2-heterocyclically substituted dihydropyrimidines
First Claim
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1. A dihydroxypyrimidine of the general formula (I) or its isomeric form (Ia)
in whichR1 represents phenyl, furyl, thienyl, pyridyl, cycloalkyl having 3 to 6 carbon atoms or a radical of the formula
- where the abovementioned ring systems are optionally monosubstituted or polysubstituted in an identical or different manner, by substituents selected from the group consisting of halogen, trifluoromethyl, nitro, cyano, trifluoromethoxy, carboxyl, hydroxyl, (C1-C6)-alkoxy, (C1-C6)-alkoxycarbonyl and (C1-C6)-alkyl, which for its part can be substituted by aryl having 6 to 10 carbon atoms or halogen, and/or the ring systems mentioned are optionally substituted by groups of the formula —
S—
R6, NR7R8, CO—
NR9R10, SO2—
CF3 and —
A—
CH2—
R11,
in which R6 is phenyl which is optionally substituted by halogen, R7, R8, R9 and R10 are identical or different and are hydrogen, phenyl, hydroxy-substituted phenyl, hydroxyl, (C1-C6)-acyl or (C1-C6)-alkyl, which for its part can be substituted by hydroxyl, (C1-C6)-alkoxycarbonyl, phenyl or hydroxy-substituted phenyl, A is a radical O, S, SO or SO2, R11 is phenyl which is optionally mono- to polysubstituted, in an identical or different manner, by substituents selected from the group consisting of halogen, nitro, trifluoromethyl, (C1-C6)-alkyl and (C1-C6)-alkoxy, R2 represents a radical of the formula —
OR12 or —
NR13R14,
in which R12 is hydrogen, (C1-C6)-alkoxycarbonyl or a straight-chain, branched or cyclic, saturated or unsaturated (C1-C8)-hydrocarbon radical which optionally contains one or two identical or different hetero chain members from the group consisting of O, CO, NH, —
N—
(C1-C4)-alkyl, —
N—
((C1-C4)-alkyl)2, S and SO2 and which is optionally substituted by halogen, nitro, cyano, hydroxyl, aryl having 6 to 10 carbon atoms or aralkyl having 6 to 10 carbon atoms, or a group of the formula —
NR15R16,
in which R15 and R16 are identical or different and are hydrogen, benzyl or (C1-C6)-alkyl, R13 and R14 are identical or different and are hydrogen, (C1-C6)-alkyl or cycloalkyl having 3 to 6 carbon atoms, R3 represents hydrogen, amino or a radical of the formulaformyl, cyano or trifluoromethyl, or a straight-chain, branched or cyclic, saturated or unsaturated hydrocarbon radical having up to 8 carbon atoms, which is optionally mono- or polysubstituted, in an identical or different manner, by aryloxy having 6 to 10 carbon atoms, azido, cyano, hydroxyl, carboxyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylthio, (C1-C6)-alkoxy, which for its part can be substituted by azido or amino, and/or is substituted by triazolyl which for its part can be substituted up to 3 times by (C1-C6)-alkoxycarbonyl, and/or can be substituted by groups of the formula —
OSO2—
CH3 or (CO)a—
NR17R18,
in which a is a number 0 or 1, R17 and R18 are identical or different and are hydrogen or aryl, aralkyl having 6 to 10 carbon atoms, or are (C1-C6)-alkyl which is optionally substituted by (C1-C6)-alkoxycarbonyl, hydroxyl, phenyl or benzyl, where phenyl or benzyl are optionally mono- or polysubstituted, in an identical or different manner, by hydroxyl, carboxyl (C1-C6)-alkyl or (C1-C6)-alkoxy, NH—
CO—
CH3 or NH—
CO—
CF3, R4 represents hydrogen, (C1-C4)-alkyl, acetyl or benzoyl, D represents an oxygen or sulphur atom, R5 represents hydrogen, halogen or straight-chain or branched alkyl having up to 6 carbon atoms, or a salt thereof.
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Abstract
The invention relates to new 2-heterocyclically substituted dihydropyrimidines, medicaments which contain these 2-heterocyclically substituted dihydropyrimidines, and a process for preparation of medicaments. The invention furthermore relates to the use of the 2-heterocyclically substituted dihydropyrimidines for the production of a medicament, in particular for the treatment of acute or chronic viral diseases, in particular for the production of a medicament for the treatment of acute or chronic hepatitis B infections.
