# US 10,246,418 B2 · Crystal form of lenvatinib methanesulfonate salt and preparation method thereof

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- Number: US 10,246,418 B2
- Document ID: US10246418B2
- Status: Granted
- Kind: B2
- Application number: 15/575,352
- Filed: 2016-06-08
- Published: 2018-06-07
- Granted: 2019-04-02
- Earliest claimed: 2015-05-21
- Assignees: Crystal Pharmatech Co., Ltd.
- Applicants: Crystal Pharmatech Co., Ltd.
- Inventors: Minhua Chen; Yanfeng Zhang; Xiaojuan Diao; Xiaoyu Zhang
- Web page: https://patentgrep.com/patent/US10246418B2

## CPC

- C07D 215/48: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- A61K 31/47: Quinolines; Isoquinolines
- A61P 35/00: Antineoplastic agents
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07C 255/03: Mononitriles
- 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
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present disclosure relates to a novel crystalline form of lenvatinib mesylate and the preparation method thereof. The novel crystalline form of mesylate of the present disclosure can be used for treating invasive and differentiated thyroid cancer. The novel crystalline form of mesylate of the present disclosure has good solubility, stability, and remarkable purification effect in process. The preparation method of this novel crystalline form is simple, low cost, and has an important value for future optimization and development of the drug.

## Claims

### Claim 1

A crystalline Form M of compound (I) mesylate, wherein the X-ray powder diffraction pattern shows at least three characteristic peaks at 2theta values of 11.4°±0.2°, 6.1°±0.2°, 15.1°±0.2°, 12.5°±0.2°, 23.8°±0.2°, 21.8°±0.2°, 7.9°±0.2° and 20.2±0.2°.

### Claim 2 (depends on 1)

The crystalline Form M of compound (I) mesylate according to claim 1, wherein the three characteristic peaks are at 2theta values of 6.1°±0.2°, 7.9°±0.2° and 21.8°±0.2°.

### Claim 3 (depends on 2)

The crystalline Form M of compound (I) mesylate according to claim 2, wherein a at least additional one characteristic peak is at 2theta values of 11.4°±0.2°, 15.1°±0.2° or 12.5°±0.2°.

### Claim 4 (depends on 3)

The crystalline Form M of compound (I) mesylate according to claim 3, wherein the X-ray powder diffraction pattern shows characteristic peaks at 2theta values of 11.4°±0.2°, 15.1°±0.2° and 12.5°±0.2°.

### Claim 5 (depends on 2)

The crystalline Form M of compound (I) mesylate according to claim 2, wherein the X-ray powder diffraction pattern shows at least one additional characteristic peak at 2theta values of 23.8°±0.2° and 20.2°±0.2°.

### Claim 6 (depends on 5)

The crystalline Form M of compound (I) mesylate according to claim 5, wherein the X-ray powder diffraction pattern shows characteristic peaks are at 2theta values of 23.8°±0.2° and 20.2°±0.2°.

### Claim 7 (depends on 1)

The crystalline Form M of compound (I) mesylate according to claim 1, wherein an X-ray powder diffraction pattern is substantially as shown in FIG. 1.

### Claim 8 (depends on 1)

The crystalline Form M of compound (I) mesylate according to claim 1, wherein Fourier Transform Infrared (FT-IR) spectrometer has the following absorption bands expressed in reciprocal wave numbers: 535.72±1cm−1 and 1400.53±1cm −1.

### Claim 9 (depends on 1)

The crystalline Form M of compound (I) mesylate according to claim 1, wherein Fourier Transform Infrared (FT-IR) spectrometer has the following absorption bands expressed in reciprocal wave numbers: 1190.77±1cm−1 and 1692.73±1cm−1.