RU2457207C2 - Активаторы глюкокиназы - Google Patents
Активаторы глюкокиназы Download PDFInfo
- Publication number
- RU2457207C2 RU2457207C2 RU2008141999/04A RU2008141999A RU2457207C2 RU 2457207 C2 RU2457207 C2 RU 2457207C2 RU 2008141999/04 A RU2008141999/04 A RU 2008141999/04A RU 2008141999 A RU2008141999 A RU 2008141999A RU 2457207 C2 RU2457207 C2 RU 2457207C2
- Authority
- RU
- Russia
- Prior art keywords
- pyridin
- ylamino
- ylthio
- amine
- thiazol
- Prior art date
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- 102000030595 Glucokinase Human genes 0.000 title abstract 2
- 108010021582 Glucokinase Proteins 0.000 title abstract 2
- 239000012190 activator Substances 0.000 title 1
- 125000005842 heteroatom Chemical group 0.000 claims abstract 81
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 57
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 50
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 40
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 39
- 125000000217 alkyl group Chemical group 0.000 claims abstract 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 27
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 27
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 21
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 19
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- -1 SR a Inorganic materials 0.000 claims 51
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 23
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 125000004429 atom Chemical group 0.000 claims 9
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 3
- 229940124828 glucokinase activator Drugs 0.000 claims 3
- PLICAMJYVAUBDX-UHFFFAOYSA-N methyl 3-[5-(2-chlorophenyl)sulfanyl-6-[(4-methyl-1,3-thiazol-2-yl)amino]pyridin-3-yl]sulfanylpropanoate Chemical compound C=1C=CC=C(Cl)C=1SC1=CC(SCCC(=O)OC)=CN=C1NC1=NC(C)=CS1 PLICAMJYVAUBDX-UHFFFAOYSA-N 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- WKNWYSOGDABRNQ-UHFFFAOYSA-N 1-[3-[5-bromo-2-[(4-methyl-1,3-thiazol-2-yl)amino]pyridin-3-yl]oxypyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1N(C(=O)CN(C)C)CCC1OC1=CC(Br)=CN=C1NC1=NC(C)=CS1 WKNWYSOGDABRNQ-UHFFFAOYSA-N 0.000 claims 2
- NNDXKMQWHMOMSS-UHFFFAOYSA-N 1-[3-[5-bromo-2-[(4-methyl-1,3-thiazol-2-yl)amino]pyridin-3-yl]oxypyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC1OC1=CC(Br)=CN=C1NC1=NC(C)=CS1 NNDXKMQWHMOMSS-UHFFFAOYSA-N 0.000 claims 2
- ZITLABCYWTZBIZ-UHFFFAOYSA-N 1-[4-[5-[[3-(4-fluorophenoxy)-5-[(3-methyl-[1,2]oxazolo[5,4-b]pyridin-4-yl)sulfanyl]pyridin-2-yl]amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NSC(NC=2C(=CC(SC=3C=4C(C)=NOC=4N=CC=3)=CN=2)OC=2C=CC(F)=CC=2)=N1 ZITLABCYWTZBIZ-UHFFFAOYSA-N 0.000 claims 2
- WTEUDCWQXUJIDU-UHFFFAOYSA-N 1-[4-[[5-[[3-(4-fluorophenoxy)-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl]amino]-1,2,4-thiadiazol-3-yl]methyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1CC1=NSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC(F)=CC=2)=N1 WTEUDCWQXUJIDU-UHFFFAOYSA-N 0.000 claims 2
- CERJITPTQCALBF-UHFFFAOYSA-N 2-[3-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanylphenoxy]acetic acid Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=C(OCC(O)=O)C=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 CERJITPTQCALBF-UHFFFAOYSA-N 0.000 claims 2
- IRQKJDXIOXGKIR-UHFFFAOYSA-N 2-methyl-1-[4-[5-[(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)C(C)C)CCC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 IRQKJDXIOXGKIR-UHFFFAOYSA-N 0.000 claims 2
- SZZWZYCAXOGNDI-UHFFFAOYSA-N 3-[5-bromo-2-[(4-methyl-1,3-thiazol-2-yl)amino]pyridin-3-yl]oxy-n-propan-2-ylpyrrolidine-1-carboxamide Chemical compound C1N(C(=O)NC(C)C)CCC1OC1=CC(Br)=CN=C1NC1=NC(C)=CS1 SZZWZYCAXOGNDI-UHFFFAOYSA-N 0.000 claims 2
- MDGRWNJTIVZHRR-UHFFFAOYSA-N 3-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanylphenol Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=C(O)C=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 MDGRWNJTIVZHRR-UHFFFAOYSA-N 0.000 claims 2
- BQSMHKFOKZYEIC-UHFFFAOYSA-N 4-methyl-n-[3-phenoxy-5-(1-pyridin-2-ylethylsulfanyl)pyridin-2-yl]-1,3-thiazol-2-amine Chemical compound C=1C=CC=NC=1C(C)SC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 BQSMHKFOKZYEIC-UHFFFAOYSA-N 0.000 claims 2
- KLEIAUFIJRPUFE-UHFFFAOYSA-N 4-methyl-n-[3-phenoxy-5-[3-(2-piperidin-1-ylethoxy)phenyl]sulfanylpyridin-2-yl]-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=C(OCCN4CCCCC4)C=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 KLEIAUFIJRPUFE-UHFFFAOYSA-N 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- KRBIYNHNCBOATB-UHFFFAOYSA-N n-(5-bromo-3-phenylsulfanylpyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(Br)=CN=2)SC=2C=CC=CC=2)=N1 KRBIYNHNCBOATB-UHFFFAOYSA-N 0.000 claims 2
- SRALDIYQFMYERT-UHFFFAOYSA-N n-[3-(2-chlorophenyl)sulfanyl-5-(1-pyridin-2-ylethylsulfanyl)pyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=NC=1C(C)SC(C=C1SC=2C(=CC=CC=2)Cl)=CN=C1NC1=NC(C)=CS1 SRALDIYQFMYERT-UHFFFAOYSA-N 0.000 claims 2
- HONDWGLPBPMPFR-UHFFFAOYSA-N n-[3-(2-chlorophenyl)sulfanyl-5-(piperidin-4-ylmethylsulfanyl)pyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SCC3CCNCC3)=CN=2)SC=2C(=CC=CC=2)Cl)=N1 HONDWGLPBPMPFR-UHFFFAOYSA-N 0.000 claims 2
- BNRZADXGNWSBSI-UHFFFAOYSA-N n-[3-(2-chlorophenyl)sulfanyl-5-phenylsulfanylpyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=CC=CC=3)=CN=2)SC=2C(=CC=CC=2)Cl)=N1 BNRZADXGNWSBSI-UHFFFAOYSA-N 0.000 claims 2
