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US 6,608,100 B1Granted
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
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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.
Claims10
A compound selected from the group consisting of a compound of formula Ia
- and when the compound of formula Ia 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 R2A, R2A′, 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 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 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,
- wherein each m is independently 0 or 1,
- wherein n is 3 or 4,
- wherein each o is independently 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.
6 more elements
A compound of formula
- or a K, Na and Cs salt thereof.
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.
A compound of formula
- or a pharmaceutically acceptable ammonium, K, Na and Cs salt thereof.
A compound of formula
- or a pharmaceutically acceptable ammonium, K, Na and Cs salt thereof.
A compound of formula
- or a pharmaceutically acceptable ammonium, K, Na and Cs salt thereof.
A compound of formula
- or a K, Na and Cs salt thereof, thereof, wherein Cx is selected from the group consisting of —COOH and —CH2OH.
A compound selected from the group consisting of a compound of formula Ia″
- and when the compound of formula Ia″ 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 R2A 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 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—, 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,
- provided that when Cx is CH2OH, R5A is not indole-3-CH2—.
4 more elements
Dependencies are inferred from the claim text.