Claims
- 1. Carboxamide compounds comprised of general formula I
- 2. The carboxamide compounds according to claim 1, wherein group A has the meanings given for Cy in claim 1.
- 3. The carboxamide compounds according to claim 1, wherein
R3 denotes H, C1-6alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-4-alkyl-, C1-3-alkoxy-C2-6-alkyl-, amino-C2-6-alkyl-, C1-3-alkyl-amino-C2-6-alkyl- or di-(C1-3-alkyl)-amino-C2-6-alkyl-, B has one of the meanings given for Cy, while the bond to the group W or optionally directly to the group A is formed via a C atom of the carbocyclic moiety or of the optionally fused-on phenyl or pyridine ring or via an N or C atom of the heterocyclic moiety,
while if k=0 the group B and the group A may be connected to one another via a common C atom forming a spirocyclic ring system or via two common, adjacent atoms forming a fused, bicyclic ring system, R15 denotes H, C1-4-alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl-, phenyl or phenyl-C1-3-alkyl-, R17 has one of the meanings given for R16 or denotes phenyl, phenyl-C1-3-alkyl-, dioxolan-2-yl, C1-3-alkylcarbonyl, hydroxycarbonyl-C1-3-alkyl, C1-3-alkylcarbonylamino-C2-3-alkyl-, C1-3-alkylsulphonyl- or C1-3-alkylsulphonylamino-C2-3-alkyl-, R22 denotes phenyl, phenyl-C1-3-alkoxy-, C1-3-alkoxy, C1-3-alkylthio, carboxy, C1-3-alkylcarbonyl, C1-3-alkoxycarbonyl, aminocarbonyl, C1-3-alkylaminocarbonyl, di-(C1-3-alkyl)-aminocarbonyl, C1-3-alkyl-sulphonyl, C1-3-alkyl-sulphinyl, C1-3-alkyl-sulphonylamino-, amino, C1-3-alkylamino-, di-(C1-3-alkyl)-amino-, phenyl-C1-3—alkylamino- or N—(C1-3-alkyl)-phenyl-C1-3-alkylamino-, acetylamino-, propionylamino-, phenylcarbonyl, phenylcarbonylamino-, phenylcarbonylmethylamino-, hydroxyalkylaminocarbonyl, (4-morpholinyl)carbonyl, (1-pyrrolidinyl)carbonyl, (1-piperidinyl)carbonyl, (hexahydro-1-azepinyl)carbonyl, (4-methyl-1-piperazinyl)carbonyl, methylenedioxy, aminocarbonylamino- or alkylaminocarbonylamino-, while in the groups A, B, W, X, Y, Z, R1 to R9 and R11 to R22 in each case one or more C atoms may be mono- or polysubstituted by F and/or in each case one or two C atoms independently of one another may be monosubstituted by Cl or Br, and the groups A, W, X, Y, Z, R1, R2, R4 to R9, R11 to R14, R16 and R18 to R21 and k have the meanings according to claim 1, and the H atom of any carboxy group present or an H atom bound to an N atom in each case by a group which can be cleaved in vivo may be replaced, the tautomers, diastereomers, enantiomers, mixtures thereof and the salts thereof.
- 4. Carboxamide compounds according to claim 3, wherein group A has the meanings given for Cy in claim 3.
- 5. The carboxamide compounds according to claim 1, wherein A and R3 are connected to one another such that
the group 317 of formula I denotes a group of partial formula II 318 and Q denotes a group, selected from the partial formulae IIIa to IIIg—CR6R7— IIIa—CR6═CR7— IIIb—N═CR8— IIIc—N═N— IIId—CO—NR9— IIIe—CR8═N— IIIf—CO— IIIg and L1, L2, L3, R6, R7, R8 and R9 have the meanings given in claim 1.
- 6. The carboxamide compounds according to claim 1, wherein R1, R2 independently of one another denote H, C1-6-alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl-, ω-hydroxy-C2-3-alkyl, ω-(C1-3-alkoxy)-C2-3-alkyl-, C1-4-alkoxy-carbonyl-C1-3-alkyl, amino-C2-4-alkyl-, C1-3-alkyl-amino-C2-4-alkyl- or di-(C1-3-alkyl)-amino-C2-4-alkyl-, phenyl or phenyl-C1-3-alkyl-,
while in the above mentioned groups and residues one or more C atoms may be mono- or polysubstituted by F and/or one or two C atoms independently of one another may be monosubstituted by Cl or Br and the phenyl group may be mono- or polysubstituted by the group R12 defined in claim 1 and/or monosubstituted by nitro.
