cas 61-33-6, Penicillin G | Articles data

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Light-triggered hydrophilic drug release from liposomes through removal of a photolabile protecting group
The antibiotic penicillin G cannot be completely incorporated into hydrophobic lipid-membranes owing to its hydrophilicity. Through modification with a hydrophobic and photolabile protecting group, penicillin G was effectively incorporated into liposomes and released by photoirradiation at 365?nm.
Goto, Yuya,Ueda, Masafumi,Sugikawa, Kouta,Yasuhara, Kazuma,Ikeda, Atsushi
p. 166 - 171
(2019)
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Synthesis of penicillin: 6-aminopenicillanic acid in penicillin fermentations.
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BATCHELOR,DOYLE,NAYLER,ROLINSON
p. 257 - 258
(1959)
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Sheehan,J.C.,Daves,G.D.
p. 2006 - 2008
(1964)
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Constantinides et al.
(1971)
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α-Carboxy-6-nitroveratryl: A photolabile protecting group for carboxylic acids
(Figure presented) The synthesis of a new photolabile protecting group for carboxylic acids, α-carboxy-6-nitroveratryl (αCNV), is described. Bromide 3, prepared in four steps from 3,4-dimethoxyphenylacetic acid, was used to alkylate carboxylic acids under mild conditions in good yield. Palladium-catalyzed deallylation afforded the acids 4a-h, which underwent rapid and quantitative photolysis at wavelengths longer than 300 nm to liberate the carboxylic acid in good to quantitative yield. The rate of photolysis and quantum yield were determined to be 325 s-1 and 0.17.
Russell, Alexander G.,Ragoussi, Maria-Eleni,Ramalho, Rui,Wharton, Christopher W.,Carteau, David,Bassani, Dario M.,Snaith, John S.
supporting information; scheme or table
p. 4648 - 4651
(2010/09/14)

Acyloxymethyl as a drug protecting group. Part 3. Tertiary O-amidomethyl esters of penicillin G: Chemical hydrolysis and anti-bacterial activity
Purpose. O-(N-alkylamido)methyl esters of penicillin G were studied as a new class of prodrugs. Methods. Their hydrolysis in aqueous buffers containing 20% (v/v) of acetonitrile was investigated by HPLC. Results. A U-shaped pH-rate profile was seen with a pH-independent process extending from pH ca. 2 to pH ca. 10. This pathway is characterised by kinetic data that are consistent with a unimolecular mechanism involving rate-limiting iminium ion formation and penicillinoate expulsion. Penicillin G and the corresponding amide are the ultimate products detected and isolated, indicating that p-lactam ring opening is much slower than ester hydrolysis. The O-(N-alkylamido)methyl esters of penicillin G displayed similar in vitro antibacterial activity to penicillin G itself. Conclusions. Compared to the penicillin G derivatives, the much higher stability of the O-(N-methylbenzamido)methyl benzoate, acetate and valproate esters (which gave rise to a Bronsted β(1g) value of ca. -1) suggests that tertiary N-acyloxymethylamides may be useful prodrugs for carboxylic acid drugs with pK(a) > 4.
Moreira, Rui,Calheiros, Teresa,Cabrita, Jose,Mendes, Eduarda,Pimentel, Madalena,Iley, Jim
p. 70 - 75
(2007/10/03)

Prop-2-ynyl as a protective group for carboxylic acids: A mild method for the highly selective deprotection of prop-2-ynyl esters using tetrathiomolybdate
It is shown that prop-2-ynyl esters are useful protecting groups for carboxylic acids and that they are selectively deprotected in the presence of other esters on treatment with tetrathiomolybdate under mild conditions.
Ilankumaran, Palanichamy,Manoj,Chandrasekaran, Srinivasan
p. 1957 - 1958
(2007/10/03)

A New Direct Synthesis of Tertiary N-Acyloxymethylamide Prodrugs of Carboxylic Acid Drugs
N-Alkyl-N-chloromethylamides 2, prepared from secondary amides, paraformaldehyde and chlorotrimethylsilane, react readily with carboxylate anions to generate the corresponding tertiary N-acyloxymethylamides 3 in good yield; the latter give rise to the parent carboxylic acids in aqueous media at pH 7.4 and 37 deg C with half-lives between ca. 1 min and 42 h.
Moreira, Rui,Mendes, Eduarda,Calheiros, Teresa,Bacelo, Maria J.,Iley, Jim
p. 7107 - 7110
(2007/10/02)

