Abstract: Disclosed is a penicillin derivative of the formula: ##STR1## wherein n is an integer of 0, 1 or 2; Y is a cyano group, a lower acyl group, a mono- or di-lower alkylthiocarbamoyl group, ##STR2## wherein R.sub.1 is a hydrogen atom, a lower alkyl group, a phenyl group, a group --(CH.sub.2).sub.m --OR.sub.2 or --(CH.sub.2).sub.m COOR.sub.2 (m is an integer of 1 to 6 and R.sub.2 is a hydrogen atom or a penicillin carboxyl ester-forming group which is commonly used for penicillin derivatives) or a phenyl group substituted by at least one member selected from the class consisting of lower alkyl group, halogen atom and lower alkoxy group; and R is a hydrogen atom or a penicillin carboxyl ester-forming group, or a salt thereof. They are useful as .beta.-lactamase inhibitors.

Abstract: The present invention relates to a method for producing novel 4-[1-oxoalkyl]-2,5-oxazolidinediones, (4-1 OOD), and their use in a stereoselective method of producing beta-lactam-containing compounds which include several biologically active compounds such as the well-known families of penicillin and cephalosporin antibiotics. The method of the present invention involves generally the reaction of the above-described 4-[1-oxoalkyl]-2,5-oxazolidinediones so produced with a thiol amine having a geometry amenable to forming the precursor of the desired beta-lactam-containing compound or, in one scheme, forming the beta-lactam-containing compound itself directly. This is done either by direct reaction of the 4-1 OOD with a thiol amine (which by one pathway proceeds directly to the beta-lactam-containing compound) or by first converting the 4-1 OOD to its 2-[1-oxoalkyl]-2-amino acid form before its reaction with the thiol amine; and then forming the beta lactam by action of cyanogen).

Abstract: A compound of formula I ##STR1## with R.sup.1 being an alkyl group substituted by one or more substituents and esters thereof at the 2-carboxy group or at the 8-hydroxy group or both; and salts thereof. Compounds I have antibacterial effect. Various intermediates are described. This compound of the formula I, or an ester at the 2-carboxy group or at the 8-hydroxy group or both or a salt thereof is produced by reacting a compound of formula II or of formula IX ##STR2## in which R represents a hydrogen atom or a carboxy protecting group, R.sup.3 represents an activated carboxylic acid group, R.sup.4 represents an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may be unsubstituted or substituted, R.sup.15 represents a phenyl group or an alkyl group having from 1 to 4 carbon atoms, and X represents an oxygen or sulphur with an amine of the formula III R.sup.1 NH.sub.

Abstract: Compounds of the formula (V): ##STR1## wherein R.sup.1 is certain optionally substituted alkyl groups, R.sup.2 is hydrogen, alkyl or optionally substituted phenyl and R.sup.3 and R.sup.4 are independently alkyl or optionally substituted phenyl, or together form a C.sub.4-7 cycloalkyl ring; are described as useful intermediates in the preparation of carbapenem and penem antibiotics. Processes for their preparation are described as are certain oxadiazine intermediates.

Abstract: Derivatives of Penicillin, their sulfoxides and sulfones are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.

Abstract: Compounds of the following formula I ##STR1## wherein X represents a sulphur or an oxygen atom,R is hydrogen or a C.sub.1 -C.sub.4 alkyl group either unsubstituted or substituted by one or more substituents chosen from a free or protected hydroxy group and halogen atom;A is a Z, Z--O--CO-- or --Z--CO-- residue, whereinZ represents(a) an optionally substituted phenylene or naphthylene group,(b) an optionally substituted heterocyclediyl radical wherein the hetero ring is mono or bicyclic, saturated or unsaturated containing at least one heteroatom selected from the group of oxygen, sulphur and nitrogen;(c) an optionally substituted linear or branched C.sub.1 -C.sub.7 alkylene radical;(d) a C.sub.2 -C.sub.4 alkenylene or alkynylene group or a group of formula ##STR2## (e) an optionally substituted C.sub.3 -C.sub.8 cycloalkylene ring; (f) an aralkylene radical of the formula ##STR3## wherein n is 1, 2 or 3; andQ.sup.(+) represents a +NR.sub.1 R.sub.2 R.sub.3 group, wherein(i) R.sub.1, R.sub.2, R.sub.