- 7. Carboxamide compounds according to claim 1, wherein R1 and R2 form an alkylene bridge according to claim 1 in such a way that R1R2N— forms a group selected from azetidine, pyrrolidine, piperidine, azepan, 2,5-dihydro-1H-pyrrole, 1,2,3,6-tetrahydro-pyridine, 2,3,4,7-tetrahydro-1H-azepinyl, 2,3,6,7-tetrahydro-1H-azepine, morpholine, thiomorpholine, and piperazine, wherein the free imine function may be substituted with R13,
wherein one or more H atoms may be replaced by R14, and/or may be substituted in the manner specified in claim 1 with one or two identical or different carbo- or heterocyclic groups Cy, where R13, R14 and Cy have the meanings given in claim 1.
- 8. The carboxamide compounds according to claim 1, wherein the group
- 9. The carboxamide compounds according to claim 1, wherein X denotes a single bond or an unbranched bridge selected from C1-6-alkylene, C2-6-alkenylene, C2-6-alkynylene, C1-6-alkylenoxy, carbonyl, carbonyl-C1-6-alkylene or C1-6-alkylene-amino, wherein the amino group may be substituted with R4,
while one or two C atoms may be substituted as specified in claim 1 and/or the alkylene bridge may be connected to R1 as specified in claim 1.
- 10. The carboxamide compounds according to claim 1, wherein X denotes a single bond, carbonyl or an alkylene bridge selected from methylene, 1,2-ethylene, 1,3-propylene and 1,4-butylene,
wherein one or two C atoms independently of one another may be substituted with a hydroxy, ω-hydroxy-C1-3-alkyl, ω-(C1-3-alkoxy)-C1-3-alkyl-and/or C1-3-alkoxy group and/or in each case may be substituted with one or two identical or different C1-4-alkyl groups, and in each case one or more C atoms may be mono- or polysubstituted by F and/or in each case one or two C atoms independently of one another may be monosubstituted by Cl or Br.
- 11. The carboxamide compounds according to claim 1, wherein Z denotes methylene, 1,2-ethylene, 1,3-propylene, 1,4-butylene, methyleneoxy, 1,2-ethyleneoxy, 1,3-propyleneoxy or 1,4-butyleneoxy,
wherein one or two C atoms independently of one another may be substituted with a hydroxy, ω-hydroxy-C1-3-alkyl, ω-(C1-3-alkoxy)-C1-3-alkyl-and/or C1-3-alkoxy group and/or in each case may be substituted with one or two identical or different C1-4-alkyl groups, and in each case one or more C atoms may be mono- or polysubstituted by F and/or in each case one or two C atoms independently of one another may be monosubstituted by Cl or Br and R3 may be connected to Z so as to include the N atoms linked to R3 forming a heterocyclic group.
- 12. The carboxamide compounds according to claim 11, wherein Z is selected from the group of the bridges —CH2—, —CH2—CH2—, —CH2—CH(CH3)—, —CH2—C(CH3)2—, —CH(CH3)—CH2—, —C(CH3)2—CH2— and —CH2—O— or Z is linked to R3 in such a way that the group of partial formula
- 13. The carboxamide compounds according to claim 1, wherein R3 is selected from among methyl, ethyl, n-propyl, iso-propyl, 2-hydroxyethyl, 3-hydroxy-n-propyl and 2-hydroxy-1-methyl-ethyl-, while in the above mentioned groups one, two or three H atoms may be replaced by F, or is selected from among H, amino-C2-3-alkyl-, C1-3-alkyl-amino-C2-3-alkyl- and di-(C1-3-alkyl)-amino-C2-3-alkyl-.
