Abstract: There are described compounds of the formula ##STR1## in which R signifies lower alkoxycarbonyl, lower alkoxycarbonylamino, the acyl residue of an .alpha.- or .beta.-amino acid or a residue of the general formulaQ--X--Y-- (a)wherein Q signifies a 3- to 6-membered ring which optionally contains nitrogen, sulphur and/or oxygen and which is optionally bonded with a fused ring, X signifies a direct bond or a linear "spacer" with up to 6 atoms consisting of carbon, nitrogen, oxygen and/or sulphur, of which up to 2 atoms can be nitrogen atoms and 1 atom can be oxygen or sulphur, and Y represents one of the groups --CO--, --CS--, --CONH-- and (where X contains neither sulphur nor carbonyl as a terminal component) --SO.sub.2 --;and in which R.sup.1 signifies hydrogen, halogen, carbamoyloxy, lower alkanoyloxy or a group of the formula --S--Het, wherein Het represents a 5- or 6-membered heteroaromatic group containing nitrogen, sulphur and/or oxygen, and R.sup.2 represents the sulpho group --SO.sub.3 H or R.sup.

Abstract: Compounds of the formula ##STR1## where Z, A, and R are as disclosed herein and pharmaceutically compatible, readily hydrolyzable esters and salts of these compounds are disclosed.The compounds have .beta.-lactamase inhibiting properties and are useful in the control of .beta.-lactamase-forming pathogens in combination with .beta.-lactam antibiotics. They also exhibit antibacterial activity of their own and can accordingly be used themselves in the control or treatment of infectious diseases.

Abstract: Compounds of the formula ##STR1## where Z, A, and R are as disclosed herein and pharmaceutically compatible, readily hydrolyzable esters and salts of these compounds are disclosed.The compounds have .beta.-lactamase inhibiting properties and are useful in the control of .beta.-lactamase-forming pathogens in combination with .beta.-lactam antibiotics. They also exhibit antibacterial activity of their own and can accordingly be used themselves in the control or treatment of infectious diseases.

Abstract: 7.beta.-Amino-3-hydroxy-1-carba(1-dethia)-3-cephem-4-carboxylic acid esters are provided via cyclization of cis-3-(substituted amino)-1-(2-substituted 2-oxoethyl)-4-substituted azetidinones. The 7.beta.-amino-3-hydroxy-1-carba(1-dethia)-3-cephem-4-carboxylic acid esters are useful chiral intermediates to .beta.-lactam antibiotics.

Abstract: Antimicrobial quinolonyl lactam esters comprising a lactam-containing moiety linked, by an ester group, to the 3-carboxy group of a quinolone moiety. These compounds are of the formula: ##STR1## wherein (1) R.sup.3, R.sup.4, and R.sup.5, together with bonds "a" and "b", form certain lactam-containing moieties similar to those known in the art to have antimicrobial activity; and(2) A, R.sup.6, R.sup.7, and R.sup.8 form any of a variety of quinolone or napthyridine structures similar to those known in the art to have antimicrobial activity.

Abstract: 3-Fluorosulfonyloxyceph-3-ems having a protected amino or acylamino group in the 7-position are subject to carbon-carbon bond formation at the 3-position by means of a palladium catalyzed coupling reaction with substituted organostannanes. A process for preparing cefprozil is disclosed.

Abstract: Disclosed is a process for preparing a .beta.-lactam compound represented by the formula: ##STR1## wherein R.sup.1 represents a hydroxy-substituted lower alkyl group or an amino group each of which may be protected; R.sup.2 represents hydrogen atom or an ester residue; X represents a methylene group which may be substituted by a lower alkyl group, sulfur atom or a group represented by the formula: --A--CH.sub.2 -- where A represents sulfur atom, oxygen atom or methylene group; and W represents an active ester residue of hydroxyl group, or a salt thereof, which comprises the steps of treating a 1-aza-3-thia-bicycloalkane compound represented by the formula: ##STR2## wherein R.sup.1, R.sup.2 and X have the same meanings as defined above, or a salt thereof with a base in the presence of a desulfurizing agent and then reacting the resulting compound with an active esterifying agent of hydroxyl group.