Bioreaction engineering for improved 6-APA production
Bioreaction engineering gives tools to improve the production of 6-aminopenicillanic acid by enzyme-catalyzed hydrolysis of penicillin G, using penicillin G amidase (E.C. 3.5.1.11) immobilized on polyacrylamide.The influence of buffer concentration on preventing development of a lower pH at the immobilized enzyme, and application of lower substrate concentrations for reduction of product inhibition are examined.A mathematical model for simulation of the process is also developed.
Danzig, Joachim,Tischer, Wilhelm,Wandrey, Christian
p. 40 - 43
(2007/10/02)

Thiazolidine Ring Opening in Penicillin Derivatives. Part 2. Enamine Formation
The alkaline hydrolysis of (3S,5R,6R)-methyl benzylpenicilloate, and the corresponding carboxamide and N-ethylamide, is accompanied by an absorbance increase at 285 nm.This is attributed to a competing elimination reaction across C6-C5 to open the thiazolidine ring and reversibly generate an enamine intermediate.Kinetic analysis and hydrolysis in D2O do not indicate a significant buildup of this intermediate during hydrolysis of the methyl ester.However, over the pH range 4-11 the rate of thiazolidine ring opening is competitive with hydrolysis of the ester function.The deuterium solvent kinetic isotope effect on the ring closure reaction is 7.5.
Davis, Andrew M.,Layland, Nicola J.,Page, Michael I.,Martin, Frances,O'Ferrall, Rory More
p. 1225 - 1229
(2007/10/02)

Substituted acrylamido-penicillanic acid derivatives
Compounds of formula (I) and their derivatives: wherein X is hydrogen or a group NHR1, wherein R1 is hydrogen or an amino protecting group, and R is an optionally substituted spiro, fused or bridged bicyclic group optionally containing one or more heteroatoms selected from oxygen, nitrogen and sulphur, are new and useful in the treatment of bacterial infections in humans and animals.
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(2008/06/13)

Penicillins having a substituted acrylamido side chain
Compounds of formula (I) and their salts and esters: STR1 wherein X is hydrogen or a group NHR1, wherein R1 is hydrogen or an amino protecting group, and R is optionally substituted C5-8 cycloalkyl or cycloalkenyl, are useful in the treatment of bacterial infections.
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(2008/06/13)

Aminothiazole substituted penicillins and antibacterial compositions thereof
The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt or in-vivo hydrolysable ester thereof: STR1 wherein R1 is hydrogen or an amino protecting group and R is substituted methyl; optionally substituted C2-12 alkyl, alkenyl or alkynyl; carbocyclyl; aryl or heterocyclyl. These compounds have antibacterial properties, and therefore are of use in the treatment of bacterial infections in humans and animals caused by a wide range of organisms.
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(2008/06/13)

MILD PALLADIUM(0)-CATALYZED DEPROTECTION OF ALLYL ESTERS. A USEFUL APPLICATION IN THE SYNTHESIS OF CARBAPENEMS AND OTHER β-LACTAM DERIVATIVES.
Carbapenem and other β-lactam allyl ester derivatives are efficiently deprotected with pyrrolidine in the presence of catalytic amount of Pd(0).
Deziel, Robert
p. 4371 - 4372
(2007/10/02)

Penicillin Biosynthesis: Direct Biosynthetic Formation of Penicillin V and Penicillin G
The enzyme isopenicillin N synthetase is able to convert directly the dipeptides, phenoxyacetylcysteinylvaline and phenylacetylcysteinylvaline into penicillin V and G respectively; these are however very slow compared with substrates of the α-aminoadipoyl or adipoylcysteinylvaline type.
Baldwin, Jack E.,Abraham, Edward P.,Burge, Geoffrey L.,Ting, Hong-Hoi
p. 1808 - 1809
(2007/10/02)

β-Lactam antibacterial agents
β-Lactam antibiotics having an α-formamido substituent on the carbon atom adjacent to the carbonyl group of the β-lactam ring and in particular bicyclic compounds having the partial structure: STR1 Intermediates and processes for the preparation of the compounds are further disclosed.
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(2008/06/13)

6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors
6-beta-Halopenicillanic acid 1,1-dioxides, physiologically acceptable salts thereof and esters thereof readily hydrolyzable; pharmaceutical compositions containing a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable; and a method for enhancing the effectiveness of a beta-lactam antibiotic, using a 6-beta-halopenicillanic acid 1,1-dioxide, a physiologically acceptable salt thereof or an ester thereof readily hydrolyzable.
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(2008/06/13)

