Guanidine compounds, and use thereof as binding partners for 5-ht5 receptors

Guanidine compound of the general formula 1

• corresponding enantiomeric, diastereomeric and/or tautomeric forms thereof as well as pharmaceutically acceptable salts thereof, wherein the given moieties have the following definitions:
• W:
• a moiety of the general formula W1 or W2
• wherein
• A:
• NO2, NH2, OH, CN, CF3, OCF3, CHF2, OCHF2, COOH, O—CH2—COOH, halogen, SH, or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-hetaryl or C1-C4-alkylene-aryl, or
• O—RA1, CO—RA′, S—RA′, SO—RA′, CO—O—RA′, NRA4—OO—O—RA′, O—CH2—OOO—RA1, NRA2RA3, CO—NH2, SO2NH2, NRA4—CO—RA1, SO2—RA′, NRA4—SO2—RA1, SO2—NRA2RA3 or CO—NRA2RA3;
• RA1:
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-aryl, C2-C6-alkenylenearyl or C1-C6-alkylene-hetaryl;
• RA2:
• hydrogen, OH, CN, or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, C1-C6-alkylene-O—C1-C6-alkyl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—C1-C4-alkylene-hetaryl;
• RA3:
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-aralkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-aryl, C1-C4alkylene-hetaryl, C1-C6-alkylene-O—C1-C6-alkyl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—C1-C4-alkylene-hetaryl;
• or the moieties RA2 and RA3 form, together with the nitrogen, a 3 to 7-membered, optionally substituted, saturated or aromatic heterocycle, which can contain one, two or three further different or identical heteroatoms from the group O, N, S;
• wherein optionally two of the moieties substituted on this heterocycle can together form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S and wherein the so-formed cycle can be optionally substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• RA4:
• hydrogen, or
• each optionally substituted C1-C6-alkyl, C1-C6-alkylene-O—C1-C6-alkyl, C2-C6-alkenyl, C3-C12-alkynyl, CO—C1-C6-alkyl, CO—O—C1-C6-alkyl, SO2—C1-C6-alkyl, C3-C7-cycloalkyl, aryl, C1-C4-alkylene-aryl, CO—O-arylalkyl, CO—C1-C4-alkylene-aryl, CO-aryl, SO2-aryl, hetaryl, CO-hetaryl or SO2—C1-C4-alkylene-aryl;
• B:
• hydrogen or as moiety A is defined,
• or each independently of one another, two of the moieties A, B or RA1, together form a 3 to 7-membered, optionally substituted, saturated or unsaturated carbocycle or an optionally substituted, saturated or unsaturated or aromatic heterocycle which can contain one, two or three further different or identical heteroatoms from the group O, N, S;
• wherein optionally two moieties substituted on this carbo- or heterocycle can together form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S and wherein the cycle formed can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• Rw1:
• hydrogen, OH, halogen, NO2, NH2, CN, CF3, CHF2, O—CF3, O—CHF2, or each optionally substituted C1-C6-alkyl, C3-C7-cycloalkyl, C1-C6-alkylene-OC1-C6-alkyl, aryl, hetaryl, O—C1-C6-alkyl, O-aryl, O-benzyl, C1-C6-alkylamino, pyrrolidinyl, piperidinyl, morpholinyl, CO—C1-C6-alkyl, SO2—C1-C6-alkyl, CO-aryl, SO2-aryl, CO—C1-C4-alkylenearyl, SO2—C1-C4-alkylene-aryl, SO-aryl, CO—NH2, CO—NH—C1-C6-alkyl, SO2NH—C1-C6-alkyl, CON—(C1-C6-alkyl)2, SO2N—(C1-C6-alkyl)2, NH—SO2—C1-C6-alkyl or NH—CO—C1-C6-alkyl;
• D:
• as moiety A is defined;
• Z:
• a moiety of the general formula Z1
• with the indices
• a=0-4
• b=0, 1
• c=0-4
• wherein the sum of a, b and c is at least 1 and no more than 5;
• Rz2, Rz3, Rz4 independently of one another:
• hydrogen, halogen, OH, or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylene-C3-C7-cycloalkyl, C3-C7-cycloalkyl, aryl, C1-C4-alkylene-aryl, hetaryl or C1-C4-alkylene-hetaryl, or
• each independently of one another two moieties are Rz1 and Rz2 or Rz3 and Rz4 together form a 3 to 7-membered, optionally substituted, saturated or unsaturated carbo- or heterocycle, wherein the heterocycle can contain up to three heteroatoms from the group O, N, or S;
• Vz:
• —CO—, —CO—NRz5—, —NRz5—OO—, —O—, —S—, —SO—, —SO2—, —SO2—NRz5—, —NR5—SO2—, —CS—, —CS—NRz5—, —NRz5—CS—, —CS—O—, —O—CS—, —CO—O—, —O—CO—, —O—, ethynylene, —C(═CRz6Rz7)—, —CRz6═CRz7—, —NRz5—CO—NRz5—, —NRz5—;
• Rz5, Rz5* independently of one another:
• hydrogen or
