CA2504160A1 - Novel alkyne compounds having an mch antagonistic effect and medicaments containing these compounds - Google Patents

Novel alkyne compounds having an mch antagonistic effect and medicaments containing these compounds Download PDF

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CA2504160A1
CA2504160A1 CA002504160A CA2504160A CA2504160A1 CA 2504160 A1 CA2504160 A1 CA 2504160A1 CA 002504160 A CA002504160 A CA 002504160A CA 2504160 A CA2504160 A CA 2504160A CA 2504160 A1 CA2504160 A1 CA 2504160A1
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Prior art keywords
alkyl
phenyl
chloro
pyridin
methyl
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CA002504160A
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French (fr)
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CA2504160C (en
Inventor
Stephan-Georg Muller
Dirk Stenkamp
Kirsten Arndt
Gerald Juergen Roth
Ralf Richard Hermann Lotz
Thorsten Lehmann-Lintz
Martin Lenter
Philipp Lustenberger
Klaus Rudolf
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Boehringer Ingelheim Pharma GmbH and Co KG
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Individual
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
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Abstract

The present invention relates to alkyne compounds of general formula I

(see formula I) wherein the groups and residues A, B, W, X, Y, Z, R1 and R2 have the meanings given in claim 1. The invention further relates to pharmaceutical compositions containing at least one alkyne according to the invention. In view of their MCH-receptor antagonistic activity the pharmaceutical compositions according to the invention are suitable for the treatment of metabolic disorders and/or eating disorders, particularly obesity, bulimia, anorexia, hyperphagia and diabetes.

Claims (34)

1. Alkyne compounds of general formula I
wherein R1, R2 independently of one another denote H, a C1-8-alkyl or C3-7-cycloalkyl group optionally substituted by the group R11, while a -CH2- group in position 3 or 4 of a 5-, 6- or 7-membered cycloalkyl group may be replaced by -O-, -S- or -NR13 -, or a phenyl or pyridinyl group optionally mono- or polysubstituted by the group R12 and/or monosubstituted by nitro, or R1 and R2 form a C2-8-alkylene bridge wherein - one or two -CH2- groups independently of one another may be replaced by -CH=N- or -CH=CH- and/or - one or two -CH2- groups may be replaced independently of one another by -O-, -S-, -SO-, -(SO2)-, -C=N-R18-, -C=N-O-R18-, -CO-, -C(=CH2)- or -NR13- in such a way that heteroatoms are not directly connected to one another, while in the above-defined alkylene bridge one or more H atoms may be replaced by R14, and while the above-defined alkylene bridge may be substituted by one or two identical or different carbo- or heterocyclic groups Cy in such a way that the bond between the alkylene bridge and the group Cy is formed - via a single or double bond, - via a common C atom forming a spirocyclic ring system, - via two common, adjacent C and/or N atoms forming a fused bicyclic ring system or - via three or more C and/or N atoms forming a bridged ring system, X denotes a single bond or a C1-6-alkylene bridge wherein - a -CH2- group may be replaced by -CH=CH- or -C.ident.C- and/or - one or two -CH2- groups may be replaced independently of one another by -O-, -S-, -(SO)-, -(SO2)-, -CO- or -NR4- in such a way that in each case two 0, S or N atoms or an O and an S atom are not directly connected to one another, while the bridge X may be attached to R1 including the N atom attached to R1 and X forming a heterocyclic group, while the bridge X may additionally also be attached to R2 , including the N-atom attached to R2 and X , forming a heterocyclic group, and two C atoms or one C and one N atom of the alkylene bridge may be joined together by an additional C1-4-alkylene bridge, and a C atom may be substituted by R10 and/or one or two C atoms in each case may be substituted with one or two identical or different substituents selected from C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, C4-7-cycloalkenyl and C4-7-cycloalkenyl-C1-3-alkyl, while two alkyl and/or alkenyl substituents may be joined together, forming a carbocyclic ring system, and W, Z independently of one another denote a single bond or a C1-4-alkylene bridge, while in the group W and/or Z a -CH2- group not adjacent to the -C.ident.C group may be replaced by -O or -NR5-, and two adjacent C atoms or one C atom and an adjacent N atom may be joined together by an additional C1-4-alkylene bridge, and in the alkylene bridge and/or in the additional alkylene bridge a C
atom may be substituted by R10 and/or one or two C atoms independently of one another may be substituted by one or two identical or different C1-6-alkyl groups, while two alkyl groups may be joined together, forming a carbocyclic ring, and Y denotes one of the meanings given for Cy, while R1 may be attached to Y including the group X and the N