- 14. The carboxamide compounds according to claim 1, wherein the group Y is selected from among the bivalent cyclic groups 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, 1,3- and 1,4-cyclohexylene, 1,3-phenylene, 1,4-phenylene, 1,3- and 1,4-cyclohexenylene, 1,4-cycloheptylene, 1,4-cycloheptenylene, 1,3-pyrrolidinylene, 1,3-pyrrolinylene, 1,3-pyrrolylene, 1,4-piperidinylene, 1,4-tetrahydropyridinylene, 1,4-dihydropyridinylene, 2,4- and 2,5-pyridinylene or 1,4-piperazinylene,
while the above mentioned 5-, 6- or 7-membered groups may be connected through two common, adjacent C atoms fused with a phenyl or pyridine ring, the above mentioned cyclic groups may be mono- or polysubstituted at one or more C atoms with R20, in the case of a phenyl group they may also additionally be monosubstituted by nitro, and/or may be substituted with R21 at one or more N atoms, while R1 may be connected to Y and/or R3 to Y as specified in claim 1, and R1, R3, R20 and R21 have the meanings given in claim 1.
- 15. The carboxamide compounds according to claim 14, wherein R1 is linked to Y in such a way that the group of partial formula
- 16. The carboxamide compounds according to claim 1, wherein group A is selected from among the bivalent cyclic groups 1,2-cyclopropylene, 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3-cyclopentenylene, 1,3- and 1,4-cyclohexylene, 1,3- and 1,4-phenylene, 1,3- and 1,4-cyclohexenylene, 1,4-cycloheptylene, 1,4-cycloheptenylene, 1,3-pyrrolidinylene, 1,3-pyrrolinylene, 1,3-pyrrolylene, 1,4-piperidinylene, 1,4-tetrahydropyridinylene, 1,4-dihydropyridinylene, 2,4- and 2,5-pyridinylene, 1,4-piperazinylene, 7-aza-bicyclo[2.2.1]heptan-2,7-diyl and 8-aza-bicyclo[3.2.1]octan-3,8-diyl,
while the above mentioned 5-, 6- or 7-membered groups may be linked by two common, adjacent C atoms fused with a phenyl or pyridine ring, and the above mentioned cyclic groups may be mono- or polysubstituted at one or more C atoms with R20, in the case of a phenyl ring they may also additionally be monosubstituted by nitro, and/or they may be substituted at one or more N atoms with R21, and R20, R21 and Y have the meanings given in claim 1.
- 17. The carboxamide compounds according to claim 1, wherein group B is selected from among cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexanonyl, cyclohexenyl, phenyl, cycloheptyl, cycloheptenyl, aziridinyl, azetidinyl, pyrrolidinyl, pyrrolinyl, pyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, pyridinyl, azepanyl, piperazinyl, 1H-pyrazolyl, imidazolyl, triazolyl, tetrazolyl, morpholinyl, thiomorpholinyl, indolyl, isoindolyl, quinolinyl, benzoimidazolyl, isoquinolinyl, furanyl and thienyl,
while the bond to the group W or optionally directly to the group A is made via a C atom of the carbocyclic moiety or of the optionally fused-on phenyl or pyridine ring or via an N or C atom of the heterocyclic moiety, or B together with the group W connected by a double bond is selected from the group cyclopentylidene-methyl, cyclohexylidene-methyl and cyclohexanone-4-ylidene-methyl, and the above mentioned cyclic groups may be mono- or polysubstituted at one or more C atoms with R20, in the case of a phenyl group may also additionally be monosubstituted by nitro, and/or may be substituted with R21 at one or more N atoms, and R20 and R21 have the meanings given in claim 1.
- 18. Carboxamide compounds according to claim 1, wherein group B is selected from among C1-6-alkyl, C1-6-alkenyl, C1-6-alkynyl, C3-7-cycloalkyl-C1-3-alkyl-, C3-7-cycloalkenyl-C1-3-alkyl-, C3-7-cycloalkyl-C1-3-alkenyl- or C3-7-cycloalkyl-C1-3-alkynyl-, wherein one or more C atoms may be mono- or polysubstituted by halogen and/or monosubstituted by hydroxy or cyano and/or cyclic groups may be mono- or polysubstituted by R20, and
W denotes a single bond, —O—, a C1-4-alkylene, C2-4-alkenylene, C2-4-alkynylene, C1-4-alkyleneoxy, oxy-C1-4-alkylene-, C1-3-alkylene-oxy-C1-3-alkylene-, imino, N—(C1-3-alkyl)-imino-, imino-C1-4-alkylene-, N—(C1-3-alkyl)-imino-C1-4-alkylene-, C1-4-alkylene-imino- or C1-4-alkylene-N—(C1-3-alkyl)-imino-group, while one or two C atoms independently of one another may be substituted with a hydroxy, ω-hydroxy-C1-3-alkyl, ω-(C1-3-alkoxy)-C1-3-alkyl- and/ or C1-3-alkoxy group and/or with one or two identical or different C1-4-alkyl groups, and k denotes 0 or 1 and R20 has the meanings given in claim 1.
