Claims
- 1. A compound represented by formula IIA: ##STR16## and pharmaceutically acceptable salts thereof, wherein R.sup.21 represents --COR.sup.26 or --CO.sub.2 R.sup.26 ;
- R.sup.23 is hydrogen;
- R.sup.22, and R.sup.24 are independently selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, nitro, hydroxy, amino, carboxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio and C.sub.2-6 alkoxycarbonyl, provided that at least one of R.sup.22, and R.sup.24 is other than hydrogen, and R.sup.26 is selected from the group consisting of C.sub.3-7 cycloalkyl, aryl (C.sub.1-6)alkyl, aryl (C.sub.2-6)alkenyl, aryl(C.sub.2-6)alkynyl, heteroaryl(C.sub.1-6)alkyl, selected from the group consisting of indolyethyl, indolylpropyl or thienylethyl, and heteroaryl (C.sub.2-6)alkenyl selected from thienylvinyl, any of which groups can be substituted by hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkoxy (C.sub.1-6) alkoxy and C.sub.2-6 alkoxycarbonylamino (C.sub.1-6)-alkyl and wherein said aryl group is selected from phenyl and naphthyl.
- 2. A compound represented by formula IIB: ##STR17## and pharmaceutically acceptable salts thereof, wherein W.sup.1 represents oxygen, sulphur or N--A.sup.13 ;
- A.sup.11 and A.sup.12 are independently selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, nitro, hydroxy, amino, carboxy, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkyl (C.sub.1-6)alkyl, C.sub.3-7 cycloalkyl(C.sub.1-6)alkyl, aryl, aryl (C.sub.1-6)alkyl, C.sub.1-6 alkoxy, C.sub.2-6 alkenyloxy, C.sub.1-6 alkylthio, C.sub.2-6 alkenylthio, C.sub.2-6 alkylcarbonyl, arylcarbonyl and C.sub.2-6 alkoxycarbonyl; or A.sup.11 and A.sup.12 together represent a fused benzo ring, which can be substituted by nitro or C.sub.1 -C.sub.6 alkoxy;
- A.sup.13 is selected from the group consisting of hydrogen, C.sub.1-6 alkyl and aryl (C.sub.1-6) alkyl;
- B represents a bond or a carbonyl group (C.dbd.O); and R.sup.33 is hydrogen
- R.sup.32, and R.sup.34 are independently selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, nitro, hydroxy, amino, carboxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio and C.sub.2-6 alkoxycarbonyl, provided that at least one of R.sup.32, and R.sup.34 is other than hydrogen and wherein aryl is selected from phenyl or naphthyl.
- 3. A compound represented by formula IIC: ##STR18## and pharmaceutically acceptable salts thereof, wherein A.sup.21 is selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, nitro, hydroxy, amino, carboxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.2-6 alkylcarbonyl, arylcarbonyl and C.sub.2-6 alkoxycarbonyl;
- B represents a bond or a carbonyl group (C.dbd.O); and
- R.sup.43 is hydrogen,
- R.sup.42, and R.sup.44 are independently selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, nitro, hydroxy, amino, carboxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio and C.sub.2-6 alkoxycarbonyl, provided that at least one of R.sup.42, and R.sup.44 is other than hydrogen.
- 4. A compound selected from the group consisting of:
- 3-benzyloxycarbonyl-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(2-phenylethoxy)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(3-phenylpropoxy)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[2-(3-hydroxyphenyl)ethoxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[3-(4-hydroxyphenyl)propoxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[2-(2-hydroxyphenyl)ethoxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-3-cyclopropylmethoxycarbonyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline
- 7-chloro-2,4-dioxo-3-[2-(4-hydroxyphenyl)ethoxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(3-hydroxyphenylmethoxy)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(pyrid-2-ylmethoxy)carbonyl-1,2,3,4-tetrahydroquinoline;
- 2,4-dioxo-3-[3-(4-hydroxyphenyl)propoxy]carbonyl-7-nitro-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(2-hydroxyethoxy)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(3-thienyl)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(2-furyl)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(2-thienyl)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-3-(2,5-dimethyl-3-furyl)carbonyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(5-methyl-2-furyl)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[2-(5-nitrobenzofuryl)carbonyl]-1,2,3,4-tetrahydroquinoline;
- 3-[2-(benzofuryl)carbonyl]-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 3-[2-(benzo[b]thienyl)carbonyl]-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 3-benzylcarbonyl-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(5-methyl-2-thienyl)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(3-methyl-2-thienyl)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-3-(2,5-dimethyl-3-thienyl)carbonyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[2-(3-thienyl)ethenyl]carbonyl-1,2,3,4-tetrahydroquinoline;
- 3-(5-bromo-2-thienyl)carbonyl-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(1-methylpyrrol-2-yl)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(1-methylpyrrol-3-yl)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(1-methylindol-3-yl)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-3-cyclopropylcarbonyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(5-methyl-2-furyl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(5-ethyl-2-furyl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(1-methylpyrrol-2-yl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(2-furyl)-1,2,3,4-tetrahydroquinoline;
