Roussel Uclaf

Other

Hoechst Marion Roussel

Forest Laboratories Holdings Limited

Novexel

Pfizer Ireland Pharmaceuticals

Alain Bonnet

Alain Priour

Jozsef Aszodi

Mahendra G Dedhiya

Alexandre Giuliani

Sisir Bhattacharya

Peter Spargo

Valérie Ravaux

Véronique Ducandas

Jean-Georges Teutsch

Rene Heymes

Solange Gouin d'Ambrieres

Alain Mazurie

Jean-Francois Chantot

Germain Costerousse

Didier Pronine

Michel Delthil

Jacques Lagouardat

Bernadette Chappert

Raphael Bouchet

Gilles Oddon

Daniel Guilmard

Francoise Gambier

The present invention relates to novel crystalline forms of sodium salt of trans-7-oxo-6-(sulphooxy)-1,6-diazabicyclo[3,2,1]octane-2-carboxamide (e.g., NXL-104) thereof. The present invention relates to compositions comprising a crystalline form of sodium salt of trans-7-oxo-6-(sulphooxy)-1,6-diazabicyclo[3,2,1]octane-2-carboxamide (e.g., NXL-104) alone or in combination with an antibacterial agent (e.g., ceftaroline fosamil). Processes for the preparation of the crystalline forms and methods of treating bacterial infections by administering the crystalline forms alone or in combination with an antibacterial agent (e.g., ceftaroline fosamil) are also described.

Crystalline forms of trans-7-oxo-6-(sulphooxy)-1,6-diazabicyclo[3,2,1]octane-2-carboxamide sodium salt

Crystalline forms of trans-7-oxo-6-(sulphooxy)-1,6-Diazabicyclo[3,2,1]octane-2-carboxamide sodium salt

The disclosure relates to a method for preparing a compound of formula (I), wherein Pand Pare groups protecting the carboxylic acid and oxyamine functions, starting from pyroglutamic acid (S). The disclosure also relates to novel intermediates.

Method for preparing disubstituted piperidine and intermediates

Novel compounds of the formula ##STR1## wherein A is --OH and B forms with the 10-carbon a carbon--carbon double bond or A and B together form a carbonate or a carbamate, --OZ is selected from the group consisting of --OH, etherified hydroxy or esterified hydroxy and its non-toxic, pharmaceutically acceptable acid addition salts.

Erythromycins

5-O-deosaminyl 6-O-methyl erythronolide A derivatives, preparation

1(2H) quinoline carboxylic acid derivatives, method for preparing same,

5-O-deaominyl 6-O-methyl erythronolide a derivatives, method for

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R is selected from the group consisting of ##STR2## and R.sub.b --NH--, Ra is an organic radical, Ri and Rj are individually selected from the group consisting of hydrogen, aliphatic hydrocarbon, aromatic hydrocarbon and heterocycle or taken together with the nitrogen atom to which they are attached form an optionally substituted ring, Rb is selected from the group consisting of carbocyclic aryl and heterocyclic aryl, both optionally substituted, R.sub.1A is selected from the group consisting of ##STR3## and ##STR4## are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, Z.sub.A is selected from the group consisting of a simple bond, --O-- and optionally oxidized sulfur, R.sub.3A is selected from the group donsisting of optionally substituted carbocyclic aryl and heterocyclic aryl, optionally substitute quaternary ammonium, acetyle, carbamoyl, alkoxycarbonyl, alkyl and haloalkyl of 1 to 4 carbon atoms, --CN and azido, R.sub.4 is selected from the group consisting of hydrogen and methoxy, A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, magnesium, --NH.sub.4, an organic amine and esterified carboxy or COOA is --COO.sup.--, n.sub.2 is an integer from 0 to 2 and their non-toxic, pharmaceutical acceptable acid addition salts having excellent antibiotic activity.

4-thia-1-aza-bicyclo�4,2,0!oct-2-ene antibiotics

Novel 1-dethia-2-thia-cephalosporanic acid derivatives of the formula ##STR1## wherein R is selected from the group consisting of ##STR2## Ra is an organic radical, R.sub.i and R.sub.j are individually selected from the group consisting of hydrogen, aliphatic, aromatic and heterocycle or taken together with the nitrogen atom to which they are attached form an optionally substituted cycle or R.sub.b NH--, R.sub.b is optionally substituted carbocyclic or heterocyclic aryl, R.sub.1 and --COM are as defined in the specification, R.sub.4 is hydrogen or methoxy, n.sub.2 is 0, 1 or 2 and their non-toxic, pharmaceutically acceptable acid addition salts in racemic or optically active form having antibiotic activity and their preparation and novel intermediates.

