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US 11,230,550 B2Granted
Macrocyclic HIV-1 protease inhibitors and uses thereof
AssigneePurdue Research Foundation
InventorsArun K. Ghosh, Hiroaki Mitsuya, Sean Fyvie, Margherita Brindisi
Life of this patent
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Abstract
Described herein are compounds of the formulae (I), (Ia), (Ib), and (II) and pharmaceutically acceptable salts, isomers, mixture of isomers, crystalline forms, non-crystalline forms, hydrates, or solvates thereof, as well as methods of making and using compounds of the formulae (I), (Ia), (Ib), and (II) to, among other things, treat HIV/AIDS.
Claims20
A compound of the formula (I):
- or a pharmaceutically acceptable salt, stereoisomer, crystalline form, non-crystalline form, hydrate, or solvate thereof wherein:
- the dashed line represents an E- or Z-double bond;
- Z1 is:
- R1 and R2 are each independently hydrogen, alkyl or arylalkyl;
- R3 and R4 are each independently H, alkyl or R3 and R4, together with the carbon atom to which they are attached, form a cycloalkyl or a heterocyclyl group;
- Y1 is —CH2—;
- X1 and X2 are each independently oxygen, SO2, optionally substituted nitrogen, or optionally substituted alkylene;
- each R5 is independently hydrogen —SO2R7, —NR27, —CHR7OR7 or —CR37, wherein each R7 is independently hydrogen, heteroalkyl or heterocyclyl or two adjacent R5 groups, together with the carbon atoms to which they are attached, form a heteroaryl group;
- each R6 is independently hydrogen, halo, —NR27, alkyl, aryl, alkylaryl, heteroalkyl or heterocyclyl;
- y is an integer from 1 to 3;
- p is an integer from 1 to 3, and
- n is an integer from 0 to 4.
9 more elements
A compound of the formula (II):
- or a pharmaceutically acceptable salt, stereoisomer, crystalline form, non-crystalline form, hydrate, or solvate thereof wherein:
- the dashed line represents an E- or Z-double bond;
- Z2 is:
- wherein R8 is —OR9 or —NR29, wherein each R9 is independently hydrogen, alkyl, heteroalkyl or heterocyclyl;
- R1 and R2 are each independently hydrogen, alkyl or arylalkyl;
- R3 and R4 are each independently H, alkyl or R3 and R4, together with the carbon atom to which they are attached, form a cycloalkyl or a heterocyclyl group;
- X1 and X2 are each independently oxygen, SO2, optionally substituted nitrogen, or optionally substituted alkylene;
- each R5 is independently hydrogen, —SO2R7, —NR27, —CHR7OR7 or CR37, wherein each R7 is independently hydrogen, heteroalkyl or heterocyclyl or two adjacent R5 groups, together with the carbon atoms to which they are attached, form a heteroaryl group;
- each R6 is independently hydrogen, halo, —NR27, alkyl, aryl, alkylaryl, heteroalkyl or heterocyclyl;
- y is an integer from 1 to 3;
- p is an integer from 1 to 3;
- and
- n is an integer from 0 to 4.
10 more elements
A compound of the formula:
- or a pharmaceutically acceptable salt, crystalline form, non-crystalline form, hydrate, or solvate thereof.
A compound of the formula (I):
- or a pharmaceutically acceptable salt, stereoisomer, crystalline form, non-crystalline form, hydrate, or solvate thereof wherein:
- the dashed line represents an E- or Z-double bond;
- Z1 is:
- R1 and R2 are each independently hydrogen, alkyl or arylalkyl;
- R3 and R4 are each independently H, alkyl or R3 and R4, together with the carbon atom to which they are attached, form a cycloalkyl or a heterocyclyl group;
- X1 and X2 are each independently oxygen, S, S(O), SO2, optionally substituted nitrogen, or optionally substituted alkylene;
- each R5 is independently hydrogen, —ORb, wherein Rb is alkyl or aryl, —SO2R7, R27, —CHR7OR7 or CR37, wherein each R7 is independently hydrogen, alkyl, heteroalkyl or heterocyclyl or two adjacent R5 groups, together with the carbon atoms to which they are attached, form a heteroaryl group;
- each R6 is independently hydrogen, halo, —NR72, alkyl, aryl, alkylaryl, heteroalkyl or heterocyclyl;
- y is an integer from 1 to 3;
- p is an integer from 1 to 3;
- and
- n is an integer from 0 to 4.
9 more elements
A compound of the formula:
- or a pharmaceutically acceptable salt, crystalline form, non-crystalline form, hydrate, or solvate thereof.
Dependencies are inferred from the claim text.