atom attached to R1 and X , forming a heterocyclic group fused to Y, and/or X may be attached to Y forming a carbo- or heterocyclic group fused to Y, and A denotes one of the meanings given for Cy and B denotes one of the meanings given for Cy or 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 may be monosubstituted by hydroxy or cyano and/ or cyclic groups may be mono- or polysubstituted by R20, Cy denotes a carbo- or heterocyclic group selected from one of the following meanings - a saturated 3- to 7-membered carbocyclic group, - an unsaturated 4- to 7-membered carbocyclic group, - a phenyl group, - a saturated 4- to 7-membered or unsaturated 5- to 7-membered heterocyclic group with an N, O or S atom as heteroatom, - a saturated or unsaturated 5- to 7-membered heterocyclic group with two or more N atoms or with one or two N atoms and an O
or S atom as heteroatoms, - an aromatic heterocyclic 5- or 6-membered group with one or more identical or different heteroatoms selected from N, O
and/or S, while the above-mentioned 4-, 5-, 6- or 7-membered groups may be attached via two common, adjacent C atoms fused to a phenyl or pyridine ring, and in the above-mentioned 5-, 6- or 7-membered groups one or two non-adjacent -CH2- groups may be replaced independently of one another by a -CO-, -C(=CH2)-, -(SO)- or -(SO2)- group, and the above-mentioned saturated 6- or 7-membered groups may also be present as bridged ring systems with an imino, (C1-4-alkyl)-imino, methylene, (C1-4-alkyl)-methylene or di-(C1-4-alkyl)-methylene bridge, 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 they may also additionally be monosubstituted with nitro, and/or one or more NH groups may be substituted with R21, R4, R5 independently of one another have one of the meanings given for R17, R10 denotes hydroxy, .omega.-hydroxy-C1-3-alkyl, C1-4-alkoxy, .omega.-(C1-4-alkoxy)-C1-3-alkyl, carboxy, C1-4-alkoxycarbonyl, amino, C1-4-alkyl-amino, di-(C1-4-alkyl)-amino, cyclo-C3-6-alkyleneimino, amino-C1-3-alkyl, C1-4-alkyl-amino-C1-3-alkyl, di-(C1-4-alkyl)-amino-C1-3-alkyl, cyclo-C3-6-alkyleneimino-C1-3-alkyl, amino-C2-3-alkoxy, C1-4-alkyl-amino-C2-3-alkoxy, di-(C1-4-alkyl)-amino-C2-3-alkoxy, cyclo-C3-6-alkyleneimino-C2-3-alkoxy, aminocarbonyl, C1-4-alkyl-aminocarbonyl, di-(C1-4-alkyl)-aminocarbonyl, cyclo-C3-6-alkyleneimino-carbonyl, R11 denotes C2-6-alkenyl, C2-6-alkynyl, R15-O, R15-O-CO, R15-CO-O, R16R17N, R18R19N-CO or Cy, R12 has one of the meanings given for R20, R13 has one of the meanings given for R17, with the exception of carboxy, R14 denotes halogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, R15-O, R15-O-CO, R15-CO, R15-CO-O, R16R17N, R18R19N-CO, R15-O-C1-3-alkyl, R15-O-CO-C1-3-alkyl, R15-O-CO-NH, R15-SO2-NH, R15-O-CO-NH-C1-3-alkyl, R15-SO2-NH-C1-3-alkyl, R15-CO-C1-3-alkyl, R15-CO-O-C1-3-alkyl, R16R17N-C1-3-alkyl, R18R19N-CO-C1-3-alkyl or Cy-C1-3-alkyl, R15 denotes H, C1-4-alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, phenyl, phenyl-C1-3-alkyl, pyridinyl or pyridinyl-C1-3-alkyl, R16 denotes H, C1-6-alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, C4-7-cycloalkenyl, C4-7-cycloalkenyl-C1-3-alkyl, .omega.-hydroxy-C2-3-alkyl, .omega.-(C1-4-alkoxy)-C2-3-alkyl, amino-C2-6-alkyl, C1-4-alkyl-amino-C2-6-alkyl, di-(C1-4-alkyl)-amino-C2-6-alkyl or cyclo-C3-6-alkyleneimino-C2-6-alkyl, R17 has one of the meanings given for R16 or denotes phenyl, phenyl-C1-3-alkyl, pyridinyl, dioxolan-2-yl, -CHO, C1-4-alkylcarbonyl, carboxy, hydroxycarbonyl-C1-3-alkyl, C1-4-alkoxycarbonyl, C1-4-alkoxycarbonyl-C1-3-alkyl, C1-4-alkylcarbonylamino-C2-3-alkyl, N-(C1-4-alkylcarbonyl)-N-(C1-4-alkyl)-amino-C2-3-alkyl, C1-4-alkylsulphonyl, C1-4-alkylsulphonylamino-C2-3-alkyl or N-(C1-4-alkylsulphonyl)-N-(C1-4-alkyl)-amino-C2-3-alkyl R18, R19 independently of one another denote H or C1-6-alkyl, R20 denotes halogen, hydroxy, cyano, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, C3-7-cycloalkyl- C1-3-alkyl, hydroxy-C1-3-alkyl, R22-C1-3-alkyl or has one of the meanings given for R22, R21 denotes C1-4-alkyl, .omega.-hydroxy-C2-6-alkyl, .omega.-C1-4-alkoxy-C2-6-alkyl, .omega.-C1-4-alkyl-amino-C2-6-alkyl, C1-di-(C1-4-alkyl)-amino-C2-6-alkyl, .omega.-cyclo-C3-6-alkyleneimino-C2-6-alkyl, phenyl, phenyl-C1-3-alkyl, C1-4-alkyl-carbonyl, C1-4-alkoxy-carbonyl, C1-4-alkylsulphonyl, phenylcarbonyl or phenyl-C1-3-alkyl-carbonyl, R22 denotes pyridinyl, phenyl, phenyl-C1-3-alkoxy, OHC, HO-N=HC, C1-4-alkoxy-N=HC, C1-4-alkoxy, C1-4-alkylthio, carboxy, C1-4-alkylcarbonyl, C1-4-alkoxycarbonyl, aminocarbonyl, C1-4-alkylaminocarbonyl, di-(C1-4-alkyl)-aminocarbonyl, cyclo-C3-6-alkyl-amino-carbonyl, cyclo-C3-6-alkyleneimino-carbonyl, cyclo-C3-6-alkyleneimino-C2-4-alkyl-aminocarbonyl, C1-4-alkyl-sulphonyl, C1-4-alkyl-sulphinyl, C1-4-alkyl-sulphonylamino, amino, C1-4-alkylamino, di-(C1-4-alkyl)-amino, C1-4-alkyl-carbonyl-amino, cyclo-C3-6-alkyleneimino, phenyl-C1-3-alkylamino, N-(C1-4-alkyl)-phenyl-C1-3-alkylamino, acetylamino, propionylamino, phenylcarbonyl, phenylcarbonylamino, phenylcarbonylmethyl-amino, hydroxy-C2-3-alkylaminocarbonyl, (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 above-mentioned groups and residues, particularly in A, B, W, X, Y, Z, R1 to R5 and R10 to R22, in each case one or more C atoms may additionally be mono- or polysubstituted by F and/or in each case one or two C atoms independently of one another may additionally be monosubstituted by Cl or Br and/or in each case one or more phenyl rings independently of one another additionally have one, two or three substituents selected from among F, Cl, Br, I, cyano, C1-4-alkyl, C1-4-alkoxy, difluoromethyl, trifluoromethyl, hydroxy, amino, C1-3-alkylamino, di-(C1-3-alkyl)-amino, acetylamino, aminocarbonyl, difluoromethoxy, trifluoromethoxy, amino-C1-3-alkyl, C1-3-alkylamino-C1-3-alkyl- and di-(C1-3-alkyl)-amino-C1-3-alkyl-and/or may be monosubstituted by nitro, and the H atom of any carboxy group present or an H atom bound to an N atom may each be replaced by a group which can be cleaved in vivo, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