- 19. Carboxamide compounds according to claim 1, wherein k=0 and the group A is linked to the group B through a common C atom forming a spirocyclic ring system,
while the group A represents a saturated 5- to 7-membered carbo- or heterocyclic group and the group B denotes a saturated 4- to 7-membered carbo- or heterocyclic group, and the heterocyclic groups in each case contain an N, O or S atom, and a phenyl or pyridine ring may be fused to a 5- to 7-membered group B through two adjacent C atoms, and the above mentioned cyclic groups may be mono- or polysubstituted at one or more C atoms with R20, in the case of a fused-on phenyl ring they may additionally be monosubstituted by nitro, and/or may be substituted with R21 at one or more N atoms, while R20 and R21 have the meanings given in claim 1.
- 20. The carboxamide compounds according to claim 1, wherein k=0 and the group B is linked to the group A through two common, adjacent atoms forming a fused, bicyclic saturated, unsaturated or aromatic, 8- to 12-membered carbo- or heterocyclic ring system,
while the heterocyclic ring system has one or more identical or different heteroatoms selected from N, O and/or S, and the bicyclic ring system may be mono- or polysubstituted at one or more C atoms with R20, in the case of a fused-on phenyl ring it may also additionally be monosubstituted by nitro, and/or may be substituted with R21 at one or more N atoms, while R20 and R21 have the meanings given in claim 1.
- 21. The carboxamide compounds according to claim 1, wherein W is a single bond, —CH2— or —CH═.
- 22. Carboxamide compounds according to claim 1, wherein
Y, A independently of one another are selected from among the bivalent cyclic groups 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-piperidinylene, 1,2,3,6-tetrahydro-pyridin-1,4-ylene, 2,5-pyridinylene and 1,4-piperazinylene, while A may also be connected to R3 according to claim 3, and the above mentioned cyclic groups may be mono- or polysubstituted by R20 at one or more C atoms, in the case of a phenyl group they may also additionally be monosubstituted by nitro, and/or may be substituted by R21 at one or more N atoms, B denotes phenyl or cyclohexyl, while the above mentioned groups may be mono- or polysubstituted by R20 and/or the phenyl ring may additionally be monosubstituted by nitro, while R20 has the meanings given in claim 1, and W is a single bond, —CH2— or —CH═, and Z denotes —CH2—CH2—, —CH2—CH(CH3)—, —CH2—C(CH3)2—, —CH(CH3)—CH2—, —C(CH3)2—CH2— or —CH2—O— or
is linked to R3 in such a way that the group of partial formula 325 of formula I has a meaning selected from 1,3-pyrrolidinylene and 1,3-piperidinylene and R3, R20 and R21 have the meanings given in claim 1.
- 23. Carboxamide compounds according to claim 1 from among formulae I.1 to I.14
- 24. Carboxamide compounds according to claim 1, characterised by the formula I.15
- 25. Carboxamide compounds according to claim 24, wherein U and V in each case represent a C atom.
- 26. Carboxamide compounds according to claim 1, wherein X is —CH2—, —CH(CH3)— or —C(CH3)2—.
- 27. Carboxamide compounds according to claim 26, wherein
R25, R26, R27 independently of one another denote F, Cl, Br, I, OH, cyano, methyl, difluoromethyl, trifluoromethyl, ethyl, n-propyl, iso-propyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, n-propoxy or iso-propoxy, in the case of a substitution of a phenyl group they may also denote nitro, while repeatedly occurring groups R25, R26, R27 may have identical or different meanings, and j is 0, 1 or 2, and m, n independently of one another are 0 or 1.
