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Title: Method for reparing an amorphous sulfonamide
Abstract:The invention provides a pharmaceutical composition comprising a particular physical form of N-[4-[5-(cyclopentyloxy-carbonyl)amino-1-methylindol-3-yl-methyl]-3-methox ybenzoyl]-2-methylbenzenesulphonamide and polyvinylpyrrolidone. It also provides methods for preparing this physical form, and another physical form of N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-yl-methyl]-3-methoxy benzoyl]-2-methylbenzenesulphonamide useful in the preparation of the first mentioned physical form. The compositions are useful in the treatment of diseases in which leukotrienes are implicated, for example asthma.
Inventor(s): Holohan; James J. (Macclesfield, GB2), Edwards; Ieuan J. (Congleton, GB2)
Assignee: Zeneca Limited (London, GB2)
Filing Date:Mar 13, 1995
Application Number:08/403,132
Claims:1. A process for preparing an amorphous physical form of N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-yl-methyl]-3-methoxy benzoyl]-2-methylbenzenesulphonamide which is substantially free of other physical forms and has an infra-red spectrum (0.5% in KBr) having sharp peaks at 1690, 1530, 1490, 1420, 1155, 1060, 862 and 550 cm.sup.-1, said process comprising heating a crystalline, monohydrate physical form of N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-yl-methyl]-3-methoxy benzoyl]-2-methylbenzenesulphonamide which is substantially free of other crystalline forms and has an infra-red spectrum (0.5% in KBr) having sharp peaks at 3560, 1690, 1660, 1540, 1440, 1165, 880 and 858 cm.sup.-1, and an X-ray powder diffraction pattern having peaks at 2.theta.=10.0.degree., 11.2.degree., 14.6.degree., 19.8.degree. and 23.0.degree., at a temperature in the range of from 90.degree. to 125.degree. C. under reduced pressure.

2. A process as claimed in claim 1 in which the pressure is in the range of from 5 to 50 mbara.

3. A process as claimed in claims 1 or claim 2, in which the monohydrate physical form has been prepared by crystallization from hot aqueous acetone.

4. A process as claimed in claim 3, in which the crystallization has been performed by rapidly adding water so that the N-[4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-yl-methyl]-3-methoxy benzoyl]-2-methylbenzenesulphonamide initially separates out as an oil.
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Harvard Business School
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Queensland Health

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