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US 2005/0090486 A1Published application
Trisubstituted pyrimidines
AssigneeBoehringer Ingelheim Pharma GmbH & Co. KG
InventorsKlaus Bornemann, Hans Briem, Cornelia Dorner-Ciossek, Katja Fechteler, Klaus Fuchs, Frank Himmelsbach, Klaus Klinder, Markus Kostka
Life of this patent
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Abstract
The present invention relates to trisubstituted pyrimidines of formula wherein Ra to Re are defined as in claim 1, which are suitable for the treatment of illnesses in which β-amyloid modulators have a therapeutic benefit, the use thereof for preparing a pharmaceutical composition with the abovementioned properties, and processes for the preparation thereof.
Claims12
A trisubstituted pyrimidine of formula (I)
- wherein
- Ra denotes a hydrogen atom or an alkyl group,
- Rb denotes a phenyl group substituted by the groups R1 to R5, while
- R1 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom,
- a C1-6-alkyl, hydroxy or C1-6-alkoxy group,
- a C3-7-cycloalkyl, C4-7-cycloalkoxy or (C3-7-cycloalkyl)alkyl group, which may be substituted in the cycloalkyl moiety by one or two alkyl groups in each case,
- a C2-5-alkenyl, C3-5-alkenyloxy, C2-5-alkynyl or C3-5-alkynyloxy group,
- wherein the vinyl and ethynyl moieties cannot be linked with an oxygen atom, an aryl, aryloxy, arylalkyl, arylalkoxy, alkylsulphenyl, alkylsulphinyl, alkylsulphonyl, alkylsulphonyloxy, arylsulphenyl, arylsulphinyl, arylsulphonyl, arylalkylsulphenyl, arylalkylsulphinyl or arylalkylsulphonyl group, a methyl, methoxy, methylsulphenyl, methylsulphinyl or methylsulphonyl group substituted by 1 to 3 fluorine atoms,
- an ethyl, ethoxy, ethylsulphenyl, ethylsulphinyl or ethylsulphonyl group substituted by 1 to 5 fluorine atoms,
- a nitro, amino, alkylamino, dialkylamino or azido group,
- an 4- to 7-membered alkyleneimino group optionally substituted by one or two alkyl groups,
- an 6 or 7-membered alkyleneimino group optionally substituted by one or two alkyl groups, wherein a methylene group in the 4 position to the imino-nitrogen atom is replaced by the group W, where
- W denotes an oxygen or sulphur atom, a sulphinyl, sulphonyl, imino, N-alkyl-imino, N-formyl-imino, N-alkylcarbonyl-imino, N-cyano-imino, N-alkoxycarbonyl-imino or N-alkylsulphonyl-imino group,
- a formylamino, N-alkyl-formylamino, alkylcarbonylamino, N-alkyl-alkylcarbonylamino, alkylsulphonylamino or N-alkyl-alkylsulphonylamino group,
- an alkylcarbonyl, carboxy, alkoxycarbonyl, aminocarbonyl,
- alkylaminocarbonyl, dialkylaminocarbonyl or cyano group,
- an aminosulphonyl, alkylaminosulphonyl or dialkylaminosulphonyl group,
- an alkyl or alkoxy group substituted by R9, wherein
- R9 denotes a hydroxy, alkoxy, amino, alkylamino, dialkylamino, alkylsulphenyl, alkylsulphinyl, alkylsulphonyl, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or cyano group,
- a 4- to 7-membered alkyleneiminocarbonyl group optionally substituted by one or two alkyl groups,
- a 6 or 7-membered alkyleneiminocarbonyl group optionally substituted by one or two alkyl groups, wherein a methylene group in the 4 position of the alkyleneimino moiety is replaced by the group W, where W is as hereinbefore defined,
- a 4- to 7-membered alkyleneimino group optionally substituted by one or two alkyl groups,
- a 5- to 7-membered alkyleneimino group optionally substituted by one or two alkyl groups, wherein a methylene group adjacent to the nitrogen atom is replaced by a carbonyl group,
- a 6- or 7-membered alkyleneimino group optionally substituted by one or two alkyl groups, wherein a methylene group in the 4 position is replaced by the group W, where W is as hereinbefore defined,
- a formylamino, N-alkyl-formylamino, alkylcarbonylamino, N-alkyl-alkylcarbonylamino, alkylsulphonylamino, N-alkyl-alkylsulphonylamino, perfluoralkylsulphonylamino, N-alkyl-perfluoralkylsulphonylamino, alkoxycarbonylamino, N-alkyl-alkoxycarbonylamino, cyanoamino or N-alkyl-cyanoamino group,