- 28. Carboxamide compounds according to claim 1, wherein R6, R7, R8 and/or R9 independently of one another denote H, methyl, trifluoromethyl, ethyl, iso-propyl or n-propyl, if R6, R7 also represent F.
- 29. Carboxamide compounds according to claim 1 selected from among the formulae:
(1) 7-(4-chloro-phenyl)-3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-3H-quinazolin-4-one (2) 3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-7-p-tolyl-3H-quinazolin-4-one (3) 3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-7-(4-trifluoromethyl-phenyl)-3H-quinazolin-4-one (4) 7-(4-methoxy-phenyl)-3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-3H-quinazolin-4-one (5) 7-(3.4-dichloro-phenyl)-3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-3H-quinazolin-4-one (6) 7-(4-fluoro-phenyl)-3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-3H-quinazolin-4-one (7) 7-(4-ethyl-phenyl)-3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-3H-quinazolin-4-one (8) 2-methyl-3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-7-(4-trifluoromethyl-phenyl)-3H-quinazolin-4-one (9) 2-methyl-3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-7-p-tolyl-3H-quinazolin-4-one (10) 7-(4-chloro-phenyl)-2-methyl-3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-3H-quinazolin-4-one (11) 7-(4-chloro-phenyl)-3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-1H-quinazolin-2,4-dione (12) 7-(4-chloro-phenyl)-3-{2-[4-((S)-2-methoxymethyl-pyrrolidin-1-ylmethyl)-phenyl]-ethyl}-3H-quinazolin-4-one (13) 7-(4-chloro-phenyl)-3-[2-(4-dimethylaminomethyl-phenyl)-ethyl]-3H-quinazolin-4-one (14) 7-(4-chloro-phenyl)-3-[2-(4-piperidin-1-ylmethyl-phenyl)-ethyl]-3H-quinazolin-4-one (15) 7-(4-chloro-phenyl)-3-[2-(4-morpholin-4-ylmethyl-phenyl)-ethyl]-3H-quinazolin-4-one (16) 7-(4-chloro-phenyl)-3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-3H-benzo[d][1,2,3]triazin-4-one (17) 5-(4-fluoro-phenyl)-2-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-isoindol-1,3-dione (18) 4′-chloro-biphenyl-4-carboxylic acid [2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (19) 4′-chloro-biphenyl-4-carboxylic acid-[2-(4-diethylaminomethyl-phenyl)-ethyl]-amide (20) 4′-chloro-biphenyl-4-carboxylic acid-[2-(4-piperidin-1-ylmethyl-phenyl)-ethyl]-amide (21) 4′-methoxy-biphenyl-4-carboxylic acid-[2-(4-diethylaminomethyl-phenyl)-ethyl]-amide (22) 4′-chloro-biphenyl-4-carboxylic acid-[2-(4-diethylaminomethyl-phenyl)-ethyl]-methyl-amide (23) 4-(4-chloro-phenyl)-cyclohexanecarboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (24) 4-methylphenyl-piperidine-1-carboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (25) 4-(4-chloro-phenyl)-3.6-dihydro-2H-pyridine-1-carboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (26) 4-(4-chloro-phenyl)-piperidine-1-carboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (27) 4′-chloro-biphenyl-4-carboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-propyl]-amide (28) 4′-chloro-biphenyl-4-carboxylic acid-(4-pyrrolidin-1-ylmethyl-benzyloxy)-amide (29) 4-cyclohexyl-N-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-benzamide (30) 4′-chloro-biphenyl-4-carboxylic acid-[2-(3-methoxy-4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (31) 7-(4-chloro-phenyl)-3-{2-[6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-ethyl}-3H-quinazolin-4-one (32) 4′-chloro-biphenyl-4-carboxylic acid-{2-[6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-ethyl}-amide (33) 7-(3-methoxy-phenyl)-3-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-3H-quinazolin-4-one (34) 4-(4-oxo-cyclohexyl)-N-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-benzamide (35) 4-cyclohexyl-1-cylohexylcarboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (36) 4-benzyl-piperidine-1-carboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (37) 4-cyclohexyl-piperidine-1-carboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (38) 4-(4-chloro-phenyl)-piperazine-1-carboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (39) 4-(4-fluoro-phenyl)-piperidine-1-carboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (40) 4-(4-methoxy-phenyl)-piperazine-1-carboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (41) 4-phenyl-piperidine-1-carboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (42) (4′-chloro-biphenyl-4-yl)-[3-(4-pyrrolidin-1-ylmethyl-phenyl)-piperidin-1-yl]-methanone (43) 4′-chloro-biphenyl-4-carboxylic acid-[2-methyl-2-(4-pyrrolidin-1-ylmethyl-phenyl)-propyl]-amide (44) 4′-chloro-biphenyl-4-carboxylic acid-[2-(4-pyrrolidin-1-ylmethyl-cyclohexyl)-ethyl]-amide (45) 4-benzyl-N-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-benzamide (46) 4-(4-oxo-cyclohexylidenemethyl)-N-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-benzamide (47) 4′-chloro-biphenyl-4-carboxylic acid-[2-(2-fluoro-4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (48) 5-(4-chloro-phenyl)-2-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-2.3-dihydro-isoindol-1-one (49) 4-piperidin-1-yl-N-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-benzamide (50) 7-(4-chloro-phenyl)-3-{2-[4-(4-hydroxy-4-phenyl-piperidin-1-ylmethyl)-phenyl]-ethyl}-3H-benzo[d][1,2,3]triazin-4-one (51) 7-(4-chloro-phenyl)-3-{2-[4-(3-aza-spiro[5.5]undec-3-ylmethyl)-phenyl]-ethyl}-3H-quinazolin-4-one (52) 7-(4-chloro-phenyl)-3-{2-[4-(3-aza-spiro[5.5]undec-3-ylmethyl)-phenyl]-ethyl}-3H-benzo[d][1,2,3]triazin-4-one (53) 7-(4-chloro-phenyl)-3-{2-[4-(4-hydroxy-4-phenyl-piperidin-1-ylmethyl)-phenyl]-ethyl}-3H-quinazolin-4-one (54) 7-(4-chloro-phenyl)-3-(2-{4-[4-(pyridin-2-yloxy)-piperidin-1-ylmethyl]-phenyl}-ethyl)-3H-quinazolin-4-one (55) 6-(4-chloro-phenyl)-2-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-2H-isoquinolin-1-one (56) 4′-chloro-biphenyl-4-carboxylic acid [2-(3-bromo-4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (57) 4′-chloro-biphenyl-4-carboxylic acid [2-(3-methyl-4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (58) 4′-chloro-biphenyl-4-carboxylic acid {2-[4-(1-ethyl-piperidin-2-yl)-phenyl]-ethyl}-amide (59) 4′-chloro-biphenyl-4-carboxylic acid{2-[4-(4-acetyl-piperazin-1-ylmethyl)-phenyl]-ethyl}-amide (60) 4′-chloro-biphenyl-4-carboxylic acid{2-[4-(2-aza-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-phenyl]-ethyl}-amide (61) 4′-chloro-biphenyl-4-carboxylic acid {2-[4-(1,3-dihydro-isoindol-2-ylmethyl)-phenyl]-ethyl}-amide (62) 4′-chloro-biphenyl-4-carboxylic acid (2-{4-[(diisopropylamino)-methyl]-phenyl}-ethyl)-amide (63) 4′-chloro-biphenyl-4-carboxylic acid {2-[3-bromo-4-(2,5-dihydro-pyrrol-1-ylmethyl)-phenyl]-ethyl}-amide (64) 4′-chloro-biphenyl-4-carboxylic acid{2-[4-(2-dimethylaminomethyl-pyrrolidin-1-ylmethyl)-phenyl]-ethyl}-amide (65) 4′-chloro-biphenyl-4-carboxylic acid{2-[4-(3-dimethylamino-pyrrolidin-1-ylmethyl)-phenyl]-ethyl}-amide (66) 4′-chloro-biphenyl-4-carboxylic acid [2-(2-bromo-4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (67) 4-pent-1-ynyl-N-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-benzamide (68) 4′-chloro-biphenyl-4-carboxylic acid [2-(6-pyrrolidin-1-ylmethyl-pyridin-3-yl)-ethyl]-amide (69) 4′-chloro-biphenyl-4-carboxylic acid [2-(1-pyrrolidin-1-yl-indan-5-yl)-ethyl]-amide (70) 4′-chloro-biphenyl-4-carboxylic acid [2-(2-nitro-4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (71) 2′,4′-dichloro-biphenyl-4-carboxylic acid [2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (72) 4′-chloro-biphenyl-4-carboxylic acid{2-[4-(3-amino-pyrrolidin-1-ylmethyl)-phenyl]-ethyl}-amide (73) 4′-chloro-biphenyl-4-carboxylic acid{2-[4-(2-aminomethyl-pyrrolidin-1-ylmethyl)-phenyl]-ethyl}-amide (74) 4′-chloro-biphenyl-4-carboxylic acid{2-[4-(2-methyl-2,6-diaza-spiro[3.4]oct-6-ylmethyl)-phenyl]-ethyl}-amide (75) 4′-chloro-biphenyl-4-carboxylic acid [2-(5-pyrrolidin-1-ylmethyl-pyridin-2-yl)-ethyl]-amide (76) 4′-chloro-biphenyl-4-carboxylic acid [2-(3-ethyl-4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (77) 4′-bromo-biphenyl-4-carboxylic acid {2-[4-(2,5-dihydro-pyrrol-1-ylmethyl)-phenyl]-ethyl}-amide (78) 4-(5-chloro-thiophen-2-yl)-N-[2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-benzamide (79) 4′-chloro-biphenyl-4-carboxylic acid [2-(2-methyl-4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (80) 4′-bromo-3-fluoro-biphenyl-4-carboxylic acid {2-[3-bromo-4-(2,5-dihydro-pyrrol-1-ylmethyl)-phenyl]-ethyl}-amide (81) 4′-chloro-2-fluoro-biphenyl-4-carboxylic acid [2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (82) 4′-ethyl-biphenyl-4-carboxylic acid [2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (83) tert.butyl [1-(4-{2-[(4′-chloro-biphenyl-4-carbonyl)-amino]-ethyl}-benzyl)-pyrrolidin-2-ylmethyl]-carbaminate (84) 4′-chloro-biphenyl-4-carboxylic acid {2-[4-(2-methyl-piperidin-1-ylmethyl)-phenyl]-ethyl}-amide (85) 4′-chloro-biphenyl-4-carboxylic acid {2-[4-(2-methyl-pyrrolidin-1-ylmethyl)-phenyl]-ethyl}-amide (86) 4′-chloro-biphenyl-4-carboxylic acid (2-{4-[(cyclopropylmethyl-amino)-methyl]-phenyl}-ethyl)-amide (87) 4′-chloro-biphenyl-4-carboxylic acid {2-[4-(3.4-dihydro-1H-isoquinolin-2-ylmethyl)-phenyl]-ethyl}-amide (88) 4′-chloro-biphenyl-4-carboxylic acid [2-(4-{[(2-hydroxy-ethyl)-methyl-amino]-methyl}-phenyl)-ethyl]-amide (89) tert.butyl [1-(4-{2-[(4′-chloro-biphenyl-4-carbonyl)-amino]-ethyl}-benzyl)-pyrrolidin-3-yl]-carbaminate (90) 4′-chloro-biphenyl-4-carboxylic acid {2-[4-(2,6-dimethyl-piperidin-1-ylmethyl)-phenyl]-ethyl}-amide (91) 4′-chloro-biphenyl-4-carboxylic acid [2-(4-azetidin-1-ylmethyl-phenyl)-ethyl]-amide (92) 3,4′-dichloro-biphenyl-4-carboxylic acid [2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (93) 4′-fluoro-biphenyl-4-carboxylic acid [2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (94) 4′-chloro-3-fluoro-biphenyl-4-carboxylic acid [2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (95) 2′-fluoro-4′-chloro-biphenyl-4-carboxylic acid [2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (96) 5-(4-chloro-phenyl)-pyridine-2-carboxylic acid [2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (97) 4′-chloro-biphenyl-4-carboxylic acid {2-[4-(2,5-dihydro-pyrrol-1-ylmethyl)-phenyl]-ethyl}-amide (98) 4′-bromo-biphenyl-4-carboxylic acid [2-(4-pyrrolidin-1-ylmethyl-phenyl)-ethyl]-amide (99) 4′-chloro-biphenyl-4-carboxylic acid {2-[4-(1-pyrrolidin-1-yl-ethyl)-phenyl]-ethyl}-amide.
