Nitro compounds of the formula A-X.sub.i -NO.sub.2 and their compositions having anti-inflammatory, analgesic and anti-thrombotic activities

A compound having the formula:

• A--X.sub.1 --NO.sub.2
• or their salts, wherein:
• A=R(COX.sub.u).sub.t, wherein t=0 or 1;
• u=0 or 1,
• X=O, NH, NR.sub.1C, wherein R.sub.1C is a linear or branched alkyl having 1 to 10 C atoms;
• R is selected from the following groups:
• group I), wherein t=1 and u=1, and R is:
• ##STR26## wherein:
• R.sub.1 is an OCOR.sub.3 group;
• R.sub.3 is methyl, ethyl or a linear or branched C.sub.3 -C.sub.5 alkyl, or a nonaromatic or aromatic heterocycle with a single ring having 5 or 6 atoms containing one or more heteroatoms independently selected from O, N, and S;
• R.sub.2 is hydrogen, hydroxy, a halogen, a linear or branched alkyl having 1 to 4 C atoms, a linear or branched alkoxyl having 1 to 4 C atoms, a linear or branched perfluoroalkyl having 1 to 4 C atoms, nitro, amino, mono- or di-(C.sub.1-4) alkylamino;
• or
• R.sub.1 and R.sub.2 together are a dioxymethylene group, with the proviso that when X=NH, then X.sub.1 is ethylene and R.sub.2 =H;
• R.sub.1 cannot be OCOR.sub.3 in position 2 when R.sub.3 is methyl;
• nI is 0 or 1;
• group II) wherein t=1 and u=1, and R is:
• ##STR27## wherein:
• R.sub.II5 is H, a linear or branched C.sub.1 -C.sub.3 alkyl;
• R.sub.II6 is H, a linear or branched C.sub.1 -C.sub.3 alkyl;
• or, when R.sub.II5 is H, R.sub.II6 is benzyl;
• R.sub.II1, R.sub.II2 and R.sub.II3, independently from one another, are H, a linear or branched C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy, or Cl, F, Br;
• R.sub.II4 is R.sub.II1 or Br;
• group III), wherein t=1, u=1 and R is:
• ##STR28## wherein:
• R.sub.2a and R.sub.3a are H, a linear or branched, substituted or nonsubstituted C.sub.1 -C.sub.12 alkyl, allyl, with the proviso that when one of the two groups is allyl, the other is H;
• R.sub.1a is chosen from ##STR29## or group IIID, wherein R.sub.1a is:
• ##STR30## wherein in formula (IV), R.sub.III1 is H or SR.sub.III3, wherein R.sub.III3 has from 1 to 4 C atoms, linear or branched;
• R.sub.III2 is H or hydroxy;
• wherein in formula (XXI), R.sub.XXio is H, a linear or branched alkyl having from 1 to 6 C atoms, a C.sub.1 -C.sub.6 alkoxycarbonyl bound to a C.sub.1 -C.sub.6 alkyl, a C.sub.1 -C.sub.6 carboxylalkyl, a C.sub.1 -C.sub.6 alkanoyl, unsubstituted or substituted with a halogen, benzyl or halobenzyl, benzoyl or halobenzoyl;
• R.sub.XXi is H, a halogen, hydroxy, CN, a C.sub.1 -C.sub.6 alkyl, a C.sub.1 -C.sub.6 alkoxy, acetyl, benzyloxy, SR.sub.XXi2, wherein R.sub.XXi2 is an alkyl C.sub.1 -C.sub.6 ;
• a perfluoroalkyl having from 1 to 3 C atoms, a C.sub.1 -C.sub.6 carboxyalkyl, NO.sub.2, amino, sulphamoyl, a dialkyl sulphamoyl with the alkyl having from 1 to 6 C atoms, or a di-fluroalkyl sulphonyl with the alkyl having from 1 to 3 C atoms;
