Patent ID: 7192942

Claim:
A process for making crystals of a 11β-benzaldoxim-estra-4,9-diene derivative, said crystals having an average particle size of from 3 μm to 25 μm and a maximum particle size of 100 μm, said process comprising subjecting a supersaturated solution containing said 11β-benzaldoxim-estra-4,9-diene derivative to a wet milling by a wet milling apparatus while crystallizing, in order to obtain a primary particle suspension; wherein said 11β-benzaldoxim-estra-4,9-diene derivative is a compound of formula (I), or a pharmacologically acceptable salt thereof: wherein R 1 represents hydrogen or an alkyl group with 1 to 6 carbon atoms; R 2 represents hydrogen, an alkyl group with 1 to 10 carbon atoms, an aryl group with 1 to 10 carbon atoms, an aralkyl group with 1 to 10 carbon atoms, an alkylaryl group with 1 to 10 carbon atoms, an acyl group with 1 to 10 carbon atoms or a —CONHR 4 group, R 3 represents hydrogen, an alkyl group with 1 to 10 carbon atoms, an aryl group with 1 to 10 carbon atoms, an aralkyl group with 1 to 10 carbon atoms, an alkylaryl group with 1 to 10 carbon atoms, or a —(CH 2 ) n —CH 2 X, an —OR 5 group, a —(CH 2 ) o —CH=CH(CH 2 ) p —R 6 group or —(CH 2 ) q C=CR 7 ; wherein n is 0, 1 or 2, o is 0, 1, 2 or 3, p is 0, 1 or 2 and q is 0, 1 or 2; wherein X represents hydrogen, a fluoro group, a chloro group, a bromo group, an iodo group, a cyano group, an azido group, a rhodano group, an —OR 5 group or an —SR 5 group; wherein Z represents hydrogen, an alkyl group with 1 to 10 carbon atoms, an aryl group with 1 to 10 carbon atoms, an aralkyl group with 1 to 10 carbon atoms, an alkylaryl group with 1 to 10 carbon atoms, an acyl group with 1 to 10 carbon atoms, a —CONHR 4 group, a —COOR 4 group, an alkali metal atom or an alkaline earth metal atom; wherein R 4 represents an alkyl group with 1 to 10 carbon atoms, an aryl group with 1 to 10 carbon atoms, an aralkyl group with 1 to 10 carbon atoms or an alkylaryl group with 1 to 10 carbon atoms; wherein R 5 represents hydrogen, an alkyl group with 1 to 10 carbon atoms, an awl group with 1 to 10 carbon atoms, an aralkyl group with 1 to 10 carbon atoms, an alkylaryl group with 1 to 10 carbon atoms or an acyl group with 1 to 10 carbon atoms; wherein R 6 represents a hydrogen, a hydroxy group, an alkyl group with 1 to 10 carbon atoms, an alkoxy group with 1 to 10 carbon atoms, an awl group with 1 to 10 carbon atoms, an aralkyl group with 1 to 10 carbon atoms, an alkylaryl group with 1 to 10 carbon atoms, an acyl group with 1 to 10 carbon atoms or an acyloxy group with 1 to 10 carbon atoms; and wherein R 7 represents a hydrogen, a fluoro group, a chloro group, a bromo group, an iodo group, an alkyl group with 1 to 10 carbon atoms, an aryl group with 1 to 10 carbon atoms, an aralkyl group with 1 to 10 carbon atoms, an alkylaryl group with 1 to 10 carbon atoms or an acyl group with 1 to 10 carbon atoms.