US 7,741,354 B2 · Inhibitors of glutaminyl cyclase

Abstract

The present invention relates to compounds of formula (I), combinations and uses thereof for disease therapy, wherein: R1 represents heteroaryl, -carbocyclyl-heteroaryl, -alkenylheteroaryl or -alkylheteroaryl; R2 represents alkyl, which may optionally be substituted by one or more groups selected from amino, halogen, hydroxyl, -alkoxy, -thioalkyl, —C(O)O-alkyl and —C(O)OH; carbocyclyl, which may optionally be substituted by one or more groups selected from alkyl, haloalkyl, amino, halogen, hydroxyl, alkoxy-, -thioalkyl, —C(O)O-alkyl and —C(O)OH; alkenyl; alkynyl; -alkyl-aryl; -alkyl-heteroaryl; -alkyl-heterocyclyl; -alkyl-carbocyclyl; -aryl-heteroaryl; -heteroaryl-aryl; -heteroaryl-heteroaryl; -aryl-aryl; -aryl (monocyclic or bicyclic); heteroaryl (monocyclic or bicyclic); heterocyclyl; or R2 together with R4 may form a carbocyclyl group optionally substituted by one or more alkyl groups; R3 represents alkyl, which may optionally be substituted by one or more groups selected from amino, halogen, hydroxyl, alkoxy-, -thioalkyl, —C(O)OH and —C(O)O-alkyl; carbocyclyl, which may optionally be substituted by one or more groups selected from alkyl, amino, halogen, haloalkyl, hydroxyl, -alkoxy, -thioalkyl, —C(O)OH and —C(O)O-alkyl; alkenyl; -alkyl-aryl; -alkyl(aryl)2, -alkyl(heteroaryl)2, -alkyl(aryl)(heteroaryl), -alkyl-heteroaryl; -alkyl-heterocyclyl which heterocyclyl group may optionally be substituted by one or more groups selected from alkyl, hydroxy and oxo ; -alkyl-carbocyclyl; -aryl-heteroaryl; -heteroaryl-aryl; -aryl-aryl; -aryl-O-aryl, -heteroaryl-heteroaryl; -aryl; heteroaryl; heterocyclyl; -aryl-alkyl-aryl; -aryl-O-alkyl-aryl; -alkyl-C(O)—NH-alkyl-aryl; -alkyl-C(O)—NH-alkyl-heteroaryl; -alkyl-C(O)—NH-alkyl-heterocyclyl; -alkyl-C(O)—(N-piperidinyl) or -alkyl-C(O)—(N-pyrrolidinyl) in which piperidinyl or pyrrolidinyl may optionally be fused to optionally substituted phenyl. R4 represents H or alkyl.

Claims23

Dependent claims

A compound of formula (I)

wherein
R1 represents heteroaryl, -carbocyclyl-heteroaryl, -alkenylheteroaryl or -alkylheteroaryl;
R2 represents alkyl, which may optionally be substituted by one or more groups selected from amino, halogen, hydroxyl, -alkoxy, -thioalkyl, —C(O)O-alkyl and —C(O)OH;
carbocyclyl, which may optionally be substituted by one or more groups selected from alkyl, haloalkyl, amino, halogen, hydroxyl, alkoxy-, -thioalkyl, —C(O)O-alkyl and —C(O)OH;
alkenyl;
alkynyl;
-alkyl-aryl;
-alkyl-heteroaryl;
-alkyl-heterocyclyl;
-alkyl-carbocyclyl;
-aryl-heteroaryl;
-heteroaryl-aryl;
-heteroaryl-heteroaryl;
-aryl-aryl;
-aryl;
heteroaryl;
heterocyclyl;
or R2 together with R4 may form a carbocyclyl group optionally substituted by one or more alkyl groups;
R3 represents alkyl, which may optionally be substituted by one or more groups selected from amino, halogen, hydroxyl, alkoxy-, -thioalkyl, —C(O)OH and —C(O)O-alkyl;
carbocyclyl, which may optionally be substituted by one or more groups selected from alkyl, amino, halogen, haloalkyl, hydroxyl, -alkoxy, -thioalkyl, —C(O)OH and —C(O)O-alkyl;
alkenyl;
-alkyl-aryl;
-alkyl(aryl)2, -alkyl(heteroaryl)2, -alkyl(aryl)(heteroaryl), -alkyl-heteroaryl;
-alkyl-heterocyclyl which heterocyclyl group may optionally be substituted by one or more groups selected from alkyl, hydroxyl and oxo;
-alkyl-carbocyclyl;
-aryl-heteroaryl;
-heteroaryl-aryl;
-aryl-aryl;
-aryl-O-aryl;
-heteroaryl-heteroaryl;
-aryl;
heteroaryl;
heterocyclyl;
-aryl-alkyl-aryl;
-aryl-O-alkyl-aryl;
-alkyl-C(O)—NH-alkyl-aryl;
-alkyl-C(O)—NH-alkyl-heteroaryl;
-alkyl-C(O)—NH-alkyl-heterocyclyl;
-alkyl-C(O)—(N-piperidinyl) or -alkyl-C(O)—(N-pyrrolidinyl) in which piperidinyl or pyrrolidinyl may optionally be fused to optionally substituted phenyl;
R4 represents H or alkyl;
or a pharmaceutically acceptable salt thereof, including all tautomers and stereoisomers thereof.

