US5118680A
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US
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Combating endoparasites with 3-hydroxybenzothiophenes
Assignee: Bayer AG
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Filing: 1991-06-20
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Granted: 1992-06-02
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Expires: 2011-06-20
Abstract
Abstract 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 ═CH-- or ═N--, Y represents ═O or ═NH, R 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 2 , NH 2 , alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy and arylthio, which, in turn, may again be substituted, R 2 represents optionally substituted alkoxy, cycloalkoxy or the radical --NR 3 R 4 , R 3 represents hydrogen or alkyl, R 4 represents an alkyl or carbocyclic or heterocyclic armoatic radical or the radical --COOR 5 , R 3 and R 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 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -halogenoalkyl or C 1 -C 4 -alkoxyalkyl R 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.
Inventors
- 👤 Nikolaus Muller
- 👤 Werner Hallenbach
- 👤 Achim Harder
- 👤 Werner Lindner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:24
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/38; C; C07; C07D; C07D495/00; C07D495/02; C07D495/04; A61P; A61P33/00; A61P33/10; C07C; C07C323/00; C07C323/50; C07C323/62; C07D333/00; C07D333/50; C07D333/52; C07D333/62; C07D333/68; C07D333/70
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
183 words
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 ##STR94## in which Y represents ═O or ═NH, R 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 2 , NH 2 , alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy and arylthio, which, in turn, may again be substituted, R 3 represents hydrogen or alkyl, R 4 represents an alkyl or aralkyl carbocylic or heterocyclic aromatic radical or the radical --COOR 5 , R 3 and R 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 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -halogenoalkyl or C 1 -C 4 -alkoxyalkyl, or optionally substituted aryl, R 5 represents alkyl, cycloalkyl, aralkyl or aryl, which, in turn, may again be substituted.
Claim 2
Independent Claim
183 words
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 ##STR94## in which Y represents ═O or ═NH, R 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 2 , NH 2 , alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy and arylthio, which, in turn, may again be substituted, R 3 represents hydrogen or alkyl, R 4 represents an alkyl or aralkyl carbocylic or heterocyclic aromatic radical or the radical --COOR 5 , R 3 and R 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 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -halogenoalkyl or C 1 -C 4 -alkoxyalkyl, or optionally substituted aryl, R 5 represents alkyl, cycloalkyl, aralkyl or aryl, which, in turn, may again be substituted.
Claim 3
Dependent Claim
289 words
The method according to claim 1, in which R 1 represents alkyl having 1 to 4 carbon atoms; alkoxy having 1 to 4 carbon atoms; alkylthio having 1 to 4 carbon atoms; halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms, where the halogen atoms are identical or different; halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms; halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms; in the case of phenyl, represents alkylenedioxy having 1 or 2 carbon atoms; in the case of phenyl represents halogen-substituted alkylenedioxy having 1 or 2 carbon atoms and.1 to 4 halogen atoms; halogen; cyano; nitro; dialkylamino having 1 to 4 carbon atoms per alkyl group; alkylcarbonyl having 2-4 carbon atoms; carbalkoxy having 2 to 4 carbon atoms; alkylsulphonyl having 1 to 4 carbon atoms; arylsulphonyl having 6 or 10 aryl carbon atoms; phenyl, naphthyl, phenoxy, naphthoxy, phenylthio or naphthylthio, which in turn, may again be substituted, R 3 represents hydrogen or alkyl, R 4 represents C 1-4 -alkyl, benzyl or phenyl which are optionally substituted by one of the radicals mentioned for R 1 , or represents a radical of the formula --COOR 5 , or R 3 and R 4 , together with the adjacent nitrogen atom, represent a 5- or 6-membered heterocycle which may contain O, or N as further hetero atoms and is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxyalkyl or optionally substituted aryl, R 5 represent C 1 -C 4 -cycloalkyl, aralkyl or aryl which, in turn, may be substituted by one of the radicals mentioned under R 1 , Y represents ═O or ═NH.
Claim 4
Dependent Claim
176 words
The method according to claim 1, in which R 1 represents halogen, C 1 -C 4 -alkyl, C 1-4 -alkoxy, C 1-4 -halogenoalkoxy, C 1-4 -halogenoalkylthio, phenyl which is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, C 1 -C 4 -halogenoalkylthio, C 1 -C 4 -alkylthio, halogenosulphonyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -halogenoalkylsulphonyl, C 1 -C 4 -halogenoalkyl, or methylenedioxy or ethylenedioxy which are optionally substituted by fluorine or chlorine, halogen, NO 2 , or phenoxy which is optionally substituted by one of the abovementioned radicals, R 3 represents hydrogen, R 4 represents C 1-4 -alkyl, benzyl or phenyl which are optionally substituted by one of the radicals mentioned for R 1 or represents a radical of the formula --COOR 5 , or R 3 and R 4 , together with the adjacent nitrogen atom, represent one of the radicals piperidino, morpholino, pyrolidino, N-methylpiperazino or 2,6-dimethylmorpholino or 2,6-diphenylmorpholino R 5 represents C 1-4 -alkyl or benzyl, Y represents ═O or ═NH.
Claim 5
Dependent Claim
131 words
The method according to claim 1, in which R 1 represents fluorine or chlorine, NO 2 , CF 3 , CH 3 , OCF 3 , SCF 3 , SCF 2 Cl, OCH 3 , OCF 2 CF 2 H, --CF 2 CHFO--, --O--CH 2 --O or --O--CF 2 --O, R 3 represents hydrogen, R 4 represents methyl, ethyl, benzyl or phenyl which are optionally substituted by halogen, C 1-4 -alkyl, C 1-4 -halogenoalkyl, C 1-4 -alkoxy, C 1-4 -alkylmercapto, C 1-4 -halogenoalkylmercapto, or C 1-4 -alkoxycarbonyl, or represents the radical --COOR 5 , or R 3 and R 4 , together with the adjacent nitrogen atom, represent one of the radicals piperidino, morpholine 2,6-dimethylmorpholino or N-methylpiperazino, R 5 represents C 1-4 -alkyl or benzyl, and Y represents ═O or ═NH.
Claim 6
Dependent Claim
143 words
A method according to claim 1 ##STR95## in which Y represents ═O or ═NH, R 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 2 , NH 2 , alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy and arylthio, which, in turn, may again be substituted, R 3 represents hydrogen or alkyl, and R 4 represents an alkyl, aralkyl, carbocyclic or heterocyclic aromatic radical, or R 3 and R 4 , together with the adjacent nitrogen atom, represent a 5- or 6-membered heterocycle which may contain O or N as further hetero atoms and is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -halogenoalkyl or C 1 -C 4 -alkoxyalkyl or optionally substituted aryl.
References Cited (Backward Citations)
US3971814A
Cited
US4800211A
Cited
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