C-3 cycloalkenyl triterpenoids with hiv maturation inhibitory activity

A compound, including pharmaceutically acceptable salts thereof, which is selected from the group consisting of:

• a compound of formula I
• a compound of formula II
• a compound of formula III
• and a compound of formula IV
• wherein R1 is isopropenyl or isopropyl;
• J and E are independently —H or —CH3, and E is absent when the double bond is present;
• X is selected from the group of C4-8 cycloalkyl, C4-8 cycloalkenyl, C4-9 spirocycloalkyl, C4-9 spirocycloalkenyl, C4-8 oxacycloalkyl, C4-8 dioxacycloalkyl, C6-8 oxacycloalkenyl, C6-8 dioxacycloalkenyl, C6 cyclodialkenyl, C6 oxacyclodialkenyl, C6-9 oxaspirocycloalkyl and C6-9 oxaspirocycloalkenyl ring, wherein X is substituted with A, wherein A is at least one member selected from the group of —H, -halo, -hydroxyl, —C1-6 alkyl, —C1-6 alkoxy, C1-6 alkyl-Q, -alkylsubstituted C1-6 alkyl-Q, —CN, —CF2Q, —NR8R9, —COOR2 and —CONR2R2,
• X can also be selected from the group of:
• wherein Q is selected from the group of aryl, heteroaryl, substituted heteroaryl, —OR2, —COOR3, —NR2R2, —SO2R7, —CONHSO2R3, and —CONHSO2NR2R2;
• R2 is —H, —C1-6 alkyl, -alkylsubstituted C1-6 alkyl or -arylsubstituted C1-6 alkyl;
• Y is selected from the group of —COOR2, —C(O)NR2SO2R3, —C(O)NHSO2NR2R2, —NR2SO2R2, —SO2NR2R2, —C3-6 cycloalkyl-COOR2, —C2-6 alkenyl-COOR2, —C2-6 alkynyl-COOR2, —C1-6 alkyl-COOR2, -alkylsubstituted C1-6 alkyl, —COOR2, CF2—COOR2, —NHC(O)(CH2)n—COOR2, —SO2NR2C(O)R2, _tetrazole, and —CONHOH,
• wherein n=1-6;
• W is absent, CH2 or CO;
• R3 is —C1-6 alkyl or -alkylsubstituted C1-6 alkyl;
• R4 is selected from the group of —H, —C1-6 alkyl, —C1-6alkyl-C(OR3)2—C3-6cycloalkyl, —C1-6 substituted alkyl, —C1-6 alkyl-C3-6 cycloalkyl, —C1-6 alkyl-Q1, —C1-6 alkyl-C3-6 cycloalkyl-Q1, aryl, heteroaryl, substituted heteroaryl, —COR6, —COCOR6, —SO2R7, —SO2NR2R2,
• with the proviso that R4 or R5 cannot be COR6 or COCOR6 when W is CO;
• wherein Q1 is selected from the group of heteroaryl, substituted heteroaryl, halogen, —CF3, —OR2, —COOR2, —NR8R9, —CONR10R11 and —SO2R7;
• R5 is selected from the group of —H, —C1-6 alkyl, —C3-6 cycloalkyl, —C1-6 alkylsubstituted alkyl, —C1-6alkyl-NR8R9, —COR10, —COR6, —COCOR6, —SO2R7 and —SO2NR2R2;
• with the proviso that only one of R4 or R5 can be selected from the group of —COR6, —COCOR6, —SO2R7 and —SO2NR2R2;
• or when W is absent or is CH2, then R4 and R5 can be taken together with the adjacent N to form
• R6 is selected from the group of —H, —C1-6 alkyl, —C1-6 alkyl-substitutedalkyl, —C3-6 cycloalkyl, —C3-6 substitutedcycloalkyl-Q2, —C1-6 alkyl-Q2, —C1-6 alkyl-substitutedalkyl-Q2, —C3-6 cycloalkyl-Q2, aryl-Q2, —NR13R14, and —OR15;
• wherein Q2 is selected from the group of aryl, heteroaryl, substituted heteroaryl, —OR2, —COOR2, —NR8R9, SO2R7, —CONHSO2R3, and —CONHSO2NR2R2;
• R7 is selected from the group of —C1-6 alkyl, —C1-6 substituted alkyl, —C3-6 cycloalkyl, —CF3, aryl, and heteroaryl;
• R8 and R9 are independently selected from the group of —H, —C1-6 alkyl, —C1-6 substituted alkyl, aryl, heteroaryl, substituted aryl, substituted heteroaryl, —C1-6 alkyl-Q2, and —COOR3,
• and R8 and R9 can also be independently selected from the group of
• or R8 and R9 are taken together with the adjacent N to form a cycle selected from the group of:
• with the proviso that only one of R8 or R9 can be —COOR3;
• R10 and R11 are independently selected from the group of —H, —C1-6 alkyl, —C1-6 substituted alkyl and —C3-6 cycloalkyl,
• or R10 and R11 are taken together with the adjacent N to form a cycle such as
• R12 is selected from the group of —C1-6 alkyl, —C1-6 alkyl-OH;
• —C1-6 alkyl, —C1-6 substituted alkyl, —C3-6 cycloalkyl, —COR7, —COONR22R23, —SOR7, and —SONR24R25;
• R13 and R14 are independently selected from the group of —H, —C1-6 alkyl, —C3-6 cycloalkyl, —C1-6 substituted alkyl, —C1-6 alkyl-Q3, —C1-6 alkyl-C3-6 cycloalkyl-Q3, C1-6 substituted alkyl-Q3 and
• or R13 and R14 are taken together with the adjacent N to form a cycle selected from the group of:
• Q3 is selected from the group of heteroaryl, substituted heteroaryl, —NR20R21, −CONR2R2, —COOR2, —OR2, and —SO2R3;
• R15 is selected from the group of —C1-6 alkyl, —C3-6 cycloalkyl, —C1-6 substituted alkyl, —C1-6 alkyl-Q3, —C1-6 alkyl-C3-6 cycloalkyl-Q3 and —C1-6 substituted alkyl-Q3,
• R16 is selected from the group of —H, —C1-6 alkyl, —NR2R2, and —COOR3;
• R17 is selected from the group of —H, —C1-6 alkyl, —COOR3, and aryl;
• R18 is selected from the group of —COOR2 and —C1-6 alkyl-COOR2;
• R19 is selected from the group of —H, —C1-6 alkyl, —C1-6 alkyl-Q4, —COR3, —COOR3,
• wherein Q4 is selected from the group of —NR2R2 and —OR2;
• R20 and R21 are independently selected from the group of —H, —C1-6 alkyl, —C1-6 substituted alkyl, —C1-6 substituted alkyl-OR2, and —COR3,
• or R20 and R21 are taken together with the adjacent N to form a cycle selected from the group of
• with the proviso that only one of R20 or R21 can be —COR3,
• R22 and R23 are independently selected from the group of H, —C1-6 alkyl, —C1-6 substituted alkyl, and —C1-6 cycloalkyl,
• or R22 and R23 are taken together with the adjacent N to form a cycle selected from the group of
• R24 and R25 are independently from the group of H, —C1-6 alkyl, —C1-6 substituted alkyl, —C1-6 alkyl-Q5, —C1-6 cycloalkyl, aryl, substituted aryl, heteroaryl, and substituted heteroaryl, and Q5 is selected from the group of halogen and SO2R3.