IP Library Granted Patent US 10,167,271
Granted Patent B2
US 10,167,271 · App. 15/543,073 · Granted Jan 1, 2019

Fluoroquinolone carboxylic acid compounds and use thereof for the preparation of besifloxacin hydrochloride

Inventors: Jigar Bhavsar (Haryana, IN); Bhuwan Bhashkar (Haryana, IN); Anil Kumar (Haryana, IN)
Assignee: MANKIND PHARMA LTD
C07D401/04
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Quick Facts
Patent No.
US 10,167,271
App. No.
15/543,073
Granted
Jan 1, 2019
Kind
B2
Abstract

The present invention relates to novel fluoroquinolone carboxylic acid compounds and derivatives of Formula-I, and their salts wherein, R represents H or halogen. The present invention also relates to the use of novel fluoroquinolone carboxylic acid compounds and derivatives of Formula-I for preparation of Besifloxacin hydrochloride.

Claims (18)

1. Fluoroquinolone carboxylic acid compounds of Formula-I, and salts thereof:

wherein, R is hydrogen or a halogen.

2. Fluoroquinolone carboxylic acid compounds of Formula-I according to claim 1 , having structural Formula-A;

and salts thereof.

3. Fluoroquinolone carboxylic acid compounds of Formula-I and salts thereof,

wherein said carboxylic acid compounds are selected from:

4. Fluoroquinolone carboxylic acid compounds according to claim 1 , wherein said carboxylic acid compounds are R-enantiomers.

5. A process for preparation of Fluoroquinolone carboxylic acid compounds of Formula-I and salts thereof;

wherein, R represents hydrogen or halogen;

the process comprising:

reacting Schiff base of Formula-XIII with 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid of Formula-VII;

wherein, R is hydrogen or a halogen.

6. The process according to claim 5 , wherein the said Schiff base is prepared by reacting (R)-azepan-3-amine of Formula-XI with compound of Formula-XII;

wherein, R is hydrogen or a halogen.

7. The process according to claim 6 , wherein the said Schiff base is prepared in situ.

8. A process for preparation of Besifloxacin hydrochloride, comprising de-protection of fluoroquinolone carboxylic acid compounds and salts thereof, according to claim 1 , in presence of aqueous hydrochloric acid to form Besifloxacin hydrochloride.

9. The process according to claim 8 , wherein the fluoroquinolone carboxylic acid compounds and salts thereof are isolated in a solid state form before de-protection to Besifloxacin hydrochloride.

10. The process according to claim 8 , wherein the fluoroquinolone compounds and salts thereof are in situ converted to Besifloxacin hydrochloride without isolation in a solid state form.

Assignments (2)
CHANGE OF NAME Recorded Oct 30, 2017
From: MANKIND RESEARCH CENTRE
To: MANKIND PHARMA LTD
Reel/Frame 043982/0568 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2017
From: BHAVSAR, JIGAR; BHASHKAR, BHUWAN; KUMAR, ANIL
To: MANKIND RESEARCH CENTRE
Reel/Frame 042987/0554 →
Priority Claims (1)
IN 252/DEL/2015 · Jan 28, 2015 · national
Continuity (1)
Related Publication 20170362197A1 · Dec 21, 2017