# US 8,772,483 B2 · Solid forms of (S)-2-amino-3-(4-(2-amino-6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid

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- Number: US 8,772,483 B2
- Document ID: US8772483B2
- Status: Granted
- Kind: B2
- Application number: 13/288,366
- Filed: 2011-11-03
- Published: 2012-05-17
- Granted: 2014-07-08
- Earliest claimed: 2010-11-05
- Assignees: Lexicon Pharmaceuticals, Inc.
- Applicants: Qun Li; Weifeng Hu; Xiaogen Yang; Jiangqiong Zhao; Matthew Mangzhu Zhao
- Inventors: Qun Li; Weifeng Hu; Xiaogen Yang; Jiangqiong Zhao; Matthew Mangzhu Zhao
- Web page: https://patentgrep.com/patent/US8772483B2

## CPC

- C07D 403/12: linked by a chain containing hetero atoms as chain links
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/08: for nausea, cinetosis or vertigo; Antiemetics
- A61P 1/10: Laxatives
- A61P 1/12: Antidiarrhoeals
- A61P 1/14: Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A61P 1/18: for pancreatic disorders, e.g. pancreatic enzymes
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/08: Bronchodilators
- A61P 25/06: Antimigraine agents
- A61P 25/22: Anxiolytics
- A61P 25/24: Antidepressants
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A61K 31/506: not condensed and containing further heterocyclic rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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)

## Abstract

Solid forms of (S)-2-amino-3-(4-(2-amino-6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid and salts thereof are disclosed. Pharmaceutical dosage forms and methods of their use are also disclosed.

## Claims

### Claim 1

A crystalline compound, which is (S)-2-amino-3-(4-(2-amino-6-((R)-1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)phenyl)propanoic acid besylate.

### Claim 2 (depends on 1)

The crystalline compound of claim 1, which is anhydrous.

### Claim 3 (depends on 2)

The crystalline compound of claim 2, which has a melting point of about 234° C. and/or a DSC peak at about 238° C.

### Claim 4 (depends on 3)

The crystalline compound of claim 3, which has an X-ray powder diffraction pattern comprising a peak at one or more of about 9.2, 15.9, 16.8, 18.4, 19.8, and/or 20.8 degrees 2θ.

### Claim 5 (depends on 1)

The crystalline compound of claim 1, which is a hydrate.

### Claim 6 (depends on 5)

The crystalline compound of claim 5, which has a melting point of about 218° C.

### Claim 7 (depends on 5)

The compound of claim 5, which has an X-ray powder diffraction pattern comprising a peak at one or more of about 8.7, 9.1, 13.4, 18.3, and/or 20.2 degrees 2θ.

### Claim 8 (depends on 2)

The crystalline compound of claim 2, which has a melting point of about 228° C. and/or a DSC peak at about 233° C.

### Claim 9 (depends on 2)

The crystalline compound of claim 2, which has an X-ray powder diffraction pattern comprising a peak at one or more of about 8.7, 9.5, 16.9, 17.5, 19.1, 19.7, 20.1, 20.4, 21.8, 22.1, and/or 26.4 degrees 2θ.

### Claim 10 (depends on 2)

The crystalline compound of claim 2, which has an X-ray powder diffraction pattern substantially the same as that shown in FIG. 1.

### Claim 11 (depends on 3)

The crystalline compound of claim 3, which has an X-ray powder diffraction pattern comprising a peak at one or more of about 7.6, 8.6, 12.9, 15.0, 15.3, 17.3, 19.2, 19.5, 20.2, and/or 23.1 degrees 2θ.

### Claim 12 (depends on 1)

A pharmaceutical dosage form comprising the crystalline compound of claim 1.