# US 5,352,694 A · Pharmaceutical agents

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- Number: US 5,352,694 A
- Document ID: US5352694A
- Status: Granted
- Kind: A
- Application number: 07/940,138
- Filed: 1992-09-03
- Granted: 1994-10-04
- Earliest claimed: 1991-09-05
- Assignees: Imperial Chemical Industries PLC
- Inventors: Murray W. Cuthbert
- Web page: https://patentgrep.com/patent/US5352694A

## CPC

- C07D 209/24: with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
- A61P 7/04: Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 27/16: Otologicals
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A physical form of (R)-3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol -3-ylmethyl]-N-(2-methylphenylsulphonyl)benzamide substantially free of other physical forms, which form is crystalline and has an X-ray powder diffraction pattern with specific peaks at 2.theta.=14.0, 19.4, 22.0, 22.4 and 24.7.degree. , processes for preparing the form and pharmaceutical compositions containing it. The compound is a leukotriene antagonist useful in the treatment of diseases such as asthma.

## Claims

### Claim 1

A physical form of (R)-3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol- 3-ylmethyl]-N-(2-methylphenylsulphonyl)benzamide, which form is crystalline, has an X-ray powder diffraction pattern with specific peaks at 2.theta.=14.0, 19.4, 22.0, 22.4 and 24.7.degree., has an infra-red spectrum (0.5% in KBr) having sharp peaks at 3390, 1620, 1250 and 885 cm.sup.-1, and has a melting point of 180.degree.-183 .degree. C.

### Claim 2

A physical form of (R)-3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol- 3-ylmethyl]-N-(2-methylphenylsulphonyl)benzamide, which form is crystalline, has an X-ray powder diffraction pattern with specific peaks at 2.theta.=14.0, 19.4, 22.0, 22.4 and 24.7.degree., has an infra-red spectrum (0.5% in KBr) having sharp peaks at 3390, 1620, 1250 and 885 cm.sup.-1, and has an endotherm maximum determined by differential scanning calorimetry (heating rate 10.degree. C./minute) of above 180 .degree. C.

### Claim 3 (depends on 2)

A physical form of (R)-3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol- 3-ylmethyl]-N-(2-methylphenylsulphonyl)benzamide as claimed in claim 2, which form has an endotherm maximum determined by differential scanning calorimetry (heating rate 10.degree. C./minute) of 189 .degree. C.

### Claim 4

A pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a physical form of (R)-3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol- 3-ylmethyl]-N-(2-methylphenylsulphonyl)benzamide, which form is crystalline, has an X-ray powder diffraction pattern with specific peaks at 2.theta.=14.0, 19.4, 22.0, 22.4 and 24.7.degree., has an infra-red spectrum (0.5% in KBr) having sharp peaks at 3390, 1620, 1250 and 885 cm.sup.-1, and has a melting point of 180.degree.-183 .degree. C.

### Claim 5

A pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a physical form of (R)-3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol- 3-ylmethyl]-N-(2-methylphenylsulphonyl)benzamide, which form is crystalline, has an X-ray powder diffraction pattern with specific peaks at 2.theta.=14.0, 19.4, 22.0, 22.4 and 24.7.degree., has an infra-red spectrum (0.5% in KBr) having sharp peaks at 3390, 1620, 1250 and 885 cm.sup.-1, and has an endotherm maximum determined by differential scanning calorimetry (heating rate 10 .degree. C./minute) of above 180 .degree. C.

### Claim 6 (depends on 5)

A pharmaceutical composition, as claimed in claim 5, in which the physical form of (R)-3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol- 3-ylmethyl]-N-(2-methylphenylsulphonyl)benzamide has an endotherm maximum determined by differential scanning calorimetry (heating rate 10 .degree. C./minute) of 189.degree. C.