US2016264556A1PendingUtilityA1
Itraconazole analogs and use thereof
Est. expirySep 7, 2031(~5.1 yrs left)· nominal 20-yr term from priority
A61K 31/496A61K 31/506C07D 405/14A61P 35/00
50
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Claims
Abstract
Provided herein are Itraconazole analogs. Also provided herein are methods of inhibition of Hedgehog pathway, vascular endothelial growth factor receptor 2 (VEGFR2) glycosylation, angiogenesis and treatment of disease with Itraconazole analogs.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound of structural Formula (I):
or an optically pure stereoisomer or pharmaceutically acceptable salt thereof, wherein:
X and Y are each independently CH, or N;
A is CR 6 or N;
B is CR 7 or N;
W is CR 8 or N;
V is CR 9 or N;
Z is CR 10 or N;
Q is O or CH 2 ;
each R 2 , R 3 , R 4 , and R 5 are independently chosen from the group consisting of alkoxy, alkyl, amino, halogen, hydroxy, haloalkyl, perhaloalkyl, perhaloalkoxy, nitro, and cyano;
R 6 , R 7 , R 8 , and R 9 are each independently chosen from the group consisting of hydrogen, alkoxy, alkyl, amino, halogen, hydroxy, haloalkyl, perhaloalkyl, perhaloalkoxy, nitro, and cyano;
T is —OR 11 or hydrogen;
R 11 is hydrogen or alkyl;
G is —(CH 2 ) n or G and R 11 may optionally be joined together to form a dioxolane;
R 1 and R 10 are each independently hydrogen or alkyl;
n is an integer between 0 and 2;
p and t are each independently an integer between 0 and 2;
q and m are each independently an integer between 0 and 4;
D is chosen from the group consisting of
U is O or S;
R 12 and R 13 are each independently chosen from the group consisting of hydrogen and alkyl; and
R 14 is chosen from the group consisting of hydrogen, alkyl, arylalkyl, alkoxyalkyl, arylalkoxy, alkynylalkyl, alkenylalkyl, cycloalkyl, cyanoalkyl, cycloalkylalkyl, heteroalkyl, heterocycloalkyl, heteroaryl, heteroarylalkyl, and heterocycloalkylalkyl.
2 . The compound of claim 1 , wherein:
X and Z are N; Y is CH; A is CR 6 ; B is CR 7 ; W is CR 8 ; V is CR 9 ; D is
p, t, and q are each independently 0;
m is 2; and
R 1 , R 6 , R 7 , R 8 , and R 9 are each independently hydrogen.
3 . The compound of claim 2 , wherein the compound is of structural Formula (II):
4 . The compound of claim 3 , wherein Q is CH 2 .
5 . The compound of claim 4 , wherein T is hydrogen.
6 . The compound of claim 4 , wherein:
T is OR 11 ; and R 11 is hydrogen.
7 . The compound of claim 3 , wherein Q is O.
8 . The compound of claim 7 , wherein T is hydrogen.
9 . The compound of claim 7 , wherein:
T is OR11; and R11 is hydrogen.
10 . The compound of claim 2 , wherein the compound is of structural Formula (III):
wherein:
R 14 is chosen from the group consisting of hydrogen, alkyl, arylalkyl, alkoxyalkyl, arylalkoxy, alkynylalkyl, alkenylalkyl, cycloalkyl, cyanoalkyl, cycloalkylalkyl, and heterocycloalkylalkyl.
11 . The compound of claim 1 , wherein the compound is of structural Formula (IV):
12 . The compound of claim 11 , wherein:
m is 2; and each R 2 is independently chlorine.
13 . The compound of claim 12 , wherein R 14 is
14 . The compound of claim 13 , wherein:
W is CR8; and V is CR9.
15 . The compound of claim 14 , wherein p is 0.
16 . The compound of claim 15 , wherein:
each R4 is independently alkyl; and q is 0, 1, or 2.
17 . The compound of claim 16 , wherein:
each R5 is independently halogen; and t is 0, 1, or 2.
18 . The compound of claim 17 , wherein A is CR 6 .
19 . The compound of claim 18 , wherein B is CR 7 .
20 . The compound of claim 18 , wherein B is N.Join the waitlist — get patent alerts
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