Tricyclic carbapenem compounds
AssigneeTakeda Chemical Industries, Ltd.
InventorsMichiyuki Sendai, Tetsuo Miwa
Life of this patent
Estimating the term…
Abstract
A compound of the formula ##STR1## wherein R.sup.1 is a hydrogen atom or a hydrocarbon group which may be substituted; COOR.sup.2 represents a carboxy group which may be esterified; and ring B is a cyclic group which may be substituted or a pharmaceutically acceptable salt thereof are useful as an antibacterial agent.
Claims7
A compound of the formula ##STR110## wherein R.sup.1 is (1) a hydrogen atom or (2) C.sub.1-6 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-6 cycloalkyl, C.sub.7-10 aralkyl or C.sub.6-10 aryl, the substituent (2) optionally being substituted by 1 to 3 substituents, which may be the same or different, selected from the group consisting of cyano, amino, mono- or di(C.sub.1-4)alkylamino, hydroxy, (C.sub.1-4)alkyloxy, carbamoyloxy, (C.sub.1-4)alkylthio, (C.sub.1-4)alkylsulfonyl, halogen, sulfamoyl, (C.sub.1-4)alkoxycarbonyl and sulfoxy;
- and ring B is five- to seven-membered heterocyclic ring containing one or two hetero atom(s) of S, O and N as the ring constituent atom, and may be substituted by 1 to 3 substituents, which are the same or different, selected from the group consisting of (1) C.sub.1-6 alkyl which may be substituted by 1 to 3 substituents, which are the same or different, selected from the group consisting of four- to six-membered heterocyclic group having 1 to 4 hetero atoms selected from N, O and S, cyano, amino, mono- or di(C.sub.1-4)alkylamino, hydroxy, (C.sub.1-4)alkyloxy, carbamoyloxy, (C.sub.1-4)alkylthio, (C.sub.1-4)alkylsulfonyl, halogen, sulfamoyl, (C.sub.1-4)alkoxycarbonyl, imino, (C.sub.1-4)alkylimino, carbamoyl and mono- or di(C.sub.1-4)alkylcarbamoyl, (2) C.sub.2-6 alkenyl, (3) C.sub.6-10 aryl, (4) C.sub.7-12 aralkyl, (5) C.sub.3-6 cycloalkyl, (6) four- to six-membered heterocyclic group having 1 to 4 hetero atoms selected from N, O and S, (7) cyano, (8) amino, (9) mono- or di(C.sub.1-4)alkylamino, (10) hydroxy, (11) (C.sub.1-4)alkyloxy, (12) carbamoyloxy, (13) (C.sub.1-4) alkylthio, (14) (C.sub.1-4)alkylsulfonyl, (15) halogen, (16) sulfamoyl, (17) (C.sub.1-4)alkoxycarbonyl, (18) imino, (19) (C.sub.1-4)alkylimino, (20) carbamoyl and (21) mono- or di(C.sub.1-4)alkylcarbamoyl, or a pharmaceutically acceptable salt or ester thereof.
A compound of the formula ##STR111## wherein R.sup.1 is (1) a hydrogen atom or (2) C.sub.1-6 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-6 cycloalkyl, C.sub.7-10 aralkyl or C.sub.6-10 aryl, the substituent (2) optionally being substituted by 1 to 3 substituents, which may be the same or different, selected from the group consisting of cyano, amino, mono- or di(C.sub.1-4)alkylamino, hydroxy, (C.sub.1-4)alkyloxy, carbamoyloxy, (C.sub.1-4)alkylthio, (C.sub.1-4)alkylsulfonyl, halogen, sulfamoyl, (C.sub.1-4)alkoxycarbonyl and sulfoxy;
- and A is a lower alkylene or lower alkenylene group which has 1 to 4 hetero atoms of an oxygen atom, sulfur atom optionally oxidized and nitrogen atom, carbonyl group or carbonimidoyl group as the ring constituent element, and A may be further condensed with a cyclic hydrocarbon group selected from the group consisting of cyclopropane, cyclopentane, cyclohexane, cyclopentene, cyclohexene, benzene and naphthalene, or a heterocyclic group having 1 to 4 hetero atoms selected from N, O and S, and the optionally condensed group A may be substituted by 1 to 3 substituents, which are the same or different, selected from the group consisting of (1) C.sub.1-6 alkyl which may be substituted by 1 to 3 substituents, which are the same or different, selected from the group consisting of four- to six-membered heterocyclic group having 1 to 4 hetero atoms selected from N, O and S, cyano, amino, mono- or di(C.sub.1-4)alkylamino, hydroxy, (C.sub.1-4)alkyloxy, carbamoyloxy, (C.sub.1-4)alkylthio, (C.sub.1-4)alkylsulfonyl, halogen, sulfamoyl, (C.sub.1-4)alkoxycarbonyl, imino, (C.sub.1-4)alkylimino, carbamoyl and mono- or di(C.sub.1-4)alkylcarbamoyl, (2) C.sub.2-6 alkenyl, (3) C.sub.6-10 aryl, (4) C.sub.7-12 aralkyl, (5) C.sub.3-6 cycloalkyl, (6) four- to six-membered heterocyclic group having 1 to 4 hetero atoms selected from N, O and S, (7) cyano, (8) amino, (9) mono- or di(C.sub.1-4)alkylamino, (10) hydroxy, (11) (C.sub.1-4)alkyloxy, (12) carbamoyloxy, (13) (C.sub.1-4)alkylthio, (14) (C.sub.1-4)alkylsulfonyl, (15) halogen, (16) sulfamoyl, (17 ) (C.sub.1-4)alkoxycarbonyl, (18 ) imino, (19 ) (C.sub.1-4 )alkylimino, (20) carbamoyl and (21) mono- or di(C.sub.1-4)alkylcarbamoyl, or a pharmaceutically acceptable salt or ester thereof.
The compound which is (5S,6S,7S)-5-[(R)-1-hydroxyethyl]-4-oxo-8-oxa-3-azatricyclo[5.4.0.0.sup.3, 6 ]-undec-1-2-carboxylic acid
The compound which is (5S,6R,7R)-5-[(R)-1-hydroxyethyl]-9-iminomethyl-4-oxo-3,9-diazatricyclo[5. 4.0.0.sup.3,6 ]undec-1-ene-2-carboxylic acid.
(10S,11R,12S)-5-(2-Aminoethoxy)-12-[(R)-1-hydroxyethyl]-13-oxo-14 -azatetracyclo-[8.5.0.0.sup.2,7.0.sup.11,14 ]pentadeca-2,4,6,15 (1)-tetraene-15-carboxylic acid, or a pharmaceutically acceptable salt or ester thereof.
(10S,11R,12S )-5-[2-(1-Iminoethyl)amino]ethoxy]-12-[(R)-1-hydroxyethyl]-13-oxo-14-azatet racyclo-[8.5.0.0.sup.2,7.0.sup.11,14 ]pentadeca-2,4,6,15 (1)-tetraene-15-carboxylic acid, or a pharmaceutically acceptable salt or ester thereof.
(10S,11R,12S )-5-[2-(Iminomethylamino)ethoxy]-12-[(R)-1-hydroxyethyl]-13-oxo-14-azatetra cyclo[8.5.0.0.sup.2,7.0.sup.11,14 ]-pentadeca-2,4,6,15(1)-tetraene-15-carboxylic acid, or a pharmaceutically acceptable salt or ester thereof.
Dependencies are inferred from the claim text.