Cephalosporin derivatives
Penicillins and cephalosporins of the formula STR1 wherein A is phenyl, 4-hydroxyphenyl, cyclohexyl, cyclohene-1-yl, cyclohexa-1,4-diene-1-yl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl or 3,4-disubstituted phenyl, where the substituents, which may be identical to or different from each other, are each chlorine, hydroxyl or methoxy; R1 is an unsubstituted or substituted 5- or 6-membered heterocycle comprising carbon atoms and 1 to 4, preferably 1 to 2, identical or different heteroatoms such as oxygen, sulfur or nitrogen; n is 0 or 1; X is STR2 D is hydrogen, hydroxyl, acetoxy, aminocarbonyloxy, pyridinium, aminocarbonyl-pyridinium or S-Het, where Het is 1-methyl-tetrazol-5-yl, tetrazol-5-yl, 3-methyl-1,2,4-thiadiazol-5-yl, 1,2,4-triadiazol-5-yl, 1,3,4-thiadiazol-5-yl, 2-methyl-1,3,4-thiadiazol-5-yl, 2-methylamino-1,3,4-thiadiazol-5-yl, 2-dimethylamino-1,3,4-thiadiazol-5-yl, 2-formylamino-1,2,4-thiadiazol-5-yl, 2-acetylamino-1,3,4-thiadiazol-5-yl, 2-methyl-1,3,4-oxadiazol-5-yl, 1,2,3-triazol-4-yl or 1,2,4-triazol-3-yl; and E is hydrogen or a protective group which is easily removable in nitro or in vivo, especially an ester-forming group which can be removed under mild conditions by hydrogenation or hydrolysis or other treatments, or an ester-forming group which can easily be split off in the living organism; and, when E is hydrogen, their non-toxic, pharmacologically acceptable salts thereof, such as their alkali metal or alkaline earth metal salts, especially the sodium, potassium, magnesium or calcium salts; their ammonium salts; or their organic amine salts, especially the triethylamine or dicyclohexylamine salts. The compounds are useful as antibiotics.
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(2008/06/13)

Pyrimidinyl ureido penicillins
Compounds of the formula STR1 wherein A is phenyl, 4-hydroxy-phenyl, 2-thienyl or 3,4-dihydroxy-phenyl; and R is STR2 where R1 and R2, which may be identical to or different from each other, are each methylmercapto or amino; Z' is oxygen, sulfur or =NR3 ; R3 is hydrogen, alkyl of 1 to 3 carbon atoms or hydroxy-(alkyl of 1 to 3 carbon atoms); R4 is hydrogen, hydroxyl, hydroxymethyl or methyl; n is 2, 3 or 4; Y is --SO2 NH--, --SO-- or --SO2 --; Z is straight or branched alkylene of 1 to 3 carbon atoms; X is hydroxyl, aminocarbonyl, aminosulfonyl, formylamino, acetylamino, amino, methylsulfinyl, methylsulfonyl or STR3 or --Y--Z--X is STR4 and non-toxic, pharmacologically acceptable salts thereof formed with inorganic or organic bases. The compounds as well as the salts are useful as antibiotics.
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(2008/06/13)

Penicillins
Compounds of the formula STR1 wherein A is phenyl, p-hydroxy-phenyl, 2-thienyl, 3-thienyl or 3,4-disubstituted phenyl, where the substituents, which may be identical to or different from each other, are each chlorine, hydroxyl or methoxy; R is --NH--Z--X; Z is straight or branched alkylene of 1 to 6 carbon atoms or cycloalkylene of 3 to 6 carbon atoms; X is cyano, hydroxyl, mercapto, aminocarbonyl, aminosulfonyl, STR2 R1 is straight or branched alkyl of 1 to 4 carbon atoms or phenyl; R2 is hydrogen or alkyl of 1 to 4 carbon atoms; and R1 and R2, together with an adjacent nitrogen atom to which they are attached, form a 3- to 6-membered heterocyclic ring; and non-toxic, pharmacologically acceptable salts thereof formed with inorganic or organic bases.
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(2008/06/13)

ENZYMATIC SYNTHESIS OF ANTIBIOTIC (BENZYLPENICILLIN) IN BIPHASIC AQUEOUS-ORGANIC SYSTEM
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Semenov, A. N.,Martinek, K.,Shvyadas, V. Yu.-K.,Margolin, A. L.,Berezin, I. V.
p. 271 - 273
(2007/10/02)