• each optionally substituted C1-C6-alkyl, C1-C6-alkylene-O—C1-C6-alkyl, C2-C6-alkenyl, C3-C12-alkynyl, CO—C1-C6-alkyl, CO—O—C1-C6-alkyl, SO2—C1-C6alkyl, C3-C7-cycloalkyl, aryl, C1-C4-alkylene-aryl, CO—O—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-aryl, CO-aryl, SO2-aryl, hetaryl, CO-hetaryl or SO2—C1-C4-alkylene-aryl;
• Rz6, Rz7 independently of one another:
• hydrogen, OH or
• each optionally substituted C1-C6-alkyl, C1-C4-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylene-C3-C7-cycloalkyl, C3-C7-cycloalkyl, aryl, C1-C4-alkylene-aryl, hetaryl or C1-C4-alkylene-hetaryl;
• R1, R2, R3 independently of one another:
• hydrogen, OH, CN, or
• each optionally substituted C1-C6-alkyl, O—C1-C6-alkyl, C1-C6-alkylene-OC1-C6-alkyl, C3-C7cycloalkyl, O—C3-C7-cycloalkyl, aryl, hetaryl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, O-aryl, O—C1-C4-alkylene-aryl, O-hetaryl, O—C1-C4-alkylene-hetaryl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-aryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl, OCO—C1-C6-alkyl, OCO-aryl, OCO-hetaryl, OCO—C1-C4-alkylene-aryl, OCO—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl or SO2—C1-C4-alkylene-aryl, or
• each independently of the third moiety, two moieties of R1, R2 or R3 together form a 5 to 7-membered, optionally substituted, saturated or unsaturated carbocycle or an optionally substituted, saturated or unsaturated heterocycle which can contain one, two or three further different or identical heteroatoms from the group O, N, S, wherein optionally two of the moieties substituted on this carbo- or heterocycle can together form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S and wherein the cycle formed is optionally substituted or a further, optionally substituted cycle is condensed onto this cycle;
• Q:
• a doubly substituted 5-membered hetaryl moiety chosen from Q1 to Q6
• E:
• O, N—RQ1 or S;
• RQ1:
• hydrogen, or
• each optionally substituted C1-C4-alkyl, CO—C1-C4-alkyl, SO2—C1-C4-alkyl, CO—O—C1-C4-alkyl, aryl, C1-C4-alkylene-aryl, CO-aryl, CO-hetaryl, SO2-aryl, SO2-hetaryl, CO—O-aryl, CO—C1-C4-alkylene-aryl, SO2—C1-C4-alkylene-aryl or CO—O—C1-C4-alkylene-aryl;
• R4, R5 each independently of one another a moiety chosen from the groups 1.), 2.), 3.), 4.) or 5.):
• 1.) hydrogen, halogen, CN, CF3, CHF2, or
• each optionally substituted C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C3-C7-cycloalkyl, C1-C6-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, C1-C6-alkylene-O—C1-C6-alkyl, C1-C6-alkylene-O-aryl, COO—C1-C4-alkyl or C1-C4-alkylene-COO—C1-C4-alkyl;
• 2.) Phenyl or naphthyl, which are each substituted with RQ2, RQ3 and RQ4, wherein
• RQ2, RQ3 or RQ4 each independently of one another represent a substituent from the following group:
• hydrogen, NO2, NH2, OH, CN, CF3, CHF2, OCF3, OCHF2, COOH, O—CH2—COOH, SH, halogen, or
• each optionally substituted aryl, hetaryl, heterocycloalkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, C1-C4-alkylene-aryl or C1-aralkylene-hetaryl, or
• O—RQ5, S—RQ5, NRQ7RQ8, CO—ORQ6, NRQ8—CO—O—RQ6, O—CH2—COO—RQ6, NRQ8—CO—RQ6, SO2—Ro6, NRQ8—SO2—RQ6, SO2NH2, CO—NH2, SO2—NRQ7 RQ8 or CO—NRQ7Ra8, or
• two of the moieties RQ2, RQ3 or RQ4 together form a 3 to 7-membered, optionally substituted, saturated, unsaturated or aromatic carbocycle or an optionally substituted, saturated or unsaturated aromatic heterocycle, which can contain up to three further different or identical heteroatoms O, N, S and optionally two moieties substituted on this heterocycle can together form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S and the cycle formed can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• RQ5 each optionally substituted C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, heterocycloalkyl or hetaryl, or
• C1-C6-alkyl, which is optionally substituted with a substituent from the group consisting of halogen, NO2, NH2, OH, CN, CF3, CHF2, OCF3, OCHF2, NH—(C1-C6-alkyl) and N(C1-C6-alkyl)2;
• RQ6 each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl or C1-C6-alkylene-O—C1-C6-alkyl;
• RQ7 hydrogen, OH, CN, or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C6-alkylene-O—C1-C6-alkyl, CO—C1-C6-alkyl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—C1-C4-alkylene-hetaryl;