2. Alkyne compounds according to claim 1, characterised in that R1, R2 independently of one another denote H, a C1-8-alkyl or C3-7-cycloalkyl group optionally substituted by the group R11 or a phenyl group optionally mono- or polysubstituted by the group R12 and/or monosubstituted by nitro, or R1 and R2 form a C2-8-alkylene bridge, wherein - one or two -CH2- groups independently of one another may be replaced by -CH=N- or -CH=CH- and/or - one or two -CH2- groups independently of one another may be replaced by -O-, -S-, -CO-, -C(=CH2)- or -NR13- in such a way that heteroatoms are not directly joined together, while in the alkylene bridge defined hereinbefore one or more H
atoms may be replaced by R14, and the alkylene bridge defined hereinbefore may be substituted by one or two identical or different carbo- or heterocyclic groups Cy in such a way that the bond betwen the alkylene bridge and the group Cy is made - via a single or double bond, - via a common C atom forming a spirocyclic ring system, - via two common adjacent C- and/or N atoms forming a fused bicyclic ring system or - via three or more C- and/or N atoms forming a bridged ring system, X denotes a single bond or a C1-6-alkylene bridge, wherein - a -CH2- group may be replaced by -CH=CH- or -C.ident.C- and/or - one or two -CH2- groups independently of one another may be replaced by -O-, -S-, -(SO)-, -(SO2)-, -CO- or -NR4- in such a way that in each case two O, S or N atoms or an O
and an S atom are not directly joined together, while the bridge X may be attached to R1 including the N atom attached to R1 and X, forming a heterocyclic group, and while two C atoms or a C and an N atom of the alkylene bridge may be joined together by an additional C1-4-alkylene bridge, and a C atom may be substituted by R10 and/or one or two C atoms in each case may be substituted by one or two identical or different C1-6-alkyl groups, and W, Z independently of one another denote a single bond or a C1-4-alkylene bridge, while in the group W and/or Z a -CH2- group not adjacent to the -C.ident.C- group may be replaced by -O- or -NR5-, and two adjacent C atoms or a C atom and an adjacent N atom may be joined together by an additional C1-4-alkylene bridge, and in the alkylene bridge and/or in the additional alkylene bridge a C atom may be substituted by R10 and/or one or two C atoms independently of one another may be substituted by one or two identical or different C1-6-alkyl groups, and B has one of the meanings given for Cy or denotes 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 fluorine and cyclic groups may be mono- or polysubstituted by R20, R10 denotes hydroxy, .omega.-hydroxy-C1-3-alkyl, C1-4-alkoxy, .omega.-(C1-4-alkoxy)-C1-3-alkyl, amino, C1-4-alkyl-amino, di-(C1-4-alkyl)-amino, cyclo-C3-6-alkyleneimino, amino-C1-3-alkyl, C1-4-alkyl-amino-C1-3-alkyl, di-(C1-4-alkyl)-amino-C1-3-alkyl, cyclo-C3-6-alkyleneimino-C1-3-alkyl, amino-C2-3-alkoxy, C1-4-alkyl-amino-C2-3-alkoxy, di-(C1-4-alkyl)-amino-C2-3-alkoxy or cyclo-C3-6-alkyleneimino-C2-3-alkoxy, R13 has one of the meanings given for R17, R14 denotes halogen, C1-6-alkyl, R15-O, R15-O-CO, R15-CO, R15-CO-O, R16R17N, R18R19N-CO, R15-O-C1-3-alkyl, R15-O-CO-C1-3-alkyl, R15-CO-C1-3-alkyl, R15-CO-O-C1-3-alkyl, R16R"N-C1-3-alkyl, R18R19N-CO-C1-3-alkyl or Cy-C1-3-alkyl, 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, C1-4-alkylcarbonyl, hydroxycarbonyl-C1-3-alkyl, C1-4-alkylcarbonylamino-C2-3-alkyl, N-(C1-4-alkylcarbonyl)-N-(C1-4-alkyl)-amino-C2-3-alkyl, C1-4-alkylsulphonyl, C1-4-alkylsulphonylamino-C2-3-alkyl or N-(C1-4-alkylsulphonyl)-N(-C1-4-alkyl)-amino-C2-3-alkyl R20 denotes halogen, hydroxy, cyano, C1-6-alkyl, C3-7-cycloalkyl, C3-7-cycloalkyl- C1-3-alkyl, hydroxy-C1-3-alkyl, R22-C1-3-alkyl or has one of the meanings given for R22, R22 denotes phenyl, phenyl-C1-3-alkoxy, C1-4-alkoxy, C1-4-alkylthio, carboxy, C1-4-alkylcarbonyl, C1-4-alkoxycarbonyl, aminocarbonyl, C1-4-alkylaminocarbonyl, di-(C1-4-alkyl)-aminocarbonyl, cyclo-C3-6-alkyleneimino-carbonyl, C1-4-alkyl-sulphonyl, C1-4-alkyl-sulphinyl, C1-4-alkyl-sulphonylamino, amino, C1-4-alkylamino, di-(C1-4-alkyl)-amino, cyclo-C3-6-alkyleneimino, phenyl-C1-3-alkylamino, N-(C1-4-alkyl)-phenyl-C1-3-alkylamino, acetylamino, propionylamino, phenylcarbonyl, phenylcarbonylamino, phenylcarbonylmethylamino, hydroxy-alkylaminocarbonyl, (4-morpholinyl)carbonyl, (1-pyrrolidinyl)-carbonyl, (1-piperidinyl)carbonyl, (hexahydro-1-azepinyl)carbonyl, (4-methyl-1-piperazinyl)carbonyl, methylenedioxy, aminocarbonylamino or alkylaminocarbonylamino, while R4, R11, R12, R16, R18, R19 and Cy are defined as in claim 1.
