# US 12,180,242 B2 · Pharmaceutical crystal of contezolid acefosamil, preparation method therefor, and uses thereof

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- Number: US 12,180,242 B2
- Document ID: US12180242B2
- Status: Granted
- Kind: B2
- Application number: 17/285,889
- Filed: 2019-09-29
- Published: 2022-05-19
- Granted: 2024-12-31
- Earliest claimed: 2018-10-15
- Assignees: Shanghai Micurx Pharmaceutical Co., Ltd.
- Applicants: Shanghai Micurx Pharmaceutical Co., Ltd.
- Inventors: Xueliang Zhang; Xinghai Wang; Jinqian Liu; Mikhail Fedorovich Gordeev
- Web page: https://patentgrep.com/patent/US12180242B2

## CPC

- C07F 9/65583: {each of the hetero rings containing nitrogen as ring hetero atom}
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/04: Antibacterial agents
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present invention relates to a pharmaceutical crystal of contezolid acefosamil, a preparation method therefor, and uses thereof. The present invention also relates to a crystal or crystal complex of formula I, wherein R is selected from hydrogen, sodium or a mixture thereof in any ratio.

## Claims

### Claim 1

A crystal or crystal complex of a compound of formula I, wherein R is sodium,
wherein an X-ray powder diffraction (XRPD) pattern for the crystal or crystal complex of the compound of formula I exhibits diffraction peaks at least at the following 2θ positions: 6.9°, 14.7°, 15.5°, 16.5°, 20.2°, 22.9°, and 23.7°2θ, wherein the XRPD pattern is obtained with K-Alpha radiation having a wavelength of 1.54 Å, and wherein the 2θ position variation is ±0.2.

### Claim 2 (depends on 1)

The crystal or crystal complex of claim 1, wherein the crystal compound or crystal complex exhibits at least one diffraction peak selected from about 6.0˜8.0°2θ with a relative strength greater than all other diffraction peaks in its X-ray powder diffraction (XRPD) pattern, wherein the XRPD pattern is obtained with K-Alpha radiation having a wavelength of 1.54 Å.

### Claim 3 (depends on 2)

The crystal or crystal complex of claim 2, wherein the crystal compound or crystal complex exhibits a diffraction peak selected from about 23.0-24.0°2θ with a relative strength greater than all but the at least one diffraction peak selected from about 6.0˜8.0°2θ in its X-ray powder diffraction (XRPD) pattern, wherein the XRPD pattern is obtained with K-Alpha radiation having a wavelength of 1.54 Å.

### Claim 4 (depends on 1)

The crystal or crystal complex of claim 1, wherein the crystal or crystal complex has a melting point of 220±10° C.

### Claim 5 (depends on 1)

A method for preparing the crystal or crystal complex according to claim 1, comprising the following steps:
(1) preparing a compound of formula I
(2) dissolving the compound of formula I as a crude product in a mixed solution of an organic solvent and water;
(3) adding inorganic salt or organic solvent to the mixture, separating the product phase to remove part or all of the volatile substances, and adding organic solvent, so as to obtain a crystal via crystallization; and
(4) separating out the crystals of the compound of formula I.

### Claim 6 (depends on 5)

The method of claim 5, wherein in step (2), the organic solvent is selected from at least one of acetonitrile, acetone, methanol, ethanol, propanol, isopropanol, butanol, and tetrahydrofuran.

### Claim 7 (depends on 5)

The method of claim 5, wherein in step (3), the inorganic salt is selected from at least one of sodium chloride, sodium bromide, sodium iodide, sodium citrate, sodium dihydrogen phosphate, disodium hydrogen phosphate, sodium phosphate, sodium sulfate, sodium carbonate, sodium bicarbonate, sodium acetate and their hydrates.

### Claim 8 (depends on 5)

The method of claim 5, wherein in step (3), the organic solvent is selected from at least one of acetonitrile, acetone, methanol, ethanol, propanol, isopropanol, butanol, ethyl acetate, isopropyl acetate, methyl tert-butyl ether, and tetrahydrofuran.

### Claim 9 (depends on 1)

A method of treating a microbial infection in a mammal, comprising administering a therapeutically effective amount of the crystal or crystal complex of claim 1 to the mammal.

### Claim 10 (depends on 1)

A pharmaceutical composition comprising the crystal or crystal complex according to claim 1 and a pharmaceutically acceptable carrier.

### Claim 11 (depends on 9)

The method of claim 9, wherein the therapeutically effective amount of the crystal or crystal complex is administered in a pharmaceutical composition which further comprises a pharmaceutically acceptable carrier.

### Claim 12 (depends on 9)

The method of claim 9, wherein the method is for treating a bacterial infection.

### Claim 13 (depends on 12)

The method of claim 12, wherein the bacterial infection is a Gram-positive bacterial infection.