Abstract: 7.alpha.-Hydroxyamino-7.beta.-[2-substituted-2-(acylamino)acetamido]cephalo sporin antibiotics, pharmaceutically-acceptable salts and in vivo hydrolyzable esters thereof, a method of treating susceptible infections therewith, and intermediates therefor.

Abstract: 7.beta.-Heterocyclicacetylamino-(and 7.beta.-heterocyclicthioacetamido)-3-chloro-3-cephem-4-carboxylic acids and pharmaceutically acceptable salts thereof, e.g., 7.beta.-[2-(2-aminothiazol-4-yl)acetamido]-3-chloro-3-cephem-4-carboxylic acid and salts thereof, exhibit surprising peroral bioavailability and are useful in a method for treating infections in man and animals and in formulations for oral administration.

Abstract: Crystalline adducts of 7-[(Z)-2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido-3-[(1-methyl-1-pyrr olidinium)methyl]-3-cephem-4-carboxylate selected from the group consisting of the di(1-methyl-2-pyrrolidinone) adduct and the di(N-formyl pyrrolidine) adduct and salt complexes thereof have been found to be stable at even high temperatures. The crystalline adducts are prepared by forming an admixture of adducting agents, zwitterions and seed adduct crystals and inducing crystallization followed by isolating the crystals. A process for preparing adduct salt complexes is also disclosed. Crystalline zwitterion can be formed by slurrying the adducts in a solvent which removes the adducting agents.

Abstract: The compounds are of the class of esters of 7-[2-(2-aminothiazol-4-yl-)-2-(syn)methoxyiminoacetamido] cephalosporin derivatives, including lower alkoxymethyl, .alpha.-lower alkoxy-.alpha.-substituted methyl, lower alkylthiomethyl, acyloxymethyl, ethoxycarbonyloxy-1-methylmethyl and .alpha.- acyloxy-.alpha.-substituted methyl esters. The compounds are useful against a broad spectrum of bacteria, particularly gram-negative bacteria, and may be administered in the form of injections, capsules, tablets and granules.

Abstract: A cephalosporin derivative of the formula I: ##STR1## in which X is S, O, CH.sub.2 or SO, R1 is (optionally-substituted)imidazol-2-yl or one of the C-7 acyl groups known in the cephalosporin art, R2 is hydrogen or methoxy, R3 is carboxy or a biodegradable ester thereof and --R4 is of the formula XII, XIII or XIV: ##STR2## in which R32-R40 inclusive are as defined in the specification; and the salts thereof. Pharmaceutical compositions, methods of manufacture and intermediates are also described.

Abstract: A compound having the formula: ##STR1## wherein R.sup.1 is a straight chain, branched chain or cyclic lower alkyl group which may be substituted by a carboxyl group, and each of R.sup.2 and R.sup.3 which may be the same or different, is a hydrogen atom, a hydroxyl group, a methoxy group or an acetoxy group, and R.sup.4 is a hydroxyl group, a methoxy group or an acetoxy group; or a pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof.

Abstract: The presence of a copper salt during the oximation of a .beta.-lactam containing compound having glyoxylamino substituents of the formula ##STR1## by reaction with an aminooxy compound having the formulaH.sub.2 N--O--R.sub.a,or a salt or ester thereof, results in a product wherein the ratio of syn isomer to anti isomer is increased.

Abstract: This invention relates to novel 7-(substituted or unsubstituted amino)-3-substituted methyl-.DELTA..sup.3 -cephem-4-carboxylic acids in which a substituted or unsubstituted 1,2,4-triazolyl or 2-(1,2,3,4-tetrazolyl) group attaches to the exomethylene group at the 3-position of the cephem ring through a carbon-nitrogen bond. These cephalosporins are useful intermediates for producing various novel cephalosporins. Also, this invention concerns a process for producing a compound represented by the formula: ##STR1## which comprises reacting a compound represented by the formula: ##STR2## with an optionally substituted triazole or tetrazole in the presence of an acid or a complex of the acid in an organic solvent at 0.degree. to 80.degree. C.