38 more elements

A compound selected from the group consisting of examples 1-212 below and the pharmaceutically acceptable salts and solvates of them:

Example 1 [[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-(3,4-dichloro-phenyl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 2 [[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-(2,4-dimethyl-phenyl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 3 2-[[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol,
Example 4 2-[[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol,
Example 5 5-[[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-2-fluoro-benzonitrile,
Example 6 [[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-(1H-indol-5-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 7 {[-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-quinolin-2-yl-methyl}-(3-imidazol-1-yl-propyl)-amine,
Example 8 [[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-((S)-2-methyl-cyclohex-2-enyl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 9 {(S)-[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-3,4-dihydro-2H-pyran-2-yl-methyl}-(3-imidazol-1-yl-propyl)-amine,
Example 10 ((3,4-Dichloro-phenyl)-{1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-tetrazol-5-yl}-methyl)-(3-imidazol-1-yl-propyl)-amine,
Example 11 2-((3-Imidazol-1-yl-propylamino)-{1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-tetrazol-5-yl}-methyl)-4-methyl-phenol,
Example 12 2-((3-Imidazol-1-yl-propylamino)-{1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-tetrazol-5-yl}-methyl)-quinolin-8-ol,
Example 13 (3-Imidazol-1-yl-propyl)-((1H-indol-5-yl)-{1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-tetrazol-5-yl}-methyl)-amine
Example 14 (3-Imidazol-1-yl-propyl)-(quinolin-2-yl-{1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-tetrazol-5-yl}-methyl)-amine,
Example 15 (Benzofuran-2-yl-{1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-tetrazol-5-yl}-methyl)-(3-imidazol-1-yl-propyl)-amine,
Example 16 (3-Imidazol-1-yl-propyl)-((6-methyl-1H-indol-3-yl)-{1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-tetrazol-5-yl}-methyl)-amine,
Example 17 (3-Imidazol-1-yl-propyl)-[{1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-tetrazol-5-yl}-(2,4,5-trimethyl-phenyl)-methyl]-amine,
Example 18 [(1-Butyl-1H-tetrazol-5-yl)-(3,4-dichloro-phenyl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 19 2-[(1-Butyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol,
Example 20 2-[(1-Butyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol,
Example 21 [(1-Butyl-1H-tetrazol-5-yl)-(1H-indol-5-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine
Example 22 [(1-Butyl-1H-tetrazol-5-yl)-quinolin-2-yl-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 23 [Benzofuran-2-yl-(1-butyl-1H-tetrazol-5-yl)-methyl]-(3-imidazol-1-yl propyl)-amine,
Example 24 [(1-Butyl-1H-tetrazol-5-yl)-(2,4,5-trimethyl-phenyl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 25 2-[(1-Cyclopentyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol,
Example 26 [(1-Cyclopentyl-1H-tetrazol-5-yl)-(1H-indol-5-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 27 [(1-Cyclopentyl-1H-tetrazol-5-yl)-((S)-2-methyl-cyclohex-2-enyl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 28 [(S)-(1-Cyclopentyl-1H-tetrazol-5-yl)-3,4-dihydro-2H-pyran-2-yl-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 29 2-[(3-Imidazol-1-yl-propylamino)-(1-methyl-1H-tetrazol-5-yl)-methyl]-quinolin-8-ol,
Example 30 (3-Imidazol-1-yl-propyl)-[(1H-indol-5-yl)-(1-methyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 31 (3-Imidazol-1-yl-propyl)-[(1-methyl-1H-tetrazol-5-yl)-quinolin-2-yl-methyl]-amine,
Example 32 {(3,4-Dichloro-phenyl)-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-methyl}-(3-imidazol-1-yl-propyl)-amine,
Example 33 2-{(3-Imidazol-1-yl-propylamino)-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-methyl}-4-methyl-phenol,
Example 34 2-{(3-Imidazol-1-yl-propylamino)-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-methyl}-quinolin-8-ol,
