IP Library Granted Patent US 7,915,261
Granted Patent B2
US 7,915,261 · App. 12/543,659 · Granted Mar 29, 2011

Pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound

Assignee: Astellas Pharma, Inc.
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Quick Facts
Patent No.
US 7,915,261
App. No.
12/543,659
Granted
Mar 29, 2011
Kind
B2
Abstract

A novel pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound or its pharmaceutically acceptable salt has a potent FAAH-inhibitory activity. Further, the pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound of the present disclosure is also useful in the treatment of urinary frequency and urinary incontinence, overactive bladder and/or pain.

Claims (43)

1. A pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound of a general formula (IV) or its pharmaceutically acceptable salt:

wherein the symbols in formula (IV) have the following meanings:

ring A 1 represents benzene ring, piperidine ring or piperazine ring;

L 1 represents lower alkylene, lower alkenylene, —N(R 15 )—C(═O)—, or —O—, wherein

R 15 represents H, or lower alkyl;

R 19 represents

(i) a group selected from the group consisting of H, halo, —CN, —CF 3 , lower alkyl, and —O-lower alkyl;

(ii) nitrogen-containing heteroaryl optionally substituted with the same or different 1 to 5 groups selected from the group consisting of H, halo, —CN, —CF 3 , lower alkyl, and —O-lower alkyl;

(iii) R 16 —(lower alkylene)-O—; or

(iv) R 17 R 18 N—C(═O)—,

wherein R 16 represents

(i) aryl optionally substituted with the same or different 1 to 5 groups selected from the group consisting of H, halo, —CN, —CF 3 , lower alkyl, and —O-lower alkyl;

(ii) nitrogen-containing heteroaryl optionally substituted with the same or different 1 to 5 groups selected from the group consisting of H, halo, —CN, —CF 3 , lower alkyl, and —O-lower alkyl; or

(iii) 3- to 8-membered cycloalkyl,

wherein R 17 and R 18 are the same or different, each representing H or lower alkyl, or

R 17 and R 18 may form, together with the N atom bonding thereto, 5- or 6-membered nitrogen-containing hetero ring, and

R 20 represents —CONH 2 .

2. A pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound of a general formula (V) or its pharmaceutically acceptable salt:

wherein the symbols in formula (V) have the following meanings:

L 2 represents lower alkylene, lower alkenylene, or -(lower alkenylene)-C(═O)—,

R 21 represents H, halo, —CN, —CF 3 , lower alkyl, or —O-lower alkyl, and

R 22 represents —CONH 2 .

3. A pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound or its pharmaceutically acceptable salt, the compound being one among the following group:

5-(aminocarbonyl)pyridin-3-yl 4-{2-[3-(aminocarbonyl)phenyl]ethyl}piperidine-1-carboxylate,

5-(aminocarbonyl)pyridin-3-yl 4-(2-{3-[(dimethylamino)carbonyl]phenyl}ethyl)piperidine-1-carboxylate,

5-(aminocarbonyl)pyridin-3-yl 4-{2-[3-(piperidin-1-ylcarbonyl)phenyl]ethyl}piperidine-1-carboxylate,

5-(aminocarbonyl)pyridin-3-yl 4-{2-[3-(pyrrolidin-1-ylcarbonyl)phenyl]ethyl}piperidine-1-carboxylate,

5-(aminocarbonyl)pyridin-3-yl 4-(2-phenylethyl)piperidine-1-carboxylate,

5-(aminocarbonyl)pyridin-3-yl 4-[2-(3-fluorophenyl)ethyl]piperidine-1-carboxylate, and

5-(aminocarbonyl)pyridin-3-yl 4-[2-(3-cyanophenyl)ethyl]piperidine-1-carboxylate.

4. A pharmaceutical composition comprising the pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound or its pharmaceutically acceptable salt of claim 1 as an active ingredient thereof.

5. A method for treating urinary frequency, urinary incontinence and/or overactive bladder, comprising administering a therapeutically effective amount of the pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound of claim 1 or its pharmaceutically acceptable salt to a patient.

6. A method for treating pain, comprising administering a therapeutically effective amount of the pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound of claim 1 or its pharmaceutically acceptable salt to a patient.

7. A pharmaceutical composition comprising the pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound or its pharmaceutically acceptable salt of claim 2 as an active ingredient thereof.

8. A method for treating urinary frequency, urinary incontinence and/or overactive bladder, comprising administering a therapeutically effective amount of the pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound of claim 2 or its pharmaceutically acceptable salt to a patient.

9. A method for treating pain, comprising administering a therapeutically effective amount of the pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound of claim 2 or its pharmaceutically acceptable salt to a patient.

10. The pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound or its pharmaceutically acceptable salt according to claim 3 , wherein the compound is 5-(aminocarbonyl)pyridin-3-yl 4-{2-[3-(aminocarbonyl)phenyl]ethyl}piperidine-1-carboxylate.

11. The pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound or its pharmaceutically acceptable salt according to claim 3 , wherein the compound is 5-(aminocarbonyl)pyridin-3-yl 4-(2-{3-[dimethylamino)carbonyl]phenyl}ethyl)piperidine-1-carboxylate.

12. The pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound or its pharmaceutically acceptable salt according to claim 3 , wherein the compound is 5-(aminocarbonyl)pyridin-3-yl 4-{2-[3-(piperidin-1-ylcarbonyl)phenyl]ethyl}piperidine-1-carboxylate.

13. The pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound or its pharmaceutically acceptable salt according to claim 3 , wherein the compound is 5-(aminocarbonyl)pyridin-3-yl 4-{2-[3-(pyrrolidin-1-ylcarbonyl)phenyl]ethyl}piperidine-1-carboxylate.

14. The pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound or its pharmaceutically acceptable salt according to claim 3 , wherein the compound is 5-(aminocarbonyl)pyridin-3-yl 4-(2-phenylethyl)piperidine-1-carboxylate.

15. The pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound or its pharmaceutically acceptable salt according to claim 3 , wherein the compound is 5-(aminocarbonyl)pyridin-3-yl 4-[2-(3-fluorophenyl)ethyl]piperidine-1-carboxylate.

16. The pyridyl non-aromatic nitrogen-containing heterocyclic-1-carboxylate compound or its pharmaceutically acceptable salt according to claim 3 , wherein the compound is 5-(aminocarbonyl)pyridin-3-yl 4-[2-(3-cyanophenyl)ethyl]piperidine-1-carboxylate.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2021
From: ASTELLAS PHARMA INC.
To: AUTOBAHN THERAPEUTICS, INC.
Reel/Frame 056405/0531 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 1, 2021
From: ISHII, TAKAHIRO; SUGANE, TAKASHI; MAEDA, JUN; NARAZAKI, FUMIE; KAKEFUDA, AKIO; SATO, KENTARO; TAKAHASHI, TATSUHISA; KANAYAMA, TAKATOSHI; SAITOH, CHIKASHI; SUZUKI, JOTARO; KANAI, CHISATO
To: ASTELLAS PHARMA INC.
Reel/Frame 056405/0571 →
Priority Claims (2)
JP P.2005-040197 · Feb 17, 2005 · national
JP P.2005-303065 · Oct 18, 2005 · national
Continuity (2)
Continuation 11816508
Related Publication 20100009971A1 · Jan 14, 2010