IP Library Granted Patent US 10,683,288
Granted Patent B2
US 10,683,288 · App. 15/747,313 · Granted Jun 16, 2020

Epothilone B and dictyostatin analogs, their preparation and use

Inventors: James Leighton (New York, NY); Stephen Ho (New York, NY); Corinne Foley (New York, NY)
Assignee: The Trustees of Columbia University in the City of New York
C07D417/06C07D313/00C07D405/06C07D413/06C07D417/04C07D493/04
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Quick Facts
Patent No.
US 10,683,288
App. No.
15/747,313
Granted
Jun 16, 2020
Kind
B2
Abstract

A compound having the structure:

Claims (31)

1. A compound having the structure:

wherein

Z 1 is —CH 3 or —CF 3 ;

Z 2 is absent or present and when present is —O—;

Z 3 is

Z 4 is —O— of —NH—;

W is alkyl-N 3 , alkyl-SH, C 4 -C 20 alkyl-OH, C 4 -C 20 alkyl-NH 2 , alkyl-NH—R 1 , alkyl-NR 2 R 3 , alkyl-OR 1 , alkyl-OC(O)—R 1 , alkyl-NHAc, alkyl-NHC(O)—R 1 , -alkyl-NHC(O)—R 4 , alkyl-OC(O)—OR 1 , alkyl-NHC(O)—NHR 1 , alkyl-NHC(S)—NHR 1 or alkyl-maleimide,

wherein

R 1 is alkyl-N 3 , alkyl-SH, alkyl-OH, alkyl-NH 2 , or alkyl-maleimide,

R 2 is alkyl-N 3 , alkyl-SH, alkyl-OH, alkyl-NH 2 , or alkyl-maleimide,

R 3 is alkyl-N 3 , alkyl-SH, alkyl-OH, alkyl-NH 2 , or alkyl-maleimide, and

R 4 is alkyl-N 3 , alkyl-SH, alkyl-OH, alkyl-NH 2 or alkyl-maleimide,

α is a bond and is absent or present,

β is a bond and is absent or present,

χ is a bond and is absent or present,

δ is a bond and is absent or present,

wherein when α, β, and Z 2 are present, then χ is absent, and when χ is present, then α, β, and Z 2 are absent

or a stereoisomer or a pharmaceutically acceptable salt or ester thereof.

2. The compound of claim 1 having the structure:

or a stereoisomer or a pharmaceutically acceptable salt or ester thereof.

3. The compound of claim 1 having the structure:

or a stereoisomer or a pharmaceutically acceptable salt or ester thereof.

4. The compound of claim 1 , wherein W is —(CH 2 ) n —N 3 , wherein n is 1-20; or W is —(CH 2 ) n —NHAc, wherein n is 1-20, or a stereoisomer or a pharmaceutically acceptable salt or ester thereof.

5. The compound of claim 1 , wherein W is

wherein n is 1-20, or

wherein n is 4-20.

6. The compound of claim 3 having the structure:

or a stereoisomer or a pharmaceutically acceptable salt or ester thereof.

7. A composition comprising the compound of claim 1 and a carrier.

8. A composition, free of soil extract, comprising the compound of claim 1 .

9. A composition, free of soil extract, comprising at least 1 mg of the compound of claim 1 .

Assignments (1)
CONFIRMATORY LICENSE Recorded Aug 17, 2020
From: COLUMBIA UNIV NEW YORK MORNINGSIDE
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 053507/0948 →
Continuity (3)
Provisional Application 62196819 · Jul 24, 2015
Provisional Application 62196825 · Jul 24, 2015
Related Publication 20180215748A1 · Aug 2, 2018