Abstract: Beta-lactamase inhibiting compounds of the formula ##STR1## or a pharmaceutically acceptable acid addition or carboxylate salt thereof; where n is zero, 1 or 2; X.sub.3 is H or Br, R.sup.1 is H, the residue of certain carboxy-protecting groups or the residue of an ester group readily hydrolyzable in vivo; one of R.sup.12 and R.sup.13 is H and the other is vinyl, certain aryl, alkylthio, alkylsulfonyl or certain heterocyclyl, aminomethyl, thiocarboxamido or amidino groups; one or R.sup.2 and R.sup.3 is H and the other is as disclosed for the other of R.sup.12 and R.sup.13, or is Cl or CH.sub.2 OH, and R.sup.18 is H or certain acyl groups; intermediates useful in their production, methods for their preparation and use, and pharmaceutical compositions containing them.

Abstract: Compounds of the formula ##STR1## in which R.sub.1 represents lower alkyl substituted by hydroxy or by protected hydroxy, R.sub.2 represents carboxy or functionally modified carboxy, and R.sub.3 represents optionally substituted 3-pyridyl or optionally substituted 4-pyridyl, and pharmaceutically acceptable salts of such compounds, have antibacterial activity. The compounds of the formula I can be manufactured according to processes known per se.

Abstract: Disclosed is a process for preparing 3-substituted-thio-6-(1'-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene -2-carboxylic acids (I) ##STR1## wherein X is a leaving group such as chloro, bromo, tosyl, mesyl or the like; and R.sup.8 is, inter alia, selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl. The compounds I as well as their pharmaceutically acceptable O- and carboxyl derivatives are useful as antibiotics.

Abstract: A stereospecific process for preparing 3-trans-R-trisubstituted silyloxyethyl substituted azetidinones useful as intermediates for preparing penems and carbapenems is provided wherein a 3-unsubstituted azetidinone is treated with a strong base and a trisubstituted silylmethyl ketone to form 3-trans-S-[1-trisubstituted silyl-1-hydroxy]ethylazetidinone followed by rearrangement of this resulting carbinol by treatment with an alkali metal alkoxide and a proton source.

Abstract: The present invention relates to a new process for the debromination and/or deiodination of 6,6-dihalo- and 6-monohalopenicillanic acids or derivatives thereof by treatment with dialkyl, trialkyl or diaralkyl phosphite, the desired compounds being obtained in good to excellent yield and in a high state of purity.

Abstract: Processes for the production of 6-hydroxyethyl-2-substituted thio penem-3-carboxylates are disclosed as well as novel penems.

Abstract: There is disclosed antibacterial compounds represented by the formula ##STR1## and pharmaceutically acceptable salts or pharmaceutically acceptable esters thereof,wherein:X represents oxygen, sulfur, ##STR2## wherein R is hydrogen, loweralkyl, acetate or methoxycarbonyl; Y is cis, trans or mixtures thereof and is selected from hydroxy, lower alkoxy, aminocarbamoyloxy, methoxycarbonylamino, lower alkylcarbonyloxy, lower alkylcarbonylamino and loweralkylsulfonylamino; andthe wavy lines indicate cis, trans or mixtures thereof.

Abstract: Compounds of the general formula I: ##STR1## and their pharmaceutically acceptable salts and in vivo hydrolyzable esters, in whichone of R.sup.1 and R.sup.2 denotes hydrogen,the other of R.sup.1 and R.sup.2 denotes an unsubstituted or substituted five-membered hetero-aromatic ring bonded through a carbon atom thereof and having one hetero-atom selected from nitrogen, oxygen and sulphur and additionally having from one to three nitrogen atoms, andR.sup.3 denotes hydrogen or an organic group,are novel compounds with .beta.-lactamase inhibitory and antibacterial properties.