3. Alkyne compounds according to claim 1 or 2, characterised in that R1, R2 independently of one another represent H, C1-6-alkyl, C3-7 cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, .omega.-hydroxy-C2-3-alkyl, .omega.-(C1-4-alkoxy)-C2-3-alkyl, C1-4-alkoxy-carbonyl-C1-4-alkyl, carboxyl-C1-4-alkyl, amino-C2-4-alkyl, C1-4-alkyl-amino-C2-4-alkyl, di-(C1-4-alkyl)-amino-C2-4-alkyl, cyclo-C3-6-alkyleneimino-C2-4-alkyl, pyrrolidin-3-yl, N-(C1-4-alkyl)-pyrrolidinyl, pyrrolidinyl-C1-3-alkyl, N-(C1-4-alkyl)-pyrrolidinyl-C1-3-alkyl, piperidinyl, N-(C1-4-alkyl)-piperidinyl, piperidinyl-C1-3-alkyl, N-(C1-4-alkyl)-piperidinyl-C1-3-alkyl, phenyl, phenyl-C1-3-alkyl, pyridyl or pyridyl-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 may be monosubstituted independently of one another by Cl or Br, and the phenyl or pyridyl group may be mono- or polysubstituted by the group R12 defined in claim 1 and/or may be monosubstituted by nitro.
4. Alkyne compounds according to one or more of claims 1 to 3, characterised in that R1 and R2 form an alkylene bridge according to claim 1 in such a way that R1R2N- denotes 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-azepine, 2,3,6,7-tetrahydro-1H-azepine, piperazine, wherein the free imine function may be substituted by R13, piperidin-4-one-oxime, piperidin-4-one-O-C1-4-alkyl-oxime, morpholine and thiomorpholine, while according to claim 1 one or more H atoms may be replaced by R14, and/ or the alkylene bridge may be substituted by one or two identical or different carbo- or heterocyclic groups Cy in a manner specified in claim 1 , while R13, R14 and Cy are defined as in claim 1 or 2.
5. Alkyne compounds according to one or more of the preceding claims , characterised in that the group is defined according to one of the following partial formulae wherein one or more H atoms of the heterocycle formed by the group R1R2N- may be replaced by R14 and the ring attached to the heterocycle formed by the group R1R2N- may be mono- or polysubstituted by R20 at one or more C atoms, in the case of a phenyl ring may also additionally be monosubstituted by nitro and X', X" independently of one another denote a single bond or C1-3-alkylene and in the event that the group Y is linked to X' or X" via a C atom, also denote -C1-3-alkylene-O-, -C1-3-alkylene-NH- or -C1-3-alkylene-N(C1-3-alkyl)-, and X" additionally also denotes -O-C1-3-alkylene-, -NH-C1-3-alkylene- or -N(C1-3-alkyl)-C1-3-alkylene- and in the event that the group Y is linked to X" via a C atom, also denotes -NH-, -N(C1-3-alkyl)- or -O-, while in the meanings given for X', X" hereinbefore, in each case a C atom may be substituted by R10, preferably by a hydroxy, .omega.-hydroxy-C1-3-alkyl, .omega.-(C1-4-alkoxy)-C1-3-alkyl and/or C1-4-alkoxy group, and/or one or two C atoms in each case may be substituted by one or two identical or different substituents selected from C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, C4-7-cycloalkenyl and C4-7-cycloalkenyl-C1-3-alkyl, while two alkyl and/or alkenyl substituents may be joined together, forming a carbocyclic ring system, and in X', X" independently of one another 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 wherein R2, R10, R13, R14, R20, R21 and X have the meanings given in claim 1 or 2.
6. Alkyne compounds according to one or more of the preceding claims, characterised in that X denotes a single bond or C1-4-alkylene and in the event that the group Y is linked to X via a C atom, it also denotes -CH2-CH=CH-, -CH2-C.ident.C-, C2-4-alkylenoxy, C2-4-alkylene-NR4, C2-4-alkylene-NR4-C2-4-alkylene-O, 1,2- or 1,3-pyrrolidinylene or 1,2-, 1,3- or 1,4-piperidinylene, while the pyrrolidinylene and piperidinylene groups are bound to Y via the imino group, while the bridge X may be attached to R1 including the N atom attached to R1 and X, forming a heterocyclic group, and the bridge X
may additionally also be attached to R2 , including the N atom attached to R2 and X , forming a heterocyclic group , and in X a C atom may be substituted by R10, and/or one or two C atoms in each case may be substituted by one or two identical or different substituents selected from C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, C4-7-cycloalkenyl and C4-7-cycloalkenyl-C1-3-alkyl, while two alkyl and/or alkenyl substituents may be joined together, forming a carbocyclic ring system, and 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 R1, R4 and R10 are defined as in claim 1 or 2.
7. Alkyne compounds according to claim 6, characterised in that X
denotes -CH2-, -CH2-CH2- or -CH2-CH2-CH2- and in the event that the group Y is bonded to X via a C atom, it also denotes -CH2-C.ident.C- -CH2-CH2-O-, -CH2-CH2-NR4- or 1,3-pyrrolidinylene, while the pyrrolidinylene group is linked to Y via the imino group, and the bridge X may be attached to R1 including the N atom attached to R1 and X, forming a heterocyclic group, and the bridge X may additionally also be attached to R2 , including the N atom attached to R2 and X , forming a heterocyclic group, and in X a C atom may be substituted by R10, preferably a hydroxy, .omega.-hydroxy-C1-3-alkyl, .omega.-(C1-4-alkoxy)-C1-3-alkyl and/or C1-4-alkoxy group, and/or one or two C atoms in each case may be substituted by one or two identical or different substituents selected from C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, C3-7-cycloalkyl-C1-3-alkyl, C4-7-cycloalkenyl and C4-7-cycloalkenyl-C1-3-alkyl, while two alkyl and/or alkenyl substituents may be joined together, forming a carbocyclic ring system, 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 wherein R1, R4 and R10 have one of the meanings given in claim 1 or 2.
