New anthracene derivatives and their use as pharmaceutical preparations
OwnerPeter Emig, Eckhard Gunther +4inventors
InventorsPeter Emig, Eckhard Gunther, Beate Aue, Emmanuel Polymeropoulos, Silke Baasner, Peter Schmidt
Life of this patent
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Abstract
The invention relates to new anthracene derivatives of the general Formula 1 and to their synthesis and use as pharmaceutical preparations, especially for the treatment of a tumor. 1
Claims18
A compound having the Formula 1
- 7
- in which
- R, R1, R2, R3 are each independently linked to any one of the C1 to C10 aromatic carbon atoms of anthracene, wherein only one of the R, R1, R2, R3 is linked to any one of the C:
- to C10 aromatic carbon atoms, wherein R. R., R2, R3 alternatively are the same or different, and independently of one another, represent hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(Ca-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl, aryl, the aryl group being unsubstituted or a linear or branched (C1-C8)-alkyl, substituted one or more times, similarly or differently, with halogen, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, cyano, isocyano, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl substituted with one or more halogen atoms, preferably trifluoromethyl, (C2-C6)-alkenyl, preferably allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- Z is oxygen or sulfur, the
- 8
- group, which is a substituent on the anthracene compound, is linked to any one of the C1-C10 carbon atoms of the ring structure;
- n, m independently of one another, is a whole number from 1 to 4;
- R4 is a linear or branched (C1-C12)-alkyl group, which is saturated or unsaturated with one to three double bonds and/or triple bonds and is unsubstituted or alternatively substituted at the same or at different carbon atoms with one, two or more aryl, heteroaryl, halogen, cyano, (C1-C6)-alkoxycarbonylamino, (C1-C6)-alkoxy, amino, mono-(C1-C4)-alkylamino or di-(C1-C4)-alkylamino, a (C6-C14)-aryl group, (C6-C14)-aryl-(C1-C4)-alkyl group or a (C2-C10)-heteroaryl or (C2-C10)-heteroaryl-(C1-C4)-alkyl group, containing one or more hetero atoms selected from the group comprising nitrogen, oxygen and sulfur, the (C1-C4)-alkyl group being unsubstituted or substituted one or more times, identically or differently with (C1-C6)-alkyl or halogen and the (C6-C14)-aryl or (C2-C10)-heteroaryl group represent unsubstituted or substituted, one or more times with the same or different linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl.
A compound having Formula 1
- 9
- in which
- R, R1, R2, R3 are each independently linked to any one of the C1 to C10 aromatic carbon atoms of anthracene, wherein only one of the R, R1, R2, R3 is linked to any one of the C:
- to C10 aromatic carbon atoms, wherein R, R1, R2, R3 alternatively are the same or different, and independently of one another, represent hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl, aryl, the aryl group being unsubstituted or a linear or branched (C1-C8)-alkyl, substituted one or more times, similarly or differently, with halogen, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, cyano, isocyano, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl substituted with one or more halogen atoms, preferably trifluoromethyl, (C2-C6)-alkenyl, preferably allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- Z is oxygen or sulfur, the
- 10
- group, which is a substituent on the anthracene compound, is linked to any one of the C1-C10 carbon atoms of the ring structure;
- n, m independently of one another, is a whole number from 1 to 4;
- R4 is a phenyl or a naphthyl group, which is unsubstituted or substituted once or repeatedly with the same or different linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 4-, 5- or 6-pyrimidinyl group or a 2-, 4-, 5- or 6-pyrimidinyl-(C1-C4)-alkyl group, the (C1-C4)-alkyl group being unsubstituted or substituted, once or repeatedly, identically or differently, with (C1-C6)-alkyl or halogen, and the 2-, 4-, 5- or 6-pyrimidinyl group being unsubstituted or substituted one to three times with the same or different, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 3-, 4-, 5- or 6-pyridazinyl group or a 3-, 4-, 5- or 6-pyridazinyl-(C1-C4)-alkyl group, the (C1-C4)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 3-, 5- or 6-pyrazinyl group or a 2-, 3-, 5- or 6-pyrazinyl-(C1-C4)-alkyl group, the (C1-C4)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl, halogen and the 2-, 3-, 5-, or 6-pyrazinyl group being unsubstituted or substituted one to three times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 3-, 4-, 5-, 6-, 7- or 8-cinnolinyl group or a 3-, 4-, 5-, 6-, 7- or 8-cinnolinyl-(C1-C4)-alkyl group, the (C1-C4)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl, halogen and the 3-, 4-, 5-, 6-, 7- or 8-cinnolinyl group being unsubstituted or substituted one to five times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 