Abstract: .beta.-Lactam derivatives and analogs are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.

Abstract: 6-(1-Carbamoyl-1-hydroxymethyl)penicillanic acid derivatives are useful as antibacterials and/or beta-lactamase inhibitors.

Abstract: A compound of the formula I ##STR1## in which R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms, the --CONHR.sup.1 group being present at the 3- or 4-position on the phenyl ring, and esters thereof at the 2-carboxyl group and/or at the 8-hydroxy group, have antibacterial and/or .beta.-lactamase inhibiting activity.

Abstract: 2-Heterocyclyl-lower alkyl-6-hydroxy-lower alkyl-2-penem compounds of the formula ##STR1## in which R.sub.1 represents lower alkyl substituted by hydroxy or protected hydroxy, R.sub.2 represents carboxy or functionally modified carboxy, R.sub.3 represents an unsaturated monocyclic azaheterocyclyl radical bonded via a tertiary ring nitrogen atom to the radical -A- and A represents a lower alkylene radical, optical isomers of compounds of the formula (I), mixtures of these optical isomers and salts of such compounds of the formula (I) that contain a salt-forming group have antibiotic properties. The novel compounds can be used, for example, in the form of antibiotically active preparations for the treatment of infectious diseases. The novel compounds can be manufactured in a manner known per se.

Abstract: An efficient process for converting readily available 4-acetoxy-2-azetidinones to allyl 2-thioxopenam-3-carboxylates, intermediates useful for the synthesis of penem antibiotics.

Abstract: Antibacterial penicillins of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein R.sup.1 is a heterocyclic group and R is hydrogen, the residue of certian carboxy protecting groups or the residue of an ester group readily hydrolyzable in vivo having activity against resistant organisms.

Abstract: A process for the synthesis of penems from azetidinones via 1-aza-4,5-dithiabicyclo[4.2.0]oct-2-en-8-one-2-carboxylate esters.

Abstract: (5R) (Z)-6-(1-methyl,1,2,3-triazol-4-yl-methylene)-penem-3-carboxylic acid and its salts are provided in analytically pure crystalline form, and the salts in hydrated form, for example (5R) sodium (Z)-6-(1-methyl-1,2,3-triazol-4-yl-methylene)penem-3-carboxylate monohydrate.

Abstract: Certain 2-azacycloalkylthio-2-penem-3-carboxylic acid compounds are useful as antibacterials for treating mammals and have the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein: R is ##STR2## A is alkylene having 2-4 carbon atoms, alkylene having 2-4 carbon atoms wherein a carbon atom has an oxo substituent or alkylene having 2-4 carbon atoms wherein a methylene is replaced by oxygen, S(O).sub.m, or N--R.sub.3 ;B is carbonyl, thiocarbonyl, methylene or imine;R.sub.1 is hydrogen or forms an ester group which is hydroyzed in vivo;R.sub.2 is hydrogen, formyl, alkylcarbonyl, N-alkylaminocarbonyl, N-alkylaminosulfonyl, aminosulfonyl, aminocarbonyl, alkoxycarbonyl having 2-5 carbon atoms, alkylsulfonyl, alkyl, or alkyl substituted by aminocarbonyl, alkyl--S(O).sub.m --, hydroxyl, amino, alkylcarbonylamino, formamido or alkylsulfonylamino, wherein each alkyl has 1-4 carbon atoms;R.sub.

Abstract: 6-(1-Acyl-1-hydroxymethyl)penicillanic acid derivatives are useful as antibacterials and/or beta-lactamase inhibitors.

Abstract: There is disclosed the compound (5R,6S,8R)-6-(1-hydroxyethyl)-2-(3R-pyrrolidin-2-one-3-yl)thiopenem-3-carb oxylic acid, and pharmaceutically acceptable salts and esters as well as compositions containing them and methods for their use.

