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    • 3. 发明授权
    • Substituted 1,3,4-oxa (thia) diazolinones process for their preparation
and their use of combating endoparasites
    • US5093343A
    • 1992-03-03
    • US577970
    • 1990-09-05
    • Gerhard BonseNikolaus MullerAchim Harder
    • Gerhard BonseNikolaus MullerAchim Harder
    • A01N43/824A61K31/41A61K31/4245A61K31/433A61P33/10C07D271/10C07D271/113C07D285/12C07D285/125C07D285/13
    • C07D271/113C07D285/125C07D285/13
    • Substituted 1,3,4-oxa- and thiadiazolinones of the formula (I) ##STR1## in which R.sup.1 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, halogenoalkyl, halogenoalkoxy or halogenoalkylthio,R.sup.2 represents one or more identical or different radicals from among hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be sutstituted,R.sup.3 represents one or more identical or different radicals from among hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be substituted,X represents O or S, andY represents O or S,with the exception of the compounds 5-phenoxy-3-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2(3H)-one, and 5-phenoxy-3-(3-chloro-4-fluorophenyl)-1,3,4-oxadiazol-2-(3H)-one are disclosed as useful to combat endoparasites. Compositions containing these compounds and process for preparing them are also disclosed.The present invention relates to new substituted 1,3,4-oxa(thia)diazolinones, process for their preparation, and their use for combating endoparasites.Substituted 2-alkoxy-1,3,4-oxathiazolinones and their use against endoparasites are already known, but their actions are not always satisfactory (DE-OS (German Published Specification) 2,604,110). Previously described compounds are furthermore 2-aryloxy-1,3,4-oxadiazolinones (Pilgram, J. Heterocyclic Chem. 39, 823 (1982)); however, nothing is known about their use for combating endoparasites.The present invention relates to substituted 1,3,4-oxa-and thiadiazolinones of the formula (I) ##STR2## in which R.sup.1 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, halogenoalkyl, halogenoalkoxy or halogeno-alkylthio,R.sup.2 represents one or more identical or different radicals from amongst hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogeno-alkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkyl-sulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be substituted,R.sup.3 represents one or more identical or different radicals from amongst hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogeno-alkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, alkylcarbonyl, carbalkoxy, alkyl-sulphonyl, arylsulphonyl, sulphamoyl, alkyl-sulphamoyl, dialkylsulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be substituted,X represents 0 or S, andY represents 0 or S,with the exception of the compounds 5-phenoxy-3-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2(3H)-one and 5-phenoxy-(3-chloro-4-fluorophenyl)-1,3,4-oxadiazol-2-(3H)-one.The invention also relates to a process for the preparation of the new substituted 1,3,4-oxa- and thiadiazolinones of the formula ##STR3## in which R.sup.1 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, halogenoalkyl, halogenoalkoxy or halogeno-alkylthio,R.sup.2 represents one or more identical or different radicals from amongst hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogeno-alkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, aryl-sulphonyl, sulphamoyl, alkylsulphamoyl, dialkyl-sulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be substituted,R.sup.3 represents one or more identical or different radicals from amongst hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogeno-alkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, alkylcarbonyl, carbalkoxy, alkyl-sulphonyl, arylsulphonyl, sulphamoyl, alkyl-sulphamoyl, dialkylsulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be substituted,X represents O or S, andY represents O or S,with the exception of the compounds 5-phenoxy-3-(3,4-dichlorophenyl)-1,3,4-oxadiazol-2(3H)-one and 5-phenoxy-3-(3-chloro-4-fluorophenyl)-1,3,4-oxadiazol-2-(3H)-one, characterized in that compounds of the formula (II) ##STR4## in which X, Y, R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meaning, are reacted with carbonylation reagents such as phosgene, phosgene or triphosgene, and the compounds obtained in this process, of the formula III ##STR5## in which X, Y, R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meaning, are cyclized in the presence of bases.
