Substituted phenylureas and phenylamides as vanilloid receptor ligands
The invention relates to substituted phenylureas and phenylamides, to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.
1. Substituted compounds of general formula (I)
wherein
X represents CR 3 or N,
wherein R 3 represents H; C 1-10 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted;
A represents N or CR 5b ,
n represents 1, 2, 3 or 4;
R 0 represents C 1-10 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; C 3-10 cycloalkyl or heterocyclyl, respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl or heteroaryl, respectively unsubstituted or mono- or polysubstituted; C 3-10 cycloalkyl or heterocyclyl bridged via C 1-8 alkyl, respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted, wherein the alkyl chain can be respectively branched or unbranched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; or aryl or heteroaryl bridged via C 1-8 alkyl, respectively unsubstituted or mono- or polysubstituted, wherein the alkyl chain can be respectively branched or unbranched, saturated or unsaturated, unsubstituted, mono- or polysubstituted;
R 1 represents C 1-10 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted; C 3-10 cycloalkyl 1 or heterocyclyl 1 , respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted; aryl or heteroaryl, respectively unsubstituted or mono- or polysubstituted; C 3-10 cycloalkyl 1 or heterocyclyl 1 bridged via C 1-8 alkyl, respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted, wherein the alkyl chain can be respectively branched or unbranched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; or aryl or heteroaryl bridged via C 1-8 alkyl, respectively unsubstituted or mono- or polysubstituted, wherein the alkyl chain can be respectively branched or unbranched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; C(═O)—R 0 ; C(═O)—OH; C(═O)—OR 0 ; C(═O)—NHR 0 ; C(═O)—N(R 0 ) 2 ; OH; O—R 0 ; SH; S—R 0 ; S(═O) 2 —R 0 ; S(═O) 2 —OR 0 ; S(═O) 2 —NHR 0 ; S(═O) 2 —N(R 0 ) 2 ; NH 2 ; NHR 0 ; N(R 0 ) 2 ; NH—S(═O) 2 —R 0 ; N(R 0 )(S(═O) 2 —R 0 ; or SCl 3 ;
R 2 represents H; R 0 ; F; I; CN; NO 2 ; OH; SH; CF 3 ; CF 2 H; CFH 2 ; CF 2 Cl; CFCl 2 ; CH 2 CF 3 ; OCF 3 ; OCF 2 H; OCFH 2 ; OCF 2 Cl; OCFCl 2 ; SCF 3 ; SCF 2 H; SCFH 2 ; SCF 2 Cl; SCFCl 2 ; S(═O) 2 —CF 3 ; S(═O) 2 —CF 2 H; S(═O) 2 —CFH 2 ; or SF 5 ;
R 4 represents H; F; Cl; Br; I; OH; C 1-10 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted;
R 5a represents H; OH; C 1-10 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted;
R 5b represents H or R 0 ;
or R 5a and R 5b form together with the carbon atom connecting them a C 3-10 cycloalkyl or a heterocyclyl, respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted;
R 6 , R 7 , R 9 and R 10 each independently of one another represent H; F; Cl; Br; I; NO 2 ; CN; CF 3 ; CF 2 H; CFH 2 ; CF 2 Cl; CFCl 2 ; R 0 ; C(═O)H; C(═O)R 0 ; CO 2 H; C(═O)OR 0 ; CONH 2 ; C(═O)NHR 0 ; C(═O)N(R 0 ) 2 ; OH; OCF 3 ; OCF 2 H; OCFH 2 ; OCF 2 Cl; OCFCl 2 ; OR 0 ; O—C(═O)—R 0 ; O—C(═O)—O—R 0 ; O—(C═O)—NH—R 0 ; O—C(═O)—N(R) 2 ; O—S(═O) 2 —R 0 ; O—S(═O) 2 OH; O—S(═O) 2 OR 0 ; O—S(═O) 2 NH 2 ; O—S(═O) 2 NHR 0 ; O—S(═O) 2 N(R 0 ) 2 ; NH 2 ; NH—R 0 ; N(R 0 ) 2 ; NH—C(═O)—R 0 ; NH—C(═O)—O—R 0 ; NH—C(═O)—NH 2 ; NH—C(═O)—NH—R 0 ; NH—C(═O)—N(R 0 ) 2 ; NR 0 —C(═O)—R 0 ; NR 0 —C(═O)—O—R 0 ; NR 0 —C(═O)—NH 2 ; NR 0 —C(═O)—NH—R 0 ; NR 0 —C(═O)—N(R 0 ) 2 ; NH—S(═O) 2 OH; NH—S(═O) 2 R 0 ; NH—S(═O) 2 OR 0 ; NH—S(═O) 2 NH 2 ; NH—S(═O) 2 NHR 0 ; NH—S(═O) 2 N(R 0 ) 2 ; NR 0 —S(═O) 2 OH; NR 0 —S(═O) 2 R 0 ; NR 0 —S(═O) 2 OR 0 ; NR 0 —S(═O) 2 NH 2 ; NR 0 —S(═O) 2 NHR 0 ; NR 0 —S(═O) 2 N(R 0 ) 2 ; SH; SCF 3 ; SCF 2 H; SCFH 2 ; SCF 2 Cl; SCFCl 2 ; SR 0 ; S(═O)R 0 ; S(═O) 2 R 0 ; S(═O) 2 OH; S(═O) 2 OR 0 ; S(═O) 2 NH 2 ; S(═O) 2 NHR 0 ; or S(═O) 2 N(R 0 ) 2 ;
