Amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors

Compound represented by the formula:

• or a pharmaceutically acceptable salt, prodrug or ester thereof, wherein
• R1 represents an alkyl of 1-5 carbon atoms, an alkenyl of 2-5 carbon atoms, an alkynyl of 2-5 carbon atoms, a hydroxyalkyl of 1-3 carbon atoms, an alkoxyalkyl of 1-3 alkyl and 1-3 alkoxy carbon atoms, a cyanoalkyl of 1-3 alkyl carbon atoms, imidazolylmethyl —CH2CONH2, —CH2CH2CONH2, —CH2S(O)2NH2, —CH2SCH3, —CH2S(O)CH3, —CH2S(O)2CH3, —C(CH3)2SCH3, —C(CH3)2S(O)CH3 or —C(CH3)2S(OCH3 radicals;
• R2 represents an alkyl of 1-5 carbon atoms, an aralkyl of 1-3 alkyl carbon atoms, an alkylthioalkyl of 1-3 alkyl carbon atoms, an arylthioalkyl of 1-3 alkyl carbon atoms, a cycloalkylalkyl of 1-3 alkyl carbon atoms and 3-6 ring member carbon atoms;
• R3 represents an alkyl of 1-5 carbon atoms, a cycloalkyl of 5-8 rmg members or a cycloalkylmethyl radical of 3-6 ring members;
• R4 represents an aryl bonded to the sulfur atom through a carbon atom, a benzo fused 5 to 6 ring member heteroaryl bonded to the sulfur atom through a carbon atom;
• a benzo fused 5 to 6 ring member heterocyclo bonded to the sulfur atom through a carbon atom;
• a radical of the formula:
• wheren A and B each independently represent O, S, SO or SO2;
• R6 represents deuterium, an alkyl of 1-5 carbon atoms, fluoro or chloro;
• R7 represents hydrogen, deuterium, methyl, fluoro or chloro;
• or a radical of the formula
• wherein Z represents O, S or NH;
• and R9 represents a radical of formula
• wherein Y represents O, S or NH;
• X represents a bond, O or NR21;
• R20 represents hydrogen, an alkyl of 1 to 5 carbon atoms, an alkenyl of 2 to 5 carbon atoms, an alkynyl of 2 to 5 carbon atoms, an aralkyl of 1 to 5 alkyl carbon atoms, a heteroaralkyl of 5 to 6 ring members and 1 to 5 alkyl carbon atoms, a heterocycloalkyl of 5 to 6 ring members and 1 to 5 alkyl carbon atoms, an aminoalkyl of 2 to 5 carbon atoms, an N-mono- substituted or N, N-disubstituted aninoalkyl of 2 to 5 alkyl carbon atoms wherein said substituents are selected from radicals of an alkyl of 1 to 3 carbon atoms, an aralkyl of 1 to 3 alkyl carbon atoms, a carboxyalkyl of 1 to 5 carbon atoms, an alkoxycarbonylalkyl of 1 to 5 alkyl carbon atoms, a cyanoalkyl of 1 to 5 carbon atoms and a hydroxyalkyl of 2 to 5 carbon atoms;
• R21 represents hydrogen;
• or an alkyl of 1 to 3 carbon atoms;
• or the radical of formula —NR20R21 represents a 5 to 6 ring member heterocyclo radical;
• and
• R22 represents an alkyl of 1 to 3 carbon atoms or a R20R21N-alkyl of 1 to 3 alkyl carbon atoms;
• R10 represents hydrogen;
• alkyl hydroxyalkyi or alkoxyalkyl radicals, wherein alkyl is 1-3 carbon atoms;
• R11 represents hydrogen, alkyl of 1-5 carbon atoms, hydroxyalkyl of 1-4 carbon atoms, alkoxyalkyl of 1-3 alkyl carbon atoms, benzyl, imidazolylmethyl, —CH2CH2CONH2, —CH2CONH2, —CH2CH2SCH3, or —CH2SCH3 radicals or the sulfone or sulfoxide derivatives thereof:
• R12 represents hydrogen, hydroxyalkyl or alkoxyalkyl radicals, wherein alkyl is 1-3 carbon atoms;
• and
• R13 and R14 each independently represent hydrogen, hydroxy, alkoxy, 2-hydroxyethoxy, hydroxyalkyl or alkoxyalkyl radicals, wherein alkyl is 1-3 carbon atoms;
• or R12 and R13 or R13 and R14 along with the carbon atoms to which they are attached represent 5-6 ring membered heteroaryl or benzo radical, each of which is optionally substituted with at least one hydroxy or alkoxy radical of 1-3 carbon atoms.