Abstract: Novel cephem compounds of the formula: ##STR1## wherein R.sup.4 is a residue of a nucleophilic compound selected from hydroxyl, mercapto, cyano, azido, amino, carbamoyloxy, carbamoylthio and thiocarbamoyloxy, said group being unsubstituted or substituted by alkyl of up to three carbons, and R.sup.5 is hydroxyl or lower alkoxy, or a pharmaceutically acceptable ester thereof, have strong antibiotic properties against a wide variety of microorganisms.

Abstract: An anhydrous crystalline, or crystalline hemihydrate, monohydrate or trihydrate of cephalosporin derivative of (6R,7R)-7-[(Z)-2-(2-aminothiazole-4-yl)-2-methoxy-iminoacetoamido]-3(1-qui nuclidiniummethyl)-3-cephem-4-carboxylate. These crystalline materials can maintain outstanding stability for a very long period of time and afford excellent practical uses as pharmaceutical compounds.

Abstract: The invention concerns 7.beta.-amino-cepham-3-one-4-carboxylic acid compounds, particularly esters thereof, and the N-substituted, especially N-acylated derivatives of such compounds. They can be used as intermediates, for example, for the manufacture of the corresponding enol ethers and esters, as well as the corresponding 3-unsubstituted 7.beta.-amino-3-cephem-4-carboxylic acid compounds, which show outstanding pharmacological effects.

Abstract: Compounds of general formula I ##STR1## (wherein R represents NH.sub.2 -- or an acylated or silylated amino group;R.sup.2 represents a hydrogen, halogen, alkyl, aryl, carboxyl or lower alkoxycarbonyl group;R.sup.3 is hydrogen or a carboxyl blocking group;B is >Sor>S.fwdarw.O (.alpha.- or .beta.-); and the dotted line represents .DELTA..sup.2 or .DELTA..sup.3 unsaturation) and salts, solvates and esters thereof are described.Compounds where R.sup.3 is hydrogen, the dotted line represents .DELTA..sup.3 unsaturation and R is a group of formula ##STR2## (where R.sup.a is an optionally substituted heterocyclic aryl group having one or more hetero atoms selected from S, N and O in the ring, R.sup.b is an optionally substituted aryl group, R.sup.c is hydrogen, acyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.d is as defined for R.sup.

Abstract: Process for the preparation of cephem compounds of the formula ##STR1##

Abstract: A compound of the formula; ##STR1## wherein R.sup.0 stands for hydrogen atom, nitrogen-containing heterocyclic group, acyl group or amino-protecting group, Z stands for S, S.fwdarw.O, O or CH.sub.2, R.sup.4 stands for hydrogen atom, methoxy group or formamido group, R.sup.13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted pyrazol-2-yl group forming a fused ring at the 1,5-position or a physiologically or pharmaceutically acceptable salt or ester thereof.This compound is novel and has excellent antibacterial activity.

Abstract: Temperature stable crystalline mono-hydrochloric and sulfuric acid addition salts of 7-amino-3-(1-methylpyrrolidinio)methyl-3-cephem-4-carboxylate substantially free of .DELTA..sup.2 isomer are intermediates for the preparation of broad spectrum 7-[.alpha.-(2-aminothiazol-4-yl)-.alpha.-(Z)-methoxyiminoacetamido]-3-[(1- methyl-1-pyrrolidinio)methyl]-3-cephem-4-carboxylates.

Abstract: This invention relates to a novel aminothiazole intermediate for production of a cephalosporin of antibiotic activity.

Abstract: The compounds according to the invention correspond to the formula: ##STR1## in which: The COOA group at the 4 position is an acid radical, or an alkaline or alkaline-earth salt, or an amino acid or amine salt, for example triethylamine or ethanolamines, or an easily hydrolyzable or metabolically labile and pharmaceutically acceptable ester radical.X denotes an oxygen atom or a sulfur atomn is zero or 1R.sub.1 and R.sub.2 each denote independently hydrogen or a lower alkyl group, preferably a methyl group, orR.sub.1 and R.sub.2 taken together with the carbon atom to which they are linked form a cyclobutyl or cyclopentyl nucleus.B is the residue of a primary or secondary amine.

Abstract: This invention relates to novel compounds of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is carboxy(lower)alkyl or protected carboxy(lower)alkyl,R.sup.2 is carboxy or protected carboxy,R.sup.3 is hydrogen or lower alkyl, andR.sup.4 is lower alkyl, lower alkoxy, acyloxymethyl, lower alkylthiomethyl, lower alkoxymethyl, halogen, lower alkenyl or hydrogen,and pharmaceutically acceptable salts thereof,and processes for making the same.

