# US 9,751,840 B2 · R-7-(3-aminomethyl-4-methoxyimino-3-methyl-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-acid and L-aspartic acid salt, process for the preparation thereof and pharmaceutical composition comprising the same for antimicrobial

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- Number: US 9,751,840 B2
- Document ID: US9751840B2
- Status: Granted
- Kind: B2
- Application number: 15/247,686
- Filed: 2016-08-25
- Published: 2016-12-15
- Granted: 2017-09-05
- Earliest claimed: 2009-07-27
- Assignees: Aribio Co., Ltd.
- Applicants: Aribio Co. Ltd.
- Inventors: Dong Rack Choi; Jin Yang; Sue Hye Yoon; Sung Jae Pyun; Seung Hwan Kim; Seung Kyoo Seong; Jei Man Ryu
- Web page: https://patentgrep.com/patent/US9751840B2

## CPC

- C07D 215/56: with oxygen atoms in position 4
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 9/145: {with organic compounds}
- A61K 9/2059: {Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin}
- A61K 9/4858: {Organic compounds}
- A61K 31/4375: the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/04: Antibacterial agents
- C07C 229/24: having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 498/06: Peri-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Disclosed herein are R-7-(3-aminomethyl-4-methoxyimino-3-methyl-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid and L-aspartic acid salt, process for the preparation thereof and pharmaceutical composition comprising the same for antimicrobial. Because the R-7-(3-aminomethyl-4-methoxyimino-3-methyl-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid and L-aspartic acid salt is more soluble and less toxic and has less side effects as an antimicrobial agent than hydrochloride and the other salts (D-aspartate and phosphate) conventionally used, the salt may be useful for oral and injectable administration.

## Claims

### Claim 1

A composition comprising an aspartate salt of R-7-(3-aminomethyl-4-methoxyimino-3-methyl-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro [1,8]naphthyridine-3-carboxylic acid.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the aspartate salt of a quinolone antimicrobial agent is L-aspartate of a quinolone antimicrobial agent.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the aspartate salt of a quinolone antimicrobial agent is D-aspartate of a quinolone antimicrobial agent.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the composition further comprises a pharmaceutically acceptable carrier.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the composition is formulated for oral or injectable administration.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the composition is a liquid form.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the composition is a solid form.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the composition comprises 0.1 to 50% of the aspartate salt of a quinolone antimicrobial agent by weight based on a total weight of the composition.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the aspartate salt of a quinolone antimicrobial agent has water solubility of at least 100 mg/ml at room temperature.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the aspartate salt of a quinolone antimicrobial agent has at least 70% bioavailability.

### Claim 11 (depends on 1)

A method of treating a disease of Gram-negative bacteria, methicillin resistant bacteria, or quinolone-resistant bacteria comprising administering to a subject in need thereof a therapeutically effective amount of a composition of claim 1.