• RQ8 each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C6-alkylene-O—C1-C6-alkyl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, COC1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—C1-C4-alkylene-hetaryl;
• or the moieties RQ7 and RQ8 form, together with the nitrogen, a 3 to 7-membered, optionally substituted, saturated or aromatic heterocycle which can contain one, two or three further or different identical heteroatoms O, N, S;
• and optionally two moieties substituted on this heterocycle can form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S and the cycle formed can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• 3.) a 5- or 6-membered hetaryl moiety optionally substituted with one or two substituents from the group consisting of:
• 2-pyrrolyl, 3-pyrrolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-pyridazinyl, 4-pyridazinyl, 5-pyridazinyl, 6-pyridazinyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, thiadiazolyl, oxadiazolyl or triazinyl or their anellated derivatives indazolyl, benzothiophenyl, benzofuranyl, indolinyl, benzimidazolyl, benzthiazolyl, benzoxazolyl, chinolinyl and isochinolinyl;
• or
• 2-thienyl or 3-thienyl optionally substituted with one or two substituents, wherein the substituents are chosen from the group consisting of halogen, NO2, NH2, OH, CN, CF3, OCF3, CHF2, O—CHF2, C1-C6-alkyl, O—C1-C6-alkyl, NH—(C1-C6-alkyl), N(C1-C6-alkyl)2, NHCO—C1-C4-alkyl, NHSO2—C1-C4-alkyl and SO2—C1-C4-alkyl;
• 5.) both moieties R4 and R5 together form a 4 to 7-membered, optionally substituted, saturated or unsaturated or aromatic carbocycle or a 5- or 6-membered optionally substituted, saturated or unsaturated or aromatic heterocycle, which can contain up to three further different or identical heteroatoms O, N, S and can be substituted with up to two further moieties, wherein optionally two moieties substituted on this carbo- or heterocycle can form an anellated, saturated, unsaturared or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S and wherein the cycle formed can be optionally substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• 6.) a C5-C18- bi- or tricyclic, saturated hydrocarbon moiety.

The method of a guanidine compound of the general formula 1A

• of the corrersponding enantiomeric, diastereomeric and/or tautomeric forms thereof as well as pharmaceutically acceptable salts thereof
• wherein the given moieties have the following definitions:
• W:
• a moiety of the general formula W1 or W2
• A:
• NO2, NH2, OH, CN, CF3, OCF3, CHF2, OCHF2, COOH, O—CH2—COOH, halogen, SH, or each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl or C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-hetaryl or C1-C4-alkylene-aryl, or
• O—RA1, CO—RA1, S—RA1, SO—RA1, CO—O—RA1, NRA4—CO—O—RA′, O—CH2—OOO—RA1, NRA2RA3, CO—NH2, SO2NH2, NRA4—CO—RA1, SO2—RA1, NRA4—SO2—RA1, SO2—NRA2RA3 or CO—NRA2RA3;
• RA1:
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C-alkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-aryl, C2-C6-alkenylenearyl or C1-C6-alkylene-hetaryl;
• RA2:
• hydrogen, OH, CN, or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, C1-C6-alkylene-O—C1-C6-alkyl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO O C, C6 alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—Ci-C4-alkylene-hetaryl;
• RA3:
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1C4-alkylene-C3-C7-cycloalkyl, C1-C4alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, C1-C6-alkylene-O—C1-C6-alkyl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—C1-Ca-alkylene-hetaryl;
• or the moieties RA2 and RA3 form, together with the nitrogen, a 3 to 7-membered, optionally substituted, saturated or aromatic heterocycle, which can contain one, two or three further different or identical heteroatoms from the group O, N, S;
• wherein optionally two moieties substituted on this heterocycle can together form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms, O, N, S and wherein the so-formed cycle can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• RA4:
• hydrogen, or
• each optionally substituted C1-C6-alkyl, C1-C6-alkylene-O—C1-C6-alkyl, C2-C5-alkenyl, C3-C12-alkynyl, CO—C1-C6-alkyl, CO—O—C1-C6-alkyl, SO2—C1-C6alkyl, C3-C7-cycloalkyl, aryl, C1-C4-alkylene-aryl, CO—O-arylalkyl, CO—C1-C4-alkylene-aryl, CO-aryl, SO2-aryl, hetaryl, CO-hetaryl or SO2—C1-C4-alkylene-aryl;