R 8 represents H; F; Cl; Br; I; NO 2 ; CN; CF 3 ; CF 2 H; CFH 2 ; CF 2 Cl; CFCl 2 ; R 0 ; C(═O)H; C(═O)R 0 ; CO 2 H; C(═O)OR 0 ; CONH 2 ; C(═O)NHR 0 ; C(═O)N(R 0 ) 2 ; OH; OCF 3 ; OCF 2 H; OCFH 2 ; OCF 2 Cl; OCFCl 2 ; OR 0 ; O—C(═O)—R 0 ; O—C(═O)—O—R 0 ; O—(C═O)—NH—R 0 ; O—C(═O)—N(R 0 ) 2 ; O—S(═O) 2 —R 0 ; O—S(═O) 2 OH; O—S(═O) 2 OR 0 ; O—S(═O) 2 NH 2 ; O—S(═O) 2 NHR 0 ; O—S(═O) 2 N(R 0 ) 2 ; NH 2 ; NH—R 0 ; N(R 0 ) 2 ; NH—C(═O)—R 0 ; NH—C(═O)—O—R 0 ; NH—C(═O)—NH 2 ; NH—C(═O)—NH—R 0 ; NH—C(═O)—N(R 0 ) 2 ; NR 0 —C(═O)—R 0 ; NR 0 —C(═O)—O—R 0 ; NR 0 —C(═O)—NH 2 ; NR 0 —C(═O)—NH—R 0 ; NR 0 —C(═O)—N(R 0 ) 2 ; NH—S(═O) 2 OH; NH—S(═O) 2 R 0 ; NH—S(═O) 2 OR 0 ; NH—S(═O) 2 NH 2 ; NH—S(═O) 2 NHR 0 ; NH—S(═O) 2 N(R 0 ) 2 ; NR 0 —S(═O) 2 OH; NR 0 —S(═O) 2 R 0 ; NR 0 —S(═O) 2 OR 0 ; NR 0 —S(═O) 2 NH 2 ; NR 0 —S(═O) 2 NHR 0 ; NR 0 —S(═O) 2 N(R 0 ) 2 ; SH; SCF 3 ; SCF 2 H; SCFH 2 ; SCF 2 Cl; SCFCl 2 ; SR 0 ; S(═O)R 0 ; S(═O) 2 R 0 ; S(═O) 2 OH; S(═O) 2 OR 0 ; S(═O) 2 NH 2 ; S(═O) 2 NHR 0 ; or S(═O) 2 N(R 0 ) 2 ; wherein, if R 8 denotes R 0 and R 0 represents heteroaryl, said heteroaryl is selected from the group consisting of benzofuranyl, benzoimidazolyl, benzothienyl, benzothiadiazolyl, benzothiazolyl, benzotriazolyl, benzooxazolyl, benzooxadiazolyl, quinazolinyl, quinoxalinyl, carbazolyl, quinolinyl, dibenzofuranyl, dibenzothienyl, furyl (furanyl), imidazothiazolyl, indazolyl, indolizinyl, indolyl, isoquinolinyl, isoxazoyl, isothiazolyl, indolyl, naphthyridinyl, oxazolyl, oxadiazolyl, phenazinyl, phenothiazinyl, phthalazinyl, pyrazolyl, pyridyl (2-pyridyl, 3-pyridyl, 4-pyridyl), pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, purinyl, phenazinyl, thienyl (thiophenyl), triazolyl, tetrazolyl, thiazolyl, thiadiazolyl and triazinyl;
in which “substituted alkyl”, “substituted heterocyclyl” and “substituted cycloalkyl” relate, with respect to the corresponding residues, to the substitution of one or more hydrogen atoms each independently of one another by F; Cl; Br; I; NO 2 ; CN; ═O; ═NH; ═C(NH 2 ) 2 ; CF 3 ; CF 2 H; CFH 2 ; CF 2 Cl; CFCl 2 ; R 0 ; C(═O)H; C(═O)R 0 ; CO 2 H; C(═O)OR 0 ; CONH 2 ; C(═O)NHR 0 ; C(═O)N(R 0 ) 2 ; OH; OCF 3 ; OCF 2 H; OCFH 2 ; OCF 2 Cl; OCFCl 2 ; OR 0 ; O—C(═O)—R 0 ; O—C(═O)—O—R 0 ; O—(C═O)—NH—R 0 ; O—C(═O)—N(R 0 ) 2 ; O—S(═O) 2 —R 0 ; O—S(═O) 2 OH; O—S(═O) 2 OR 0 ; O—S(═O) 2 NH 2 ; O—S(═O) 2 NHR 0 ; O—S(═O) 2 N(R 0 ) 2 ; NH 2 ; NH—R 0 ; N(R 0 ) 2 ; NH—C(═O)—R 0 ; NH—C(═O)—O—R 0 ; NH—C(═O)—NH 2 ; NH—C(═O)—NH—R 0 ; NH—C(═O)—N(R 0 ) 2 ; NR 0 —C(═O)—R 0 ; NR 0 —C(═O)—O—R 0 ; NR 0 —C(═O)—NH 2 ; NR 0 —C(═O)—NH—R 0 ; NR 0 —C(═O)—N(R 0 ) 2 ; NH—S(═O) 2 OH; NH—S(═O) 2 R 0 ; NH—S(═O) 2 OR 0 ; NH—S(═O) 2 NH 2 ; NH—S(═O) 2 NHR 0 ; NH—S(═O) 2 N(R 0 ) 2 ; NR 0 —S(═O) 2 OH; NR 0 —S(═O) 2 R 0 ; NR 0 —S(═O) 2 OR 0 ; NR 0 —S(═O) 2 NH 2 ; NR 0 —S(═O) 2 NHR 0 ; NR 0 —S(═O) 2 N(R 0 ) 2 ; SH; SCF 3 ; SCF 2 H; SCFH 2 ; SCF 2 Cl; SCFCl 2 ; SR 0 ; S(═O)R 0 ; S(═O) 2 R 0 ; S(═O) 2 OH; S(═O) 2 OR 0 ; S(═O) 2 NH 2 ; S(═O) 2 NHR 0 ; or S(═O) 2 N(R 0 ) 2 ;
