Cephem compound having catechol or pseudo-catechol structure
AssigneeShionogi & Co., Ltd.
InventorsYasuhiro Nishitani, Toshiaki Aoki, Jun Sato, Kenji Yamawaki, Katsuki Yokoo, Masayuki Sano
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Abstract
The present invention provides a novel compound which has a wide antimicrobial spectrum, and in particular exhibits potent antimicrobial activity against beta-lactamase producing Gram negative bacteria. Specifically, the present invention provides a compound of the formula (I): wherein each symbol is as defined in the specification, or an amino-protected compound when the amino group is present on the ring in the 7-side chain, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the same.
Claims26
A compound of the formula:
- or an amino-protected compound when the amino group is present on the ring in the 7-side chain, or a pharmaceutically acceptable salt thereof,
- wherein
- W is —CH2—, —S— or —O—;
- a) U is —CH2—, —S—, —S(═O)— or —O— when W is —CH2—;
- or
- b) U is —CH2— when W is —S— or —O—;
- L is —CH2—, —CH═CH—, —CH2—CH═CH— or —CH═CH—CH2—;
- R1 is a substituted or unsubstituted carbocyclic group or a substituted or unsubstituted heterocyclic group;
- with regard to R2A and R2B,
- a) R2A is a hydrogen atom, a substituted or unsubstituted amino group, —SO3H, a substituted or unsubstituted amino sulfonyl group, carboxyl group, a substituted or unsubstituted (lower alkyl)oxycarbonyl group, a substituted or unsubstituted carbamoyl group, hydroxyl group, or a substituted carbonyloxy group;
- and R2B is a hydrogen atom, or
- b) R2A and R2B are taken together to form a substituted or unsubstituted methylidene group or a substituted or unsubstituted hydroxyimino group;
- R3 is a hydrogen atom, —OCH3 or —NH—CH(═O);
- R11 is
- E is a group selected from the following formulae which are substituted or unsubstituted on the ring:
- wherein the bond to the quaternary nitrogen atom binds to L, and the other bond binds to R10;
- p is an integer from 1 to 3;
- n is an integer of 1 or 2;
- RX is an optionally substituted lower alkyl group;
- R10 is R12 or a group represented by the formula:
- wherein ring A is a benzene ring, or a 6-membered aromatic heterocyclic group having 1-3 nitrogen atoms;
- k is an integer from 2 to 5;
- each R4 is independently a hydrogen atom, halogen, hydroxyl group, —CN, —C(═O)—R5, —C(═O)—OH, —C(═O)—OR5, or —OR5;
- R5 is a lower alkyl group or halo(lower)alkyl group;
- and
- G is a single bond, a substituted or unsubstituted lower alkylene group, a substituted or unsubstituted alkenylene group or a substituted or unsubstituted alkynylene group;
- B is a single bond or a 5- or 6-membered heterocyclic group containing at least 1-3 nitrogen atoms;
- D is a single bond, —C(═O)—, —O—C(═O)—, —C(═O)—O—, —NR6—, —NR6—C(═O)—, —C(═O)—NR6—, —NR6—C(═O)—NR6—, —O—, —S—, —S(═O)—, —S(═O)2—NR6—, —NR6—S(═O)2—, —NR6—CH2—, —CH2—NR6— or —S(═O)2—;
- each R6 is independently a hydrogen atom or a substituted or unsubstituted lower alkyl group;
- R12 is a hydrogen atom, halogen, hydroxyl group, —SO3H, a substituted or unsubstituted amino group, a substituted or unsubstituted carboxyl group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted amino sulfonyl group, a substituted or unsubstituted lower alkyl group, a substituted or unsubstituted lower alkenyl group, a substituted or unsubstituted lower alkynyl group, a substituted or unsubstituted non-aromatic carbocyclic group or a substituted or unsubstituted non-aromatic heterocyclic group.
Dependencies are inferred from the claim text.