IP Library Granted Patent US 10,208,007
Granted Patent B2
US 10,208,007 · App. 14/345,371 · Granted Feb 19, 2019

Use of strigolactones and strigolactone analogs for treating proliferative conditions

Inventors: Yoram Kapulnik (Karmei Yosef, IL); Hinanit Koltai (Rishon LeZion, IL); Ronit Yarden (Bethesda, MD); Cristina Prandi (Turin, IT)
C07D307/93A61K31/365A61K31/403A61K31/404C07D405/12C07D407/12C07D409/14C07D495/04A61K33/24
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Quick Facts
Patent No.
US 10,208,007
App. No.
14/345,371
Granted
Feb 19, 2019
Kind
B2
Abstract

Compound of formula X wherein P 1 is a fused-ring system comprising one 6-membered and two 5-membered rings; v indicates an S or R configuration; or individual isomers or pharmaceutically acceptable salts thereof, or mixtures thereof, in the preparation of an active agent for preventing or inhibiting cell proliferation or for inducing cell death.

Claims (21)

1. A method for inhibiting the proliferation of a cancerous cell in a patient in need thereof, or for inducing death of a cancerous cell in a patient in need thereof, wherein said cancerous cell comes from cancer selected from the group consisting of breast cancer, lung cancer, prostate cancer, colon cancer, leukemia and osteosarcoma, said method comprising the step of administering to said patient an effective amount of a compound of formula III

or its stereoisomer or pharmaceutically acceptable salt thereof;

wherein R 1 is C 1 -C 6 alkyl;

Z is CH, and Y is N;

R 6 is H or C 1 -C 6 alkyl;

R 2 and R 5 represent H; and

one of R 3 and R 4 represents H whereas the other is selected from the group consisting of H, Halogen, C 1 -C 6 alkyl, heterocyclyl, cycloalkyl, benzcycloalkyl, thienyl, 2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl, and phenyl or naphthyl substituted with nitro, dialkylamino or methoxy group.

2. The method of claim 1 , wherein the compound of formula III or its stereoisomer or pharmaceutically acceptable salt is part of a pharmaceutical composition.

3. The method of claim 2 , wherein the pharmaceutical composition further comprises one or more additional pharmaceutically active compounds.

4. The method of claim 1 , wherein the compound of formula III is selected from the group consisting of:

(±)(2E)-4-methyl-2-(4-methyl-5-oxo-2,5-dihydrofuran-2-yloxymethylene)-1,4-dihydro-2H-cyclopenta[b]indol-3-one;

(±)(2E)-7-bromo-4-methyl-2-(4-methyl-5-oxo-2,5-dihydrofuran-2-yloxymethylene)-1,4-dihydro-2H-cyclopenta[b]indol-3-one;

(±)(2E)-4-methyl-2-(4-methyl-5-oxo-2,5-dihydrofuran-2-yloxymethylene)-7-(4-nitrophenyl)-1,4-dihydro-2Hcyclopenta[b]indol-3-one;

(±)(2E)-4-methyl-2-(4-methyl-5-oxo-2,5-dihydrofuran-2-yloxymethylene)-7-(2-thienyl)-1,4-dihydro-2H-cyclopenta[b]indol-3-one;

(±)(2E)-4-methyl-2-(4-methyl-5-oxo-2,5-dihydrofuran-2-yloxymethylene)-7-[(4-dimethylamino)-phenyl]-1,4-dihydro-2H-cyclopenta[b]indol-3-one;

(2E)-7-(1-methoxynaphthalen-2-yl)-1,4-dimethyl-2-((4-methyl-5-oxo-2,5-dihydrofuran-2-yloxy)methylene)-1,2-dihydrocyclopenta[b]indol-3(4H)-one;

(2E)-2-[(2,5-dihydro-4-methyl-5-oxofuran-2-yloxy)methylene]-1,2-dihydro-7-[4-(dimethylamino)pheny]-1,4-dimethyl-cyclopenta[b]indole-3-(4H)-one;

(2E)-1,4-dimethyl-2-((4-methyl-5-oxo-2,5-dihydrofuran-2-yloxy)methylene)-7-(thiophen-2-yl)-1,2-dihydrocyclopenta[b]indol-3(4H)-one;

(2E)-2-[(2,5-dihydro-4-methyl-5-oxofuran-2-yloxy)methylene]-1,2-dihydro-7-(2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)-1,4-dimethylcyclopenta[b]indole-3-(4H)-one;

(±)2E-4-methyl-2-(4-methyl-5-oxo-2,5-dihydrofuran-2-yloxymethylene)-6-thiophen-2-yl-1,4-dihydro-2H-cyclopenta[b]indol-3-one;

and any combinations thereof.

Assignments (4)
CONFIRMATORY LICENSE Recorded Nov 18, 2019
From: GEORGETOWN UNIVERSITY
To: THE GOVERNMENT OF THE UNITED STATES, AS REPRESENTED BY THE SECRETARY OF THE ARMY
Reel/Frame 051043/0708 →
CONFIRMATORY LICENSE Recorded Nov 18, 2019
From: GEORGETOWN UNIVERSITY
To: THE GOVERNMENT OF THE UNITED STATES, AS REPRESENTED BY THE SECRETARY OF THE ARMY
Reel/Frame 051043/0949 →
CONFIRMATORY LICENSE Recorded Jun 21, 2017
From: GEORGETOWN UNIVERSITY
To: US ARMY, SECRETARY OF THE ARMY
Reel/Frame 042936/0477 →
CONFIRMATORY LICENSE Recorded Jun 21, 2017
From: GEORGETOWN UNIVERSITY
To: US ARMY, SECRETARY OF THE ARMY
Reel/Frame 042936/0490 →
Continuity (3)
Provisional Application 61614965 · Mar 23, 2012
Provisional Application 61537062 · Sep 21, 2011
Related Publication 20140323563A1 · Oct 30, 2014