- R2 and R3 in each case independently of one another denote hydrogen, fluorine, chlorine, bromine or iodine atoms, alkyl, alkoxy, fluoroalkyl, fluoroalkoxy or cyano groups or
- R2 together with R3, if they are bound to adjacent carbon atoms, also a methylenedioxy group optionally substituted by one or two alkyl groups, an n-C3-6-alkylene group optionally substituted by one or two alkyl groups, wherein a methylene group may be replaced by the group W′, where W′ has the meanings given above for W and additionally denotes a trifluoroacetylimino group, a 1,3-butadiene-1,4-diylene group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by an alkyl, trifluoromethyl, hydroxy, alkoxy, trifluoromethoxy or cyano group, while the abovementioned 1,3-butadiene-1,4-diylene groups may additionally be substituted by a fluorine or chlorine atom, by an alkyl, trifluoromethyl or alkoxy group,
- R4 and R5 in each case independently of one another denote hydrogen, fluorine or chlorine atoms or
- R4 together with Ra, if R4 is in the o-position to the nitrogen atom substituted by Ra, also denote an n-C2-4-alkylene group optionally substituted by one or two alkyl groups,
- Rc denotes a C1-6-alkyl group optionally mono- or polysubstituted by R9, while R9 is as hereinbefore defined,
- a methyl group substituted by a fluoromethyl, chloromethyl, bromomethyl, difluoromethyl or trifluoromethyl group,
- a C3-7-cycloalkyl, (C3-7-cycloalkyl)alkyl or arylalkyl group,
- a C3-5-alkenyl or C3-5-alkynyl group, wherein the vinyl and ethynyl moieties cannot be linked to the nitrogen atom of the RcNRd group,
- Rd denotes a hydrogen atom or an alkyl group, or
- Rc together with Rd and the nitrogen atom attached to them denote a 3- to 7-membered alkyleneimino group or a 6 or 7-membered alkyleneimino group, wherein a methylene group in the 4 position is replaced by the group W, where W is as hereinbefore defined, and
- Re denotes a nitro, amino, alkylamino, dialkylamino or azido group, a 4- to 7-membered alkyleneimino group optionally substituted by one or two alkyl groups, wherein one or two methylene group adjacent to the nitrogen atoms may be replaced by a carbonyl group, while additionally in this alkyleneimino group a CH2 group in the 4 position may be replaced by the group W where W is as hereinbefore defined,
- a formylamino, N-alkyl-formylamino, alkylcarbonylamino, N-alkyl-alkylcarbonylamino, di(alkylcarbonyl)amino, (C3-7-cycloalkyl)carbonylamino, N-alkyl-(C3-7-cycloalkyl)carbonylamino, (C3-7-cycloalkyl)alkylcarbonylamino, N-alkyl-(C3-7-cycloalkyl)alkylcarbonylamino, arylcarbonylamino, N-alkyl-arylcarbonylamino, arylalkylcarbonylamino, N-alkyl-arylalkylcarbonylamino, heteroarylcarbonylamino, N-alkyl-heteroarylcarbonylamino, heteroarylalkylcarbonylamino, N-alkyl-heteroarylalkylcarbonylamino, alkoxycarbonylamino, N-alkyl-alkoxycarbonylamino, arylalkoxycarbonylamino, N-alkyl-arylalkoxycarbonylamino, aryloxycarbonylamino, N-alkyl-aryl-oxycarbonylamino, (C4-7-cycloalkoxy)carbonylamino, N-alkyl-(C4-7-cycloalkoxy)carbonylamino, (C3-7-cycloalkyl)alkoxycarbonylamino, N-alkyl-(C3-7-cycloalkyl)alkoxycarbonylamino, alkylsulphonylamino, N-alkyl-alkylsulphonylamino, di(alkylsulphonyl)amino, C3-7-cycloalkylsulphonylamino, N-alkyl-C3-7-cycloalkylsulphonylamino, (C3-7-cycloalkyl)alkylsulphonylamino, N-alkyl-(C3-7-cycloalkyl)alkylsulphonylamino, arylsulphonylamino, N-alkyl-arylsulphonylamino, arylalkylsulphonylamino, N-alkyl-arylalkylsulphonylamino, heteroarylsulphonylamino, N-alkyl-heteroarylsulphonylamino, heteroarylalkylsulphonylamino, N-alkyl-heteroarylalkylsulphonylamino, cyanoamino or N-alkyl-cyanoamino group, while additionally the alkyl moieties and cycloalkyl moieties in the abovementioned groups may be substituted by the group R9, while R9 is as hereinbefore defined, and the cycloalkyl moieties may additionally be substituted by one or two alkyl groups,
