CA2504153A1 - Pyrimidine-4,6-dicarboxylic acid diamides for selectively inhibiting collagenases - Google Patents

Pyrimidine-4,6-dicarboxylic acid diamides for selectively inhibiting collagenases Download PDF

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CA2504153A1
CA2504153A1 CA002504153A CA2504153A CA2504153A1 CA 2504153 A1 CA2504153 A1 CA 2504153A1 CA 002504153 A CA002504153 A CA 002504153A CA 2504153 A CA2504153 A CA 2504153A CA 2504153 A1 CA2504153 A1 CA 2504153A1
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pyrimidine
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twice
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CA2504153C (en
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Otmar Klingler
Reinhard Kirsch
Joerg Habermann
Klaus-Ulrich Weithmann
Christian Engel
Bernard Pirard
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Sanofi Aventis Deutschland GmbH
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Abstract

Pyrimidine-4,6-dicarboxamides of formula (I), are suitable for the selective inhibition of collagenase (MMP 13). The pyrimidine-4.6-dicarboxamides can thus be used for the treatment of degenerative joint diseases.

Claims (8)

1. A compound of the formula I

and/or all the stereoisomeric forms of the compound of the formula I
and/or mixtures of these forms in any ratio, and/or a physiologically tolerated salt of the compound of the formula I, wherein for the case a) R1 is hydrogen atom or-(C1-C6)-alkyl, R2 is -(C1-C6)-alkyl, where alkyl is substituted, once, twice or three times, by 1. -(C1-C6)-alkyl-O-(C6-C14)-aryl,
2. -(C0-C6)-alkyl-N(R8)-C(O)-O-(C1-C6)-alkyl, in which R8 is i) hydrogen atom ii) -(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by -NH2, -CN, -OH, -C(O)-OH, -C(O)-O-(C1-C6)-alkyl, -C(O)-NH-OH, NO2 or halogen, or iii) OH,
3. -(C(O)-N(R9)-(R10), in which R9 and R10 are identical or different and are, independently of each other, i) hydrogen atom or ii) -(C1-C6)-alkyl, or R9 and R10 form, together with the nitrogen atom to which they are bonded, a 5-, 6- or 7-membered saturated ring, where a heteroatom from the series oxygen, sulfur and nitrogen can also replace one or two further carbon atoms and, in the case of nitrogen, the nitrogen atoms can, independently of each other, be unsubstituted or substituted by (C1-C6)-alkyl,
4. -(C6-C14)-aryl, in which aryl is substituted, once, twice or three times, independently of each other, by 4.1) -phenyl, where the phenyl ring is unsubstituted or substituted once, twice or three times by 4.1.1) halogen 4.1.2) -(C1-C6)-alkyl, 4.1.3) -O-(C1-C6)-alkyl, 4.1.4) -S(O)2-R16, where R16 is (C1-C6)-alkyl or -NH2, 4.2) -(C0-C6)-alkyl-C(O)-N(R9)-(R10), in which R9 and R10 have the abovementioned meaning, 4.3) -(C0-C6)-alkyl-C(O)-NH-CN, 4.4) -(C0-C6)-alkyl-C(O)-(C0-C6)-alkyl-Het, where Het is a saturated or unsaturated, monocyclic or bicyclic, 3- to 10-membered heterocyclic ring system which contains 1, 2 or 3 identical or different ring heteroatoms from the series nitrogen, oxygen and sulfur and is unsubstituted or substituted, once, twice or three times, independently of each other, by a) halogen, b) cyano, c) nitro, d) hydroxyl, e) amino, f) -C(O)-O-(C1-C6)-alkyl, g) -C(O)-OH, h) -(C1-C6)-alkyl, where alkyl is unsubstituted or substituted, once, twice or three times, by halogen, i) -O-(C1-C6)-alkyl, where alkyl is unsubstituted or substituted, once, twice or three times, by halogen, or -N(R9)-(R10), j) =O, k) -Het, l) -(C2-C6)-alkenyl, where alkenyl is unsubstituted or substituted, once, twice or three times, by halogen, or -N(R9)-(R10), or m) -(C2-C6)-alkynyl, where alkynyl is unsubstituted or substituted, once, twice or three times, by halogen or -N(R9)-(R10), 4.5) -(C0-C6)-alkyl-C(O)-(C1-C6)-alkyl-OH, 4.6) -O-(C0-C6)-alkyl-C(O)-N(R9)-(R10), in which R9 and R10 have the abovementioned meaning, 4.7) -S(O)y-(C1-C6)-alkyl-C(O)-O-R8, in which R8 has the abovementioned meaning and y is 1 or 2, 4.8) -S(O)z-(C1-C6)-alkyl-C(O)-N(R9)-(R10), in which R9 and R10 have the abovementioned meaning and z is zero, 1 or 2, 4.9) -(C0-C6)-alkyl-C(O)-N(R8)-(C0-C6)-alkyl-N(R9)-(R10), in which R8, R9 and R10 have the abovementioned meaning, 4.10) -(C0-C6)-alkyl-C(O)-N(R8)-(C0-C6)-alkyl-Het, where R8 has the abovementioned meaning and Het has the abovementioned meaning and is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.11) -(C0-C6)-alkyl-C(O)-N(R8)-(C0-C6)-alkyl-(C6-C14)-aryl, where aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.12) -(C1-C6)-alkyl-N(R9)-(R10), in which R9 and R10 are identical or different and are, independently of each other, hydrogen atom or -(C1-C6)-alkyl, or -(C0-C6)-alkyl-N(R9)-(R10) in which R9 and R10 form, together with the nitrogen atom to which they are bounded, a 5-, 6- or 7-membered saturated ring, where a heteratom from the series oxygen, sulfur and nitrogen can also replace one or two further carbon atoms and, in the case of nitrogen, the nitrogen atoms can, independently of each other, be unsubstituted or substituted by (C1-C6)-alkyl, have the abovementioned meaning, 4.13) -(CH2)y-N(R8)-C(O)-(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m) and y is 1 or 2, 4.14) -(C0-C4)-alkyl-N(R8)-C(O)-(C0-C6)-alkyl-(C6-C14)-aryl, in which aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.15) -(C0-C4)-alkyl-N(R8)-C(O)-(C0-C6)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.16) -(C0-C4)-alkyl-N(R8)-C(O)-O-(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.17) -(C0-C4)-alkyl-N(R8)-C(O)-O-(C1-C6)-alkenyl, in which alkenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.18) -(C0-C4)-alkyl-N(R8)-C(O)-O-(C1-C6)-alkynyl, in which alkynyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.19) -(C0-C4)-alkyl-N(R8)-C(O)-O-(C0-C6)-alkyl-(C6-C14)-aryl, in which aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.20) -(C0-C4)-alkyl-N(R8)-C(O)-O-(C0-C6)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21) -(C0-C4)-alkyl-N(R8)-C(O)-(C0-C6)-alkyl-N(R11)-R12, in which R8 has the abovementioned meaning and R11 and R12 are identical or different and are, independently of each other, 4.21.1) a hydrogen atom, 4.21.2) -(C1-C6)-alkyl, 4.21.3) -(C0-C6)-alkyl-(C6-C14)-aryl, in which aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.4) -(C0-C6)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.5) -C(O)-(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.6) -C(O)-(C3-C6)-cycloalkyl, in which cycloalkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.7) -C(O)-(C0-C6)-alkyl-(C6-C14)-aryl, in which aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.8) -C(O)-(C0-C6)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.9) -SO2-(C0-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.10) -NH-SO2-(C0-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.11) -SO2-(C0-C6)-alkyl-(C6-C14)-aryl-(C0-C6)-alkyl, in which aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.12) -SO2-(C0-C6)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.22) -(C0-C4)-alkyl-N(R8)-S(O)2-(C0-C6)-alkyl-(C6-C14)-aryl, in which aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m) and R8 has the abovementioned meaning, 4.23) -(C0-C4)-alkyl-N(R8)-S(O)2-(C0-C6)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m) and R8 has the abovementioned meaning, 4.24) -(C0-C4)-alkyl-N(R8)-S(O)2-N(R8)-(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m) and R8 has the abovementioned meaning, 4.25) -(C0-C4)-alkyl-N(R8)-S(O)2-N(R8)-(C0-C6)-alkyl-(C6-C14)-aryl, in which aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m) and R8 has the abovementioned meaning, 4.26) -(C0-C4)-alkyl-N(R8)-S(O)2-N(R8)-(C0-C6)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m) and R8 has the abovementioned meaning, 4.27) -(C0-C4)-alkyl-N(R8)-C(O)-N(R8)-SO2-R13, where R8 has the abovementioned meaning and R13 is -(C1-C6)-alkyl or -(C0-C6)-alkyl-(C6-C14)-aryl, 4.28) -(C0-C4)-alkyl-S(O)2-N(R8)-(C0-C6)-alkyl-(C6-C14)-aryl, in which aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m) and R8 has the abovementioned meaning, 4.29) -(C0-C4)-alkyl-S(O)2-N(R8)-(C0-C6)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m) and R8 has the abovementioned meaning, 4.30) ~-(C0-C4)-alkyl-S(O)2-N(R8)-(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m) and R8 has the abovementioned meaning, 4.31) ~-(CO-C4)-alkyl-S(O)2-(C0-C6)-alkyl-(C6-C14)-aryl, in which aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.32) ~-(C0-C4)-alkyl-S(O)2-(C0-C6)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.33) ~-O-(C0-C6)-alkyl-Het, in which Het is~
unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.34) ~-(C0-C4)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), or
5. -C(O)-N(R8)-(C0-C6)-alkyl-(C6-C14)-aryl in which aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals 4.1) to 4.35) or 4.4) a) to 4.4) m) and R8 has the abovementioned meaning,
6. -C(O)-N(R8)-(C0-C6)-alkyl-Het in which Het has the abovementioned meaning and is unsubstituted or~
substituted, once, twice or three times, independently of each other, by the abovementioned radicals 4.1) to 4.35) or 4.4)a) to 4.4)m) and R8 has the abovementioned meaning, or
7. ~-NH-(C6-C14)-aryl in which aryl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals 4.1) to 4.35) or 4.4) a) to 4.4) m), or
8. ~-NH-Het in which Het has the abovementioned meaning and is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals 4.1) to 4.35) or 4.4) a) to 4.4) m), R3, R4, R5, R6 and R7 are identical or different and are, independently of each other, 1. ~hydrogen atom, 2. ~halogen, 3. ~-(C1-C6)-alkyl in which alkyl is unsubstituted or substituted, once, twice or three times, by halogen, 4. ~-O-(C1-C6)-alkyl in which alkyl is unsubstituted or~
substituted, once, twice or three times, by halogen, or 5. ~-S-(C1-C6)-alkyl, or R4 and R5 or R5 and R6 form, together with the carbon atoms to which they are in each case bonded, independently of each other, a 5- or 6-membered ring which is aromatic or saturated and contains zero, one or two heteroatoms from the series oxygen, nitrogen or sulfur, where the ring is unsubstituted or is substituted, at one or at several carbon atoms, once or twice, by halogen and the other radicals R3, R6 and R7 or R3, R4 and R7 have the abovementioned meaning of 1. to 5.
or for the case b) R1 ~is hydrogen atom or -(C1-C6)-alkyl, R2 ~is -(C1-C6)-alkyl, where alkyl is substituted, once, twice or three times, by 1. ~-C(O)-O-R8', in which R8' is 1.1) hydrogen atom or 1.2) -(C1-C6)-alkyl, 2. ~-(C1-C6)-alkyl-O-R8', in which R8' has the abovementioned meaning, 3. ~-(C6-C14)-aryl in which aryl is substituted, once, twice or three times, independently of each other, by 3.1) ~-(C2-C6)-alkyl-C(O)-O-R8' in which R8' has the abovementioned meaning, 3.2) ~-O-(C1-C6)-alkyl-C(O)-O-R8' in which R8' has the abovementioned meaning, 3.3) ~-N(R14)-(R15) in which R14 and R15 form, together with the nitrogen atom to which they are bonded, a 5-, 6- or 7-membered saturated ring, where a heteroatom from the series oxygen, sulfur and nitrogen can also replace one or two further carbon atoms and, in the case of nitrogen, the nitrogen atoms can, independently of each other, be unsubstituted or substituted by (C1-C6)-alkyl, 3.4) ~-(CH2)k-N(R9')-(R10') in which k is 2, 3, 4 or 5 and R9' and R10' are identical or different and are, independently of each other, 3.4.1) hydrogen or 3.4.2) -(C1-C6)-alkyl, or R9' and R10' form, together with the nitrogen atom to which they are bonded, a 5-, 6- or 7-membered saturated ring, where a heteroatom from the series~
oxygen, sulfur and nitrogen can also replace one or two further carbon atoms and, in the case of nitrogen, the nitrogen atoms can, independently of each other, be unsubstituted or substituted by (C1-C6)-alkyl, 3.5) ~-O-(C2-C6)-alkyl-N(R9')-R10', where R9' and R10' have the abovementioned meaning, 3.6) ~-N(R8')-C(O)-(C1-C6)-alkyl in which alkyl is unsubstituted or substituted, once, twice or three times, by 3.6.1) halogen, 3.6.2) cyano, 3.6.3) nitro 3.6.4) hydroxyl, 3.6.5) amino, 3.6.6) -C(O)-O-(C1-C6)-alkyl, or 3.6.7) -C(O)-OH, and R8' has the abovementioned meaning, 3.7) -phenyl, where the phenyl ring is unsubstituted or substituted, once, twice or three times, by 3.7.1) halogen, 3.7.2) -(C1-C6)-alkyl, 3.7.3) -O-(C1-C6)-alkyl, 3.7.4) -S(O)2-R16', where R16' is (C1-C6)-alkyl or -NH2, 4.~Het, where Het is a saturated or unsaturated monocyclic or bicyclic, 3- to 10-membered heterocyclic ring system which contains 1,2 or 3 identical or different ring heteroatoms from the series nitrogen, oxygen and sulfur and is unsubstituted or substituted, once, twice or three times, by 4.1) halogen, 4.2) cyano, 4.3) nitro, 4.4) hydroxyl, 4.5) amino, 4.6) -C(O)-O(C1-C6)-alkyl, 4.7) -C(O)-OH, 4.8) -(C1-C6)-alkyl, where alkyl is unsubstituted or substituted, once, twice or three times, by halogen, 4.9) -O-(C1-C6)-alkyl, where alkyl is unsubstituted or substituted, once, twice or three times, by halogen, 4.10) pyridyl, or 4.11) phenyl, where phenyl is unsubstituted or substituted, once or more than once and independently of each other, by a radical from the series halogen, -(C1-C6)-alkoxy and -(C1-C6)-alkyl, and R4 and R5 or R5 and R6 form, together with the carbon atoms to which they are in each case bonded, independently of each other, a 5- or 6-membered ring which is saturated and contains one or two heteroatoms from the series oxygen, nitrogen or sulfur, where the ring is unsubstituted or substituted, at one or at several carbon atoms, once or twice, by halogen, and the other radicals R3, R6 and R7 or R3, R4 and R7 are hydrogen, with the proviso that the unsubstituted benzo[1,3]dioxole ring is excluded.

