# US 2014/0155610 A1 · Preparation of pyridonecarboxylic acid antibacterials

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- Number: US 2014/0155610 A1
- Document ID: US20140155610A1
- Status: Published application
- Kind: A1
- Application number: 14/176,334
- Filed: 2014-02-10
- Published: 2014-06-05
- Earliest claimed: 2004-07-30
- Assignees: AbbVie Inc.
- Applicants: AbbVie, Inc.
- Inventors: Anthony HAIGHT; David M. BARNES; Geoff G.Z. ZHANG
- Web page: https://patentgrep.com/patent/US20140155610A1

## CPC

- C07D 213/74: Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- A01N 43/40: six-membered rings
- C07D 205/04: having no double bonds between ring members or between ring members and non-ring members
- C07D 213/73: Unsubstituted amino or imino radicals
- C07D 213/75: Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C07D 401/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

A process for making 1-(6-amino-3,5-difluoropyridin-2-yl)-8-chloro-6-fluoro-7-(3-hydroxyazetidin-1-yl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid, and therapeutically acceptable salts thereof, and intermediates used in the process are disclosed.

## Claims

### Claim 1

A process for making ethyl
1-(6-amino-3,5-difluoropyridin-2-yl)-6-fluoro-7-(3-isobutyryloxy)azetidin-l-yl)-4-oxo-1,4-di hydroquinoline-3-carboxylate, or a salt thereof, comprising:
(a) reacting ethyl
(2E/Z)-3-((6-amino-3,5-difluoropyridin-2-yl)amino)-2-(2,4,5-trifluorobenzoyl)-2-propenoate, or a salt thereof, lithium chloride and 1,8-diazabicyclo[5.4.0]undec-7-ene and not isolating the product;
(b) reacting the product of step (a), 3-azetidinol hydrochloride and 1,8-diazabicyclo[5.4.0]undec-7-ene and not isolating the product; and
(c) reacting the product of step (b) and isobutyric anhydride and isolating or not isolating the product.