US 6,673,791 B2Granted

Non-nucleoside reverse transcriptase inhibitors

AssigneeBoehringer Ingelheim (Canada) Ltd.

InventorsWilliam W. Ogilvie, Robert Déziel, Jeffrey O'Meara, Bruno Simoneau

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Abstract

Compounds represented by formula I: wherein R2 is H, halogen, NHNH2, (C1-4)alkyl, O(C1-6)alkyl, and haloalkyl; R4 is H or Me; R5 is H or (C1-4)alkyl; R11 is (C1-4)alkyl, (C1-4)alkyl(C3-7)cycloalkyl, or (C3-7)cycloalkyl; and Q is naphthyl, fused phenyl(C4-7)cycloalkyl and fused phenyl-5, 6, or 7-membered saturated heterocycle having one to two heteroatom selected from O, N, or S, said Q being substituted with from 1 to 4 R12 substituents selected from: R13, (C1-6)alkyl, (C3-7)cycloalkyl, or (C2-6)alkenyl, said alkyl, cycloalkyl, or alkenyl being optionally substituted with R13; or a salt thereof. Compounds represented by formula I have inhibitory activity against Wild Type, single and double mutant strains of HIV.

A compound represented by formula I:

wherein
R2 is selected from the group consisting of H, halogen, NHNH2, (C1-4alkyl, O(C1-6)alkyl, and haloalkyl;
R4 is H or Me;
R5 is H or (C1-4alkyl;
R11 is (C1-4alkyl, (C1-4alkyl(C3-7)cycloalkyl, or (C3-7)cycloalkyl;
and
Q is naphthyl, fused phenyl(C47)cycloalkyl and fused phenyl-5, 6, or 7-membered saturated heterocycle having one N atom said Q being substituted with from 1 to 4-substituents each designated R12 wherein each substituent designated R12 has either the same definition as the group R13 or is selected from the group consisting of (C1-6)alkyl, (C3-7)cycloalkyl, or (C2-6)alkenyl, said alkyl, cycloalkyl, or alkenyl being optionally substituted with R13,
wherein R13 defined as:
a) NR13aCOR13b wherein R13a and R13b are each in dependently H, (C1-6)alkyl, (C3-7)cycloalkyl or (C1-6)alkyl-(C3-7)cycloalkyl, said alkyl, cycloalkyl or alkyl-cycloalkyl being optionally substituted with R14;
b) NR13cSO2R13d wherein R13c is H, (C1-6)alkyl, (C3-7)cycloalkyl or (C1-6)alkyl-(C3-7)cycloalkyl and R13d is (C1-6)alkyl, haloalkyl, (C3-7)cycloalkyl or (C1-6)alkyl-(C3-7)cycloalkyl, said alkyl, cycloalkyl or alkyl-cycloalkyl being optionally substituted with R14;
c) COR13e wherein R13e has the same definition as R13d;
d) COOR wherein R13f has the same definition as R13c;
e) CONR13gR13h wherein R13g and R13h are both independently H, (C1-6)alkyl, (C3-7)cycloalkyl, or (C1-6)alkyl-(C3-7)cycloalkyl;
or both R13g and R13h are covalently bonded together and to the nitrogen to which they are both bonded to form a 5, 6, or 7-membered saturated heterocycle;
or R13h is N(R13i)2 wherein each R13i is independently H, (C1-6)alkyl, (C3-7)cycloalkyl, or (C1-6)alkyl-(C3-7)cycloalkyl or both R13i are covalently bonded together and to the nitrogen to which they are both bonded to form a 5, 6, or 7-membered saturated heterocycle, said alkyl, cycloalkyl, alkyl-cycloalkyl or heterocycle being optionally substituted with R14;
f) CONR13jSO2R13k wherein R13j has the same definition as R13c and R13k has the same definition as R13d;
or
g) SO2R13l wherein R13l is (C1-6)alkyl, (C3-7)cycloalkyl, or (C1-6)alkyl-(C3-7)cycloalkyl;
or R13l is NR13mR13n wherein R13m and R13n are both independently H, (C1-6)alkyl, (C3-7)cycloalkyl, or (C1-6)alkyl-(C3-7)cycloalkyl;
or both R13m and R13n are covalently bonded together and to the nitrogen to which they are both bonded to form a 5, 6, or 7-membered saturated heterocycle, said alkyl, cycloalkyl, alkyl-cycloalkyl or heterocycle being optionally substituted with R14;
wherein R14 is defined as:
COOR14a, or CON(R14b)2 wherein R14a and R14b are both independently H, (C1-6)alkyl, (C3-7)cycloalkyl, or (C1-6)alkyl-(C3-7)cycloalkyl;
or both R14b are covalently bonded together and to the nitrogen to which they are both bonded to form a 5, 6, or 7-membered saturated heterocycle;
or a salt thereof.

21 more elements

Abstract

Claims40