N-heteroaryl-N'-phenylurea derivatives, their production and use

Abstract

An N-heteroaryl-N'-phenylurea derivative represented by the general formula (I): wherein R1, R2, R3, R4, R5, R6 and R7 are as defined in the description of the specification which is useful as a prophylactic and therapeutic agent for hypercholesterolemia, atherosclerosis and diseases caused by them.

What is claimed is: .[.1. An N-heteroaryl-N'-phenylurea derivative represented by the general formula (I): ##STR19## wherein R 1  and R 2 , which may be the same or different, are hydrogen atoms; halogen atoms; unsubstituted C 1  -C 10  alkyl groups; substituted C 1  -C 6  alkyl groups having a C 2  -C 8  -dialkylamino group as the substituent; substituted C 1  -C 6  alkyl groups having as the substituent a saturated cyclic amino group which may have a heteroatom in the ring; C 1  -C 6  alkoxy groups; or nitro groups, R 1  and R 2  being able to be taken together to represent a C 3  -C 6  alkylene group, R 3  and R 4 , which may be the same or different, are hydrogen atoms, halogen atoms, C 1  -C 6  alkyl groups, C 1  -C 6  haloalkyl groups, C 1  -C 6  alkoxy groups or C 1  -C 6  alkylthio groups, R 5 , R 6  and R 7 , which may be the same or different, are hydrogen atoms, halogen atoms, C 1  -C 8  alkyl groups, C 1  -C 6  haloalkyl groups, C 3  -C 7  alkenyl groups, C 1  -C 6  alkoxy groups, C 1  -C 6  alkylthio groups or C 2  -C 8  -dialkylamino groups, and X is --S-- or a pharmacologically acceptable salt thereof..]..[.2. An N-heteroaryl-N'-phenylurea derivatives according to claim 1, wherein R 1  is a halogen atom or a C 1  -C 10  alkyl group, R 2  is a hydrogen atom or a C 1  -C 6  alkyl group, R 1  and R 2  being able to be taken together to represent a C 3  -C 6  alkylene group, R 3  is a halogen atom, a C 1  -C 4  alkyl group, a C 1  -C 4  alkylthio group or trifluoromethyl group, R 4  is a hydrogen atom or a halogen atom, R 5  and R 6  which may be the same or different, are halogen atoms or C 1  -C 4  alkyl groups, and R7 is a hydrogen atom or a halogen atom..]..[.3. An N-heteroaryl-N'-phenylurea derivative according to claim 1, wherein R 1  is a chlorine atom or a C 1  -C 8  alkyl group, R 2  is a halogen atom or a C 1  -C 3  alkyl group, R 1  and R 2  being able to be taken together to represent a C 3  -C 4  alkylene group, R 3  is a halogen atom, a C 1  -C 4  alkyl group or a C 1  -C 4  alkylthio group, R 4  is a hydrogen atom, R 5  and R 6  which may be the same, are halogen atoms or C 1  -C 4  alkyl groups, and R 7  is a hydrogen atom..]..[.4. A pharmaceutical composition for inhibiting acyl-CoA:cholesterol O-acryltransferase comprising as active ingredient a compound represented by the general formula (I): ##STR20## wherein R 1  and R 2 , which may be the same or different, are hydrogen atoms; halogen atoms; unsubstituted C 1  -C 10  alkyl groups; substituted C 1  -C 6  alkyl groups having a C 2  -C 8  -dialkylamino group as the substituent; substituted C 1  -C 6  alkyl groups having as the substituent a saturated cyclic amino group which may have a heteroatom in the ring; C 1  -C 6  alkoxy groups; or nitro groups, R 1  and R 2  being able to be taken together to represent a C 3  -C 6  alkylene group, R 3  and R 4 , which may be the same or different, are hydrogen atoms, halogen atoms, C 1  -C 6  alkyl groups, C 1  -C 6  haloalkyl groups, C 1  -C 6  alkoxy groups or C 1  -C 6  alkylthio groups, R 5 , R 6  and R 7 , which may be the same or different, are hydrogen atoms, halogen atoms, C 1  -C 8  alkyl groups, C 1  -C 6  haloalkyl groups, C 3  -C 7  alkenyl groups, C 1  -C 6  alkoxy groups, C 1  -C 6  alkylthio groups or C 2  -C 8  -dialkylamino groups, and X is --S-- or a pharmacologically acceptable salt thereof, and a pharmacologically acceptable carrier..]..[.5. A pharmaceutical composition for inhibiting acyl-CoA:chlesterol O-acyltransferase according to claim 4, wherein R 1  is a halogen atom or a C 1  -C 10  alkyl group, R 2  is a hydrogen atom or a C 1  -C 6  alkyl group, R 1  and R 2  being able to be taken together to represent a C 3  -C 6  alkylene group, Rhu is a halogen atom, a C 1  -C 4  alkyl group, a C 1  -C 4  alkylthio group or trifluoromethyl group, R 4  is a hydrogen atom or a halogen atom, R 5  and R 6  which may be the same or different, are halogen atoms or C 1  -C 4  alkyl groups, and R 7  is a hydrogen atom or a halogen atom..]..[.6. A pharmaceutical composition for inhibiting acyl-CoA:cholesterol O-acyltransferase according to claim 4, wherein R 1  is a chlorine atom or a C 1  -C 8  alkyl group, R 2  is a hydrogen atom or a C 1  -C 3  alkyl group, R 1  and R 2  being able to be taken together to represent a C 3  -C 4  alkylene group, R 3  is a halogen atom, a C 1  -C 4  alkyl group or a C 1  -C 4  alkylthio group, R 4  is a hydrogen atom, R 5  and R 6  which may be the same, are halogen atoms or C 1  -C 4   
     
        alkyl groups, and R 7  is a hydrogen atom..]..Iadd.7.  A compound consisting of N-(2,6-Diethylphenyl)-N'-(3-(2-methylphenyl)-6,7-dihydro-5H-cyclopenta(f)(1)benzothiophen-2-yl-urea. .Iaddend..Iadd.8. A pharmaceutical composition for inhibiting acyl-CoA:cholesterol O-acryltransferase comprising as active ingredient, a compound, N-heteroaryl-N'-phenylurea derivative consisting of N-(2,6-Diethylphenyl)-N'-(3-(2-methylphenyl)-6,7-dihydro-5H-cyclopenta(f)(1)benzothiophen-2-yl)urea, or a pharmacologically acceptable salt thereof, and a pharmaceutically acceptable carrier. .Iaddend.