C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/104
C07D 501/24 (2006.01) C07D 277/20 (2006.01)
Patent
CA 1177481
ABSTRACT OF THE DISCLOSURE The invention provides N-substituted thiazolyl oxy-imino substi- tuted cephalosporins of formula I (I) Image wherein R is 1) -OR2 in which R2 is a hydrogen atom or a saturated or un- saturated C1-C6 branched or straight chain aliphatic hydrocarbon group which is unsubstituted or substituted by a substituent selected from the group consisting of a) cyano; b) -COOR4 in which R4 is hydrogen, C1-C6 alkyl or a carboxy-protecting group and c) Image in which each of the groups R5 and R6, which may be the same or different, represents a hydrogen atom, a C1-C6 alkyl or an aliphatic acyl group or, when R5 is hydrogen, R6 may be also an amino-protecting group or 2) Image wherein R5 and R6 are as defin- ed above; R1 represents a hydrogen atom or an amino-protecting group; R3 represents a hydrogen atom, a hydroxy-protecting group or a branched or straight chain saturated or unsaturated C1-C6 aliphatic hydrocarbon group, which may be unsubstituted or substituted by one or more substituents select- ed from a')hydroxy; b') cyano; c') C1-C6 alkyl, d') Image in which R5 and R6 are as defined above; e') -COOR7 in which R7 is hydrogen, C1-C6 alkyl, aryl, indanyl, acetoxymethyl or a carboxy-protecting group or f') halo-C1-C5 alkyl; n is zero, 1 or 2; Y is hydrogen; halogen; hydroxy; C1-C6 alkoxy; C1-C6 alkyl or a group -CH2-Z in which Z is 1) -OCOCH3 or 2) Image where R' is hydrogen. C1-C6 alkyl, carboxy, cyano or carbamoyl; or 3) -S-Het, wherein Het represents A) a pentatomic or hexatomic heteromonocyclic ring containing at least one double bond and at least one hcteroatom selected from N,S, and O, which ring is unsubstituted or substituted by one or more substi- tuents selected from: a") hydroxy, C1-C6 alkoxy, halogen, C2-C6 aliphatic acyl; b") C1-C6 alkyl which is unsubstituted or substituted by one or more substituents selected from hydroxy and halogen; c") C2-C6 alkenyl which is unsubstituted or substituted by one or more substituents selected from hydroxy and halogen; d") -S-R8 wherein R8 is hydrogen or C1-C6 alkyl or -S-CH2-COOR4 wherein R4 is as defined above; e") -(CH2)mCOOR4 or -CH=CH-COOR4 wherein m is 0, 1, 2 or 3 and R4 is as defined above; -(CH2)mCN or -(CH2)-CONH2 wherein m is as defined above -(CH2)mSO3H wherein m is as de- fined above; or f") -(CH2)m Image wherein m, R5 and R6 are as defined above, or B) a heterobicyclic ring containing at least two double bonds where- in each of the condcnsed heteromonocyclic rings, being the same or different, is a pentatomic or hexatomic heteromonocyclic ring containing at least a heteroatom selected from N, S and O, the heterobicylic ring being unsubsti- tuted or substituted by one or more substituenes selected from a", b", c", d", e" and f" above; and X is a free or esterfied carboxy group; and the pharmaceutically and veterinarily acceptable salts thereof. The compounds display high antibacterial activity in animals and in humans against both Gram-positive and Gram-negativc bacteria.
365302
Alpegiani Marco
Giudici Franco
Meinardi Giuseppe
Nannini Giuliano
Perrone Ettore
Farmitalia Carlo Erba S.p.a.
Fetherstonhaugh & Co.
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