4-, 5-, 6-, 7- or 8-quinazolinyl group or a 2-, 4-, 5-, 6-, 7- or 8-quinazolinyl-(C1-C4)-alkyl group, the (C1-C4)-alkyl group being substituted one or more times, identically or differently, with hydrogen, (C1-C6)-alkyl, halogen, and the 2-, 4-, 5-, 6-, 7- or 8-quinazolinyl group being substituted one to five times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 3-, 5-, 6-, 7- or 8-quinoxalinyl group or a 2-, 3-, 5-, 6-, 7- or 8-quinoxalinyl-(C1-C4)-alkyl group, the (C1-C4)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen and the 2-, 3-, 5-, 6-, 7- or 8-quinoxalinyl group being unsubstituted one to five times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 1-, 4-, 5-, 6-, 7-, or 8-phthalazinyl group or a 1-, 4-, 5-, 6-, 7-, or 8-phthalazinyl-(C1-C4)-alkyl group, the (C1-C4)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen and the 1-, 4-, 5-, 6-, 7- or 8-phthalazinyl group being substituted one to five times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, being substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 3-, 4-, 5-, 6-, 7- or 8-quinolyl group or a 2-, 3-, 4-, 5-, 6-, 7- or 8-quinolyl-(C1-C4)-alkyl group, the (C1-C4)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 2-, 3-, 4-, 5-, 6-, 7- or 8-quinolyl group being substituted one to six times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, being substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 1-, 3-, 4-, 5-, 6-, 7- or 8-isoquinolyl or a 1-, 3-, 4-, 5-, 6-, 7- or 8-isoquinolyl-(C1-C4)-alky group, the (C1-C4)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 1-, 3-, 4-, 5-, 6-, 7- or 8-isoquinolyl group being substituted one to six times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, being substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 6-, 8- or 9-[9H]-purinyl group or 2-, 6-, 8- or 9-[9H]-purinyl-(C1-C4)-alkyl group, the (C1-C4)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 2-, 6-, 8- or 9-[9H]-purinyl group being substituted one to three times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 6-, 7- or 8-[7H]-purinyl group or 2-, 6-, 7- or 8-[7H]-purinyl-(C1-C4)-alkyl group, the (C1-C4)-alkyl group being unsubstituted or substituted one or more times, identically or differently with (C1-C6)-alkyl or halogen, and the 2-, 6-, 7- or 8-[7H]-purinyl group being substituted one to three times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-acridinyl or a 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-acridinyl-(C1-C4)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen and the 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-acridinyl group being substituted one to eight times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8 or 9-phenanthridinyl or a 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-phenanthridinyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently with hydrogen, (C1-C6)-alkyl, or halogen, and the 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-phenanthridinyl group being unsubstituted or substituted one to eight times, identically or differently with linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 3-, 4-, 5- or 6-pyridyl group, the 2-, 3-, 4-, 5- or 6-pyridinyl group being substituted one to four times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 3-, 4-, 5- and 6-pyridyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 2-, 3-, 4-, 5- or 6-pyridinyl group being substituted one to four times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 3-, 4- or 5-thienyl group or a 2-, 3-, 4- or 5-thienyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen and the 2-, 3-, 4- or 5-thienyl group being substituted one to three times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 4- or 5-thiazolyl group or a 2-, 4- or 5-thiazolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen and the 2-, 4- or 5-thiazolyl group being substituted once or twice, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, with or more substituted halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 3-, 4- or 5-isothiazolyl group or a 3-, 4- or 5-isothiazolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently with (C1-C6)-alkyl or halogen, and the 3-, 4- or 5-isothiazolyl group being substituted once or twice, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 4-, 5-, 6- or 7-benzthiazolyl group or a 2-, 4-, 5-, 6- or 7-benzthiazolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 2-, 4-, 5-, 6- or 7-benzthiazolyl group being substituted one to four times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 1-, 2-, 4- or 5-imidazolyl group or a 1-, 2-, 4- or 5-imidazolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen and the 1-, 2-, 4- or 5-imidazolyl group being substituted one to three times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 1-, 3-, 4- or 5-pyrazolyl group or a 1-, 3-, 4- or 5-pyrazolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 1-, 3-, 4- or 5-pyrazolyl group being substituted one to three