Abstract: The invention provides complexes of the formula: ##STR1## wherein X is chloro, hydrogen, vinyl, or --CH.sub.3,Z is O;is 0-5;Y is phenyl or 1,4-cyclohexadien-1-yl;R.sub.1 and R.sub.2 are hydrogen or hydroxy, with the proviso that R.sub.1 and R.sub.2 are not both hydrogen andR.sub.3 is --COO.sup.-, --COO(C.sub.1 -C.sub.4 alkyl), --NO.sub.2 or ##STR2## wherein R.sub.4 is C.sub.1 -C.sub.4 alkyl.

Abstract: The invention is directed to the crystalline isopropyl alcohol solvate of loracarbef, and also is directed to a process for the preparation of the crystalline monohydrate form of the compound of formula (I) ##STR1## which includes exposing the crystalline isopropyl solvate form of the compound of formula (I) to a temperature of between about 50.degree. and 90.degree. C. and a relative humidity of between about 60 to about 100%.

Abstract: A method for preparing 2-amino-.beta.-lactams which are substituted by readily-removed protecting groups is provided. According to this invention, an acyl-2-amino-.beta.-lactam is further acylated with a different acyl group and is subsequently treated with base to provide a protected 2-amino .beta.-lactam with a more desirable protecting group.

Abstract: A method for preparing a new class of protected amino intermediates is provided which utilizes reaction of an imido protected primary amine with a secondary amine. The intermediates thus provided are suitably protected for nucleophilic functionalization on the residue of the primary amine. The desired imido protected amine thus derivatized may be regenerated using acid. Further provided are methods for resolving racemic primary amines. Also provided are .beta.-lactam intermediates protected with the new amino protecting group which are useful in the preparation of .beta.-lactam antibiotics.

Abstract: A process for the preparation of the crystalline monohydrate form of the compound of formula (I) ##STR1## which includes exposing the crystalline dihydrate form of the compound of formula (I) to a temperature of between about 50.degree. and 65.degree. C. and a relative humidity of between about 60 to about 100%.

Abstract: A compound of the formula I: ##STR1## wherein Acyl is C.sub.1 -C.sub.12 acyl; Het is an optionally substituted monocyclic heteroaromatic group containing one or more hetero atoms; R.sup.1 is a single bond or C.sub.1 -C.sub.4 alkylene; R.sup.2 is a straight or branched C.sub.1 -C.sub.4 alkylene; and Y is a hydrogen atom or methoxy group, or a pharmaceutically acceptable salt or an amino-, carboxy- and/or hydroxy-protected derivative thereof, which have a potent antibiotic activity.

Abstract: The invention provides a process for the preparation of the crystalline monohydrate form of the compound of the formula (I) ##STR1## which comprises the step of mixing a form of loracarbef, other than the crystalline monohydrate, such as the ethanol crystal, acetone crystal, crystalline dihydrate, acetonitrile crystal, methanol crystal, propanol crystal, ethyl acetate crystal, methylene chloride crystal, crystalline bis(DMF) and crystalline mono(DMF) form, in water at a temperature between about 30.degree. C. to about 60.degree. C., and preferably at a temperature between 40.degree. C. and 50.degree. C. Conversion may also be accomplished by exposing the loracarbef form to saturated steam at a temperature of between about 90.degree. to about 100.degree. C. Another aspect of the invention is the preparation of the above mentioned crystal forms by slurrying the bis(DMF) solvate form of the compound of formula (I) with the respective solvent.

Abstract: The present invention provides a novel ester cleavage process for use with .beta.-lactams. The process is useful because of mild conditions necessary to complete the reaction, such conditions being especially suitable for .beta.-lactams.

Abstract: Antimicrobial quinolnyl lactam esters comprising a lactam-containing moiety linked, by an ester group, to the 3-carboxy group of a quinolone moiety. These compounds are of the formula: ##STR1## wherein (1) R.sup.3, R.sup.4, and R.sup.5, together with bonds "a" and "b", form certain lactam-containing moieties similar to those known in the art to have antimicrobial activity; and(2) A, R.sup.6, R.sup.7, and R.sup.8 form any of a variety of quinolone or napthyridine structures similar to those known in the art to have antimicrobial activity.