8. Alkyne compounds according to one or more of the preceding claims, characterised in that W and/or Z independently of one another may denote a single bond, -CH2-, -CH2-CH2-, -CH2-CH2-CH2- or cyclopropylene and W may additionally also represent -CH2-O-, -CH2-CH2-O-, -CH2-NR4-or -CH2-CH2-NR4- and Z may additionally also represent -O-CH2-, -O-CH2-CH2-, -NR4-CH2-or -NR4-CH2-CH2-, wherein a C atom may be substituted by R10, preferably by a hydroxy, .omega.-hydroxy-C1-3-alkyl, .omega.-(C1-4-alkoxy)-C1-3-alkyl- and/or alkoxy group, and/or one or two C atoms independently of one another may each be substituted by 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 may be monosubstituted independently of one another by Cl or Br and wherein R4 and R10 have one of the meanings given in claim 1.
9. Alkyne compounds according to claim 8, characterised in that W
and/or Z independently of one another denote a single bond or are selected from among the bridges -CH2-, -CH2-CH2-, -CH2-CH(CH3)-, -CH2-C(CH3)2-, -CH(CH3)-CH2-, -C(CH3)2-CH2-, cyclopropylene, -CH2-CH(R10)-, -CH(R10)-CH2- and W may additionally also represent -CH2-O- or -CH2-NR4- and Z may additionally also represent -O-CH2- or -NR4-CH2-, wherein R4 has the meanings given in claim 1, preferably -H, methyl, 345~

ethyl or propyl, and wherein R10 has the meanings given in claim 1, preferably -OH, N-pyrrolidinyl, amino-ethoxy, C1-4-alkyl-amino-ethoxy, di-(C1-4-alkyl)-amino-ethoxy, 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 may be monosubstituted independently of one another by Cl or Br.
10. Alkyne compounds according to one or more of the preceding claims, characterised in that the group Y is selected from among the bivalent cyclic groups phenyl, naphthyl, thienyl, benzothienyl, tetrahydronaphthyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, indolyl, dihydroindolyl, dihydroindolonyl, quinolinyl, tetrahydroquinolinyl, isoquinolinyl, tetrahydro-isoquinolinyl, indazolyl, benzimidazolyl, benzofuranyl or benzoxazolyl, while the above-mentioned cyclic groups may be mono- or polysubstituted at one or more C atoms by R20, and in the case of a phenyl group may also additionally be monosubstituted by nitro, and/or may be substituted by R21 at one or more N atoms, while R1 may be attached to Y and/or X may be attached to Y as specified in claim 1, and X, R1, R20 and R21 have the meanings specified in claim 1 or 2.
11. Alkyne compounds according to one or more of the preceding claims, characterised in that the group Y is selected from among the bivalent cyclic groups while the above-mentioned cyclic groups may be mono- or polysubstituted by R20 at one or more C atoms, and in the case of a phenyl group may also additionally be monosubstituted by nitro, and/or one or more NH groups may be substituted by R21, wherein R20 and R21 are defined as in claim 1 or 2.
12. Alkyne compounds according to one or more of the preceding claims, characterised in that the group A is selected from among the bivalent cyclic groups phenyl, pyridinyl, pyrimidinyl, pyrazinyl or pyridazinyl, while the above-mentioned cyclic groups may be mono- or polysubstituted at one or more C atoms by R20, and in the case of a phenyl ring may also additionally be monosubstituted by nitro, and/or one or more NH groups may be substituted by R21, and R20 and R21 are defined as in claim 1 or 2.
13. Alkyne compounds according to one or more of the preceding claims, characterised in that the group B is selected from the first group comprising phenyl, thienyl and furanyl or from the second group comprising 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, C3-7-cycloalkyl-C1-3-alkynyl, wherein one or more C
atoms may be mono- or polysubstituted by fluorine, and the above-mentioned cyclic groups may be mono- or polysubstituted by R20 at one or more C atoms, and in the case of a phenyl group may also additionally be monosubstituted by nitro, and R20 is defined as in claim 1 or 2.
14. Alkyne compounds according to one or more of the preceding claims, characterised in that Y has a meaning according to claim 11, and preferably denotes a group selected from A has a meaning according to claim 12, and preferably denotes B has a meaning according to claim 13 , and preferably denotes phenyl, while A, B and/or Y may be mono- or disubstituted, B may also be trisubstituted, by R20 at one or more C atoms, and in the case of a phenyl ring may also additionally be monosubstituted by nitro, and an -NH group may be substituted by R21, and R20 and R21 are defined as in claim 1 or 2.
15. Alkyne compounds according to claim 1 or 2, characterised in that A, B and Y independently of one another are defined as in claim 14 and R1,R2 and X are defined as in claim 3, 4 and/or 6, particularly as in claim 3, 5 and 7, and W and Z independently of one another are defined according to claim 8, particularly claim 9.
16. Alkyne compounds according to one or more of the preceding claims, characterised in that R20 denotes F, CI, Br, I, OH, cyano, methyl, difluoromethyl, trifluoromethyl, ethyl, n-propyl, iso-propyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, n-propoxy or iso-propoxy, while any substituents R20 occurring repeatedly may have identical or different meanings.
