Patent EA-002270-B1 (EA)
Title: 6-phenylpyridyl-2-amine derivatives
Inventor: LOWE JOHN ADAMS III
IPC: C07D401/12
Filed: 1997-02-17
Abstract: 1. A compound of the formula   and the pharmaceutically acceptable salts thereof, wherein R<1> and R<2> form, together with the nitrogen to which they are attached an azabicyclic ring containing from 6 to 14 ring members, from 1 to 3 of which are nitrogen and the rest of which are carbon; n is 0, 1 or 2; and each carbon of said (CH2)n can be substituted with R<8>; m is 0, 1 or 2; and each carbon of said (CH2)m can be substituted with R<9>; each R<8> and R<9> are selected, independently, from (C1-C4) alkyl, aryl(C1-C4) alkyl, said aryl is selected from phenyl or naphthyl; allyl and phenallyl; X and Y are selected, independently, from methyl, methoxy-, hydroxy- and hydrogen; and R<10> is hydrogen or (C1-C6) alkyl; with proviso that R<8> is absent when n is 0, and R<9> is absent when m is 0, and the pharmaceutically acceptable salt thereof. 2. A compound of Claim 1, wherein R<1> and R<2> form, together with the nitrogen to which they are attached an azabicyclic ring, selected from   and   wherein R<3> and R<4> selected from the group, comprising hydrogen, (C1-C6)alkyl, phenyl, naphthyl, (C1-C6)alkyl-C(=O), HC(=O), (C1-C6)alkoxy-(C=O)-, phenyl-C(=O)-, naphthyl-C(=O)- and (R<7>)2NC(=O)-, wherein each R<7> independently is selected from hydrogen and (C1-C6)alkyl; and R<5> is selected from hydrogen, (C1-C6)alkyl, phenyl, naphthyl, phenyl-(C1-C6)alkyl- and naphthyl(C1-C6)alkyl-. 3. A compound according to Claim 1 wherein NRR is 6-{4-[2-(4-phenetylpiperazine-1-yl)-ethyl]-phenyl}pyridin-2-ylamine; 6-((2-(6-(tert-butoxycarbonylamino)-3-azabicyclo[3.1.0]hex-3-yl)-ethyl)-phenyl)-pyridin-2-ylamine; 3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.1.0]hex-6-ylamine; phenylamide 4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-carboxylic acid; 1-(4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-2-phenylethanone; 1-(4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-2-(4-fluorophenyl)-ethanon; 6-{4-[2-(3,4-dihydro-1H-isoquinoline-2-yl)-ethyl]-phenyl}-pyridin-2-ylamine; (4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-furan-2-yl-methanone; 6-{4-[(2-(4-m-tolyl)-piperazine-1-yl)-ethyl]-phenyl}-pyridin-2-ylamine; 6-(4-{2-[4-(3-trifluoromethylphenyl)-piperazine-1-yl]-ethyl}-phenyl)-pyridin-2-ylamine; 1-(4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-ethanon; 1-(4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-2-methoxyethanon; 1-(4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-2-phenoxyethanon; (4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-cyclopentylmethanone; 6-{4-[2-(5-methyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-ethyl]-phenyl}-pyridin-2-ylamine; 6-(4-{2-[4-(4-phenylthiazole-2-yl)-piperazine-1-yl]-ethyl}-phenyl)-pyridin-2-ylamine; 2-(4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-1-phenylethanon; 6-{4-[2-(4-isobutylpiperazine-1-yl)-ethyl]-phenyl}-pyridin-2-ylamine; 6-{4-[2-(1,2,3,4-tetrahydronaphthalene-2-ylamino)-ethyl]-phenyl}-pyridin-2-ylamine; 6-{[(dibenzylamino)-ethyl]-phenyl}-pyridin-2-ylamine; 6-{4-[2-(8-azaspiro[4.5]dec-8-yl)-ethyl]-phenyl}-pyridin-2-ylamine; 6-{4-[2-(4-dimethylaminopiperidine-1-yl)-ethyl]-phenyl}-pyridin-2-ylamine; 6-{4-[2-(1,3-dihydroisoindole-2-yl)-ethyl]-phenyl}-pyridin-2-ylamine; 2-(4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-N-isopropylacetamide; ethyl ether (4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-acetic acid; (4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-phenylmethanone; 6-{4-[2-(3-phenylpyrrolidine-1-yl)-ethyl]-phenyl}-pyridin-2-ylamine; 6-(4-{2-[4-(1-phenyl-1H-tetrazole-5-yl)-piperazine-1-yl]-ethyl}-phenyl)-pyridin-2-ylamine; 2-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; (4-chlorophenyl)-amide 4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-carboxylic acid; para-tolylamide 4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-carboxylic acid; (4-methoxyphenyl)-amide 4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-carboxylic acid; cyclohexylamide 4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-carboxylic acid; phenyl ether  4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-carboxylic acid; 6-(4-{2-[4-(1-phenyl-1H-imidazole-2-yl)-piperazine-1-yl]-ethyl}-phenyl)-pyridin-2-ylamine; 6-[4-(2-phenetylaminoethyl)-phenyl]-pyridin-2-ylamine; 1-(3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.1.0]hex-6-yl)-3-phenylurea; (3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.1.0]hex-6-yl)-dimethylamine; N-(3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.1.0]hex-6-yl)-2-(4-fluorophenyl)-acetamide; 6-(4-{2-[4-(3-phenylallyl)-piperazine-1-yl]-ethyl}-phenyl)-pyridin-2-ylamine; 6-(4-{2-[4-(3-phenylpropyl)-piperazine-1-yl]-ethyl}-phenyl)-pyridin-2-ylamine; (3,4-dimethylphenyl)-amide 4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-carboxylic acid; 1-(4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-2-(4-chlorophenyl)-ethanon; 