C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 403/10 (2006.01) A61K 31/415 (2006.01)
Patent
CA 2160725
The present invention relates to a process for the preparation of the 2-n.butyl-3-[[2'-(tetrazol-5-yl) biphenyl-4-yl] methyl]-1,3-diazaspiro[4.4]- non-1-en-4-one by reaction of the corresponding nitrile with an alkaline azide and triethylamine hydrochloride, recovering the 2-n.butyl-3-[[2'- (tetrazol-5-yl) biphenyl-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one in form of one of its alkaline salts in aqueous solution, by neutralization of said alkaline salt and crystallization of the 2-n.butyt-3-[[2'-(tetrazol-5-yl)- biphenyl-4-yl]methyl]-1,3-diazaspiro[4.4] non-1-en-4-one thus precipitated either in a solvent containing less than 10% of water or in a solvent containing more than 10% of water in order to obtain two different crystalline forms (Forms A and B). Furthermore a novel crystalline form (Form B) of 2-n.butyl-3-[[2'-(tetrazol-5-yl)biphenyl-4-yl] methyl]-1,3- diazaspiro[4.4] non-1-en-4-one and pharmaceutical compositions containing it are described. Form A has the X-ray powder diffraction pattern given in Table II: TABLE II dI/I o 18.98100.00 10.895.81 9.497.43 8.486.60 7.1346.23 6.6811.25 6.307.45 5.458.85 5.2216.82 5.0311.81 4.7115.91 4.5845.40 4.4426.12 4.3225.44 4.2225.86 4.1121.72 3.9325.46 3.8533.89 3.77 27.76 3.38 9.09 3.33 11.75 3.23 13.68 3.14 11.99 2.80 8.97 2.71 9.50 Form B has the X-ray powder diffraction pattern given in Table I: TABLE I d I/I o 11.22 100.00 7.90 12.02 7.52 13.79 7.23 18.60 6.27 20.14 6.09 6.47 5.86 7.42 5.60 98.76 5.41 19.45 5.05 24.67 4.97 20.36 4.91 12.92 4.80 27.33 4.61 15.90 4.49 14.73 4.36 9.86 4.17 62.84 4.07 15.39 3.97 30.34 3.88 14.32 3.83 13.56 3.75 37.28 3.53 26.48 3.46 12.42 3.40 27.88 3.27 11.03 3.18 10.42 3.15 7.28 3.12 6.11 3.05 15.50 3.01 9.49 2.81 7.11 2.78 9.40
Bouloumie Colette
Caron Antoine
Chantreux Dominique
Sanofi-Aventis
Sim & Mcburney
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