IP Library Granted Patent US 6,949,563
Granted Patent B2
US 6,949,563 · App. 10/752,342 · Granted Sep 27, 2005

(2-carboxamido)(3-amino)thiophene compounds

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 6,949,563
App. No.
10/752,342
Granted
Sep 27, 2005
Kind
B2
Abstract

Compounds represented by Formula (I): or a pharmaceutically acceptable salt or N-oxide thereof, wherein R1 is R2 is and R3 is C 0-4 alkyl, are useful in the treatment of cancer.

Claims (47)

1. A compound represented by Formula (I):

or a pharmaceutically acceptable salt or N-oxide thereof, wherein

R1 is

R2 is

 and

R3 is C 0-4 alkyl.

2. The compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, wherein R2 is

3. The compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, wherein R2 is

and R3 is hydrogen.

4. The compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, wherein R2 is

5. The compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, wherein R2 is

and R3 is hydrogen.

6. The compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, wherein R2 is

7. The compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, wherein R2 is

and R3 is C 0-4 alkyl.

8. The compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, wherein R2 is

and R3 is hydrogen.

9. The compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, wherein R2 is

and R3 is C 0-4 alkyl.

10. A composition comprising a compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, and a pharmaceutically acceptable carrier.

11. A composition comprising a compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof; and

an anti-neoplastic, anti-tumor, anti-angiogenic, or chemotherapeutic agent.

12. A composition comprising a compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, and a cytotoxic cancer therapeutic agent.

13. A composition comprising a compound according to claim 1 , or a pharmaceutically acceptable salt or N-oxide thereof, and an angiogenesis inhibiting cancer therapeutic agent.

14. A compound consisting of

N-(4-trifluoromethoxyphenyl) 3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide;

N-(4-bromo-3-methylphenyl) 3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide;

N-(2,2,3,3-tetrafluorobenzodioxan-6-yl) 3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide;

N-(4-chlorophenyl) 3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide;

4-{[2-(4-bromo-3-methylphenylcarbamoyl)thiophen-3-ylamino]methyl}pyridine-2-carboxylic acid methylamide;

4-{[2-(2,2,3,3-tetrafluorobenzodioxan-6-ylcarbamoyl)thiophen-3-ylamino]methyl}pyridine-2-carboxylic acid methylamide;

4-{[2-(4-chlorophenylcarbamoyl)thiophen-3-ylamino]methyl}pyridine-2-carboxylic acid methylamide;

N-(4-chlorophenyl) 3-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)amino]thiophene-2-carboxamide;

N-(4-bromo-3-methylphenyl) 3-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)amino]thiophene-2-carboxamide;

N-(2,2,3,3-tetrafluorobenzodioxan-6-yl) 3-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)amino]thiophene-2-carboxamide;

N-{[2-(4-trifluoromethoxyphenylcarbamoyl)thiophen-3-ylamino]methyl}pyridine-2-carboxylic acid methylamide; and

N-(4-Trifluoromethoxy)phenyl-3-[(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)amino]thiophene-2-carboxamide;

N-(4-chlorophenyl)-3-[(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)amino]thiophene-2-carboxamide;

3-[(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)amino]-N-(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)thiophene-2-carboxamide;

4-Methyl-N-(4-trifluoromethoxyphenyl)phenyl-3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide;

N-(4-chlorophenyl)-4-methyl-3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide;

N-(4-bromo-3-methylphenyl)-4-methyl-3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide;

4-Methyl-3-[(quinolin-4-ylmethyl)amino]-N-(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)thiophene-2-carboxamide;

3-{[(1-oxidoquinolin-4-yl)methyl]amino}-N-[4-(trifluoromethoxy)phenyl]thiophene-2-carboxamide

or a pharmaceutically acceptable salt, or N-oxide, thereof.

15. A method of treatment of hyperproliferative disorder comprising a step of administering an effective amount of the compound according to claim 1 wherein the hyperproliferative disorder is selected from the group consisting of breast cancer, head cancer, neck cancer, gastrointestinal cancer, leukemia, ovarian, bronchial, lunch or pancreatic cancer.

16. The method of claim 15 wherein the hyperproliferative disorder is sinonasal natural killer/T-cell lymphoma, testicular cancer (seminoma), thyroid carcinoma, malignant melanoma, adenoid cystic carcinoma, angiosarcoma, anaplastic large cell lymphoma, endometrial carcinoma, or prostate carcinoma.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2006
From: HONDA, AYAKO; WYNNE, GRAHAM MICHAEL; BLOXAM, JASON; LI, AN-HU; CREW, ANDREW PHILIP; PANICKER, BIJOY; TARDIBONO, JR., LAWRENCE
To: OSI PHARMACEUTICALS, INC.
Reel/Frame 017207/0823 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2006
From: HONDA, AYAKO; WYNNE, GRAHAM MICHAEL; BLOXAM, JASON; LI, AN-HU; CREW, ANDREW PHILIP; PANICKER, BIJOY; TARDIBONO, LAWRENCE, JR.
To: OSI PHARMACEUTICALS, INC.
Reel/Frame 017207/0831 →