59 Citations
5 Claims
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1. A dihydroxypyrimidine of the general formula (I)
or its isomeric form (Ia) in which R1 represents phenyl, furyl, thienyl, pyridyl, cycloalkyl having 3 to 6 carbon atoms or a radical of the formula - where the abovementioned ring systems are optionally monosubstituted or polysubstituted in an identical or different manner, by substituents selected from the group consisting of halogen, trifluoromethyl, nitro, cyano, trifluoromethoxy, carboxyl, hydroxyl, (C1-C6)-alkoxy, (C1-C6)-alkoxycarbonyl and (C1-C6)-alkyl, which for its part can be substituted by aryl having 6 to 10 carbon atoms or halogen, and/or the ring systems mentioned are optionally substituted by groups of the formula —
S—
R6, NR7R8, CO—
NR9R10, SO2—
CF3 and —
A—
CH2—
R11,
in whichR6 is phenyl which is optionally substituted by halogen, R7, R8, R9 and R10 are identical or different and are hydrogen, phenyl, hydroxy-substituted phenyl, hydroxyl, (C1-C6)-acyl or (C1-C6)-alkyl, which for its part can be substituted by hydroxyl, (C1-C6)-alkoxycarbonyl, phenyl or hydroxy-substituted phenyl, A is a radical O, S, SO or SO2, R11 is phenyl which is optionally mono- to polysubstituted, in an identical or different manner, by substituents selected from the group consisting of halogen, nitro, trifluoromethyl, (C1-C6)-alkyl and (C1-C6)-alkoxy, R2 represents a radical of the formula —
OR12 or —
NR13R14,
in whichR12 is hydrogen, (C1-C6)-alkoxycarbonyl or a straight-chain, branched or cyclic, saturated or unsaturated (C1-C8)-hydrocarbon radical which optionally contains one or two identical or different hetero chain members from the group consisting of O, CO, NH, —
N—
(C1-C4)-alkyl, —
N—
((C1-C4)-alkyl)2, S and SO2 and which is optionally substituted by halogen, nitro, cyano, hydroxyl, aryl having 6 to 10 carbon atoms or aralkyl having 6 to 10 carbon atoms, or a group of the formula —
NR15R16,
in whichR15 and R16 are identical or different and are hydrogen, benzyl or (C1-C6)-alkyl, R13 and R14 are identical or different and are hydrogen, (C1-C6)-alkyl or cycloalkyl having 3 to 6 carbon atoms, R3 represents hydrogen, amino or a radical of the formula formyl, cyano or trifluoromethyl, or a straight-chain, branched or cyclic, saturated or unsaturated hydrocarbon radical having up to 8 carbon atoms, which is optionally mono- or polysubstituted, in an identical or different manner, by aryloxy having 6 to 10 carbon atoms, azido, cyano, hydroxyl, carboxyl, (C1-C6)-alkoxycarbonyl, (C1-C6)-alkylthio, (C1-C6)-alkoxy, which for its part can be substituted by azido or amino, and/or is substituted by triazolyl which for its part can be substituted up to 3 times by (C1-C6)-alkoxycarbonyl, and/or can be substituted by groups of the formula —
OSO2—
CH3 or (CO)a—
NR17R18,
in whicha is a number 0 or 1, R17 and R18 are identical or different and are hydrogen or aryl, aralkyl having 6 to 10 carbon atoms, or are (C1-C6)-alkyl which is optionally substituted by (C1-C6)-alkoxycarbonyl, hydroxyl, phenyl or benzyl, where phenyl or benzyl are optionally mono- or polysubstituted, in an identical or different manner, by hydroxyl, carboxyl (C1-C6)-alkyl or (C1-C6)-alkoxy, NH—
CO—
CH3 or NH—
CO—
CF3,R4 represents hydrogen, (C1-C4)-alkyl, acetyl or benzoyl, D represents an oxygen or sulphur atom, R5 represents hydrogen, halogen or straight-chain or branched alkyl having up to 6 carbon atoms, or a salt thereof. - View Dependent Claims (2, 3, 4, 5)
in which R1 represents phenyl, furyl, thienyl, pyridyl, cyclopentyl or cyclohexyl, where the abovementioned ring systems are optionally substituted one or 2 times, in an identical or different manner, by substituents selected from the group consisting of halogen, trifluoromethyl, nitro, SO2— - CF3, methyl, cyano, trifluoromethoxy, carboxyl, methoxycarbonyl or radicals of the formulae —
CO—
NH—
CH2—
C(CH3)3, —
CO—
NH(CH2)2OH, —
CO—
NH—
CH2—
C6H5, —
CO—
NH—
C6H5, —
O—
CH2—
C6H5, —
CO—
NH—
C6H4-pOH, or —
