IP Library Granted Patent US 8,829,203
Granted Patent B2
US 8,829,203 · App. 12/737,640 · Granted Sep 9, 2014

3′,6-substituted indirubins and their biological applications

Inventors: Laurent Meijer (Roscoff, FR); Leandros Skaltsounis (Athens, GR); Emmanuel Mikros (Ag. Paraskevi, GR); Prokopios Magiatis (Ambelakia, GR); Carl Johnson (Nashville, TN)
Assignee: Centre National de la Recherche Scientifique (CNRS)
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Quick Facts
Patent No.
US 8,829,203
App. No.
12/737,640
Granted
Sep 9, 2014
Kind
B2
Abstract

Indirubin derivatives of formula (I) wherein R represents -(A) n - R 1 or —CO—N(R 2 ,R 3 ) with •A being C1-C5 alkylene group, optionally substituted by one or several A 1 radical, A 1 being an halogen Br, OH, OR 4 or NH 2 , R 4 being C1-C5 alkyl; —R 1 being halogen, OH, N(R 2 , R 3 ); R 2 and R 3 , identical or different, being C1-C5 alkyl, optionally substituted by A 1 such as above defined, or R 2 and R 3 are part of a cycle with 5 or 6 elements optionally comprising another heteroatom such as O or N; •n=1−5. It also relates to the biological application thereof.

Claims (15)

1. An indirubin derivative of formula I

wherein

R represents -(A) n - R 1 or —CO—N(R 2 ,R 3 ) with

A being C1-C5 alkylene group, optionally substituted by one or several A 1 radical, A 1 being an halogen Br, OH, OR 4 or NH 2 , R 4 being C1-C5 alkyl;

R 1 being halogen, OH, N(R 2 , R 3 ); R 2 and R 3 , identical or different, being C1-C5 alkyl, optionally substituted by A 1 such as above defined, or R 2 and R 3 are part of a cycle with 5 or 6 elements optionally comprising another heteroatom such as O or N;

n=1-5,

with the exclusion of 2H-indol-2-one, 6-bromo-3-[(3E)-1,3-dihydro-3-[[2-(1-pyrrolidinyl)ethoxy]imino]-2H-indol-2-ylidene]˜1,3-dihydro- , (3Z).

2. A pharmaceutically acceptable salt of an indirubin derivative of claim 1 .

3. The indirubin derivative of claim 1 , wherein R represents-(A) n -R 1 , with R 1 being halogen, OH, N(R 2 , R 3 ) and R 2 and R 3 , identical or different, are C1-C5 alkyl, optionally substituted by A 1 such as above defined.

4. The indirubin derivative of claim 3 , wherein R 1 is Br or OH and A represents a —(CH 2 ) m1 —CH (R 1 )—(CH 2 ) m2 radical, wherein m 1 =1-3 and m 2 =0, 1-3.

5. The indirubin derivative of claim 3 , wherein R 1 is N (R 2 , R 3 ).

6. The indirubin derivative of claim 1 , wherein A is C1-C5 alkylene group.

7. The indirubin derivative of claim 1 , wherein R represents —CO—N (R 2 ,R 3 ), with R 2 and R 3 , identical or different, being a C1-C5 alkyl radical.

8. A pharmaceutical composition comprising a therapeutically effective amount of at least one indirubin derivative of claim 1 , in association with a pharmaceutically acceptable vehicle.

9. The pharmaceutical composition of claim 8 , wherein the at least one indirubin derivative is in a form suitable for an administration by intravenous route or intramuscular or subcutaneous.

Assignments (2)
CONFIRMATORY LICENSE Recorded May 19, 2023
From: VANDERBILT UNIVERSITY
To: NIH-DEITR
Reel/Frame 063704/0542 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 12, 2011
From: MEIJER, LAURENT; SKALTSOUNIS, LEANDROS; MIKROS, EMMANUEL; MAGIATIS, PROKOPIOS; JOHNSON, CARL
To: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)
Reel/Frame 027365/0286 →
Priority Claims (1)
EP 08161646 · Aug 1, 2008 · regional
Continuity (2)
Provisional Application 61085432 · Aug 1, 2008
Related Publication 20110136808A1 · Jun 9, 2011