US2014206684A1PendingUtilityA1
Certain chemical entities, compositions and methods
Est. expiryJan 4, 2028(~1.5 yrs left)· nominal 20-yr term from priority
A61P 37/08A61P 5/14A61P 9/00A61P 9/10A61P 37/06A61P 37/02A61P 43/00A61P 37/00A61P 7/06A61P 7/02A61P 3/10A61P 29/00A61P 35/00A61P 35/02A61P 27/02A61P 25/00A61P 3/00A61P 27/16A61P 31/12A61P 31/00A61P 31/04A61P 11/00A61P 1/14A61P 19/00A61P 17/06A61P 17/00A61P 17/04A61P 15/14A61P 21/04A61P 1/02A61P 17/02A61P 1/04A61P 1/16A61P 13/12A61P 13/10A61P 15/00A61P 13/00A61P 19/02A61P 19/08A61P 13/08A61P 1/00A61P 15/08A61P 1/18A61P 11/06A61P 11/02A61P 11/16C07D 487/04C07D 513/04C07D 473/34C07D 519/00C07D 495/04A61K 31/52C07D 471/04A61K 45/06A61K 31/675A61K 31/519A61K 31/5377C07F 9/6561C07D 473/04Y02A50/30
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Claims
Abstract
Chemical entities that modulate PI3 kinase activity, and chemical entities, pharmaceutical compositions, and methods of treatments of diseases and conditions associated with P13 kinase activity are described herein.
Claims
exact text as granted — not AI-modified1 - 59 . (canceled)
60 . A compound of Formula I:
or a pharmaceutically acceptable salt thereof, wherein:
W a 1 is CR 3 ;
W a 2 is CR 5 ;
W a 3 is CR 6 ;
W a 4 is N;
W b 5 is CR 8 , CHR 8 , or N;
W d is
R a is hydrogen, halo, phosphate, urea, carbonate, alkyl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, or heterocycloalkyl;
R 11 is hydrogen, alkyl, halo, amino, amido, hydroxy, or alkoxy;
R 12 is hydrogen, alkyl, cyano, alkynyl, alkenyl, halo, aryl, heteroaryl, heterocycloalkyl, cycloalkyl, amino, carboxylic acid, alkoxycarbonyl, or amido;
B is alkyl, amino, heteroalkyl, cycloalkyl, heterocycloalkyl, or a moiety of Formula II:
W c is aryl, heteroaryl, heterocycloalkyl, or cycloalkyl;
q is an integer of 0, 1, 2, 3, or 4;
X is absent or is —(CH(R 9 )) z — and each instance of z is independently an integer of 1, 2, 3, or 4;
Y is absent, —O—, —S—, —S(═O)—, —S(═O) 2 —, —N(R 9 )—, —C(═O)(CHR 9 ) z —, —C(═O)—, —N(R 9 )C(═O)NH—, or —N(R 9 )C(R 9 ) 2 —, wherein when W b 5 is N, no more than one of X or Y is absent;
R 1 is hydrogen, alkyl, heteroalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxy, nitro, phosphate, urea, or carbonate;
R 2 is alkyl, heteroalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxy or nitro;
R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamide, halo, cyano, hydroxyl, nitro, aryl, or heteroaryl;
R 5 , R 6 , and R 8 are independently hydrogen, C 1 -C 4 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, C 1 -C 4 heteroalkyl, C 1 -C 4 alkoxy, C 1 -C 4 amido, amino, acyl, C 1 -C 4 acyloxy, C 1 -C 4 sulfonamido, halo, cyano, hydroxy or nitro; and
each instance of R 9 is independently hydrogen, C 1 -C 10 alkyl, C 3 -C 7 cycloalkyl, or C 2 -C 10 heteroalkyl.
61 . The compound of claim 60 , wherein the compound is a compound of Formula VIII-A:
or a pharmaceutically acceptable salt thereof.
62 . The compound of claim 60 , wherein the compound is a compound of Formula VII:
or a pharmaceutically acceptable salt thereof.
63 . The compound of claim 60 , wherein W c is aryl or heterocycloalkyl.
64 . The compound of claim 60 , wherein R 3 is alkyl.
65 . The compound of claim 60 , wherein R 5 , R 6 , and R 8 are hydrogen.
66 . The compound of claim 60 , wherein X is —(CH(R 9 )) z — and z is an integer of 1.
67 . The compound of claim 60 , wherein Y is absent.