• B:
• hydrogen or as moiety A is defined,
• or each independently of one another two of the moieties A, B or Rw1 together form a 3 to 7-membered, optionally substituted, saturated or unsaturated carbocycle with an optionally substituted, saturated or unsaturated or aromatic heterocycle which can contain one, two or three further different or identical heteroatoms from the group O, N, S;
• wherein optionally two moieties substituted on this carbo- or heterocycle can form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S and wherein the cycle formed can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• Rw1:
• hydrogen, OH, halogen, NO2, NH2, CN, CF3, CHF2, O—CF3, O—CHF2, or each optionally substituted C1-C6-alkyl, C3-C7-cycloalkyl, C1-C6-alkylene-OC1-C6-alkyl, C1-C6-alkylene-S—C1-C6-alkyl, aryl, hetaryl, O—C1-C6-alkyl, Daryl, O-benzyl, C1-C6-alkylamino, C1-C6-dialkylamino, pyrrolidinyl, piperidinyl, morpholinyl, CO—C1-C6-alkyl, SO2—C1-C6-alkyl, CO-aryl, SO2aryl, CO—C1-C4-alkylene-aryl, SO2—C1-C4-alkylene-aryl, SO-aryl, CO—NH2, CO—NH—C1-C6-alkyl, SO2NH—C1-C6-alkyl, CON(C1-C6-alkyl)2, SO2N(C1-C6-alkyl)2, NH—SO2—C1-C6-alkyl or NH—CO—C1-C6-alkyl;
• D:
• as moiety A is defined;
• Z:
• a moiety of the general formula Z1
• with the indices
• a=0-4
• b=0, 1
• c=0-4
• wherein the sum of a, b and c is no more than 5;
• Rz1, Rz2, Rz3, Rz4 independently of one another:
• hydrogen, halogen, OH, or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylene-C3-C7-cycloalkyl, C3-C7-cycloalkyl, aryl, C1-C4-alkylene-aryl, hetaryl or C1-C4-alkylene-hetaryl, or
• each independently of one another two moieties Rz1 and Rz2 or Rz3 and Rz4 together form a 3 to 7-membered, optionally substituted, saturated or unsaturated carbo- or heterocycle, which can contain up to three heteroatoms from the group O, N or S;
• Vz:
• —CO—, —CO—NRz5—, —NR,5—OO—, —O—, —S—, —SO—, —SO2—, -502—NR,5—, —NR,5—SO2—, —CS—, —CS—NR,5—, —NR,5—CS—, —CS—O—, —O—CS—, —CO—O—, —O—OO—, —O—, ethynylene, —C(═CRz6Rz7)—, —CRz5═CRz7—, —NR,5—CO—NR,5—, —O—OO—NR,5—, —NR,5—;
• Rz5, Rz5* independently of one another:
• hydrogen, or
• each optionally substituted C1-C6-alkyl, C1-C6-alkylene-O—C1-C6-alkyl, C2-C6-alkenyl, C3-C12-alkynyl, CO—C1-C6-alkyl, CO—O—C1-C6-alkyl, SO2—C1-C6-alkyl, C3-C7-cycloalkyl, Aryl, C1-C4-alkylene-aryl, CO—O—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-aryl, CO-aryl, SO2-aryl, hetaryl, CO-hetaryl or SO2—C1-C4-alkylene-aryl;
• Rz6, Rz7 independently of one another:
• hydrogen, OH, or
• each optionally substituted C1-C6-alkyl, C1-C4-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylene-C3-C7-cycloalkyl, C3-C7-cycloalkyl, aryl, C1-C4-alkylene-aryl, hetaryl or C1-C4-alkylene-hetaryl;
• R1, R2, R3 independently of one another:
• hydrogen, OH, CN, or
• each optionally substituted C1-C6-alkyl, O—C1-C6-alkyl, C1-C6-alkylene-OC1-C6-alkyl, C3-C7-cycloalkyl, O—C3-C7-cycloalkyl, aryl, hetaryl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, O-aryl, O—C1-C4-alkylene-aryl, O-hetaryl, O—C1-C4-alkylene-hetaryl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—CO—O-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-aryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-Aryl, OCO—C1-C6-alkyl, OCOaryl, OCO-hetaryl, OCO—C1-C4-alkylene-aryl, OCO—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl or SO2—C1-C4-alkylene-aryl, or
• each independently from the third moiety two moieties of R1, R2 or R3 together form a 5 to 7-membered, optionally substituted, saturated or unsaturated carbocycle or an optionally substituted, saturated or unsaturated, which can contain one, two or three further different or identical heteroatoms from the group O, N, S, wherein optionally two moieties substituted on this carbo- or heterocycle can together form an anellated, saturated, unsaturated, or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S and wherein the cycle formed can be optionally substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• Q:
• a doubly substituted 5-membered hetaryl moiety, chosen from Q1 to Q7
• E:
• O, N—RQ1 or S;
• RQ1:
• hydrogen, or
• each optionally substituted C1-C4-alkyl, CO—C1-C4-alkyl, SO2—C1-C4-alkyl, CO—O—C1-C4-alkyl, aryl, C1-C4-alkylene-aryl, CO-aryl, CO-hetaryl, SO2-aryl, SO2-hetaryl, CO—O-aryl, CO—C1-C4-alkylene-aryl, SO2—C1-C4-alkylene-aryl or CO—O—C1-C4-alkylene-aryl;