Abstract: A useful synthetic intermediate, 7-amino-3-acyloxycepham-4-carboxylic acid aralkyl ester, is prepared by reducing 7-amido-3-oxocepham-4-carboxylic acid aralkyl ester with alkali metal borohydride in a dry organic solvent at temperature lower than -20.degree. C. and then acylating the resulting 3-hydroxycepham compound with an acylating reagent to give 3-acyloxycepham compound, and then subjecting the 3-acyloxycepham compound to amide cleavage consisting of treatments (1) with a mixture of phosphorus pentachloride and aromatic base giving imino-chloride and (2) with alcohol for converting the latter into imino-ether and for subjecting the product to alcoholysis giving the objective compound.

Abstract: There is described a process for preparing a sulphoxide of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4, taken individually, are alkyl, alkoxy or aryl groups, X is an alkylene group, R.sup.5 is a carboxylic acid protecting group and Y is a linking group through one or two carbon atoms forming a penam or cephem nucleus, which comprises reacting a compound of formula ##STR2## with an oxidizing agent. .alpha.-Sulphoxide compounds of formula (I) are also provided as novel intermediates.

Abstract: The invention relates to cephem compounds of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is amino or acylamino,R.sup.2 is lower alkyl, andY is CH or N.

Abstract: An antibacterial 7beta-(carboxyalkenoyl)amino-3-cephem-4-carboxylic acid represented by the following formula: ##STR1## (wherein R is aryl or a heterocyclic group;R.sup.1 is hydrogen or halogen;R.sup.2 is a single bond, alkylene, or thiaalkylene;R.sup.3 is a hydrogen atom or carboxy modifying group;R.sup.4 is hydrogen or methoxy;R.sup.5 is hydrogen or a 3-substituent of cephalosporins;R.sup.6 is a hydrogen atom or carboxy modifying group; andX is oxygen, sulfur, or sulfinyl)a pharmaceutical composition containing the same, and a method for treating a bacterial infection with the same.

Abstract: Novel .beta.-lactam antibiotics of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3, which may be identical or different, denote a substituted or unsubstituted alkyl radical or a monocyclic or bicyclic, optionally substituted, carbocyclic or heterocyclic ring, orR.sup.1 represents an optionally substituted alkyl radical or a monocyclic or bicyclic, substituted or unsubstituted, carbocyclic or heterocyclic ring, andR.sup.2 and R.sup.3, together with the N.sup..sym. atom, form an optionally substituted monocyclic or polycyclic ring which can be saturated or unsaturated and can contain oxygen, sulphur and nitrogen as other hetero atoms, orR.sup.1, R.sup.2 and R.sup.3, together with the N.sup..sym. atom, form a bridged, optionally substituted polycyclic ring which can be saturated or unsaturated and can contain oxygen, sulphur and nitrogen as other hetero atoms, andR.sup.

Abstract: The invention relates to novel halovinyl cephem derivatives of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is a group of the formula:R.sup.4 --A--CONH--in which R.sup.4 is cyano(lower)alkenylthio or a group of the formula: ##STR2## in which R.sup.6 is hydrogen, amino or a protected amino group, andA is carbonyl, lower alkylene, hydroxy(lower)alkylene or a group of the formula: ##STR3## in which R.sup.5 is hydrogen, carboxy(lower)alkyl or protected carboxy(lower)alkyl;R.sup.2 is carboxy or a protected carboxy group; andX is halogen, and pharmaceutically acceptable salts thereof.

Abstract: This invention provides a process for preparing 3-exomethylenecepham derivatives represented by the formula ##STR1## wherein R.sup.1 is arylacetylamino, aryloxyacetylamino, heterocyclic acetylamino or imido, and R.sup.2 is a protective group for the carboxyl, the process being characterized in that a 3-halomethylcephem compound represented by the formula ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, and X is a halogen atom is electrolyzed in a mixture of a hydrophilic organic solvent and water.

Abstract: The invention relates to novel compounds of the formula: ##STR1## where R=4-chlorophenylmethyl or 2,6-dichlorophenylmethyl or an alkalimetal salt thereof.The compounds have utility as antibiotics.