in which “substituted cycloalkyl 1 ” and “substituted heterocyclyl 1 ” relate, with respect to the corresponding residues, to the substitution of one or more hydrogen atoms each independently of one another by F; Cl; Br; I; NO 2 ; CN; ═O; ═C(NH 2 ) 2 ; CF 3 ; CF 2 H; CFH 2 ; CF 2 Cl; CFCl 2 ; R 0 ; C(═O)H; C(═O)R 0 ; CO 2 H; C(═O)OR 0 ; CONH 2 ; C(═O)NHR 0 ; C(═O)N(R 0 ) 2 ; OH; OCF 3 ; OCF 2 H; OCFH 2 ; OCF 2 Cl; OCFCl 2 ; OR 0 ; O—C(═O)—R 0 ; O—C(═O)—O—R 0 ; O—(C═O)—NH—R 0 ; O—C(═O)—N(R 0 ) 2 ; O—S(═O) 2 —R 0 ; O—S(═O) 2 OH; O—S(═O) 2 OR 0 ; O—S(═O) 2 NH 2 ; O—S(═O) 2 NHR 0 ; O—S(═O) 2 N(R 0 ) 2 ; SH; SCF 3 ; SCF 2 H; SCFH 2 ; SCF 2 Cl; SCFCl 2 ; SR 0 ; S(═O)R 0 ; S(═O) 2 R 0 ; S(═O) 2 OH; S(═O) 2 OR 0 ; S(═O) 2 NH 2 ; S(═O) 2 NHR 0 ; or S(═O) 2 N(R 0 ) 2 ;
in which “substituted aryl” relates, with respect to the corresponding residues, to the substitution of one or more hydrogen atoms each independently of one another by F; Cl; Br; I; NO 2 ; CF 3 ; CF 2 H; CFH 2 ; CF 2 Cl; CFCl 2 ; R 0 ; C(═O)H; C(═O)R 0 ; CO 2 H; C(═O)OR 0 ; CONH 2 ; C(═O)NHR 0 ; C(═O)N(R 0 ) 2 ; OH; OCF 3 ; OCF 2 H; OCFH 2 ; OCF 2 Cl; OCFCl 2 ; OR 0 ; O—C(═O)—R 0 ; O—C(═O)—O—R 0 ; O—(C═O)—NH—R 0 ; O—C(═O)—N(R 0 ) 2 ; O—S(═O) 2 —R 0 ; O—S(═O) 2 OH; O—S(═O) 2 OR 0 ; O—S(═O) 2 NH 2 ; O—S(═O) 2 NHR 0 ; O—S(═O) 2 N(R 0 ) 2 ; NH 2 ; NH—R 0 ; N(R 0 ) 2 ; NH—C(═O)—R 0 ; NH—C(═O)—O—R 0 ; NH—C(═O)—NH 2 ; NH—C(═O)—NH—R 0 ; NH—C(═O)—N(R 0 ) 2 ; NR 0 —C(═O)—R 0 ; NR 0 —C(═O)—O—R 0 ; NR 0 —C(═O)—NH 2 ; NR 0 —C(═O)—NH—R 0 ; NR 0 —C(═O)—N(R 0 ) 2 ; NH—S(═O) 2 OH; NH—S(═O) 2 R 0 ; NH—S(═O) 2 OR 0 ; NH—S(═O) 2 NH 2 ; NH—S(═O) 2 NHR 0 ; NH—S(═O) 2 N(R 0 ) 2 ; NR 0 —S(═O) 2 OH; NR 0 —S(═O) 2 R 0 ; NR 0 —S(═O) 2 OR 0 ; NR 0 —S(═O) 2 NH 2 ; NR 0 —S(═O) 2 NHR 0 ; NR 0 —S(═O) 2 N(R 0 ) 2 ; SH; SCF 3 ; SCF 2 H; SCFH 2 ; SCF 2 Cl; SCFCl 2 ; SR 0 ; S(═O)R 0 ; S(═O) 2 R 0 ; S(═O) 2 OH; S(═O) 2 OR 0 ; S(═O) 2 NH 2 ; S(═O) 2 NHR 0 ; or S(═O) 2 N(R 0 ) 2 ;
in which “substituted heteroaryl” relates, with respect to the corresponding residues, to the substitution of one or more hydrogen atoms each independently of one another by F; Cl; Br; I; NO 2 ; CN; CF 3 ; CF 2 H; CFH 2 ; CF 2 Cl; CFCl 2 ; R 0 ; C(═O)H; C(═O)R 0 ; CO 2 H; C(═O)OR 0 ; CONH 2 ; C(═O)NHR 0 ; C(═O)N(R 0 ) 2 ; OH; OCF 3 ; OCF 2 H; OCFH 2 ; OCF 2 Cl; OCFCl 2 ; OR 0 ; O—C(═O)—R 0 ; O—C(═O)—O—R 0 ; O—(C═O)—NH—R 0 ; O—C(═O)—N(R 0 ) 2 ; O—S(═O) 2 —R 0 ; O—S(═O) 2 OH; O—S(═O) 2 OR 0 ; O—S(═O) 2 NH 2 ; O—S(═O) 2 NHR 0 ; O—S(═O) 2 N(R 0 ) 2 ; NH 2 ; NH—R 0 ; N(R 0 ) 2 ; NH—C(═O)—R 0 ; NH—C(═O)—O—R 0 ; NH—C(═O)—NH 2 ; NH—C(═O)—NH—R 0 ; NH—C(═O)—N(R 0 ) 2 ; NR 0 —C(═O)—R 0 ; NR 0 —C(═O)—O—R 0 ; NR 0 —C(═O)—NH 2 ; NR 0 —C(═O)—NH—R 0 ; NR 0 —C(═O)—N(R 0 ) 2 ; NH—S(═O) 2 OH; NH—S(═O) 2 R 0 ; NH—S(═O) 2 OR 0 ; NH—S(═O) 2 NH 2 ; NH—S(═O) 2 NHR 0 ; NH—S(═O) 2 N(R 0 ) 2 ; NR 0 —S(═O) 2 OH; NR 0 —S(═O) 2 R 0 ; NR 0 —S(═O) 2 OR 0 ; NR 0 —S(═O) 2 NH 2 ; NR 0 —S(═O) 2 NHR 0 ; NR 0 —S(═O) 2 N(R 0 ) 2 ; SH; SCF 3 ; SCF 2 H; SCFH 2 ; SCF 2 Cl; SCFCl 2 ; SR 0 ; S(═O)R 0 ; S(═O) 2 R 0 ; S(═O) 2 OH; S(═O) 2 OR 0 ; S(═O) 2 NH 2 ; S(═O) 2 NHR 0 ; or S(═O) 2 N(R 0 ) 2 ;
in the form of the free compounds; the tautomers; the N-oxides; the racemate; the enantiomers, diastereomers, mixtures of the enantiomers or diastereomers or of an individual enantiomer or diastereomer; or in the form of the salts of physiologically compatible acids or bases.