S—
C6H4-pCl;
R2 represents a radical of the formula —
OR12 or —
NR13R14,
in whichR12 is hydrogen, (C1-C4)-alkenyl or (C1-C4)-alkyl, which is optionally substituted by cyano, benzyl or by a radical of the formula —
NR15R16,
in whichR15 and R16 are identical or different and are hydrogen, methyl or ethyl, R13 and R14 are identical or different and are hydrogen, methyl, ethyl or cyclopropyl, R3 represents hydrogen or a radical of the formula represents formyl, cyano, trifluoromethyl or cyclopropyl, or represents (C1-C4)-alkyl which is optionally substituted by radicals of the formula —
SO2CH3, —
NH—
CO—
CH3, —
NH—
CO—
CF3, (C1-C3)-alkoxycarbonyl or hydroxyl,and/or alkyl is optionally substituted by groups of the formula —
OSO2—
CH3 or (CO)a—
NR17R18,
in whicha is a number 0 or 1, R17 and R18 are identical or different and are hydrogen, phenyl or benzyl, or are C1-C4-alkyl which is optionally substituted by (C1-C4)-alkoxycarbonyl, hydroxyl, phenyl or benzyl, where phenyl or benzyl are optionally mono- or polysubstituted, in an identical or different manner, by hydroxyl, carboxyl, (C1-C4)-alkyl or (C1-C4)-alkoxy, —
NH—
CO—
CH3 or —
NH—
CO—
CF3,or R4 represents hydrogen, methyl, ethyl or acetyl, D represents an oxygen or sulphur atom, R5 represents hydrogen, halogen or (C1-C4)-alkyl, or a salt thereof.
- where the abovementioned ring systems are optionally monosubstituted or polysubstituted in an identical or different manner, by substituents selected from the group consisting of halogen, trifluoromethyl, nitro, cyano, trifluoromethoxy, carboxyl, hydroxyl, (C1-C6)-alkoxy, (C1-C6)-alkoxycarbonyl and (C1-C6)-alkyl, which for its part can be substituted by aryl having 6 to 10 carbon atoms or halogen, and/or the ring systems mentioned are optionally substituted by groups of the formula —
-
3. A dihydropyrimidine according to claim 1 or 2,
in which R1 represents phenyl or thienyl, where the abovementioned ring systems are optionally substituted up to 2 times, in an identical or different manner, by substituents selected from the group consisting of fluorine, chlorine, methyl, trifluoromethyl or nitro, R2 represents a radical of the formula — - OR12 or —
NR13R14,
in whichR12 represents hydrogen or (C1-C4)-alkyl, R13 and R14 are identical or different and are hydrogen or methyl, R3 represents hydrogen or formyl, cyano, trifluoromethyl or cyclopropyl, or represents (C1-C3)-alkyl which is optionally substituted by hydroxyl, R4 represents hydrogen or methyl, D represents an oxygen or sulphur atom, R5 represents hydrogen, fluorine, chlorine or (C1-C3)-alkyl, or a salt thereof.
- OR12 or —
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4. A dihydropyrimidine according to claim 1,
in which R1 represents phenyl or thienyl, each of which is optionally substituted up to 2 times, in an identical or different manner, by fluorine or chlorine, R2 represents methoxy, ethoxy or n-propoxy, R3 represents hydrogen, methyl or cylcopropyl, R4 represents hydrogen, D represents an oxygen or sulphur atom, R5 represents hydrogen, fluorine or chlorine or a salt thereof. -
5. A pharmaceutical composition, comprising at least one compound of the general formula (I) or (Ia) according to claim 1 and a pharmaceutically acceptable auxiliary or excipient.
Specification
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Current AssigneeBayer AG
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Original AssigneeBayer AG
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InventorsPaessens, Arnold, Graef, Erwin, Goldmann, Siegfried, Lottmann, Stefan, Stoltefuss, Jürgen
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Primary Examiner(s)Ford, John M.
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Application NumberUS09/673,597Time in Patent Office811 DaysField of Search514/256, 544/333, 544/327, 544/328US Class Current514/256CPC Class CodesA61P 1/16 for liver or gallbladder di...C07D 413/04 directly linked by a ring-m...C07D 417/04 directly linked by a ring-m...