- SXRUFHRIEXDEBJ-UHFFFAOYSA-N n-[5-(2-chlorophenyl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C(=CC=CC=3)Cl)=CN=2)OC=2C=CC=CC=2)=N1 SXRUFHRIEXDEBJ-UHFFFAOYSA-N 0.000 claims 2
- RMCTYZNLXXVFSR-UHFFFAOYSA-N n-[5-(2-methoxyphenyl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound COC1=CC=CC=C1SC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 RMCTYZNLXXVFSR-UHFFFAOYSA-N 0.000 claims 2
- QNDGXFOQZILMJP-UHFFFAOYSA-N n-[5-(3-chlorophenyl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=C(Cl)C=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 QNDGXFOQZILMJP-UHFFFAOYSA-N 0.000 claims 2
- WNMVUOWSVIZOIJ-UHFFFAOYSA-N n-[5-(3-methoxyphenyl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound COC1=CC=CC(SC=2C=C(OC=3C=CC=CC=3)C(NC=3SC=C(C)N=3)=NC=2)=C1 WNMVUOWSVIZOIJ-UHFFFAOYSA-N 0.000 claims 2
- SCKJYSMGYVZACR-UHFFFAOYSA-N n-[5-[3-[3-(dimethylamino)propoxy]phenyl]sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CN(C)CCCOC1=CC=CC(SC=2C=C(OC=3C=CC=CC=3)C(NC=3SC=C(C)N=3)=NC=2)=C1 SCKJYSMGYVZACR-UHFFFAOYSA-N 0.000 claims 2
- MOXLUWMOEDVNJB-UHFFFAOYSA-N n-[5-bromo-3-(2-chlorophenyl)sulfanylpyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(Br)=CN=2)SC=2C(=CC=CC=2)Cl)=N1 MOXLUWMOEDVNJB-UHFFFAOYSA-N 0.000 claims 2
- RQMQZJSNGGKYLJ-UHFFFAOYSA-N n-[5-bromo-3-[1-(1-methylimidazol-4-yl)sulfonylpyrrolidin-3-yl]oxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(Br)=CN=2)OC2CN(CC2)S(=O)(=O)C=2N=CN(C)C=2)=N1 RQMQZJSNGGKYLJ-UHFFFAOYSA-N 0.000 claims 2
- OGTIVLDRXVBTPJ-QGZVFWFLSA-N (2r)-2-hydroxy-1-[4-[5-[(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@H](O)C)CCC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 OGTIVLDRXVBTPJ-QGZVFWFLSA-N 0.000 claims 1
- QQIGNQVYOAYHEG-UHFFFAOYSA-N 1-(2,3-dihydroindol-1-yl)-2-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanyl-2-piperidin-4-ylethanone Chemical compound CC1=CSC(NC=2C(=CC(SC(C3CCNCC3)C(=O)N3C4=CC=CC=C4CC3)=CN=2)OC=2C=CC=CC=2)=N1 QQIGNQVYOAYHEG-UHFFFAOYSA-N 0.000 claims 1
- DYWLNUCDOIFMCT-UHFFFAOYSA-N 1-(2-methylpiperidin-1-yl)-2-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanyl-2-piperidin-4-ylethanone Chemical compound CC1CCCCN1C(=O)C(C1CCNCC1)SC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 DYWLNUCDOIFMCT-UHFFFAOYSA-N 0.000 claims 1
- SGVXXMJXJDZWMT-UHFFFAOYSA-N 1-(4-methylpiperazin-1-yl)-2-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanylethanone Chemical compound C1CN(C)CCN1C(=O)CSC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 SGVXXMJXJDZWMT-UHFFFAOYSA-N 0.000 claims 1
- WRMYRIOGQZHPSD-UHFFFAOYSA-N 1-(7-azabicyclo[2.2.1]heptan-7-yl)-2-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanyl-2-piperidin-4-ylethanone Chemical compound CC1=CSC(NC=2C(=CC(SC(C3CCNCC3)C(=O)N3C4CCC3CC4)=CN=2)OC=2C=CC=CC=2)=N1 WRMYRIOGQZHPSD-UHFFFAOYSA-N 0.000 claims 1
- KZIHFEGOYNJBPY-UHFFFAOYSA-N 1-[3-[2-[(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 KZIHFEGOYNJBPY-UHFFFAOYSA-N 0.000 claims 1
- JXCQJTPNCGBXOH-UHFFFAOYSA-N 1-[3-[2-[(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 JXCQJTPNCGBXOH-UHFFFAOYSA-N 0.000 claims 1
- LKDOUELDMZRMAQ-UHFFFAOYSA-N 1-[3-[5-(3-methoxyphenyl)sulfanyl-6-[[3-(oxolan-2-yl)-1,2,4-thiadiazol-5-yl]amino]pyridin-3-yl]oxyphenyl]ethanol Chemical compound COC1=CC=CC(SC=2C(=NC=C(OC=3C=C(C=CC=3)C(C)O)C=2)NC=2SN=C(N=2)C2OCCC2)=C1 LKDOUELDMZRMAQ-UHFFFAOYSA-N 0.000 claims 1
- ZUAVUBATAYDJJY-UHFFFAOYSA-N 1-[3-[5-[(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC1C1=NSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 ZUAVUBATAYDJJY-UHFFFAOYSA-N 0.000 claims 1
- FIUKPKGYTHMYFU-UHFFFAOYSA-N 1-[3-methyl-4-[2-[(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound CC1CN(C(C)=O)CCC1C1=CSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 FIUKPKGYTHMYFU-UHFFFAOYSA-N 0.000 claims 1
- KQRRGIPKLQGZRO-UHFFFAOYSA-N 1-[4-[2-[(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 KQRRGIPKLQGZRO-UHFFFAOYSA-N 0.000 claims 1
- YQQVEDASJHEJJW-UHFFFAOYSA-N 1-[4-[2-[(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 YQQVEDASJHEJJW-UHFFFAOYSA-N 0.000 claims 1
- NMDNPJJFDVRSKU-UHFFFAOYSA-N 1-[4-[2-[(3-phenylsulfanyl-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)SC=2C=CC=CC=2)=N1 NMDNPJJFDVRSKU-UHFFFAOYSA-N 0.000 claims 1
- LWQCYPKRPNXVFL-UHFFFAOYSA-N 1-[4-[2-[(3-phenylsulfanyl-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)SC=2C=CC=CC=2)=N1 LWQCYPKRPNXVFL-UHFFFAOYSA-N 0.000 claims 1
- BVNZSAFBZRYALM-UHFFFAOYSA-N 1-[4-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 BVNZSAFBZRYALM-UHFFFAOYSA-N 0.000 claims 1
- BPPGCCUCIGHIBN-UHFFFAOYSA-N 1-[4-[2-[(5-bromo-3-phenylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(Br)=CN=2)SC=2C=CC=CC=2)=N1 BPPGCCUCIGHIBN-UHFFFAOYSA-N 0.000 claims 1
- OZKUHRXYXGGLQA-UHFFFAOYSA-N 1-[4-[2-[[3-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenyl)sulfanylpyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound COC1=CC=CC(SC=2C=C(OC=3C(=CC(F)=CC=3)Br)C(NC=3SC=C(N=3)C3CCN(CC3)C(=O)CN(C)C)=NC=2)=C1 OZKUHRXYXGGLQA-UHFFFAOYSA-N 0.000 claims 1
- BUMUBDIVFWTKDB-UHFFFAOYSA-N 1-[4-[2-[[3-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenyl)sulfanylpyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound COC1=CC=CC(SC=2C=C(OC=3C(=CC(F)=CC=3)Br)C(NC=3SC=C(N=3)C3CCN(CC3)C(C)=O)=NC=2)=C1 BUMUBDIVFWTKDB-UHFFFAOYSA-N 0.000 claims 1
- HWYRZGGTQHTFIN-UHFFFAOYSA-N 1-[4-[2-[[3-(4-fluoro-2-methylphenoxy)-5-(3-methoxyphenyl)sulfanylpyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound COC1=CC=CC(SC=2C=C(OC=3C(=CC(F)=CC=3)C)C(NC=3SC=C(N=3)C3CCN(CC3)C(C)=O)=NC=2)=C1 HWYRZGGTQHTFIN-UHFFFAOYSA-N 0.000 claims 1