2. ~A compound of the formula I as claimed in claim 1, wherein for the case a) R1 ~is hydrogen atom or -(C1-C6)-alkyl, R2 ~is -(C1-C6)-alkyl, where alkyl is substituted, once, twice or three times, by 1. ~-(C1-C6)-alkyl-O-(C6-C14)-aryl, 2. ~-(C0-C6)-alkyl-N(R8)-C(O)-O-(C1-C6)-alkyl, in which R8 is i) ~hydrogen atom ii) ~-(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by -NH2, -CN, -OH, -C(O)-OH, -C(O)-O-(C1-C6)-alkyl, -C(O)-NH-OH, NO2 or halogen or iii) ~-OH, 3. ~-C(O)-N(R9)-(R10), in which R9 and R10 are identical or different and are, independently of each other, i) hydrogen atom or ii) -(C1-C6)-alkyl, or R9 and R10 form, together with the nitrogen atom to which they are bonded, a 5-, 6- or 7-membered saturated ring, where a heteroatom from the series oxygen, sulfur and nitrogen can also replace one or two further carbon atoms and, in the case of nitrogen, the nitrogen atoms can, independently of each other, be unsubstituted or substituted by (C1-C6)-alkyl, 4. phenyl, in which phenyl is substituted, once, twice or three times, independently of each other, by 4.1) -(C0-C4)-alkyl-Het, in which Het is defined as below and is unsubstituted or substituted, once, twice or three times, independently of each other, by the radicals a) to m) mentioned below, 4.2) -(C0-C6)-alkyl-C(O)-N(R9)-(R10), in which R9 and R10 have the abovementioned meaning, 4.3) -(C0-C6)-alkyl-C(O)-NH-CN, 4.4) -(C0-C6)-alkyl-C(O)-(C0-C6)-alkyl-Het, where Het is a radical from the group: azepine, azetidine, aziridine, benzimidazoie, benzofuran, benzo[1,4]dioxin, 1,3-benzodioxole, 4H-benzo[1,4]oxazine, benzoxazole, benzothiazole, benzothiophene, quinazoline, quinoline, quinoxaline, chroman, cinnoline, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, 1,4-dioxin, dioxole, furan, imidazole, indazole, indole, isoquinoline, isochroman, isoindole, isothiazole, isoxazole, morpholine, 1,2-oxazine, 1,3-oxazine, 1,4-oxazine, oxazole, oxiran, piperazine, piperidine, phthalazine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyridoimidazole, pyridopyridine, pyrido-pyrimidine, pyrrole, pyrrolidine, tetrazole, 1,2-thiazine, 1,3-thiazine, 1,4-thiazine, thiazole, thiomorpholine, thiophene, thiopyran, 1,2,3-triazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazole or 1,2,4-triazole, and in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by a) halogen, b) cyano, c) nitro, d) hydroxyl, e) amino, f) -C(O)-O-(C1-C6)-alkyl, g) -C(O)-OH, h) -(C1-C6)-alkyl, where alkyl is unsubstituted or substituted, once, twice or three times, by halogen, i) -O-(C1-C6)-alkyl, where alkyl is unsubstituted or substituted, once, twice or three times, by halogen, or -N(R9)-(R10), j) =O, k) -Het, in which Het is defined as above, l) -(C2-C6)-alkenyl, where alkenyl is unsubstituted or substituted, once, twice or three times, by halogen, or -N(R9)-(R10), or m) -(C2-C6)-alkynyl, where alkynyl is unsubstituted or substituted, once, twice or three times, by halogen or -N(R9)-(R10), 4.5) -(C0-C6)-alkyl-C(O)-(C0-C6)-alkyl-OH, 4.6) -O-(C0-C6)-alkyl-C(O)-N(R9)-(R10), in which R9 and R10 have the abovementioned meaning, 4.7) -(C0-C6)-alkyl-C(O)-N(R8)-(C0-C6)-alkyl-N(R9)-(R10), in which R8, R9 and R10 have the abovementioned meaning, 4.8) -(C0-C4)-alkyl-N(R8)-S(O)2-(C0-C6)-alkyl-Het, in which Het is defined as above and is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m) and R8 has the abovementioned meaning, 4.9) -(C0-C4)-alkyl-S(O)2-(C0-C6)-alkyl-(C6-C14)-phenyl, in which phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.10) -(C0-C6)-alkyl-C(O)-N(R8)-(CO-C6)-alkyl-Het, where R8 has the abovementioned meaning and Het has the abovementioned meaning and is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.11) -(C0-C6)-alkyl-C(O)-N(R8)-(C0-C6)-alkyl-(C6-C14)-phenyl, where phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.12) -(C1-C6)-alkyl-N(R9)-(R10), in which R9 and R10 have the abovementioned meaning, 4.13) -(CH2)y-N(R8)-C(O)-(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m) and y is 1 or 2, 4.14) -(C0-C4)-alkyl-N(R8)-C(O)-(C0-C6)-alkyl-(C6-C14)-phenyl, in which phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.15) -(C0-C4)-alkyl-N(R8)-C(O)-(C0-C6)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.16) -(C0-C4)-alkyl-N(R8)-C(O)-O-(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.17) -(C0-C4)-alkyl-N(R8)-C(O)-O-(C1-C6)-alkenyl, in which alkenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.18) -(C0-C4)-alkyl-N(R8)-C(O)-O-(C1-C6)-alkynyl, in which alkynyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.19) -(C0-C4)-alkyl-N(R8)-C(O)-O-(C0-C6)-alkyl-(C6-C14)-phenyl, in which phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.20) -(C0-C4)-alkyl-N(R8)-C(O)-O-(C0-C6)-alkyl-Het, in which Het is defined as above and is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21) -(C0-C4)-alkyl-N(R8)-C(O)-(C0-C6)-alkyl-N(R11)-R12, in which R8 has the abovementioned meaning and R11 and R12 are identical or different and are, independently of each other, 4.21.1) a hydrogen atom, 4.21.2) -(C1-C6)-alkyl, 4.21.3) -(C0-C6)-alkyl-(C6-C14)-phenyl, in which phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.4) -(C0-C6)-alkyl-Het, in which Het is defined as above and is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.5) -C(O)-(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.6) -C(O)-(C3-C6)-cycloalkyl, in which cycloalkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.7) -C(O)-(C0-C6)-alkyl-(C6-C14)-phenyl, in which phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.8) -C(O)-(C0-C6)-alkyl-Het, in which Het is defined as above and is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.9) -SO2-(C0-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.10) -NH-SO2-(C0-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.11) -SO2-(C0-C6)-alkyl-(C6-C14)-phenyl-(C0-C6)-alkyl, in which phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 