Substituted 6-benzyl-4-oxopyrimidines, process for their preparation and pharmaceutical compositions containing them
AssigneeIdenix Pharmaceuticals, Inc.
InventorsMarino Artico, Paolo La Colla
Life of this patent
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Abstract
The invention concerns novel substituted 6-benzyl-4-oxopyrimidines and pharmaceutically acceptable salts thereof. These compounds inhibit reverse transcriptase encoded by human immunodeficiency virus (HIV), and are useful to prevent and treat HIV infection and acquired immune deficiency syndrome (AIDS). Pharmaceutical compositions containing the compounds and a method of use of the present compounds and other agents for the treatment of AIDS and viral infection by HIV are also envisaged.
Claims49
A compound of the formula:
- wherein:
- a) X is —NK;
- b) R is —C1-4alkyl optionally substituted by one or more of heteroatoms selected from O, S, and N, —C3-6cycloalkyl optionally substituted by one or more of heteroatoms selected from O, S, and N, -aryl, arylalkyl, or heterocycle;
- c) Y is —H, —C1-4alkyl, or —C3-6cycloalkyl;
- d) Z is —C1-4alkyl, or —C3-6cycloalkyl;
- e) R1 is —H, —C1-4alkyl, halogen, —NO2, —OW, or —SW;
- f) R2 is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- g) R3 is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- h) R4 is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- i) R5 is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- j) K is —H, —C1-4alkyl, or —C3-6cycloalkyl;
- and
- k) W is —H, —CH3, or -aryl;
- or a pharmaceutically acceptable salt thereof.
A compound of the formula:
- wherein:
- a) X is —NK;
- b) R is —C1-4alkyl optionally substituted by one or more of heteroatoms selected from O, S, and N, —C3-6cycloalkyl optionally substituted by one or more of heteroatoms selected from O, S, and N, -aryl, arylalkyl, or heterocycle;
- c) Y is —C1-4alkyl, or —C3-6cycloalkyl;
- d) Z is —H, —C1-4alkyl, or —C3-6cycloalkyl;
- e) R1 is —H, —C1-4alkyl, halogen, —NO2, —OW, or —SW;
- f) R2 is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- g) R3 is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- h) R4is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- i) R5 is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- j) K is —H, —C1-4alkyl, or —C3-6cycloalkyl;
- and
- k) W is —H, —CH3, or -aryl;
- or a pharmaceutically acceptable salt thereof.
A compound of the formula:
- wherein:
- a) X is —NK;
- b) R is —C1-4alkyl optionally substituted by one or more of heteroatoms selected from O, S, and N, —C3-6cycloalkyl optionally substituted by one or more of heteroatoms selected from O, S, and N, -aryl, arylalkyl, or heterocycle;
- c) Y is H, —C1-4alkyl, or —C3-6cycloalkyl;
- d) Z is —H, —C1-4alkyl, or —C3-6cycloalkyl;
- e) R1 is —C1-4alkyl, halogen, —NO2, —OW, or —SW;
- f) R2 is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- g) R3 is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- h) R4 is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- i) R5 is —H, —C1-4alkyl, -halogen, —NO2, —OW, or —SW;
- j) K is —H, —C1-4alkyl, or —C3-6cycloalkyl;
- and
- k) W is —H, —CH3, or -aryl;
- or a pharmaceutically acceptable salt thereof.
A compound of the formula:
- wherein:
- X = N Y = CH3 Z = H R = Me-Pip R1 = F R2 = H R3 = H R4 = H R5 = F;
- X = N Y = CH3 Z = H R = Morph R1 = F R2 = H R3 = H R4 = H R5 = F;
- X = N Y = CH3 Z = H R = S-morp R1 = F R2 = H R3 = H R4 = H R5 = F;
- X = N Y = H Z = H R = Me-Pip R1 = F R2 = H R3 = H R4 = H R5 = F;
- X = N Y = H Z = H R = Morph R1 = F R2 = H R3 = H R4 = H R5 = F;
- X = N Y = H Z = H R = S-morp R1 = F R2 = H R3 = H R4 = H R5 = F;
- X = N Y = H Z = H R = Piper R1 = F R2 = H R3 = H R4 = H R5 = F;
- or X = N Y = H Z = H R = Pyrroli R1 = F R2 = H R3 = H R4 = H R5 = F, and
- further wherein Me-Pip is methylpiperidinyl, Morph is morpholinyl, S-morp is thiomorpholinyl, Piper is piperidinyl, and pyrroli is pyrrolidinyl.
2-Cyclopentylamino-6-{1-(2,6-difluorophenyl)ethyl}-3,4-dihydro-5-methylpyrimidin-4-(3H)-one.
Dependencies are inferred from the claim text.