6-substituted 1,2,4a,5a,8a,8b-hexahydro- and 1,2,3,4,4a,5a,8a,8b-octahydro-6H-pyrrolo[3′,4′:4,5]furo[3,2-b]pyrid-8(7H)-one derivatives and their use in combatting endoparasites
AssigneeBayer Aktiengesellschaft
InventorsPeter Jeschke, Achim Harder, Norbert Mencke, Georg von Samson-Himmelstjerna
Life of this patent
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Abstract
The present invention relates to 6-substituted 1,2,4a,5a,8a,8b-hexahydro- and 1,2,3,4,4a,5a,8a,8b-octahydro-6H-pyrrolo[3′,4′:4,5]furo[3,2-b]pyrid-8(7H)-one derivatives of the general formula (I) and their salts in which the radicals R1, R2, R3, R4, B and A are each as defined in the description, to processes for their preparation and to their use for controlling endoparasites.
Claims8
6-Substituted 1,2,4a,5a,8a,8b-hexahydro- and 1,2,3,4,4a,5a,8a,8b-octahydro-6H-pyrrolo[3′,4′:4,5]furo[3,2-b]pyrid-8(7H)-one compound of the formula (I) or a pharmaceutically acceptable salt thereof
- in which
- R1 represents hydrogen, straight-chain or branched alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl, or hetarylalkyl, which is optionally substituted,
- R2 represents hydrogen, straight-chain or branched alkyl, cycloalkyl, or alkoxycarbonyl, which Is optionally substituted,
- R1 and R2 together with the atoms to which they are attached represent a 5- or 6-membered ring which Is optionally interrupted by oxygen, sulphur, sulphoxyl or sulphonyl and which is optionally substituted,
- R3 represents hydrogen, straight-chain or branched alkyl, cycloalkyl or alkoxycarbonyl, which is optionally substituted,
- R4 represents hydrogen, straight-chain or branched alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, hetaryl, hetarylalkyl, amino, alkylamino, dialkylamino, or cycloalkylamino, which is optionally substituted,
- A represents hydroxyl, alkoxy, alkenyloxy, alkinyloxy, arylalkyloxy, formyloxy, azido, halogen, aryloxy, hetarylalkyloxy, hetaryloxy, mercapto, alkylthio, alkylsulphonyl, alkenylthio, alkenylsulphonyl, alkinylthio, alkinylsulphonyl, arylalkylthio, arylalkylsulphonyl, hetarylalkylthio, hetarylalkylsulphonyl, arylthio, arylsulphonyl, alkyl, alkenyl, alkinyl, aryl, arylalkyl, hetaryl, hetarylalkyl, or alkoxycarbonyl, which is optionally substituted, or cyano, carbamoyl, thiocarbamoyl, or optionally represents a radical from the group consisting of A1, A2 and A3
- in which
- X represents oxygen or sulphur,
- represents carboxyl, thiocarboxyl, sulphoxyl, sulphonyl, —P(O)—O—R5 or —P(S)—O—R5,
- Q represents straight-chain or branched alkyl, alkenyl, alkinyl, cycloalkyl, alkoxy, alkenyloxy, alkinyloxy, aryl, arylalkyl, cycloalkoxy, hetaryl, hetarylalkyl, or a cyclic amino group which is attached via nitrogen and which is optionally substituted,
- R5 represents alkyl,
- R6 represents hydrogen, alkyl, alkoxy, arylalkoxy, alkylthio, cycloalkylthio, arylthio, or hetarylalkylthio,
- R7 represents alkyl, alkenyl, cycloalkyl, alkylthio, arylthio, aryl, arylalkyl, hetaryl or hetarylalkyl, which is optionally substituted,
- R6 and R7 together with the atoms to which they are attached represent a 5-, 6 or 7-membered carbocyclic ring, which is optionally substituted,
- B represents hydrogen, straight-chain or branched alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, hetaryl, or hetarylalkyl, which is optionally substituted, formyl, alkoxydicarbonyl or optionally represents a radical from the group consisting of B1, B2, B3 and B4
- in which
- R8 represents hydrogen, straight-chain or branched alkyl, cycloalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, which is optionally substituted,
- R8 and R9 together with the atoms to which they are attached represent a 5- or 6-membered ring which is optionally interrupted by oxygen, sulphur, sulphoxyl or sulphonyl and is optionally substituted,
- R9 and R10 independently of one another each represent hydrogen, straight-chain or branched alkyl, alkenyl, cycloalkyl, optionally substituted aryl, arylalkyl, hetaryl, or hetarylalkyl, or
- R9 and R10 together represent a spirocyclic ring, which is optionally substituted,
- represents carboxyl, thiocarboxyl, —C═CH—NO2, —C═CH—CN, —C═N—R11, sulphoxyl, sulphonyl, —P(O)—O—R5 or —P(S—O—R5,
- R11 represents hydrogen, hydroxyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, halogenoalkylcarbonyl, alkylsulphonyl, nitro or cyano, and
- Q1 represents straight-chain or branched alkyl, alkenyl, alkinyl, cycloalkyl, aryl, arylalkyl, hetaryl or hetarylalkyl, which is optionally substituted, or a radical from the group consisting of G1 and G2
- in which
- may represent carboxyl, thiocarboxyl or sulphonyl,
- Z represents oxygen, sulphur or —NR13,
- R12 represents a cyclic amino group which is attached via a nitrogen atom, if Z is nitrogen,
- R12 and R13 independently of one another represent hydrogen, straight-chain or branched alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkyl-alkyl, alkoxycarbonyl, aryl, arylalkyl, hetaryl, or hetarylalkyl, which is optionally substituted, or
- R12 and R13 together with the adjacent N atom represent a heterocyclic 5-, 6- or 7-membered ring system or a 7- to 10-membered bicyclic ring system, which is optionally interrupted by oxygen, sulphur, sulphoxyl, sulphonyl, carbonyl, —N—O, —N═, —NR15— or by quarternized nitrogen and which is optionally substituted,
- R14 represents hydrogen or alkyl,
- R15 represents hydrogen, straight-chain or branched alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, alkoxycarbonyl, alkylcarbonyl, cycloalkylcarbonyl, cyano, aryl, arylalkyl, hetaryl, or hetarylalkyl, which is optionally substituted.
Dependencies are inferred from the claim text.