- HHKVYBLADRLVOQ-UHFFFAOYSA-N 1-[4-[2-[[3-(4-fluorophenoxy)-5-(3-methoxyphenyl)sulfanylpyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound COC1=CC=CC(SC=2C=C(OC=3C=CC(F)=CC=3)C(NC=3SC=C(N=3)C3CCN(CC3)C(C)=O)=NC=2)=C1 HHKVYBLADRLVOQ-UHFFFAOYSA-N 0.000 claims 1
- GKQKKRBAUYTGFY-UHFFFAOYSA-N 1-[4-[2-[[3-(4-fluorophenoxy)-5-[(3-methyl-[1,2]oxazolo[5,4-b]pyridin-4-yl)sulfanyl]pyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4C(C)=NOC=4N=CC=3)=CN=2)OC=2C=CC(F)=CC=2)=N1 GKQKKRBAUYTGFY-UHFFFAOYSA-N 0.000 claims 1
- OAWITPKBONGDHU-UHFFFAOYSA-N 1-[4-[2-[[3-phenoxy-5-[6-(trifluoromethyl)pyridin-3-yl]sulfanylpyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=NC(=CC=3)C(F)(F)F)=CN=2)OC=2C=CC=CC=2)=N1 OAWITPKBONGDHU-UHFFFAOYSA-N 0.000 claims 1
- ZTAMGNLYXNZLHO-UHFFFAOYSA-N 1-[4-[2-[[5-(2-chloropyridin-4-yl)sulfanyl-3-phenoxypyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=C(Cl)N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 ZTAMGNLYXNZLHO-UHFFFAOYSA-N 0.000 claims 1
- ZQYAZIOBMABSNA-UHFFFAOYSA-N 1-[4-[2-[[5-(2-methylthieno[3,2-b]pyridin-7-yl)sulfanyl-3-phenoxypyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC(C)=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 ZQYAZIOBMABSNA-UHFFFAOYSA-N 0.000 claims 1
- NWDPDLLWULXSQL-UHFFFAOYSA-N 1-[4-[2-[[5-(3-methylthieno[3,2-b]pyridin-7-yl)sulfanyl-3-phenoxypyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=C(C)C=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 NWDPDLLWULXSQL-UHFFFAOYSA-N 0.000 claims 1
- RORDDYSVEXVHQH-UHFFFAOYSA-N 1-[4-[2-[[5-(4-methoxypyrimidin-2-yl)sulfanyl-3-phenoxypyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound COC1=CC=NC(SC=2C=C(OC=3C=CC=CC=3)C(NC=3SC=C(N=3)C3CCN(CC3)C(C)=O)=NC=2)=N1 RORDDYSVEXVHQH-UHFFFAOYSA-N 0.000 claims 1
- OVMNXWXKRPPZNK-UHFFFAOYSA-N 1-[4-[2-[[5-(5-chlorothieno[3,2-b]pyridin-7-yl)sulfanyl-3-phenoxypyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=C(Cl)C=3)=CN=2)OC=2C=CC=CC=2)=N1 OVMNXWXKRPPZNK-UHFFFAOYSA-N 0.000 claims 1
- JYPUKVBNKCTVKS-UHFFFAOYSA-N 1-[4-[2-[[5-(6-bromothieno[3,2-b]pyridin-7-yl)sulfanyl-3-phenoxypyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3Br)=CN=2)OC=2C=CC=CC=2)=N1 JYPUKVBNKCTVKS-UHFFFAOYSA-N 0.000 claims 1
- VXFSEELNTKPJQM-UHFFFAOYSA-N 1-[4-[2-[[5-thieno[3,2-b]pyridin-7-ylsulfanyl-3-[2-(trifluoromethyl)phenoxy]pyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C(=CC=CC=2)C(F)(F)F)=N1 VXFSEELNTKPJQM-UHFFFAOYSA-N 0.000 claims 1
- WXGANWHVIGYVJO-UHFFFAOYSA-N 1-[4-[2-[[5-thieno[3,2-b]pyridin-7-ylsulfanyl-3-[4-(trifluoromethyl)phenoxy]pyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC(=CC=2)C(F)(F)F)=N1 WXGANWHVIGYVJO-UHFFFAOYSA-N 0.000 claims 1
- MGSFDMFRYXZHBE-UHFFFAOYSA-N 1-[4-[5-[(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 MGSFDMFRYXZHBE-UHFFFAOYSA-N 0.000 claims 1
- NNKWRFBKGRIZPF-UHFFFAOYSA-N 1-[4-[5-[(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 NNKWRFBKGRIZPF-UHFFFAOYSA-N 0.000 claims 1
- SCBLXMRXAPIJIM-UHFFFAOYSA-N 1-[4-[5-[(3-phenylsulfanyl-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)SC=2C=CC=CC=2)=N1 SCBLXMRXAPIJIM-UHFFFAOYSA-N 0.000 claims 1
- KJKJHXMWKUNILS-UHFFFAOYSA-N 1-[4-[5-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 KJKJHXMWKUNILS-UHFFFAOYSA-N 0.000 claims 1
- IZGGKWKWYSUYPA-UHFFFAOYSA-N 1-[4-[5-[[3-(4-fluorophenoxy)-5-(5-methylpyrazolo[1,5-a]pyrimidin-7-yl)sulfanylpyridin-2-yl]amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NSC(NC=2C(=CC(SC=3N4N=CC=C4N=C(C)C=3)=CN=2)OC=2C=CC(F)=CC=2)=N1 IZGGKWKWYSUYPA-UHFFFAOYSA-N 0.000 claims 1
- XCQHLQVENJZBNF-UHFFFAOYSA-N 1-[4-[5-[[3-(4-fluorophenoxy)-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl]amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC(F)=CC=2)=N1 XCQHLQVENJZBNF-UHFFFAOYSA-N 0.000 claims 1
- VFVPHSZQLLBTNV-UHFFFAOYSA-N 1-[4-[5-[[5-thieno[3,2-b]pyridin-7-ylsulfanyl-3-[2-(trifluoromethyl)phenoxy]pyridin-2-yl]amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C(=CC=CC=2)C(F)(F)F)=N1 VFVPHSZQLLBTNV-UHFFFAOYSA-N 0.000 claims 1
- IBQKMYLGWYJZPK-UHFFFAOYSA-N 1-[4-[[2-[(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]methyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1CC1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 IBQKMYLGWYJZPK-UHFFFAOYSA-N 0.000 claims 1
- BXXNUGPMKVKLKD-UHFFFAOYSA-N 1-[[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]methyl]pyrrolidin-2-one Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CN=C1NC(SC=1)=NC=1CN1CCCC1=O BXXNUGPMKVKLKD-UHFFFAOYSA-N 0.000 claims 1
- XEBIGXYVBMNKFF-UHFFFAOYSA-N 1-[[2-[[5-bromo-3-(4-fluorophenoxy)pyridin-2-yl]amino]-1,3-thiazol-4-yl]methyl]piperazin-2-one Chemical compound C1=CC(F)=CC=C1OC1=CC(Br)=CN=C1NC1=NC(CN2C(CNCC2)=O)=CS1 XEBIGXYVBMNKFF-UHFFFAOYSA-N 0.000 claims 1
- VTIDVWAOBBGJLK-UHFFFAOYSA-N 1-[[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanylmethyl]pyrrolidin-2-one Chemical compound CC1=CSC(NC=2C(=CC(SCN3C(CCC3)=O)=CN=2)OC=2C=CC=CC=2)=N1 VTIDVWAOBBGJLK-UHFFFAOYSA-N 0.000 claims 1
- HJPDLPVKWLCRKG-UHFFFAOYSA-N 2,2-dimethyl-3-[2-[(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]propanoic acid Chemical compound OC(=O)C(C)(C)CC1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 HJPDLPVKWLCRKG-UHFFFAOYSA-N 0.000 claims 1
- XPHQKKKLVGAZLI-UHFFFAOYSA-N 2-(1-methylpiperidin-4-yl)-2-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanylethanol Chemical compound C1CN(C)CCC1C(CO)SC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 XPHQKKKLVGAZLI-UHFFFAOYSA-N 0.000 claims 1