ACETOXYMETHYL PENAM COMPOUNDS AS BETA-LACTAMASE INHIBITORS
2-beta-Acetoxymethyl-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide, pharmaceutically-acceptable salts thereof and esters thereof readily hydrolyzable in vivo; pharmaceutical compositions containing 2-beta-acetoxymethyl-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide or salt or ester thereof; and method of enhancing the effectiveness of a beta-lactam antibiotic using 2-beta-acetoxymethyl-2-alpha-methyl-(5R)penam-3-alpha-carboxylic acid 1,1-dioxide or salt or ester thereof
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(2008/06/13)

Method for increasing antibacterial effectiveness of a β-lactam antibiotic
6-Aminopenicillanic acid 1,1-dioxide, esters thereof readily hydrolyzable in vivo, and the pharmaceutically-acceptable salts of these compounds, are useful for enhancing the effectiveness of certain β-lactam antibiotics against certain β-lactamase producing bacteria. Derivatives of 6-aminopenicillanic acid 1,1-dioxide protected by a conventional carboxy protecting group are useful intermediates to 6-aminopenicillanic acid 1,1-dioxide and esters thereof readily hydrolyzable in vivo.
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(2008/06/13)

DERIVATIVES OF 6BETA-HYDROXYALKYLPENICILLANIC ACIDS AS BETA-LACTAMASE INHIBITORS
6beta-Hydroxyalkylpenicillanic acids and derivatives thereof as useful enhancers of the effectiveness of several beta-lactam antibiotics against many beta-lactamase producing bacteria, and 6beta-substituted penicillanic acid benzyl ester derivatives as useful intermediates leading to said agents which enhance the effectiveness of beta-lactam antibiotics
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(2008/06/13)

Beta-lactam antibiotics
Antibacterially active and animal feedstuff supplement β-lactam antibiotics of the formula STR1 in which R is H or --UR', U is O or S, R' is optionally substituted alkyl, alkenyl, alkinyl, aralkyl, aryl or cycloalkyl, Z is STR2 R1 and R2 individually are hydrogen or, individually or together with the carbon atom to which they are bonded, are any of various radicals, A is --CH2 --CH2 --, --CH2 --CH2 --CH2 -- or STR3 B is optionally substituted phenyl or is cyclohexenyl or cyclohexadienyl; X is S, O, SO, SO2 or --CH2 --; and Y is a group of the formula STR4 T is hydrogen, alkyl--CO--O--, pyridinium, aminopyridinium, carbamoyloxy, azido, cyano, hydroxyl or optionally substituted --S--phenyl, or is --S--Het, in which Het is an optionally substituted heterocyclic 5-membered or 6-membered ring; and wherein E is hydrogen, a radical forming, with the carboxyl group to which it is attached, a carboxy ester group, a cation of a salt, or a protective group, or a hydrate thereof. A process is also given for converting R directly from H to UR' employing a base, a halogenating agent and R'UH .
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(2008/06/13)

Penicillins and salts thereof
Compounds of the formula STR1 wherein A is phenyl; 4-hydroxy-phenyl; 2- or 3-thienyl; cyclohexyl; cyclohexen-1-yl; cyclohexa-1, 4-dien-1-yl; or 3,4-disubstituted phenyl, where the substituents may be identical to or different from each other and are selected from the group consisting of chlorine, hydroxyl or methoxy; and R is an aliphatic, cycloaliphatic; aromatic or heterocyclic group of diverse types; and non-toxic, pharmacologically acceptable salts thereof formed with inorganic or organic bases. The compounds as well as their salts are useful as antibiotics.
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(2008/06/13)

Penam 1,1-dioxides as beta-lactamase inhibitors
(3S, 5R)-Penam-3-carboxylic acid 1,1-dioxide, optionally having a methyl group at the 2-position, and esters thereof readily hydrolyzable in vivo, are useful for enhancing the effectiveness of several beta-lactam antibiotics against many beta-lactamase producing bacteria.
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(2008/06/13)