• R.sub.XXi1 is a halogen, CN, a C.sub.1 -C.sub.6 alkyl, a C.sub.1 -C.sub.6 alkoxy, acetyl, acetamide, benzyloxy, SR.sub.III3 is as above defined, a perfluoroalkyl having from 1 to 3 C atoms, hydroxy, a carboxyalkyl having from 1 to 6 C atoms, NO.sub.2, amino, a mono- or di-alkylamino having from 1 to 6 C atoms, sulphamoyl, a di-alkyl sulphamoyl having from 1 to 6 C atoms, or a di-fluoroalkyl sulphamoyl having from 1 to 6 atoms;
• or R.sub.XX1 together with R.sub.XXi1 is an alkylene dioxy having from 1 to 6 C atoms;
• wherein in formula (XXXV), Ar is phenyl, a hydroxyphenyl unsubstituted or substituted with a halogen, an alkanoyl and an alkoxy having from 1 to 6 C atoms, a trialalkyl having from 1 to 6 C atoms, cyclo-pentyl, cylo-hexyl, cyclo-heptyl, heteroaryl, furyl, pyridyl;
• group IV) wherein t=1, u=1, and R is ##STR31## wherein:
• R.sub.IVd and R.sub.IVd1 are at least one H and the other a linear or branched C.sub.1 -C.sub.6 alkyl, or a di-fluoroalkyl with the alkyl having from 1 to 6 C, or R.sub.IVd and R.sub.IVd1 together form a methylene group;
• wherein R.sub.IV is selected from:
• ##STR32## wherein in formula (II):
• R.sub.v-ii is a 1-6 C alkyl, a cycloalkyl having from 3 to 7 C atoms, an alkoxymethyl having from 1 to 7 C atoms, a trifluroalkyl having from 1 to 3 C atoms, vinyl, ethinyl, halogen, an alkoxy having from 1 to 6 C atoms, a di-fluoroalkoxy with the alkyl having from 1 to 7 C atoms, an alkoxymethyloxy having from 1 to 7 C atoms, an alkylthiomethyloxy with the alkyl having from 1 to 7 C atoms, an alkyl methylthio with the alkyl having from 1 to 7 C atoms, cyano, di-fluoromethylthio, phenyl or phenylalkyl substituted with the alkyl having from 1 to 8 C atoms;
• wherein in formula (III):
• R.sub.iv-iii is a linear or branched C.sub.2 -C.sub.5 alkyl, a C.sub.2 and C.sub.3 alkyloxy, allyloxy, phenoxy, phenylthio, a cycloalkyl having from 5 to 7 C atoms;
• group V), R is:
• ##STR33## wherein in the radicals of formula (II), R.sub.vii is H or a linear or branched alkyl having from 1 to 4 C atoms;
• R.sub.vii-1 is as defined for R.sub.vii or a linear or branched alkoxy having from 1 to 4 C atoms;
• Cl, F, Br;
• and the position of R.sub.vii-1 is o-, m- or p-;
• X.sub.1 in the formula A--X.sub.1 --NO.sub.2 is a bivalent connecting bridge selected from the following:
• --YO--
• wherein Y is:
• a linear or branched C.sub.1 -C.sub.20 alkylene, with the proviso that the connection bridge is excluded when R is:
• a radical of group I) except radicals of formula (Ib) and (Ic);
• a radical of group II) except radicals of formula (II.sub.b);
• a radical of group III) except radicals of group (IIID);
• a radical of group IV);
• a radical of group V), except radicals of formula (X) and including --(CH.sub.2).sub.4 -- for the compounds of formula (III) and (IV);
• or a cycloalkylene having from 5 to 7 carbon atoms, excluding this connecting bridge when R is a radical of formula (Ia) of group I;
• ##STR34## wherein n.sub.3 is 0 or an integer from 1 to 3, ##STR35## wherein nf' is an integer from 1 to 6, ##STR36## wherein R.sub.1f =H, --CH.sub.3 and nf is an integer from 1 to 6.