- a (C5-7-cycloalkyl)carbonylamino, N-alkyl-(C5-7-cycloalkyl)carbonylamino, (C5-7-cycloalkyl)alkylcarbonylamino or N-alkyl-(C5-7-cycloalkyl)alkylcarbonylamino group, while the cycloalkyl moieties may in each case be substituted by one or two alkyl groups and additionally a methylene group in the cycloalkyl moieties of the abovementioned groups is replaced by the group W, where W is as hereinbefore defined,
- a C2-5-alkenylcarbonylamino, N-alkyl-C2-5-alkenylcarbonylamino,
- C2-5-alkynylcarbonylamino, N-alkyl-C2-5-alkynylcarbonylamino,
- perfluoroalkylcarbonylamino, N-alkyl-perfluoroalkylcarbonylamino,
- perchloroalkylcarbonylamino, N-alkyl-perchloroalkylcarbonylamino,
- perfluoroalkylsulphonylamino or N-alkyl-perfluoroalkylsulphonylamino group,
- an alkyleneiminocarbonylamino or N-alkyl-alkyleneiminocarbonylamino group
- optionally substituted in the alkyleneimino moiety by one or two alkyl groups, while the alkyleneimino moiety is 4 to 7-membered in each case,
- an alkyleneiminocarbonylamino or N-alkyl-alkyleneiminocarbonylamino group optionally substituted in the alkyleneimino moiety by one or two alkyl groups, while the alkyleneimino moiety is 6 or 7-membered in each case and a methylene group in the 4 position of the alkyleneimino moiety is replaced in each case by the group W,
- where W is as hereinbefore defined,
- an alkyleneiminothiocarbonylamino or N-alkyl-alkyleneiminothiocarbonylamino group optionally substituted in the alkyleneimino moiety by one or two alkyl groups, while the alkyleneimino moiety is 4 to 7-membered in each case, an alkyleneiminothiocarbonylamino or N-alkyl-alkyleneiminothiocarbonylamino group optionally substituted in the alkyleneimino moiety by one or two alkyl groups, while the alkyleneimino moiety in each case is 6 or 7-membered and a methylene group in the 4 position of the alkyleneimino moiety is replaced in each case by the group W, where W is as hereinbefore defined,
- a R7NR8—CO—NR6 or R7NR8—SO2—NR6-group, wherein
- R6 denotes a hydrogen atom or an alkyl group,
- R7 and R8 in each case independently of one another denote hydrogen atoms or alkyl groups optionally substituted by R9, or
- R6 and R7 together denote an n-C2-3-alkylene group and
- R8 denotes a hydrogen atom or an alkyl group optionally substituted by R9, while R9 is as hereinbefore defined,
- an imidazolidine-2,4-dion-1-yl or imidazolidine-2,4-dion-3-yl-group optionally substituted by 1 to 3 alkyl groups, while one of the alkyl groups may be substituted by R9,
- a 1,3-dihydro-imidazol-2-on-1-yl group optionally substituted by 1 to 3 alkyl groups, while one of the alkyl groups may be substituted by R9,
- a 2,4-dihydro-1,2,4-triazol-3-on-2-yl or 2,4-dihydro-1,2,4-triazol-3-on-4-yl-group optionally substituted by 1 or 2 alkyl groups, while one of the alkyl groups may be substituted by R9,
- a (R14NR15)-R13C═N-group wherein
- R13 denotes a hydrogen atom, an alkyl or C3-7-cycloalkyl group,
- R14 and R15 in each case independently of one another denote an alkyl group, or
- R14 and R15 together with the nitrogen atom between them denote a 4- to 7-membered alkyleneimino group optionally substituted by one or two alkyl groups or a 6- or 7-membered alkyleneimino group optionally substituted by one or two alkyl groups, wherein a methylene group in the 4 position is replaced by the group W, where W is as hereinbefore defined, and
- R13 denotes a hydrogen atom, an alkyl or C3-7-cycloalkyl group,
- a (R18N═)CR16-R17N-group wherein
- R16 denotes a hydrogen atom, an alkyl, C3-7-cycloalkyl, trifluoromethyl or trichloromethyl group,
- R17 and R18, which may be identical or different, in each case represent a hydrogen atom or an alkyl group or
- R16 and R18 together represent an n-C3-5-alkylene group optionally substituted by one or two alkyl groups and
- R17 represents a hydrogen atom or an alkyl group or
