US2010286192A1PendingUtilityA1
Non-nucleoside reverse transcriptase inhibitors
Individually held — no corporate assignee on recordPriority: Dec 13, 2006Filed: Jul 20, 2010Published: Nov 11, 2010
Est. expiryDec 13, 2026(~0.4 yrs left)· nominal 20-yr term from priority
A61P 31/18A61P 43/00C07D 471/04C07D 231/54C07D 249/18A61K 31/4192
44
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Claims
Abstract
Compounds of Formula I: are HIV reverse transcriptase inhibitors, wherein V, W, X, Y, Z, R 1 , R 2 , R 4 , R 5 , R 6 , ring A, ring B, j and k are defined herein. The compounds of Formula I, and the pharmaceutically acceptable salts and prodrugs thereof, are useful in the inhibition of HIV reverse transcriptase, the prophylaxis and treatment of infection by HIV and in the prophylaxis, delay in the onset or progression, and treatment of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.
Claims
exact text as granted — not AI-modified1 .- 24 . (canceled)
25 . A pharmaceutical composition comprising an effective amount of a compound of Formula IXa:
or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier; wherein:
T 1 and T 2 and T 3 are each independently H, C 1-4 alkyl, halogen, CN, CH═CH—CN, C(O)R A , or (CH 2 ) 1-2 N(R A )R B
R 2 and R 3 are each independently selected from the group consisting of:
(1) H,
(2) halogen,
(3) N(R A )R B,
(4) C 1-4 alkyl,
(5) CF 3 ,
(6) O—C 1-4 alkyl, and
(7) OCF 3 ;
L is N or N oxide;
Q is —C(R 4 )═N—, wherein the left-most atom in Q is the atom directly attached to the fused benzo;
R 7 and R 8 are each independently selected from the group consisting of:
(1) H,
(2) OH,
(3) halogen,
(4) CN,
(5) NO 2 ,
(6) C 1-4 alkyl,
(7) O—C 1-4 alkyl,
(8) O(CH 2 ) 2-3 N(R A )R B ,
(9) O(CH 2 ) 1-3 C(O)R A ,
(10) CF 3 ,
(11) OCF 3 ,
(12) O(CH 2 ) 1-2 CF 3 ,
(13) N(R C )R D ,
(14) N(R A )—(CH 2 ) 2-3—N(R C )R D , and
(15) C(O)N(R A )R B ;
each R A is independently H or C 1-4 alkyl;
each R B is independently H or C 1-4 alkyl;
each R C is independently H or C 1-4 alkyl;
each R D is independently H or C 1-4 alkyl; and
alternatively and independently each pair of R C and R D together with the N atom to which they are both attached form a saturated monocyclic ring selected from the group consisting of:
26 . A method for the treatment of HIV-1 infection, wherein the method comprises administering to a subject in need thereof an effective amount of a compound of Formula IXa:
or a pharmaceutically acceptable salt thereof; wherein: T 1 and T 2 and T 3 are each independently H, C 1-4 alkyl, halogen, CN, CH═CH—CN, C(O)R A , or (CH 2 ) 1-2 N(R A )R B ;
R 2 and R 3 are each independently selected from the group consisting of:
(1) H,
(2) halogen,
(3) N(R A )R B ,
(4) C 1-4 alkyl,
(5) CF 3 ,
(6) O—C 1-4 alkyl, and
(7) OCF 3 ;
L is N or N oxide;
Q is —C(R 4 )=N—, wherein the left-most atom in Q is the atom directly attached to the fused benzo;
R 7 and R 8 are each independently selected from the consisting of:
(1) H,
(2) OH,
(3) halogen,
(4) CN,
(5) NO 2 ,
(6) C 1-4 alkyl,
(7) O—C 1-4 alkyl,
(8) O(CH 2 ) 2-3 N(R A )R B ,
(9) O(CH 2 ) 1-3 C(O)R A ,
(10) CF 3 ,
(11) OCF 3 ,
(12) O(CH 2 ) 1-2 CF 3 ,
(13) N(R C )R D ,
(14) N(R A )—(CH 2 ) 2-3 —N(R C )R D , and
(15) C(O)N(R A )R B ;
each R A is independently H or C 1-4 alkyl;
each R B is independently H or C 1-4 alkyl;
each R C is independently H or C 1-4 alkyl;
each R D is independently H or C 1-4 alkyl; and
alternatively and independently each pair of R C and R D together with the N atom to which they are both attached form a saturated monocyclic ring selected from the group consisting of:
27 . A pharmaceutical composition according to claim 25 , wherein the compound, or a pharmaceutically acceptable salt thereof, is a compound of Formula IXc:
wherein:
T 1 i s H or Cl;
T 2 is CN, CH(O), CH 2 NH 2 , or CH 2 N(H)CH 3 ;
R 2 and R 3 are each independently selected from the group consisting of H, Cl, Br, F and C 1-4 alkyl;
R 4 is H, C 1-4 alkyl, Cl, Br, or F; and
R 8 is H, OH, Cl, Br, F, CH 3 , OCH 3 , O(CH 2 ) 2-3 NH 2 , CF 3 , OCF 3 , OCH 2 CF 3 , NH 2 , N(H)CH 3 , N(CH 3 ) 2 , C(O)NH 2 , C(O)N(H)CH 3 , or C(O)N(CH 3 ) 2.