68 . The compound of claim 60 , wherein R 12 is iodo, bromo,
69 . The compound of claim 60 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
70 . The compound of claim 60 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
71 . The compound of claim 60 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
72 . A compound of Formula 6-A:
or a pharmaceutically acceptable salt thereof, wherein:
R 12 is hydrogen, alkyl, cyano, alkynyl, alkenyl, halo, aryl, heteroaryl, heterocycloalkyl, cycloalkyl, amino, carboxylic acid, alkoxycarbonyl, or amido;
B is alkyl, amino, heteroalkyl, cycloalkyl, heterocycloalkyl, or a moiety of Formula II:
W c is aryl, heteroaryl, heterocycloalkyl, or cycloalkyl;
q is an integer of 0, 1, 2, 3, or 4;
R 1 is hydrogen, alkyl, heteroalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxy, nitro, phosphate, urea, or carbonate;
R 2 is alkyl, heteroalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxy or nitro; and
R 3 is hydrogen or alkyl.
73 . The compound of claim 72 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
74 . A compound of Formula IX:
or a pharmaceutically acceptable salt thereof.
W a 1 and W a 2 are independently CR 5 , S, N, or NR 4 ,
W a 4 is independently CR 7 , S, N, or NR 4 ;
wherein no more than two adjacent ring atoms are nitrogen or sulfur, and when W a 1 is S, one of W a 2 and W a 4 is N or NR 4 ;
W b 5 is CR 8 , N, or NR 8 ;
B is alkyl, amino, heteroalkyl, cycloalkyl, heterocycloalkyl, or a moiety of Formula II;
W c is aryl, heteroaryl, heterocycloalkyl, or cycloalkyl;
q is an integer of 0, 1, 2, 3, or 4;
W d is a heterocycloalkyl, aryl or heteroaryl moiety;
X is —(CH(R 9 )) z —;
each instance of z independently is an integer of 1;
Y is absent;
R 1 is hydrogen, alkyl, heteroalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxy or nitro;
R 2 is alkyl, heteroalkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkoxy, amido, amino, acyl, acyloxy, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxy, nitro, phosphate, urea, or carbonate;
R 4 is hydrogen, acyl, C 1 -C 4 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, or C 1 -C 4 heteroalkyl;
R 5 , R 7 , and R 8 are independently hydrogen, C 1 -C 4 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 5 cycloalkyl, C 1 -C 4 heteroalkyl, acyl, C 1 -C 4 alkoxy, C 1 -C 4 amido, amino, C 1 -C 4 acyloxy, C 1 -C 4 sulfonamido, halo, cyano, hydroxy or nitro; and
each instance of R 9 is independently hydrogen, C 1 -C 10 alkyl, C 3 -C 7 cycloalkyl, or C 2 -C 10 heteroalkyl.
75 . The compound of claim 74 , wherein the compound is a compound of Formula XIII or Formula X:
or a pharmaceutically acceptable salt thereof, wherein
B is a moiety of Formula II;
wherein W c is aryl, heteroaryl, heterocycloalkyl, or cycloalkyl, and
q is an integer of 0, 1, or 2;
W d is:
X is (CH 2 ) z ;
Y is absent;
z is 1;
R 1 is hydrogen, fluoro, chloro, cyano, methyl, isopropyl, —CF 3 , methoxy, or nitro;
R 2 is halo, hydroxy, cyano, or nitro;
R 4 is hydrogen or methyl;
R 5 is hydrogen or methyl;
R 7 is hydrogen or methyl;
R 11 is amino; and
R 12 is hydrogen, alkyl, alkynyl, alkenyl, halo, aryl, heteroaryl, heterocycloalkyl, or cycloalkyl.
76 . The compound of claim 74 , wherein R 12 is iodo, bromo,
77 . The compound of claim 74 , wherein the compound is:
or a pharmaceutically acceptable salt thereof.
78 . A pharmaceutical composition comprising a compound of claim 60 , or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable excipients.
79 . A pharmaceutical composition comprising a compound of claim 74 , or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable excipients.
80 . A method of treating a disorder comprising administering an effective amount of a compound of claim 60 to a subject suffering from the disorder, wherein the disorder is selected from cancer, bone disorder, inflammatory disease, immune disease, nervous system disease, metabolic disease, respiratory disease, thrombosis, and cardiac disease.
81 . A method of treating a disorder comprising administering an effective amount of a compound of claim 74 to a subject suffering from the disorder, wherein the disorder is selected from cancer, bone disorder, inflammatory disease, immune disease, nervous system disease, metabolic disease, respiratory disease, thrombosis, and cardiac disease.Cited by (0)
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