Abstract: 1-Carba(1-dethia)cephem antibacterial agents possessing a 3-(substituted or unsubstituted)thiazolo group are provided. Further provided is a method for treating bacterial infections in man and other animals and a pharmaceutical formulation utilizing said 1-carba(1-dethia)cephems.

Abstract: Provided is a process for diastereoselectively preparing compounds of the formula ##STR1## which includes the step of subjecting a compound of the formula ##STR2## to a salt whose anion is a nucleophilic base whose conjugate acid has a pKa in the range of between about -7 to about 14, or a silylated derivative of the salt; whereinR.sub.1 is said nucleophile;R is hydrogen, or protected amino,R.sub.2 is R.sub.4 as defined herein below;R.sub.3 is a leaving group; andR.sub.4 is hydrogen, C.sub.1 -C.sub.6 alkyl, or a group of the formula--CH.sub.2 --CH.sub.2 --R.sub.6whereinR.sub.6 is 2-furyl, naphthyl, phenyl, phenyl substituted with 1, 2 or 3 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, nitro, halo, carboxy and amido; orR.sub.6 is a group of the formula--COOR.sub.7or--COSR.sub.7in whichR.sub.7 is selected from C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, benzyl, phenyl, or benzyl or phenyl substituted with 1, 2 or 3 substituents selected from C.sub.

Abstract: .beta.-Lactam compounds of the formula (Ia) including pharmaceutically acceptable salts and in vivo hydrolysable esters, processes for their preparation and their use as antibiotics: ##STR1## wherein R.sup.1 is hydrogen, methoxy or formamido;R.sup.2 is an acyl group, in particular that of an antibacterially active cephalosporin;CO.sub.2 R.sup.6 is a carboxy group or a carboxylate anion;R.sup.3 is a Y-lactone ring optionally containing an endocyclic double bond, which ring is optionally substituted at any carbon atom by alkyl, dialkylamino, alkoxy, hydroxy, halogen or aryl, which in the case of more than one substituent may be the same or different, or is optionally di-substituted at two adjacent carbon atoms, which are available for substitution, to form an aromatic fused bicyclic system; and X is S, SO, SO.sub.2, O or CH.sub.2.

Abstract: A compound of formula I ##STR1## wherein X is sulfur or CH.sub.2 ;R.sup.1 is hydrogen, hydroxy, amino, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, phenyl optionally substituted with one to three C.sub.1-6 alkyl, C.sub.1-6 alkyloxy or hydroxy, C.sub.1-6 alkylthio, phenylthio optionally substituted with one to three C.sub.1-6 alkyl or C.sub.1-6 alkyloxy on the phenyl ring, phenylmethyloxy optionally substituted with one to three C.sub.1-6 alkyl or C.sub.1-6 alkyloxy on the phenyl ring, 1-morpholino, C.sub.1-6 alkyloxy, C.sub.2-6 alkenylmethyloxy, C.sub.3-6 alkynylmethyloxy, C.sub.1-6 alkylamino, C.sub.1-6 dialkylamino or a radical selected from the group consisting of ##STR2## in which n is 0 to 3, R.sup.5 is C.sub.1-6 alkyl or hydrogen, and R.sup.3 and R.sup.4 are independently C.sub.1-6 alkyl;R.sup.2 is hydrogen, a conventional amino protecting group or an acyl group;R.sup.0 is hydrogen or a conventional carboxy protecting group, or --CO.sub.2 R.sup.

Abstract: Antimicrobial quinolonyl lactam esters comprising a lactam-containing moiety linked, by an ester group, to the 3-carboxy group of a quinolone moiety. These compounds are of the formula: ##STR1## wherein (1) R.sup.3, R.sup.4, and R.sup.5, together with bonds "a" and "b", form certain lactam-containing moieties similar to those known in the art to have antimicrobial activity; and(2) A.sup.2, A.sup.2, A.sup.3, R.sup.7, R.sup.8, and R.sup.9 form any of a variety of quinolone or naphthyridine structures similar to those known in the art to have antimicrobial activity.