Example 35 (3-Imidazol-1-yl-propyl)-{(1H-indol-5-yl)-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 36 (3-Imidazol-1-yl-propyl)-{[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-quinolin-2-yl-methyl}-amine,
Example 37 2-[[1-(2-Dimethylamino-ethyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol,
Example 38 {(S)-3,4-Dihydro-2H-pyran-2-yl-[1-(2-dimethylamino-ethyl)-1H-tetrazol-5-yl]-methyl}-(3-imidazol-1-yl-propyl)-amine,
Example 39 2-{(3-Imidazol-1-yl-propylamino)-[1-(2-methoxy-ethyl)-1H-tetrazol-5-yl]-methyl}-4-methyl-phenol,
Example 40 2-{(3-Imidazol-1-yl-propylamino)-[1-(2-methoxy-ethyl)-1H-tetrazol-5-yl]-methyl}-quinolin-8-ol,
Example 41 (3-Imidazol-1-yl-propyl)-{(1H-indol-5-yl)-[1-(2-methoxy-ethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 42 (3-Imidazol-1-yl-propyl)-{[1-(2-methoxy-ethyl)-1H-tetrazol-5-yl]-quinolin-2-yl-methyl}-amine,
Example 43 (3-Imidazol-1-yl-propyl)-[[1-(2-methoxy-ethyl)-1H-tetrazol-5-yl]-(2,4,5-trimethyl-phenyl)-methyl]-amine,
Example 44 2-[(1-Allyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol,
Example 45 2-[(1-Allyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol,
Example 46 [(1-Allyl-1H-tetrazol-5-yl)-(1H-indol-5-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 47 [(1-Allyl-1H-tetrazol-5-yl)-quinolin-2-yl-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 48 [(1-Allyl-1H-tetrazol-5-yl)-(2,4,5-trimethyl-phenyl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 49 {5-[1-(3-Imidazol-1-yl-propylamino)-cyclobutyl]-tetrazol-1-yl}-acetic methyl ester,
Example 50 {5-[(3,4-Dichloro-phenyl)-(3-imidazol-1-yl-propylamino)-methyl]-tetrazol-1-yl}-acetic methyl ester,
Example 51 {5-[(2-Hydroxy-5-methyl-phenyl)-(3-imidazol-1-yl-propylamino)-methyl]-tetrazol-1-yl}-acetic methyl ester,
Example 52 {5-[(8-Hydroxy-quinolin-2-yl)-(3-imidazol-1-yl-propylamino)-methyl]tetrazol-1-yl}-acetic methyl ester,
Example 53 {5-[(3-Cyano-4-fluoro-phenyl)-(3-imidazol-1-yl-propylamino)-methyl]-tetrazol-1-yl}-acetic methyl ester,
Example 54 {5-[(3-Imidazol-1-yl-propylamino)-(1H-indol-5-yl)-methyl]-tetrazol-1-yl}-acetic methyl ester,
Example 55 {5-[(3-Imidazol-1-yl-propylamino)-quinolin-2-yl-methyl]-tetrazol-1-yl}-acetic methyl ester,
Example 56 {5-[(S)-3,4-Dihydro-2H-pyran-2-yl-(3-imidazol-1-yl-propylamino)-methyl]-tetrazol-1-yl}-acetic methyl ester,
Example 57 {5-[Cyclopropyl-(3-imidazol-1-yl-propylamino)-methyl]-tetrazol-1-yl}-acetic methyl ester,
Example 58 {5-[(3-Hydroxy-4-methoxy-phenyl)-(3-imidazol-1-yl-propylamino)-methyl]-tetrazol-1-yl}-acetic methyl ester,
Example 59 2-[(1-tert-Butyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol,
Example 60 2-[(1-tert-Butyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol,
Example 61 [(S)-(1-tert-Butyl-1H-tetrazol-5-yl)-3,4-dihydro-2H-pyran-2-yl-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 62 [(1-tert-Butyl-1H-tetrazol-5-yl)-(2,4-dimethoxy-pyrimidin-5-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 63 2-[[1-(2,2-Dimethyl-propyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol,
Example 64 2-[[1-(2,2-Dimethyl-propyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol,
Example 65 [[1-(2,2-Dimethyl-propyl)-1H-tetrazol-5-yl]-(1H-indol-5-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 66 {[1-(2,2-Dimethyl-propyl)-1H-tetrazol-5-yl]-quinolin-2-yl-methyl}-(3-imidazol-1-yl-propyl)-amine,
Example 67 {(S)-3,4-Dihydro-2H-pyran-2-yl-[1-(2,2-dimethyl-propyl)-1H-tetrazol-5-yl]-methyl}-(3-imidazol-1-yl-propyl)-amine,
Example 68 2-[(1-Cyclopropyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol,
Example 69 [(1-Cyclopropyl-1H-tetrazol-5-yl)-(1H-indol-5-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 70 [(1-Cyclopropyl-1H-tetrazol-5-yl)-quinolin-2-yl-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 71 [(S)-(1-Cyclopropyl-1H-tetrazol-5-yl)-3,4-dihydro-2H-pyran-2-yl-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 72 (1H-Benzoimidazol-5-yl)-[(1-cyclohexyl-1H-tetrazol-5-yl)-(4-methoxy-phenyl)-methyl]-amine,