- R17 and R18 together represent an n-C2-4-alkylene group optionally substituted by one or two alkyl groups and
- R16 denotes a hydrogen atom, an alkyl or C3-7-cycloalkyl group,
- an (R19R20PO)-NH-group optionally substituted at the nitrogen atom by an alkyl group, wherein
- R19 and R20, which may be identical or different, denote alkyl or aryl groups,
- a alkyl or alkoxy group substituted by R9, wherein R9 is as hereinbefore defined,
- a formyl, alkylcarbonyl, 1-(hydroxyimino)alkyl, 1-(alkoxyimino)alkyl, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or cyano group,
- a sulpho, alkoxysulphonyl, aminosulphonyl, alkylaminosulphonyl or dialkylaminosulphonyl group,
- a 4- to 7-membered alkyleneiminocarbonyl or alkyleneimino,sulphonyl group optionally substituted by one or two alkyl groups,
- a 6- or 7-membered alkyleneiminocarbonyl or alkyleneiminosulphonyl group optionally substituted by one or two alkyl groups, wherein a methylene group of the alkyleneimino moiety is replaced in the 4 position by the group W, where W is as hereinbefore defined,
- a heteroaryl or heteroarylalkyl group,
- an alkoxy-C(═NH) or alkylsulphenyl-C(═NH)-group optionally substituted at the nitrogen atom by an alkyl group,
- an R10N═C(OR11), R10N═C(SR11), R10N═C(NHR11) or R10N═C(N-alkyl-NR11)-group, wherein
- R10 and R11 together denote an n-C2-4-alkylene group optionally substituted by one or two alkyl groups,
- an amidino group optionally substituted by one to three alkyl groups or
- an amidino group substituted by a hydroxy, alkoxy, cyano, alkoxycarbonyl or arylalkoxycarbonyl group, which may additionally be substituted at the nitrogen atoms by one or two alkyl groups,
- or a tautomer, stereoisomer or physiologically acceptable salt thereof,
- wherein, unless otherwise stated,
- the aryl moieties set forth above, either alone or as part of another group, each independently mean a phenyl group which in each case is optionally monosubstituted by
- R21, mono-, di- or trisubstituted by R22 or monosubstituted by R21 and additionally mono- or disubstituted by R22, wherein the substituents may be identical or different, and
- R21 denotes a cyano, carboxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, alkylcarbonyl, alkylsulphenyl, alkylsulphinyl, alkylsulphonyl, alkylsulphonyloxy, perfluoroalkyl, perfluoroalkoxy, nitro, amino, alkylamino, dialkylamino, alkylcarbonylamino, phenylalkylcarbonylamino, phenylcarbonylamino, alkylsulphonylamino, phenylalkylsulphonylamino, phenylsulphonylamino, N-alkyl-alkylcarbonylamino, N-alkyl-phenylalkylcarbonylamino, N-alkyl-phenylcarbonylamino, N-alkyl-alkylsulphonylamino, N-alkyl-phenylalkylsulphonylamino, N-alkyl-phenylsulphonylamino, aminosulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl, pyrrolidino, piperidino, morpholino, piperazino or 4-alkyl-piperazino group and
- R22 denotes an alkyl, hydroxy or alkoxy group, a fluorine, chlorine, bromine or iodine atom, while two groups R22 if they are bound to adjacent carbon atoms, may also denote an alkylene group with 3 to 6 carbon atoms, a 1,3-butadiene-1,4-diylene group or a methylenedioxy group,
- wherein the heteroaryl moieties set forth above, either alone or as part of another group, each independently mean a 5-membered heteroaromatic ring with an imino group, an oxygen or sulphur atom in the ring or a 5-membered heteroaromatic ring with an oxygen or sulphur atom and one to two nitrogen atoms in the ring or a 5-membered heteroaromatic ring with an imino group and one to three nitrogen atoms in the ring or a 6-membered heteroaromatic ring with one to three nitrogen atoms in the ring, wherein the abovementioned 5- and 6-membered heteroaromatic rings may be optionally substituted by one to two alkyl groups or by a trifluoromethyl group,
- and, unless otherwise stated, the abovementioned alkyl, alkylene and alkoxy moieties in each case contain 1 to 4 carbon atoms.