2. Substituted compounds according to claim 1 , wherein
R 4 represents H; C 1-10 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH and O—C 1-4 alkyl;
A represents N or CR 5b ;
R 5a represents H; OH; C 1-10 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH and O—C 1-4 alkyl;
R 5b represents H; C 1-10 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH and O—C 1-4 alkyl; C 3-10 cycloalkyl or heterocyclyl, respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, ═O and O—C 1-4 alkyl; or C 3-10 cycloalkyl or heterocyclyl bridged via C 1-8 alkyl, respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br; I, OH, ═O and O—C 1-4 alkyl, wherein the alkyl chain can be respectively branched or unbranched, saturated or unsaturated, unsubstituted, mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, ═O and O—C 1-4 alkyl; or aryl, heteroaryl, respectively unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl, SCF 3 , S(═O) 2 OH and NH—S(═O) 2 —C 1-4 alkyl; or aryl or heteroaryl bridged via C 1-8 alkyl, respectively unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl, SCF 3 , S(═O) 2 OH and NH—S(═O) 2 —C 1-4 alkyl, wherein the alkyl chain can be respectively branched or unbranched, saturated or unsaturated, unsubstituted, mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, ═O and O—C 1-4 alkyl;
or R 5a and R 5b form together with the carbon atom connecting them a C 3-10 cycloalkyl or a heterocyclyl, respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, ═O and O—C 1-4 alkyl.
3. Substituted compounds according to claim 1 , wherein
R 4 represents H; methyl; ethyl; n-propyl; or isopropyl;
A represents N or CR 5b ;
R 5a represents H or CH 3 , preferably H, if A represents N;
or R 5a represents H or CH 3 , preferably H, if A represents CR 5b ,
wherein R 5b represents H; or C 1-4 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted; C 3-10 cycloalkyl, saturated or unsaturated, unsubstituted; or phenyl or benzyl, in each case unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, CF 3 , O—C 1-4 alkyl, OCF 3 and C 1-4 alkyl,
or R 5a and R 5b form together with the carbon atom connecting them a C 3-10 cycloalkyl, saturated or unsaturated, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, ═O and O—C 1-4 alkyl.
4. Substituted compounds according to claim 1 , wherein
R 1 represents substructure (T1)
in which
Y represents C(═O), O, S, S(═O) 2 , NH—C(═O) or NR 12 ,
wherein R 12 represents H; C 1-8 alkyl or S(═O) 2 —C 1-8 alkyl, in which C 1-8 alkyl can be respectively saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, O—C 1-4 alkyl, OCF 3 , NH 2 , NH—C 1-4 alkyl and N(C 1-4 alkyl) 2 ;
o represents 0 or 1,
R 11a and R 11b each independently of one another represent H; F; Cl; Br; I; NO 2 ; CF 3 ; CN; OH; OCF 3 ; NH 2 ; C 1-4 alkyl, O—C 1-4 alkyl, NH—C 1-4 alkyl, N(C 1-4 alkyl) 2 , in which C 1-4 alkyl can be respectively saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, O—C 1-4 alkyl, OH and OCF 3 ;
on the condition that if R 11a and R 11b are bound to the same carbon atom, only one of the substituents R 11a and R 11b can represent OH; OCF 3 ; NH 2 ; O—C 1-4 alkyl, NH—C 1-4 alkyl or N(C 1-4 alkyl) 2 ;
m represents 0, 1, 2, 3 or 4;
Z represents C 1-4 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, ═O, O—C 1-4 alkyl, OCF 3 , C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl, SCF 3 and S(═O) 2 OH; C 3-10 cycloalkyl 1 or heterocyclyl 1 , respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, C(═O)—OH, CF 3 , SH, S—C 1-4 alkyl, SCF 3 , S(═O) 2 OH, benzyl, phenyl, pyridyl and thienyl, wherein benzyl, phenyl, pyridyl, thienyl can be respectively unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl, SCF 3 and S(═O) 2 OH; aryl or heteroaryl, respectively unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl, SCF 3 , S(═O) 2 OH, benzyl, phenyl, pyridyl and thienyl, wherein benzyl, phenyl, pyridyl, thienyl can be respectively unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-8 alkyl, OCF 3 , C 1-4 alkyl, C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl, SCF 3 and S(═O) 2 OH.
5. Substituted compounds according to claim 4 , wherein
Y represents C(═O), O, S, S(═O) 2 , NH—C(═O) or NR 12 ,
wherein R 12 represents H; methyl; ethyl; n-propyl; isopropyl; n-butyl; sec.-butyl; tert.-butyl; S(═O) 2 -methyl; S(═O) 2 -ethyl;
o represents 0 or 1;
R 11a and R 11b each independently of one another represent H; F; Cl; Br; I; NO 2 ; CF 3 ; CN; methyl; ethyl; n-propyl; isopropyl; n-butyl; sec.-butyl; tert.-butyl; CH 2 CF 3 ; OH; O-methyl; O-ethyl; O—(CH 2 ) 2 —O—CH 3 ; O—(CH 2 ) 2 —OH; OCF 3 ; NH 2 ; NH-methyl; N(methyl) 2 ; NH-ethyl; N(ethyl) 2 ; or N(methyl)(ethyl);
on the condition that if R 11a and R 11b are bound to the same carbon atom, only one of the substituents R 11a and R 11b can represent OH; OCF 3 ; O-methyl; O-ethyl; O—(CH 2 ) 2 —O—CH 3 ; O—(CH 2 ) 2 —OH; NH 2 ; NH-methyl; N(methyl) 2 ; NH-ethyl; N(ethyl) 2 ; or N(methyl)(ethyl);
m represents 0, 1 or 2;
Z represents C 1-4 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, ═O, O—C 1-4 alkyl, OCF 3 , C(═O)—OH and CF 3 ; phenyl, naphthyl, furyl, pyridyl or thienyl, respectively unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-8 alkyl, SCF 3 , benzyl and phenyl, wherein benzyl and phenyl can be respectively unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl and SCF 3 ; C 3-10 cycloalkyl 1 or heterocyclyl 1 , respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, CF 3 , benzyl, phenyl and pyridyl, wherein benzyl, phenyl and pyridyl can be respectively unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl and SCF 3 .