• R4, R5 each independently of one another, a moiety chosen from the groups 1.), 2.), 3.), 4.), 5.), 6.) or 7.):
• 1.) hydrogen, halogen, CN, CF3, CHF2, or
• each optionally substituted C1-C1O-alkyl, C2-C10-alkenyl, C2-C1Q-alkynyl, C3-C7-cycloalkyl, C1-C6-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, C1-C6-alkylene-O—C1-C6-alkyl, C1-C6-alkylene-O-aryl, COO—C1-C4-alkyl or C1-C4-alkylene-COO—C1-C4-alkyl;
• 3.) phenyl or naphthyl, which are substituted with RQ2, RQ3 and RQ4, wherein
• RQ2, RQ3 and RQ4 each independently of one another represent a substituent from the following group:
• hydrogen, NO2, NH2, OH, CN, CF3, CHF2, OCF3, OCHF2, COOH, O—CH2—COOH, SH, halogen, or
• each optionally substituted aryl, hetaryl, heterocycloalkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, C1-C4-alkylene-aryl or ClC4-alkylene-hetaryl, or
• O—R35, S—RQ5, NRQ7RQ8, CO—ORQ6, NRQB—OO—O—RQ6, O—CH2—COO—Re, NRQ8—CO—RQ6, SO2—RQ6, NRas—SO2—RQ6, SO2NH2, CO—NH2, SO2—NRQ7RQ8 or CO—NRQ7RQ8, or
• two of the moieties RQ2, RQ3 or RQ4 together form a 3 to 7-membered, optionally substituted, saturated, unsaturated carbocycle or an optionally substituted, saturated, unsaturated aromatic heterocycle which can contain up to three further different or identical heteroatoms O, N, S, and optionally two moieties substituted on this heterocycle can form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S, and the cycle formed may optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• RQ5 each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkyleneheterocycloalkyl, heterocycloalkyl, aryl or hetaryl;
• RQ6 each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl or C1-C6-alkylene-O—C1-C6-alkyl;
• RQ7 hydrogen, OH, CN, or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C6-alkylene-O—C1-C6-alkyl, CO—C1-C6-alkyl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—C1-C4-alkylene-hetaryl;
• RQ8 hydrogen or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, COC1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—C1-C4-alkylene-hetaryl;
• or both moieties RQ7 and RQ8 form, together with the nitrogen, a 3 to 7-membered, optionally substituted, saturated or aromatic heterocycle, which can contain one, two or three different or identical heteroatoms O, N, S;
• and optionally two moieties substituted on this heterocycle can together form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S, and the cycle formed can be optionally substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• 3.) a 5- or 6-membered, hetaryl moiety, optionally substituted with 1 or 2 substituents from the group consisting of:
• 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-pyridazinyl, 4-pyridazinyl, 5-pyridazinyl, 6-pyridazinyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, thiadiazolyl, oxadiazolyl or triazinyl or their anellated derivatives indazolyl, indolyl, benzothiophenyl, benzofuranyl, indolinyl, benzimidazolyl, benzthiazolyl, benzoxazolyl, chinolinyl and isochinolinyl;
• 4.) both moieties R4 and R5 together form a 4 to 7-membered, optionally substituted, saturated or unsaturated or aromatic carbocycle or a 5- or 6-membered optionally substituted, saturated or unsaturated or aromatic heterocycle, which can contain up to three further different or identical heteroatoms O, N, S, and which can be subtituted with up to two further moieties, wherein optionally two moieties substituted on this carbo- or heterocycle together form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S and wherein the cycle formed can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• 5.) a C6-C1O— bi- or tricyclyc, saturated hydrocarbon moiety;
• 6.) each optionally substituted C1-C8-alkyl-NH2, C1-C8-alkyl-NRQ7RQ8, C1-C8-alkyl-CO—NRQ7RQ8, C1-C8-alkyl-SO2NRa7Ros, C1-C8-alkyl-CO—NF12, C1-C8-alkyl-SO2NH2, CO—NH2, CO—NRQ7RQ8, SO2NH2, SO2NRQ7RQ8, NRQ7RQ8;
• 7.) a 4-7-membered mono- or bicyclic saturated or unsaturated heterocycle, which can contain up to two different or identical heteroatoms from the group 0, N or S, wherein this cycle can also be multiply substituted. For the case that the heterocycle contains an N— atom, this can be substituted with an RQ7 moiety.
