Rhone-Poulenc Sante

Rhone-Poulenc Industries

Rhone-Poulenc Rorer S.a.

Bernard Plau

Daniel Farge

Claude Moutonnier

Jean-Francois Peyronel

Claude Guyon

Pierre Le Roy

Gerard Taurand

Claude Garret

Pierre L Roy

Christian Berger

New phenothiazine derivatives of general formula (I) in which

Phenothiazine derivatives, their preparation and pharmaceutical

Phenothiazine derivatives of general formula (I), in which R is a linear or branched (1 to 6 C) alkyl radical and R.sub.1 and R.sub.2, which may be identical or different, are linear or branched (1 to 4 C) alkyl radicals or form, with the nitrogen atom to which they are attached, a 4- to 7-membered heterocycle, their isomeric forms and mixtures thereof as well as their addition salts with acids, possess analgesic and diuretic activity. ##STR1##

Analgesic phenothiazine derivatives

Phenothiazine derivatives of formula: ##STR1## in which Y is hydrogen or halogen, R.sub.1 and R.sub.2, which may be identical or different, denote alkyl, cycloalkyl-alkyl, hydroxyalkyl or acetyloxyalkyl radicals or form, together with the nitrogen atom to which they are attached, an optionally substituted, saturated or partially unsaturated 4- to 7-membered heterocycle; and either X is oxygen, sulphur or: N-R.sub.4, R is cycloalkyl, phenyl or --CH.sub.2 R.sub.3, R.sub.3 is H, alkyl (1 to 5 C), alkenyl or alkynyl (2 to 4 C), cycloalkyl (3 to 6 C), phenyl, substituted phenyl or a heterocyclic radical, R.sub.4 is H or --CN, except that X is not oxygen if, simultaneously, R.sub.3 is H or alkyl, R.sub.1 and R.sub.2 are alkyl or NR.sub.1 R.sub.2 forms an unsubstituted heterocycle, and Y is H; or X is: N-R.sub.4 and R.sub.4 forms, with R and the neighbouring atoms, an optionally substituted imidazolyl or imidazolinyl radical or a hexahydrobenzimidazolyl radical, in their isomeric forms and mixtures thereof and their acid addition salts are useful as analgesics and diuretics.

Phenothiazine derivatives of formula ##STR1## in which R represents --NR.sub.1 R.sub.2 in which R.sub.1 and R.sub.2, which may be identical or different, are alkyl, hydroxyalkyl or acetyloxyalkyl radicals, or form, together with the nitrogen atom to which they are attached, a heterocycle containing 4 to 7 members which may be substituted by 1 or 2 alkyl, hydroxyalkyl or acetyloxyalkyl radicals, or R represents --N.sup.+ R.sub.1 R.sub.2 R.sub.3 in which R.sub.1 and R.sub.2 are as defined above and R.sub.3 is alkyl or phenylalkyl, their isomeric forms and their mixtures, and their salts, are useful in the field of antidiarrhetics.

Derivatives of phenothiazine and the compositions which contain them

New cephalosporin derivatives of the formula: ##STR1## in which R is an amino-protecting radical, R' is a protected carboxyl radical, Hal is a halogen atom, R.sub.a, R.sub.b and R.sub.c are hydrogen atoms, or R.sub.a is a protected carboxyl radical and R.sub.b and R.sub.c, which are identical or different, are hydrogen atoms, or C.sub.1 -C.sub.4 alkyl radicals, or together form a C.sub.2 -C.sub.5 alkylene radical, and n=0 or 1, their isomeric forms and mixtures thereof, are useful for the preparation of cephalosporins which have antibacterial properties.

3-(1-Halo-2-oxoethyl)cephalosporin intermediates

New cephalosporin derivatives of the formula: ##STR1## in which R' represents a protected carboxyl radical, Hal represents a halogen atom, X.sub.1 represents a sulphur or oxygen atom or a sulphinyl radical and R represents an acyl radical or an amine-protecting radical, are useful as intermediates for the preparation of cephalosporins having antibacterial activity.

Cephalosporin derivatives

Cephalosporin derivatives of the formula: ##STR1## in which A is a single bond or a radical --CH.sub.2 --, --NH-- or --NHCO--, attached to the 3-position or 4-position of the pyridinio radical, R is a methyl, carboxymethyl, carbamoylmethyl, benzyl or allyl radical, R.sub.a, R.sub.b and R.sub.c are hydrogen atoms, or alternatively R.sub.a is carboxyl and R.sub.b and R.sub.c, which are identical or different, are hydrogen atoms or alkyl radicals, or together form an alkylene radical, and n equals 0 or 1, in their syn form, and also their addition salts with acids, metal salts and addition salts with nitrogen-containing bases are antibacterial agents having a broad spectrum of activity.