6. Substituted compounds according to claim 1 , wherein
R 2 represents H; F; I; CN; NO 2 ; CF 3 ; CF 2 H; CFH 2 ; CF 2 Cl; CFCl 2 ; OH; OCF 3 ; OCF 2 H; OCFH 2 ; OCF 2 Cl; OCFCl 2 ; SH; SCF 3 ; SCF 2 H; SCFH 2 ; SCF 2 Cl; SCFCl 2 ; C 1-10 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, ═O, O—C 1-4 alkyl, OCF 3 , C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl, SCF 3 S(═O) 2 OH, benzyl, phenyl, pyridyl and thienyl, wherein benzyl, phenyl, pyridyl, thienyl can be respectively unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl, SCF 3 and S(═O) 2 OH; C 3-10 cycloalkyl or heterocyclyl, respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, OH, ═O, C 1-4 alkyl, O—C 1-4 alkyl, OCF 3 , C(═O)—OH and CF 3 ; or C 3-10 cycloalkyl or heterocyclyl bridged via C 1-8 alkyl, respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, ═O, C 1-4 alkyl, O—C 1-4 alkyl, OCF 3 , C(═O)—OH and CF 3 , wherein the alkyl chain can be respectively branched or unbranched, saturated or unsaturated, unsubstituted, mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, ═O and O—C 1-4 alkyl; aryl or heteroaryl, respectively unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-8 alkyl, SCF 3 , S(═O) 2 OH, benzyl, phenyl, pyridyl and thienyl, wherein benzyl, phenyl, pyridyl, thienyl can be respectively unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-8 alkyl, OCF 3 , C 1-4 alkyl, C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl, SCF 3 and S(═O) 2 OH; or aryl or heteroaryl bridged via C 1-8 alkyl, respectively unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-8 alkyl, SCF 3 , S(═O) 2 OH, benzyl, phenyl, pyridyl and thienyl, wherein benzyl, phenyl, pyridyl, thienyl can be respectively unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-8 alkyl, OCF 3 , C 1-4 alkyl, C(═O)—OH, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , SH, S—C 1-4 alkyl, SCF 3 and S(═O) 2 OH, wherein the alkyl chain can be respectively branched or unbranched, saturated or unsaturated, unsubstituted, mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, ═O and O—C 1-4 alkyl.
7. Substituted compounds according to claim 1 , wherein
R 6 and R 10 are each selected independently of one another from the group consisting of H; F; Cl; Br; I; CN; CF 3 ; OH; OCF 3 ; SH; SCF 3 ; C 1-4 alkyl, O—C 1-4 alkyl and NH—S(═O) 2 —C 1-4 alkyl, in which C 1-4 alkyl can be respectively saturated or unsaturated, branched or unbranched, unsubstituted;
R 7 , R 8 and R 9 are each selected independently of one another from the group consisting of H; F; Cl; Br; I; CN; NO 2 ; CF 3 ; OH; OCF 3 ; SH; SCF 3 ; NH 2 ; C(═O)—NH 2 ; C 1-4 alkyl, C 1-4 alkyl-O—C 1-4 alkyl, C(═O)—NH—C 1-4 alkyl, O—C 1-4 alkyl, NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , NH—C(═O)—C 1-4 alkyl, NH—S(═O) 2 —C 1-4 alkyl, S—C 1-4 alkyl, SO 2 —C 1-4 alkyl, SO 2 —NH(C 1-4 alkyl), SO 2 —N(C 1-4 alkyl) 2 , in which C 1-4 alkyl can be respectively saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, OH, O—C 1-4 alkyl, OCF 3 , CF 3 , NH—S(═O) 2 —C 1-4 alkyl, SH, S—C 1-4 alkyl, S(═O) 2 —C 1-4 alkyl and SCF 3 ; C 3-10 cycloalkyl, heterocyclyl or C 3-10 cycloalkyl or heterocyclyl bridged via C 1-8 alkyl, respectively saturated or unsaturated, unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, NO 2 , CN, OH, O—C 1-4 alkyl, OCF 3 , O 1-4 alkyl, CF 3 , NH 2 , NH(C 1-4 alkyl), N(C 1-4 alkyl) 2 , NH—S(═O) 2 —C 1-4 alkyl, N(C 1-4 alkyl)-S(═O) 2 —C 1-4 alkyl, SH, S—C 1-4 alkyl, S(═O) 2 —C 1-4 alkyl and SCF 3 , and wherein if appropriate the alkyl chain can be respectively branched or unbranched, saturated or unsaturated, unsubstituted, mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br; I, OH and O—C 1-4 alkyl; phenyl, pyridyl, furyl, thienyl, C(═O)—NH-phenyl, NH—C(═O)-phenyl, NH(phenyl), C(═O)—NH-pyridyl, NH—C(═O)-pyridyl, NH(pyridyl) or phenyl or pyridyl bridged via C 1-8 alkyl, wherein phenyl, pyridyl, furyl or thienyl are respectively unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, CF 3 , SH, S—C 1-4 alkyl and SCF 3 , and wherein if appropriate the alkyl chain can be respectively branched or unbranched, saturated or unsaturated, unsubstituted, mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br; I, OH and O—C 1-4 alkyl.
8. Substituted compounds according to claim 7 , wherein
R 6 and R 10 represent H.
