摘要:
This invention relates to 7-oxo-4-thia-1-aza-bicyclo-[3,2,0]-heptane derivatives, to processes for their synthesis from esters of penicillanic acid 1-oxide, and to intermediate compounds obtained in the synthesis.More particularly, the present invention relates to new and novel compounds of formula (1): ##STR1## wherein R is a hydrogen atom, an alkyl having from 1 to 5 carbon atoms, trichloroethyl, benzyl, p-nitrobenzyl, diphenylmethyl, acetoxymethyl, pivaloyloxymethyl, phthalidyl, trimethylsilyl or a group of formula ##STR2## and R.sup.1 is --CH.sub.2 OH, --CH.sub.2 OCOR.sup.2, --CH.sub.2 OR.sup.3, --COOR.sup.2, --CHO, --CH.sub.2 SH, --CH.sub.2 SR.sup.4, --CH.sub.2 NH.sub.2, --CH.sub.2 NHCOR.sup.2 in which R.sup.2 is an alkyl having from 1 to 5 carbon atoms, aryl, aralkyl or a five- or six-membered heterocyclic ring containing one or more heteroatoms; R.sup.3 is an alkyl having from 1 to 5 carbon atoms, benzyl, trityl, trialkylsilyl; and R.sup.4 is a five- or six-membered heterocyclic ring containing one or more heteroatoms, benzyl, trityl or trialkylsilyl;and to the synthesis of such compounds.Compounds of formula (1) (E+Z isomers) are endowed with antibacterial activity.
摘要:
There are disclosed .beta.-lactam-containing compounds of the formula: ##STR1## where R is hydrogen, lower alkyl, trichloroethyl, acetonyl, benzyl, substituted benzyl, phenyl, substituted phenyl, benzidryl or a residue that will undergo metabolic activation "in vivo" and have favorable pharmacokinetic properties; R.sup.1 is a hydrogen atom, lower alkyl, lower alkoxy, cycloalkyl, or hydroxyalkyl, with the alcoholic function of the hydroxyalkyl being free or protected; Z is hydrogen, halogen, hydroxy, amino, carbamoyloxy, mercapto, pyridinium, OR.sup.2, OCOR.sup.2, NHCOR.sup.2, or SR.sup.3 wherein each of R.sup.2 and R.sup.3 is any of lower alkyl, aryl, or a heterocyclic ring, each of which may be substituted or unsubstituted, and n is 0 or 1. The compounds have broad spectrum antibacterial activity and .beta.-lactamase inhibiting activity. Processes for the production of the .beta.-lactam-containing compounds and various intermediates in the production of those compounds are also disclosed.
摘要:
There are disclosed .beta.-lactam-containing compounds of the formula: ##STR1## where R is hydrogen, lower alkyl, trichloroethyl, acetonyl, benzyl, substituted benzyl, phenyl, substituted phenyl, benzidryl or a residue that will undergo metabolic activation "in vivo" and have favorable pharmacokinetic properties; R.sup.1 is a hydrogen atom, lower alkyl, lower alkoxy, cycloalkyl, or hydroxyalkyl, with the alcoholic function of the hydroxyalkyl being free or protected; Z is hydrogen, halogen, hydroxy, amino, carbamoyloxy, mercapto, pyridinium, OR.sup.2, OCOR.sup.2, NHCOR.sup.2, or SR.sup.3 wherein each of R.sup.2 and R.sup.3 is any of lower alkyl, aryl, or a heterocyclic ring, each of which may be substituted or unsubstituted, and n is 0 or 1. The compounds have broad spectrum antibacterial activity and .beta.-lactamase inhibiting activity. Processes for the production of the .beta.-lactam-containing compounds and various intermediates in the production of those compounds are also disclosed.
摘要:
There is disclosed a process for the manufacture of azetidinones related to nocardicin having the formula ##STR1## wherein R is a saturated or unsaturated alkyl having from 1 to 6 carbon atoms, .alpha.-aminobenzyl, benzyl, free or substituted phenyl, or a free or substituted heterocyclic;R.sub.1 is hydrogen, alkyl having from 1 to 4 carbon atoms, trimethylsilyl, trichloroethyl, benzhydryl or benzyl; andR.sub.2 is a free or substituted phenyl, or a free or substituted heterocyclic, using the same starting compound, but with the possibility of proceeding to the final compound via two somewhat different routes. A number of novel intermediates are also disclosed.
