Vanilloid receptor ligands and use thereof for the production of pharmaceutical preparations

A compound of formula A

• in which
• X denotes O;
• Y denotes a linear or branched, saturated or unsaturated aliphatic C1-10 residue;
• n denotes 1;
• R1 and R4, mutually independently, in each case denote H;
• R2 R3, mutually independently, in each case denote H;
• F;
• Cl;
• Br;
• I;
• or a linear or branched, saturated or unsaturated aliphatic C1-10 residue;
• R5 denotes H, or a linear or branched, unsaturated aliphatic C1-10 residue;
• T denotes C—R6 and U denotes C—R7 and V denotes N and W denotes C—R8
• R6 and R7, mutually independently denotes H;
• F;
• Cl;
• Br;
• I;
• a linear or branched, saturated or unsaturated aliphatic C1-10 residue;
• or a 6- or 10-membered aryl residue, which may be attached via a linear or branched C1-6 alkylene group;
• R8 denotes H;
• F;
• Cl;
• Br;
• I;
• a saturated or unsaturated chain comprising 1 to 7 carbon atoms as chain members;
• an unsaturated or saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered cycloaliphatic residue optionally comprising at least one heteroatom as a ring member, which residue is in each case attached to the parent structure via a carbon atom in the ring of the cycloaliphatic residue and may be attached via a linear or branched, unsubstituted or at least monosubstituted C1-6 alkylene group or C2-6 alkenylene group or C2-6 alkynylene group;
• and
• R25 and R26, mutually independently, in each case denote a hydrogen residue;
• or a linear or branched, saturated or unsaturated aliphatic C1-10 residue
• a steroisomer thereof, a diastereoisomer thereof, an enantiomer thereof, a racemate thereof or a salt thereof.

