Patent ES-8602013-A1 (ES)
Title: Antibacterial penem derivatives.
IPC: C07D499/00
Filed: 1984-12-28
Abstract: EP--99059 A - A compound of the general formula I in which R represents a hydrogen atom or a carboxyl esterifying group, removable by hydrolysis, by photolysis, by reduction or by enzyme action to give the free acid R1 represents a phenyl, naphthyl or thienyl group bonded at a ring carbon atom to the oxygen atom attached to the 2-position of the penem ring structure, the group R1 being unsubstituted or substituted by one, two or three substituents, which may be the same or different, selected from halogen atoms and-OH, -NH2, -NO2, -CN, -N3, R3-, R3O-, R3S-, R3-SO-, R3-SO2-, R3-CO-, R3O-CO-, R3-CO-O-, H2N-CO-, gps. (1)- (22) -CF3, -SCF3, -SOCF3, -SO2CF3 and HO-CO groups, in which R3, R3' and R3'' each represent an alkyl group having from 1 to 4 carbon atoms, R3, R3' and R3'' being the same or different, - but not more than one should be selected from (a) -OH and -NH2 groups and not more than one should be selected from (b) -CN, - R3-CO-, R3O-CO-, R3-SO-, and R3-SO2-groups, R2 represents (i) a straight or branched chain alkyl group having from 1 to 5 carbon atoms, which is substituted by one or more substituents, which may be the same or different, selected from the following: (a) alkenyl and alkynyl groups having up to 4 carbon atoms (b) cycloalkyl and cycloalkenyl groups having from 3 to 7 carbon atoms (c) a phenyl group, which may be unsubstituted or substituted by one or more substituents, which may be the same or different, selected from alkyl, alkylthio and alkoxy groups having up to 4 carbon atoms halogen atoms, trifluoromethyl groups- cyano groups- carboxyl groups groups of the formula -COOR4 in which R4 represents an alkyl group having up to 4 carbon atoms amido and sulphonamide groups, groups of the formula -NR6R5 wherein R5 and R6 which by be the same or different, each represent a hydrogen atom or a group -COR4, -SO2R4 or R4, in which R4 is as defined above (d) trifluoromethyl and 2,2,2-trifluoroethyl groups (e) halogen atoms, (f) hydroxy groups, alkoxy groups EPAB- EP--99059 B A compound of the general formula I in which R represents a hydrogen atom or a carboxyl esterifying group, removable by hydrolysis, by photolysis, by reduction or by enzyme action to give the free acid R1 represents a phenyl, naphthyl or thienyl group bonded at a ring carbon atom to the oxygen atom attached to the 2-position of the penem ring structure, the group R1 being unsubstituted or substituted by one, two or three substituents, which may be the same or different, selected from halogen atoms and-OH, -NH2, -NO2, -CN, -N3, R3-, R3O-, R3S-, R3-SO-, R3-SO2-, R3-CO-, R3O-CO-, R3-CO-O-, H2N-CO-, gps. (1)- (22) -CF3, -SCF3, -SOCF3, -SO2CF3 and HO-CO groups, in which R3, R3' and R3'' each represent an alkyl group having from 1 to 4 carbon atoms, R3, R3' and R3'' being the same or different, but not more than one should be selected from (a) -OH and -NH2 groups and not more than one should be selected from (b) -CN, R3-CO-, R3O-CO-, R3-SO-, and R3-SO2-groups, R2 represents (i) a straight or branched chain alkyl group having from 1 to 5 carbon atoms, which is substituted by one or more substituents, which may be the same or different, selected from the following: (a) alkenyl and alkynyl groups having up to 4 carbon atoms (b) cycloalkyl and cycloalkenyl groups having from 3 to 7 carbon atoms (c) a phenyl group, which may be unsubstituted or substituted by one or more substituents, which may be the same or different, selected from alkyl, alkylthio and alkoxy groups having up to 4 carbon atoms halogen atoms, trifluoromethyl groups- cyano groups- carboxyl groups groups of the formula -COOR4 in which R4 represents an alkyl group having up to 4 carbon atoms amido and sulphonamide groups, groups of the formula -NR6R5 wherein R5 and R6 which by be the same or different, each represent a hydrogen atom or a group -COR4, -SO2R4 or R4, in which R4 is as defined above (d) trifluoromethyl and 2,2,2-trifluoroethyl groups (e) halogen atoms, (f) hydroxy groups, alkoxy groups GBAB- GB2122619 B A compound of the general formula (I) in which R represents a hydrogen atom or a carboxyl