摘要:
7.beta.-acylamino-7.alpha.-methoxy-3-pyrazinylthiomethyl-cephalosporins and their intermediates having high resistance toward .beta.-lactamase enzymes, as well as good antibacterial activity and processes for preparation thereof.
摘要:
A process for preparing cephalosporins of the structure: ##STR1## where R is any of hydrogen, C.sub.1 to C.sub.4 alkyl, t-butoxy, benzyloxy, cyano-methyl, thienyl-methyl, furyl-methyl, naphthyl-methyl, phenyl-methyl, phenoxy-methyl, phenoxy-isopropyl, pyridyl-4-thiomethyl and tetrazolyl-1-methyl;R.sub.1 is any of hydroxyl, C.sub.1 to C.sub.4 alkoxy, benzyloxy, p-methoxy- (or nitro-) benzyloxy, benzhydryloxy, triphenylmethoxy, phenacyloxy, p-halophenacyloxy and trichloroethoxy;Z is any of hydrogen, hydroxyl, --O--CO--C.sub.1 -C.sub.4 alkyl, --O--C.sub.1 -C.sub.4 alkyl, --Br, --I, --Cl, --N.sub.3, --NH.sub.2, --O--CO--CH.sub.3, --O--CO--NH.sub.2 and an -S-mononuclear nitrogen heterocyclic ring,By reacting compounds of the structure: ##STR2## IN WHICH R, R.sub.1, and Z are as above defined; R.sub.2 and R.sub.3 are the same or different and represent a C.sub.1 to C.sub.4 alkyl, a mononuclear aryl ring, --CN, a mononuclear heterocyclic ring or the radicals --COR.sub.4, COOR.sub.4, --PO(OR.sub.4).sub.2, --CO--NHR.sub.4 or R.sub.2 and R.sub.3 together may represent: ##STR3## where T represents >CH.sub.2, -N--R.sub.4 ; and R.sub.4 is lower alkyl, a mononuclear aryl ring or a mononuclear heterocyclic ring,Alone or as mixtures with each other in a suitable solvent at a temperature between -100 and +120.degree. C with a strong base to give compounds of formula I that are a mixture of .DELTA..sub.2 and .DELTA..sub.3 cephem-derivatives from which the .DELTA..sub.3 cephem derivatives can be obtained.
摘要:
A process for the preparation of azetidinone-thiazoline precursors for cephalosporin synthesis. Said precursors are obtained by reducing by means of zinc dust in the presence of aqueous acetic acid a compound of formula ##STR1##
摘要:
A process is disclosed for the preparation of compounds of formula I: ##STR1## wherein R is hydrogen, lower alkyl, trichloroethyl, benzyl, p-nitrobenzyl, acetoxymethyl, pivaloyloxymethyl, phthalidyl, or a --CH(CH.sub.3)OCOOEt group;R.sup.1 is --CH.sub.2 OH, --CHO, --CH.sub.2 SH, --CH.sub.2 NH.sub.2, --CH.sub.2 OCOR.sup.2, --COOR.sup.2, --CH.sub.2 NHCOR.sup.2, --CH.sub.2 OR.sup.3, or --CH.sub.2 SR.sup.4 where R.sup.2 is a lower alkyl, aryl or a heterocyclic ring, R.sup.3 is a lower alkyl, benzyl, or trityl, and R.sup.4 is a five- or six-member heterocyclic ring containing one or more heteroatoms,which comprises reacting a 4-acetoxy azetidinone with a .beta.-thioketoester to form a mixture, reacting said mixture with thionyl chloride followed by reaction with a phosphine and a base, ozonolyzing and heating to obtain the compounds of formula I.