Abstract: 1-Carba(1-dethia)cephem antibacterial agents possessing a 3-(substituted or unsubstituted)thiazolo group are provided. Further provided is a method for treating bacterial infections in man and other animals and a pharmaceutical formulation utilziing said 1-carba(1-dethia)cephems.

Abstract: The present invention provides a process for protecting an amino group in a compound exposed to nucleophilic reaction conditions in which the imido group used for protection is reacted with a secondary amine to form an acyl group which protects the amino group during exposure to the nucleophilic reaction conditions, after which the acylamino group may be reacted with an acid to reform the imido group so that the compound may then undergo non-nucleophilic manipulations. Also provided is a resolution method in which diasteriometric compounds having the acylamino group as described above are reacted with acid, and as these diasteriomers react at different rates to form the imido group, the reaction may be monitored so as to isolate the desired product at the appropriate point to maximize optical purity.

Abstract: A compound for formula I ##STR1## wherein X is sulfur or CH.sub.2 ;R.sup.1 is hydrogen, hydroxy, amino, C.sub.1-6 alkyl, C.sub.2-5 alkenyl, C.sub.2-6 alkynyl, phenyl optionally substituted with one to three C.sub.1-6 alkyl, C.sub.1-6 alkyloxy or hydroxy, C.sub.1-6 alkylthio, phenylthio optionally substituted with one to three C.sub.1-6 alkyl or C.sub.1-6 alkyloxy on the phenyl ring, phenylmethyloxy optionally substituted with one to three C.sub.1-6 alkyl or C.sub.1-6 alkyloxy on the phenyl ring, 1-morpholino, C.sub.1-6 alkyloxy, C.sub.2-6 alkenylmethyloxy, C.sub.3-6 alkynylmethyloxy, C.sub.1-6 alkylamino, C.sub.1-6 dialkylamino or a radical selected from the group consisting of ##STR2## in which n is 0 to 3, R.sup.5 is C.sub.1-6 alkyl or hydrogen, and R.sup.3 and R.sup.4 are independently C.sub.1-6 alkyl;R.sup.2 is hydrogen, a conventional amino protecting group or an acyl group;R.sup.0 is hydrogen or a conventional carboxy protecting group, or --CO.sub.2 R.sup.

Abstract: .beta.-Lactam compounds of the formula (I) including pharmaceutically acceptable salts and in vivo hydrolysable esters, processes for their preparation and their use as antibiotics: ##STR1## wherein R.sup.1 is hydrogen, methoxy or formamido;R.sup.2 is an acyl group, in particular that of an antibacterially active cephalosporin;R.sup.3 is hydrogen or a readily removable carboxy protecting group (such as a pharmaceutically acceptable in-vivo hydrolysable ester group);R.sup.4 is a .gamma.- or .delta.-lactone ring optionally containing one or (where applicable) two endocyclic double bonds, which ring is optionally substituted at any carbon atom by alkyl, dialkylamino, alkoxy, hydroxy, halogen or aryl, which in the case of more than one substituent may be the same or different, or is optionally di-substituted at two adjacent carbon atoms, which are available for substitution, to form an aromatic fused bicyclic system; x and y are independently 0 or 1; X is S, SO, SO.sub.2, O or CH.sub.2 ; and Y is O or S.

Abstract: A method for preparing 2-amino-.beta.-lactams which are substituted by readily-removed protecting groups is provided. According to this invention, an acyl-2-amino-.beta.-lactam is further acylated with a different acyl group and is subsequently treated with base to provide a protected 2-amino .beta.-lactam with a more desirable protecting group.

Abstract: Cephalosporin and 1-carba(1-dethia)cephalosporin antibiotics substituted in the 3-position with, inter alia, alkyl, alkenyl and alkynyl, are provided via process comprising conversion of a cephalosporin or 1-carba(1-dethia)-3-cephem substituted in the 3-position with halogen or a sulfonyloxy ester with Pd(O) mediated alkylation with organostannanes.

