IL42529A - Preparation of 3-methyl-cephem,3-nitrooxy(or acyloxy)-3-methyl-cephem and 2-nitrooxy(or acyloxy)methyl-2-methyl-penam derivatives and certain novel 3-nitrooxy-3-methyl-cephem derivatives - Google Patents

Claims (1)

1. CLAIMS 1. Process for converting a cephara compound which comprises reacting a compound of: the formula I with a compound of the formula AgQ, to obtain a mixture comprising a compound of the formula II 0 a compound of the formula III and' a" compound of the formula IV 42529/2 in which, in the above formulae, R is the residue of an imide derived from a dicarboxylic acid, R^ is a carboxy protecting group, X is chlorine or bromine * d Q, is 0 -0N02 or -OCR2 wherein is ^-C^ alkyl or C^-C^ cyclo-alkyl, and optionally, isolating the individual compounds of formulas II, III and IV above and if desired, heating the compound of formula III when Q is -ONC^ at a temperature of from about 80°C. to about 175°C. for a period sufficient to denitrate said nitrooxycepham. to obtain a compound of the formula II. 42529/2 f 3 '< '■ 2. Process of claim 1, in which 0. is 0 It 3. Process t claim 2, in which R is c2_Ci+ alk lene, c2-cij. alkenylene, -CHg-Y-CHg- in which Y is oxygen or sulfur, 1,2-cyclohexylene, 1, 2-phenylene , 1,2-cyclohexenylene , or a substituted derivative of any of the above having from 1 to substituents selected from the group consisting of C^C^ alkyl, ^^-^ alkoxy, and nitro. Process of claim 3> in which R is C^-C^ alkylene, C2-C^ alkenylene, -CH2- -CH2- in which Y is oxygen or sulfur, 1,2-cyclohexylene, 1, 2-phenylene, or 1 , 2-cyclohexenylene . 5. Process of claim 2, 3 or , in which R^ is the residue of an ester group which is removable by hydro genation or acid treatment. 6. Process of claim 5, in which R^ is C-^-C^ alkyl, 2,2,2-trihaloethyl, benzyl, p-nitrobenzyl , succinimidomethyl, phthaliraidomethyl, p-methoxybenzyl, benzhydryl, C^-Cg-alkanoyloxymethyl , or phenacyl. 7. Process of any one of claims 2-6, in which X is chloro. -8ϊ -Process.; of. any- one- f-claims- 2 77 in wh c 42529/2 R2 is methyl. 9„ Process of any one of claims -8, in which R is 1,2-phenylene, 10. Process of any one of claims 6-9, n which R-L is methyl, benzyl, p-nitrobenzyl , p-methoxybenzyl , benzhydryl, or 2 , 2 , 2-trichloroethyl. 11. Process of claim 10, in which R^ is p-nitrobenzyl or p-methoxybenzyl. 12. Process of claim 1, in which Q, is -0N02. 13„ Process of claim 12, in which R is C—-C^ allcylene, alkenylene, -CH2-Y-CH2- in which Y is oxygen or sulfur, 1 , 2-cyclohexylene , 1,2-phenylene, 1,2-cyclohexenylene , or a substituted derivative of any of the above having from 1 to substituents selected from the group consisting of alkoxy, and nitro. l^. Process of claim 13, in which R is C2-C^ alkylene, ^z~C alkenylene» -CH2-Y-CH"2- in which Y is oxygen or sulfur, 1 , 2-cyclohexylene , 1,2-phenylene, or 1, 2-cyclohexenylene . 15. Process of claim 12, lj| or l^, in which R^ is the residue of an ester group wh,ich is removable b hydrogenat'ioh or acid treatment. 16 Process of claim 15, in which R^ is C-^-C^ alkyl, 2 , 2 , 2-trihaloethyl , 2-ibdoethyl, benzyl, p-nitrobenzyl, succiminidomethyl, phthalimidomethyl, p-methoxybenzyl, benzhydryl, C2-C^-alkanoyloxymethyl, or phenacyl. 17. Process of any one of claims 12-16, in which X is chloro, 18. Process of any one of claims 12-17, in 42529/2 which R is 1 , 2-phenylene . 19. Process of any one of claims 16-18, in which R]_ is -methyl--* benzyl* p-nitrobenzyl , p-methoxybenzyl, benzhydryl, or 2 , 2 , 2-trichloroethyl . 20. Process of claim 19, in which is p-nitrobenzyl or p-raethoxy. 21. A compound . of■ the formula V 0 in .which R is 1 , 2-phenylene and is nitrobenzyl, methox ^benzyl , or C^-C^-lower alkyl. 22. Compound of claim 21, in which R^ is methyl. 23. Compound of claim 21, in which R^ is p-nitrobenzyl or p-methoxybenzyl. 24.. Process of claim 2, substantially as herein defined. 25. Compounds of formula II, III- or IV as defined in claim 2 when prepared by the process of any one of claims 2 to 11. 26. Process of claim 12, substantially as herein described. * 42529/2 27. Compounds of the formula II, III or IV as defined in claim 12, when prepared by the process of any one of claims 12 to 20. 28. Compounds of the formula V as defined in claim 21, substantially as herein described.