28 . A pharmaceutical composition according to claim 27 , or a pharmaceutically acceptable salt thereof, wherein Q is —CH═N—.
29 . A pharmaceutical composition according to claim 25 , wherein the compound, or a pharmaceutically acceptable salt thereof, is a compound of Formula IXd:
wherein T 1 and T 2 are each independently H, C 1-4 alkyl, halogen, CN, or CH═CH—CN.
30 . A pharmaceutical composition according to claim 29 , wherein the compound, or a pharmaceutically acceptable salt thereof, is a compound of Formula IXe:
wherein:
R 2 and R 3 are each independently selected from the group consisting of H, Cl, Br, F and C 1-4 alkyl;
R 4 is H, C 1-4 alkyl, Cl, Br, or F; and
R 8 is H, OH, Cl, Br, F, CH 3 , OCH 3 , O(CH 2 ) 2-3 NH 2 , CF 3 , OCF 3 , OCH 2 CF 3 , NH 2 , N(H)CH 3 , N(CH 3 ) 2 , C(O)NH 2 , C(O)N(H)CH 3 , or C(O)N(CH 3 ) 2 .
31 . A pharmaceutical composition according to claim 30 , or a pharmaceutically acceptable salt thereof, wherein:
R 2 is Br or Cl; R 3 is H; and R 8 is H or NH 2 .
32 . A pharmaceutical composition according to claim 25 , wherein the compound is selected from the group consisting of:
and pharmaceutically acceptable salts thereof.
33 . A pharmaceutical composition according to claim 32 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
34 . A pharmaceutical composition according to claim 32 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
35 . A pharmaceutical composition according to claim 32 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
36 . A pharmaceutical composition according to claim 32 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
37 . A method according to claim 26 , wherein the compound, or a pharmaceutically acceptable salt thereof, is a compound of Formula IXc:
wherein:
T 1 is H or Cl;
T 2 is CN, CH(O), CH 2 NH 2 , or CH 2 N(H)CH 3 ;
R 2 and R 3 are each independently selected from the group consisting of H, Cl, Br, F and C 1-4 alkyl;
R 4 is H, C 1-4 alkyl, Cl, Br, or F; and
R 8 is H, OH, Cl, Br, F, CH 3 , OCH 3 , O(CH 2 ) 2-3 NH 2 , CF 3 , OCF 3 , OCH 2 CF 3 , NH 2 , N(H)CH 3 , N(CH 3 ) 2 , C(O)N 2 , C(O)N(H)CH 3 , or C(O)N(CH 3 ) 2 .
38 . A method according to claim 37 , or a pharmaceutically acceptable salt thereof, wherein Q is —CH═N—.
39 . A method according to claim 26 , wherein the compound, or a pharmaceutically acceptable salt thereof, is a compound of Formula IXd:
wherein T 1 and T 2 are each independently H, C 1-4 alkyl, halogen, CN, or CH═CH—CN.
40 . A method according to claim 39 , wherein the compound, or a pharmaceutically acceptable salt thereof, is a compound of Formula IXe:
wherein:
R 2 and R 3 are each independently selected from the group consisting of H, Cl, Br, F and C 1-4 alkyl;
R 4 is H, C 1-4 alkyl, Cl, Br, or F; and
R 8 is H, OH, Cl, Br, F, CH 3 , OCH 3 , O(CH 2 ) 2-3 NH 2 , CF 3 , OCF 3 , OCH 2 CF 3 , NH 2 , N(H)CH 3 , N(CH 3 ) 2 , C(O)NH 2 , C(O)N(H)CH 3 , or C(O)N(CH 3 ) 2 .
41 . A method according to claim 40 , or a pharmaceutically acceptable salt thereof, wherein:
R 2 is Br or Cl; R 3 is H; and R 8 is H or NH 2 .
42 . A method according to claim 26 , wherein the compound is selected from the group consisting of:
and pharmaceutically acceptable salts thereof.
43 . A method according to claim 42 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
44 . A method according to claim 42 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
45 . A method according to claim 42 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
46 . A method according to claim 42 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.Join the waitlist — get patent alerts
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