βLactam antibiotics and process for their use
6-[α-(Imidazolidin-2-on-1-ylcarbonylamino)-substutited acetamido]penicillanic acids, and the correspondingly 7-substituted ceph-3-em-4-carboxylic acids, characterized by the presence of a methyleneamino or substituted methyleneamino group on the 3-nitrogen atom of the imidazolidine ring are antibacterial agents. The compounds, of which 6-[α-(3-benzaliminoimidazolidin-2-on-1-ylcarbonylamino)cyclohexa-1,4-dien-1-ylacetamido]penicillanic acid and 7-[α-(3-furylideneaminoimidazolidin-2-on-1-ylcarbonylamino)phenylacetamido]-3-(3-methylthiadiazol-5-ylthiomethyl)ceph-3-em-4-carboxylic acid are typical examples, are prepared through acylation of an 6-[α-(amino)substituted acetamido]penicillanic acid or the corresponding 7-[α-(amino)substituted acetamido]ceph-3-em-4-carboxylic acid with a reactive nucleofugic derivative of a 3-methyleneaminoimidazolidin-2-on-1-carboxylic acid.
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(2008/06/13)

Thienopyridine substituted cephalosporins
Thienopyridine derivatives of the formula: STR1 wherein R1 and R2 are the same or different and each is hydrogen, an alkyl, an aryl, an aralkyl or a halogen; R1 and R2 may, taken together, represent an alkylene group; X is hydrogen or an alkyl; Y is oxygen or sulfur; Z is phenyl which may optionally be substituted; R3 is hydrogen or an alkoxy; and R is a group of the formula: STR2 or of the formula: STR3 (wherein R4 is hydrogen, an acyloxy or a nucleophilic compound residue) or a pharmaceutically acceptable salt thereof are found to have activity against a broad spectrum of gram-positive and gram-negative bacteria, particularly against bacteria of the genus Pseudomonas .
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(2008/06/13)

β-Aminopenicillins, salts and esters
β-Aminopenicillins, Salts and Esters are described having a wide spectrum of activity against Gram-positive and Gram-negative organisms. The β-aminopenicillins are derivatives of 6-amino-penicillanic acid and the procedure for preparing the β-aminopenicillins is set forth. β-aminopenicillins are characterized by having in the 6-position side chain a cycloalkyl ring of 5 - 7 carbon atoms particularly cyclopentyl, cyclohexyl or cycloheptyl.
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(2008/06/13)

Method for the preparation of 6-aminopenicillinic acid derivatives
6-AMINOPENICILLANIC ACID DERIVATIVES CHARACTERIZED BY THE GENERAL FORMULA STR1 wherein R = H, alkoxy group of normal and iso-structure having 1 to 4 carbon atoms, STR2 wherein n = 4, 3, 2, R1 is lower alkyl, aryl, halogen, NH2, NO2, OH, are prepared by acylating 6-aminopenicillanic acid with an acylating agent of the formula STR3 wherein R and X have the above-mentioned significance.
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(2008/06/13)

Penicillins
A class of α-(heterocyclic carbonylamino) penicillins in which the heterocyclic group of the acyl moiety is a fused bicyclic ring having a nitrogen atom at the bridge position, shows good antibacterial activity.
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(2008/06/13)

Penicillins and processes for their preparation and use
6-[α-(Imidazolidin-2-on-1-carbonylamido)acetamido]-penicillanic acids substituted in the 3-position of the imidazolidinone ring with phenyl or a substituted phenyl group and on the α-carbon atom of the acetamido bridge with a phenyl, thienyl, cyclohexenyl or cyclohexadienyl group, and their salts, are antibacterial agents. The compounds, of which α-(3-phenylimidazolidin-2-on-1-ylcarbonylamino)benzylpenicillin is a representative example, are prepared by acylation of the corresponding 6-(α-aminoacetamido)penicillanic acid or a derivative thereof.
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(2008/06/13)

Penicillins
A penicillin of the formula: STR1 wherein STR2 is a six-membered heteroaromatic ring containing 1 or 2 nitrogen atoms as the hetero atom, Y is hydrogen, lower alkanoyl or lower alkoxycarbonyl, R1 and R2 are each hydrogen, lower alkyl, lower alkanoyl, benzoyl, lower alkylmercapto, hydroxyl, mercapto, hydroxy(lower)alkyl, halogen or cyano or R1 and R2 may link together to form a lower alkylene chain which may be substituted with an oxo group, and Z is phenyl, hydroxyphenyl, lower alkyl, cyclohexadienyl, thienyl or isothiazolyl, which is prepared by reacting a compound of the formula: STR3 wherein Z is as defined above or its derivative with a carboxylic acid of the formula: STR4 wherein STR5 and R2 are each as defined above or its reactive derivative, if necessary, followed by hydrolysis or acylation of the resulting product and/or elimination of any protective group and which is useful as an antimicrobial agent against various gram-positive and gram-negative bacteria including Pseudomonas.
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(2008/06/13)