Example 73 (1H-Benzoimidazol-5-yl)-[2-phenyl-1-(1-pyridin-3-ylmethyl-1H-tetrazol-5-yl)-ethyl]-amine,
Example 74 (1H-Benzoimidazol-5-yl)-[(3-propoxy-phenyl)-(1-pyridin-3-ylmethyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 75 (1H-Benzoimidazol-5-yl)-[[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-(4-methoxy-2-methyl-phenyl)-methyl]-amine,
Example 76 (1H-Benzoimidazol-5-yl)-{(4-pyridin-2-yl-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 77 (1H-Benzoimidazol-5-yl)-[[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-(4-methoxy-2-methyl-phenyl)-methyl]-amine,
Example 78 {Benzo[b]thiophen-3-yl-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-(1H-benzoimidazol-5-yl)-amine,
Example 79 [Benzofuran-2-yl-(1-cyclohexyl-1H-tetrazol-5-yl)-methyl]-(1H-benzoimidazol-5-yl)-amine,
Example 80 (1H-Benzoimidazol-5-yl)-{(6-methyl-1H-indol-3-yl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 81 (1H-Benzoimidazol-5-yl)-[(1-cyclohexyl-1H-tetrazol-5-yl)-(6-fluoro-1H-indol-3-yl)-methyl]-amine,
Example 82 (1H-Benzoimidazol-5-yl)-[(4-ethyl-phenyl)-(1-pyridin-3-ylmethyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 83 (1H-Benzoimidazol-5-yl)-{(3,4-dimethyl-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 84 2-{5-[(1H-Benzoimidazol-5-ylamino)-(4-chloro-3-fluoro-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 85 3-{(1H-Benzoimidazol-5-ylamino)-[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-benzoic acid methyl ester,
Example 86 3-{(1H-Benzoimidazol-5-ylamino)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-6-methyl-chromen-4-one,
Example 87 {5-[(1H-Benzoimidazol-5-ylamino)-(4-bromo-phenyl)-methyl]-tetrazol-1-yl}-acetic acid tert-butyl ester,
Example 88 (1H-Benzoimidazol-5-yl)-{(4-methoxy-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 89 (1H-Benzoimidazol-5-yl)-{(3-methoxy-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 90 {Benzofuran-2-yl-[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-(1H-benzoimidazol-5-yl)-amine,
Example 91 {5-[(1H-Benzoimidazol-5-ylamino)-(4-chloro-3-fluoro-phenyl)-methyl]-tetrazol-1-yl}-acetic acid tert-butyl ester,
Example 92 (1H-Benzoimidazol-5-yl)-{(2E,4E)-1-[1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-tetrazol-5-yl]-hexa-2,4-dienyl}-amine,
Example 93 {3-Benzo[1,3]dioxol-5-yl-2-methyl-1-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-propyl}-(1H-benzoimidazol-5-yl)-amine,
Example 94 2-{5-[(1H-Benzoimidazol-5-ylamino)-(4-chloro-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 95 [1-(1-Benzhydryl-1H-tetrazol-5-yl)-3-methylsulfanyl-propyl]-(1H-benzoimidazol-5-yl)-amine,
Example 96 (1H-Benzoimidazol-5-yl)-[1-(1-cyclohexyl-1H-tetrazol-5-yl)-3-(5-methyl-furan-2-yl)-butyl]-amine,
Example 97 (1H-Benzoimidazol-5-yl)-{3-phenyl-1-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-butyl}-amine,
Example 98 2-{5-[1-(1H-Benzoimidazol-5-ylamino)-2-methyl-pentyl]-tetrazol-1-yl}-1-(3,4-dihydro-1H-isoquinolin-2-yl)-ethanone,
Example 99 (1H-Benzoimidazol-5-yl)-[(1-tert-butyl-1H-tetrazol-5-yl)-(4-methoxy-2,5-dimethyl-phenyl)-methyl]-amine,
Example 100 (1H-Benzoimidazol-5-yl)-{2-phenyl-1-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-propyl}-amine,
Example 101 {Benzofuran-2-yl-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-(1H-benzoimidazol-5-yl)-amine,
Example 102 (1H-Benzoimidazol-5-yl)-{quinolin-3-yl-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 103 2-{5-[(1H-Benzoimidazol-5-ylamino)-(4-bromo-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 104 2-{(1H-Benzoimidazol-5-ylamino)-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-methyl}-cyclopropanecarboxylic acid ethyl ester,
Example 105 (1H-Benzoimidazol-5-yl)-{benzo[c][1,2,5]thiadiazol-5-yl-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 106 (1H-Benzoimidazol-5-yl)-[1-(1-tert-butyl-1H-tetrazol-5-yl)-3-phenyl-butyl]-amine,
