Phosphorylated nitrone derivatives, method for preparing same, and compositions containing said derivatives

Process for the preparation of the compounds of general formula I ##STR19## in which R.sub.1 and R.sub.2 independently are a C.sub.1 -C.sub.18 alkyl or a phenyl group optionally substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or a halogen atom;

• Y is O or CH.sub.2 ;
• R is a hydrogen atom, a C.sub.1 -C.sub.18 alkyl group or a C.sub.6 -C.sub.18 aryl group and, when Y is O, R can also be an alkali metal;
• Ar is an aromatic nucleus selected from a phenyl, naphthyl, 2-pyridyl, 3-pyridyl and 4-pyridyl nucleus or a benzopyridyl nucleus of formula (i) ##STR20## in which one of X.sub.1, X.sub.2, X.sub.3 and X.sub.4 is a nitrogen atom, the others being a carbon atom, the endocyclic nitrogen atom of the 2-pyridyl, 3-pyridyl, 4-pyridyl or benzopyridyl nucleus (i) being optionally N-oxidized or substituted by a C.sub.1 -C.sub.18 alkyl group or a C.sub.6 -C.sub.18 aryl group and, the said aromatic nucleus being optionally C-substituted by one or more halogen atoms or one or more groups selected from C.sub.1 -C.sub.18 alkyl, cyano, hydroxyl, C.sub.1 -C.sub.18 alkoxy, C.sub.6 -C.sub.18 aryloxy, carboxyl, C.sub.1 -C.sub.18 alkoxy-carbonyl, nitro, trifluoromethyl, --SO.sub.3 M where M is an alkali metal or a hydrogen atom, amino optionally alkylated by one or two C.sub.1 -C.sub.18 alkyl groups;
• and --N.sup.+ R.sub.3 R.sub.4 R.sub.5 in which R.sub.3, R.sub.4 and R.sub.5 are selected independently of one another from C.sub.1 -C.sub.18 alkyl,
• it being understood that when the group Ar includes a quaternary nitrogen atom, it additionally includes the physiologically acceptable negative counterion necessary for electrical neutrality;
• and their physiologically acceptable salts obtained by the action of an inorganic or organic base or acid wherein a compound of formula II:
• ##STR21## (in which R.sub.1, R.sub.2, Y and R are as defined above), activated beforehand with a suspension of metallic zinc in an aqueous solution of ammonium chloride, is reacted in an appropriate solvent with an aldehyde of formula III:
• Ar--CH.dbd.O (III)
• (in which Ar is as defined above).

Process for the preparation of compounds of general formula I ##STR22## in which R.sub.1 and R.sub.2 independently are a C.sub.1 -C.sub.18 alkyl or a phenyl group optionally substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or a halogen atom;

• Y is O or CH.sub.2 ;
• R is a hydrogen atom, a C.sub.1 -C.sub.18 alkyl group or a C.sub.6 -C.sub.18 aryl group and, when Y is O, R can also denote an alkali metal;
• Ar is an aromatic nucleus selected from a phenyl, naphthyl, 2-pyridyl, 3-pyridyl and 4-pyridyl nucleus or a benzopyridyl nucleus of formula (i) ##STR23## in which one of X.sub.1, X.sub.2, X.sub.3 and X.sub.4 is a nitrogen atom, the others being a carbon atom,
• the said aromatic nucleus being optionally C-substituted by one or more halogen atoms or one or more groups selected from C.sub.1 -C.sub.18 alkyl, hydroxyl, C.sub.1 -C.sub.18 alkoxy, trifluoromethyl, C.sub.6 -C.sub.18 aryloxy, carboxyl, C.sub.1 -C.sub.18 alkoxycarbonyl, --SO.sub.3 M where M is an alkali metal or a hydrogen atom, amino optionally alkylated by one or two C.sub.1 -C.sub.18 alkyl groups;
• and --N.sup.+ R.sub.3 R.sub.4 R.sub.5 in which R.sub.3, R.sub.4 and R.sub.5 are selected independently of one another from C.sub.1 -C.sub.18 alkyl,
• it being understood that when the group Ar includes a quaternary nitrogen atom, it additionally includes the physiologically acceptable negative counterion necessary for electrical neutrality;
• and their physiologically acceptable salts obtained by the action of an inorganic or organic base or acid,
• including the reaction in an appropriate solvent of a compound of formula II ##STR24## (in which R.sub.1, R.sub.2, Y and R are as defined above) with a compound of formula III
• Ar--CH.dbd.O (III)
• (in which Ar is as defined above)
• in the presence of metallic zinc and of acetic acid.