# US 5,352,685 A · Thieno[3,2-b]pyridine derivatives

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- Number: US 5,352,685 A
- Document ID: US5352685A
- Status: Granted
- Kind: A
- Application number: 08/029,551
- Filed: 1993-03-11
- Granted: 1994-10-04
- Earliest claimed: 1992-03-12
- Assignees: Mitsubishi Kasei Corporation
- Inventors: Akira Maruyama; Shigeru Ogawa; Satoshi Yamazaki; Akihiro Tobe
- Web page: https://patentgrep.com/patent/US5352685A

## CPC

- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/08: for nausea, cinetosis or vertigo; Antiemetics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/20: Hypnotics; Sedatives
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The thieno[3.2-b]pyridine derivative of the present invention promote the gastric emptying in male ddy mice and the gastric contraction in dogs sutured with a strain-gauge transducer. It is believed that the derivatives have the action to enhance gastric motor action and gastric emptying. Therefore, the compound of the present invention are effective for the prevention and therapeutical treatment of the symptoms caused by gastric hypanakinesis, such as heartburn, abdominal distension feeling, anorexia, unpleasant feeling on upper abdomen, abdominalgia, nausea, vomiting, etc. caused by the underlying diseases such as acute and chronic gastritis, stomach and duodenum ulcer, gastroneurosis, gastroptosis, etc. The present invention also encompasses a pharmaceutical composition containing as the effective ingredient a compound of the present invention, and a method for producing the same.

## Claims

### Claim 1

A thieno[3,2-b]pyridine derivative represented by formula (I): ##STR22## wherein Y represents --O-- or ##STR23## (wherein R.sup.3 represents hydrogen atom or a C.sub.1 -C.sub.6 alkyl group); R.sup.1 represents hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.2 -C.sub.6 alkenyl group, a C.sub.2 -C.sub.6 alkynyl group, a C.sub.3 -C.sub.8 cycloalkyl group, a C.sub.6 -C.sub.12 aryl group, or a C.sub.7 -C.sub.18 aralkyl group; R.sup.2 represents hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, halogen atom, hydroxyl group, a C.sub.1 -C.sub.6 alkoxyl group, amino group, a C.sub.1 -C.sub.6 alkylamino group, nitro group, mercapto group or a C.sub.1 -C.sub.6 alkylthio group; and A is represented by ##STR24## (wherein n is an integer of 1 to 4; R.sup.4 represents hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.8 cycloalkyl group or a C.sub.7 -C.sub.18 aralkyl group); a pharmaceutically acceptable salt thereof; an N-oxide derivative or a solvate thereof.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein Y represents --O-- or ##STR25## (wherein R.sup.3 represents hydrogen atom); R.sup.1 represents hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.6 -C.sub.12 aryl group or a C.sub.7 -C.sub.18 aralkyl group; R.sup.2 represents hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, or halogen atom; and A is represented by ##STR26## (wherein n is an integer of 2 or 3; R.sup.4 represents a C.sub.1 -C.sub.6 alkyl group).

### Claim 3 (depends on 2)

A compound according to claim 2, wherein R.sup.1 represents hydrogen atom or a C.sub.1 -C.sub.3 alkyl group; R.sup.2 represents hydrogen atom, a C.sub.1 -C.sub.3 alkyl group or halogen atom; and A is represented by ##STR27## (wherein n is an integer of 2 or 3; R.sup.4 represents a C.sub.1 -C.sub.3 alkyl group).

### Claim 4 (depends on 1)

A pharmaceutical composition containing a substance according to claim 1 and a pharmaceutically acceptable carrier.

### Claim 5 (depends on 1)

A pharmaceutical composition for preventing and therapeutically treating the diseases caused by gastrointestinal dismotility, containing a substance according to claim 1 as the effective ingredient and a pharmaceutically acceptable carrier.

### Claim 6 (depends on 1)

A pharmaceutical composition for preventing and therapeutically treating vomiting and/or nausea, containing a substance according to claim 1 as the effective ingredient and a pharmaceutically acceptable carrier.

### Claim 7 (depends on 1)

An analgesic composition containing a substance according to claim 1 as the effective ingredient and a pharmaceutically acceptable carrier.

### Claim 8 (depends on 1)

A pharmaceutical composition for preventing and therapeutically treating anxiety and/or neurosis, containing a substance according to claim 1 as the effective ingredient and a pharmaceutically acceptable carrier.

### Claim 9 (depends on 1)

A pharmaceutical composition for preventing and therapeutically treating arrhythmia, containing a substance according to claim 1 as the effective ingredient and a pharmaceutically acceptable carrier.

### Claim 10

A thieno[3,2-b]pyridine derivative represented by formula (Ib'), a pharmaceutically acceptable salt thereof, an N-oxide derivative thereof or a solvate thereof; ##STR28##

### Claim 11 (depends on 11)

A compound according to claim 11, in the form of an optical isomer which has the R-configuration.

### Claim 12

R-N-(1-azabicyclo[2.2.2]oct -3-yl)-7-hydroxythieno[3,2-b]pyridine-6-carboxamide hydrochloride.

### Claim 13 (depends on 10)

A pharmaceutical composition containing a substance according to claim 10, and a pharmaceutically acceptable carrier.

### Claim 14 (depends on 11)

A pharmaceutical composition containing a substance according to claim 11, and a pharmaceutically acceptable carrier.

### Claim 15 (depends on 12)

A pharmaceutical composition containing a substance according to claim 12, and a pharmaceutically acceptable carrier.

### Claim 16 (depends on 10)

A pharmaceutical composition for preventing and treating the disease caused by gastrointestinal dismotility, containing a substance according to claim 10, as the effective ingredient and a pharmaceutically acceptable carrier.

### Claim 17 (depends on 11)

A pharmaceutical composition for preventing and treating the disease caused by gastrointestinal dismotility, containing a substance according to claim 11, as the effective ingredient and a pharmaceutically acceptable carrier.

### Claim 18 (depends on 12)

A pharmaceutical composition for preventing and treating the disease caused by gastrointestinal dismotility, containing a substance according to claim 12, as the effective ingredient and a pharmaceutically acceptable carrier.

### Claim 19 (depends on 10)

A method of preventing and treating the disease caused by gastrointestinal dismotility, which comprises administering to a patient an effective amount of a compound claimed in claim 10.

### Claim 20 (depends on 11)

A method of preventing and treating the disease caused by gastrointestinal dismotility, which comprises administering to a patient an effective amount of a compound claimed in claim 11.

### Claim 21 (depends on 12)

A method of preventing and treating the disease caused by gastrointestinal dismotility, which comprises administering to a patient an effective amount of a compound claimed in claim 12.