9. Substituted compounds according to claim 1 , having general formula (If),
wherein
X represents CR 3 or N,
wherein R 3 represents H; methyl; ethyl; n-propyl; isopropyl; n-butyl; sec.-butyl; tert.-butyl; or CF 3 ;
A represents N or CR 5b ;
R 1 represents substructure (T1)
in which
Y represents C(═O), O, S, S(═O) 2 , NH—C(═O) or NR 12 ,
wherein R 12 represents H; methyl; ethyl; n-propyl; isopropyl; n-butyl; sec.-butyl; tert.-butyl; S(═O) 2 -methyl;
o represents 0 or 1;
R 11a and R 11b each independently of one another represent H; methyl; ethyl; n-propyl; isopropyl; n-butyl; sec.-butyl; tert.-butyl;
m represents 0, 1 or 2;
Z represents C 1-4 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, O—C 1-4 alkyl; C 3-10 cycloalkyl 1 , saturated or unsaturated, morpholinyl, tetrahydropyranyl, piperidinyl, 4-methylpiperazinyl, piperazinyl, respectively unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, OH, O—C 1-4 alkyl and C 1-4 alkyl; phenyl or pyridyl, respectively unsubstituted or mono- or polysubstituted with one or more substituents each selected independently of one another from the group consisting of F, Cl, Br, I, CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, CF 3 , SH, S—C 1-4 alkyl, SCF 3 ;
R 2 represents H; F; I; CF 3 ; CN; methyl; ethyl; n-propyl; isopropyl; n-butyl; sec.-butyl; tert.-butyl; cyclopropyl; cyclobutyl; phenyl, unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of C 1-4 alkyl, O—C 1-4 alkyl, F, Cl, Br, I, CF 3 and OCF 3 ;
R 4 represents H; methyl; ethyl; n-propyl; or isopropyl;
R 5a represents H or CH 3 if A represents N; or
represents H; methyl; ethyl; n-propyl; isopropyl if A represents CR 5b ;
R 5b represents H; methyl; ethyl; n-propyl; isopropyl; cyclopentyl; cylohexyl; or phenyl or benzyl, in each case unsubstituted or mono-, di- or trisubstituted with one, two or three substituents each selected independently of one another from the group consisting of C 1-4 alkyl, O—C 1-4 alkyl, F, Cl, Br, I, CF 3 and OCF 3 ;
or R 5a and R 5b form together with the carbon atom connecting them a C 3-10 cycloalkyl, saturated or unsaturated, unsubstituted,
R 7 and R 9 each independently of one another represent H; F; Cl; Br; I; C 1-4 alkyl, O—C 1-4 alkyl; F; Cl; Br; I;
R 8 represents H; F; Cl; Br; I; CN; NO 2 ; CF 3 ; OH; OCF 3 ; SH; SCF 3 ; NH 2 ; C(═O)—NH 2 ; C(═O)—NH(methyl); C(═O)—NH(ethyl); C(═O)—N (methyl) 2 ; C(═O)—N(ethyl) 2 ; C 1-4 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted or mono- or disubstituted with OH; NH—C(═O)-methyl; NH—C(═O)-ethyl; CH 2 —NH—S(═O) 2 -methyl; CH 2 —NH—S(═O) 2 -ethyl; NH—S(═O) 2 -methyl; NH—S(═O) 2 -ethyl; S-methyl; S-ethyl; S(═O) 2 -methyl; S(═O) 2 -ethyl; S(═O) 2 —NH-methyl; S(═O) 2 —NH-ethyl; S(═O) 2 —N(methyl) 2 ; S(═O) 2 —N(ethyl) 2 ; CH 2 —S(═O) 2 -methyl; CH 2 —S(═O) 2 -ethyl; OC 1-4 alkyl, saturated or unsaturated, branched or unbranched, unsubstituted; C 1-4 alkyl-O—C 1-4 alkyl-O—C 1-4 alkyl, C 3-10 cycloalkyl, or C 3-10 cycloalkyl bridged via C 1-8 alkyl, respectively saturated or unsaturated, unsubstituted, and wherein if appropriate the alkyl chain can be respectively branched or unbranched, saturated or unsaturated, unsubstituted; piperidinyl; piperazinyl; 4-methylpiperazinyl; morpholinyl; dioxidoisothiazolidinyl; phenyl, pyridyl, furyl, thienyl, C(═O)—NH-phenyl, NH—C(═O)-phenyl, NH(phenyl), C(═O)—NH-pyridyl, NH—C(═O)-pyridyl, NH(pyridyl), wherein phenyl, pyridyl, thienyl or furyl are respectively unsubstituted or mono- or polysubstituted with one or more substituents selected independently of one another from the group consisting of F, Cl, Br, I, CN, OH, O—C 1-4 alkyl, OCF 3 , C 1-4 alkyl, CF 3 , SH, S—C 1-4 alkyl and SCF 3 .
