IP Library › Granted Patent US 12,281,073
Granted Patent B2
US 12,281,073 · App. 18/347,345 · Granted Apr 22, 2025

Substituted piperidine compound and use thereof

Inventors: Tatsuhiko Fujimoto (Fujisawa, JP); Kentaro Rikimaru (Fujisawa, JP); Koichiro Fukuda (Fujisawa, JP); Hiromichi Sugimoto (Tokyo, JP); Takahiro Matsumoto (Fujisawa, JP); Norihito Tokunaga (Fujisawa, JP); Mariko Hirozane (Fujisawa, JP)
Assignee: Takeda Pharmaceutical Company Limited
C07D211/24A61P25/00C07D211/36C07D211/56C07D213/30C07D213/61C07D213/74C07D213/75C07D215/44C07D401/06C07D401/12C07D401/14C07D405/06C07D405/12C07D405/14C07D409/06C07D409/12C07D413/06C07D417/06C07D417/14
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Quick Facts
Patent No.
US 12,281,073
App. No.
18/347,345
Granted
Apr 22, 2025
Kind
B2
Abstract

Provided is a substituted piperidine compound having an orexin type 2 receptor agonist activity. A compound represented by the formula (I): wherein each symbol is as described in the DESCRIPTION, or a salt thereof has an orexin type 2 receptor agonist activity, and is useful as a prophylactic or therapeutic agent for narcolepsy.

Claims (27)

1. A compound having formula (III)

wherein R 2 is a cyclohexyl group substituted with a substituted phenyl group;

wherein the phenyl group is substituted with a hydroxy group, an optionally substituted C 1-6 alkoxy group, or a C 7-16 aralkyloxy group.

2. The compound of claim 1 , wherein the phenyl group is substituted with an optionally substituted C 1-6 alkoxy group.

3. The compound of claim 1 , wherein the phenyl group is substituted with a hydroxy group.

4. The compound of claim 1 , wherein the phenyl group is substituted with a C 7-16 aralkyloxy group.

5. A compound having formula (V)

wherein R 2 is a cyclohexyl group substituted with a substituted phenyl group;

wherein the phenyl group is substituted with a hydroxy group, an optionally substituted C 1-6 alkoxy group, or a C 7-16 aralkyloxy group; and

wherein R 5 is an amino-protecting group.

6. The compound of claim 5 , wherein the phenyl group is substituted with an optionally substituted C 1-6 alkoxy group.

7. The compound of claim 5 , wherein the phenyl group is substituted with a hydroxy group.

8. The compound of claim 5 , wherein the phenyl group is substituted with a C 7-16 aralkyloxy group.

9. The compound of claim 5 , wherein R 5 is selected from the group consisting of a formyl group, a C 1-6 alkyl-carbonyl group, a C 1-6 alkoxy-carbonyl group, a benzoyl group, a C 7-10 aralkyl-carbonyl group, a C 7-14 aralkyloxy-carbonyl group, a trityl group, a phthaloyl group, an N,N-dimethylaminomethylene group, a substituted silyl group, and a C 2-6 alkenyl group.

10. The compound of claim 5 , wherein R 5 is a C 1-6 alkoxy-carbonyl group.

11. The compound of claim 10 , wherein the R 5 is a tert-butoxycarbonyl group.

12. The compound of claim 11 , wherein the phenyl group is substituted with a C 7-16 aralkyloxy group.

13. The compound of claim 11 , wherein the phenyl group is substituted with a hydroxy group.

14. A method of preparing a compound of formula (III) according to claim 1 , comprising alkylating a compound of formula (II)

to obtain the compound of formula (III)

wherein R 2 is as defined in claim 1 .

15. The method of claim 14 , wherein the compound of formula (II) is alkylated to obtain the compound of formula (III) in a solvent and in the presence of a base.

16. The method of claim 15 , wherein the solvent is an ether solvent.

17. The method of claim 16 , wherein the solvent is tetrahydrofuran.

18. The method of claim 15 , wherein the base is an alkali metal hydride.

19. The method of claim 18 , wherein the base is sodium hydride.

20. A method of preparing a compound of formula (V) according to claim 5 , comprising aminating of a compound of formula (III)

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 28, 2025
From: FUJIMOTO, TATSUHIKO; RIKIMARU, KENTARO; FUKUDA, KOICHIRO; SUGIMOTO, HIROMICHI; MATSUMOTO, TAKAHIRO; TOKUNAGA, NORIHITO; HIROZANE, MARIKO
To: TAKEDA PHARMACEUTICAL COMPANY LIMITED
Reel/Frame 070032/0197 →
Priority Claims (1)
JP 2016-019834 · Feb 4, 2016 · national
Continuity (4)
Continuation 17154712 · Jan 21, 2021
Continuation 16410463 · May 13, 2019
Division 15421702 · Feb 1, 2017
Related Publication 20240174610A1 · May 30, 2024
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