Abstract: A process for the preparation of penicillanic acid 1,1-dioxide and esters thereof readily hydrolyzable in vivo, which comprises oxidation of a 6,6-dihalopenicillanic acid, or an ester thereof readily hydrolyzable in vivo, to the corresponding 6,6-dihalopenicillanic acid 1,1-dioxide or ester thereof, followed by dehalogenation (e.g. by hydrogenolysis). The 6,6-dihalopenicillanic acid 1,1-dioxides and esters thereof readily hydrolyzable in vivo are novel intermediates. Penicillanic acid 1,1-dioxide, and esters thereof readily hydrolyzable in vivo, are known compounds which are useful as beta-lactamase inhibitors and for enhancing the effectiveness of certain beta-lactam antibiotics (e.g. the penicillins) in the treatement of bacterial infections in mammals, particularly humans.

Abstract: The invention relates to (5R,6S)-2-aminomethyl-6-[(1R)-1-hydroxyethyl]-2-penem-3-carboxylic acid in crystalline form and a process for the manufacture thereof. The substance is suitable for treating infectious diseases.

Abstract: Described is a novel process for the preparation of penams and penems useful as antibacterial agents, which comprises the reaction of an appropriate f-substituted-azetidin-2-one with a base, followed by reaction of the thereby formed penam compound with an oxidating agent and an organic or inorganic base.Also described are novel pemam compounds useful as antibacterials which are prepared by the described process.

Abstract: Disclosed are 6-substituted-2-carbamimidoyl-pen-2-em-3-carboxylic acids (I) having the representative structure: ##STR1## wherein R.sup.6, and R.sup.7 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkoxyl, halo, OH, COOH, alkenyl, aryl and aralkyl; A is a direct, single bond connecting the indicated S and C atoms, or A is a cyclic or acyclic connecting group selected, inter alia, from alkyl, cycloalkyl, aryl, heteroaryl, heteroalkyl; R.sup.1 and R.sup.2, which define the carbamimidoyl function, are, inter alia, independently selected from hydrogen, alkyl, aryl; additionally, said carbamimidoyl is characterized by cyclic structures achieved by the joinder of the two nitrogen atoms via their substituents and by their joinder to connecting group A; additionally, "carbamimidiums" are disclosed by quarternization of one of the nitrogen atoms of said carbamimidoyl.

Abstract: Disclosed is a process for preparing 3- and 6-substituted-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acids: ##STR1## wherein: X is a leaving group such as chloro, bromo, tosyl, mesyl or the like; and R.sup.6, R.sup.7 and R.sup.8 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl. Such compounds (I), as well as their pharmaceutically acceptable salt, ester and amide derivatives, are useful as antibiotics.

Abstract: Disclosed are 6-(1'hydroxyethyl)-2-(azacycloalkyl)penem-3-carboxylic acids and salts or metabolizable esters thereof having an absolute stereochemistry of 5R,6S,8R. The compounds are useful and potent antibacterial agents and can be formulated into a variety of forms suitable for oral, parenteral or topical use.

Abstract: Novel .beta.-lactam compounds classified into penem compounds, a process for preparing the same and use of such .beta.-lactam compounds are disclosed. These .beta.-lactam compounds exhibit excellent antimicrobial activities useful as pharmaceuticals or they are important intermediates for the synthesis of compounds having antimicrobial activities.

Abstract: The present invention relates to certain penem derivatives of the general formula I ##STR1## in which R represents a hydrogen atom or a carboxyl esterifying group, R.sup.1 represents certain unsubstituted and substituted aromatic and heterocyclic groups, and R.sup.2 represents a hydrogen atom, an unsubstituted or substituted alkyl or aryl group.The compound of formula I and salts thereof may be used in the treatment of bacterial infections in man and other animals.

Abstract: Process and intermediates for the conversion of 3R,4R-4-acetoxy-3-[1R-1-(silyloxy)ethyl]-2-azetidinones to antibacterial 5R,6S-6-(1R-1-hydroxyethyl)-2-(1-oxo-3-thiolanylthio)-2-penem-3-carboxylic acids, and the pharmaceutically-acceptable salts and pivaloyloxymethyl esters thereof.

