Roussel Uclaf

Aventis Pharma S.a.

Hoechst Marion Roussel

Constantin Agouridas

Alexis Denis

Jean-Francois Chantot

Odile Le Martret

Claude Fromentin

Patrick Fauveau

Yannick Benedetti

Jean-Francedillaois Chantot

Alain Bonnefoy

Francois Bretin

Chantal Damais

Nicole Tessot

Lucien Nedelec

Gilles Hamon

Solange Gouin d'Ambrieres

Solange G D'Ambrieres

Odile L Martret

Francedillaois Bretin

Jean-Marie Pejac

Annie Martel

Novel compounds of the formulawherein the substituents are defined as in the application having antibiotic properties.

2-halogenated derivatives of 5-0 desosaminyl-erythronolide a, their preparation process and their antibiotic use

A subject of the invention is a process for the preparation of the compounds of formula (I): Wherein the substituents are defined as in the application. The compounds of this invention exhibit antibiotic properties.

2-halogenated derivatives of 5-O-desosaminyl-erythronolide A, their preparation process and their antibiotic use

Erythromycin derivatives, method for preparing same, and use thereof as drugs

Derivatives . . . use as medicaments

Derivatives of erythromycin, their preparation process and their use as medicaments

2-halogenated derivatives of 5-0 desosaminyl-erythronolide A, their preparation process and their antibiotic use

Erythromycin derivatives, method for preparing same and use thereof as

Intermediates for the preparation of compounds selected from the group consisting of a compound of the formula ##STR1## wherein R is ##STR2## n is an integer from 3 to 5, Ar is an optionally substituted heterocyclic selected from the group consisting of

Erythromycin compounds

Erythromycin derivatives, method for preparing same, and use thereof as

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R and R.sub.1 are --OH or --O-acyl of an organic carboxylic acid of 2 to 20 carbon atoms, R.sub.2 is hydrogen or methyl, R.sub.3 is --(CH.sub.2).sub.m --R.sub.4 or ##STR2## or --N--(CH.sub.2).sub.q --R.sub.4, m is an integer from 1 to 6, n, p and q are individually an integer from 0 to 6, A and B are individually selected from the group consisting of hydrogen, halogen and alkyl of 1 to 8 carbon atoms with the geometry of the double bond being E or Z or a mixture of E and Z or A and B form a triple bond, R.sub.4 is an optionally substituted mono- or polycyclic heterocycle and their non-toxic, pharmaceutically acceptable acid addition salts having antibiotic properties.

Erythromycins

Compounds of the formula ##STR1## wherein X and X' form C.dbd.O or C.dbd.NOR, R is selected from the group consisting of hydrogen, heterocycle, alkyl, alkenyl, alkynyl, all optionally substituted, ##STR2## R.sub.a and R.sub.b are hydrogen or a hydrocarbon group or form together with the nitrogen a heterocycle, or with A forms a 9-N, 11-O ring, and X' is hydrogen, --Y and Y' have the same definition as X and X', b is hydrogen or OR.sub.4, R.sub.4 is hydrogen or forms together with A a carbonate or a carbamate, A forms with C a double bond or A is OR'.sub.4, R'.sub.4 is hydrogen or forms together with B a carbonate or ##STR3## R.sub.2 is alkyl or --CONH.sub.2, --CONHCOR.sub.11 or --CONHSO.sub.2 R.sub.11, R.sub.11 is a hydrocarbon up to 18 carbon atoms, R.sub.3 is hydrogen, ##STR4## and Z is hydrogen or a carboxylic acid remainder and their non-toxic, pharmaceutically acceptable acid addition salts, their preparation and intermediates useful as antibiotics.

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and an optionally unsaturated hydrocarbon of up to 24 carbon atoms optionally interrupted by at least one heteroatom selected from the group consisting of oxygen, sulfur and nitrogen and optionally having at least one functional group or taken together form ##STR2## and R'.sub.1 and R'.sub.2 are individually selected from the group consisting of hydrogen and an optionally unsaturated hydrocarbon of up to 23 carbon atoms optionally interrupted by at least one heteroatom selected from the group consisting of nitrogen, oxygen and sulfur and optionally having at least one functional group, Z is hydrogen or acyl of an organic carboxylic acid of 1 to 18 carbon atoms and the wavy line indicates the 10-methyl may have R or S configuration or a mixture of R+S and their non-toxic, pharmaceutically acceptable acid addition salts having antibiotic properties.

Propanal derivatives

A compound selected from the group consisting of a compound of the formula ##STR1## wherein X is selected from the group consisting of --(NH).sub.a --, --CH.sub.2 --, --SO.sub.2 -- and --O--, a is 0 or 1, Y is --(CH.sub.2).sub.m - (CH.dbd.CH).sub.n --(CH.sub.2).sub.o -, m+n+o.ltoreq.8, n=o or 1, Ar is aryl optionally substituted with at least one member of the group consisting of --OH, halogen, --NO.sub.2, --CN, ##STR2## and alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, -N-alkyl, -N-alkenyl and N-alkynyl of up to 12 carbon atoms, R.sub.a and R.sub.b individually are hydrogen or alkyl of up to 12 carbon atoms, R.sub.3 is selected from the group consisting of alkyl of 1 to 12 carbon atoms, aryl, heteroaryl, carbocyclic aryl, aryloxy, arylthio and heterocyclic aryl, heterocyclic aryloxy and heterocyclic arylthio of 5 to 6 ring members containing at least one heteroatom, Hal is halogen, Z is hydrogen or acyl of an organic carboxylic acid and their non-toxic, pharmaceutically acceptable addition salts having antibacterial properties.

Erythromycin derivatives

An erythromycin compound of Formula I or its non-toxic acid addition salt having antibiotic activity.

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Nogent-Sur-Marne, France

Constantin Agouridas