# US 10,370,369 B2 · Acid addition salt of 3-aminoquinuclidine which does not exhibit deliquescence

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- Number: US 10,370,369 B2
- Document ID: US10370369B2
- Status: Granted
- Kind: B2
- Application number: 15/561,262
- Filed: 2016-03-31
- Published: 2018-05-03
- Granted: 2019-08-06
- Earliest claimed: 2015-03-31
- Assignees: Yuki Gosei Kogyo Co., Ltd.
- Applicants: Yuki Gosei Kogyo Co. Ltd.
- Inventors: Yukiko Takeda; Tetsuji Noda
- Web page: https://patentgrep.com/patent/US10370369B2

## CPC

- C07D 453/02: containing not further condensed quinuclidine ring systems
- C07C 55/07: Salts thereof
- C07C 57/15: Fumaric acid
- C07C 57/34: containing more than one carboxyl group
- C07C 309/25: having sulfo groups bound to carbon atoms of rings other than six-membered aromatic rings of a carbon skeleton
- C07C 309/30: of six-membered aromatic rings substituted by alkyl groups
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A novel acid addition salt of 3-aminoquinuclidine, which is an industrially useful compound as an intermediate of medicines and does not exhibit deliquescence, is provided. In particular, an acid addition salt of 3-aminoquinuclidine selected from the group consisting of racemic 3-aminoquinuclidine, (R)-3-aminoquinuclidine, and (S)-3-aminoquinuclidine, and acid selected from the group consisting of phosphoric acid, sulfuric acid, fumaric acid, terephthalic acid, oxalic acid, p-toluenesulfonic acid, (±)-10-camphorsulfonic acid, and (−)-10-camphorsulfonic acid, is provided.

## Claims

### Claim 1

An acid addition salt selected from the group consisting of:
[1] racemic 3-aminoquinuclidine.sesquiphosphate,
[2] racemic 3-aminoquinuclidine.monofumarate,
[3] racemic 3-aminoquinuclidine.monoterephthalate,
[4] racemic 3-aminoquinuclidine.monooxalate,
[5] racemic 3-aminoquinuclidine.mono-p-toluenesulfonate, and
[6] racemic 3-aminoquinuclidine.mono-(±)-10-camphorsulfonate;
wherein the acid addition salt does not exhibit deliquescence.

### Claim 2

An acid addition salt selected from the group consisting of:
[1] (R)-3-aminoquinuclidine.sesquiphosphate,
[2] (R)-3-aminoquinuclidine.monosulfate,
[3] (R)-3-aminoquinuclidine.monofumarate,
[4] (R)-3-aminoquinuclidine.monoterephthalate,
[5] (R)-3-aminoquinuclidine.monooxalate,
[6] (R)-3-aminoquinuclidine.mono-p-toluenesulfonate, and
[7] (R)-3-aminoquinuclidine.mono-(−)-10-camphorsulfonate;
wherein the acid addition salt does not exhibit deliquescence.

### Claim 3

An acid addition salt selected from the group consisting of:
[1] (S)-3-aminoquinuclidine.sesquiphosphate,
[2] (S)-3-aminoquinuclidine.monosulfate,
[3] (S)-3-aminoquinuclidine.monofumarate,
[4] (S)-3-aminoquinuclidine.monoterephthalate,
[5] (S)-3-aminoquinuclidine.monooxalate, and
[6] (S)-3-aminoquinuclidine.mono-p-toluenesulfonate;
wherein the acid addition salt does not exhibit deliquescence.