Acylaminopenicillanic acids and process for preparing them
Acylaminopenicillanic acids of the general formula STR1 in which R1, R2 and R3 represent hydrogen or lower alkyl which may be substituted, and in which the radicals R1 and R2 or R2 and R3 may form together an alkylene radical which may be substituted, R4 and R5 represent hydrogen or lower alkyl, R6 represents phenyl which may be substituted, a monocyclic aromatic heterocycle which may be substituted, or dihydrophenyl, A represents a benzene or thiophene ring which may be substituted, and X represents oxygen or a single bond, a process for preparing them and pharmaceutical compositions active against bacterial infections containing these compounds.
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(2008/06/13)

Process for the preparation of heterocyclic compounds
A process for the preparation of acylamido derivatives by reaction of a compound of the formula Z - N = C = O, wherein Z is an optionally substituted alkyl-, aryl- (preferably phenyl or naphthyl) or cycloalkyl or optionally substituted heterocyclic, preferably a penicillanic acid or a cephalosporanic acid nucleus, having carboxyl groups and an optionally present hydroxy group protected, with a carboxylic acid of the formula STR1 wherein Z1 is an optionally substituted hydrocarbon group, in the presence of a catalyst selected from the group consisting of substituted pyridines and their N-oxides, optionally substituted imidazoles or their N-oxides, optionally substituted benzimidazoles or their N-oxides, and optionally substituted imidazo [1,2-α] pyridines or their N-oxides.
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(2008/06/13)

Penicillins
Penicillins of the formula EQU1 or pharmaceutically acceptable non-toxic salts thereof, wherein C is a carbon atom constituting a center of chirality; A is a moiety of the formula EQU2 or EQU3 wherein X is EQU4 Y is EQU5 or wherein Aryl is an aryl moiety; Z is EQU6 Q1 is EQU7 or SPC1 Q2 is EQU8 SPC2 or SPC3 R is straight-chain or branched alkyl of 1 to 5 carbon atoms; R1 is alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkenyl of 3 to 10 carbon atoms, vinyl, arylvinyl, mono-, di-, or tri-halo-lower alkyl, H2 N--, R--NH--, (R)2 N--, aryl--NH--, aryl-lower alkylamino, alkoxy of 1 to 8 carbon atoms, aralkoxy of 1 to 8 carbon atoms in the alkoxy portion, cycloalkoxy of 3 to 7 carbon atoms, aryloxy, R--O--V--, R--S-- V--, N=C--V--, R--O--CO--V--, H2 N--CO--V--, R--NH--CO--V--, R--O--CO--NH--, R--SO2 --NH--, (R)2 N--CO--V--, wherein R is as above defined, SPC4 SPC5 provided that when X is --SO2 --, R1 is not alkoxy, aralkoxy, cycloalkoxy or aryloxy, and further provided that R1 can also be hydrogen when X is --CO--; V is a divalent organic radical of 1 to 3 carbon atoms; n is 0, 1 or 2; R2 and R3 are the same or different and are each hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, vinyl, allyl, propenyl, cycloalkyl of 3 to 6 carbon atoms, cycloalkenyl of 3 to 6 carbon atoms, mono-, di- or tri-halo lower alkyl or aryl; R4, r5 and R6 are the same or different and are each hydrogen, nitro, cyano, (R)2 N--, (R)2 N--CO--, R--CO--NH--, R--O--CO--, R--CO--O--, R--, R--O--, wherein R is as above defined, H2 N--SO2 --, chlorine, bromine, iodine, fluorine or trifluoromethyl; G is hydrogen or straight or branched chain alkyl of 1 to 5 carbon atoms; and B is a moiety of the formula SPC6 wherein R7, r8 ad R9 are the same or different and are each hydrogen, halogen, nitro, hydroxy, R--, R--0--, R--S--, R--SO--, R--SO2 --, (R)2 N--, R--CO--NH--, or R--CO--O--, wherein R is as above defined; the arrow in the divalent linking group → means that the linkage of two atoms by the free valencies of his group must take place as indicated by the arrow; exhibit activity against both Gram-positive and Gram-negative bacteria.
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(2008/06/13)

Penicillins
Arylmethyl- and cyclohexenylmethyl- penicillins, substituted on the α-carbon atom of the side chain by a 2,3-disubstituted imidazolidinylcarbamido or a 2,3-disubstituted imidazolidinylthiocarbamido group, or by the corresponding 2,3-disubstituted 1,3-diazacyclohexylcarbamido or thiocarbamido groups are anti-bacterial agents.
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(2008/06/13)