86 more elements
A trisubstituted pyrimidine of formula (I)
- wherein
- Ra denotes a hydrogen atom or an alkyl group,
- Rb denotes a phenyl group substituted by the groups R1 to R5, while
- R1 denotes a hydrogen, fluorine, chlorine, bromine or iodine atom,
- a C1-6-alkyl, hydroxy or C1-6-alkoxy group,
- a C3-6-cycloalkyl, C5-6-cycloalkoxy or (C3-6-cycloalkyl)alkyl group, which may be substituted in the cycloalkyl moiety by one or two alkyl groups in each case, a C2-5-alkenyl, C3-5-alkenyloxy, C2-5-alkynyl or C3-5-alkynyloxy group, wherein the vinyl and ethynyl moieties cannot be linked with an oxygen atom, an aryl, aryloxy, arylalkyl, arylalkoxy, alkylsulphenyl, alkylsulphinyl, alkylsulphonyl, alkylsulphonyloxy, arylsulphenyl, arylsulphinyl, arylsulphonyl, arylalkylsulphenyl, arylalkylsulphinyl or arylalkylsulphonyl group, a methyl, methoxy, methylsulphenyl, methylsulphinyl or methylsulphonyl group substituted by 1 to 3 fluorine atoms,
- an ethyl, ethoxy, ethylsulphenyl, ethylsulphinyl or ethylsulphonyl group substituted by 1 to 5 fluorine atoms,
- a nitro, amino, alkylamino, dialkylamino or azido group,
- a 5- to 6-membered alkyleneimino group optionally substituted by one or two alkyl groups,
- a 6- or 7-membered alkyleneimino group optionally substituted by one or two alkyl groups, wherein a methylene group in the 4 position to the imino-nitrogen atom is replaced by the group W, where
- W denotes an oxygen or sulphur atom, a sulphinyl, sulphonyl, imino, N-alkyl-imino, N-formyl-imino, N-alkylcarbonyl-imino, N-cyan-imino, N-alkoxycarbonyl-imino or N-alkylsulphonyl-imino group,
- a formylamino, N-alkyl-formylamino, alkylcarbonylamino, N-alkyl-alkylcarbonylamino, alkylsulphonylamino or N-alkyl-alkylsulphonylamino group, an alkylcarbonyl, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or cyano group,
- an aminosulphonyl, alkylaminosulphonyl or dialkylaminosulphonyl group,
- an alkyl or alkoxy group substituted by R9, wherein
- R9 denotes a hydroxy, alkoxy, amino, alkylamino, dialkylamino, alkylsulphenyl, alkylsulphinyl, alkylsulphonyl, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or cyano group,
- a 4- to 7-membered alkyleneimino group optionally substituted by one or two alkyl groups,
- a 6- or 7-membered alkyleneimino group optionally substituted by one or two alkyl groups, wherein a methylene group in the 4 position is replaced by the group W, where W is as hereinbefore defined,
- a formylamino, N-alkyl-formylamino, alkylcarbonylamino, N-alkyl-alkylcarbonylamino, alkylsulphonylamino, N-alkyl-alkylsulphonylamino, perfluoroalkylsulphonylamino, N-alkyl-perfluoroalkylsulphonylamino, alkoxycarbonylamino, N-alkyl-alkoxycarbonylamino, cyanoamino or N-alkyl-cyanoamino group,
- R2 and R3 in each case independently of one another denote hydrogen, fluorine, chlorine, bromine or iodine atoms, alkyl, alkoxy, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy or cyano groups or
- R2 together with R3, if they are bound to adjacent carbon atoms, also denote a methylenedioxy group optionally substituted by one or two alkyl groups, an n-C3-6-alkylene group optionally substituted by one or two alkyl groups, wherein a methylene group may be replaced by the group W′, where W′ has the meanings given above for W and additionally denotes a trifluoroacetylimino group, a 1,3-butadiene-1,4-diylene group optionally substituted by a fluorine, chlorine, bromine or iodine atom, by an alkyl, trifluoromethyl, hydroxy, alkoxy, trifluoromethoxy or cyano group, while the abovementioned 1,3-butadiene-1,4-diylene groups may additionally be substituted by a fluorine or chlorine atom, by an alkyl, trifluoromethyl or alkoxy group,
- R4 and R5, which may be identical or different, denote hydrogen, fluorine or chlorine atoms,
- Rc denotes a C1-6-alkyl group, which may be substituted by one or more hydroxy, alkoxy, dialkylamino groups,