- 30. Carboxamide compounds according to claim 29 selected from among the formulae (1), (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13), (14), (15), (16), (17), (18), (19), (20), (21), (22), (23), (24), (25), (25), (26), (27), (28), (29), (30), (47) and (50) to (99).
- 31. Process for preparing carboxamide compounds of formula I
- 32. The physiologically acceptable salts of the carboxamide compounds according to claim 1.
- 33. Method of influencing the eating behavior of a mammal comprised of administering to a mammal a pharmaceutically effective amount of carboxamide compound according to claim 32.
- 34. A composition comprised of at least one carboxamide compound according to claim 1 further comprised of one or more physiologically acceptable excipients.
- 35. Pharmaceutical composition, containing at least one carboxamide compound according to claim 34 optionally together with one or more inert carriers and/or diluents.
- 36. Method of influencing the eating behaviour of a mammal comprised of administering to a mammal a pharmaceutically effective amount of a compound according to claim 1.
- 37. A method of reducing the body weight and/or prevention of an increase of body weight of a mammal comprised of the administration of a pharmaceutically effective amount of carboxamide compound according to claim 1 to a mammal.
- 38. Use of at least one carboxamide compound according to claim 1 for preparing a pharmaceutical composition with an MCH-receptor-antagonist activity.
- 39. Method of preventing and/or treating symptoms and/or diseases which are caused by MCH or otherwise casually connected with MCH, comprised of the administration to a patient in need thereof a pharmaceutically effective amount of a compound according to claim 1.
- 40. A method of treating metabolic disorders and/or eating disorders, obesity, bulimia, bulimia nervosa, cachexia, anorexia nervosa and hyperphagia comprised of the administration to a patient in need thereof of a pharmaceutically effective amount of a carboxamide compound according to claim 1.
- 41. Method of preventing and/or treating diseases and/or disorders associated with obesity, particularly diabetes, especially type II diabetes, complications of diabetes including diabetic retinopathy, diabetic neuropathy, diabetic nephropathy, insulin resistance, pathological glucose tolerance, encephalorrhagia, cardiac insufficiency, cardiovascular diseases, particularly arteriosclerosis and high blood pressure, arthritis and gonitis comprised of administering to a patient in need thereof a pharmaceutically effective amount of a compound according to claim 1.
- 42. Method of preventing or treating hyperlipidaemia, cellulitis, fat accumulation, malignant mastocytosis, systemic mastocytosis, emotional disorders, affective disorders, depression, anxiety, sleep disorders, reproductive disorders, sexual disorders, memory disorders, epilepsy, forms of dementia and hormonal disorders comprised of administering to a patient in need thereof a pharmaceutically effective amount of a carboxamide compound according to claim 1.
- 43. A method of preventing and/or treating micturition disorders, selected from a list consisting of urinary incontinence, hyperactive urinary bladder, urgency, nycturia and enuresis comprised of administering to a patient in need thereof a pharmaceutically effective amount of a compound according to claim 1.
- 44. Pharmaceutical compositions, containing a first active substance selected from the carboxamide compounds according to claim 1 and a second active substance selected from the group consisting of active substances for the treatment of diabetes, active substances for the treatment of diabetic complications, active substances for the treatment of obesity, preferably other than MCH antagonists, active substances for the treatment of high blood pressure, active substances for the treatment of hyperlipidaemia, including arteriosclerosis, active substances for the treatment of arthritis, active substances for the treatment of anxiety states and active substances for the treatment of depression, optionally together with one or more inert carriers and/or diluents.
Priority Claims (1)
Number |
Date |
Country |
Kind |
10238865 |
Aug 2002 |
DE |
|
RELATED APPLICATIONS
[0001] The priority benefit of DE 102 38 865.2, filed Aug. 24, 2002 and U.S. Provisional Application No. 60/408,224, filed Sep. 4, 2002 are hereby claimed, both of which are incorporated by reference herein.
Provisional Applications (1)
|
Number |
Date |
Country |
|
60408224 |
Sep 2002 |
US |