Penicillins
Arylmethyl- and cyclohexenylmethyl- penicillins, substituted on the αcarbon atom of the side chain by a 2,3-disubstituted imidazolidinylcarbamido or a 2,3-disubstituted imidazolidinylthiocarbamido group, or by the corresponding 2,3-disubstituted 1,3-diazacyclohexylcarbamido or thiocarbamido groups are anti-bacterial agents.
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(2008/06/13)

Penicillins
Arylmethyl- and cyclohexenylmethyl- penicillins, substituted on the αcarbon atom of the side chain by a 2,3-disubstituted imidazolidinylcarbamido or a 2,3-disubstituted imidazolidinylthiocarbamido group, or by the corresponding 2,3-disubstituted 1,3-diazacyclohexylcarbamido or thiocarbamido groups are anti-bacterial agents.
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(2008/06/13)

Penicillins
Penicillins of the formula EQU1 or pharmaceutically acceptable non-toxic salts thereof, wherein C* is a carbon atom constituting a center of chirality; A is a moiety of the formula EQU2 or EQU3 wherein X is EQU4 Y is EQU5 or wherein Aryl is an aryl moiety; Z is EQU6 Q1 is EQU7 or SPC1 Q2 is EQU8 SPC2 or SPC3 R is straight- chain or branched alkyl of 1 to 5 carbon atoms; R1 is alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, alkenyl of 2 to 10 carbon atoms, cycloalkenyl of 3 to 10 carbon atoms. vinyl, arylvinyl, mono-, di-, or tri-halo-lower alkyl, H2 N--, R--NH--, (R)2 N--, aryl--NH--, aryl-lower alkylamino, alkoxy of 1 to 8 carbon atoms, aralkoxy of 1 to 8 carbon atoms in the alkoxy portion, cycloalkoxy of 3 to 7 carbon atoms, aryloxy, R--O--V--, R--S--V--, N=C--V--, R--O--CO--V--, H2 N--CO--V--, R--NH--CO--V--, R--O--CO--NH--, R--SO2 --NH--, (R)2 N--CO--V--, wherein R is as above defined, SPC4 SPC5 provided that when X is --SO2 --, R1 is not alkoxy, aralkoxy, cycloalkoxy or aryloxy, and further provided that R1 can also be hydrogen when X is --CO--; V is a divalent organic radical of 1 to 3 carbon atoms; n is 0, 1 or 2; R2 and R3 are the same or different and are each hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, vinyl, allyl, propenyl, cycloalkyl of 3 to 6 carbon atoms, cycloalkenyl of 3 to 6 carbon atoms, mono-, di- or tri-halo lower alkyl or aryl; R4, r5 and R6 are the same or different and are each hydrogen, nitro, cyano, (R)2 N--, (R)2 N--CO--, R--CO--NH--, R--O--CO--, R--CO--O--, R--, R--O--, wherein R is as above defined, H2 N--SO2 --, chlorine, bromine, iodine, fluorine or trifluoromethyl; G is hydrogen or straight or branched chain alkyl of 1 to 5 carbon atoms; and B is a moiety of the formula SPC6 wherein R7, r8 and R9 are the same or different and are each hydrogen, halogen, nitro, hydroxy, R--, R--O--, R--S--, R--SO-- , R--SO2 --, (R)2 N--, R--CO--NH--, or R--CO--O-- , wherein R is as above defined; the arrow in the divalent linking group ←Q2 → means that the linkage of two atoms by the free valencies of this group must take place as indicated by the arrow; exhibit activity against both Gram-positive and Gram-negative bacteria.
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(2008/06/13)

Penicillins
Arylmethyl- and cyclohexenylmethyl- penicillins, substituted on the α-carbon atom of the side chain by a 2,3-disubstituted imidazolidinylcarbamide or a 2,3-disubstituted imidazolidinylthiocarbamido group, or by the corresponding 2,3-disubstituted 1,3-diazacyclohexylcarbamido or thiocarbamido groups are anti-bacterial agents.
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(2008/06/13)