- RHFSJRFLYYWEOJ-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-[(3-phenylsulfanyl-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)SC=2C=CC=CC=2)=N1 RHFSJRFLYYWEOJ-UHFFFAOYSA-N 0.000 claims 1
- YOFOTNJPBLKKRW-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-[[3-(4-fluorophenoxy)-5-[(3-methyl-[1,2]oxazolo[5,4-b]pyridin-4-yl)sulfanyl]pyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4C(C)=NOC=4N=CC=3)=CN=2)OC=2C=CC(F)=CC=2)=N1 YOFOTNJPBLKKRW-UHFFFAOYSA-N 0.000 claims 1
- IRMFOFIIMCDJCM-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[5-[(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(C)C)CCC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 IRMFOFIIMCDJCM-UHFFFAOYSA-N 0.000 claims 1
- DIGCEHXBGHBKOW-UHFFFAOYSA-N 2-[2-([1,3]thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-yl]sulfanylbenzonitrile Chemical compound N#CC1=CC=CC=C1SC1=CC=CN=C1NC1=NC2=CC=CN=C2S1 DIGCEHXBGHBKOW-UHFFFAOYSA-N 0.000 claims 1
- USFOMTRZOKGEJV-UHFFFAOYSA-N 2-[2-[(3-methyl-1,2,4-thiadiazol-5-yl)amino]pyridin-3-yl]oxybenzonitrile Chemical compound CC1=NSC(NC=2C(=CC=CN=2)OC=2C(=CC=CC=2)C#N)=N1 USFOMTRZOKGEJV-UHFFFAOYSA-N 0.000 claims 1
- KPJJEXKLZAXHEE-UHFFFAOYSA-N 2-[2-[(4-methyl-1,3-thiazol-2-yl)amino]pyridin-3-yl]oxybenzonitrile Chemical compound CC1=CSC(NC=2C(=CC=CN=2)OC=2C(=CC=CC=2)C#N)=N1 KPJJEXKLZAXHEE-UHFFFAOYSA-N 0.000 claims 1
- VKUUQMWMYSVVCM-UHFFFAOYSA-N 2-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]-1-pyrrolidin-1-ylethanone Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CN=C1NC(SC=1)=NC=1CC(=O)N1CCCC1 VKUUQMWMYSVVCM-UHFFFAOYSA-N 0.000 claims 1
- OLWADNZJAOLANB-UHFFFAOYSA-N 2-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 OLWADNZJAOLANB-UHFFFAOYSA-N 0.000 claims 1
- OQCILTWYKYSECY-UHFFFAOYSA-N 2-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 OQCILTWYKYSECY-UHFFFAOYSA-N 0.000 claims 1
- RIEUCFMKILUJIK-UHFFFAOYSA-N 2-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]-n-methylacetamide Chemical compound CNC(=O)CC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 RIEUCFMKILUJIK-UHFFFAOYSA-N 0.000 claims 1
- YFOWDOMSGRLAEY-UHFFFAOYSA-N 2-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 YFOWDOMSGRLAEY-UHFFFAOYSA-N 0.000 claims 1
- ZIBCEKSZIMSYLA-UHFFFAOYSA-N 2-[4-[5-[(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanol Chemical compound C1CN(CCO)CCC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 ZIBCEKSZIMSYLA-UHFFFAOYSA-N 0.000 claims 1
- JTSDLWCTUGSYPK-UHFFFAOYSA-N 2-[4-[[5-phenoxy-6-[[4-(2-phenylethyl)-1,3-thiazol-2-yl]amino]pyridin-3-yl]sulfanyl-pyridin-2-ylmethyl]piperidin-1-yl]ethanol Chemical compound C1CN(CCO)CCC1C(C=1N=CC=CC=1)SC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(CCC=2C=CC=CC=2)=CS1 JTSDLWCTUGSYPK-UHFFFAOYSA-N 0.000 claims 1
- PHWFJGUMHDILHU-UHFFFAOYSA-N 2-[4-[[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanyl-pyridin-2-ylmethyl]piperidin-1-yl]ethanol Chemical compound CC1=CSC(NC=2C(=CC(SC(C3CCN(CCO)CC3)C=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 PHWFJGUMHDILHU-UHFFFAOYSA-N 0.000 claims 1
- LPOXLRTWNDANSS-UHFFFAOYSA-N 2-[4-methyl-5-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanyl-1,2,4-triazol-3-yl]acetonitrile Chemical compound CC1=CSC(NC=2C(=CC(SC=3N(C(CC#N)=NN=3)C)=CN=2)OC=2C=CC=CC=2)=N1 LPOXLRTWNDANSS-UHFFFAOYSA-N 0.000 claims 1
- ZBVZTULNGBDOHL-UHFFFAOYSA-N 2-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanyl-1-pyrrolidin-1-ylethanone Chemical compound CC1=CSC(NC=2C(=CC(SCC(=O)N3CCCC3)=CN=2)OC=2C=CC=CC=2)=N1 ZBVZTULNGBDOHL-UHFFFAOYSA-N 0.000 claims 1
- YFZOSVCOAMMSOO-UHFFFAOYSA-N 2-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanyl-2-piperidin-4-yl-1-pyrrolidin-1-ylethanone Chemical compound CC1=CSC(NC=2C(=CC(SC(C3CCNCC3)C(=O)N3CCCC3)=CN=2)OC=2C=CC=CC=2)=N1 YFZOSVCOAMMSOO-UHFFFAOYSA-N 0.000 claims 1
- BDLLJQKBXFNLES-UHFFFAOYSA-N 2-[[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanylmethyl]pyridin-3-ol Chemical compound CC1=CSC(NC=2C(=CC(SCC=3C(=CC=CN=3)O)=CN=2)OC=2C=CC=CC=2)=N1 BDLLJQKBXFNLES-UHFFFAOYSA-N 0.000 claims 1
- NPBXCGVHSAFGHV-UHFFFAOYSA-N 2-amino-1-[4-[5-[(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 NPBXCGVHSAFGHV-UHFFFAOYSA-N 0.000 claims 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 1
- JCSZXBIMTCZGOX-UHFFFAOYSA-N 2-hydroxy-1-[4-[5-[(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CO)CCC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 JCSZXBIMTCZGOX-UHFFFAOYSA-N 0.000 claims 1
- CTCWRWPQHBJTGS-UHFFFAOYSA-N 3-(1-methylsulfonylpiperidin-4-yl)-n-(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)-1,2,4-thiadiazol-5-amine Chemical compound C1CN(S(=O)(=O)C)CCC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 CTCWRWPQHBJTGS-UHFFFAOYSA-N 0.000 claims 1
- MFKAJZCCGOHVKP-UHFFFAOYSA-N 3-(2-methylpropyl)-n-(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)-1,2,4-thiadiazol-5-amine Chemical compound CC(C)CC1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 MFKAJZCCGOHVKP-UHFFFAOYSA-N 0.000 claims 1
- QVKFVTKHQVFQKX-UHFFFAOYSA-N 3-(oxolan-2-yl)-n-(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)-1,2,4-thiadiazol-5-amine Chemical compound C1CCOC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 QVKFVTKHQVFQKX-UHFFFAOYSA-N 0.000 claims 1
- JWBFLCSRLCGPRZ-UHFFFAOYSA-N 3-(oxolan-2-yl)-n-[5-pyridin-2-ylsulfanyl-3-[4-(trifluoromethyl)phenoxy]pyridin-2-yl]-1,2,4-thiadiazol-5-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1=CC(SC=2N=CC=CC=2)=CN=C1NC1=NC(C2OCCC2)=NS1 JWBFLCSRLCGPRZ-UHFFFAOYSA-N 0.000 claims 1