4.21.12) -SO2-(C0-C6)-alkyl-Het, in which Het is defined as above and is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), or 4.22) -O-(C0-C6)-alkyl-Het, in which Het is defined as above and is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to m), 5. -C(O)-N(R8)-(C0-C6)-alkyl-phenyl, in which phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals 4.1) to 4.23) or 4.4) a) to 4.4) m) and R8 has the abovementioned meaning, or 6. -C(O)-N(R8)-(C0-C6)-alkyl-Het, in which Het is azepine, azetidine, aziridine, benzimidazole, benzofuran, benzo[1,4]dioxin, 1,3-benzodioxole, 4H-benzo[1,4]oxazine, benzoxazole, benzothiazole, benzothiophene, quinazoline, quinoline, quinoxaline, chroman, cinnoline, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, 1,4-dioxin, dioxole, furan, imidazole, indazole, indole, isoquinoline, isochroman, isoindole, isothiazole, isoxazole, morpholine, 1,2-oxazine, 1,3-oxazine, 1,4-oxazine, oxazole, oxirane, piperazine, piperidine, phthalazine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyridoimidazole, pyridopyridine, pyridopyrimidine, pyrrole, pyrrolidine, tetrazole, 1,2-thiazine, 1,3-thiazine, 1,4-thiazine, thiazole, thiomorpholine, thiophene, thiopyran, 1,2,3-triazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazole or 1,2,4-triazole, and Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals 4.1) to 4.4) or 4.4) a) to 4.4) m) and R8 has the abovementioned meaning, R3, R4, R5, R6 and R7 are identical or different and are, independently of each other, 1. hydrogen atom, 2. halogen, 3. -(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, by halogen, or 4. -O-(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, by halogen, or R4 and R5 or R5 and R6 form, together with the carbon atoms to which they are in each case bonded, independently of each other, a dioxane, dioxole, dihydrofuran or furan ring, where the ring is unsubstituted or substituted, at one or at several carbon atoms, once or twice, by halogen and the other radicals R3, R6 and R7 or R3, R4 and R7 have the abovementioned meaning of 1. to 4., or for the case b) R1 is hydrogen atom or -(C1-C4)-alkyl, R2 is -(C1-C4)-alkyl, where alkyl is substituted, once, twice or three times, by 1. -C(O)-O-R8', in which R8' is 1.1) hydrogen atom or 1.2) -(C1-C4)-alkyl, 2. -(C1-C4)-alkyl-O-R8', in which R8' has the abovementioned meaning, 3. phenyl, in which phenyl is substituted, once, twice or three times, independently of each other, by 3.1) -(C2-C4)-alkyl-C(O)-O-R8', in which R8' has the abovementioned meaning, 3.2) -O-(C1-C4)-alkyl-C(O)-O-R8', in which R8' has the abovementioned meaning, 3.3) -N(R14)-(R15) in which R14 and R15 form, together with the nitrogen atom to which they are bonded, a radical which can be derived from pyrrolidine, piperidine, pyrazolidine, pyrazine, tetrazine, imidazolidine, piperazine, isoxazolidine, morpholine, isothiazolidine or thiomorpholine, and, in the case of nitrogen, the nitrogen atoms can, independently of each other, be unsubstituted or substituted by (C1-C4)-alkyl, 3.4) -(CH2)k-N(R9')-(R10') in which k is 2, 3, 4 or 5 and R9' and R10' are identical or different and are, independently of each other, 3.4.1) hydrogen atom or 3.4.2) -(C1-C6)-alkyl, or R9' and R10' form, together with a nitrogen atom to which they are bonded, a radical which can be derived from pyrrolidine, piperidine, pyrazolidine, pyrazine, tetrazine, imidazolidine, piperazine, isoxazolidine, morpholine, isothiazolidine or thiomorpholine, and, in the case of nitrogen, the nitrogen atoms can, independently of each other, be unsubstituted or substituted by (C1-C4)-alkyl, 3.5) -O-(C2-C6)-alkyl-N(R9')-R10', where R9' and R10' have the abovementioned meaning, 3.6) -N(R8')-C(O)-(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, by 3.6.1) halogen, 3.6.2) cyano, 3.6.3) nitro 3.6.4) hydroxyl, 3.6.5) amino, 3.6.7) -C(O)-O-(C1-C6)-alkyl, or 3.6.8) -C(O)-OH, and R8' has the abovementioned meaning, 3.7) -phenyl, where the phenyl ring is unsubstituted or substituted, once, twice or three times, by 3.7.1) halogen, 3.7.2) -(C1-C6)-alkyl, 3.7.3) -O-(C1-C6)-alkyl, or 3.7.4) -S(O)2-R16', where R16' is (C1-C6)-alkyl or -NH2, 4. Het, where Het is azepine, azetidine, aziridine, benzimidazole, benzofuran, benzo[1,4]dioxin, 1,3-benzodioxole, 4H-benzo[1,4]oxazine, benzoxazole, benzothiazole, benzothiophene, quinazoline, quinoline, quinoxaline, chroman, cinnoline, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, 1,4-dioxin, dioxole, furan, imidazole, indazole, indole, isoquinoline, isochroman, isoindole, isothiazole, isoxazole, morpholine, 1,2-oxazine, 1,3-oxazine, 1,4-oxazine, oxazole, oxirane, piperazine, piperidine, phthalazine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyridoimidazole, pyridopyridine, pyridopyrimidine, pyrrole, pyrrolidine, tetrazole, 1,2-thiazine, 1,3-thiazine, 1,4-thiazine, thiazole, thiomorpholine, thiophene, thiopyran, 1,2,3-triazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazole or 1,2,4-triazole, and Het is unsubstituted or substituted, once, twice or three times, independently of each other, by 4.1) halogen, 4.2) cyano, 4.3) nitro, 4.4) hydroxyl, 4.5) amino, 4.6) -C(O)-O(C1-C6)-alkyl, 4.7) -C(O)-OH, 4.8) -(C1-C6)-alkyl, where alkyl is unsubstituted or substituted, once, twice or three times, by halogen, 4.9) -O-(C1-C6)-alkyl, where alkyl is unsubstituted or substituted, once, twice or three times, by halogen, 4.10) pyridyl, or 4.11) phenyl, where phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by a radical from the series halogen, -(C1-C6)-alkoxy and -(C1-C6)-alkyl, and R4 and R5 or R5 and R6 form, together with the phenyl ring and the carbon atoms to which they are in each case bonded, independently of each other, a ring system from the series benzo[1,4]dioxane, 2,3-dihydrobenzofuran and 2,2-difluorobenzo[1,3]dioxole, and the other radicals R3, R6 and R7 or R3, R4 and R7 are hydrogen atom.