10. Substituted compounds according to claim 1 , selected from the group consisting of
3 N-((3-tert-butyl-1-methyl-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
4 (S)—N-((3-tert-butyl-1-methyl-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
5 N-((3-tert-butyl-1-hexyl-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
6 (S)—N-((3-tert-butyl-1-hexyl-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
7 N-((3-tert-butyl-1-cyclohexyl-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
8 (S)—N-((3-tert-butyl-1-cyclohexenyl-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
9 2-(3-fluoro-4-(methylsulphonamido)phenyl)-N-((3-methyl-1-phenyl-1H-pyrazol-5-yl)methyl)propanamide;
11 2-(3-fluoro-4-(methylsulphonamido)phenyl)-N-((3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-5-yl)methyl)propanamide;
12 N-((3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
13 N-((3-tert-butyl-1-(4-tert-butylphenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
14 N-((3-tert-butyl-1-(4-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
15 (S)—N-((3-tert-butyl-1-(4-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
16 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
17 (S)—N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
18 N-((3-tert-butyl-1-(3-chloro-4-fluorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
19 (E)-N-((3-tert-butyl-1-(4-methylstyryl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
20 N-((3-tert-butyl-1-(4-methoxyphenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
21 N-((1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
22 (R)—N-((1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
23 (S)—N-((1-(4-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
24 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
25 (R)—N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
26 (S)—N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)propanamide;
27 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-methoxy-4-(methylsulphonamido)phenyl)propanamide;
28 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-methoxy-4-(methylsulphonamido)phenyl)propanamide;
29 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3,5-difluoro-4-(methylsulphonamido)phenyl)propanamide;
30 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3,5-difluorophenyl)propanamide;
31 2-(4-bromo-3-fluorophenyl)-N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)propanamide;
32 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(4-isobutylphenyl)propanamide;
33 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamidomethyl)phenyl)propanamide;
34 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(furan-3-yl)phenyl)propanamide;
35 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(2-fluorobiphenyl-4-yl)propanamide;
36 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(4-(1,2-dihydroxyethyl)-3-fluorophenyl)propanamide;
37 4-(1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-2-fluorobenzamide;
38 4-(1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-N-ethylbenzamide;
39 4-(1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-2-fluoro-N-phenylbenzamide;
40 4-(1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-N-(4-fluorophenyl)benzamide;
41 4-(1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-N-(4-(trifluoromethyl)phenyl)benzamide;
42 4-(1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-N-(pyridin-4-yl)benzamide;
43 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(4-(trifluormethoxy)phenyl)propanamide;
44 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3,5-dibromo-4-hydroxyphenyl)acetamide;
45 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3,5-dibromo-4-hydroxyphenyl)propanamide;
46 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3,5-difluoro-4-hydroxyphenyl)propanamide;
47 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3,5-difluoro-4-methoxyphenyl)propanamide;
48 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(4-methoxy-3,5-dimethylphenyl)acetamide;
49 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(4-(N,N-dimethylsulphamoyl)-3-fluorophenyl)propanamide;
50 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(4-(4-chlorophenylamino)phenyl)propanamide;
51 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(4-(4-methoxyphenylamino)phenyl)propanamide;
52 2-(4-amino-3,5-difluorophenyl)-N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)propanamide;
53 2-(4-acetamido-3-fluorophenyl)-N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)propanamide;
54 N-(4-(1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-2-fluorophenyl)benzamide;
55 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-[4-(1,1-dioxidoisothiazolidin-2-yl)-3-fluorophenyl]propanamide;
56 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(4-(N,N-dimethylsulphamoyl)-3-fluorophenyl)propanamide;
57 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3,5-difluorophenyl)urea;
58 1-(4-bromo-3-fluorophenyl)-3-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)urea;
59 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-(trifluoromethyl)phenyl)urea;
60 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-(difluormethoxy)phenyl)urea;
61 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3,5-difluoro-4-methoxyphenyl)urea;
62 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-methoxy-3,5-dimethylphenyl)urea;
63 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(methylsulphonyl)phenyl)urea;
64 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(4-(phenylamino)phenyl)urea;
65 4-(3-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)ureido)-N-(4-fluorophenyl)benzamide;
66 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)-2-(3-fluorophenyl)acetamide;
67 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-cyclohexyl-2-(3-fluoro-4-(methylsulphonamido)phenyl)acetamide;
68 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonamido)phenyl)-2-p-tolylacetamide;
69 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-chloro-4-(methylthio)phenyl)propanamide;
70 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-chloro-4-(methylsulphonyl)phenyl)propanamide;
71 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylthio)phenyl)propanamide;
72 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulphonyl)phenyl)propanamide;
73 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluorophenyl)acetamide;
74 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluorophenyl)acetamide;
75 N-[[5-tert-butyl-2-(3-chlorophenyl)-2H-[1,2,4]triazol-3-yl]-methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
76 N-[[2-(3-chlorophenyl)-5-(trifluoromethyl)-2H-[1,2,4]triazol-3-yl]methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
77 N-[(5-tert-butyl-2-cyclohexyl-2H-[1,2,4]thiazol-3-yl)-methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
78 N-[[2-cyclohexyl-5-(trifluoromethyl)-2H-[1,2,4]triazol-3-yl]methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
79 N-[(5-tert-butyl-2-pyridin-3-yl-2H-[1,2,4]triazol-3-yl)-methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
80 2-[3-fluoro-4-(methanesulphonamido)phenyl]-N-[[2-pyridin-3-yl-5-(trifluoromethyl)-2H-[1,2,4]triazol-3-yl]methyl]propionamide;
81 N-[[5-tert-butyl-2-(6-chloropyridin-2-yl)-2H-pyrazol-3-yl]-methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
82 N-[[5-tert-butyl-2-(3,3-difluorocyclobutanecarbonyl)-2H-pyrazol-3-yl]-methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