Abstract: Novel antibacterially active cephalosporins of the formula ##STR1## in which R.sup.1 denotes hydrogen, optionally substituted alkyl, a substituted or unsubstituted phenyl ring, a polycyclic aromatic ring or an optionally substituted heterocyclic 5- or 6-member ring having 1-4 heteroatoms,R.sup.2 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkenyl, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, hydroxymethyl, formyloxymethyl, C.sub.1 -C.sub.4 -alkylcarbonyloxymethyl, aminocarbonyloxymethyl, pyridiniummethyl, 4-carbamoylpyridiniummethyl, 4-sulphonylethylpyridiniummethyl, 4-carboxylmethylpyridiniummethyl or heterocyclylthiomethyl, heterocyclyl representing a radical of the formula ##STR2## wherein R.sup.8 denotes hydrogen, methyl, 2-dimethylaminoethyl, carboxymethyl, sulphomethyl, carboxyethyl or sulphoethyl andR.sup.9 denotes hydrogen or methyl,or pharmaceutically tolerated salts or esters thereof.

Abstract: New 3-vinylcephalosporins of the general formula (I), ##STR1## in which n=0 or 1, R.sub.1 is a radical of the general formula (II), ##STR2## in which R.sub.4 is hydrogen or a protective radical and R.sub.5 represents a radical of the general formula (IIa) ##STR3## in which R.sup.a.sub.5 and R.sup.b.sub.5 are hydrogen or alkyl or together form an alkylene radical and R.sup.c.sub.5 is hydrogen or a protective radical, R.sub.2 is hydrogen, a protective radical or a radical which can easily be removed by an enzymatic method, and R.sub.3 is a halogen atom or a radical R'.sub.3 SO.sub.2 O-- or R".sub.3 CO--O--, in which radicals R'.sub.3 and R".sub.3 are substituted or unsubstituted alkyl or phenyl radicals, or alternatively R.sub.1 is a hydrogen atom or a radical of the general formula (II) in which R.sub.4 is defined as above and R.sub.5 is hydrogen, alkyl, vinyl, cyanomethyl or a protective radical, and R.sub.2 is defined as above, or R.sub.1 is hydrogen or a variously substituted acyl radical and R.sub.

Abstract: In accordance with this invention, it has been found that the oxygen analog of 7-amino-cephalosporanic acid and biologically active derivatives thereof can be formed from esters of 7-amino-cephalosporanic acid. Esters of 7-oxocephalosporanic acid can be formed by diazotization of an ester or 7-amino-cephalosporanic acid and contact of the diazo compound so formed with a hypohalous acid and a base in a water miscible organic solvent. Oxygen analogs of 7-aminocephalosporins isolated as esters are then formed by reducing the aforesaid ester to the corresponding 7.beta.-hydroxy-cephalosporanate and then forming the desired analog by introduction of a side chain via hydroxyl group modification. Oxygen analogs of 7-amino-cephalosporins are then formed by regeneration of the acid via protective group removal.

Abstract: The invention relates to antibiotic compounds of the formula: ##STR1## wherein R.sup.1 represents a hydrogen atom or a carboxyl-protecting group; R.sup.2 represents a group of the formula: ##STR2## R.sup.3 represents a hydrogen atom or an alkoxy group; R.sup.4 represents a hydrogen atom or a halogen atom; R.sup.5 represents a hydrogen atom or a protected or unprotected amino group; A represents a group of the formula, --CH.sub.2 -- or a group of the formula, ##STR3## or a group of the formula, ##STR4## and the bond means that the compound may be a synisomer or an anti-isomer or a mixture thereof.

Abstract: Novel cephalosporin compounds having antibacterial activity, which are represented by the following compounds of the general formula (I), ##STR1## wherein R.sub.1 represents an amino group or a protected amino group;.circle.A represents a 5- or 6-membered heterocyclic ring containing therein 1 to 4 nitrogen, oxygen or sulfur atoms;R.sub.2 represents a normal alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms; a cycloalkenyl group having 3 to 6 carbon atoms; an aromatic organic residue; a 3- to 6-membered heterocyclic ring containing 1 to 4 nitrogen, sulfur or oxygen atoms or, ##STR2## wherein Ra and Rb each, which may be the same or different, represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;R.sub.