摘要:
7-Acylamino-3-pyrazinylthiomethyl-3-cephem-4-carboxylic acids are disclosed having the general formula: ##STR1## wherein R is an alkyl having from 1 to 5 carbon atoms or ##STR2## wherein Y = Y.sup.1 = HY = y.sup.1 = clY = cl, Y.sup.1 = FY = h,y .sup.1 = cl andIn which n is an integer from 1 to 4, X is O or S, and R.sub.2 is thienyl, phenyl, 1,4-cyclohexadienyl, phenoxy, pyrazinyl and substituted phenyl, thienyl, pyrazinyl and phenoxy, the substituent being selected from the group consisting of hydroxy, chlorine, bromine, and alkyl and alkoxy having from 1 to 4 carbon atoms;R.sub.3 is alkali metal such as sodium or potassium, hydrogen, alkyl having from 1 to 4 carbon atoms, benzyl, trichloroethyl, methoxybenzyl, benzhydryl, pivaloyloxymethyl, and an alkaline earth metal; R.sup.1 may be a pyrazinyl of the general formulae: ##STR3## in which R.sup.4, R.sup.5, R.sup.6 are equal or different and are selected from the group consisting of F, Cl, Br, hydrogen, alkyl, phenyl, cyano, thiocyano, carboxyl, carboxyalkyl, carboxamido, thiocarboxamido, hydroxy, alkoxy, thiol, alkylthio, amino, alkylamino, phenylamino. By the terms alkyl, an alkyl having from 1 to 4 carbon atoms is intended. Processes for making them are also disclosed.The new cephalosporin derivatives of formula (I) exhibit a broad spectrum antibacterial activity and are useful as therapeutic agents in the treatment of infectious diseases caused by gram-negative and gram-positive bacteria.
摘要翻译:公开了具有以下通式的7-酰基氨基-3-吡嗪基硫甲基-3-头孢烯-4-羧酸:其中R是具有1至5个碳原子的烷基或者具有1或5个碳原子的烷基 其中Y = Y1 = HY = Y1 = C1 Y = C1,Y1 = FY = H,Y1 = C1和IN,其中N为1至4的整数,X为O或S,R2为噻吩基, 苯基,1,4-环己二烯基,苯氧基,吡嗪基和取代的苯基,噻吩基,吡嗪基和苯氧基,所述取代基选自羟基,氯,溴以及具有1至4个碳原子的烷基和烷氧基; R3是碱金属如钠或钾,氢,具有1至4个碳原子的烷基,苄基,三氯乙基,甲氧基苄基,二苯甲基,新戊酰氧基甲基和碱土金属; R 1可以是以下通式的吡嗪基:其中R 4,R 5,R 6相同或不同,并且选自F,Cl,Br,氢,烷基,苯基,氰基,硫氰基,羧基, 羧基烷基,甲酰氨基,硫代甲酰胺基,羟基,烷氧基,硫醇,烷硫基,氨基,烷基氨基,苯基氨基。 术语烷基是指具有1至4个碳原子的烷基。 还披露了制作它们的过程。
摘要:
Compounds are disclosed of the formula ##STR1## wherein R.sub.1 represents a hydrogen or chlorine atom, as well as intermediates. These include 4'-deoxy-paromomycin; 4'-deoxy-4'-epi-chloro-paromomycin; 4'-deoxy-4'-epi-chloro-penta-N-benzyloxycarbonylparomomycin; 4'-deoxy-penta-N-benzyloxycarbonylparomomycin; 6,3',2",5",3"',4"'-hexa-O-acetyl-6'-O-benzoyl-4'-deoxy-penta-N-benzyloxycarbonylparomomycin; 6,3',2",5",3"',4"'-hexa-O-acetyl-6'-O-benzoyl-4'-epi-chloro-4'-deoxy-penta-N-benzyloxycarbonylparomomycin; 6,3',2",5",3"',4"'-hexa-O-acetyl-6'-O-benzyl-penta-N-benzyloxycarbonylparomomycin; 6,3',2",5",3"',4"'-hexa-O-acetyl-6'-O-benzoyl-4'-O-[(methylthio)-thiocarbonyl]-penta-N-benzyloxycarbonylparomomycin; and 6,3',2",5",3"',4"'-hexa-O-acetyl-6'-O-benzoyl-4'-O-[(phenylthio)-thiocarbonyl]-penta-N-benzyloxycarbonylparomomycin. The compounds illustrated by the structural formula are useful in treating amoebic dysentery in man and animals.