Example 107 (1H-Benzoimidazol-5-yl)-[(4-chloro-3-fluoro-phenyl)-(1-cyclohexyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 108 (1H-Benzoimidazol-5-yl)-{(4-dimethylamino-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 109 (1H-Benzoimidazol-5-yl)-{(3-bromo-4-methoxy-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 110 (1H-Benzoimidazol-5-yl)-[1-(1-benzyl-1H-tetrazol-5-yl)-butyl]-amine,
Example 111 (1H-Benzoimidazol-5-yl)-{3-(5-methyl-furan-2-yl)-1-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-butyl}-amine,
Example 112 [(1-Benzhydryl-1H-tetrazol-5-yl)-benzo[c][1,2,5]thia-diazol-5-yl-methyl]-(1H-benzoimidazol-5-yl)-amine,
Example 113 {3-Benzo[1,3]dioxol-5-yl-1-[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-2-methyl-propyl}-(1H-benzoimidazol-5-yl)-amine,
Example 114 (1H-Benzoimidazol-5-yl)-[(1-cyclohexyl-1H-tetrazol-5-yl)-(3,4-dihydro-2H-pyran-2-yl)-methyl]-amine,
Example 115 (1H-Benzoimidazol-5-yl)-[(4-dimethylamino-phenyl)-(1-pyridin-3-ylmethyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 116 [3-Benzo[1,3]dioxol-5-yl-1-(1-cyclohexyl-1H-tetrazol-5-yl)-2-methyl-propyl]-(1H-benzoimidazol-5-yl)-amine,
Example 117 (1H-Benzoimidazol-5-yl)-{benzo[c][1,2,5]thiadiazol-5-yl-[1-(4-tert-butyl-phenyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 118 {Benzo[1,3]dioxol-5-yl-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-(1H-benzoimidazol-5-yl)-amine,
Example 119 {5-[Benzo[1,3]dioxol-5-yl-(1H-benzoimidazol-5-ylamino)-methyl]-tetrazol-1-yl}-acetic acid tert-butyl ester,
Example 120 2-{5-[(1H-Benzoimidazol-5-ylamino)-thiophen-2-yl-methyl]-tetrazol-1-yl}-1-(3,4-dihydro-1H-isoquinolin-2-yl)-ethanone,
Example 121 (5-{(1H-Benzoimidazol-5-ylamino)-[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-furan-2-yl)-methanol,
Example 122 3-{(1H-Benzoimidazol-5-ylamino)-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-methyl}-chromen-4-one,
Example 123 [Benzo[b]thiophen-3-yl-(1-tert-butyl-1H-tetrazol-5-yl)-methyl]-(1H-benzoimidazol-5-yl)-amine,
Example 124 (1H-Benzoimidazol-5-yl)-[(1-benzyl-1H-tetrazol-5-yl)-(3,5-dimethyl-phenyl)-methyl]-amine,
Example 125 (1H-Benzoimidazol-5-yl)-[[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-(3-fluoro-4-methoxy-phenyl)-methyl]-amine,
Example 126 [(1-Benzhydryl-1H-tetrazol-5-yl)-quinolin-3-yl-methyl]-(1H-benzoimidazol-5-yl)-amine,
Example 127 (1H-Benzoimidazol-5-yl)-[[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-(4-chloro-phenyl)-methyl]-amine,
Example 128 3-{(1H-Benzoimidazol-5-ylamino)-[1-(4-tert-butyl-phenyl)-1H-tetrazol-5-yl]-methyl}-benzoic acid methyl ester,
Example 129 (1H-Benzoimidazol-5-yl)-{(5-ethyl-thiophen-2-yl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 130 (1H-Benzoimidazol-5-yl)-[[1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-tetrazol-5-yl]-(4-methylsulfanyl-phenyl)-methyl]-amine,
Example 131 4-{(1H-Benzoimidazol-5-ylamino)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-2,6-dimethyl-phenol,
Example 132 2-{5-[(1H-Benzoimidazol-5-ylamino)-(3-fluoro-4-methoxy-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 133 (1H-Benzoimidazol-5-yl)-[(1-benzyl-1H-tetrazol-5-yl)-(5-ethyl-thiophen-2-yl)-methyl]-amine,
Example 134 (1H-Benzoimidazol-5-yl)-{(4-pyrrolidin-1-yl-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 135 (1H-Benzoimidazol-5-yl)-{[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-pyridin-3-yl-methyl}-amine,
Example 136 (1H-Benzoimidazol-5-yl)-[[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-(4-chloro-phenyl)-methyl]-amine,
Example 137 2-{5-[(1H-Benzoimidazol-5-ylamino)-(3,5-dimethyl-phenyl)-methyl]-tetrazol-1-yl}-1-(3,4-dihydro-1H-isoquinolin-2-yl)-ethanone,
Example 138 {Benzo[1,3]dioxol-5-yl-[1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-tetrazol-5-yl]-methyl}-(1H-benzoimidazol-5-yl)-amine,
Example 139 {Benzo[1,3]dioxol-5-yl-[1-(4-phenoxy-phenyl)-1H-tetrazol-5-yl]-methyl}-(1H-benzoimidazol-5-yl)-amine,
Example 140 (1H-Benzoimidazol-5-yl)-{(4-methylsulfanyl-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 141 (1H-Benzoimidazol-5-yl)-{(3-propoxy-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 142 (1H-Benzoimidazol-5-yl)-[(3-bromo-4-methoxy-phenyl)-(1-pyridin-3-ylmethyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 143 (5-{(1H-Benzoimidazol-5-ylamino)-[1-(2-benzyloxy-phenyl)-1H-tetrazol-5-yl]-methyl}-furan-2-yl)-methanol,