Penicillins
Penicillins of the formula: SPC1 And their pharmaceutically acceptable nontoxic salts wherein R1 is hydrogen, halogen, lower alkyl, hydroxy, nitro or A--NH; A is EQU1 wherein R3 is hydrogen; lower alkyl; halo-(lower alkyl); cycloalkyl of 3 to 11 carbon atoms, unsubstituted or substituted by hydroxy or alkyl of 1 or 2 carbon atoms; cycloalkenyl of 3 to 11 carbon atoms; bicycloalkyl of up to 8 carbon atoms; bicycloalkenyl of up to 8 carbon atoms; aryl of 6 to 10 carbon atoms, unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trifluoromethyl, nitro, amino, alkylsulphonyl of 1 to 4 carbon atoms, and methylenedioxy; azidoaryl of 6 to 10 carbon atoms, azido-(lower alkyl); amino; or thienyl; R4 is lower alkylamino or arylamino of 6 to 10 carbon atoms; B is a direct bond; CH2 ; S--CH2 ; CH=CH; or CO--NH--CH2 ; E is phenyl or phenyl or thenyl, substituted by hydroxy, azido, lower alkyl, lower alkoxy, lower alkylthio or chlorine; and C* is an asymmetric carbon atom, Are useful for their antibacterial activity against both Gram-positive and Gram-negative bacteria.
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(2008/06/13)

Novel acid compounds
Novel therapeutically useful and disinfecting penicillanic and cephalosporanic acid derivatives of the formula: SPC1 Wherein W represents a penicillanic or cephalosporanic acid residue or derivatives thereof and wherein Y represents a carbonamido group N-substituted by a phosphorous or sulfur containing residue or Y represents a phosphorous or sulfur containing substituent, and pharmaceutical and disinfecting compositions containing them and their use and process for the preparation of the said compounds.
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(2008/06/13)

Ureidoacetamido-penicillins
6-(α-3-Acyl-unreidoacetamido)-penicillanic acids and pharmaceutically acceptable non-toxic salts thereof in which the hydrogen atom of the nitrogen atom present in the 3-position is substituted, are effective against Gram-positive and Gram-negative infections, particularly Klebsiella aerobacter infections.
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(2008/06/13)

6-(Substituted-cycloalkylcarboxamide) penicillanic acids
Penicillins of the formula SPC1 Or a pharmaceutically-acceptable, nontoxic salt thereof, Wherein R1 and R2 are the same or different and each is hydrogen, fluorine, chlorine or bromine; or when R2 is hydrogen, R1 can also be cyano, hydroxyl, azido, amino or nitro; or R1 and R2 are bonded to a ring carbon atom and constitute a single oxygen atom; R3 is hydrogen, methyl, chlorine, bromine, cyano, methoxy or carboxyl; and n is 2 to 7; Are useful for their antibacterial activity.
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(2008/06/13)

Novel antibacterial amide compounds and process means for producing the same
Novel organic amide compounds which are N-[6-[(substituted amino)phenyl]-1,2-dihydro-2-oxonicotinyl]penicillin and cephalosporin type compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or cephalosporin or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding N-6-[(substituted amino)phenyl]-1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 6-amino-penicillanic acid, 7-aminocephalosporanic acid, 7-amino-3-methylceph-3-em-4-carboxylic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[6-[(substituted amino)phenyl]-1,2-dihydro-2-oxonicotinyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.
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(2008/06/13)

α-Aminocycloalkylacetamido penicillanic acids and their salts and esters
A class of amino alicyclylmethyl penicillins, their salts, esters, method of preparation and oral compositions containing them are described. The penicillins give high and prolonged blood levels on oral administration and are active against both Gram-positive and Gram-negative bacteria.
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(2008/06/13)

Penicillins
A compound of the formula: SPC1 Or a pharmaceutically acceptable nontoxic salt thereof wherein R1 is hydrogen, straight or branched chain alkyl of 1 to 5 carbon atoms, monoaralkyl of up to 8 carbon atoms, monoaryl, substituted monoaryl, or thienyl; A is moiety of the formula: EQU1 wherein R2, R3, R4, R5, R6 and R7 are the same or different and each is hydrogen, straight or branched chain alkyl of 1 to 5 carbon atoms, monoaralkyl of up to 8 carbon atoms, monoaryl, substituted monoaryl, or thienyl; B is a moiety of the formula: SPC2 Wherein R8, r9 and R10 are the same or different and each is hydrogen, fluorine, chlorine, bromine. iodine, lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulphonyl, sulphamyl, nitro, cyano, di(lower alkyl)amino, lower alkanoylamino, lower alkanoyloxy, lower alkylsulphonylamino, trifluoromethyl or hydroxy; E is oxygen or sulphur; and C is a carbon atom constituting a center of chirality, are useful for their antibacterial activity.
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(2008/06/13)