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    1.
    发明专利
    未知

    公开(公告)号：DE2131034A1

    公开(公告)日：1973-01-11

    申请号：DE2131034

    申请日：1971-06-23

    Applicant: HOECHST AG

    Inventor： SCHMITT KARL DR ,  HOFFMANN IRMGARD DR

    IPC: C07D295/13 ,  C07D51/70

    Abstract: 1368699 Benzoyl ureas FARBWERK HOECHST AG 23 June 1972 [23 June 1971] 29563/72 Heading C2C Novel compounds (I) and their salts in which R 1 represents one or more substituents selected from hydrogen, halogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-7 cycloalkyl, C 4-7 cycloalkenyl, aralkyl (having 1 to 4 C atoms in the alkyl moiety), phenyl, hydroxyl, acyloxy C 1-6 alkoxy, C 3-6 alkenyloxy, aralkoxy or araloxyalkoxy (having 1 to 4 C atoms in the alkyl moiety), aryloxy, trifluoromethyl and nitro and wherein two adjacent substituents R 1 may form a carbocyclic ring having 5 to 7 ring members or an alkylene-dioxy group, R 2 represents one or more substituents selected from hydrogen, halogen, C 1-4 alkyl and C 1-4 alkoxy and A is a C 2-6 alkylene radical are prepared by (1) reaction of an R 1 substituted benzoyl-isocyanate, -carbamate, -carbamoyl halide, -thiocarbamate, -urea, -semicarbazide, or -semicarbazone with an amine of Formula II (2) an R 1 substituted benzamide is reacted with an isocyanate, carbamate, thiocarbamate, carbamoyl halide or urea each substituted by a group of Formula V (3) a correspondingly substituted benzoylisourea ether or ester, benzoyl-isothiourea ether, benzoyl-parabanic acid or benzoylhaloformic acid amidine is hydrolysed; (4) water is added to a correspondingly substituted benzoylcarbodi-imide; (5) a correspondingly substituted benzoyl-thiourea, thiobenzoyl urea or thiobenzoyl-thiourea is treated with a heavy metal oxide, heavy metal salt or an oxidizing agent to replace the sulphur atom by an oxygen atom; (6) an R 1 substituted benzoic acid or halide ester or anhydride thereof is reacted with a urea substituted by the group of Formula (V); (7) a compound IV is reacted with a piperazine VII (8) a compound VI in which B represents a radical of Formula VIII is reacted with R 2 substituted aniline; (9) a compound VI in which B is an R 2 substituted phenyl group, preferably in the form of its reactive ester is reacted with an amine of Formula IX Preferred compounds are N-(4-methoxy-benzoyl)- N 1 - [3 - (4 - m - tolyl - piperazin - 1 - yl) - propyl]- urea; N - (5 - chloro - 2 - methoxy - benzoyl) - N 1 - [3 - (4 - m - tolyl - piperazin - 1 - yl) - propyl]- urea and its hydrochloride; N-(3,4-methylenedioxy - benzoyl) - N 1 - [3 - (4 - m - tolyl - piperazine- 1-yl)-propyl] urea dihydrochloride; N-(2,5-dimethylbenzoyl) - N 1 - [3 - (4 - m - tolyl - piperazin- 1 - yl) - propyl] urea; N - (1 - naphthoyl) - N 1 - [3 - (4 - m - tolyl - piperazin - 1 - yl) - propyl]- urea; N - (5,6,7,8 - tetrahydro - 1 - naphthoyl)- N 1 - [3 - (4 - m - tolyl - piperazin - 1 - yl) - propyl]- urea. Compounds I are tranquillizers and form with a suitable carrier a pharmaceutical preparation which may be administered orally or parenterally.

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