• for the preparation of a medicament for the treatment of diseases modulated by a 5-HT5 receptor activity.

The method of a guanidine compound of the general formula 1A

• of the corresponding enantiomeric, diastereomeric and/or tautomeric forms thereof as well as pharmaceutically acceptable salts thereof,
• wherein the given moieties have the following definitions:
• W:
• a moiety of the general formula W1 or W2
• A:
• NO2, NH2, OH, CN, CF3, OCF3, CHF2, OCHF2, COOH, O—CH2—COOH, halogen, SH, or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl or C1-C4-alkyleneheterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-hetaryl or C1-C4-alkylene-aryl, or
• O—RA1, CO—RA1, S—RA1, SO—RA1, CO—O—RA1, NRA4—CO—O—RA1, O—CH2—COO—RA1, NRA2RA3, CO—NH2, SO2NH2, NRA4—CaRA1, SO2—RA1, NRA4—SO2—RA1, SO2NRA2RA3 or CO—NRA2RA3;
• RA1:
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkyleneheterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-aryl, C2-C6-alkenylene-aryl or C1-C6-alkylene-hetaryl;
• RA2:
• hydrogen, OH, CN, or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—C1-C4-alkylene-hetaryl;
• RA3:
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, ClC4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, C1-C6-alkylene-O—C1-C6-alkyl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—C1-C4-alkylene-hetaryl;
• or the moieties RA2 and RA3 form, together with the nitrogen, a 3 to 7-membered, optionally substituted, saturated or aromaticbeterocycle, which can contain one, two or three further different or identical heteroatoms from the group O, N, S;
• wherein
• optionally two moieties substituted on this heterocycle together can form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S, and wherein the so-formed cycle can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• RA:
• hydrogen, or
• each optionally substituted C1-C6-alkyl, C1-C6-alkylene-O—C1-C6-alkyl, C2-C6-alkenyl, C3-C12-alkynyl, CO—C1-C6-alkyl, CO—O—C1-C6-alkyl, SO2—C1-C6-alkyl, C3-C7-cycloalkyl, aryl, C1-C4-alkylene-aryl, CO—O-arylalkyl, CO—C1-C4-alkylene-aryl, CO-aryl, SO2-aryl, hetaryl, CO-hetaryl or SO2—C1-C4-alkylene-aryl;
• B:
• hydrogen or as moiety A is defined,
• or each independently from another, two of the moieties A, B or Rw1 together form a 3 to 7-membered, optionally substituted, saturated or unsaturated carbocycle or an optionally substituted, saturated or unsaturated or aromatic heterocycle, which can contain one, two or three further different or identical heteroatoms from the group O, N, S;
• wherein optionally two moieties substituted on this carbo- or heterocycle can togehter form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S and wherein the heterocycle formed can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• Rw1:
• hydrogen, OH, halogen, NO2, NH2, CN, CF3, CHF2, O—CF3, O—CHF2, or each optionally substituted C1-C6-alkyl, C3-C7-cycloalkyl, C1-C6-alkylene-OC1-C6-alkyl, C1-C6alkylene-S—C1-C6-alkyl, aryl, hetaryl, O—C1-C6-alkyl, O— aryl, O-benzyl, C1-C6-alkylamino, C1-C6-dialkylamino, pyrrolidinyl, piperidinyl, morpholinyl, CO—C1-C6-alkyl, SO2—C1-C6-alkyl, CO-aryl, SO2aryl, CO—C1-C4-alkylene-aryl, SO2—C1-C4-alkylene-aryl, SO-aryl, CO—NH2, CO—NH—C1-C6-alkyl, SO2NH—C1-C6-alkyl, CON(C1-C6-alkyl)2, SO2N(C1-C6-alkyl)2, NH—SO2—C1-C6-alkyl or NH—CO—C1-C6-alkyl;
• D:
• as moiety A is defined;
• Z:
• a moiety of the general formula Z1
• with the indices
• a=0-4
• b=0, 1
• c=0-4
• wherein the sum of a, b and c is no more than 5;
• Rz1, Rz2, Rz3, Rz4 independently of one another:
