US2018170915A1PendingUtilityA1
5-bromo-indirubins
Est. expiryMar 14, 2033(~6.6 yrs left)· nominal 20-yr term from priority
Inventors:Richard JoveSangkil NamDavid HorneJun XieAlexios Leandros SkaltsounisMarina KritsanidaNicolas Gaboriaud-Kolar
C07D 209/48A61K 31/404C07D 403/14A61K 45/06C07D 209/40A61K 31/496C07D 401/14A61K 31/4439A61P 35/00C07D 401/04A61P 35/02A61P 43/00
58
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Claims
Abstract
Disclosed herein inter alia are compositions and methods for treating cancer using 5-Br-indirubin derivatives.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound, or pharmaceutically acceptable salt thereof, having the formula:
wherein
L is a bond or substituted or unsubstituted alkylene;
R 1 is hydrogen, halogen, —CX 1 3 , —OCX 1 3 , —CN, —OH, —NH 2 , —COOH, —C(O)OR 4 , —CONH 2 , —NO 2 , —SH, —NHNH 2 , —NR 2 R 3 , —OR 4 , —SR 4 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl;
X 1 is independently a halogen;
R 2 and R 3 are independently substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, wherein R 2 and R 3 are optionally joined together to form a substituted or unsubstituted heterocycloalkyl or substituted or unsubstituted heteroaryl;
R 4 is substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl;
R 5 and R 6 are independently hydrogen, halogen, —CX 2 3 , —OCX 2 3 , —CN, —OH, —NH 2 , —COOH, —C(O)OR 9 , —CONH 2 , —NO 2 , —SH, —NHNH 2 , —NR 7 R 8 , —OR 9 , —SR 9 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl;
X 2 is independently a halogen;
R 7 and R 8 are independently substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, wherein R 7 and R 8 are optionally joined together to form a substituted or unsubstituted heterocycloalkyl or substituted or unsubstituted heteroaryl; and
R 9 is substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.
2 . The compound of claim 1 , wherein R 5 and R 6 are hydrogen.
3 . The compound of claim 1 , wherein L is unsubstituted alkylene.
4 . The compound of claim 1 , wherein L is unsubstituted C 1 -C 8 alkylene.
5 . The compound of claim 1 , wherein L is unsubstituted C 1 -C 4 alkylene.
6 . The compound of claim 1 , wherein L is unsubstituted C 2 alkylene.
7 . The compound of claim 1 , wherein L is a bond.
8 . The compound of claim 1 , wherein R 1 is halogen, —CX 3 , —OCX 3 , —CN, —OH, —NH 2 , —COOH, —C(O)OR 4 , —CONH 2 , —NO 2 , —SH, —NHNH 2 , —NR 2 R 3 , —OR 4 , —SR 4 , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.
9 . The compound of any claim 1 , wherein R 1 is —NR 2 R 3 .
10 . The compound of claim 9 , wherein R 2 and R 3 are independently substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl.
11 . The compound of claim 10 , wherein R 2 and R 3 are independently substituted or unsubstituted alkyl.
12 . The compound of claim 11 , wherein R 2 and R 3 are independently substituted or unsubstituted C 1 -C 8 alkyl.
13 . The compound of claim 12 , wherein R 2 and R 3 are independently substituted or unsubstituted C 1 -C 4 alkyl.
14 . The compound of claim 13 , wherein R 2 and R 3 are independently —OH substituted or unsubstituted C 1 -C 4 alkyl.
15 . The compound of claim 13 , wherein R 2 and R 3 are independently unsubstituted C 1 -C 4 alkyl.
16 . The compound of claim 1 , wherein R 2 and R 3 are joined together to form a substituted or unsubstituted heterocycloalkyl or substituted or unsubstituted heteroaryl.
17 . The compound of claim 16 , wherein R 2 and R 3 are joined together to form a substituted or unsubstituted heterocycloalkyl.
18 . The compound of claim 17 , wherein R 2 and R 3 are joined together to form a substituted or unsubstituted C 5 -C 7 heterocycloalkyl.
19 . The compound of claim 18 , wherein R 2 and R 3 are joined together to form a substituted C 5 -C 7 heterocycloalkyl.
20 . The compound of claim 19 , wherein R 2 and R 3 are joined together to form an R 23 -substituted C 5 -C 7 heterocycloalkyl, wherein R 23 is independently a substituted or unsubstituted alkyl or substituted or unsubstituted heteroalkyl.
21 . The compound of claim 20 , wherein R 23 is independently a substituted or unsubstituted C 1 -C 8 alkyl or substituted or unsubstituted 2 to 8 membered heteroalkyl.
22 . The compound of claim 16 , wherein R 2 and R 3 are joined together to form a substituted or unsubstituted pyrrolidinyl.
23 . The compound of claim 16 , wherein R 2 and R 3 are joined together to form a substituted or unsubstituted piperazinyl.
24 . The compound of claim 1 comprising a protonated nitrogen cation.
25 . The compound of claim 1 comprising a plurality of protonated nitrogen cations.
26 . The compound of claim 1 having formula:
including pharmaceutical salts thereof.
27 . The compound of claim 1 having formula:
including pharmaceutical salts thereof.
28 . A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound of claim 1 .
29 . The compound of claim 1 for use in treating cancer in a subject in need thereof.
30 . The compound of claim 29 , wherein said compound is administered in an effective amount to said subject.
31 . The compound of claim 29 , wherein said compound is in a pharmaceutical composition comprising a pharmaceutically acceptable excipient.
32 . The compound of claim 29 , wherein said cancer is lung cancer, breast cancer, ovarian cancer, leukemia, lymphoma, melanoma, pancreatic cancer, sarcoma, bladder cancer, bone cancer, brain cancer, cervical cancer, colon cancer, esophageal cancer, gastric cancer, liver cancer, head and neck cancer, kidney cancer, myeloma, thyroid cancer, or prostate cancer.
33 . The compound of claim 29 , wherein said compound is co-administered with an effective amount of an anti-cancer agent.
34 . A method of modulating a kinase, a JAK, JAK2, TYK2, Src, c-Src, ABL1, ABL1 T315I, an Aurora kinase, Aurora A, GSK-3b, a CDK, a STAT, or STAT3, said method comprising contacting the protein with the compound claim 1 .
35 . The method of claim 34 , wherein the compound is in a pharmaceutical composition comprising a pharmaceutically acceptable excipient.
36 . A method of modulating a Janus kinase, said method comprising contacting said Janus kinase with the compound claim 1 .
37 . The method of claim 36 , wherein the compound is in a pharmaceutical composition comprising a pharmaceutically acceptable excipient.Join the waitlist — get patent alerts
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