IP Library Granted Patent US 9,242,994
Granted Patent B2
US 9,242,994 · App. 14/387,033 · Granted Jan 26, 2016

Treatment of pancreatic and related cancers with 5-acyl-6,7-dihydrothieno[3,2-c]pyridines

Inventors: Marilyn D. Resh (New York, NY); Joseph Fraser Glickman (New York, NY); Elissaveta Petrova (New York, NY); Ouathek Ouerfelli (Fort Lee, NJ)
Assignees: Memorial Sloan-Kettering Cancer Center; The Rockefeller University
C07D495/04
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Quick Facts
Patent No.
US 9,242,994
App. No.
14/387,033
Granted
Jan 26, 2016
Kind
B2
Abstract

Methods for inhibiting the growth of pancreatic cancer cells or other cancer cells driven by Sonic hedgehog are disclosed. The method involves exposing the cells to 5-acyl-6,7-dihydrothieno[3,2-c]pyridines of formula (I)

Claims (20)

1. A compound of formula

or a pharmaceutically acceptable salt thereof;

wherein:

R 1 and R 2 are independently selected from hydrogen, halogen, (C 1 -C 4 )hydrocarbyl, (C 1 -C 4 )alkoxy, trifluoromethyl, trifluoromethoxy, cyano and nitro;

R 3 is

R 4 is selected from hydrogen, methyl, halomethyl, dihalomethyl, and trihalomethyl; and

A is phenyl.

2. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 1 , wherein R 1 is hydrogen; and R 2 is hydrogen or methyl.

4. The compound according to claim 1 , wherein R 1 is ortho relative to the point of attachment of phenyl to the thieno[3,2-c]pyridine; and R 2 is para to the point of attachment of phenyl to the thieno[3,2-c]pyridine.

5. The compound according to claim 1 , wherein R 1 is hydrogen or methyl and R 2 is chosen from hydrogen, methyl, methoxy, chloro, and fluoro.

6. The compound according to claim 1 , wherein R 1 and R 2 are the same and are chosen from hydrogen and halogen.

7. The compound according to claim 1 , wherein R 4 is hydrogen.

8. The compound according to claim 1 , wherein R 1 is meta relative to the point of attachment of phenyl to the thieno[3,2-c]pyridine.

9. The compound according to claim 8 , wherein R 1 is methyl and R 2 is hydrogen.

10. The compound according to claim 1 of the formula:

or a pharmaceutically acceptable salt thereof.

11. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound according to claim 10 , or a pharmaceutically acceptable salt thereof.

12. The compound according to claim 1 , wherein each of R 1 , R 2 , and R 4 is hydrogen, or a pharmaceutically acceptable salt thereof.

13. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound according to claim 12 , or a pharmaceutically acceptable salt thereof.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 6, 2015
From: GLICKMAN, JOSEPH FRASER
To: THE ROCKEFELLER UNIVERSITY
Reel/Frame 034908/0773 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 6, 2015
From: RESH, MARILYN D.; PETROVA, ELISSAVETA; OUERFELLI, OUATHEK
To: MEMORIAL SLOAN-KETTERING CANCER CENTER
Reel/Frame 034908/0792 →
CONFIRMATORY LICENSE Recorded Dec 31, 2014
From: SLOAN-KETTERING INST CAN RESEARCH
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 034716/0069 →
Continuity (2)
Provisional Application 61614954 · Mar 23, 2012
Related Publication 20150105419A1 · Apr 16, 2015