3. A compound of the formula I as claimed in claim 1 or 2, wherein for the case a), R1 is hydrogen atom, R2 is -(C1-C3)-alkyl, where alkyl is substituted by 1. phenyl, in which phenyl is substituted, once, twice or three times, independently of each other, by 1.1) -(C0-C6)-alkyl-C(O)-N(R9)-(R10), in which R9 and R10 are hydrogen atom, methyl, ethyl, propyl or butyl, or R9 and R10 form, together with the nitrogen atom to which they are bonded, a radical which can be derived from pyrrolidine, piperidine, pyrazolidine, pyrazine, tetrazine, imidazolidine, piperazine, isoxazolidine, morpholine, isothiazolidine or thiomorpholine, and, in the case of nitrogen, the nitrogen atoms can, independently of each other, be unsubstituted or substituted by (C1-C4)-alkyl, 1.2) -(C0-C4)-alkyl-C(O)-NH-CN, 1.3) -O-(C0-C6)-alkyl-C(O)-N(R9)-(R10), in which R9 and R10 have the meaning mentioned above under 1.1), 1.4) -(C0-C6)-alkyl-C(O)-N(R8)-(C0-C6)-alkyl-N(R9)-(R10), in which R8 is hydrogen, methyl, ethyl, propyl or butyl, R9 and R10 have the abovementioned meaning, 1.5) -C(O)-N(R8)-(C0-C2)-alkyl-Het, where R8 has the abovementioned meaning and Het is azepine, azetidine, aziridine, benzimidazole, benzofuran, benzo[1,4]dioxin, 1,3-benzodioxole, 4H-benzo[1,4]oxazine, benzoxazole, benzothiazole, benzothiophene, quinazoline, quinoline, quinoxaline, chroman, cinnoline, 1,2-diazepine, 1,3-diazepine, 1,4-diazepine, 1,4-dioxin, dioxole, furan, imidazole, indazole, indole, isoquinoline, isochroman, isoindole, isothiazole, isoxazole, morpholine, 1,2-oxazine, 1,3-oxazine, 1,4-oxazine, oxazole, oxirane, piperazine, piperidine, phthalazine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyridoimidazole, pyridopyridine, pyridopyrimidine, pyrrole, pyrrolidine, tetrazole, 1,2-thiazine, 1,3-thiazine, 1,4-thiazine, thiazole, thiomorpholine, thiophene, thiopyran, 1,2,3-triazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazole or 1,2,4-triazole, and Het is unsubstituted or substituted, once, twice or three times, independently of each other, by a) halogen b) cyano, c) nitro, d) hydroxyl, e) amino, f) -C(O)-O-(C1-C4)-alkyl, g) -C(O)-OH, h) -(C1-C4)-alkyl, where alkyl is unsubstituted or substituted, once, twice or three times, by halogen, i) -O-(C1-C4)-alkyl, where alkyl is unsubstituted or substituted, once, twice or three times, by halogen, or 1.6) -C(O)-N(R8)-(C0-C4)-alkyl-phenyl, where phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to i), 1.7) -CH2-N(R9)-(R10), in which R9 and R10 have the abovementioned meaning, 1.8) -(CH2)y-N(R8)-C(O)-(C1-C4)-alkyl in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to i), and y is 1 or 2, 1.9) -(CH2)x-N(R8)-C(O)-(C0-C2)-alkyl-phenyl, in which phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to i), and x is 0, 1 or 2, 1.10) -(CH2)x-N(R8)-C(O)-(C0-C2)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to i), and x is 0, 1 or 2, 1.11) -(CH2)x-N(R8)-C(O)-O-(C1-C4)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to i), and x is 0, 1 or 2, 1.12) -(CH2)x-N(R8)-C(O)-O-(C0-C4)-alkyl-phenyl, in which phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to i), and x is 0, 1 or 2, 1.13) -(CH2)x-N(R8)-C(O)-O-(C0-C4)-alkyl-Het in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to i), and x is 0, 1 or 2, 1.14) -(CH2)x-N(R8)-C(O)-N(R11)-R12, in which R8 and x have the abovementioned meaning and R11 and R12 are identical or different and are, independently of each other, 1.14.1) hydrogen atom, 1.14.2) methyl, ethyl, propyl or butyl, 1.14.3) -(C0-C2)-alkyl-phenyl, in which phenyl is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to i), 1.14.4)-(C0-C2)-alkyl-Het, in which Het is unsubstituted or substituted, once, twice or three times, independently of each other, by the abovementioned radicals a) to i), 1.14.5) -C(O)-(C1-C4)-alkyl, 1.14.6) -C(O)-(C0-C2)-alkyl-phenyl, 1.14.7) -C(O)-(C0-C2)-alkyl-Het, 1.14.8) -SO2-(C1-C4)-alkyl, 1.14.9) -SO2-(C0-C4)-alkyl-phenyl, or 1.14.10) -SO2-(C0-C2)-alkyl-Het, R3, R4, R5, R6 and R7 are identical or different and are, independently of each other, 1. hydrogen atom, 2. halogen, 3. -(C1-C6)-alkyl, in which alkyl is unsubstituted or substituted, once, twice or three times, by halogen, 4. -O-(C1-C6)-alkyl in which alkyl is unsubstituted or substituted, once, twice or three times, by halogen, or R4 and R5 or R5 and R6 form, together with the carbon atoms to which they are bonded, independently of each other, a dioxane, dioxole, dihydrofuran or furan ring and the other radicals R3, R6 and R7 or R3, R4 and R7 have the abovementioned meaning of 1. to 4., or, for the case b), R1 is hydrogen atom, R2 is -(C1-C2)-alkyl, where alkyl is substituted, once, twice or three times, by 1. -C(O)-O-R8', in which R8' is 1.1) hydrogen atom or 1.2) -(C1-C2)-alkyl, 2. phenyl, in which phenyl is substituted, once, twice or three times, independently of each other, by 2.1) -O-(C2-C4)-alkyl-N(R9')-R10', where R9' and R10' are, independently of each other, hydrogen atom, methyl or ethyl, or R9' and R10' form, together with the nitrogen atom to which they are bonded, a radical which can be derived from pyrrolidine, piperidine, piperazine, morpholine or thiomorpholine, and, in the case of piperazine, the second nitrogen atom can be substituted by methyl or ethyl, 2.2) -O-(C1-C2)-alkyl-C(O)-O-R8', in which R8' is, independently of each other, hydrogen atom, methyl or ethyl, or 2.3) -N(R14)-(R15) in which R14 and R15 form, together with the nitrogen atom to which they are bonded, a radical which can be derived from pyrrolidine, piperidine, pyrazolidine, pyrazine, tetrazine, imidazolidine, piperazine, isoxazolidine, morpholine, isothiazolidine or thiomorpholine, and, in the case of nitrogen, the nitrogen atoms can, independently of each other, be unsubstituted or substituted by methyl or ethyl, 2.4) -(CH2)k-N(R9')-(R10') in which k is 2, 3 or 4 and R9' and R10' are identical or different and are, independently of each other, hydrogen atom, methyl or ethyl, or R9' and R10' form, together with the nitrogen atom to which they are bonded, a radical which can be derived from pyrrolidine, piperidine, piperazine, morpholine or thiomorpholine, and, in the case of piperazine, the second nitrogen atom can be substituted by methyl or ethyl, and R4 and R5 or R5 and R6 form, together with the phenyl ring and the carbon atoms to which they are in each case bonded, independently of each other, a ring system from the series benzo[1,4]dioxane, 2,3-dihydrobenzofuran and 2,2-difluorobenzo[1,3]dioxole, and the other radicals R3, R6 and R7 or R3, R4 and R7 are hydrogen atom.