- MWGGVTOAHVQBPC-UHFFFAOYSA-N 3-[1-(2-aminoethylsulfonyl)piperidin-4-yl]-n-(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)-1,2,4-thiadiazol-5-amine Chemical compound C1CN(S(=O)(=O)CCN)CCC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 MWGGVTOAHVQBPC-UHFFFAOYSA-N 0.000 claims 1
- CUZSJRPWTGMVSV-UHFFFAOYSA-N 3-[2-[(3-phenoxy-5-pyridin-4-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]propanoic acid Chemical compound OC(=O)CCC1=CSC(NC=2C(=CC(SC=3C=CN=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 CUZSJRPWTGMVSV-UHFFFAOYSA-N 0.000 claims 1
- AHGWPLFHDKMLPQ-UHFFFAOYSA-N 3-[2-[(4-methyl-1,3-thiazol-2-yl)amino]pyridin-3-yl]sulfanylphenol Chemical compound CC1=CSC(NC=2C(=CC=CN=2)SC=2C=C(O)C=CC=2)=N1 AHGWPLFHDKMLPQ-UHFFFAOYSA-N 0.000 claims 1
- KMYZCRJMRZXONJ-UHFFFAOYSA-N 3-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]-1-pyrrolidin-1-ylpropan-1-one Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CN=C1NC(SC=1)=NC=1CCC(=O)N1CCCC1 KMYZCRJMRZXONJ-UHFFFAOYSA-N 0.000 claims 1
- LAOZWQYHRQGDEQ-UHFFFAOYSA-N 3-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]-2,2-dimethylpropanoic acid Chemical compound OC(=O)C(C)(C)CC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 LAOZWQYHRQGDEQ-UHFFFAOYSA-N 0.000 claims 1
- CWEAIGCTEGUJGV-UHFFFAOYSA-N 3-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]-2-methoxy-2-methyl-1-pyrrolidin-1-ylpropan-1-one Chemical compound C1CCCN1C(=O)C(C)(OC)CC(N=1)=CSC=1NC1=NC=C(Br)C=C1OC1=CC=CC=C1 CWEAIGCTEGUJGV-UHFFFAOYSA-N 0.000 claims 1
- KZJDMYKYWMJQOQ-UHFFFAOYSA-N 3-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]-2-methoxy-2-methylpropanoic acid Chemical compound COC(C)(C(O)=O)CC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 KZJDMYKYWMJQOQ-UHFFFAOYSA-N 0.000 claims 1
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- OKJPNMYQNLOWMD-UHFFFAOYSA-N 4-methyl-n-[5-(oxan-4-ylmethyl)-3-phenylsulfanylpyridin-2-yl]-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(CC3CCOCC3)=CN=2)SC=2C=CC=CC=2)=N1 OKJPNMYQNLOWMD-UHFFFAOYSA-N 0.000 claims 1
- CCGKIHFXFSNWKG-UHFFFAOYSA-N 4-methyl-n-[5-[(1-methylpiperidin-4-yl)-pyridin-2-ylmethyl]sulfanyl-3-phenoxypyridin-2-yl]-1,3-thiazol-2-amine Chemical compound C1CN(C)CCC1C(C=1N=CC=CC=1)SC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 CCGKIHFXFSNWKG-UHFFFAOYSA-N 0.000 claims 1
- ZIOIVTLIWGZFFF-UHFFFAOYSA-N 4-methyl-n-[5-[(3-methyl-[1,2]oxazolo[5,4-b]pyridin-4-yl)sulfanyl]-3-phenoxypyridin-2-yl]-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=4C(C)=NOC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 ZIOIVTLIWGZFFF-UHFFFAOYSA-N 0.000 claims 1
- PRSUECFECYCBCQ-UHFFFAOYSA-N 4-methyl-n-[5-[(3-methyl-[1,2]oxazolo[5,4-b]pyridin-4-yl)sulfanyl]-3-phenylsulfanylpyridin-2-yl]-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=4C(C)=NOC=4N=CC=3)=CN=2)SC=2C=CC=CC=2)=N1 PRSUECFECYCBCQ-UHFFFAOYSA-N 0.000 claims 1
- FJASXWGOXUOMCC-UHFFFAOYSA-N 4-methyl-n-[5-[(4-methyl-1,2,4-triazol-3-yl)sulfanyl]-3-phenoxypyridin-2-yl]-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3N(C=NN=3)C)=CN=2)OC=2C=CC=CC=2)=N1 FJASXWGOXUOMCC-UHFFFAOYSA-N 0.000 claims 1
- NQRDGYVQGICGCY-UHFFFAOYSA-N 4-methyl-n-[5-[(4-methyl-1,3-thiazol-2-yl)sulfanyl]-3-phenoxypyridin-2-yl]-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3SC=C(C)N=3)=CN=2)OC=2C=CC=CC=2)=N1 NQRDGYVQGICGCY-UHFFFAOYSA-N 0.000 claims 1
- NQZVOAUPMBJFLQ-UHFFFAOYSA-N 4-methyl-n-[5-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-3-phenoxypyridin-2-yl]-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SCC3=NOC(C)=C3)=CN=2)OC=2C=CC=CC=2)=N1 NQZVOAUPMBJFLQ-UHFFFAOYSA-N 0.000 claims 1
- RRMQYTZQODJIIW-UHFFFAOYSA-N 4-methyl-n-[5-[(5-methyl-1,2-oxazol-3-yl)methylsulfanyl]-3-phenylsulfanylpyridin-2-yl]-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SCC3=NOC(C)=C3)=CN=2)SC=2C=CC=CC=2)=N1 RRMQYTZQODJIIW-UHFFFAOYSA-N 0.000 claims 1
- RNUHHOJLIGBKSO-CQSZACIVSA-N 4-methyl-n-[5-[[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]sulfanyl]-3-phenoxypyridin-2-yl]-1,3-thiazol-2-amine Chemical compound C([C@H](C=12)C)CC2=NC=NC=1SC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 RNUHHOJLIGBKSO-CQSZACIVSA-N 0.000 claims 1
- KVPJWHFULPEXLN-UHFFFAOYSA-N 5-(2-chlorophenyl)sulfanyl-6-[(4-methyl-1,3-thiazol-2-yl)amino]pyridin-3-ol Chemical compound CC1=CSC(NC=2C(=CC(O)=CN=2)SC=2C(=CC=CC=2)Cl)=N1 KVPJWHFULPEXLN-UHFFFAOYSA-N 0.000 claims 1
- GMLZJBGKNWWGMH-UHFFFAOYSA-N 5-[2-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]ethyl]-3h-1,3,4-oxadiazol-2-one Chemical compound O1C(O)=NN=C1CCC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 GMLZJBGKNWWGMH-UHFFFAOYSA-N 0.000 claims 1
- MBXJQBNXAIMRFD-UHFFFAOYSA-N 5-[6-[[4-(1-acetylpiperidin-4-yl)-1,3-thiazol-2-yl]amino]-5-phenoxypyridin-3-yl]sulfanyl-3-methoxypyridine-2-carbonitrile Chemical compound N1=C(C#N)C(OC)=CC(SC=2C=C(OC=3C=CC=CC=3)C(NC=3SC=C(N=3)C3CCN(CC3)C(C)=O)=NC=2)=C1 MBXJQBNXAIMRFD-UHFFFAOYSA-N 0.000 claims 1
- COOLWTWFUAHYTL-UHFFFAOYSA-N 6-[6-[[4-(1-acetylpiperidin-4-yl)-1,3-thiazol-2-yl]amino]-5-phenoxypyridin-3-yl]sulfanylpyridine-3-carbonitrile Chemical compound C1CN(C(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3N=CC(=CC=3)C#N)=CN=2)OC=2C=CC=CC=2)=N1 COOLWTWFUAHYTL-UHFFFAOYSA-N 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- DZQJRCLKXOXTGM-UHFFFAOYSA-N C(CC)(=O)OSC=1C=NC(=C(C=1)OC1=CC=CC=C1)NC=1SC=C(N=1)C1CCN(CC1)C Chemical compound C(CC)(=O)OSC=1C=NC(=C(C=1)OC1=CC=CC=C1)NC=1SC=C(N=1)C1CCN(CC1)C DZQJRCLKXOXTGM-UHFFFAOYSA-N 0.000 claims 1