Abstract: Cephalosporin antibiotics having a 3-position substituent of the formula: ##STR1## are described; wherein R.sup.1 is hydrogen or certain substituted alkyl groups, Z is CH or N, R.sup.2 and R.sup.3 are hydroxy or in vivo hydrolysable esters thereof, (R.sup.12).sub.n represents various optional substituents and X=Y is an olefin, oxime, azo or related group. Processes for their preparation and use are described.

Abstract: The invention provides novel compounds of the formula ##STR1## wherein R is a protected amino group and R1 is a carboxy protected group.

Abstract: 7-.beta.-Acylamino-1-carba-(1-dethia)-3-trifluoromethyl-3-cephem-4-carboxyl ic acids and derivatives are provided as antibiotics. Pharmaceutical formulations comprising the antibiotics, intermediates, and a process for their preparation are also provided.

Abstract: Superior method for the removal of the methyl or ethyl ester group from cephalosporin and carbacephalosporin carboxylic acids.

Abstract: The crystalline monohydrate, mono (N,N'-dimethylformamide) and bis(N,N'-dimethylformamide) solvates of 7.beta.-[2'-(R)-2'-(p-hydroxyphenyl-2'-amino-acetamido]-3-chloro-3-(1-carb adethiacephem)-4-carboxylic acid ("LY213735") are novel compounds with superior physical characteristics. Also described are pharmaceutical formulations of crystalline LY213735 monohydrate.

Abstract: The invention provides a process for preparing 7-protected amino-4-protected carboxy-1-carbacephalosporins which includes subjecting a 3-protected-amino-4-(1-propylene oxide)-methyl(protected carboxy)-azetidin-2-one to a strong base to form a 2-hydroxycepham and thereafter dehydrating the 2-hydroxycepham to form the desired 1-carbacephalosporin.

Abstract: This invention provides novel 3-phosphine oxide substituted 1-carba(1-dethia)cephalosporins useful as anti-microbial agents, and formulations and methods of use thereof.

Abstract: The present invention provides compounds of the formula ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, or C.sub.1 -C.sub.6 haloalkyl;A and A' are independently hydrogen, C.sub.1 -C.sub.6 alkyl, nitro, amino, a 5-6 membered organic heterocycle containing 1, 2 or 3 hetero atoms selected from nitrogen or sulfur, C.sub.1 -C.sub.6 alkoxy, or phenyl; or A and A' taken together form a group of the formulae ##STR2## wherein X is hydrogen, halo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkoxycarbonyl, amino, nitro, or carboxy; and Y is nitrogen or carbon; or a pharmaceutically acceptable salt thereof; pharmaceutical compositions and methods of treatment using the above compounds.

Abstract: 1-Carbapenam-2-one-3-carboxylic acid and 1-carba-3-hydroxy-3-cephem-4-carboxylic acid and esters thereof are provided by a process comprising a rhodium C.sub.2 -C.sub.10 carboxylate catalyzed cyclization of an ester of a 4-(1-alkoxy- or 1-substituted alkxoy)-2-oxo-4-azetidinyl)-.alpha.-diazo-.beta.-ketobutyric acid and an ester of a 5-(1-alkoxy- or 1-substituted alkoxy-2-oxo-4-azetidinyl)-.alpha.-diazo-.beta.-ketovaleric acid respectively. The process is carried out in an inert organic solvent at a temperature between about 15.degree. C. and about 85.degree.0 C. The 1-carba bicyclic .beta.-lactams are intermediates for preparing antibiotics.

Abstract: This invention relates to antibacterial compounds of the formula ##STR1## wherein A is hydrogen or an acyl group ##STR2## R.sub.a is a negative charge; R.sub.z is hydrogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, or a formamido group, --NHCHO; and --N.sup..sym. .tbd.Y is a quarternary ammonium group that may be acyclic, cyclic, or a combination of the two, and may contain on or more additional hetero atoms selected from nitrogen, sulfur and oxygen; and pharmaceutically acceptable non-toxic salts thereof.