- 3-(4-benzoyl-1-methylpyrrol-2-yl)-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 3-(5-benzoyl-1-methylpyrrol-2-yl)-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[2-(5-methoxyindol-3-yl)ethoxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[3-(3-methoxyphenyl)prop-2-ynyloxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(3-indol-3-ylpropoxy)carbonyl-1,2,3,4-tetrahydroquinoline;
- 3-[2-[3,4-bis(methoxymethoxy)phenyl]ethoxy]carbonyl-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[4-(3-hydroxyphenyl)butoxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[3-(3-hydroxyphenyl)propoxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(2-indol-3-ylethoxy)carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[3-(2-hydroxyphenyl)propoxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 3-[2-[4-(N-t-butoxycarbonylaminomethyl)phenyl]ethoxy]carbonyl-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[2-(3-thienyl)ethoxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[2-(2-thienyl)ethoxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[3-(3-hydroxyphenyl)prop-2-ynyloxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[3-(3-methoxyphenyl)prop-2-enyloxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[2-(phenylthio)ethoxy]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[2-(phenyl)ethylthio]carbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(2-indol-3-ylethoxy)carbonyl-5-iodo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(3-methyl-1,2,4-oxadiazol-5-yl)1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-[2-(ethoxycarbonyl)ethenyl]-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline-3-hydroxamic acid;
- 7-chloro-2,4-dioxo-5-iodo-1,2,3,4-tetrahydroquinoline-3-hydroxamic acid;
- 7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acid hydrazide;
- 7-chloro-2,4-dioxo-3-(3-thienyl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(2-thienyl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(2-pyridyl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(3-pyridyl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(4-pyridyl)-1,2,3,4-tetrahydroquinoline;
- 3-(2-benzofuryl)-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 3-(3-benzofuryl)-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(3-methyl-2-furyl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(2-methyl-3-furyl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(4-isopropyl-2-furyl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(4-methyl-2-furyl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(5-phenyl-2-furyl)-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-(5-methyl-2-thienyl)-1,2,3,4-tetrahydroquinoline;
- 3-(5-benzyl-2-thienyl)-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- 3-(3-benzo[b]thienyl)-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline;
- and pharmaceutically acceptable salts thereof.
- 5. A compound selected from:
- 2,4-dioxo-3-ethoxycarbonyl-6-nitro-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-methoxycarbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-n-propoxycarbonyl-1,2,3,4-tetrahydroquinoline;
- 6,7-dinitro-2,4-dioxo-3-ethoxycarbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-ethoxycarbonyl-1,2,3,4-tetrahydroquinoline;
- 2,4-dioxo-3-ethoxycarbonyl-7-nitro-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-n-pentyloxycarbonyl-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-3-ethoxycarbonyl-5-iodo-1,2,3,4-tetrahydroquinoline;
- 7-chloro-2,4-dioxo-5-ethyl-3-methoxycarbonyl-1,2,3,4-tetrahydroquinoline;
- 3-carboxy-7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinoline; and pharmaceutically acceptable salts.
- 6. A pharmaceutical composition comprising an effective amount of at least one compound according to claim 4 or a pharmaceutically acceptable salt thereof in association with one or more pharmaceutically acceptable carriers and/or excipients.
- 7. A pharmaceutical composition comprising an effective amount of at least one compound according to claim 5 or a pharmaceutically acceptable salt thereof in association with one or more pharmaceutically acceptable carriers and/or excipients.
- 8. A pharmaceutical composition comprising an effective amount of at least one compound according to claim 1 or a pharmaceutically acceptable salt thereof in association with one or more pharmaceutically acceptable carriers and/or excipients.
- 9. A pharmaceutical composition comprising an effective amount of at least one compound according to claim 2 or a pharmaceutically acceptable salt thereof in association with one or more pharmaceutically acceptable carriers and/or excipients.
- 10. A pharmaceutical comprising an effective amount of at least one compound according to claim 3 or a pharmaceutically acceptable salt thereof in association with one or more pharmaceutically acceptable carriers and/or excipients.
Priority Claims (2)
Number |
Date |
Country |
Kind |
9012165 |
May 1990 |
GBX |
|
9108356 |
Apr 1991 |
GBX |
|
Parent Case Info
This is a continuation of application Ser. No. 705,976, filed May 28, 1991, now abandoned.
US Referenced Citations (4)
Foreign Referenced Citations (4)
Number |
Date |
Country |
0386839 |
Feb 1990 |
EPX |
0016878 |
Jan 1984 |
JPX |
0152966 |
Jun 1990 |
JPX |
90-15052 |
Dec 1990 |
WOX |
Continuations (1)
|
Number |
Date |
Country |
Parent |
705976 |
May 1991 |
|