- ZPMUAHQIHHFGHQ-UHFFFAOYSA-N CN(C)CCC1=NC=C(C(N)=O)N1C Chemical compound CN(C)CCC1=NC=C(C(N)=O)N1C ZPMUAHQIHHFGHQ-UHFFFAOYSA-N 0.000 claims 1
- WJRBIKBLYZKWHX-UHFFFAOYSA-N CS(N(CC1)CCC1C1=CSC(N)=N1)(=O)=O Chemical compound CS(N(CC1)CCC1C1=CSC(N)=N1)(=O)=O WJRBIKBLYZKWHX-UHFFFAOYSA-N 0.000 claims 1
- QGUJAAKAPJAONU-UHFFFAOYSA-N ClC1=C(C=CC=C1)SC=1C(=NC=C(C=1)SCCCN(C)C)C1=C(N=C(S1)N)C Chemical compound ClC1=C(C=CC=C1)SC=1C(=NC=C(C=1)SCCCN(C)C)C1=C(N=C(S1)N)C QGUJAAKAPJAONU-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- INZTXDSNLTUJJM-UHFFFAOYSA-N NC1=NC=CC=C1C1=NC(C2OCCC2)=NS1 Chemical compound NC1=NC=CC=C1C1=NC(C2OCCC2)=NS1 INZTXDSNLTUJJM-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- JCTKQLOQIGVQSL-UHFFFAOYSA-N [2-[5-bromo-2-[(4-methyl-1,3-thiazol-2-yl)amino]pyridin-3-yl]sulfanyl-3-methylimidazol-4-yl]methanol Chemical compound CC1=CSC(NC=2C(=CC(Br)=CN=2)SC=2N(C(CO)=CN=2)C)=N1 JCTKQLOQIGVQSL-UHFFFAOYSA-N 0.000 claims 1
- AXFLEADRTQMTQN-UHFFFAOYSA-N [4-[5-bromo-2-([1,3]thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-yl]sulfanylphenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1SC1=CC(Br)=CN=C1NC1=NC2=CC=CN=C2S1 AXFLEADRTQMTQN-UHFFFAOYSA-N 0.000 claims 1
- MLAFXDAGVYPDHZ-UHFFFAOYSA-N [6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]methanol Chemical compound CC1=CSC(NC=2C(=CC(CO)=CN=2)OC=2C=CC=CC=2)=N1 MLAFXDAGVYPDHZ-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- BYAVQLLNOBCSQP-UHFFFAOYSA-N ethyl 2-(1-methylpiperidin-4-yl)-2-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanylacetate Chemical compound C1CN(C)CCC1C(C(=O)OCC)SC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 BYAVQLLNOBCSQP-UHFFFAOYSA-N 0.000 claims 1
- NZBVAZLXGYIIBF-UHFFFAOYSA-N ethyl 2-[5-bromo-2-([1,3]thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-yl]sulfanyl-5-fluorobenzoate Chemical compound CCOC(=O)C1=CC(F)=CC=C1SC1=CC(Br)=CN=C1NC1=NC2=CC=CN=C2S1 NZBVAZLXGYIIBF-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HCXNYTIEOYAGCQ-UHFFFAOYSA-N methyl 2-[5-bromo-2-[(4-methyl-1,3-thiazol-2-yl)amino]pyridin-3-yl]sulfanyl-3-methylimidazole-4-carboxylate Chemical compound CN1C(C(=O)OC)=CN=C1SC1=CC(Br)=CN=C1NC1=NC(C)=CS1 HCXNYTIEOYAGCQ-UHFFFAOYSA-N 0.000 claims 1
- ZEVYELQKTSIDKI-UHFFFAOYSA-N methyl 3-[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]-2-methoxy-2-methylpropanoate Chemical compound COC(=O)C(C)(OC)CC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 ZEVYELQKTSIDKI-UHFFFAOYSA-N 0.000 claims 1
- XPBQORIAQMDSGU-UHFFFAOYSA-N methyl 3-[5-phenoxy-6-([1,3]thiazolo[5,4-b]pyridin-2-ylamino)pyridin-3-yl]sulfanylpropanoate Chemical compound C=1C(SCCC(=O)OC)=CN=C(NC=2SC3=NC=CC=C3N=2)C=1OC1=CC=CC=C1 XPBQORIAQMDSGU-UHFFFAOYSA-N 0.000 claims 1
- VRWRVPKWVAWSQG-UHFFFAOYSA-N methyl 3-[5-phenoxy-6-[[4-(2-phenylethyl)-1,3-thiazol-2-yl]amino]pyridin-3-yl]sulfanylpropanoate Chemical compound C=1C=CC=CC=1OC1=CC(SCCC(=O)OC)=CN=C1NC(SC=1)=NC=1CCC1=CC=CC=C1 VRWRVPKWVAWSQG-UHFFFAOYSA-N 0.000 claims 1
- SJKDPYJLHQMNBE-UHFFFAOYSA-N methyl 3-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]propanoate Chemical compound C=1C=CC=CC=1OC1=CC(CCC(=O)OC)=CN=C1NC1=NC(C)=CS1 SJKDPYJLHQMNBE-UHFFFAOYSA-N 0.000 claims 1
- ZLZOAWUKQKRPKA-UHFFFAOYSA-N methyl 3-[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanylpropanoate Chemical compound C=1C=CC=CC=1OC1=CC(SCCC(=O)OC)=CN=C1NC1=NC(C)=CS1 ZLZOAWUKQKRPKA-UHFFFAOYSA-N 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- YOWJJIQTYFKXJC-UHFFFAOYSA-N n-(3-benzylpyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC=CN=2)CC=2C=CC=CC=2)=N1 YOWJJIQTYFKXJC-UHFFFAOYSA-N 0.000 claims 1
- JAVCMWCFDMXTLK-UHFFFAOYSA-N n-(3-cyclohex-2-en-1-yloxypyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC=CN=2)OC2C=CCCC2)=N1 JAVCMWCFDMXTLK-UHFFFAOYSA-N 0.000 claims 1
- GKNJTCDWFQVTOT-UHFFFAOYSA-N n-(3-cyclopentyloxypyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC=CN=2)OC2CCCC2)=N1 GKNJTCDWFQVTOT-UHFFFAOYSA-N 0.000 claims 1
- VMPDTCFYEZILIA-UHFFFAOYSA-N n-(3-cyclopentylsulfanylpyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC=CN=2)SC2CCCC2)=N1 VMPDTCFYEZILIA-UHFFFAOYSA-N 0.000 claims 1
- XXNRDNXIPHATNM-UHFFFAOYSA-N n-(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)-3-piperidin-4-yl-1,2,4-thiadiazol-5-amine Chemical compound C1CNCCC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 XXNRDNXIPHATNM-UHFFFAOYSA-N 0.000 claims 1
- XHIIDSXYTHAOPT-UHFFFAOYSA-N n-(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)-3-propan-2-yl-1,2,4-thiadiazol-5-amine Chemical compound CC(C)C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 XHIIDSXYTHAOPT-UHFFFAOYSA-N 0.000 claims 1
- LOBWGDVLPZAVJN-UHFFFAOYSA-N n-(3-phenoxy-5-pyridin-4-ylsulfanylpyridin-2-yl)-1,3-thiazol-2-amine Chemical compound N=1C=C(SC=2C=CN=CC=2)C=C(OC=2C=CC=CC=2)C=1NC1=NC=CS1 LOBWGDVLPZAVJN-UHFFFAOYSA-N 0.000 claims 1
- ZVHBWHZMVDWUFE-UHFFFAOYSA-N n-(3-phenoxy-5-pyridin-4-ylsulfanylpyridin-2-yl)-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound C=1SC(NC=2C(=CC(SC=3C=CN=CC=3)=CN=2)OC=2C=CC=CC=2)=NC=1CCC1=CC=CC=C1 ZVHBWHZMVDWUFE-UHFFFAOYSA-N 0.000 claims 1
- DELIHZQMIGWCMS-UHFFFAOYSA-N n-(3-phenoxy-5-pyridin-4-ylsulfanylpyridin-2-yl)-4-(trifluoromethyl)-1,3-thiazol-2-amine Chemical compound FC(F)(F)C1=CSC(NC=2C(=CC(SC=3C=CN=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 DELIHZQMIGWCMS-UHFFFAOYSA-N 0.000 claims 1