times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 1-, 2-, 3-, 4- or 5-pyrrolyl group or a 1-, 2-, 3-, 4- or 5-pyrrolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 1-, 2-, 3-, 4- or 5-pyrrolyl group being substituted one to four times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, with or more substituted halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 1-, 3- or 5-[1,2,4]-triazolyl group or 1-, 3- or 5-[1,2,4]-triazolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being substituted one or more times, identically or differently, with hydrogen, (C1-C6)-alkyl or halogen and the 1-, 3- or 5-[1,2,4]-triazolyl group, unsubstituted or substituted once or twice, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 1,4- or 5-[1.2.3]-triazolyl group or a 1-, 4- or 5-[1.2.3]-triazolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen and the 1-, 4- or 5-[1.2.3]-triazolyl group being substituted once or twice, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 1- or 5-[1H]-tetrazolyl group or a 1- or 5-[1H]-tetrazolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 1- or 5-[1H]-tetrazolyl group being substituted with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2- or 5-[2H]-tetrazolyl group or a 2- or 5-[2H]-tetrazolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 2- or 5-[2H]-tetrazolyl group being substituted with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 4- or 6-[1.3.5]-triazinyl group or a 2-, 4- or 6-[1.3.5]-triazinyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with hydrogen, (C1-C6)-alkyl or halogen and the 2-, 4- or 6-[1.3.5]-triazinyl group being substituted once or twice, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, with or more substituted halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 2-, 4- or 5-oxazolyl group or a 2-, 4- or 5-oxazolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 2-, 4- or 5-oxazolyl group being substituted once or twice, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 3-, 4- or 5-isoxazolyl group or a 3-, 4- or 5-isoxazolyl-(C1-C6) group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 3-, 4- or 5-isoxazolyl group being substituted once or twice, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl;
- a 1-, 2-, 3-, 4-, 5-, 6- or 7-indolyl group or a 1-, 2-, 3-, 4-, 5-, 6- or 7-indolyl-(C1-C6)-alkyl group, the (C1-C6)-alkyl group being unsubstituted or substituted one or more times, identically or differently, with (C1-C6)-alkyl or halogen, and the 1-, 2-, 3-, 4-, 5-, 6- or 7-indolyl group being substituted one to six times, identically or differently, with hydrogen, linear or branched (C1-C8)-alkyl, (C3-C7)-cycloalkyl, linear or branched (C1-C8)-alkylcarbonyl, preferably acetyl, hydroxy, linear or branched (C1-C8)-alkoxy, preferably methoxy and ethoxy, halogen, linear or branched aryl-(C1-C8)-alkoxy, preferably benzyloxy or phenylethyloxy, trityloxy, trimethylsilyloxy, amino, mono-(C1-C4)-alkylamino, di-(C1-C4)-alkylamino, (C2-C5)-cycloalkylamino, morpholino, heterocyclic-(C1-C6)-alkoxy, carboxy, imidocarboxy, carboxamidine, linear or branched (C1-C8)-alkoxycarbonylamino, linear or branched (C1-C8)-alkylcarbonylamino, preferably acetamino, sulfonyloxy, sulfenyloxy, sulfinyloxo, nitro, nitroso, thio, linear or branched (C1-C8)-alkylthio, linear or branched (C1-C8)-alkylsulfo, linear or branched (C1-C8)-alkylsulfoxy, cyano, isocyano, linear or branched cyano-(C1-C6)-alkyl, preferably cyanomethyl, linear or branched (C1-C8)-alkoxycarbonyl, linear or branched (C1-C4)-alkyl, substituted with one or more halogen atoms, 1 preferably trifluoromethyl, linear or branched carboxy-(C1-C8)-alkyl, linear or branched (C1-C8)-alkoxycarbonyl-(C1-C6)-alkyl, (C2-C6)-alkenyl, preferably, allyl, (C2-C6)-alkinyl, preferably ethinyl or propargyl.
A compound having one of the following formulas:
- Anthracene-9-yl-[4-(4-nitro-phenyl)-piperazine-1-yl]-methanone;
- Anthracene-9-yl-[4-(3,5-dimethoxy-phenyl)-piperazine-1-yl]-methanone;
- Anthracene-9-yl-[4-phenyl)-piperazine-1-yl]-methanone;
- Anthracene-9-yl-(4-naphthalene-1-yl-piperazine-1-yl)-methanone;
- Anthracene-9-yl-(4-biphenyl-2-yl-piperazine-1-yl)-methanone;
- Anthracene-9-yl-[4-(3-hydroxy-phenyl)-piperazine-1-yl]-methanone;
- Anthracene-9-yl-[4-(4-trifluoromethyl-pyridine-2-yl)-piperazine-1-yl]-methanone;
- Anthracene-9-yl-[4-(6-methyl-pyridine-2-yl)-piperazine-1-yl]-methanone;
- Anthracene-9-yl-(2,3,5,6-tetrahydro-[1,2′]-bipyrazinyl-4-yl)-methanone;
- 2-[4-(Anthracene-9-carbonyl)-piperazine-1-yl]-nicotinnitrile;
- Anthracene-9-yl-[4-(5-trifluoromethyl-pyridine-2-yl)-piperazine-1-yl]-methanone;
- and
- Anthracene-9-yl-(4-pyridine-2-yl-piperazine-1-yl)-methanone.
A method for making an anthracene compound comprising contacting an acridinecarboxylic acid of Formula 2, wherein Z is oxygen or sulfur, and Y is a leaving group selected from the group of halogen, C1-C6 alkoxy, —O-tosyl, —O-mesyl, tetrazolyl and imidazolyl,
- 11
- with an amine of Formula 3.
Dependencies are inferred from the claim text.