Abstract: Disclosed is a process for the total synthesis of thienamycin from L-aspartic acid via intermediate III: ##STR1##

Abstract: Antibacterial compounds of formula (I) ##STR1## wherein, R.sub.1 ' is alkyl or hydroxyalkyl;R.sub.2 is hydrogen or a carboxy protecting group; andY' is a group-S-heterocyclic or pyridyl, which group may be substituted, and pharmaceutically or veterinarily acceptable salts thereof and pharmaceutical compositions containing the same.

Abstract: A process for the preparation of penicillanic acid 1,1-dioxide and esters thereof readily hydrolyzable in vivo, which comprises oxidation of a 6,6-dihalopenicillanic acid, or an ester thereof readily hydrolyzable in vivo, to the corresponding 6,6-dihalopenicillanic acid 1,1-dioxide or ester thereof, followed by dehalogenation (e.g. by hydrogenolysis). The 6,6-dihalopenicillanic acid 1,1-dioxides and esters thereof readily hydrolyzable in vivo are novel intermediates. Penicillanic acid 1,1-dioxide, and esters thereof readily hydrolyzable in vivo, are known compounds which are useful as beta-lactamase inhibitors and for enhancing the effectiveness of certain beta-lactam antibiotics (e.g. the penicillins) in the treatment of bacterial infections in mammals, particularly humans.

Abstract: A new process is described for the preparation of (5R)-penem derivatives of the general formula I: ##STR1## wherein R.sub.1 represents a hydrogen atom or an organic group; R.sub.2 represents a hydrogen atom or a carboxy protecting group and Y represents a hydrogen or halogen atom or an organic group. A 2-thiacephem derivative of the general formula II: ##STR2## wherein R.sub.1, R.sub.2 and Y have the meanings/given above is oxidized by means of organic peracids to the corresponding sulphone of the general formula III: ##STR3## which is subsequently submitted to a desulphurative ring contraction by extrusion of SO.sub.2 to give exclusively the desired (5R)-penem derivatives of the general formula I.

Abstract: Crystalline dimethyliminothienamycin having the formula ##STR1## and its preparation are disclosed.

Abstract: .beta.-Lactam derivatives and analogs are found to be potent elastase inhibitors and thereby useful anti-inflammatory/antidegenerative agents.

Abstract: Disclosed are 6- and 6,6-disubstituted-3-substituted amino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acids (I): ##STR1## wherein R.sup.1 and R.sup.2 are, inter alia, independently selected from the group consisting of hydrogen, substituted and unsubstituted: alkyl, aryl, and aralkyl; and R' and R" are independently selected from the group consisting of: H, substituted and unsubstituted alkyl and aralkyl, or together form a substituted or unsubstituted cyclic group.Such compounds and their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering compounds and compositions when an antibiotic effect is indicated.

Abstract: An improved process for the preparation of the chloromethyl ester of sulbactam (chloromethyl penicillanate 1,1-dioxide), an intermediate in the synthesis of sultamicillin (the mixed methanediol ester of sulbactam and ampicillin).

Abstract: A process for the preparation of 6-amino-pencillanic acid-1,1-dioxide without protecing either the amino group or the carboxy group during oxidation, by oxidation of 6-amino-penicillanic acid or 6-amino penicillanic acid sulfoxide with an alkali metal permanganate in an aqueous medium.

Abstract: 1-aza-4,5-dithiabicyclo [4.2.0] oct-2-en-8-one-2 carboxylate ester intermediates useful for the synthesis of penems.

Abstract: The invention relates to 2-penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.a represents an organic radical bonded by a carbon atom to the ring carbon atom, a free, etherified or esterified hydroxy or mercapto group or a halogen atom, R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom, or an etherified mercapto group, and R.sub.2 represents a hydroxy group or an R.sub.2.sup.A radical that together with the carbonyl grouping --C(.dbd.O)-- forms a protected carboxyl group, and to salts of such compounds with salt-forming groups, processes for the manufacture of such compounds, pharmaceutical preparations containing compounds of the formula I with pharmacological properties, and their use. The compounds have antibiotic activity.