• hydrogen, halogen, OH, or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylene-C3-C7-cycloalkyl, C3-C7-cycloalkyl, aryl, C1-C4-alkylene-aryl, hetaryl or C1-C4-alkylene-hetaryl, or
• each independently of one another, two moieties Rz1 and Rz2 or Rz3 and Rz4 together form a 3 to 7-membered, optionally substituted, saturated or unsaturated carbo- or heterocycle, which can contain up to three heteroatoms from the group 0, N or S;
• Vz:
• —CO—, —CO—NRz5—, —NRz5—OO—, —O—, —S—, —SO—, —SO2—, —SO2—NRz5—, —NRz5—SO2—, —CS—, —CS—NR,5—, —NRz5—CS—, —CS—O—, —O—CS—, —CO—O—, —O—CO—, —O—, ethynylene, —C(═CRz5Rz7)—, —CRz6═CRz7—, —NRz5—CO—NRz5—, —O—OO—NRz5—, —NRz5—;
• Rz5, Rz5* independently of one another:
• hydrogen, or
• each optionally substituted C1-C6-alkyl, C1-C6-alkylene-O—C1-C6-alkyl, C2-C6-alkenyl, C3-C12-alkynyl, CO—C1-C6-alkyl, CO—O—C1-C6-alkyl, SO2—C1-C6alkyl, C3-C7-cycloalkyl, aryl, C1-C4-alkylene-aryl, CO—O—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-aryl, CO-aryl, SO2-aryl, hetaryl, CO-hetaryl or SO2—C1-C4-alkylene-aryl;
• Rz6, Rz7 independently of one another:
• hydrogen, OH, or
• each optionally substituted C1-C6-alkyl, C1-C4-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylene-C3-C7-cycloalkyl, C3-C7-cycloalkyl, aryl, C1-C4-alkylene-aryl, hetaryl or C1-C4-alkylene-hetaryl;
• R1, R2, R3 independently of one another:
• hydrogen, OH, CN, or
• each optionally substituted C1-C6-alkyl, O—C1-C6-alkyl, C1-C6-alkylene-O—C1-C6-alkyl, C3-C7-cycloalkyl, O—C3-C7-cycloalkyl, aryl, hetaryl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, O-aryl, O—C1-C4-alkylene-aryl, O— hetaryl, O—C1-C4-alkylene-hetaryl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-aryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl, OCO—C1-C6-alkyl, OCO-aryl, OCO-hetaryl, OCO—C1-C4-alkylene-aryl, OCO—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl or SO2—C1-C4-alkylene-aryl, or
• each independently of the third moiety, two moieties of R1, R2 or R3 together form a 5 to 7-membered, optionally substituted, saturated or unsaturated carbocycle, or an optionally substituted, saturated or unsaturated, which can contain one, two or three different or identical heteroatoms from the group O, N, S, wherein optionally two moieties substituted on this carbo- or heterocycle can together form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle may contain up to three different or identical heteroatoms O, N, S and wherein the cycle formed can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• Q:
• a dobly substituted 5-membered hetaryl moiety, chosen from Q1 to Q6
• E:
• O, N—RQ1 or S;
• RQ1:
• hydrogen, or
• each optionally substituted C1-C4-alkyl, SO2—C1-C4-alkyl, CO—O—C1-C4-alkyl, aryl, C1aralkylene-aryl, CO-aryl, CO-hetaryl, SO2-aryl, SO2-hetaryl, CO—O-aryl, CO—C1-C4-alkylene-aryl, SO2—C1-C4-alkylene-aryl or CO—O—C1-C4-alkylene-aryl;
• R4, R5 each independently of one another a moiety chosen from the groups 1.), 2.), 3.), 4.) or 5.):
• 1.) hydrogen, halogen, CN, CF3, CHF2, or
• each optionally substituted C1-C1O-alkyl, C2-C1Q-alkenyl, C2-C1O-allynyl, C3-C7-cycloalkyl, C1-Ce-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, C1-C6-alkylene-O—C1-C6-alkyl, C1-C6-alkylene-O-aryl, COO—C1-C4-alkyl or C1-C4-alkylene-COO—C1-C4-alkyl;
• 4.) Phenyl or naphthyl, which are each substituted with RQ2, RQ3 and RQ4, wherein
• RQ2, RQ3 and RQ4 each independently from one another represent a substituent from the following group:
• hydrogen, NO2, NH2, OH, CN, CF3, CHF2, OCF3, OCHF2, COON, O—CH2—COOH, SH, halogen, or