Abstract: Ceftazidime pentahydrate in crystalline form is provided in a one-step process comprising acidic removal of protecting groups from an amino-protected and carboxy-protected ceftazidime, separation of aqueous phase after addition of a water-immiscible organic solvent, and precipitation of pentahydrate by adjusting pH of aqueous phase from about 3.5 to about 4.5.

Abstract: A process for the preparation of a 7-acylamino-3-hydroxy-2-cephem-4-carboxylic acid, 7-acylamino-3-hydroxy-1-dethia-1-oxa-3-cephem-4-carboxylic acid or derivative thereof of the general formula ##STR1## in which R.sup.1 is hydrogen or optionally substituted alkyl, alkenyl, alkinyl, aralkyl, aryl, heteroaryl, heteroaralkyl, aryloxyalkyl, heteroaryloxyalkyl, alkoxyalkyl, arylthioalkyl, heteroarylthioalkyl, alkylthioalkyl, alkoxy, aryloxy, alkylthio or arylthio,R.sup.2 is hydrogen, a carboxy-protective group or a pharmaceutically useful ester radical, andX is sulphur or oxygen,which comprises:(a) reacting a compound of the formula ##STR2## with (i) a compound of the formula ##STR3## in which R.sup.2 and X have the abovementioned meaning and Y represents diazo (N.sub.2) or hydrogen (H.sub.2) in an inert solvent in the presence of a Lewis acid or proton acid catalyst, or(ii) a compound of the formulaHX--CH.sub.2 --C.tbd.C--COOR.sup.

Abstract: This invention relates to a novel process for producing a useful cephalosporin which comprises reacting a thiolo ester compound with a 7-aminocephalosporin in the presence of boron trifluoride or a complex compound thereof. This process enables the cephalosporin to be produced with a high purity in a high yield.

Abstract: The invention relates to novel cephem compounds of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is amino, lower alkanoylamino, ar(lower)alkanoylamino, amino- or alkanoylaminothiazolyl(lower)alkanoylamino having a lower alkoxyimino, amino- or alkanoylaminothiazolyl(lower)alkanoylamino an ar(lower)alkoxycarbonyl(lower)alkoxyamino, aminothiazolyl(lower)alkanoylamino having a carboxy(lower)alkoxyamino, or aminothiadiazolyl(lower)alkanoylamino having a lower alkoxyimino,R.sup.2 is 2,2,-dihalovinyl or ethynyl, andR.sup.3 is carboxy or protected carboxy, andpharmaceutically acceptable salts thereof.

Abstract: Crystalline cephem-acid addition salts of the formula ##STR1## and their hydrates, processes for the preparation of the acid addition salts, pharmaceutical products containing these compounds and processes for their preparation, and the use of the compounds for combating bacterial infections.

Abstract: 1. A cephalosporin derivatives of the general formula ##STR1## wherein R.sup.1 is an .alpha.-, .beta.- or .gamma.-amino acid residue (bonded by the ester linkage), which may optionally be substituted by one or two lower alkyl groups at the amino group thereof, R.sup.2 is an 1-alkanoyloxyalkyl, 1-alkoxycarbonyloxyalkyl, phthalidyl or 5-methyl-1,3-dioxolen-2-on-4-ylmethyl group, R.sup.3 is a carbamoyloxymethyl group, which may optionally be substituted by one or two lower alkyl groups, or a heterocyclothiomethyl group, which may optionally be substituted by one or more appropriate substituents, and R.sup.4 is a hydrogen atom or a hydroxy group, or its non-toxic salt are found to be useful as orally administrable antibiotics having broad antimicrobial activities against both gram-positive and gram-negative bacteria.

Abstract: 7-substituted 3-cephem or cepham compounds characterized by the grouping, in the 7-position thereof, of the formula:R'--A--CONH--where R' is thiadiazolyl or amino thiazolyl, and A is methylene carrying oxyiimino, or R' is haloacetyl and A may also be methylene, their preparation, and pharmaceutical uses.

Abstract: 3-(alkynylalkyloxy)cephalosporin antibiotics and the intermediates therefor are disclosed. Pharmaceutical compositions for the antibiotics are also disclosed.