4. A compound of the formula I as claimed in one or more of claims 1 to 3, wherein one of the following compounds is selected pyrimidine-4,6-carboxylic acid 4-(3-methoxybenzylamide) 6-(4-propylcarbamoyl benzylamide), pyrimidine-4,6-carboxylic acid 4-(4-isopropylcarbamoylbenzylamide) 6-(3-methoxybenzylamide), [4-({[6-(3-methoxybenzylcarbamoyl)pyrimidine-4-carbonyl]amino}-methyl)phenyl]carboxyamino isopropyl ester, pyrimidine-4,6-carboxylic acid 4-(3-methoxybenzylamide) 6-[(2-phenoxyethyl)amide], (5-{[6-(3-methoxybenzylcarbamoyl)pyrimidine-4-carbonyl)amino}-pentyl)carboxyamino methyl ester, pyrimidine-4,6-carboxylic acid 4-[4-(2-dimethylaminoethyl-carbamoyl)benzylamide] 6-(3-methoxybenzylamide), pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)amide] 6-[4-(2-dimethylaminoethylcarbamoyl)-benzylamide], pyrimidine-4,6-carboxylic acid 4-(3-chloro-4-fluorobenzylamide) 6-[4-(2-dimethylaminoethytcarbamoyl)benzylamide], pyrimidine-4,6-carboxylic acid 4-dimethylcarbamoylmethylamide 6-(3-methoxybenzylamide), [4-({[6-(3-aminobenzylcarbamoyl)pyrimidine-4-carbonyl]amino}-methyl)phenyl]carboxyamino tert-butyl ester, pyrimidine-4,6-dicarboxylic acid 4-(3-chlorobenzylamide) 6-(4-fluoro-3-methylbenzylamide), pyrimidine-4,6-dicarboxylic acid 4-[(2-chloropyridin-4-ylmethyl)-amide] 6-(4-fluoro-3-methylbenzylamide), pyrimidine-4,6-dicarboxylic acid 4-benzylamide 6-(4-fluoro-3-methyl-benzylamide), pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[(pyridin-4-ylmethyl)amide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-(pyridin-3-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-{4-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]benzylamide}, pyrimidine-4,6-carboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4(2-morpholin-4-yl-2-oxoethoxy)benzylamide], pyrimidine-4,6-carboxylic acid 4-(4-diethylcarbamoylmethoxy-benzylamide) 6-(4-fluoro-3-methylbenzylamide), pyrimidine-4,6-carboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(isopropylcarbamoylmethyl)benzylamide], pyrimidine-4,6-carboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-{4-[(2-morpholin-4-ylethylcarbamoyl)methyl]benzylamide}, pyrimidine-4,6-carboxylic acid 4-(4-diethylcarbamoylmethyl-benzylamide) 6-(4-fluoro-3-methylbenzylamide), pyrimidine-4,6-carboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(2-morpholin-4-yl-2-oxoethyl)benzylamide], pyrimidine-4,6-carboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(isopropylcarbamoylmethoxy)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[(pyridin-3-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-(3-methoxybenzylamide) 6-({[(pyridin-4-ylmethyl)carbamoyl]methyl}amide), pyrimidine-4,6-carboxylic acid 4-({[(2-chloropyridin-4-ylmethyl)-carbamoyl]methyl}amide) 6-(3-methoxybenzylamide), pyrimidine-4,6-carboxylic acid 4-(3-chloro-4-fluorobenzylamide) 6-({[(2-chloropyridin-4-ylmethyl)carbamoyl]methyl}amide), [4-({[6-(3-methoxybenzylcarbamoyl)pyrimidine-4-carbonyl]amino}methyl)phenyl]carboxyamino isobutyl ester, [4-({[6-(3-methoxybenzylcarbamoyl)pyrimidine-4-carbonyl]amino}-methyl)phenyl]carboxyamino ethyl ester, [4-({[6-(3-methoxybenzylcarbamoyl)pyrimidine-4-carbonyl]amino}-methyl)phenyl]carboxyamino allyl ester, pyrimidine-4,6-carboxylic acid 4-(3-chloro-4-fluorobenzylamide) 6-(4-(1-methylpiperidin-3-yloxy)benzylamide], pyrimidine-4,6-carboxylic acid 4-(3-chloro-4-fluorobenzylamide) 6-({[(pyridin-3-ylmethyl)carbamoyl]methyl}amide), pyrimidine-4,6-carboxylic acid 4-(3-methoxybenzylamide) 6-[4-(2-morpholin-4-ylethylcarbamoyl)benzylamide), pyrimidine-4,6-carboxylic acid 4-(3-methoxybenzylamide) 6-[4-(2-pyrrolidin-1-yl-ethylcarbamoyl)benzylamide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)amide] 6-[(2'-sulfamoylbiphenyl-2-ylmethyl)amide];
pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(thiophen-2-ylmethyl)amide), pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide) 6-[(5-methylfuran-2-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(5-methylfuran-2-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(5-pyridin-2-ylthiophen-2-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(pyridin-3-ylmethyl)amide];
pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)amide] 6-[(pyridin-3-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)amide] 6-[(5-methylfuran-2-ylmethyl)amide), pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)amide] 6-[(thiophen-2-ylmethyl)amide);
pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(5-methylisoxazol-3-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide) 6-[(1-methyl-1H-pyrazol-4-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(2,5-dimethylfuran-3-ylmethyl)amide];
pyrimidine-4,6-carboxylic acid 4-[(6-aminopyridin-3-ylmethyl)amide]
6-[(2,3-dihydrobenzofuran-5-ylmethyl)amide];
pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(1-methyl-1H-pyrrol-2-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-[(1H-benzoimidazol-2-ylmethyl)amide] 6-[(2,3-dihydrobenzofuran-5-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(pyrazin-2-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-[(2,2-difluorobenzo[1,3]dioxol-5-ylmethyl)amide] 6-[(pyridin-4-ylmethyl)amide], ({6-[(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)carbamoyl]pyrimidine-4-carbonyl}amino)acetic acid methyl ester, pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(2-methyl-1H-imidazol-4-ylmethyl)amide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(2-pyridin-2-ylethyl)amide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-{[3-(4-fluorophenyl)-1H-pyrazol-4-ylmethyl]-amide};
pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)amide] 6-[4-(3-dimethylaminopropoxy)benzylamide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)amide] 6-[4-(2-dimethylaminoethoxy)benzylamide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzo[1,4]dioxin-6-ylmethyl)amide] 6-[3-(2-dimethylaminoethoxy)benzylamide], pyrimidine-4,6-carboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(pyridin-4-ylmethyl)amide], pyrimidine-4,6-dicarboxylic acid 4-(3-chloro-4-fluorobenzylamide) 6-(4-[3'-methylsulfonyl]ureidobenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(4-oxopiperidine-1-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(4-oxopiperidine-1-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(4-oxopiperidine-1-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-[4-(4-hydroxypiperidine-1-carbonyl)benzylamide] 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(4-hydroxypiperidine-1-carbonyl)benzyl-amide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(4-hydroxypiperidine-1-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(thiomorpholine-4-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(thiomorpholine-4-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(thiomorpholine-4-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(3-oxopiperazine-1-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(3-oxopiperazine-1-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(3-oxopiperazine-1-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(2-hydroxyethylcarbamoyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(2-hydroxyethylcarbamoyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-{4-[(pyridin-4-ylmethyl)carbamoyl]benzylamide}, pyrimidine-4,6-dicarboxylic acid 4-(4-cyanocarbamoylbenzylamide) 6-(4-fluoro-3-methylbenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(3-morpholin-4-ylpropylcarbamoyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(3-morpholin-4-yl-propylcarbamoyl)-benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(4-methylpiperazine-1-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-{4-[(pyridin-4-ylmethyl)carbamoyl]benzylamide}, pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-(4-[3'-methylsulfonyl]ureidobenzylamide), pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-(4-[3-methylsulfonyl]ureidobenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(4-N-cyanocarbamoyl-benzylamide) 6-[(2,3-dihydrobenzofuran-5-ylmethyl)amide], pyrimidine-4,6-dicarboxylic acid 4-(4-N-cyanocarbamoyl-benzylamide) 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(morpholine-4-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-(3-[3'-methylsulfonyl]ureidobenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(4-hydroxycarbamoylbenzylamide) 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(hydroxycarbamoylmethylcarbamoyl)-benzylamide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(1-methylpiperidin-3-yloxy)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(2-piperazin-1-ylethylcarbamoyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-(4-hydroxycarbamoylbenzylamide), pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-(4-hydroxycarbamoylbenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(1-methylpiperidin-3-yloxy)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-tert-butylcarbamoylbenzyl-amide) 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-{4-[methyl-(1-methylpiperidin-4-yl)carbamoyl)benzylamide}, {4-[({6-[(2,3-dihydrobenzofuran-5-ylmethyl)carbamoyl]pyrimidine-4-carbonyl}amino)methyl]benzoylamino}acetic acid, pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(2-pyrrolidin-1-yl-ethylcarbamoyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-{4-[4-(2-dimethylaminoethyl)-piperazine-1-carbonyl]benzylamide} 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-(4-[3'-methylsulfonyl]ureidobenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[3-(2-morpholin-4-ylethylcarbamoyl)benzylamide], [4-({[6-(4-fluoro-3-methylbenzylcarbamoyl)pyrimidin-4-carbonyl]-amino}-methyl)benzoylamino]acetic acid, pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(2-piperazin-1-ylacetylamino)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(2-morpholin-4-yl-ethylcarbamoyl)benzylamide], [4-({[6-(4-fluoro-3-methylbenzylcarbamoyl)pyrimidin-4-carbonyl]-amino}methyl)benzoylamino]acetic acid methyl ester, pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[3-(morpholine-4-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-{4-[(piperidin-4-ylmethyl)carbamoyl]benzylamide}, pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(piperidin-4-ylcarbamoyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[4-(piperidin-4-ylcarbamoyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-{4-[methyl-(1-methylpiperidin-4-yl)carbamoyl]benzylamide}, pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-[(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-7-ylmethyl)amide], pyrimidine-4,6-dicarboxylic acid 4-(4-fluoro-3-methylbenzylamide) 6-{4-[(piperidin-4-ylmethyl)carbamoyl]benzylamide}, pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(4-methyl-piperazine-1-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(4-pyridin-4-ylpiperazine-1-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(2-morpholin-4-ylacetylamino)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(morpholine-4-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-(4-[p-toluenesulfonyl]ureidobenzylamide), pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)-amide] 6-[4-(4-methylpiperazine-1-carbonyl)benzyl-amide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(2-pyrrolidin-1-yl-ethylcarbamoyl)benzyl-amide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-(4-[3'-phenylsulfonyl]ureidobenzylamide), pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(2-morpholin-4-yl-ethylcarbamoyl)benzyl-amide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(2-pyrrolidin-1-ylethoxy)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-[4-(3-cyclohexanecarbonylureido)-benzylamide] 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-{4-[3-(pyridine-3-carbonyl)ureido]benzylamide}, pyrimidine-4,6-dicarboxylic acid 4-[4-(3-isobutyrylureido)-benzylamide] 