8-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-benzyl-1,3,8-triazaspiro[4.5]decan-2,4-dione; 3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.2.1]oct-8-ylamine; m-tolylamide 4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-carboxylic acid; (3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.1.0]hex-6-yl)-phenetylamine; benzylamide 4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-carboxylic acid; 6-[4-(2-{4-[1-(4-fluorophenyl)-1H-tetrazole-5-yl]-piperazine-1-yl}-ethyl)-phenyl]-pyridin-2-ylamine; 6-(4-{2-[4-cis-(4-phenylcyclohexyl)-piperazine-1-yl]-ethyl}-phenyl)-pyridin-2-ylamine; 6-(4-{2-[4-trans-(4-phenylcyclohexyl)-piperazine-1-yl]-ethyl}-phenyl)-pyridin-2-ylamine; hydrochloride (3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.1.0]hex-6-yl)-(3-phenylpropyl)-amine; 2-(3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.1.0]hex-6-ylamino)-acetamide; 6-[4-(2-{4-[2-(4-fluorophenyl)-ethyl]-piperazine-1-yl}-ethyl)-phenyl]-pyridin-2-ylamine; 6-(4-{2-[4-(1-methyl-2-phenylethyl)-piperazine-1-yl]-ethyl}-phenyl)-pyridin-2-ylamine; 6-(4-{2-[4-(1,2,3,4-tetrahydronaphthalene-2-yl)-piperazine-1-yl]-ethyl}-phenyl)-pyridin-2-ylamine; N-(1-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-pyrrolidine-3-yl)-2-(4-fluorophenyl)-acetamide; 8-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-phenetyl-1,3,8-triazaspiro[4.5]decan-2,4-dione; 8-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-8-azabicyclo[3.2.1]oct-3-ylamine; benzylamide 4-amino-1-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperidine-4-carboxylic acid; 6-(4-{2-[4-(2-aminoethyl)-piperazine-1-yl]-ethyl}-phenyl)-pyridin-2-ylamine; 2-amino-1-(4-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperazine-1-yl)-3-phenylpropane-1-one; {2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-amine; 1-(1-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperidine-4-yl)-3-phenylurea; 1-(1-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperidine-4-yl)-3-benzylurea; N-(1-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperidine-4-yl)-2-(4-fluorophenyl)-acetamide; {2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-(8-azabicyclo[3.2.1]oct-3-yl)amine; 6-{4-[2-(4-aminopiperidine-1-yl)-ethyl]-phenyl}-pyridin-2-ylamine; morpholineamide 4-amino-1-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperidine-4-carboxylic acid; pyrrolidineamide 4-amino-1-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperidine-4-carboxylic acid; 6-{4-[2-(3-aminopyrrolidine-1-yl)-ethyl]-phenyl}-pyridin-2-ylamine; 1-(3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethylamino}-8-azabicyclo[3.2.1]oct-8-yl)-2-(4-fluorophenyl)-ethanon; 1-(1-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-pyrrolidine-3-yl)-3-phenylurea; 1-(1-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-pyrrolidine-3-yl)-3-benzylurea; 1-(1-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-pyrrolidine-3-yl)-3-cyclohexylurea; {2-[4-(6-aminopyridin-2yl)-phenyl]-ethyl}-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-amine; {2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-(3-benzyl-3-azabicyclo[3.1.0]hex-6-yl)-amine; {2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-[8-(4-fluorobenzyl)-8-azabicyclo[3.2.1]oct-3-yl]-amine; {2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-[8-(4-chlorobenzyl)-8-azabicyclo[3.2.1]oct-3-yl]-amine; phenetylamide 4-amino-1-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-piperidine-4-carboxylic acid; phenylamide 3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethylamino}-pyrrolidine-1-carboxylic acid; (3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethylamino}-pyrrolidine-1-yl)-phenylmethanone; 6-{4-[2-(1-benzylpyrrolidine-3-ylamino)-ethyl]-phenyl}-pyridin-2-ylamine; N-(8-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-benzamide; {2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-[3-benzyl-3-azabicyclo[3.3.1]none-9-yl]-amine; N-(8-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-(4-fluorophenyl)-acetamide; 6-{4-[2-(3-aminopiperidine-1-yl)-ethyl]-phenyl}-pyridin-2-ylamine; N-(3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.3.1]none-9-yl)-benzamide (anti-isomer); N-(3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.3.1]none-9-yl)-benzamide (sin-isomer); 6-{4-[2-(4-benzhydrylpiperazine-1-yl)-ethyl]-phenyl}-pyridin-2-ylamine; 6-{4-[2-(4-benzhydrylpiperidine-1-yl)-ethyl]-phenyl}-pyridin-2-ylamine; 3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.3.1]none-9-ylamine; ethyl ether  3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.1.0]hexane-6-carboxylic acid; 3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.1.0]hexane-6-carboxylic acid; tert-butyl ether  3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethylamino}-piperidine-1-carboxylic acid; 6-{4-[2-(piperidine-3-ylamino)-ethyl]-phenyl}-pyridin-2-ylamine; 6-{4-[2-(1-benzylpiperidine-4-ylamino)-ethyl]-phenyl}-pyridin-2-ylamine; 3-{2-[4-(6-aminopyridin-2-yl)-phenyl]-ethyl}-3-azabicyclo[3.1.0]hex-6-ylamine (anti-isomer); 6-{4-[2-(piperidine-4-ylamino)-ethyl]-phenyl}-pyridin-2-ylamine; 6-(4-{2-[(piperidine-4-yl