A compound of formula A,

• in which
• X denotes O;
• Y denotes a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted aliphatic C1-10 residue;
• n denotes 1;
• R1 and R4 are H;
• R2 and R3, mutually independently, in each case denote H;
• F;
• Cl;
• Br;
• I;
• or a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted aliphatic C1-10 residue;
• R5 is an unsubstituted, saturated, branched or unbranched aliphatic C1-10 residue;
• T denotes C—R6;
• U denotes C—R7;
• V denotes N;
• W denotes C—R8;
• R6 is H or an unsubstituted, saturated, branched or unbranched aliphatic C1-10 residue;
• R7 is H;
• R8 is selected from the group consisting of H, F, Cl, Br, I, an unsubstituted, saturated or unsaturated, branched or unbranched aliphatic C1-10 residue, OR15, SR15, wherein R15 is selected from the group consisting of H, a saturated or unsaturated, branched or unbranched aliphatic C1-10 residue which may be substituted with one or more of OH, O-phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzoyl, phenyl, pyridyl, NH2, piperidinyl, pyrrolidinyl, azepanyl, indolyl, thiophenyl, thiazolyl, imidazolyl, oxazolyl, pyrimidinyl, piperazinyl, morpholinyl and thiomorpholinyl;
• R15 denotes a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted aliphatic C1-10 residue;
• denote an unsaturated or saturated, unsubstituted or at least monosubstituted 3-, 4-, 5-, 6-, 7-, 8- or 9-membered cycloaliphatic residue optionally comprising at least one heteroatom as a ring member, which residue may be one or more of (i) fused with a saturated or unsaturated, unsubstituted or at least monosubstituted mono- or polycyclic ring system and (ii) attached via a linear or branched, unsubstituted or at least monosubstituted C1-6 alkylene group or 2- to 6-membered heteroalkylene group;
• or denote an unsubstituted or at least monosubstituted 5- to 14-membered aryl or heteroaryl residue, which may be one or more of (i) fused with a saturated or unsaturated, unsubstituted or at least monosubstituted mono- or polycyclic ring system and (ii) attached via a linear or branched, unsubstituted or at least monosubstituted C1-6 alkylene group or 2- to 6-membered heteroalkylene group;
• and R25 and R26, mutually independently, in each case denote a hydrogen residue;
• or denote a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted aliphatic C1-10 residue;
• providing that R25 and R26 do not in each case denote a hydrogen residue;
• wherein unless otherwise stated, the above-stated aliphatic C1-10 residues may optionally in each case be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —NO2, —OH, —NH2, —SH, —O(C1-5-alkyl), —S(C1-5-alkyl), —NH(C1-5-alkyl), —N(C1-5-alkyl)(C1-5-alkyl), —C(═O)—O—C1-5-alkyl, —O—C(═O)—C1-5-alkyl, —O-phenyl, phenyl, —OCF3 and —SCF3;
• the above-stated 2- to 6-membered heteroalkylene groups, C1-6-alkylene groups, C2-6-alkenylene groups and C2-6-alkynylene groups may optionally in each case be substituted with 1, 2, 3, 4, 5, 6, 7, 8 or 9 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —NO2, —OH, —NH2, —SH, —O(C1-5-alkyl), —S(C1-5-alkyl), —NH(C1-5-alkyl), —N(C1-5-alkyl)(C1-5-alkyl), —OCF3 and —SCF3;
• the above-stated (hetero)cycloaliphatic residues may optionally in each case be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of —C1-6-alkylene-OH, ═CH2, —O—C1-5-alkylene-oxetanyl, —C1-5-alkylene —O—C1-5-alkylene-oxetanyl, —CH2—NH—C1-5-alkyl, —CH2—N(C1-5-alkyl)2, —N[C(═O)—C1-5-alkyl]-phenyl, —CH2—O—C1-5-alkyl, oxo (═O), thioxo (═S), F, Cl, Br, I, —CN, —CF3, —SF5, —OH, —O—C(═O)—C1-5-alkyl, —NH2, —NO2, —O—CF3, —S—CF3, —SH, alkyl, —C1-5-alkyl, —C(═O)—C1-5-alkyl, —C(═O)—OH, —C(═O)—O—C1-5-alkyl, alkyl, —N(C1-5-alkyl)2, —NH-phenyl, —N(C1-5-alkyl)-phenyl, cyclohexyl, cyclopentyl, (4,5)-dihydroisoxazolyl, thiazolyl, (1,2,5)-thiadiazolyl, thiophenyl, phenethyl, piperidinyl, pyrrolidinyl, —(CH2)-pyridinyl, pyridinyl, —O-phenyl, —O-benzyl, phenyl and benzyl, wherein in each case the cyclic moiety of the residues oxetanyl, (4,5)-dihydroisoxazolyl, thiazolyl, (1,2,5)-thiadiazolyl, thiophenyl, phenethyl, —N[C(═O)—C1-5-alkyl]-phenyl, —NH-phenyl, —N(C1-5-alkyl)-phenyl, —(CH2)-pyridinyl, pyridinyl, —O-phenyl, —O-benzyl, phenyl and benzyl may optionally be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —OH, —CF3, —SF5, —CN, —NO2, —C1-5-alkyl, —O—C1-5-alkyl, —O—CF3, —S—CF3, phenyl and —O-benzyl;
• the rings of the above-stated mono- or polycyclic ring systems may optionally in each case be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of oxo (═O), thioxo (═S), F, Cl, Br, I, —CN, —CF3, —SF5, —OH, —O—C1-5-alkyl, —NH2, —NO2, —O—CF3, —S—CF3, —SH, —C1-5-alkyl, —C(═O)—C1-5-alkyl, —C(═O)—OH, —C(═O)—O—C1-5-alkyl, —N(C1-5-alkyl)2, —O-phenyl, —O-benzyl, phenyl and benzyl, wherein in each case the cyclic moiety of the residues —O-phenyl, —O-benzyl, phenyl and benzyl may optionally be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —OH, —CF3, —SF5, —CN, —NO2, —C1-5-alkyl, —O—C1-5-alkyl, —O—CF3, —S—CF3, phenyl and —O-benzyl,
• and the above-stated aryl or heteroaryl residues may optionally in each case be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, I, —CN, —CF3, —SF5, —OH, —O—C1-5-alkyl, —NH2, —NO2, —O—CF3, —S—CF3, —SH, —S—C1-5-alkyl, —C1-5-alkyl, —C(═O)—OH, —C(═O)—O—C1-5-alkyl, —NH—C1-5-alkyl, —N(C1-5-alkyl)2, —NH—S(═O)2—C1-5-alkyl, —NH—C(═O)—O—C1-5-alkyl, —C(═O)—H, —C(═O)—C1-5-alkyl, —C(═O)—NH2, —C(═O)—NH—C1-5-alkyl, —C(═O)—N—(C1-5-alkyl)2, —O-phenyl, —O-benzyl, phenyl and benzyl, wherein in each case the cyclic moiety of the residues —O-phenyl, —O-benzyl, phenyl and benzyl may optionally be substituted with 1, 2, 3, 4 or 5 substituents mutually independently selected from the group consisting of F, Cl, Br, —OH, —CF3, —SF5, —CN, —NO2, —C1-5-alkyl, —O—C1-5-alkyl, —O—CF3, —S—CF3, phenyl and —O-benzyl,
• and
• the above-stated heteroalkylene groups in each case comprise 1, 2 or 3 heteroatom(s) mutually independently selected from the group consisting of oxygen, nitrogen (NH) and sulfur,
• the above-stated (hetero)cycloaliphatic residues may in each case optionally comprise 1, 2 or 3 heteroatom(s) mutually independently selected from the group consisting of oxygen, nitrogen and sulfur,
• the rings of the above-stated mono- or polycyclic ring systems are in each case 5-, 6- or 7-membered and may in each case optionally comprise 1, 2, 3, 4 or 5 heteroatom(s) as ring member(s), which are mutually independently selected from the group consisting of oxygen, nitrogen and sulfur,
• the above-stated heteroaryl residues in each case optionally comprise 1, 2, 3, 4 or 5 heteroatom(s) mutually independently selected from the group consisting of oxygen, nitrogen and sulfur as ring member(s);
• a steroisomer thereof, a diastereoisomer thereof, an enantiomer thereof, a racemate thereof or a salt thereof.