patrick Soucy, Yongsen Zhao, Jocelyn Yelle
Life of this patent
Estimating the term…
Abstract
A compound selected from the group consisting of a compound of formula I a compound of formula II and when the compound of formula I and II comprises an amino group pharmaceutically acceptable ammonium salts thereof, wherein R1, R2, Cx, n, R3, R4, R5, Y are as defined in the specification.
Claims22
A compound selected from the group consisting of a compound of formula Id
- and when the compound of formula Id has an amino group pharmaceutically acceptable ammonium salts thereof,
- wherein Cx is selected from the group consisting of —COOM and —CH2OH, M being an alkali metal or alkaline earth metal,
- wherein R1A is selected from the group consisting of a straight or branched alkyl group of 1 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 R4A and R4A ′ are independently selected from the group consisting of H, a straight or branched alkyl group of 1 to 4 carbon atoms, F, Cl, Br, I, —CF3, —NO2, —NR10R11, —NHCOR10, —OR10, —OCH2C6H5, —SR10, —COOR10, —COR10 and —CH2OH,
- wherein R4C is selected from the group consisting of a straight or branched alkyl group of 1 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, CF3, pyrrolidine, 4-morpholine, tetrahydro-3-furanyloxy, 4-CH3OC6H4NH—, CH3NH—, HOCH2CH2NH—, 9-fluorenyl-CH2O—, tert-butylO—, iso-butylO—, C6H5CH2O—, CH3O—, unsubstituted C6H5—, C6H5— substituted by one or more members selected from the group consisting of F, Cl, Br, I, —CF3, —NO2, —NR10R11, —NHCOR10, —OR10, —SR10, —COOR10, —COR10 and —CH2OH, unsubstituted C6H5CH2—, C6H5CH2— substituted by one or more members selected from the group consisting of F, Cl, Br, I, —CF3, —NO2, —NR10R11, —NHCOR10, —OR10, —SR10, —COOR10, —COR10 and —CH2OH, unsubstituted C6H5CH2CH2—, and C6H5CH2CH2— substituted by one or more members selected from the group consisting of F, Cl, Br, I, —CF3, —NO2, —NR10R11, —NHCOR10, —OR10, —SR10, —COOR10, —COR10 and —CH2OH,
- wherein R5A is selected from the group consisting of H, a straight or branched alkyl group of 1 to 8 carbon atoms, HOCH2—, C6H5CH2OCH2—, benzyl-OCH(CH3), HO2CCH2—, HO2CCH2CH2—, NC—CH2—, H2NC(O)CH2—, H2NC(O)CH2CH2—, 4-CH3C6H4CH2SCH2—, CH3SCH2CH2—, H2NCH2CH2CH2CH2—, C6H5—, C6H5CH2—, C6H5CH(OH)—, C6H5CH(CN)—, C6F5CH2—, 4-(9-fluorenylmethoxycarbonyl)-NHCH2—C6H4CH2— and benzyl substituted by group selected from the group consisting of H, a straight or branched alkyl group of 1 to 4 carbon atoms, F, Cl, Br, I, —CF3, —NO2, —NR10R11, —NHCOR10, —OR10, —OCH2C6H5, —SR10, —COOR10, —COR10 and —CH2OH,
- wherein m is 0 or 1,
- wherein n is 3 or 4,
- wherein o is 0 or 1,
- and wherein R10 and R11 are independently selected from the group consisting of H, a straight or branched alkyl group of 1 to 4 carbon atoms.
7 more elements
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a pharmaceutically acceptable ammoinum, K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a pharmaceutically acceptable ammonium, K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a pharmaceutically acceptable ammonium, K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a pharmaceutically acceptable ammonium, K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a pharmaceutically acceptable amnonium, K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a pharmaceutically acceptable ammoniumn, K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of formula
- or a pharmaceutically acceptable ammonium, K, Na and Cs salt thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound of selected from the group consisting of a compound of formula Id″
- and when the compound of formula Id″ has an amino group pharmaceutically acceptable ammonium salts thereof,
- wherein Cx is selected from the group consisting of —COOM and —CH2OH, M being an alkali metal or alkaline earth metal,
- wherein R1A is selected from the group consisting of a straight or branched alkyl group of 1 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 R4A is selected from the group consisting of H, a straight or branched alkyl group of 1 to 4 carbon atoms, F, Cl, Br, I, —CF3, —NO2, —NR10R11, —NHCOR10, —OR10, —OCH2C6H5, —SR10, —COOR10, —COR10 and —CH2OH,
- wherein R4C is selected from the group consisting of a straight or branched alkyl group of 1 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, CF3, pyrrolidine, 4-morpholine, tetrahydro-3-furanyloxy, 4-CH3OC6H4NH—, CH3NH—, HOCH2CH2NH—, 9-fluorenyl-CH2O—, tert-butylO—, iso-butylO—, C6H5CH2O—, CH3O—, unsubstituted C6H5—, C6H5— substituted by one or more members selected from the group consisting of F, Cl, Br, I, —CF3, —NO2, —NR10R11, —NHCOR10, —OR10, —SR10, —COOR10, —COR10 and —CH2OH, unsubstituted C6H5CH2—, C6H5CH2—, substituted by one or more members selected from the group consisting of F, Cl, Br, I, —CF3, —NO2, —NR10R11, —NHCOR10, —OR10, —SR10, —COOR10, —COR10 and —CH2OH, unsubstituted C6H5CH2CH2—, and C6H5CH2CH2— substituted by one or more members selected from the group consisting of F, Cl, Br, I, —CF3, —NO2, —NR10R11, —NHCOR10, —OR10, —SR10, —COOR10, —COR10 and —CH2OH,
- wherein R5A is selected from the group consisting of H, a straight or branched alkyl group of 1 to 8 carbon atoms, HOCH2—, C6H5CH2OCH2—, benzyl-OCH(CH3), HO2CCH2—, HO2CCH2CH2—, NC—CH2—, H2NC(O)CH2—, H2NC(O)CH2CH2—, 4-CH3C6H4CH2SCH2—, CH3SCH2CH2—, H2NCH2CH2CH2CH2—, C6H5—, C6H5CH2—, C6H5CH(OH)—, C6H5CH(CN)—, C6F5CH2—, 4-(9-fluorenyhethoxycarbonyl)-NHCH2—C6H4CH2—, C5H4N-2-CH2—, C5H4N-3-CH2—, C5H4N-4-CH2—, 2-thiophene-CH2—, indole-3-CH2—, 2-benzothiophene-CH2—, Nτ-benzyl-imidazole-4-CH2— , imidazole-4-CH2—, thiazole-4-CH2—, and benzyl substituted by a group selected from the group consisting of H, a straight or branched alkyl group of 1 to 4 carbon atoms, F, Cl, Br, I, —CF3, —NO2, —NR10R11, —NHCOR10, —OR10, —OCH2C6H5, —SR10, —COOR10, —COR10 and —CH2OH,
- and wherein R10 and R11 are independently selected from the group consisting of H, a straight or branched alkyl group of 1 to 4 carbon atoms.
4 more elements
Dependencies are inferred from the claim text.