Abstract: Disclosed are 6- and 6,6-disubstituted-2-substituted thio-pen-2-em-3-carboxylic acids of the following structure: ##STR1## wherein: R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently selected from: hydrogen; substituted and unsubstituted: alkyl, cycloalkyl, halo, alkoxyl, alkenyl, aralkyl, aryl, heterocyclyl, heteroaryl, and heterocyclylalkyl; W is an electron withdrawing group, and, for example, is selected from: --COR.sup.5, --CN, SO.sub.2 C.sub.6 H.sub.5 ; R.sup.5 is hydrogen; substituted and unsubstituted: alkyl, aryl, aralkyl, heteroaryl, heterocyclyl, or heterocyclylalkyl; or R.sup.5 may be --OR.sup.6, --NR.sup.7 R.sup.8, and --SR.sup.9 ; wherein R.sup.6 is H; substituted and unsubstituted: alkyl, alkenyl, or a group which defines --CO.sub.2 R.sup.6 as a pharmaceutically acceptable ester wherein R.sup.6 is, for example, phthalidyl, or 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl; R.sup.7 and R.sup.

Abstract: Compounds of the formula Ia and their tautomers Ib ##STR1## in which formulae R represents a carboxyl esterifying group are described, as well as processes for their manufacture. Ia and Ib are valuable starting materials for the preparation of various derivatives substituted at position 3 that possess antibacterial properties.

Abstract: This invention relates to penicillanic acid derivatives of the formula I ##STR1## in which X stands for chlorine, bromine or iodine, to pharmaceutically acceptable, non-toxic salts of the compounds of formula I, to pharmaceutically acceptable, easily hydrolyzable esters thereof, including salts of such esters, to pharmaceutical compositions containing the compounds of the invention and dosage units thereof, to methods for the preparation of the compounds of the invention, and to methods of using the said new compounds in the human and veterinary therapy.The 6.beta.-halopenicillanic acids of formula I are potent inhibitors of .beta.-lactamases from a variety of gram-positive and gram-negative bacteria, making the 6.beta.-halopenicillanic acids as well as their salts and easily hydrolyzable esters valuable in human and veterinary medicine.

Abstract: This invention provides a penicillin derivative of the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and represent hydrogen, C.sub.1-6 alkyl, C.sub.1-6 hydroxyalkyl, C.sub.3-9 acyloxyalkyl, C.sub.8-13 benzyloxyalkyl, C.sub.2-7 alkoxyalkyl, C.sub.2-7 alkoxycarbonyl, C.sub.3-8 alkenyloxycarbonyl, C.sub.3-8 alkynyloxycarbonyl, phenyl, amino, cyano, formyl, trifluoromethyl, C.sub.2-6 acyl, carbamoyl, C.sub.2-7 alkylcarbamoyl, benzyloxycarbonylamino, C.sub.2-7 alkoxycarbonylamino; and R.sub.3 is hydrogen, a group for forming a pharmaceutically acceptable salt, or a penicillin carboxyl protecting group, with the proviso that both of R.sub.1 and R.sub.2 are not hydrogen or C.sub.2-7 alkoxycarbonyl at the same time and that when one of R.sub.1 and R.sub.2 is hydrogen, the other is not C.sub.2-7 alkoxycarbonyl, or a pharmaceutically acceptable acid addition salt, process for preparing the derivative, and a pharmaceutical composition containing the derivative.

Abstract: Compounds of the formula ##STR1## in which R.sub.1 is lower alkyl substituted by hydroxy or by protected hydroxy,R.sub.2 represents carboxy or functionally modified carboxy, andR.sub.3 represents amino, lower alkyl-substituted amino, substituted methyleneamino or protected amino,optical isomers of compounds of the formula I, mixtures of these optical isomers, and salts of such compounds of the formula I that have a salt-forming group have antibiotic activity. The compounds of the formula I are manufactured according to processes that are known per se.

Abstract: 6-.beta.-Substituted penicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several .beta.-lactam antibiotics against many .beta.-lactamase producing bacteria, and 6-.beta.-substituted penicillanic acid derivatives wherein the carboxy group is protected by a conventional penicillin carboxy protecting group as useful intermediates leading to said synergistic agents. A process for converting 6,6-disubstituted penicillanic acid derivatives to the corresponding 6-.beta.-substituted penicillanic acid congeners.

Abstract: Disclosed are 6-(1-hydroxyethyl)-2-carbamimidoyl-pen-2-em-3-carboxylic acids (I) having the representative structure: ##STR1## wherein: 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, alkoxy, amino; 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 quaternization of one of the nitrogen atoms of said carbamimidoyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics.

Abstract: .beta.-lactams of the formula ##STR1## wherein R.sup.1 signifies hydrogen or a group readily cleavable by hydrolysis, A signifies the group R.sup.2 --N.dbd.C(CH.sub.3)--CH.dbd.C< or O.dbd.C(CH.sub.3)--CH.sub.2 --C(R.sup.3)<, R.sup.2 signifies hydroxy, lower alkoxy or arylamino and R.sup.3 signifies arylthio, lower alkanoylthio, lower alkoxycarbonylhydrazino or a N-containing saturated heterocycle attached via a N-atom, and pharmaceutically acceptable salts thereof, are disclosed. The compounds and their salts exhibit .beta.-lactamase inhibiting activities against .beta.-lactamases from bacteria.