Abstract: A method for preparing 2-amino-.beta.-lactams which are substituted by readily-removed protecting groups is provided. According to this invention, an acyl-2-amino-.beta.-lactam is further acylated with a different acyl group and is subsequently treated with base to provide a protected 2-amino .beta.-lactam with allyloxycarbonyl, t-butoxycarbonyl, naphthyloxycarbonyl, trichloroethyloxycarbonyl, p-nitrobenzyloxycarbonyl, benzhydryloxycarbonyl, p-methoxybenzyloxycarbonyl, or o-nitrobenzyloxycarbonyl.

Abstract: A heteroanellated phenylglycine-.beta.-lactam antibiotic of the formula ##STR1## in which R.sup.

Abstract: The crystalline bis(DMF), dihydrate mono(DMF) and mono(DMF) forms of 7.beta.-[2'-(R)-2'-phenyl-2'-aminoacetamido[-3-chloro-3-(1-carbadethiaceph em)-4-carboxylic acid (LY163892) are useful intermediates to the monohydrate form of LY163892.

Abstract: Novel antibiotics of the formula: ##STR1## and its salts, esters and amides wherein R is acyl;B is H, OMe, Me or SR wherein R is lower alkyl or aryl;A.sup.1 is hydrogen, hydroxy, or an organic group; and,X is a divalent radical selected from --O--, --CH.sub.2 --, or --NY-- where Y is hydrogen or lower alkyl of from 1 to 6 carbon atoms such as methyl, ethyl, i-propyl, n-butyl, n-pentyl, n-hexyl and the like, formyl or benzyl.This invention is directed to novel antibiotics, novel intermediates useful in their preparation, and processes for preparing the novel antibiotics. The novel antibiotics are effective against gram-negative bacteria including Proteus vulgaris, E. coli and Salmonella schottmulleri, and gram-positive bacteria including Staphylococcus aureas and Bacillus subtilis and are useful in combatting bacterial infections in animals or humans in addition to various industrial applications.

Abstract: There is described a 2-oxa-isocephem compound of the formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.4 are as defined, and R.sup.3 is a group of the formula: ##STR2## wherein n, m, R.sup.6, R.sup.7, B.sup.- and l are as defined, or pharmaceutically acceptable salt thereof. The compound has antimicrobial activity.

Abstract: The invention provides a free radical process for preparing 1-carba(1-dethia)cephalosporin antibiotics represented by the formula ##STR1## wherein R is amino or protected amino, R.sub.1 is H or alkoxy, R.sub.3 is H or alkyl, Z is ##STR2## where R.sub.2 is, e.g., H, halogen, or alkyl, or --CH.sub.2 R.sub.2 ' where R.sub.2 ' is, e.g., hydroxy, methoxy, or heterocyclicthio group, and A is a carboxy-protecting group which comprises heating a 2-substituted-methylcephalosporin 1,1-dioxide of the formula ##STR3## wherein R, R.sub.1, R.sub.3, and A are the same as in the formula above and Y is a free radical precursor group, e.g., C.sub.1 -C.sub.6 --Se--, C.sub.1 -C.sub.6 --S--, or phenyl--Se--; with a free radical initiator, e.g., a trialkyltin hydride, radiation, or a cobalt I salophen. Also provided are free radical compounds formed as intermediates in the process.

Abstract: 7.beta.-Acylamino-3-alkoxycarbonyl-(and 3-keto)-1-carba(1-dethia)-3-cephem-4-carboxylic acids and derivatives and related 3-substituted compounds are provided as antibiotics useful for treating infections in man and animals. Pharmaceutical formulations comprising the antibiotics and intermediates a process for their preparation are provided. Exemplary compounds provided are 7.beta.-[D-(2-phenyl-2-aminoacetyl)amino]-3-methoxycarbonyl-1-carba(1-deth ia)-3-cephem-carba(1-dethia)-3-cephem-4-carb oxylic acid and 7.beta.-[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetamido]-3-acetyl-1-carb a(1-dethia)-3-cephem-4-carboxylic acid.