- OTHCFNKJJNBAHS-UHFFFAOYSA-N n-(3-phenoxy-5-pyridin-4-ylsulfanylpyridin-2-yl)-4-phenyl-1,3-thiazol-2-amine Chemical compound N=1C=C(SC=2C=CN=CC=2)C=C(OC=2C=CC=CC=2)C=1NC(SC=1)=NC=1C1=CC=CC=C1 OTHCFNKJJNBAHS-UHFFFAOYSA-N 0.000 claims 1
- CPUQJZUHAKVNGU-UHFFFAOYSA-N n-(3-phenoxy-5-pyridin-4-ylsulfanylpyridin-2-yl)-4-propan-2-yl-1,3-thiazol-2-amine Chemical compound CC(C)C1=CSC(NC=2C(=CC(SC=3C=CN=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 CPUQJZUHAKVNGU-UHFFFAOYSA-N 0.000 claims 1
- FNOFZZWOFRKSOD-UHFFFAOYSA-N n-(3-phenoxy-5-pyridin-4-ylsulfanylpyridin-2-yl)-4-pyridin-2-yl-1,3-thiazol-2-amine Chemical compound N=1C=C(SC=2C=CN=CC=2)C=C(OC=2C=CC=CC=2)C=1NC(SC=1)=NC=1C1=CC=CC=N1 FNOFZZWOFRKSOD-UHFFFAOYSA-N 0.000 claims 1
- UEZNYUKNSCLCFQ-UHFFFAOYSA-N n-(3-phenoxy-5-pyridin-4-ylsulfanylpyridin-2-yl)-4-thiophen-3-yl-1,3-thiazol-2-amine Chemical compound N=1C=C(SC=2C=CN=CC=2)C=C(OC=2C=CC=CC=2)C=1NC(SC=1)=NC=1C=1C=CSC=1 UEZNYUKNSCLCFQ-UHFFFAOYSA-N 0.000 claims 1
- UFGFJPOMCJUHOS-UHFFFAOYSA-N n-(3-phenoxy-5-pyridin-4-ylsulfanylpyridin-2-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N=1C2=CC=CN=C2SC=1NC(C(=C1)OC=2C=CC=CC=2)=NC=C1SC1=CC=NC=C1 UFGFJPOMCJUHOS-UHFFFAOYSA-N 0.000 claims 1
- RODJHCWKGJNQDB-UHFFFAOYSA-N n-(3-phenoxy-5-pyrimidin-2-ylsulfanylpyridin-2-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N=1C2=CC=CN=C2SC=1NC(C(=C1)OC=2C=CC=CC=2)=NC=C1SC1=NC=CC=N1 RODJHCWKGJNQDB-UHFFFAOYSA-N 0.000 claims 1
- PZKBNYWYNLNKBR-UHFFFAOYSA-N n-(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)-3-pyrrolidin-3-yl-1,2,4-thiadiazol-5-amine Chemical compound C1NCCC1C1=NSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 PZKBNYWYNLNKBR-UHFFFAOYSA-N 0.000 claims 1
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- LSOPRPPJIQOINK-UHFFFAOYSA-N n-(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)-4-(piperidin-4-ylmethyl)-1,3-thiazol-2-amine Chemical compound C=1SC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=NC=1CC1CCNCC1 LSOPRPPJIQOINK-UHFFFAOYSA-N 0.000 claims 1
- MRZIRFQPVIADAN-UHFFFAOYSA-N n-(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)-4-piperidin-3-yl-1,3-thiazol-2-amine Chemical compound C1CCNCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 MRZIRFQPVIADAN-UHFFFAOYSA-N 0.000 claims 1
- MQNRCPSAFDGRCY-UHFFFAOYSA-N n-(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)-4-pyrrolidin-3-yl-1,3-thiazol-2-amine Chemical compound C1NCCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 MQNRCPSAFDGRCY-UHFFFAOYSA-N 0.000 claims 1
- VXLVZMKQZZSYKI-UHFFFAOYSA-N n-(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N=1C2=CC=CN=C2SC=1NC1=NC=C(SC=2C=3SC=CC=3N=CC=2)C=C1OC1=CC=CC=C1 VXLVZMKQZZSYKI-UHFFFAOYSA-N 0.000 claims 1
- XRLRWLLCLOGHSM-UHFFFAOYSA-N n-(3-phenoxy-5-thieno[3,2-d]pyrimidin-4-ylsulfanylpyridin-2-yl)-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound C=1SC(NC=2C(=CC(SC=3C=4SC=CC=4N=CN=3)=CN=2)OC=2C=CC=CC=2)=NC=1CCC1=CC=CC=C1 XRLRWLLCLOGHSM-UHFFFAOYSA-N 0.000 claims 1
- JXYKOCIOFMKWDO-UHFFFAOYSA-N n-(3-phenylsulfanyl-5-pyridin-2-ylsulfanylpyridin-2-yl)-4-piperidin-4-yl-1,3-thiazol-2-amine Chemical compound C1CNCCC1C1=CSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)SC=2C=CC=CC=2)=N1 JXYKOCIOFMKWDO-UHFFFAOYSA-N 0.000 claims 1
- OKTAVHBBSKBRFV-UHFFFAOYSA-N n-(3-phenylsulfanyl-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)-3-piperidin-4-yl-1,2,4-thiadiazol-5-amine Chemical compound C1CNCCC1C1=NSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)SC=2C=CC=CC=2)=N1 OKTAVHBBSKBRFV-UHFFFAOYSA-N 0.000 claims 1
- IWQWHQMBKYLUOS-UHFFFAOYSA-N n-(3-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound N=1C2=CC=CN=C2SC=1NC1=NC=CC=C1SC1=CC=NC2=C1SC=C2 IWQWHQMBKYLUOS-UHFFFAOYSA-N 0.000 claims 1
- ICFDGIUNTZOZLF-UHFFFAOYSA-N n-(5-benzylsulfanyl-3-phenoxypyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SCC=3C=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 ICFDGIUNTZOZLF-UHFFFAOYSA-N 0.000 claims 1
- ZIVBOUODAHFKCO-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-3-(2-methylpropyl)-1,2,4-thiadiazol-5-amine Chemical compound CC(C)CC1=NSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 ZIVBOUODAHFKCO-UHFFFAOYSA-N 0.000 claims 1
- DCNDSBROKGPIPQ-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-3-(oxolan-2-yl)-1,2,4-thiadiazol-5-amine Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CN=C1NC(SN=1)=NC=1C1CCCO1 DCNDSBROKGPIPQ-UHFFFAOYSA-N 0.000 claims 1
- INPKQMZUIPJNGQ-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-3-methyl-1,2,4-thiadiazol-5-amine Chemical compound CC1=NSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 INPKQMZUIPJNGQ-UHFFFAOYSA-N 0.000 claims 1
- KVJXYYGEUNTLDF-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-3-piperidin-4-yl-1,2,4-thiadiazol-5-amine Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CN=C1NC(SN=1)=NC=1C1CCNCC1 KVJXYYGEUNTLDF-UHFFFAOYSA-N 0.000 claims 1
- YHCWWWAGTXXENT-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-(1-methylpiperidin-4-yl)-1,3-thiazol-2-amine Chemical compound C1CN(C)CCC1C1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 YHCWWWAGTXXENT-UHFFFAOYSA-N 0.000 claims 1
- IFANAIDXIPIXLD-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-(2-methylsulfanylethyl)-1,3-thiazol-2-amine Chemical compound CSCCC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 IFANAIDXIPIXLD-UHFFFAOYSA-N 0.000 claims 1