Example 144 (1H-Benzoimidazol-5-yl)-{(6-fluoro-1H-indol-3-yl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 145 2-{5-[Benzo[b]thiophen-3-yl-(1H-benzoimidazol-5-ylamino)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 146 (1H-Benzoimidazol-5-yl)-{(4-chloro-3-nitro-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 147 (1H-Benzoimidazol-5-yl)-[benzo[c][1,2,5]thiadiazol-5-yl-(1-benzyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 148 (1H-Benzoimidazol-5-yl)-[[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-(4-chloro-3-nitro-phenyl)-methyl]-amine
Example 149 {5-[3-Benzo[1,3]dioxol-5-yl-1-(1H-benzoimidazol-5-ylamino)-2-methyl-propyl]-tetrazol-1-yl}-acetic acid tert-butyl ester,
Example 150 2-{5-[(1H-Benzoimidazol-5-ylamino)-(4-methylsulfanyl-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 151 (1H-Benzoimidazol-5-yl)-[(1-benzyl-1H-tetrazol-5-yl)-(2-methoxy-phenyl)-methyl]-amine,
Example 152 3-{(1H-Benzoimidazol-5-ylamino)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-phenol,
Example 153 (1H-Benzoimidazol-5-yl)-[[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-(2-methoxy-phenyl)-methyl]-amine,
Example 154 3-{(1H-Benzoimidazol-5-ylamino)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-benzoic acid methyl ester,
Example 155 2-{5-[(1H-Benzoimidazol-5-ylamino)-(3,4-dimethyl-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 156 (1H-Benzoimidazol-5-yl)-{[1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-tetrazol-5-yl]-quinolin-3-yl-methyl}-amine,
Example 157 2-{5-[(1H-Benzoimidazol-5-ylamino)-(3,5-dimethyl-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 158 [(1-Benzhydryl-1H-tetrazol-5-yl)-pyridin-3-yl-methyl]-(1H-benzoimidazol-5-yl)-amine,
Example 159 3-{(1H-Benzoimidazol-5-ylamino)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-chromen-4-one,
Example 160 {Benzo[1,3]dioxol-5-yl-[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-(1H-benzoimidazol-5-yl)-amine,
Example 161 (1H-Benzoimidazol-5-yl)-{(2E,4E)-1-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-hexa-2,4-dienyl}-amine,
Example 162 2-{5-[Benzo[1,3]dioxol-5-yl-(1H-benzoimidazol-5-ylamino)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 163 (1H-Benzoimidazol-5-yl)-{(3-fluoro-4-methoxy-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 164 1-(3-{5-[(1H-Benzoimidazol-5-ylamino)-(3,4-dimethyl-phenyl)-methyl]-tetrazol-1-yl}-propyl)-pyrrolidin-2-one,
Example 165 4-{(1H-Benzoimidazol-5-ylamino)-[1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-tetrazol-5-yl]-methyl}-2,6-dimethyl-phenol,
Example 166 (1H-Benzoimidazol-5-yl)-{benzo[c][1,2,5]thiadiazol-5-yl-[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 167 (1H-Benzoimidazol-5-yl)-{cyclohex-3-enyl-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 168 2-{5-[(1H-Benzoimidazol-5-ylamino)-(4-ethyl-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 169 2-{5-[(1H-Benzoimidazol-5-ylamino)-(5-chloro-2-hydroxy-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 170 (1H-Benzoimidazol-5-yl)-{(3,5-dibromo-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 171 (1H-Benzoimidazol-5-yl)-{(4-chloro-3-nitro-phenyl)-[1-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 172 {5-[(1H-Benzoimidazol-5-ylamino)-(4-methoxy-phenyl)-methyl]-tetrazol-1-yl}-acetic acid tert-butyl ester,
Example 173 (1H-Benzoimidazol-5-yl)-[(2E,4E)-1-(1-pyridin-3-ylmethyl-1H-tetrazol-5-yl)-hexa-2,4-dienyl]-amine,
Example 174 (1H-Benzoimidazol-5-yl)-{(2E,4E)-1-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-hexa-2,4-dienyl}-amine,
Example 175 (1H-Benzoimidazol-5-yl)-[(1-cyclohexyl-1H-tetrazol-5-yl)-(3,5-dibromo-phenyl)-methyl]-amine,
Example 176 1-(3-{5-[(1H-Benzoimidazol-5-ylamino)-(3,5-dibromo-phenyl)-methyl]-tetrazol-1-yl}-propyl)-pyrrolidin-2-one,
