HIV protease inhibitors, compositions containing the same, their pharmaceutical uses, material for their synthesis
AssigneePfizer Inc.
InventorsDavid John Kucera, Robert William Scott
Life of this patent
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Abstract
Compounds of the formula: 1 where the formula variables are as defined herein, are disclosed that advantageously inhibit or block the biological activity of the HIV protease. These compounds, as well as pharmaceutical compositions containing these compounds, are useful for treating patients or hosts infected with the HIV virus. Intermediates and synthetic methods for preparing such compounds are also described.
Claims18
A process for preparing a compound of formula (I-A), or a prodrug, pharmaceutically active metabolite, or pharmaceutically active salt or solvate thereof,
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- wherein:
- R1 is a 5- or 6-membered mono-cyclic carbocyclic or heterocyclic group, wherein said carbocyclic or heterocyclic group is saturated, partially unsaturated or fully unsaturated and is optionally substituted by at least one substituent chosen from C1-6 alkyl, hydroxyl, C1-6 alkylcarbonyloxy, C6-10 arylcarbonyloxy, and heteroarylcarbonyloxy;
- R2 is C2-6 alkenyl or C1-6 alkyl optionally substituted with at least one halogen;
- R2′ is H or C1-4 alkyl;
- Z is S, O, SO, SO2, CH2 or CFH;
- R3 is H or C1-C4 alkyl;
- and
- R4, R5, R6 and R7 are independently chosen from H and C1-C6 alkyl;
- prepared by:
- reacting a compound of formula (II), wherein Y1 is hydroxyl or a leaving group, with a compound of formula (III), or a salt or solvate thereof,
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A process for preparing a compound of formula (I-B),
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- comprising:
- reacting a compound of formula (II-A) with a compound of formula (III-A), or a salt or solvate thereof,
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A process for preparing a compound of formula (I-C),
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- comprising:
- (i) reacting a compound of formula (II-A) with a compound of formula (III-A), or a salt or solvate thereof,
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- to afford a compound of formula (I-B);
- and
- (ii) deprotecting the compound of formula (I-B).
A process for preparing a compound of formula (I-C),
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- comprising:
- reacting a compound of formula (II-B) with a compound of formula (III-A), or a salt or solvate thereof,
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A process for preparing a compound of formula (I-C),
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- comprising:
- (i) reacting a compound of formula (IV-A) with a compound of formula (V-A),
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- to afford a compound of formula (II-A);
- (ii) reacting the compound of formula (II-A) with a compound of formula (III-A), or a salt or solvate thereof,
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- to afford a compound of formula (I-B);
- and
- (iii) deprotecting the compound of formula (I-B).
Dependencies are inferred from the claim text.