    • 4. 发明授权
    • Combating endoparasites with 3-hydroxybenzothiophenes
    • 与3-羟基苯并噻吩组合内给药
    • US5118680A
    • 1992-06-02
    • US721901
    • 1991-06-20
    • Nikolaus MullerWerner HallenbachAchim HarderWerner Lindner
    • Nikolaus MullerWerner HallenbachAchim HarderWerner Lindner
    • C07D333/64A61K31/38A61K31/381A61K31/435A61P33/00A61P33/10C07C323/62C07C323/65C07C323/67C07D333/70C07D409/06C07D413/06C07D495/04
    • C07D495/04C07C323/62C07D333/70
    • A method of combating endoparasites in humans and animals which comprises administering to such humans and animals an endoparasiticidally effective amount of a 3-hydroxybenzothiophene of the formula ##STR1## in which X represents .dbd.CH-- or .dbd.N--,Y represents .dbd.O or .dbd.NH,R.sup.1 represents one or more identical or different radicals from the group consisting of hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy and arylthio, which, in turn, may again be substituted,R.sup.2 represents optionally substituted alkoxy, cycloalkoxy or the radical --NR.sup.3 R.sup.4,R.sup.3 represents hydrogen or alkyl,R.sup.4 represents an alkyl or carbocyclic or heterocyclic armoatic radical or the radical --COOR.sup.5,R.sup.3 and R.sup.4, together with the adjacent nitrogen atom, represent a 5- or 6-membered heterocycle which may contain O or N as further heteroatoms and is optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -hydroxyalkyl, C.sub.1 -C.sub.4 -halogenoalkyl or C.sub.1 -C.sub.4 -alkoxyalkylR.sup.5 represents alkyl, cycloalkyl, aralkyl or aryl, which, in turn, may again be substituted or optionally substituted aryl.Many of the compounds are new, as well as their own intermediates.
    • 一种对抗人和动物内寄生虫的方法,其包括向所述人和动物施用内寄生有效量的式(I)的3-羟基苯并噻吩,其中X表示= CH-或= N-,Y表示= O或= NH,R 1表示与氢,烷基,烷氧基,烷硫基,卤代烷基,卤代烷氧基,卤代烷硫基,亚烷基二氧基,卤代亚烷基二氧基,卤素,CN,NO 2,NH 2,烷基氨基,二烷基氨基,烷基羰基中的一个或多个相同或不同的基团 ,烷基磺酰基,芳基磺酰基,氨磺酰基,烷基氨磺酰基,二烷基氨磺酰基,芳基,芳氧基和芳硫基,其又可以被取代,R 2表示任选取代的烷氧基,环烷氧基或基-NR 3 R 4,R 3表示氢或烷基,R 4表示 烷基或碳环或杂环杂环基团或基团-COOR 5,R 3和R 4与相邻的氮原子一起代表5-或6-元杂环 可以含有O或N作为其它杂原子并且任选被C 1 -C 4 - 烷基,C 1 -C 4 - 羟基烷基,C 1 -C 4 - 卤代烷基或C 1 -C 4 - 烷氧基烷基取代的O 2可以表示烷基,环烷基,芳烷基或芳基, 又可以是取代的或任选取代的芳基。 许多化合物是新的,以及它们自己的中间体。
    • 5. 发明授权
    • Substituted 1,3,4-thiadizaolinones, processes for their preparation, and
their use for combating endoparasites
    • 取代1,3,4-噻唑烷酮,其制备方法及其用于组合内生菌的用途
    • US5095024A
    • 1992-03-10
    • US581934
    • 1990-09-13
    • Nikolaus MullerGerhard BonseWerner LindnerAchim Harder
    • Nikolaus MullerGerhard BonseWerner LindnerAchim Harder
    • A01N43/824A61K31/41A61K31/433A61P33/00A61P33/10C07C243/28C07C337/02C07C337/06C07D285/12C07D285/125C07D285/13
    • C07D285/13C07C337/02C07D285/125
    • Substituted 1,3,4-thiadiazolinones of the formula (I), ##STR1## in which X represents O or S,R.sup.1 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, halogenoalkyl, halogenoalkoxy or halogenoalkylthio,R.sup.2 represents one or more identical or different radicals from the series comprising hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy and arylthio, each of which can, in turn, be substituted as well, andR.sup.3 represents alkyl, alkenyl or alkynyl, each of which can optionally be substituted,with the exception of the compound 5-methylmercapto-3-phenyl-1,3,4-thiadiazol-2-(3H)-one, are disclosed as being useful to combat endoparasites. Compositions containing these compounds, process for preparing them, and novel intermediates are also disclosed.