Example 177 (1H-Benzoimidazol-5-yl)-{(3,5-dibromo-phenyl)-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 178 (1H-Benzoimidazol-5-yl)-{(3,5-dibromo-phenyl)-[1-(4-phenoxy-phenyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 179 (1H-Benzoimidazol-5-yl)-{(3,5-dibromo-phenyl)-[1-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 180 (1H-Benzoimidazol-5-yl)-[[1-(2-benzyloxy-phenyl)-1H-tetrazol-5-yl]-(3,5-dibromo-phenyl)-methyl]-amine,
Example 181 (1H-Benzoimidazol-5-yl)-{benzo[c][1,2,5]thiadiazol-5-yl-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 182 (1H-Benzoimidazol-5-yl)-{(3,4-dihydro-2H-pyran-2-yl)-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 183 2-{5-[(1H-Benzoimidazol-5-ylamino)-(2-methoxy-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 184 2-{5-[(1H-Benzoimidazol-5-ylamino)-(4-methoxy-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 185 (1H-Benzoimidazol-5-yl)-[benzo[c][1,2,5]thiadiazol-5-yl-(1-pyridin-3-ylmethyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 186 [(1-Benzhydryl-1H-tetrazol-5-yl)-(3,5-dibromo-phenyl)-methyl]-(1H-benzoimidazol-5-yl)-amine,
Example 187 2-{5-[(1H-Benzoimidazol-5-ylamino)-(3,5-dibromo-phenyl)-methyl]-tetrazol-1-yl}-N-[2-(1H-indol-3-yl)-ethyl]-acetamide,
Example 188 (1H-Benzoimidazol-5-yl)-{(3,5-dibromo-phenyl)-[1-(3,3-diphenyl-propyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 189 (1H-Benzoimidazol-5-yl)-{(3,5-dibromo-phenyl)-[1-(4-phenyl-butyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 190 (1H-Benzoimidazol-5-yl)-[(1-benzyl-1H-tetrazol-5-yl)-(3,5-dibromo-phenyl)-methyl]-amine,
Example 191 4-{(1H-Benzoimidazol-5-ylamino)-[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-phenol,
Example 192 2-{5-[(1H-Benzoimidazol-5-ylamino)-(3-methoxy-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 193 2-[(1H-Benzoimidazol-5-ylamino)-(1-cyclohexyl-1H-tetrazol-5-yl)-methyl]-4-chloro-phenol,
Example 194 1-(3-{5-[(1H-Benzoimidazol-5-ylamino)-(4-bromo-phenyl)-methyl]-tetrazol-1-yl}-propyl)-pyrrolidin-2-one,
Example 195 3-{(1H-Benzoimidazol-5-ylamino)-[1-(2-ethoxycarbonyl-cyclohexyl)-1H-tetrazol-5-yl]-methyl}-benzoic acid methyl ester,
Example 196 2-{5-[(1H-Benzoimidazol-5-ylamino)-(6-methyl-1H-indol-3-yl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 197 (1H-Benzoimidazol-5-yl)-[[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-(4-chloro-3-nitro-phenyl)-methyl]-amine,
Example 198 (1H-Benzoimidazol-5-yl)-[(1-cyclohexyl-1H-tetrazol-5-yl)-(4-ethyl-phenyl)-methyl]-amine,
Example 199 2-{5-[(1H-Benzoimidazol-5-ylamino)-(4-bromo-phenyl)-methyl]-tetrazol-1-yl}-1-(3,4-dihydro-1H-isoquinolin-2-yl)-ethanone,
Example 200 2-{5-[(1H-Benzoimidazol-5-ylamino)-(4-bromo-phenyl)-methyl]-tetrazol-1-yl}-N-[2-(1H-indol-3-yl)-ethyl]-acetamide,
Example 201 (1H-Benzoimidazol-5-yl)-[(4-bromo-phenyl)-(1-pyridin-3-ylmethyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 202 2-{5-[1-(1H-Benzoimidazol-5-ylamino)-3-(5-methyl-furan-2-yl)-butyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 203 (1H-Benzoimidazol-5-yl)-[[1-(2-benzyloxy-phenyl)-1H-tetrazol-5-yl]-(4-bromo-phenyl)-methyl]-amine,
Example 204 (1H-Benzoimidazol-5-yl)-{1-[1-(4-phenoxy-phenyl)-1H-tetrazol-5-yl]-3-phenyl-butyl}-amine,
Example 205 (1H-Benzoimidazol-5-yl)-{benzo[c][1,2,5]thiadiazol-5-yl-[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 206 {Benzo[b]thiophen-3-yl-[1-(4-nitro-phenyl)-1H-tetrazol-5-yl]-methyl}-(1H-benzoimidazol-5-yl)-amine,
Example 207 (1H-Benzoimidazol-5-yl)-{(4-chloro-3-fluoro-phenyl)-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 208 2-{5-[(1H-Benzoimidazol-5-ylamino)-(3-propoxy-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 209 2-{5-[(1H-Benzoimidazol-5-ylamino)-(4-methoxy-phenyl)-methyl]-tetrazol-1-yl}-1-(3,4-dihydro-1H-isoquinolin-2-yl)-ethanone,
Example 210 (1H-Benzoimidazol-5-yl)-[[1-(2-benzyloxy-phenyl)-1H-tetrazol-5-yl]-(4-methoxy-phenyl)-methyl]-amine,
Example 211 (1H-Benzoimidazol-5-yl)-{(4-pyridin-2-yl-phenyl)-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 212 {5-[(1H-Benzoimidazol-5-ylamino)-(4-pyridin-2-yl-phenyl)-methyl]-tetrazol-1-yl}-acetic acid tert-butyl ester.