1-dethia-2-thia-cephalosporanic acids

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R is selected from the group consisting of ##STR2## and R.sub.b --NH--, Ra is an organic radical, Ri and Rj are individually selected from the group consisting of hydrogen, aliphatic hydrocarbon, aromatic hydrocarbon and heterocycle or taken together with the nitrogen atom to which they are attached form an optionally substituted ring, Rb is selected from the group consisting of carbocyclic aryl and heterocyclic aryl, both optionally substituted, R.sub.1A is selected from the group consisting of ##STR3## R.sub.A ' and R.sub.B ' are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, Z.sub.A is selected from the group consisting of a simple bond, --O-- and optionally oxidize sulfur, R.sub.3A is selected from the group consisting of optionally substituted carbocyclic aryl and heterocyclic aryl, optionally substitute quaternary ammonium, acetyl, carbamoyl, alkoxycarbonyl, alkyl and haloalkyl of 1 to 4 carbon atoms, --CN and azido, R.sub.4 is selected from the group consisting of hydrogen and methoxy, A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, magnesium, --NH.sub.4, an organic amine and esterified carboxy or --COOA is --COO.sup..crclbar., n.sub.2 is an integer from 0 to 2 and their non-toxic, pharmaceutical acceptable acid addition salts having excellent antibiotic activity.

4-thia-1-aza-bicyclo[4,2,0]oct-2-ene derivatives

A compound selected from the group consisting of a syn isomer of a compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms and cycloalkyl of 3 to 6 carbon atoms, all optionally substituted with at least one member of the group consisting of optionally esterified or salified carboxy, alkoxy carbonyl, carbamoyl, dimethylcarbamoyl, amino, alkylamino, dialkylamino, halogen, alkoxy and alkylthio of 1 to 4 carbon atoms, aryl, heterocyclic aryl, arylthio and heterocyclic arylthio optionally substituted by alkyl of 1 to 4 carbon atoms, R.sub.1 is selected from the group consisting of ##STR2## and A is selected from the group consisting of hydrogen, alkali metal, alkaline earth metal, magnesium, --NH.sub.4 and an organic amine or A is selected from the group consisting of the residue of an easily cleavable ester group or --COOA is --COO-- and the wavy line indicates --CH.sub.2 --R.sub.1 is in the E or Z position and their non-toxic, pharmaceutically acceptable acid addition salts having good antibacterial activity.

Cephalosporins

Novel syn isomers of reacemates and optical isomers of 3-amino-2-oxo-azetidine-1-sulfonic acids of the formula ##STR1## wherein R is difluoromethyl, R.sub.1 is --(CH.sub.2).sub.n --X, n is an integer from 1 to 4, X is selected from the group consisting of halogen, --CN, --OR.sub.1 ', --SR.sub.1 ', azido, thiocyanate, isothiocyanate, and ##STR2## R.sub.1 ' is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.1 ' is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and a heterocycle and R' and R' are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and taken together with the nitrogen to which they are attached form a heterocycle and A.sup.1 is selected from the group consisting of hydrogen, and metal cations and their nontoxic, pharmaceutically acceptable acid addition salts, the wavy line indicating the cis form, trans form or cis trans forms having antibiotic properties.

3-amino-2-oxo-azetidine-1-sulfonic acids

Novel syn isomers of racemates and optical isomers of 3-amino-2-oxo-azetidine-1-sulfonic acids of the formula ##STR1## wherein R is selected from the group consisting of hydrogen linear or branched optionally substituted alkyl of 1 to 12 carbon atoms and optionally substituted alkenyl and alkynyl of 2 to 12 carbon atoms, R.sub.1 is --(CH.sub.2).sub.n --X, n is an integer from 1 to 4, X is selected from the group consisting of halogen, --CN, --OR', --SR.sub.1 ', azido, thiocyanate, isothiocyanate, and ##STR2## is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R' is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and a heterocycle and R' and R' are individiually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and taken together with the nitrogen to which they are attached form a heterocycle and A.sup.1 is selected from the group consisting of hydrogen, and metal cations and their nontoxic, pharmaceutically acceptable acid addition salts, the wavy line indicating the cis form, trans form or cis trans forms having antibiotic properties.

Novel 3-amino-2-oxo-azetidine-1-sulfonic acids

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Chateau-Thierry, France

Alain Bonnet