N-substituted heterocyclic derivatives

A method of preparing a compound of formula (II):

• ##STR50## which method comprises:
• (I) reacting a compound of formula 14:
• R.sub.3 --T 14
• with a compound of formula 13:
• ##STR51## wherein:
• R.sub.3 is a hydrogen, a C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by one or more halogen atoms, a C.sub.2 -C.sub.6 alkenyl, a C.sub.3 -C.sub.7 cycloalkyl, a phenyl, a phenyl(C.sub.1 -C.sub.3)alkyl, or a phenyl(C.sub.2 -C.sub.3)alkenyl, said phenyl groups being unsubstituted or monosubstituted or polysubstituted by a halogen atom, a C.sub.1 -C.sub.4 alkyl, a C.sub.1 -C.sub.4 halogenoalkyl, a C.sub.1 -C.sub.4 polyhalogenoalkyl, a hydroxyl or a C.sub.1 -C.sub.4 alkoxy;
• and
• R.sub.4 and R.sub.5 are each independently a C.sub.1 -C.sub.6 alkyl, a phenyl or a phenyl(C.sub.1 -C.sub.3)alkyl, said alkyl, phenyl and phenylalkyl groups being unsubstituted or substituted by one or more halogen atoms or by a C.sub.1 -C.sub.4 perfluoroalkyl, a hydroxyl or a C.sub.1 -C.sub.4 alkoxy;
• or
• R.sub.4 and R.sub.5 together form a group of the formula .dbd.CR.sub.7 R.sub.8, in which R.sub.7 is hydrogen, a C.sub.1 -C.sub.4 alkyl or a phenyl and R.sub.8 is a C.sub.1 -C.sub.4 alkyl or a phenyl;
• or
• R.sub.4 and R.sub.5 together are either a group of the formula (CH.sub.2).sub.n or a group of the formula (CH.sub.2).sub.p Y--(CH.sub.2).sub.q, in which Y is an oxygen atom, a sulfur atom, or a carbon atom substituted by a C.sub.1 -C.sub.4 alkyl group, a phenyl or a phenyl(C.sub.1 -C.sub.3)alkyl, or a group N--R.sub.6, in which R.sub.6 is a hydrogen, a C.sub.1 -C.sub.4 alkyl, a phenyl(C.sub.1 -C.sub.3)alkyl, a C.sub.1 -C.sub.4 alkylcarbonyl, a C.sub.1 -C.sub.4 halogenoalkylcarbonyl, a C.sub.1 -C.sub.4 polyhalogenalkylcarbonyl, a benzoyl, an alpha-aminoacyl or an N-protecting group;
• or
• R.sub.4 and R.sub.5, together with the carbon atom to which they are bonded, form an indane or an adamantane;
• p+q=m;
• n is an integer between 2 and 11;
• m is an integer between 2 and 5;
• X is an oxygen atom or sulfur atom;
• and
• z and t are zero and one is zero and the other is one;
• with the limitations that:
• if z and t are zero and X is an oxygen atom, R.sub.4 and R.sub.5 are other than a C.sub.1 -C.sub.6 alkyl, a phenyl or a phenyl(C.sub.1 -C.sub.3)alkyl, said alkyl, phenyl and phenylalkyl groups being unsubstituted or substituted by one or more halogen atoms or by a C.sub.1 -C.sub.4 perfluoroalkyl, a hydroxyl or a C.sub.1 -C.sub.4 alkoxy;
• or R.sub.4 and R.sub.5 together are other than a group N--R.sub.6 in which R.sub.6 is a hydrogen, a C.sub.1 -C.sub.4 alkyl or a phenyl(C.sub.1 -C.sub.3)alkyl;
• and n is other than 6;
• or when R.sub.3 represents a substituted phenyl group, R.sub.4 and R.sub.5 together are other than a (CH.sub.2).sub.n group in which n is between 3 and 5;
• and
• if z=1 and R.sub.3 is a phenyl, R.sub.4 and R.sub.5 are each other than a methyl;
• or R.sub.4 is a C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by one or more halogen atoms;
• and R.sub.5 is a cycloalkyl or a (C.sub.3 -C.sub.7) cycloalkylmethyl, which is unsubstituted or substituted by one or more halogen atoms;
• or R.sub.4 and R.sub.5 are each a cyclopropyl;
• T is C(OR).sub.3, HN.dbd.C--OR or COHal, wherein R is C.sub.1 -C.sub.4 alkyl and Hal is a halogen atom;
• A is an OH group, an NH.sub.2 group or a group R', wherein R' is hydrogen or a C.sub.1 -C.sub.4 alkyl group;
• and
• (II) optionally treating the resulting compounds in which X.dbd.O with Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphate disulfide) to transform them into compounds of formula (II) in which X.dbd.S.