Cephalosporin derivatives, their preparation and compositions containing

New cephalosporin derivatives, of the formula: ##STR1## in which R.sub.1 is a heterocyclic, phenyl, p-hydroxyphenyl, phenoxy or dichlorophenylthio radical and R.sub.2 is a hydrogen atom, or R.sub.1 is phenyl or p-hydroxyphenyl and R.sub.2 is an amino radical, R.sub.3 is hydrogen, phenyl, substituted phenyl, alkylthio or substituted amino or a radical of the structure --A--R'.sub.3, which A is --CH.sub.2 --, --NH-- or --NHCO-- and R'.sub.3 is a substituted pyridinio radical, R is a carboxyl radical or a carboxylato radical if R.sub.3 is a --AR'.sub.3 radical and X is a sulphur or oxygen atom, the said alkyl moieties or radicals containing 1 to 4 carbon atoms each in their D, L and D,L forms, where these exist, and their salts are narrow-spectrum anti-bacterial agents which are active against gram-positive bacteria.

Cephalosporin derivatives, and pharmaceutical compositions containing

New oxacephalosporins of the general formula (I), in which R is optionally N-oxidised pyridyl, pyrimidin-2-yl, substituted pyridazin-3-yl, 5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 4-position, substituted 1-alkyl-1,3,4-triazol-5-yl or 1,2,4-triazol-5-yl, 5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 1-position, 5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl substituted in the 2-position, substituted or unsubstituted 2-alkyl-2,5-dihydro-5-oxo-1,2,4-triazin-3-yl, 1-amino-1,2-dihydro-2-oxo-pyrimidin-4-yl, substituted 1,3,4-thiadiazol-5-yl or tetrazol-5-yl substituted in the 1-position, R' is a substituted 2-(2-aminothiazol-4-yl)-acetyl radical or an .alpha.-carboxyarylacetyl radical and R' is a hydrogen atom or a methoxy radical in the 7.alpha.-position, and also their salts, their preparation and the medicaments in which they are present. ##STR1##

Oxacephalosporins and anti-bacterial composition containing same

New oxacephalosporins of the general formula: ##STR1## in which either R.sub.1 is hydrogen or a protective radical, R.sub.4 is hydrogen or substituted 2-(2-aminothiazol-4-yl)-acetyl or .alpha.-carboxyarylacetyl, of which the amine and acid groups are free or protected, and R' is hydrogen or methoxy in the 7.alpha.-position, or R.sub.1 is a protective radical, R.sub.4 is a radical which can easily be removed and R' is hydrogen or methoxy in the 7.alpha.-position or hydrogen in the 7.beta.-position, and R.sub.2 is a radical --O SO.sub.2 --R.sub.3 or --O CO--R'.sub.3 (R.sub.3 and R'.sub.3 being substituted or unsubstituted alkyl radicals, or phenyl radicals) or a halogen atom, are useful as intermediates for the preparation of antimicrobial oxacephalosporins.

Oxacephalosporins

New oxacephalosporin derivative of the general formula: ##STR1## in which R.sub.1 is a protective radical, R.sub.2 is either a radical of the general formula: ##STR2## [in which R.sub.5 is hydrogen, alkyl, vinyl, protected carboxyalkyl or a protective radical and R.sub.6 is a protective radical] or an .alpha.-carboxyarylacetyl radical and R' is hydrogen or methoxy in the 7.alpha.-position, or alternatively R.sub.2 is a protective radical and R' is either hydrogen or methoxy in the 7.alpha.-position or hydrogen in the 7.beta.-position, and R.sub.3 and R.sub.4 are optionally substituted alkyl, or phenyl, or form a heterocyclic ring with the nitrogen atom, their E and Z forms and mixtures thereof and also their preparation. These new products are useful as intermediates for the preparation of biologically active oxacephalosporins.

New oxacephalosporins of the general formula ##STR1## in which R.sub.1 is a protective radical and (a) R.sub.4 is a substituted 2-(2-aminothiazol-4-yl)-acetyl radical of which the amine group is protected, or an .alpha.-carboxyarylacetyl radical, and R' is hydrogen or methoxy in the 7.alpha.-position, or alternatively

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Creteil, France

Bernard Plau