# US 10,117,853 B2 · Cyclic amine derivative and pharmaceutical use thereof

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- Number: US 10,117,853 B2
- Document ID: US10117853B2
- Status: Granted
- Kind: B2
- Application number: 15/560,581
- Filed: 2016-03-24
- Published: 2018-04-19
- Granted: 2018-11-06
- Earliest claimed: 2015-03-24
- Assignees: Toray Industries, Inc.
- Applicants: Toray Industries, Inc.
- Inventors: Shuji Udagawa; Yasuhiro Morita; Naoki Izumimoto; Katsuhiko Iseki; Shunsuke Iwano; Tomoya Miyoshi; Yuji Osada; Tetsuro Koreeda; Masanori Murakami; Motohiro Shiraki; Kei Takahashi; Keiyu Oshida; Eriko Higashi
- Web page: https://patentgrep.com/patent/US10117853B2

## CPC

- A61K 31/4178: not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- A61K 31/4025: not condensed and containing further heterocyclic rings, e.g. cromakalim
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 29/02: without antiinflammatory effect
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 403/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 413/14: containing three or more hetero rings
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A compound exerts a strong analgesic effect against pain, in particular, neuropathic pain and/or fibromyalgia syndrome. A cyclic amine derivative represented by general formula or a pharmacologically acceptable salt thereof: A method of treating neuropathic pain includes administering a therapeutically effective amount of the cyclic amine derivative to a mammal. A method of treating fibromyalgia syndrome includes administering a therapeutically effective amount of the cyclic amine derivative to a mammal.

## Claims

### Claim 1

A cyclic amine derivative represented by general formula (I) or a pharmacologically acceptable salt thereof:
wherein A represents a group represented by formula (IIa) or (IIb),
wherein the stereochemical configuration of the asymmetric carbon marked with * is S;
R1 represents an alkyl group having 3 to 8 carbon atoms;
when A represents a group represented by the formula (IIa), n represents 2; and
when A represents a group represented by the formula (IIb), n represents 1.

### Claim 2 (depends on 1)

The cyclic amine derivative or the pharmacologically acceptable salt thereof according to claim 1, wherein A is a group represented by formula (IIa).

### Claim 3 (depends on 2)

The cyclic amine derivative or the pharmacologically acceptable salt thereof according to claim 2, wherein the cyclic amine derivative represented by formula (I) is a compound selected from the group consisting of
n-butyl (S)-3-(2-(3-(3-(dimethylamino)pyrrolidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)propanoate,
n-hexyl (S)-3-(2-(3-(3-(dimethylamino)pyrrolidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)propanoate,
n-heptyl (S)-3-(2-(3-(3-(dimethylamino)pyrrolidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)propanoate, and
n-octyl (S)-3-(2-(3-(3-(dimethylamino)pyrrolidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)propanoate.

### Claim 4 (depends on 1)

The cyclic amine derivative or the pharmacologically acceptable salt thereof according to claim 1, wherein A is a group represented by formula (IIb).

### Claim 5 (depends on 4)

The cyclic amine derivative or the pharmacologically acceptable salt thereof according to claim 4, wherein the cyclic amine derivative represented by formula (I) is a compound selected from the group consisting of
n-propyl 2-(2-(3-(4-morpholinopiperidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)acetate,
n-butyl 2-(2-(3-(4-morpholinopiperidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)acetate,
n-pentyl 2-(2-(3-(4-morpholinopiperidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)acetate,
n-hexyl 2-(2-(3-(4-morpholinopiperidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)acetate,
n-heptyl 2-(2-(3-(4-morpholinopiperidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)acetate, and
n-octyl 2-(2-(3-(4-morpholinopiperidin-1-yl)-3-oxopropyl)-1H-imidazol-1-yl)acetate.

### Claim 6 (depends on 1)

A medicine comprising the cyclic amine derivative or the pharmacologically acceptable salt thereof according to claim 1 as an active ingredient.

### Claim 7 (depends on 1)

An analgesic agent comprising the cyclic amine derivative or the pharmacologically acceptable salt thereof according to claim 1 as an active ingredient.

### Claim 8 (depends on 1)

A therapeutic agent for neuropathic pain comprising the cyclic amine derivative or the pharmacologically acceptable salt thereof according to claim 1 as an active ingredient.

### Claim 9 (depends on 1)

A therapeutic agent for fibromyalgia syndrome comprising the cyclic amine derivative or the pharmacologically acceptable salt thereof according to claim 1 as an active ingredient.

### Claim 10 (depends on 1)

A method of treating pain comprising administering a therapeutically effective amount of the cyclic amine derivative or the pharmacologically acceptable salt thereof according to claim 1 to a patient in need thereof.

### Claim 11 (depends on 1)

A method of treating neuropathic pain comprising administering a therapeutically effective amount of the cyclic amine derivative or the pharmacologically acceptable salt thereof according to claim 1 to a patient in need thereof.

### Claim 12 (depends on 1)

A method of treating fibromyalgia syndrome comprising administering a therapeutically effective amount of the cyclic amine derivative or the pharmacologically acceptable salt thereof according to claim 1 to a patient in need thereof.