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(2-pyrrolidin-1-ylacetylamino)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-[(4-chlorothiophen-2-ylmethyl)amide] 6-[(2,3-dihydrobenzofuran-5-ylmethyl)amide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-{4-[2-(2-oxo-pyrrolidin-1-yl)acetylamino]benzylamide), pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-methyl)amide] 6-[(thiophen-3-ylmethyl)amide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(3-methylthiophen-2-ylmethyl)amide], pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[(5-methylthiophen-2-ylmethyl)amide], pyrimidine-4,6-dicarboxylic acid 4-[4-(2-dimethylaminoacetylamino)-benzylamide] 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-[(2,3-dihydrobenzofuran-5-ylmethyl)amide] 6-[4-(2-morpholin-4-ylethoxy)benzylamide], pyrimidine-4.6-dicarboxylic acid 4-[4-(3-cyclohexylureido)benzyl-amide] 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-{4-[3-(2,6-dichloropyridin-4-yl)ureido]benzylamide} 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-[4-(3-tert-butylureido)benzylamide]
6-(3-methoxybenzylamide), [4-({[6-(3-methoxybenzylcarbamoyl)pyrimidine-4-carbonyl]amino}-methyl)phenyl]carboxyamino but-2-ynyl ester, pyrimidine-4,6-dicarboxylic acid 4-(4-ethanesulfonylaminobenzyl-amide) 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(thiophene-2-sulfonylamino)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(2,2,2-trifluoroethanesulfonylamino)benzylamide], [4-({[6-(3-methoxybenzylcarbamoyl)pyrimidin-4-carbonyl]amino}-methyl)phenyl]carboxyamino methyl ester, [4-({[6-(3-methoxybenzylcarbamoyl)pyrimidine-4-carbonyl]amino}-methyl)phenyl]carboxyamino prop-2-ynyl ester, (4-({[6-(3-methoxybenzylcarbamoyl)pyrimidin-4-carbonyl]amino}-methyl)phenyl]carboxyamino 2-methoxyethyl ester, [4-({[6-(3-methoxybenzylcarbamoyl)pyrimidine-4-carbonyl]amino}-methyl)phenyl]carboxyamino 4-fluorophenyl ester, pyrimidine-4,6-dicarboxylic acid 4-[4-(3-benzoylureido)benzylamide]
6-(3-methoxybenzylamide), [3-({[6-(3-methoxybenzylcarbamoyl)pyrimidine-4-carbonyl]amino}-methyl)phenyl]carboxyamino but-2-ynyl ester, [3-({[6-(3-methoxybenzylcarbamoyl)pyrimidine-4-carbonyl]amino}-methyl)phenyl]carboxyamino prop-2-ynyl ester, [3-({[6-(3-methoxybenzylcarbamoyl)pyrimidine-4-carbonyl]amino}-methyl)phenyl]carboxyamino isopropyl ester, pyrimidine-4,6-dicarboxylic acid 4-(3-chloro-4-fluorobenzylamide) 6-[4-(2-pyrrolidin-1-ylethylcarbamoyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(morpholine-4-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-{4-[(pyridin-4-ylmethyl)carbamoyl]benzylamide}, pyrimidine-4,6-dicarboxylic acid 4-(3-chloro-4-fluorobenzylamide) 6-(4-diethylcarbamoylbenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(3-chloro-4-fluorobenzylamide) 6-[4-(morpholine-4-carbonyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(3-chloro-4-fluorobenzylamide) 6-[4-(2-morpholin-4-ylethylcarbamoyl)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-{4-[2-(2,6-dimethylpiperidin-1-yl)-2-oxo-ethyl]benzylamide} 6-(4-fluoro-3-methylbenzylamide), pyrimidine-4,6-dicarboxylic acid 4-(3-methoxybenzylamide) 6-[4-(1-methylpiperidin-3-yloxy)benzylamide], pyrimidine-4,6-dicarboxylic acid 4-(4-diethylcarbamoylbenzylamide) 6-(3-methoxybenzylamide), pyrimidine-4,6-dicarboxylic acid 4-[(2-chloropyridin-4-ylmethyl)-amide] 6-[(2,3-dihydrobenzofuran-5-ylmethyl)amide]
pyrimidine-4,6-dicarboxylic acid 4-(3-chloro-4-fluorobenzylamide) 6-(4-methanesulfonylaminobenzylamide), or pyrimidine-4,6-dicarboxylic acid 4-(4-methanesulfonylbenzylamide) 6-(3-methoxybenzylamide).
5. A process for preparing the compound of the formula I as claimed in one or more of claims 1 to 4, wherein a compound of the formula II
a) is reacted with a compound of the formula IIIa or IIIb where R1, R2, R3, R4, R5, R6 and R7 have the meanings given in formula I and Y is halogen, hydroxyl or C1-C4-alkoxy or forms, together with the carbonyl group, an active ester or a mixed anhydride, with a compound of the formula I being formed, and the reaction products are converted, where appropriate, into their physiologically tolerated salts, or b) a compound of the formula II is reacted with a compound of the formula IIIa or IIIb to give a compound of the formula IVa or IVb where R1 to R7 have the meanings given in formula I and Y
is halogen, hydroxyl or C1-C4-alkoxy, or forms, together with the carbonyl group, an active ester or a mixed anhydride, and the compound of the formula IVa or IVb is purified, where appropriate, and then converted, with a compound of the formula IIIa or IIIb, into a compound of the formula I.
6. A pharmaceutical, which comprises an effective content of at least one compound of the formula I as claimed in one or more of claims 1 to 4 together with a pharmaceutically suitable and physiologically tolerated carrier substance, additive and/or other active compounds and auxiliary substances.
7. The use of the compound of the formula I as claimed in one or more of claims 1 to 4 for producing a pharmaceutical for the prophylaxis and therapy of diseases in whose course an increase in the activity of matrix metalloproteinase 13 is involved.
8. The use as claimed in claim 7, wherein the diseases in whose course an increase in the activity of matrix metalloproteinase 13 is involved are the degenerative joint diseases such as osteoarthroses, spondyloses and cartilage loss following joint trauma or relatively long joint immobilization following meniscus or patella injuries or ligament rupture. They also include diseases of the connective tissue such as collagenoses, periodontal diseases, wound healing disturbances and chronic diseases of the locomotory apparatus such as inflammatory, immunologically determined or metabolism-determined, acute and chronic arthritides, arthropathies, myalgias and disturbances of bone metabolism or cancer diseases such as breast cancer.
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DE10254092A DE10254092A1 (en) 2002-11-20 2002-11-20 New pyrimidine-4,6-dicarboxamide derivatives, are selective collagenase inhibitors useful e.g. for treating degenerative joint diseases, connective tissue disorders or cancer
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