摘要:
Penicillin sulfoxide esters having the sulfoxide group in the .alpha.-configuration are reacted with an N-chloro halogenating agent at a temperature between about 70.degree. C. and about 120.degree. C. in the presence of an alkylene oxide and preferably also calcium oxide to produce 2-chlorosulfinyl-azetidin-4-one intermediates. The chlorosulfinyl intermediates are then treated with a Friedel-Crafts catalyst, for example, stannic chloride to provide a 3-exomethylenecepham .beta.-sulfoxide. The latter compounds are useful in the preparation of 3-alkoxy and 3-halo substituted cephalosporin antibiotic compounds.
摘要:
A novel 4-(2'-benzothiazolyldithio)-3-imidoazetidin-2-one of the formula ##STR1## in which X is chloro or bromo and R.sub.2 is methylene or oxygen is ring-closed to the corresponding 3-exomethylenecepham or 3-"oxo" cepham by treatment with sodium or potassium iodide at a temperature of from about 40.degree. C. to about 80.degree. C.
摘要:
A compound represented by ##STR1## is treated with a base to give an antibacterial cephem compound represented by ##STR2## (wherein A is amino or substituted amino;Cob is carboxy or protected carboxy;Rs is substituted thio;Y is an electron-attracting group selected from acyloxy, halogen, cyano, nitro, and nitroso; andThe dotted line shows .DELTA..sup.2 or .DELTA..sup.3).
摘要:
Process for the preparation of 7-substituted amino-desacetoxycephalosporanic derivatives comprising converting a 6-substituted amino-penicillanic acid sulfoxide into an anhydride of a 6-substituted amino-penicillanic acid sulfoxide, heating the said acid anhydride intermediate at a temperature up to at most 160.degree. C in a dry inert organic solvent with an anhydrous acid which is capable of causing ring expansion of the penam ring to a .DELTA..sup.3 -cephem ring, in the presence of a silicon-containing compound capable of (a) removing water formed during the ring enlargement of the penam structure fast enough to prevent water hydrolysis of the acid anhydride moiety present and (b) forming neutral or basic products on hydrolysis, the aforesaid acid being strong enough not to be, or not to a substantial extent to be, silylated under the reaction conditions employed, and hydrolyzing the resulting compound in situ to form the .DELTA..sup.3 -7-substituted amino-desacetoxycephalosporanic acid as such or as a salt, such as alkali metal, alkaline earth metal or amine salt and to the novel sulfoxide acid anhydrides formed therein.
摘要:
A process for producing a desacetoxy cephalosporanic acid represented by formula (III), ##SPC1##wherein R.sub.1 is acyl, and R.sub.2 is alkyl, aryl or arylalkyl, which comprises: heating a penicillin sulfoxide of the formula (I), ##SPC2##wherein R.sub.1 and R.sub.2 are the same as hereinbefore defined at 50.degree. to 160.degree.C in an inert organic solvent in the presence of a sulfonate represented by formula (II), ##EQU1## wherein A is R.sub.5 --N--R.sub.6, R.sub.5 --N--O--R.sub.6, S--R.sub.6, R.sub.5 --S.fwdarw.O, and R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are lower alkyl, phenyl, benzyl or phenethyl, R.sub.7 is 1-12C alkyl, phenyl, 1-12C alkyl-substituted-phenyl, naphthyl, 1-12C alkyl-substituted naphthyl, halogen-substituted phenyl and wherein when A is R.sub.5 --N--R.sub.6 or R.sub.5 --N--O--R.sub.6, R.sub.3, R.sub.4 and R.sub.5 may form a heterocyclic ring together with the nitrogen atom, and when A is S--R.sub.6, R.sub.3 and R.sub.4 may form a heterocyclic 4-5C polymethylene ring or R.sub.6 and R.sub.7 may bond to form a polymethylene link.