17. Alkyne compounds according to claim 1 selected from the formulae (1) 5-(4-chloro-phenyl)-2-[5-(2-pyrrolidin-1-yl-ethoxy)-pyridin-2-yl-ethynyl]-pyridine (2) [(R)-1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-pyrrolidin-2-yl]-methanol (3) 5-(4-chloro-phenyl)-2-[2-(4-methyl-piperidin-1-ylmethyl)-benzofuran-5-ylethynyl]-pyridine (4) 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-1-(2-pyrrolidin-1-yl-ethyl)-1,3-dihydro-benzimidazol-2-one (5) [1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-piperidin-4-yl]-methanol (6) 1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-piperidin-3-ol (7) N-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenyl}-2-pyrrolidin-1-yl-propionamide (8) 1-{3-[5-(4-chloro-phenyl)-pyridin-2-yl]-prop-2-ynyl}-5-pyrrolidin-1-ylmethyl-1H-indole (9) 2-[4-(4-azetidin-1-ylmethyl-phenyl)-but-1-ynyl]-5-(4-chloro-phenyl)-pyridine (10) 5-(4-chloro-phenyl)-2-[4-(4-piperidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine (11) 5-(4-bromo-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine (12) 2-[(4-{4-[5-(4-chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-benzyl)-methyl-amino]-ethanol (13) 5-(4-chloro-phenyl)-2-{4-[4-((S)-2-methoxymethyl- pyrrolidin-1-ylmethyl)-phenyl]-but-1-ynyl}-pyridine (14) 5-(4-chloro-phenyl)-2-{4-[2-(4-propyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-pyridine (15) 5'-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-3-pyrrolidin-1-yl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl (16) 5-(4-chloro-phenyl)-2-{4-[4-(2-methyl-pyrrolidin-1-ylmethyl)-phenyl]-but-1-ynyl}-pyridine (17) 3-(4-chloro-phenyl)-6-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridazine (18) 5-(4-chloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine (19) 5-(4-chloro-phenyl)-2-{4-[2-(2,6-dimethyl-piperidin-1-yl)-ethoxy]-3-methyl-phenylethynyl}-pyridine (20) methyl 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-(2-pyrrolidin-1-yl-ethoxy)-benzoate (21) 5-(4-chloro-phenyl)-2-[3-methyl-4-(2-piperidin-1-yl-ethoxy)-phenylethynyl]-pyridine (22) 5-(4-chloro-phenyl)-2-[3-methyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine (23) 5-(4-chloro-phenyl)-2-{4-[4-(4-methyl-piperidin-1-ylmethyl)-phenyl]-but-1-ynyl}-pyridine (24) 1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-piperidin-4-ol (25) 5-(4-chloro-phenyl)-2-{3-methyl-4-[2-(2-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-pyridine (26) {5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-pyridin-2-yl}-(2-piperidin-1-yl-ethyl)-amine (27) 4-(4-{4-[5-(4-chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-benzyl)-morpholine (28) (4-{4-[5-(4-chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-benzyl)-methyl-piperidin-4-yl-amine (29) 5-(4-chloro-phenyl)-2-[3-(4-pyrrolidin-1-ylmethyl-phenoxy)-prop-1-ynyl]-pyridine (30) 6-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline (31) (1-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-pyridin-2-yl}-pyrrolidin-yl)-dimethyl-amine (32) [(S)-1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-pyrrolidin-2-yl]-methanol (33) 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-(2-pyrrolidin-1-yl-ethoxy)-phenylamine (34) {5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-pyridin-2-yl}-(2-pyrrolidin-yl-propyl)-amine (35) 1-(4-{4-[5-(4-chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-benzyl)-pyrrolidin-3-ylamine (36) 2-[3-bromo-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-5-(4-chloro-phenyl)-pyridine (37) 1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-azepan (38) 5-(4-chloro-phenyl)-2-(6-pyrrolidin-1-ylmethyl-naphthalen-2-ylethynyl)-pyridine (39) 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-N-methyl-2-(2-pyrrolidin-1-yl-ethoxy)-benzamide (40) (2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-cyclopropylmethyl-propyl-amine (41) 1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-4-methyl-piperidin-4-ol (42) 5-(4-chloro-phenyl)-2-{3-methyl-4-[2-(4-methyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-pyridine (43) 5-(4-chloro-phenyl)-3-fluoro-2-{4-[2-(4-methyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-pyridine (44) 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-1-(2-pyrrolidin-1-yl-ethyl)-indole (45) {4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenyl}-(2-pyrrolidin-1-yl-ethyl)-amine (46) methyl [1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-piperidin-4-yl]-acetate (47) {5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-pyridin-2-yl}-methyl-(2-pyrrolidin-1-yl-ethyl)-amine (48) tert-butyl [1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-pyrrolidin-3-yl]-carbaminate (49) 5-(4-chloro-phenyl)-2-[3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine (50) 5-(4-chloro-phenyl)-2-[4-(2-piperidin-1-yl-ethoxy)-phenylethynyl]-pyridine (51) 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-1-(2-pyrrolidin-1-yl-ethyl)-indazole (52) 2-[4-(2-azetidin-1-yl-ethoxy)-phenylethynyl]-5-(4-chloro-phenyl)-pyridine (53) 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde O-methyl-oxime (54) 1'-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-pyridin-2-yl}-[1,3']bipyrrolidinyl (55) (4-{4-[5-(4-chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-benzyl)-methyl-(1-methyl-piperidin-4-yl)-amine (56) 5-(4-chloro-phenyl)-2-[3-chloro-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine (57) (S)-1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-pyrrolidin-3-ol (58) [1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-piperidin-4-yl]-pyridin-2-yl-amine (59) 5-(4-bromo-phenyl)-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine (60) N-[1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-piperidin-4-ylmethyl]-N-methyl-acetamide (61) 5-(2,4-dichloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine (62) 5-(4-chloro-phenyl)-2-{4-[2-(4-ethyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-pyridine (63) [1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-piperidin-4-yl]-methanol (64) 