- Rd denotes a hydrogen atom or a C1-6-alkyl group, and
- Re denotes a nitro, amino, alkylamino, dialkylamino or azido group,
- a 5- to 7-membered alkyleneimino group optionally substituted by one or two alkyl groups,
- a 5- to 7-membered alkyleneimino group optionally substituted by one or two alkyl groups, wherein one or two methylene groups adjacent to the nitrogen atoms may be replaced by a carbonyl group, while additionally in the alkyleneimino group a methylene group in the 4 position to the imino-nitrogen atom may be replaced by the group W where W is as hereinbefore defined, a formylamino, N-alkyl-formylamino, alkylcarbonylamino, N-alkyl-alkylcarbonylamino, di(alkylcarbonyl)amino, (C3-7-cycloalkyl)carbonylamino, N-alkyl-(C3-7-cycloalkyl)carbonylamino, (C3-7-cycloalkyl)alkylcarbonylamino, N-alkyl-(C3-7-cycloalkyl)alkylcarbonylamino, arylcarbonylamino, N-alkyl-arylcarbonylamino, arylalkylcarbonylamino, N-alkyl-arylalkylcarbonylamino, heteroarylcarbonylamino, N-alkyl-heteroarylcarbonylamino, heteroarylalkylcarbonylamino, N-alkyl-heteroarylalkylcarbonylamino, alkoxycarbonylamino, N-alkyl-alkoxycarbonylamino, arylalkoxycarbonylamino, N-alkyl-arylalkoxycarbonylamino, aryloxycarbonylamino, N-alkyl-aryl-oxycarbonylamino, (C4-7-cycloalkoxy)carbonylamino, N-alkyl-(C4-7-cycloalkoxy)carbonylamino, (C3-7-cycloalkyl)alkoxycarbonylamino, N-alkyl-(C3-7-cycloalkyl)alkoxycarbonylamino, alkylsulphonylamino, N-alkyl-alkylsulphonylamino, di(alkylsulphonyl)amino, C3-7-cycloalkylsulphonylamino, N-alkyl-C3-7-cycloalkylsulphonylamino, (C3-7-cycloalkyl)alkylsulphonylamino, N-alkyl-(C3-7-cycloalkyl)alkylsulphonylamino, arylsulphonylamino, N-alkyl-arylsulphonylamino, arylalkylsulphonylamino, N-alkyl-arylalkylsulphonylamino, heteroarylsulphonylamino, N-alkyl-heteroarylsulphonylamino, heteroarylalkylsulphonylamino, N-alkyl-heteroarylalkylsulphonylamino, cyanoamino or N-alkyl-cyanoamino group, while in each case the alkyl moiety of these groups may be substituted by the group R9 and R9 is as hereinbefore defined, and the cycloalkyl moieties of these groups may be substituted by one or two alkyl groups and additionally a CH2 group in the cycloalkyl moieties of the abovementioned groups is replaced by the group W, where W is as hereinbefore defined,
- a C2-5-alkenylcarbonylamino, N-alkyl-C2-5-alkenylcarbonylamino, C2-5-alkynylcarbonylamino, N-alkyl-C2-5-alkynylcarbonylamino, perfluoroalkylcarbonylamino, N-alkyl-perfluoroalkylcarbonylamino, perchloroalkylcarbonylamino, N-alkyl-perchloroalkylcarbonylamino, perfluoroalkylsulphonylamino or N-alkyl-perfluoroalkylsulphonylamino group, an alkyleneiminocarbonylamino or N-alkyl-alkyleneiminocarbonylamino group optionally substituted in the alkyleneimino moiety by one or two alkyl groups, while the alkyleneimino moiety is 4- to 7-membered in each case,
- an alkyleneiminocarbonylamino or N-alkyl-alkyleneiminocarbonylamino group optionally substituted in the alkyleneimino moiety by one or two alkyl groups, while the alkyleneimino moiety is 6- or 7-membered in each case and a methylene group in the 4 position of the alkyleneimino moiety is in each case replaced by the group W, where W is as hereinbefore defined,
- an alkyleneiminothiocarbonylamino or N-alkyl-alkyleneiminothiocarbonylam ino group optionally substituted in the alkyleneimino moiety by one or two alkyl groups, while the alkyleneimino moiety is 4- to 7-membered in each case, an alkyleneiminothiocarbonylamino or N-alkyl-alkyleneiminothiocarbonylamino group optionally substituted in the alkyleneimino moiety by one or two alkyl groups, while the alkyleneimino moiety is 6- or 7-membered in each case and in each case a methylene group in the 4 position of the alkyleneimino moiety is replaced by the group W, where W is as hereinbefore defined,
- a R7NR8—CX—NR6 or R7NR8—SO2-NR6-group, wherein
