Patent ID: 6599895
Filing Date: 2003-07-29
Classification: A61P,C07D,Y02P

Abstract:
A &bgr;-lactam compound of the formula (1): whereinR1 is a lower alkyl group or a lower alkyl group being substituted by a hydroxy group; R2 is a hydrogen atom or a lower alkyl group; X is an oxygen atom or a sulfur atom; R3 is a hydrogen atom, a pharmaceutically acceptable metal, or a protecting group for. a carboxyl group selected from the group consisting of a straight chain or branched chain lower alkyl group having 1 to 5 carbon atoms, a halogeno-lower alkyl group having 1 to 5 carbon atoms, an alkoxymethyl group having 1 to 5 carbon atoms in the alkoxy moiety, an aliphatic acyloxymethyl group having 1 to 5 carbon atoms in the acyloxy moiety, an aralkyl group, a substituted aralkyl group selected from p-methoxybenzyl, o-nitrobenzyl and p-nitrobenzyl, a lower alkenyl group having 3 to 7 carbon atoms, a benzhydryl group, and a phthalidyl group, or R3 represents an electron when the W ring contains a quaternary nitrogen; Ring W is a 6- or 7-membered heterocyclic ring made up of carbon atoms and 1 to 2 nitrogen atoms and having 1 to 3 double bonds, the carbon atoms of which ring may optionally include 1 to 2 carbonyl carbon atoms at any position which is chemically possible, and the carbon atoms of Ring W are not substituted, and the nitrogen atoms of Ring W are not substituted or have the following substituents: a) Ra (Ra is a lower alkyl group or a lower alkyl group substituted by a member selected from (1) an aryl group, (2) a hydroxy group, (3) a lower alkoxy group, (4) a lower alkoxy group being substituted by a hydroxy group, (5) a lower alkoxy group being substituted by an amino group, (6) a lower alkylcarbonyloxy group, (7) a lower alkoxycarbonyl group, (8) a lower alkylcarbonyl group, (9) an amino group, (10) a mono- or di-(lower alkyl)amino group wherein said lower alkyl group optionally has a substituent selected from an aminocarbonyl group having optionally a lower alkyl substituent, a hydroxy group, a carboxyl group and a lower alkylcarbonyl group, (11) a guanidino group, (12) a carboxyl group, (13) an aminocarbonyl group, (14) a mono- or di-(lower alkyl)aminocarbonyl group wherein said lower alkyl group has optionally a substituent selected from an aminocarbonyl group having optionally a lower alkyl substituent, a hydroxy group, a carboxyl group and a lower alkylcarbonyl group, (15) a halogen atom, (16) a cyano group, (17) an alkylamidino group having 1 to 3 carbon atoms, and (18) a guanidinocarbonyl group; or a cycloalkyl group, or a cycloalkyl group substituted by a member selected from (1) an aryl group, (2) a hydroxy group, (3) a lower alkoxy group, (4) a lower alkoxy group being substituted by a hydroxy group, (5) a lower alkoxy group being substituted by an amino group, (6) a lower alkylcarbonyloxy group, (7) a lower alkoxycarbonyl group, (8) a lower alkylcarbonyl group, (9) an amino group, (10) a mono- or di-(lower alkyl)amino group wherein said lower alkyl group optionally has a substituent selected from an aminocarbonyl group having optionally a lower alkyl substituent, a hydroxy group, a carboxyl group and a lower alkylcarbonyl group, (11) a guanidino group, (12) a carboxyl group, (13) an aminocarbonyl group, (14) a mono- or di-(lower alkyl)aminocarbonyl group wherein said lower alkyl group has optionally a substituent selected from an aminocarbonyl group having optionally a lower alkyl substituent, a hydroxy group, a carboxyl group and a lower alkylcarbonyl group, (15) a halogen atom, (16) a cyano group, (17) an alkylamidino group having 1 to 3 carbon atoms, and (18) a guanidinocarbonyl group; b) â€”CH&boxH;NH or â€”CH&boxH;NPb (Pb is a protecting group for an amino group selected from the group consisting of a lower alkoxycarbonyl group having 1 to 5 carbon atoms in the alkoxy moiety, a halogenoalkoxycarbonyl group having 1 to 5 carbon atoms in the alkoxy moiety, a lower alkenyloxycarbonyl group having 3 to 7 carbon atoms, an aralkyloxycarbonyl group, a substituted aralkyloxycarbonyl group selected from p-methoxybenzyloxycarbonyl, o-nitrobenzyloxycarbonyl and p-nitro-benzyloxycarbonyl, and a trialkylsilyl group); c) â€”C(Ra)&boxH;NH or â€”C(Ra)&boxH;NPb (Ra and Pb are as defined above); provided that when said nitrogen atom of Ring W has a double bond, then said nitrogen atom may be a quaternary one having 1 substituent as mentioned above, and when the nitrogen atom of Ring W has no double bond, then said nitrogen atom may be a quaternary one having 2 substituents as mentioned above; or a pharmaceutically acceptable salt thereof, or a non-toxic ester thereof.