5-(4-chloro-phenyl)-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine (65) 5-(4-chloro-phenyl)-2-{4-[2-(3,6-dihydro-2H-pyridine-1-yl)-ethoxy]-phenylethynyl}-pyridine (66) 5-(4-chloro-phenyl)-2-{4-[2-(2-methyl-pyrrolidin-1-yl)-ethoxy]-phenylethynyl}-pyridine (67) (4-{4-[5-(4-chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-benzyl)-cyclopropylmethyl-amine (68) 5-(4-chloro-phenyl)-2-{4-[4-(4-pyrrolidin-1-yl-piperidin-1-ylmethyl)-phenyl]-but-1-ynyl}-pyridine (69) 5-(4-methoxy-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine (70) 5-(3,4-difluoro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine (71) 1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-4-methyl-piperidin-4-ol (72) 5-(4-chloro-phenyl)-2-{4-[4-((R)-2-methoxymethyl-pyrrolidin-1-ylmethyl)-phenyl]-but-1-ynyl}-pyridine (73) 6-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-pyrrolidin-1-ylmethyl-quinoline (74) 1-(4-{4-[5-(4-chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-benzyl)-4-methyl-piperazine (75) {5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-pyridin-2-yl}-(2-pyrrolidin-yl-ethyl)-amine (76) 5-(4-chloro-phenyl)-2-(3-methyl-4-{2-[4-(pyridin-2-yloxy)-piperidin-1-yl]-ethoxy}-phenylethynyl)-pyridine (77) 5-(4-chloro-phenyl)-2-{4-[2-(3,6-dihydro-2H-pyridine-1-yl)-ethoxy]-3-methyl-phenylethynyl}-pyridine (78) (R)-1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-pyrrolidin-3-ol (79) 1-(2-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl)-piperidin-4-ol (80) ~1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-piperidin-4-ol (81 ) ~1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl)-2-methyl-phenoxy}-ethyl)-4-phenyl-piperidin-4-ol (82) ~1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl)-phenoxy}-ethyl)-[4,4']bipiperidinyl (83) ~5-(4-chloro-phenyl)-2-[3-ethynyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl)-pyridine (84) ~5-(3,4-dichloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine (85) ~1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-4-methyl-piperidin-4-ylamine (86) ~5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde-oxime (87) ~5-(4-chloro-phenyl)-2-{4-[2-(2,6-dimethyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-pyridine (88) ~5-(4-chloro-phenyl)-2-(4-{2-[4-(1H-imidazol-4-yl)-piperidin-1-yl]-ethoxy}-3-methyl-phenylethynyl)-pyridine (89) ~[1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-piperidin-2-yl]-methanol (90) ~(4-{4-[5-(4-chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-benzyl)-methyl-pyridin-2-ylmethyl-amine (91) ~1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-piperidin-4-carboxylic acid amide (92) ~2-[(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-methyl-amino]-ethanol (93) ~5-(4-chloro-phenyl)-2-{4-[2-(4-methyl-piperidin-1-yl)-ethoxy]-phenylethynyl}-pyridine (94) ~{2-[1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-piperidin-4-yl)-ethyl}-diethyl-amine (95) ~5-(4-chloro-phenyl)-2-{4-[2-(2,4,6-trimethyl-piperidin-1-yl)-ethoxy)-phenylethynyl}-pyridine 357~

(96) ~5-(4-chloro-phenyl)-2-{4-[2-(3,5-dimethyl-piperidin-1-yl)-ethoxy]-3-methyl-phenylethynyl}-pyridine (97) ~cis-2-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-decahydro-isoquinoline (98) ~6-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-2-methyl-2,6-diaza-spiro[3.4]octane (99) ~1-(2-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl)-4-methyl-piperidin-4-ol (100) ~[1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-pyrrolidin-3-yl]-dimethyl-amine (101) ~5-(4-chloro-phenyl)-2-[3-fluoro-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine (102) ~[1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-piperidin-4-yl]-cyclopentyl-methyl-amine (103) ~5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-1-(2-pyrrolidin-1-yl-ethyl)-2,3-dihydro-1H-indole (104) ~5-(4-chloro-phenyl)-2-{4-[2-(4-pyrrolidin-1-yl-piperidin-1-yl)-ethoxy]-phenylethynyl}-pyridine (105) ~5-(4-chloro-phenyl)-2-{4-[2-(2,5-dihydro-pyrrol-1-yl)-ethoxy]-phenylethynyl}-pyridine (106) ~[1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-piperidin-4-ylmethyl]-dimethyl-amine (107) ~1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-4-methyl-piperazine (108) ~(4-{4-[5-(4-chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-benzyl)-pyridin-2-ylmethyl-amine (109) ~1-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-spiro[piperidin-4,2'(1H')-quinazoline]-4'(3'H)one (110) ~4-{[(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-methyl-amino]-methyl}-phenol (111)~5-(4-chloro-phenyl)-2-[4-(3-piperidin-1-yl-pyrrolidin-1-yl)-phenylethynyl]-pyridine (112) ~5-(4-chloro-phenyl)-2-[2-(2-pyrrolidin-1-yl-ethoxy)-pyridin-5-yl-ethynyl]-pyridine (113) ~3-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-9-methyl-3,9-diaza-spiro[5.5]undecane (114) ~(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl)-diisopropyl-amine (115) ~5-(4-chloro-phenyl)-2-[4-(3-pyrrolidin-1-yl-propyl)-phenylethynyl]-pyridine (116) ~2-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-1,2,3,4-tetrahydro-isoquinoline (117) ~3-(4-chloro-phenyl)-6-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridazine (118) ~(R)-1-(2-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethyl)-pyrrolidin-3-ol (119) ~5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-1,3-dihydro-benzimidazol-2-one (120) ~5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-1-(2-pyrrolidin-1-yl-ethyl)-benzimidazole (121) ~2-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-1-methyl-5-pyrrolidin-1-ylmethyl-1H-benzimidazole (122) ~trans-2-(2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-phenoxy}-ethyl)-decahydro-isoquinoline including the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof.
18. Physiologically acceptable salts of the alkyne compounds according to one or more of claims 1 to 17.
19. Composition, containing at least one alkyne compound according to one or more of claims 1 to 17 and/ or a salt according to claim 18 optionally together with one or more inert carriers and/or diluents.