- R6 denotes a hydrogen atom or an alkyl group,
- R7 and R8, which may be identical or different, denote hydrogen atoms or alkyl groups optionally substituted by R9 or
- R6 and R7 together denote an n-C2-3-alkylene group and
- R8 denotes a hydrogen atom or an alkyl group optionally substituted by
- R9, while R9 is as hereinbefore defined, and
- X denotes O or S,
- an imidazolidine-2,4-dion-1-yl or imidazolidine-2,4-dion-3-yl-group optionally substituted by an alkyl group,
- a (R14NR15)-R13C═N-group wherein
- R13 denotes a hydrogen atom, an alkyl or C3-7-cycloalkyl group,
- R14 and R15, which may be identical or different, in each case denote an alkyl group, or
- R14 and R15 together with the nitrogen atom between them denote a 4- to 7-membered alkyleneimino group optionally substituted by one or two alkyl groups or a 6- or 7-membered alkyleneimino group optionally substituted by one or two alkyl groups, wherein a methylene group in the 4 position is replaced by the group W, where W is as hereinbefore defined, and
- R13 denotes a hydrogen atom, an alkyl or C3-7-cycloalkyl group,
- a (R18N═)CR16-R17N-group, wherein
- R16 denotes a hydrogen atom, an alkyl, C3-7-cycloalkyl, trifluoromethyl or trichloromethyl group,
- R17 and R18 in each case independently of one another denote a hydrogen atom or an alkyl group, or
- R16 and R18 together denote an n-C3-5-alkylene group optionally substituted by one or two alkyl groups, and
- R17 denotes a hydrogen atom or an alkyl group, or
- R17 and R18 together denote an n-C2-4-alkylene group optionally substituted by one or two alkyl groups, and
- R16 denotes a hydrogen atom, an alkyl or C3-7-cycloalkyl group,
- an (R19R20PO)-NH-group optionally substituted at the nitrogen atom by an alkyl group wherein
- R19 and R20, which may be identical or different, denote alkyl groups,
- an alkyl or alkoxy group substituted by R9, wherein R9 is as hereinbefore defined, a formyl, alkylcarbonyl, 1-(hydroxyimino)alkyl, 1-(alkoxyimino)alkyl, carboxy, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or cyano group,
- a sulpho, alkoxysulphonyl, aminosulphonyl, alkylaminosulphonyl or dialkylaminosulphonyl group,
- a 4- to 7-membered alkyleneiminocarbonyl or alkyleneiminosulphonyl group optionally substituted by one or two alkyl groups,
- a 6 or 7-membered alkyleneiminocarbonyl or alkyleneiminosulphonyl group optionally substituted by one or two alkyl groups, wherein a methylene group of the alkyleneimino moiety in the 4 position is replaced by the group W, where W is as hereinbefore defined,
- a heteroaryl or heteroarylalkyl group,
- an alkoxy-C(═NH) or alkylsulphenyl-C(═NH)-group optionally substituted at the nitrogen atom by an alkyl group,
- an R10N═C(OR11), R10N═C(SR11), R10N═C(NHR11) or R10N═C(N-alkyl-NR11)-group, wherein
- R10 and R11 together denote an n-C2-4-alkylene group optionally substituted by one or two alkyl groups,
- an amidino group optionally substituted by one to three alkyl groups or an amidino group substituted by a hydroxy, alkoxy, cyano, alkoxycarbonyl or arylalkoxycarbonyl group, which may additionally be substituted at the nitrogen atoms by one or two alkyl groups,
- wherein the aryl moieties set forth above, either alone or as part of another group, each independently mean a phenyl group which in each case is optionally monosubstituted by R21, mono-, di- or trisubstituted by R22 or monosubstituted by R21 and additionally mono- or disubstituted by R22, while the substituents may be identical or different, and
