# US 9,751,878 B2 · Tetrahydronaphthyridine somatostatin receptor 5 antagonists

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- Number: US 9,751,878 B2
- Document ID: US9751878B2
- Status: Granted
- Kind: B2
- Application number: 15/139,531
- Filed: 2016-04-27
- Published: 2016-08-18
- Granted: 2017-09-05
- Earliest claimed: 2013-10-07
- Assignees: Takeda Pharmaceutical Company Limited
- Applicants: Takeda Pharmaceutical Company Limited
- Inventors: Shizuo Kasai; Hideki Hirose; Takeshi Yamasaki; Tohru Yamashita; Asato Kina; Yoichi Nishikawa
- Web page: https://patentgrep.com/patent/US9751878B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A compound having an SSTR5 antagonist action and use of the compound as a medicament are provided. Specifically, a compound represented by the following formula: wherein each symbol is as defined herein, or a salt thereof, a medicament comprising the compound or a salt thereof, and use of the compound or a salt thereof as an agent for the prophylaxis or treatment of diabetes mellitus are provided.

## Claims

### Claim 1

A compound represented by the following formula:
wherein
ring P is pyridine; W is methylene;
ring A is piperidine, azetidine, or pyrrolidine;
ring B is
(1) a benzene ring optionally substituted by 1 to 4 substituents selected from: a halogen atom; a C3-10 cycloalkyl group; a C1-6 alkoxy group; and a C6-14 aryl group optionally substituted by 1 to 3 halogen atom(s), or
(2) pyridine optionally substituted by 1 to 3 substituents selected from: a C1-6 alkyl group; a C3-10 cycloalkyl group; a C1-6 alkoxy group and a C6-14 aryl group optionally substituted by 1 to 3 halogen atom(s);
R1 is COOH and R2 is a hydrogen atom, a C1-6 alkyl group optionally substituted by a C1-6 alkoxy group, a C3-10 cycloalkyl group, or COOH; or
R1 is a hydrogen atom and R2 is COOH; and
each of R3, R4, R5, and R6 is a hydrogen atom.

### Claim 2 (depends on 1)

A medicament comprising the compound of claim 1 or a salt thereof.

### Claim 3 (depends on 1)

A method for treating diabetes mellitus in a mammal, comprising administering to the mammal an effective amount of the compound according to claim 1 or a salt thereof.

### Claim 4 (depends on 1)

A method for antagonizing somatostatin receptor subtype 5 in a mammal, comprising administering to the mammal an effective amount of the compound according to claim 1 or a salt thereof.

### Claim 5 (depends on 1)

The compound according to claim 1 or a salt thereof, wherein ring P constitutes 1,6-tetrahydronaphthyridine or 1,7-tetrahydronaphthyridine together with the adjacent ring.

### Claim 6 (depends on 1)

The compound according to claim 1 or a salt thereof, wherein ring P constitutes 1,6-tetrahydronaphthyridine together with the adjacent ring.

### Claim 7 (depends on 1)

The compound according to claim 1 or a salt thereof, wherein ring A is piperidine.

### Claim 8 (depends on 1)

The compound according to claim 1 or a salt thereof, wherein ring B is a benzene ring optionally substituted by 1 to 4 substituents selected from: a halogen atom; a C3-10 cycloalkyl group; a C1-6 alkoxy group; and a C6-14 aryl group optionally substituted by 1 to 3 halogen atom(s).

### Claim 9

A compound represented by the following formula:
wherein
ring P constitutes 1,6-tetrahydronaphthyridine together with the adjacent ring;
ring A is piperidine;
ring B is a benzene ring optionally substituted by 1 to 4 substituents selected from:
a halogen atom, a C3-10 cycloalkyl group, a C1-6 alkoxy group, and a C6-14 aryl group optionally substituted by 1 to 3 halogen atom(s); and
R1 is COOH and R2 is a hydrogen atom, a C1-6 alkyl group optionally substituted by a C1-6 alkoxy group, a C3-10 cycloalkyl group; or COOH; or
R1 is hydrogen atom and R2 is COOH;
or a salt thereof.