摘要翻译:一种制备由式(III)表示的脱乙酰氧基头孢菌酸的方法,其中R1是酰基,R2是烷基,芳基或芳烷基,其包括:加热式(I)的青霉素亚砜,其中R1和R2相同 在式(II)表示的磺酸盐存在下,在惰性有机溶剂中,在50-160℃下定义R 3 ANGLE A + - - - SO 3 - (II)R 4,其中A是 R5-N-R6,R5-NO-R6,S-R6,R5-S-> O,R3,R4,R5和R6是低级烷基,苯基,苄基或苯乙基,R7是1-12C烷基, 1-12C烷基取代的苯基,萘基,1-12C烷基取代的萘基,卤素取代的苯基,其中当A是R5-N-R6或R5-NO-R6时,R3,R4和R5可以形成杂环 与氮原子一起,当A为S-R6时,R3和R4可以形成杂环的4-5C多亚甲基环,或者R6和R7可以键合形成多亚甲基连接。
摘要:
A new azetidine derivative of the formula: ##EQU1## wherein R.sub.1 represents a penicillin- or cephalosporin-amido group, R.sub.2 represents one of the groups of the following formulae: ##EQU2## wherein R.sub.4, R.sub.5 and R.sub.6 are the same or different and each represents a hydrogen atom or a lower alkyl or alkenyl group, n represents 2 or 3 and - in case formula IIB represents a phenyl group - this group may carry one to four further substituents selected from the group consisting of halogen atoms and lower alkyl, lower alkenyl and phenyl groups,R.sub.3 represents an amino group of the formula ##EQU3## wherein R.sub.7 represents a hydrogen atom or a lower alkyl group and R.sub.8 represents a lower alkyl group, orR.sub.3 represents a N,N'-disubstituted hydrazino group wherein the substituents are lower alkyl groups, e.g. the N,N'-diisopropylhydrazino group, orR.sub.3 represents the group --OR.sub.9, wherein R.sub.9 represents a hydrogen atom, a lower alkyl group, which group may be substituted by 1 to 3 halogen atoms or by 1 or 2 phenyl groups, werein the phenyl groups may be substituted by a methoxy or a nitro group, or R.sub.9 represents a phenacyl group or a salt-forming cation,And corresponding azetidine derivatives of formula I wherein the double bond in the propenyl side chain has been shifted from the 2- to the 1-position, which are versatile intermediates in the process of preparing cephalosporanic and penicillanic derivative.
摘要:
The invention relates to a process for the preparation of 7 Beta -acylamido-3-methylceph-3-em-4-carboxylic acid esters from compounds of the penicillin type, in particular, 6 Beta acylamido penicillanic acid 1-oxide esters, in the presence of a catalyst selected fron a mono-O-substituted orthophosphoric acid, an O,O-di(aryl substituted) orthophosphoric acid, a salt or complex formed from a nitrogen base having a pKb of not less than 4 and a mono-O-substituted orthophosphoric acid or an O,O-di(aryl substituted) orthophosphoric acid. The salt or complex may be formed in situ in the reaction mixture.
摘要:
Cephalexin was produced by hydrolysis of its methoxymethyl ester which in turn was produced by reaction of 2-phenylglycine chloride hydrochloride with an imino ether of methoxymethyl 7phenoxyacetamido-3-methyl-ceph-3-em-4-carboxylate which had been prepared by reaction of an alcohol with the corresponding iminochloride made by treatment with PCl5 of methoxy-methyl 7phenoxyacetamido-3-methylceph-3-em-4-carboxylate. The last was made by thermal rearrangement of the methoxymethyl ester of phenoxymethylpenicillin sulfoxide.
摘要:
Novel 2-substituted thiazoline azetidinones are obtained from 2,6-disubstituted thiazoline azetidinones by treatment with lead tetraacetate followed by hydrolysis. The novel 2-substituted thiazoline azetidinones are reduced by treatment with aluminum amalgam or sodium borohydride to the corresponding thiazolidine azetidinones which are useful in the synthesis of penicillins and cephalosporins.