    • 取代的式(I)的1,3,4-噻二唑啉酮,其中X代表O或S,R1代表氢,烷基,烷氧基,烷硫基,卤素,卤代烷基,卤代烷氧基或卤代烷硫基,R2代表一 或更多相同或不同的基团,其包含氢,烷基,烷氧基,烷硫基,卤代烷基,卤代烷氧基,卤代烷硫基,亚烷基二氧基,卤代亚烷基二氧基,卤素,CN,NO 2,NH 2,烷基氨基,二烷基氨基,烷基羰基,烷氧基,烷基磺酰基,芳基磺酰基,氨磺酰基, 烷基氨磺酰基,二烷基氨磺酰基,芳基,芳氧基和芳硫基,其中每一个也可以被取代,并且R 3表示烷基,烯基或炔基,其中每一个可任选被取代,除了化合物5-甲基巯基 - 3-苯基-1,3,4-噻二唑-2-(3H) - 酮被公开用于对抗内寄生虫。 还公开了含有这些化合物的组合物,其制备方法和新型中间体。
    • 9. 发明授权
    • 3-carbamoyl-4-hydroxy-coumarins for combating parasitic heiminths
    • 3-氨基甲酰基-4-羟基香豆素,用于防治寄生性重锤
    • US4766144A
    • 1988-08-23
    • US35543
    • 1987-04-03
    • Nikolaus MullerEckart KranzPeter Andrews
    • Nikolaus MullerEckart KranzPeter Andrews
    • A61K31/37A61K31/443A61K31/445A61P33/00C07D311/56C07D405/12C07D311/12
    • C07D405/12C07D311/56
    • 3-carbamoyl-4-hydroxy-couramins for combating parasitic helminths of the formula ##STR1## in which R.sup.1 represents hydrogen, halogen, alkyl, NO.sub.2, CN or alkoxy,X represents O, S, SO or SO.sub.2R.sup.2 represents alkyl, halogenoalkyl, phenyl, naphthyl or pyridyl, which can optionally be substituted; or the radical -X-R.sup.2, together with the radical R.sup.3 can also form an alkylenedioxy (-O-alk-O), halogenoalkylenedioxy, oxyalkyleneoxyalkylene (-O-Alk-O-Alk-) or oxyhalogenoalkylene-oxyhalogenoalkylene bridge; andR.sup.3 and R.sup.4 independently of one another represent hydrogen, halogen, CN, OH, NO.sub.2, amino, mono- or dialklylamino, alkyl, halogenoalkyl, aralkyl or aryl, which can optionally be substituted,can be used for combating parasitic helminths.
    • 3-氨基甲酰基-4-羟基维生素,用于对抗式为“IMAGE”的寄生蠕虫,其中R 1表示氢,卤素,烷基,NO 2,CN或烷氧基,X表示O,S,SO或SO 2 R 2表示烷基,卤代烷基, 苯基,萘基或吡啶基,其可任选被取代; 或基团-X-R2与基团R3一起也可以形成亚烷基二氧基(-O-烷基-O),卤代亚烷基二氧基,氧亚烷基氧化烯(-O-Alk-O-Alk-)或氧卤代亚烷基 - 氧卤代亚烷基桥; 并且R 3和R 4彼此独立地表示氢,卤素,CN,OH,NO 2,氨基,单或二烷基氨基,烷基,卤代烷基,芳烷基或芳基,其可任选被取代,可用于对抗寄生蠕虫。