Claims
- 1. A quinoline derivative of the formula (I): ##STR25## wherein R is a hydrogen atom, or an alkyl group or a phenyl alkyl group having 7 to 9 carbon atoms in which the benzene ring is substituted or unsubstituted; m is 0 or 1; and when m=1, each of rings A, B and C is substituted or unsubstituted; and when m=0, (a) each of rings A and C is substituted or unsubstituted and ring B is substituted, or (b) ring C is substituted with at least one fluorine atom, ring B has no substituent and ring A is substituted or unsubstituted, the substituents for the A, B and C rings numbering from 1 to 4 and being selected from the group consisting of a halogen atom, an optionally halogenated lower alkyl group, an optionally halogenated lower alkoxy group, an optionally halogenated lower alkylthio group, nitro group, a carboxyl group, an esterified carboxyl group, hydroxy group, a C1-4 acyloxy group selected from the group consisting of formyloxy, acetyloxy, propionyloxy, and butyryloxy, and an aliphatic acyl group having 1-3 carbon atoms selected from the group consisting of formyl, acetyl, and propionyl;
- subject to at least one of the following provisos:
- (a) the ring A has a substituent at the 6-, 8-, or both positions of the quinoline nucleus,
- (b) the ring B has a substituent at the 2-position, or
- (c) the ring C has a substituent at the 2-, 4-, or both positions;
- or its salt.
- 2. A quinoline derivative of claim 1 wherein R is hydrogen, an alkyl group having 1-8 carbon atoms, or a phenylalkyl group having 7-9 carbon atoms.
- 3. A quinoline derivative of claim 1, in which each of the rings A, B and C has one to four substituents selected from the group consisting of a halogen atom, an optionally halogenated lower alkyl group, an optionally halogenated lower alkoxy group, an optionally halogenated lower alkylthio group, nitro group, a carboxyl group, an esterified carboxyl group, hydroxy group, a C.sub.1-4 acyloxy group and an aliphatic acyl group having 1-3 carbon atoms.
- 4. A quinoline derivative of the formula (I.sup.a): ##STR26## wherein R.sup.2 and R.sup.3 are, the same or different, a halogen atom or an alkyl group having 1-4 carbon atoms.
- 5. A quinoline derivative of the formula (I.sup.b): ##STR27## wherein R.sup.4 and R.sup.5 are, the same or different, an alkyl group having 1-4 carbon atoms, and R.sup.3 is a halogen atom or an alkyl group having 1-4 carbon atoms.
- 6. A quinoline derivative which is
- 6-chloro-4-(2-chlorophenyl)-3-[3-(2,4-difluorophenyl) ureido]quinoline,
- 6-chloro-3-[3-(2,4-difluorophenyl)ureido]-4-(2-methylphenyl)quinoline,
- 3-[3-(2,4-difluorophenyl)ureido]-6-methyl-4-(2-methylphenyl)quinoline,
- 4-(2-chlorophenyl)-3-[3-(2,4-difluorophenyl)ureido]-6,8-dimethylquinoline,
- 4-(2-chlorophenyl)-3-[3-(2,4-difluorophenyl)ureido]-6-ethylquinoline,
- 4-(2-chlorophenyl)-3-[3-(2,4-difluorophenyl)ureido]-6-fluoroquinoline,
- 3-[3-(2,4-difluorophenyl)ureido]-6-methyl-4-(2-methylphenyl)quinoline,
- 4-(2-chlorophenyl)-3-[3-(2,6-dimethylphenyl)ureido]-6,8-dimethylquinoline or 4-(2-chlorophenyl)-3-[3-(4-hydroxy-3,5-dimethylphenyl)ureido]-6,8-dimethylquinoline.
- 7. A composition for the inhibition of acyl-CoA: cholesterol-acyl-transferase which comprises a quinoline derivative of the formula (I) as claimed in claim 1 and a pharmaceutically acceptable diluent or carrier.
- 8. A method of inhibiting acyl-CoA: cholesterol-acyl-transferase which comprises administering to a patient in need thereof an effective amount of a quinoline derivative of the formula (I): ##STR28## wherein R is a hydrogen atom, or an alkyl group or a phenyl alkyl group having 7 to 9 carbon atoms in which the benzene ring is substituted or unsubstituted, m is 0 or 1; and when m=1, each of rings A, B and C is substituted or unsubstituted; and when m=0, (a) each of rings A and C is substituted or unsubstituted and ring B is substituted, or (b) ring C is substituted with at least one fluorine atom, ring B has no substituent and ring A is substituted or unsubstituted, the substituents for the A, B and C rings numbering from 1 to 4 and being selected from the group consisting of a halogen atom, an optionally halogenated lower alkyl group, an optionally halogenated lower alkoxy group, an optionally halogenated lower alkylthio group, nitro group, a carboxyl group, an esterified carboxyl group, hydroxy group, A C1-4 acyloxy group selected from the group consisting of formyloxy, acetyloxy, propionyloxy, and butyryloxy and an aliphatic acyl group having 1-3 carbon atoms selected from the group consisting of formyl, acetyl, and propionyl or a pharmaceutically acceptable salt thereof.
- 9. 4-(2-chlorophenyl)-3-[3-(2,4-difluorophenyl)ureido-6,7-dimethylquinoline.
Priority Claims (3)
Number |
Date |
Country |
Kind |
63-174137 |
Jul 1988 |
JPX |
|
63-214266 |
Aug 1988 |
JPX |
|
1-75925 |
Jul 1989 |
JPX |
|
Parent Case Info
This application is a continuation of U.S. application Ser. No. 07/377,136 filed Jul. 10, 1989 now abandoned.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
3798226 |
Meguro et al. |
Mar 1974 |
|
3819634 |
Megoro et al. |
Jun 1974 |
|
3862152 |
Kuwada et al. |
Jan 1975 |
|
Non-Patent Literature Citations (1)
Entry |
Grant and Hackh's Chemical Dictionary (1987, McGraw-Hill, New York), p. 14. |
Continuations (1)
|
Number |
Date |
Country |
Parent |
377136 |
Jul 1989 |
|