- R21 denotes a cyano, carboxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, alkylcarbonyl, alkylsulphenyl, alkylsulphinyl, alkylsulphonyl, alkylsulphonyloxy, perfluoroalkyl, perfluoroalkoxy, nitro, amino, alkylamino, dialkylamino, alkylcarbonylamino, phenylalkylcarbonylamino, phenylcarbonylamino, alkylsulphonylamino, phenylalkylsulphonylamino, phenylsulphonylamino, N-alkyl-alkylcarbonylamino, N-alkyl-phenylalkylcarbonylamino, N-alkyl-phenylcarbonylamino, N-alkyl-alkylsulphonylamino, N-alkyl-phenylalkylsulphonylamino, N-alkyl-phenylsulphonylamino, aminosulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl, pyrrolidino, piperidino, morpholino, piperazino or 4-alkyl-piperazino group and
- R22 denotes an alkyl, hydroxy or alkoxy group, a fluorine, chlorine, bromine or iodine atom, while two groups R22, if they are bound to adjacent carbon atoms, may also denote an alkylene group with 3 to 6 carbon atoms, a 1,3-butadiene-1,4-diylene group or a methylenedioxy group,
- wherein the heteroaryl moieties set forth above, either alone or as part of another group, each independently mean a 5-membered heteroaromatic ring with an imino group, an oxygen or sulphur atom in the ring or a 5-membered heteroaromatic ring with an oxygen or sulphur atom and one to two nitrogen atoms in the ring or a 5-membered heteroaromatic ring with an imino group and one to three nitrogen atoms in the ring or a 6-membered heteroaromatic ring with one to three nitrogen atoms in the ring, wherein the abovementioned 5- and 6-membered heteroaromatic rings may be optionally substituted by one to two alkyl groups or by a trifluoromethyl group,
- and, unless otherwise stated, the abovementioned alkyl, alkylene and alkoxy moieties in each case contain 1 to 4 carbon atoms,
- or a tautomer, stereoisomer or salt thereof.
63 more elements
A compound selected from:
- 2-(4-chloroanilino)-4-methylamino-5-nitro-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-amino-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-methylsulphonamino-pyrimidine;
- 2-(3,4-dichloroanilino)-4-(3-dimethylaminopropyl)-amino-5-nitro-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-acetamido-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(N-methyl-N-methylsulphonylamino)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(2-oxo-imidazolidin-1-yl)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(morpholin-1-ylcarbonylamino)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(N2,N2-dimethylureido)-pyrimidine;
- 2-[N-(3,4-dichlorophenyl)-N-methylamino]-4-methylamino-5-(2-oxo-imidazolidin-1-yl)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(2-oxo-tetrahydropyrimidin-1-yl)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-ureido-pyrimidine;
- 2-(3,4-dichloroanilino)-4-dimethylamino-5-(morpholin-1-ylcarbonylamino)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-ethylamino-5-(morpholin-1-ylcarbonylamino)-pyrimidine;
- 2-(3-chloroanilino)-4-methylamino-5-(morpholin-1-ylcarbonylamino)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(pyrrolidin-1-ylcarbonylamino)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(4-methylpiperazin-1-ylcarbonylamino)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-[N2,N2-di-(2-methoxyethyl)-ureido]-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(azepanyl-1-carbonylamino)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(N2,N2-diethylureido)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(piperazin-1-ylcarbonylamino)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(4-acetylpiperazin-1-ylcarbonylamino)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-[N2-methyl-N2-(2-hydroxyethyl)-ureido]-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(morpholin-1-ylthiocarbonylamino)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-(2,2,2-trifluoroacetamido)-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-[N2-methyl-N2-(2-dimethylaminoethyl)-ureido]-pyrimidine;
- 2-(3,4-dichloroanilino)-4-methylamino-5-[N2-methyl-N2-(3-dimethylaminopropyl)-ureido]-pyrimidine;
- and the salts thereof.
25 more elements
Dependencies are inferred from the claim text.