83 N-[[2-(3-chlorophenyl)-4-methyl-5-(trifluoromethyl)-2H-pyrazol-3-yl]methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
84 N-[[2-(dipropylamino)-5-(trifluoromethyl)-2H-pyrazol-3-yl]methyl]-2-[4-(methanesulphonamido)-3-methoxyphenyl]propionamide;
85 N-[[2-(dipropylamino)-5-(trifluoromethyl)-2H-pyrazol-3-yl]methyl]-2-[3-fluoro-4-(hydroxymethyl)phenyl]propionamide;
86 N-[[2-(dipropylamino)-5-(trifluoromethyl)-2H-pyrazol-3-yl]methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
87 N-[[2-(dipropylamino)-5-(trifluoromethyl)-2H-pyrazol-3-yl]methyl]-2-(3-fluorophenyl)acetamide;
88 4-[1-[[2-(dipropylamino)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methylcarbamoyl]ethyl]-2-fluorobenzamide;
89 4-[1-[[2-(dipropylamino)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methylcarbamoyl]ethyl]-N-pyridin-2-yl-benzamide;
90 2-[3-fluoro-4-(hydroxymethyl)phenyl]-N-[[2-piperidin-1-yl-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]propionamide;
91 2-[3-fluoro-4-(2-hydroxyethyl)phenyl]-N-[[2-piperidin-1-yl-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]propionamide;
92 2-[3-fluoro-4-(methanesulphonamido)phenyl]-N-[[2-piperidin-1-yl-5-(trifluoromethyl)-2H-pyrazol-3-yl]methyl]propionamide;
93 2-[4-(methanesulphonamido)-3-methoxyphenyl]-N-[[2-piperidin-1-yl-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]propionamide;
94 2-[4-(1,2-dihydroxyethyl)-3-fluorophenyl]-N-[[2-piperidin-1-yl-5-(trifluoromethyl)-2H-pyrazol-3-yl]methyl]propionamide;
95 2-(3-fluorophenyl)-N-[[2-piperidin-1-yl-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]acetamide;
96 2-fluoro-4-[1-[[2-piperidin-1-yl-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methylcarbamoyl]ethyl]benzamide;
97 2-[3-fluoro-4-(methanesulphonamido)phenyl]-N-[[2-[(4-fluorophenyl)methylmethylamino]-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]propionamide;
98 N-[[5-tert-butyl-2-(2,2,2-trifluoroethylamino)-2H-pyrazol-3-yl]-methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
99 N-[[2-butoxy-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]-2-[3-fluoro-4-(hydroxymethyl)phenyl]propionamide;
100 N-[[2-butoxy-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
101 N-[[2-butoxy-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]-2-[4-(methanesulphonamido)-3-methoxyphenyl]propionamide;
102 N-[(2-butoxy-5-tert-butyl-2H-pyrazol-3-yl)-methyl]-2-(3-fluorophenyl)acetamide;
103 N-[[2-cyclopentyloxy-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
104 N-[[2-cyclopentyloxy-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]-2-[4-(methanesulphonamido)-3-methoxyphenyl]propionamide;
105 2-(3-fluorophenyl)-N-[[2-[(4-methoxyphenyl)methoxy]-5-(trifluoromethyl)-2H-pyrazol-3-yl]methyl]acetamide;
107 N-[[2-(cyclohexylsulphanyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
108 N-[[2-(benzenesulphonyl)-5-tert-butyl-2H-pyrazol-3-yl]-methyl]-2-(3-fluorophenyl)acetamide;
109 N-[[2-cyclohexyl-5-(trifluoromethyl)-2H-[1,2,4]triazol-3-yl]methyl]-2-[4-(methanesulphonamido)-3-methoxyphenyl]propionamide;
110 N-[[2-cyclohexyl-5-(trifluoromethyl)-2H-[1,2,4]triazol-3-yl]methyl]-2-(3-fluorophenyl)acetamide;
111 4-[1-[[2-cyclohexyl-5-(trifluoromethyl)-2H-[1,2,4]triazol-3-yl]-methylcarbamoyl]ethyl]-2-fluorobenzamide;
112 2-[3-fluoro-4-(hydroxymethyl)phenyl]-N-[[2-hexyl-5-(trifluoromethyl)-2H-[1,2,4]triazol-3-yl]methyl]propionamide;
113 4-[1-[[2-cyclobutyl-5-(trifluoromethyl)-2H-[1,2,4]triazol-3-yl]-methylcarbamoyl]ethyl]-2-fluorobenzamide;
114 N-[[5-tert-butyl-2-(3,3-difluorocyclobutanecarbonyl)-2H-[1,2,4]triazol-3-yl]-methyl]-2-[3-fluoro-4-(methanesulphonamido)phenyl]propionamide;
116 N-[[2-(benzenesulphonyl)-5-tert-butyl-2H-[1,2,4]triazol-3-yl]methyl]-2-(3-fluorophenyl)acetamide;
117 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluorophenyl)-2-methylpropanamide;
118 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-1-(3-fluorophenyl)cyclopropancarboxamide;
119 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-1-(3-fluorophenyl)cyclobutancarboxamide;
120 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-1-(3-fluorophenyl)cyclopentancarboxamide;
121 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-1-(3-fluorophenyl)cyclohexancarboxamide;
122 1-((3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluorophenyl)urea
123 3-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-1-(3-fluorophenyl)-1-methylurea;
124 N-((1-(3-chloro-4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulfonylmethyl)phenyl)propanamide;
125 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(4-cyclopropyl-3-fluorophenyl)propanamide;
126 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(4-cyclopropyl-3-fluorophenyl)urea;
127 N-((3-tert-butyl-1-(pyridin-2-yl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidmethyl)phenyl)propanamide;
128 N-((1-(3-chlorophenyl)-3-cyclopropyl-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulfonylmethyl)phenyl)propanamide;
129 2-(3-fluoro-4-(methylsulfonamidmethyl)phenyl)-N-((1-(pyridin-2-ylmethylamino)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)propanamide;
130 N-((1-(3-chlorophenyl)-4-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluorophenyl)acetamide;
131 2-(3-fluorophenyl)-N-((1-pentyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)acetamide;
132 2-(3-fluorophenyl)-N-((1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)acetamide;
133 N-((3-tert-butyl-1-(2,2,2-trifluoroethylamino)-1H-pyrazol-5-yl)methyl)-2-(3-fluorophenyl)acetamide;
134 N-((1-(3-chlorophenyl)-4-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidmethyl)phenyl)propanamide;
135 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-1,2,4-triazol-5-yl)methyl)-2-(3-fluorophenyl)acetamide;
136 2-(3-fluorophenyl)-N-((1-(pyridin-3-yl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)acetamide;
137 N-((1-cyclohexyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidmethyl)phenyl)propanamide;
138 2-(3-fluoro-4-(methylsulfonamidmethyl)phenyl)-N-((1-(tetrahydro-2H-pyran-4-yl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)propanamide;
139 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(4-(cyclopropylethynyl)-3-fluorophenyl)urea;
140 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamide;
141 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)propanamide;
142 N-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-((2-methoxyethoxy)methyl)phenyl)propanamide;
143 4-(1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylamino)-1-oxopropan-2-yl)-N-phenylbenzamide;
144 1-((3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-morpholinphenyl)urea;
145 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3-fluoro-4-(methylsulfonamid)phenyl)-3-phenylpropanamide;
146 N-(5-((2-(3-fluorophenyl)acetamide)methyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzamide; and
147 N-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-2-(3,5-difluoro-4-hydroxyphenyl)acetamide;
respectively in the form of the free compounds; the racemate; the enantiomers, diastereomers, mixtures of the enantiomers or diastereomers or of an individual enantiomer or diastereomer; or in the form of the salts of physiologically compatible acids or bases.
11. Pharmaceutical composition containing at least one substituted compound according to claim 1 ,
in the form of an individual stereoisomer or the mixture thereof, the free compounds and/or their physiologically compatible salts, and also if appropriate suitable additives and/or auxiliaries and/or if appropriate further active ingredients.