20. Pharmaceutical compositions, containing at least one alkyne compound according to one or more of claims 1 to 17 and/ or a salt according to claim 18 optionally together with one or more inert carriers and/or diluents.
21. Use of at least one alkyne compound according to one or more of claims 1 to 17 and/ or a salt according to claim 18 for influencing the eating behaviour of a mammal.
22. Use of at least one alkyne compound according to one or more of claims 1 to 17 and/ or a salt according to claim 18 for reducing the body weight and/ or for preventing an increase in the body weight of a mammal.
23. Use of at least one alkyne compound according to one or more of claims 1 to 17 and/ or a salt according to claim 18 for preparing a pharmaceutical composition with an MCH receptor-antagonistic activity.
24. Use of at least one alkyne compound according to one or more of claims 1 to 17 and/ or a salt according to claim 18 for preparing a pharmaceutical composition which is suitable for the prevention and/or treatment of symptoms and/or diseases caused by MCH or causally connected with MCH in some other way.
25. Use of at least one alkyne compound according to one or more of claims 1 to 17 and/ or a salt according to claim 18 for preparing a pharmaceutical composition which is suitable for the prevention and/or treatment of metabolic disorders and/or eating disorders, particularly obesity, bulimia, bulimia nervosa, cachexia, anorexia, anorexia nervosa and hyperphagia.
26. Use of at least one alkyne compound according to one or more of claims 1 to 17 and/ or a salt according to claim 18 for preparing a pharmaceutical composition which is suitable for the prevention and/or treatment of illnesses and/or disorders which accompany 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.
27. Use of at least one alkyne compound according to one or more of claims 1 to 17 and/ or a salt according to claim 18 for preparing a pharmaceutical composition which is suitable for the prevention and/or treatment of 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.
28. Use of at least one alkyne compound according to one or more of claims 1 to 17 and/ or a salt according to claim 18 for preparing a pharmaceutical composition which is suitable for the prevention and/or treatment of urinary problems, such as for example urinary incontinence, overactive bladder, urgency, nycturia and enuresis.
29. Process for preparing a composition or a pharmaceutical composition according to one or more of claims 19 to 28, characterised in that at least one alkyne compound according to one or more of claims 1 to 17 and/ or a salt according to claim 18 is incorporated in one or more inert carriers and/or diluents by a non-chemical method.
30. Pharmaceutical compositions, containing a first active substance selected from the alkyne compounds according to one or more of claims 1 to 17 and/ or a salt according to claim 18 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.
31. Process for preparing alkyne compounds of formula A.5 R1R2N-X-Y-C=C-W-A-B (A.5) wherein in formulae A.1, A.2, A.3, A.4 and A.5 R1, R2, X, Y, W, A and B have one of the meanings given in claims 1 to 17 and Y denotes aryl or heteroaryl according to claim 1 or 2, wherein a halogen compound of formula A.1 HO-X-Y-Hal (A.1) wherein Hal denotes chlorine, bromine or iodine, preferably bromine or iodine, is reacted with an alkyne compound of formula A.2 H-C=C-W-A-B (A.2) in the presence of a suitable palladium catalyst, a suitable base and copper(I)iodide in a suitable solvent, and the resulting compound of formula A.3 HO-X-Y-C.ident.C-W-A-B (A.3) is reacted with methanesulphonic acid chloride (MsCI) to form the methanesulphonate derivative A.4, MsO-X-Y-C=C-W-A-B (A.4) which is further reacted with an amine of formula H-NR1R2 to obtain the end product A.5.
32. Process for preparing alkyne compounds of formula B.5 R1R2N-X-Y-Z-C=C-A-B (B.5) wherein in formulae B.1, B.2, B.3, B.4 and B.5 R1, R2, X, Y, Z, A and B have one of the meanings given in claims 1 to 17 and A denotes aryl or heteroaryl according to claim 1 or 2, wherein a halogen compound of formula B.1 Hal-A-B (B.1) wherein Hal denotes chlorine, bromine or iodine, preferably bromine or iodine, is reacted with an alkyne compound of formula A.2 HO-X-Y-Z-C=C-H (B.2) in the presence of a suitable palladium catalyst, a suitable base and copper(I)iodide in a suitable solvent, and the resulting compound of formula B.3 HO-X-Y-Z-C.ident.C-A-B (B.3) is reacted with methanesulphonic acid chloride (MsCl) to form the methanesulphonate derivative B.4, MsO-X-Y-Z-C=C-A-B (B.4) which is further reacted with an amine of formula H-NR1R2 to obtain the end product B.5.
33. Process for preparing alkyne compounds of formula C.3 R1R2N-X-Y-C.ident.C-W-A-B (C.3) wherein in formulae C.1, C.2 and C.3 R1, R2, X, Y, W, A and B have one of the meanings given in claims 1 to 17 and Y optionally denotes substituted aryl or heteroaryl according to claim 1 or 2, wherein a halogen compound of formula C.1 R1R2N-X-Y-Hal (C.1) wherein Hal denotes chlorine, bromine or iodine, preferably bromine or iodine, is further reacted with an alkyne compound of formula C.2 H-C.ident.C-W-A-B (C.2) in the presence of a suitable palladium catalyst, a suitable base and copper(I)iodide in a suitable solvent to obtain the end product C.3.
34. Process for preparing alkyne compounds of formula D.3 R1R2N-X-Y-Z-C=C-A-B (D.3) wherein in formulae D.1, D.2 and D.3 R1, R2, X, Y, Z, A and B have one of the meanings given in claims 1 to 17 and A denotes optionally substituted aryl or heteroaryl according to claim 1 or 2, wherein a halogen compound of formula D.2 Hal-A-B (D.2) wherein Hal denotes chlorine, bromine or iodine, preferably bromine or iodine, is reacted with an alkyne compound of formula D.1 R1R2N-X-Y-Z-C=C-H (D.1) in the presence of a suitable palladium catalyst, a suitable base and copper(I)iodide in a suitable solvent to obtain the end product D.3.
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