Abstract: Compounds of formula (I): ##STR1## in which: R.sup.1 represents a hydrogen atom, an alkyl group, an alkoxy group or various substituted alkyl groups;R.sup.2 represents a hydrogen atom, a group of formula ##STR2## (in which R.sup.5 and R.sup.6 each represents an alkyl group, an aralkyl group or an aryl group, or R.sup.5 and R.sup.6 together represent a nitrogen-containing heterocyclic group) or a group of formula ##STR3## (in which R.sup.7 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a cyclic amino group, a hydroxy group, an alkoxy group, an aryloxy group, an aralkyloxy group, a substituted or unsubstituted hydrazino group or a guanidino group, and A' represents a bivalent saturated aliphatic hydrocarbon group); andR.sup.

Abstract: A novel, stable, crystalline sodium (5R,6S,8R)-6-(1-hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxyl ate (designated as Form II) is prepared by forming a homogenous solution of sodium (5R,6S,8R)-6-(1-hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxyl ate combined with stirring the homogenous solution for a time and at a temperature sufficient to produce Form II and recovering Form II. Form II may also be prepared by contacting a first solution obtained by dissolving (5R,6S,8R)-6-(1-hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxyl ic acid in dimethylacetamide with a second solution obtained by dissolving a sodium salt of an organic acid having a pKa of up to about 5, e.g., sodium 2-ethylhexanoate in acetone, in the presence of at least 5 volume percent water while stirring the reaction mixture so formed at a temperature and for a time sufficient to produce Form II followed by recovering Form II.

Abstract: A process for preparing 2-methyl substituted penems useful as antibiotics agent and/or as intermediates thereof, by reacting an appropriate 1-imido-3,4-disubstituted azetidinone derivative with a trivalent organophosphorus compound in an inert solvent at a temperature of from 110.degree. to 150.degree. C. for a period of from 2 hours to a few days.

Abstract: A 2-substituted or unsubstituted-6-(2-oxo-1, 3-dioxolan-4-yl)-2-penem-3-carboxylic acid derivative represented by the following formula (Ia) and: ##STR1## wherein R is hydrogen, a light metal or a carboxy-protecting group, R.sup.1 is an alkyl group, R.sup.2 is hydrogen, methyl or a substituted methyl group. The compounds have antibacterial activity.

Abstract: Penem derivatives are disclosed characterized by a substituted pyridiniomethyl group in the 2-position of the penem nucleus. The compounds of the present application exhibit better antibacterial activity than other known penem derivatives.

Abstract: Certain substituted-2-penem-3-carboxylic acid compounds, and pharmaceutically-acceptable salts thereof, can be prepared from the appropriate xanthate or trithiocarbonate by desulfurization, followed by halogenation and ring closure. The corresponding desulfurized and halogenated intermediates are disclosed.

Abstract: A process for the preparation of at least one compound of a formula selected from the group consisting of ##STR1## and their salts and esters wherein X is selected from the group consisting of hydrogen and a substituent such as halogen and acetoxy comprising diazotizing a compound of the formula ##STR2## and salts and esters thereof wherein X has the above definition and brominating the resulting diazotized compound with at least an equimolar amount of a nitrosating agent in the presence of 1 to 5 equivalents of a strong acid in solution or suspension in a mixture of water and an at least partially water-miscible organic solvent with the amount of water being 1 to 20% by volume containing at least equimolar amounts of hydrogen bromide and bromine which bromo compounds are useful intermediates for the preparation of penicillanic acid-1,1-dioxide and its derivatives and novel 6-diazo-intermediates.

Abstract: Certain 2-alkylthio-2-penem-3-carboxylic acid compounds are useful as antibacterials for treating mammals.

Abstract: There are disclosed 2(N-heterocyclyl) penems and their pharmaceutically acceptable salts and esters and their use as anti-bacterials.

Abstract: 2-heterocyclythio-lower alkyl-2-penem compounds of the formula ##STR1## in which R.sub.1 represents hydrogen or methyl, R.sub.2 represents an optionally protected hydroxy group, R.sub.3 represents carboxy or protected carboxy R.sub.3 ', R.sub.4 represents an unsaturated monocyclic heterocyclyl radical that is bonded via a ring carbon atom to the sulphur atom, and m is 2, 3 or 4, and salts of such compounds of the formula I that have a salt-forming group, optical isomers of compounds of the formula I and mixtures of these optical isomers, possess antibiotic properties. The compounds are manufactured according to processes known per se.

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

Abstract: Certain 2-dioxacycloalkylthio-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 carbonyl, methylene or thiocarbonyl; B is alkylene having 2-5 carbon atoms;alk is alkylene having 1-6 carbon atoms;R.sub.1 is hydrogen or a group which results in an ester which is hydrolyzable in vivo; andn is zero or one.

Abstract: A series of novel derivatives of penicillanic acid 1,1-dioxide, having a disubstituted methyl group of the formula X-CH-Y at the 6-position, and the pharmaceutically-acceptable salts thereof and the pharmaceutically-acceptable esters thereof readily hydrolyzable in vivo, wherein X is hydroxy, acylated hydroxy or amino and Y is carboxy or esterified carboxy. The compounds of the invention are inhibitors of bacterial beta-lactamases, and they will protect certain beta-lactamase-susceptible beta-lactam antibiotics, e.g. ampicillin, against inactivation by beta-lactamases. Co-administration of a compound of the invention with a beta-lactam antibiotic such as ampicillin to a mammalian subject increases the effectiveness of the beta-lactam antibiotic against infections caused by beta-lactamase-producing bacteria.

Abstract: Compounds of formula (I): ##STR1## (wherein R.sup.1 represents a C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.3 alpha-hydroxyalkyl group;R.sup.2 represents a hydrogen atom, a substituted or unsubstituted alkyl group or a cycloalkyl group;R.sup.3 represents a hydrogen atom or an alkyl group; and n is 1 or 2) and their salts and esters have valuable antibiotic activity and can be used for the treatment of diseases caused by a wide range of pathogenic microorganisms.