Abstract: This invention relates to 2-(heterocycloalkylthio)penems wherein the nitrogen of the heterocyclic ring is connected to the alkyl group, and to their use as antibacterial agents.

Abstract: Penem-derivatives of the formula I ##STR1## in which R is hydrogen or a carboxyl esterifying groupR.sup.1 is phenyl, naphthyl, thienyl, pyridyl, quinolyl or isoquinolyl any of which is optionally substituted by one, two or three substituents of the group halogen, cycloalkyl, --NH.sub.2, --CONH.sub.2, --NO.sub.2, --CN, --R.sup.2, --OR.sup.2, --SR.sup.2, --SO--R.sup.2, --SO.sub.2 R.sup.2, --CO--R.sup.2, --CO--O--R.sup.2, --CH.sub.2 --CO--O--R.sup.2, --NHR.sup.2, --NR.sup.2 R.sup.2', --CO--NH--R.sup.2, --CO--NR.sup.2 R.sup.2', --NH--CO--R.sup.2, --NH--CO--NH--R.sub.2, --NH--CO--NH--R.sup.2, --NH--SO.sub.2 --R.sup.2, --CF.sub.3, --CO--OH, --CO.sub.2 --CO--OH wherein R.sup.2 and R.sup.2' are the same or different and each represents alkyl of 1 to 4 carbon atomsor a salts thereof, process for the manufacture thereof and antibacterial pharmaceutical preparations containing them.

Abstract: 6-substituted-hydrocarbon-2-(substituted-thio)penem-3-carboxylic acids and cogeners having useful antibacterial activity are disclosed. The compounds are prepared in a reaction sequence starting with a 4-acyloxy-2-azetidinone.

Abstract: Disclosed are novel carbapenem derivatives characterized by a 2-substituent of the formula ##STR1## wherein A represents C.sub.2 -C.sub.6 straight or branched chain alkylene group and R.sup.10 and R.sup.11 each independently represents optionally substituted aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, aryl, heterocyclyl, heterocyclyl-aliphatic, heteroaryl or heteroaraliphatic, or R.sup.10 and R.sup.11 taken together with the S.sup..sym. to which they are attached represent an optionally substituted sulfur-containing heterocyclic ring. Such derivatives are useful as potent antibacterial agents. Also disclosed are processes for the preparation of such derivatives.

Abstract: Carbapenems and 1-methylcarbapenems having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently H, CH.sub.3, CH.sub.3 CH.sub.2 --, (CH.sub.3).sub.2 CH--, HOCH.sub.2, CH.sub.3 CH(OH)--, (CH.sub.3).sub.2 C(OH)--, FCH.sub.2 --, F.sub.2 CH, F.sub.3 C--, CH.sub.3 CH(F)--, CH.sub.3 CF.sub.2 --, or (CH.sub.3).sub.2 C(F)--;R.sup.3 is H-- or CH.sub.3 ;L isa bridging group comprising substituted or unsubstituted C.sub.1 -C.sub.4 straight, C.sub.2 -C.sub.6 branched or C.sub.3 -C.sub.7 cycloalkyl groups wherein the substituents are selected from C.sub.1 -C.sub.6 alkyl, O--C.sub.1 -C.sub.6 alkyl, S--C.sub.1 -C.sub.6 alkyl, CF.sub.3, N(C.sub.1 -C.sub.6 alkyl).sub.2 ;N.sup.+ is a quaternary, monocyclic or bicyclic substituted or unsubstituted, heteroaryl group containing (a) when monocyclic, up to 3 heteroatoms and up to 6 total ring atoms, or (b) when bicyclic, up to 5 heteroatoms and 9-10 ring atoms, which is optionally substituted with one or more groups;their preparation and antibiotic use are disclosed.