Compound represented by the formula:

• or a pharmaceutically acceptable salt, prodrug or ester thereof, wherein
• R1 represents an alkyl of 1-5 carbon atoms, an alkenyl of 2-5 carbon atoms, an alkynyl of 2-5 carbon atoms, a hydroxyalkyl of 1-3 carbon atoms, an alkoxyalkyl of 1-3 alkyl and 1-3 alkoxy carbon atoms, a cyanoalkyl of 1-3 alkyl carbon atoms, inidazolylmethyl —CH2CONH2, —CH2CH2CONH2, —CH2S(O)2NH2, —CH2SCH3, —CH2S(O)CH3, —CH2S(O)2CH3, —C(CH3)2SCH3, —C(CH3)2S(O)CH3 or —C(CH3)2S(O)2CH3 radicals;
• R2 represents an alkyl of 1-5 carbon atoms, an aralkyl of 1-3 alkyl carbon atoms, an alkylthioalkyl of 1-3 alkyl carbon atoms, an arylthioalkyl of 1-3 alkyl carbon atoms, a cycloalkylalkyl of 1-3 alkyl carbon atoms and 3-6 ring member carbon atoms;
• R3 represents an alkyl of 1-5 carbon atoms, a cycloalkyl of 5-8 ring members or a cycloalkylmethyl radical of 3-6 ring members;
• R4 represets a benzo fused 5 to 6 ring member heteroaryl bonded to the sulfur atom through a carbon atom;
• a benzo fused 5 to 6 ring member heterocyclo bonded to the sulfur atom through a carbon atom;
• a radical of the formula:
• wherein A and B each independently represent O, S, SO or SO2;
• R6 represents deuterium, an alkyl of 1-5 carbon atoms, fluoro or chloro;
• R7 represents hydrogen, deuterium, methyl, fluoro or chloro;
• or a radical of the formula
• wherein Z represents O, S or NH;
• and R9 represents a radical of formula
• wherein Y represents O, S or NH;
• X represents a bond, O or NR21;
• R20 represents hydrogen, an alkyl of 1 to 5 carbon atoms, an alkenyl of 2 to 5 carbon atoms, an alkynyl of 2 to 5 carbon atoms, an aralkyl of 1 to 5 alkyl carbon atoms, a heteroaralkyl of 5 to 6 ring members and 1 to 5 alkyl carbon atoms, a heterocycloalkyl of 5 to 6 ring members and 1 to 5 alkyl carbon atoms, an aminoalkyl of 2 to 5 carbon atoms, an N-mono- substituted or N, N-disubstituted aminoalkyl of 2 to 5 alkyl carbon atoms wherein said substituents are selected from radicals of an alkyl of 1 to 3 carbon atoms, an aralkyl of 1 to 3 alkyl carbon atoms, a carboxyalkyl of 1 to 5 carbon atoms, an alkoxycarbonylalkyl of 1 to 5 alkyl carbon atoms, a cyanoalkyl of 1 to 5 carbon atoms and a hydroxyalkyl of 2 to 5 carbon atoms;
• R21 represents hydrogen;
• or an alkyl of 1 to 3 carbon atoms;
• or the radical of formula —NR20R21 represents a 5 to 6 ring member heterocyclo radical;
• and
• R22 represents an alkyl of 1 to 3 carbon atoms or a R20R21N-alkyl of 1 to 3 alkyl carbon atoms;
• R10 represents hydrogen;
• alkyl hydroxyalkyl or alkoxyalkyl radicals, wherein alkyl is 1-3 carbon atoms;
• R11 represents hydrogen, alkyl of 1-5 carbon atoms, hydroxyalkyl of 1-4 carbon atoms, alkoxyalkyl of 1-3 alkyl carbon atoms, benzyl, imidazolylmethyl, —CH2CH2CONH2, —CH2CONH2, —CH2CH2SCH3, or —CH2SCH3 radicals or the sulfone or sulfoxide derivatives thereof:
• R12 represents hydrogen, hydroxyalkyl or alkoxyalkyl radicals, wherein alkyl is 1-3 carbon atoms, and
• R13 and R14 each independently represent hydrogen, hydroxy, alkoxy, 2-hydroxyethoxy, hydroxyalkyl or alkoxyalkyl radicals, wherein alkyl is 1-3 carbon atoms;
• or R12 and R13 or R13 and R14 along with the carbon atoms to which they are attached represent 5-6 ring membered heteroaryl or benzo radical, each of which is optionally substituted with at least one hydroxy or alkoxy radical of 1-3 carbon atoms.