• each optionally substituted aryl, hetaryl, heterocycloalkyl, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, C1-C4-alkylene-aryl or C1-C4-alkylene-hetaryl, or
• O—RQ5, S—RQ5, NRQ7RQ8, CO—ORQ6, NRQ8—OO—O—RQ6, O—CH2—COO—RQ6, NRQ8—CO—RQ6, SO2—RQ6, NRQ8—SO2—RQ6, SO2NH2, CO—NH2, SO2—NRQ7RQ8 or CO—NRQ7RQ8, or
• two of the moieties RQ2, RQ3 or RQ4 together form a 3 to 7-membered, optionally substituted, saturated, unsaturated carbocycle or an optionally substituted, saturated, unsaturated aromatic heterocycle, which can contain up to three further different or identical heteroatoms O, N, S, and optionally two moieties substituted on this heterocycle together can form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S, and the cycle formed can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• RQ5 each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, heterocycloalkyl, aryl or hetaryl;
• RQ6 each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl or C1-C6-alkylene-O—C1-C6-alkyl;
• RQ7 hydrogen, OH, CN, or
• each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-O5-alkylene-O—C1-C6-alkyl, CO—C1-C6-alkyl, C1-C4-alkylene-aryl, C1-C4-alkylene-hetaryl, CO-aryl, CO-hetaryl, CO—C1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—C1-C4-alkylene-hetaryl;
• RQ8 each optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl, C1-C4-alkylene-C3-C7-cycloalkyl, C1-C4-alkylene-heterocycloalkyl, aryl, hetaryl, heterocycloalkyl, C1-C6-alkylene-O—C1-C6-alkyl, CO—C1-C6-alkyl, CO-aryl, CO-hetaryl, COC1-C4-alkylene-aryl, CO—C1-C4-alkylene-hetaryl, CO—O—C1-C6-alkyl, CO—O-aryl, CO—O—C1-C4-alkylene-aryl, CO—O-hetaryl, CO—O—C1-C4-alkylene-hetaryl, SO2—C1-C6-alkyl, SO2-aryl, SO2-hetaryl, SO2—C1-C4-alkylene-aryl or SO2—C1-C4-alkylene-hetaryl;
• or both moieties RQ7 and RQ8 form, together with the nitrogen, a 3 to 7-membered, optionally substituted, saturated or aromatic heterocycle, which can contain one, two or three further different or identical heteroatoms O, N, S;
• and optionally two moieties substituted on this heterocycle can together form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or same heteroatoms O, N, S and the cycle formed can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• 3.) a 5- or 6-membered, hetaryl moiety, optionally substituted with one or two substituents from the group consisting of:
• 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-pyridazinyl, 4-pyridazinyl, 5-pyridazinyl, 6-pyridazinyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, thiadiazolyl, oxadiazolyl or triazinyl or their anellated derivatives indazolyl, indolyl, benzothiophenyl, benzofuranyl, indolinyl, benzimidazolyl, benzthiazolyl, benzoxazolyl, chinolinyl and isochinolinyl;
• 4.) both moieties R4 and R5 together form a 4 to 7-membered, optionally substituted, saturated or unsaturated or aromatic carbocycle or a 5- or 6-membered optionally substituted, saturated or unsaturated or aromatic heterocycle, which can contain up to three further different or identical heteroatoms O, N, S, and can be substituted with up to two further moieties, wherein optionally two moieties substituted on this carbo- or heterocycle can together form an anellated, saturated, unsaturated or aromatic carbocycle or heterocycle, wherein the heterocycle can contain up to three different or identical heteroatoms O, N, S and wherein the cycle formed can optionally be substituted or a further, optionally substituted cycle can be condensed onto this cycle;
• 5.) a C8-C10- bi- or tricyclyc, saturated hydrocarbon moiety;
• for the manufacture of a medicament for the treatment of diseases which are modulated by a 5-HT5 receptor activity.