esterifying group, R1 represents a phenyl, naphthyl, thienyl, pyridyl, quinolyl or isoquinolyl group bonded at a ring carbon atom to the oxygen atom attached to the 2-position of the penem ring structure, a group R1 being unsubstituted or substituted by one, two or three substituents, which may be the same or different, selected from halogen atoms and -OH, -NH2, -NO2, -CN, -N3, R3-, R3O-, R3S-, R3-SO2-, R3-CO-, R3O-CO-, R3-CO-O-, H2N-CO-, (II)-(X), R3-CO-NH-, NH2-CO-NH-, R3-SO2-NH-, NH2-SO2-NH-, H2N-SO2-, (XI)-(XVIII), -CF3, -SCF3, -SOCF3, -SO2CF3 and HO-CO-groups, in which R3, R3', and R3'' each repr'resents an alkyl group having from 1 to 4 carbon atoms, R3, R3' and R3'' being the same or different and R2 represents (i) a hydrogen atom, (ii) a straight or branched chain alkyl group having from 1 to 15 carbon atoms, and which is unsubstituted or is substituted by one or more substituents, which may be the same or different, selected from the following: (a) alkenyl and alkynyl groups having up to 4 carbon atoms (b) cycloalkyl and cycloalkenyl groups having from 3 to 7 carbon atoms (c) aryl groups which may be unsubstituted or substituted by one or more substituents, which may be the same or different selected from alkyl, alkylthio and alkoxy groups having up to 4 carbon atoms halogen atoms trifluoromethyl groups cyano groups carboxyl groups, groups of the formula -COOR4 in which R4 represents an alkyl group having up to 4 carbon atoms, amido and sulphonamido groups groups of the formula NR5R6 in which R5 and R6, which may be the same or different, each represents a hydrogen atom or a group -COR4, -SO2R4 or R4 is defined as above: (d) trifluoromethyl and 2,2,2-trifluoroethyl groups (e) halogen atoms (f) free hydroxy groups and substituted hydroxy groups (g) cyano and azido groups and (h) amino groups and groups of the formula NR5R6 in which R5 and R6 are as defined i - GB2122619 B A compound of the general formula (I) in which R represents a hydrogen atom or a carboxyl esterifying group, R1 represents a phenyl, naphthyl, thienyl, pyridyl, quinolyl or isoquinolyl group bonded at a ring carbon atom to the oxygen atom attached to the 2-position of the penem ring structure, a group R1 being unsubstituted or substituted by one, two or three substituents, which may be the same or different, selected from halogen atoms and -OH, -NH2, -NO2, -CN, -N3, R3-, R3O-, R3S-, R3-SO2-, R3-CO-, R3O-CO-, R3-CO-O-, H2N-CO-, (II)-(X), R3-CO-NH-, NH2-CO-NH-, R3-SO2-NH-, NH2-SO2-NH-, H2N-SO2-, (XI)-(XVIII), -CF3, -SCF3, -SOCF3, -SO2CF3 and HO-CO-groups, in which R3, R3', and R3'' each repr'resents an alkyl group having from 1 to 4 carbon atoms, R3, R3' and R3'' being the same or different and R2 represents (i) a hydrogen atom, (ii) a straight or branched chain alkyl group having from 1 to 15 carbon atoms, and which is unsubstituted or is substituted by one or more substituents, which may be the same or different, selected from the following: (a) alkenyl and alkynyl groups having up to 4 carbon atoms (b) cycloalkyl and cycloalkenyl groups having from 3 to 7 carbon atoms (c) aryl groups which may be unsubstituted or substituted by one or more substituents, which may be the same or different selected from alkyl, alkylthio and alkoxy groups having up to 4 carbon atoms halogen atoms trifluoromethyl groups cyano groups carboxyl groups, groups of the formula -COOR4 in which R4 represents an alkyl group having up to 4 carbon atoms, amido and sulphonamido groups groups of the formula NR5R6 in which R5 and R6, which may be the same or different, each represents a hydrogen atom or a group -COR4, -SO2R4 or R4 is defined as above: (d) trifluoromethyl and 2,2,2-trifluoroethyl groups (e) halogen atoms (f) free hydroxy groups and substituted hydroxy groups (g) cyano and azido groups and (h) amino groups and groups of the formula NR5R6 in which R5 and R6 are as defined i USAB- US4738959 A Penem derivs. of formula (I) and salts are new. - In (I) R is H or carboxyl esterifying gp R1 is Ph, naphthyl, thienyl, bonded at ring C to 0 at 2-position of penem, opt. substd.: R2 is 3-7C cycloalkyl opt. substd. or Ph opt. substd. - (I) may be obtd e.g. by acylating (II) and opt further conversions.