Abstract: A process for photochemically converting 3-exomethylene cephams (or 1-carba(1-dethia)cephams or and 1-oxa(1-dethia)cephams) from the corresponding 3-alkyl-3-cephem (or 1-carba(1-dethia)cephem or 1-oxa(1-dethia)cephem) is provided. Further provided are 3-cephams useful as intermediates to 3-cephem compounds.

Abstract: 7.beta.-Acylamino-1-carba(dethia)-3-cephem-4-carboxylic acids represented by the formula ##STR1## wherein n is 1 or 2; R.sub.1 is C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.6 alkyl substituted by hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, trifluoromethyl, carboxy, carbamoyl, amino, C.sub.1 -C.sub.4 alkylamino, di-(C.sub.1 -C.sub.4 alkyl)amino, halogen, cyano, phenyl, substituted phenyl as defined above; C.sub.2 -C.sub.6 alkenyl; C.sub.3 -C.sub.7 cycloalkyl; phenyl or substituted phenyl as defined above; or a 5- or 6-membered heterocycle selected from thienyl, furyl, pyrryl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidyl, triazinyl, or pyrazinyl; the benzheterocycles, benzothienyl, benzofuryl, indolyl, benzimidazolyl, or benztriazolyl, and said 5- or 6-membered heterocycle and said benzheterocycle substituted by C.sub.1 -C.sub.4 alkyl, halogen, hydroxy, C.sub.1 -C.sub.

Abstract: Cephalosporin and 1-carba(1-dethia)cephalosporin antibiotics substituted in the 3-position with, inter alia, alkyl, alkenyl and alkynyl, are provided via process comprising conversion of a cephalosporin or 1-carba(1-dethia)-3-cephem substituted in the 3-position with halogen or a sulfonyloxy ester with Pd(O) mediated alkylation with organostannanes.

Abstract: 7.beta.-Acylamino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxyli c acid antibiotic compounds, esters and salts thereof, and the corresponding 7-amino and protected 7-amino 1-carbacephalosporins are provided. The 3-trifluoromethylsulfonyloxy-substituted 1-carbacephalosporins also are useful in a process for preparing 3-halo-1-carbacephalosporins which comprises reacting a 3-triflate ester with a lithium halide in an aprotic polar solvent.

Abstract: A process for preparing 7.beta.-acylamino (or 7.beta.-protected amino)-3-H-1-carba(1-dethia)-3-cephem-4-carboxylic acid esters and the corresponding cephalosporins is provided. 7.beta.-Acylamino (or 7.beta.-protected amino)-3-halo (or 3-sulfonyl ester)-1-carba(dethia)-3-cephem carboxylic acid esters and the corresponding cephalosporins are reduced with Pd(O) and a tetra-C.sub.2 -C.sub.6 alkyl stannane and, when a 3-sulfonyloxy ester is reduced, the process is carried out in the presence of an alkali metal halide. 3-Sulfonyloxy-3-cephem esters such as 3-mesylate, 3-tosylate and 3-triflate are employed.

Abstract: The invention provides azetidinones of the formula ##STR1## where R.sub.4 is hydrogen, amino or protected amino; R.sup.0 is H when R.sub.4 is amino or protected amino, or C.sub.1 -C.sub.4 alkyl when R.sub.4 is H; R.sub.1 is H, CH.sub.3, --CH.sub.2 --.sub.n Y where Y is OH, protected OH, --CH.sub.2 OH, protected --CH.sub.2 OH, halogen, COOH or protected COOH; n is 1 or 2; --CH.sub.2 --C(O)SR.sub.1 ' where R.sub.1 ' is e.g., C.sub.1 -C.sub.4 alkyl; R.sub.2 is H or protecting group and R.sub.3 is e.g., alkyl or phenyl. The azetidinones obtained are useful intermediates to carbapenems and carbacephems and monocyclic antibacterials, e.g., .alpha.-(dialkylphosphono)-[[3.beta.-[2-(2-aminothiazol-4-yl)-2-(syn)metho xyiminoacetylamino]azetidin-2-one-1-yl]]acetic acid and pharmaceutically acceptable salts thereof.