209 more elements

A compound selected from the group consisting of examples below and the pharmaceutically acceptable salts of them:

Example 1 [[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-(3,4-dichloro-phenyl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 6 [[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-(1H-indol-5-yl)-methyl]-(3-imidazol-1-yl-propyl)-amine,
Example 7 {[1-(4-Chloro-benzyl)-1H-tetrazol-5-yl]-quinolin-2-yl-methyl}-(3-imidazol-1-yl-propyl)-amine,
Example 12 2-((3-Imidazol-1-yl-propylamino)-{1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-tetrazol-5-yl}-methyl)-quinolin-8-ol,
Example 14 (3-Imidazol-1-yl-propyl)-(quinolin-2-yl-{1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-1H-tetrazol-5-yl}-methyl)-amine,
Example 19 2-[(1-Butyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol,
Example 20 2-[(1-Butyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol,
Example 25 2-[(1-Cyclopentyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol,
Example 34 2-{(3-Imidazol-1-yl-propylamino)-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-methyl}-quinolin-8-ol,
Example 49 {5-[1-(3-Imidazol-1-yl-propylamino)-cyclobutyl]-tetrazol-1-yl}-acetic methyl ester,
Example 51 {5-[(2-Hydroxy-5-methyl-phenyl)-(3-imidazol-1-yl-propylamino)-methyl]-tetrazol-1-yl}-acetic methyl ester,
Example 55 {5-[(3-Imidazol-1-yl-propylamino)-quinolin-2-yl-methyl]-tetrazol-1-yl}-acetic methyl ester,
Example 59 2-[(1-tert-Butyl-1H-tetrazol-5-yl)-(3-imidazol-1-yl-propylamino) methyl]-4-methyl-phenol,
Example 63 2-[[1-(2,2-Dimethyl-propyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-4-methyl-phenol,
Example 64 2-[[1-(2,2-Dimethyl-propyl)-1H-tetrazol-5-yl]-(3-imidazol-1-yl-propylamino)-methyl]-quinolin-8-ol,
Example 72 (1H-Benzoimidazol-5-yl)-[(1-cyclohexyl-1H-tetrazol-5-yl)-(4-methoxy-phenyl)-methyl]-amine,
Example 74 (1H-Benzoimidazol-5-yl)-[(3-propoxy-phenyl)-(1-pyridin-3-ylmethyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 75 (1H-Benzoimidazol-5-yl)-[[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-(4-methoxy-2-methyl-phenyl)-methyl]-amine,
Example 77 (1H-Benzoimidazol-5-yl)-[[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-(4-methoxy-2-methyl-phenyl)-methyl]-amine,
Example 78 {Benzo[b]thiophen-3-yl-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-(1H-benzoimidazol-5-yl)-amine,
Example 85 3-{(1H-Benzoimidazol-5-ylamino)-[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-benzoic acid methyl ester,
Example 87 {5-[(1H-Benzoimidazol-5-ylamino)-(4-bromo-phenyl)-methyl]-tetrazol-1-yl}-acetic acid tert-butyl ester,
Example 90 {Benzofuran-2-yl-[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-(1H-benzoimidazol-5-yl)-amine,
Example 102 (1H-Benzoimidazol-5-yl)-{quinolin-3-yl-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 109 (1H-Benzoimidazol-5-yl)-{(3-bromo-4-methoxy-phenyl)-[1-(tetrahydro-furan-2-ylmethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 119 {5-[Benzo[1,3]dioxol-5-yl-(1H-benzoimidazol-5-ylamino)-methyl]-tetrazol-1-yl}-acetic acid tert-butyl ester,
Example 142 (1H-Benzoimidazol-5-yl)-[(3-bromo-4-methoxy-phenyl)-(1-pyridin-3-ylmethyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 145 2-{5-[Benzo[b]thiophen-3-yl-(1H-benzoimidazol-5-ylamino)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 147 (1H-Benzoimidazol-5-yl)-[benzo[c][1,2,5]thiadiazol-5-yl-(1-benzyl-1H-tetrazol-5-yl)-methyl]-amine,
Example 148 (1H-Benzoimidazol-5-yl)-[[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-(4-chloro-3-nitro-phenyl)-methyl]-amine
Example 160 {Benzo[1,3]dioxol-5-yl-[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-(1H-benzoimidazol-5-yl)-amine,
Example 166 (1H-Benzoimidazol-5-yl)-{benzo[c][1,2,5]thiadiazol-5-yl-[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 177 (1H-Benzoimidazol-5-yl)-{(3,5-dibromo-phenyl)-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 181 (1H-Benzoimidazol-5-yl)-{benzo[c][1,2,5]thiadiazol-5-yl-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 187 2-{5-[(1H-Benzoimidazol-5-ylamino)-(3,5-dibromo-phenyl)-methyl]-tetrazol-1-yl}-N-[2-(1H-indol-3-yl)-ethyl]-acetamide,
Example 190 (1H-Benzoimidazol-5-yl)-[(1-benzyl-1H-tetrazol-5-yl)-(3,5-dibromo-phenyl)-methyl]-amine,
Example 197 (1H-Benzoimidazol-5-yl)-[[1-(4-chloro-benzyl)-1H-tetrazol-5-yl]-(4-chloro-3-nitro-phenyl)-methyl]-amine,
Example 199 2-{5-[(1H-Benzoimidazol-5-ylamino)-(4-bromo-phenyl)-methyl]-tetrazol-1-yl}-1-(3,4-dihydro-1H-isoquinolin-2-yl)-ethanone,
Example 200 2-{5-[(1H-Benzoimidazol-5-ylamino)-(4-bromo-phenyl)-methyl]-tetrazol-1-yl}-N-[2-(1H-indol-3-yl)-ethyl]-acetamide,
Example 203 (1H-Benzoimidazol-5-yl)-[[1-(2-benzyloxy-phenyl)-1H-tetrazol-5-yl]-(4-bromo-phenyl)-methyl]-amine,
Example 205 (1H-Benzoimidazol-5-yl)-{benzo[c][1,2,5]thiadiazol-5-yl-[1-(2-chloro-benzyl)-1H-tetrazol-5-yl]-methyl}-amine,
Example 208 2-{5-[(1H-Benzoimidazol-5-ylamino)-(3-propoxy-phenyl)-methyl]-tetrazol-1-yl}-cyclohexanecarboxylic acid ethyl ester,
Example 210 (1H-Benzoimidazol-5-yl)-[[1-(2-benzyloxy-phenyl)-1H-tetrazol-5-yl]-(4-methoxy-phenyl)-methyl]-amine,
Example 211 (1H-Benzoimidazol-5-yl)-{(4-pyridin-2-yl-phenyl)-[1-(2-thiophen-2-yl-ethyl)-1H-tetrazol-5-yl]-methyl}-amine, and
Example 212 {5-[(1H-Benzoimidazol-5-ylamino)-(4-pyridin-2-yl-phenyl)-methyl]-tetrazol-1-yl}-acetic acid tert-butyl ester.

42 more elements

Dependencies are inferred from the claim text.

Inhibitors of glutaminyl cyclase

Life of this patent

Inhibitors of glutaminyl cyclase

Life of this patent

Abstract

Claims23