- UDSJQOSUWWDAEG-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-(2-methylsulfonylethyl)-1,3-thiazol-2-amine Chemical compound CS(=O)(=O)CCC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 UDSJQOSUWWDAEG-UHFFFAOYSA-N 0.000 claims 1
- GBPWMVNIWSOASF-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CN=C1NC(SC=1)=NC=1CCC1=CC=CC=C1 GBPWMVNIWSOASF-UHFFFAOYSA-N 0.000 claims 1
- FDZKXXJZGMFGMX-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-(chloromethyl)-1,3-thiazol-2-amine Chemical compound ClCC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 FDZKXXJZGMFGMX-UHFFFAOYSA-N 0.000 claims 1
- BCXZONOBINSEMY-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-(phenoxymethyl)-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CN=C1NC(SC=1)=NC=1COC1=CC=CC=C1 BCXZONOBINSEMY-UHFFFAOYSA-N 0.000 claims 1
- NHRXQTVWCAQIFN-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-(phenylsulfanylmethyl)-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CN=C1NC(SC=1)=NC=1CSC1=CC=CC=C1 NHRXQTVWCAQIFN-UHFFFAOYSA-N 0.000 claims 1
- GBPHLUYHZNRHMQ-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-(pyrrolidin-1-ylmethyl)-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CN=C1NC(SC=1)=NC=1CN1CCCC1 GBPHLUYHZNRHMQ-UHFFFAOYSA-N 0.000 claims 1
- ATOSWJDEDCBDKI-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-1,3-thiazol-2-amine Chemical compound CC1=NOC(CC=2N=C(NC=3C(=CC(Br)=CN=3)OC=3C=CC=CC=3)SC=2)=N1 ATOSWJDEDCBDKI-UHFFFAOYSA-N 0.000 claims 1
- NVIFNXFXCIQKHW-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-1,3-thiazol-2-amine Chemical compound O1C(C)=NN=C1CC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 NVIFNXFXCIQKHW-UHFFFAOYSA-N 0.000 claims 1
- DXWCYVCRQUSOIH-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-[(5-methyl-1,3-oxazol-2-yl)methyl]-1,3-thiazol-2-amine Chemical compound O1C(C)=CN=C1CC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 DXWCYVCRQUSOIH-UHFFFAOYSA-N 0.000 claims 1
- ULSLPPPJZBKPQV-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-[2-(2h-tetrazol-5-yl)ethyl]-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CN=C1NC(SC=1)=NC=1CCC1=NN=NN1 ULSLPPPJZBKPQV-UHFFFAOYSA-N 0.000 claims 1
- RSSOPBNWMKCGAS-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-[2-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-1,3-thiazol-2-amine Chemical compound CC1=NOC(CCC=2N=C(NC=3C(=CC(Br)=CN=3)OC=3C=CC=CC=3)SC=2)=N1 RSSOPBNWMKCGAS-UHFFFAOYSA-N 0.000 claims 1
- ZYKRRWOBVPFYAS-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-[2-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]-1,3-thiazol-2-amine Chemical compound O1C(C)=NC(CCC=2N=C(NC=3C(=CC(Br)=CN=3)OC=3C=CC=CC=3)SC=2)=N1 ZYKRRWOBVPFYAS-UHFFFAOYSA-N 0.000 claims 1
- WIPALWJNCCGCTC-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-[2-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl]-1,3-thiazol-2-amine Chemical compound O1C(C)=NN=C1CCC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 WIPALWJNCCGCTC-UHFFFAOYSA-N 0.000 claims 1
- FMSNEYROWPBXNY-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-[2-(5-methyl-1,3-oxazol-2-yl)ethyl]-1,3-thiazol-2-amine Chemical compound O1C(C)=CN=C1CCC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 FMSNEYROWPBXNY-UHFFFAOYSA-N 0.000 claims 1
- ZHGAJQCKKHRGBH-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-[2-(5-propan-2-yl-1,3,4-oxadiazol-2-yl)ethyl]-1,3-thiazol-2-amine Chemical compound O1C(C(C)C)=NN=C1CCC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 ZHGAJQCKKHRGBH-UHFFFAOYSA-N 0.000 claims 1
- XRFBFVJFPOWVBV-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 XRFBFVJFPOWVBV-UHFFFAOYSA-N 0.000 claims 1
- CJRNUXZCFPZOET-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-4-piperidin-4-yl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CN=C1NC(SC=1)=NC=1C1CCNCC1 CJRNUXZCFPZOET-UHFFFAOYSA-N 0.000 claims 1
- PFRNRUIFRGXTDT-UHFFFAOYSA-N n-(5-bromo-3-phenoxypyridin-2-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C=1C(Br)=CN=C(NC=2SC3=NC=CC=C3N=2)C=1OC1=CC=CC=C1 PFRNRUIFRGXTDT-UHFFFAOYSA-N 0.000 claims 1
- KKLREPWMDPWINJ-UHFFFAOYSA-N n-(5-bromo-3-phenylsulfanylpyridin-2-yl)-3-methyl-1,2,4-oxadiazol-5-amine Chemical compound CC1=NOC(NC=2C(=CC(Br)=CN=2)SC=2C=CC=CC=2)=N1 KKLREPWMDPWINJ-UHFFFAOYSA-N 0.000 claims 1
- GAVNDGUOVMJRHF-UHFFFAOYSA-N n-(5-bromo-3-phenylsulfanylpyridin-2-yl)-3-methyl-1,2,4-thiadiazol-5-amine Chemical compound CC1=NSC(NC=2C(=CC(Br)=CN=2)SC=2C=CC=CC=2)=N1 GAVNDGUOVMJRHF-UHFFFAOYSA-N 0.000 claims 1
- CVOHNOTWXBPCOU-UHFFFAOYSA-N n-(5-bromo-3-phenylsulfanylpyridin-2-yl)-3-propan-2-yl-1,2,4-thiadiazol-5-amine Chemical compound CC(C)C1=NSC(NC=2C(=CC(Br)=CN=2)SC=2C=CC=CC=2)=N1 CVOHNOTWXBPCOU-UHFFFAOYSA-N 0.000 claims 1
- MHNHPJBQEMLFTL-UHFFFAOYSA-N n-(5-bromo-3-phenylsulfanylpyridin-2-yl)-4-[2-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl]-1,3-thiazol-2-amine Chemical compound O1C(C)=NN=C1CCC1=CSC(NC=2C(=CC(Br)=CN=2)SC=2C=CC=CC=2)=N1 MHNHPJBQEMLFTL-UHFFFAOYSA-N 0.000 claims 1
- HCIRHORVBRYWCP-UHFFFAOYSA-N n-(5-bromo-3-phenylsulfanylpyridin-2-yl)-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C=1C(Br)=CN=C(NC=2SC3=NC=CC=C3N=2)C=1SC1=CC=CC=C1 HCIRHORVBRYWCP-UHFFFAOYSA-N 0.000 claims 1
- IMOHOXBZSXTOHV-UHFFFAOYSA-N n-(5-bromo-3-pyrimidin-2-ylsulfanylpyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(Br)=CN=2)SC=2N=CC=CN=2)=N1 IMOHOXBZSXTOHV-UHFFFAOYSA-N 0.000 claims 1
- MSTPRMYSYPSSJY-UHFFFAOYSA-N n-(5-chloro-3-phenoxypyridin-2-yl)-4,5-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(C)=C(C)N=C1NC1=NC=C(Cl)C=C1OC1=CC=CC=C1 MSTPRMYSYPSSJY-UHFFFAOYSA-N 0.000 claims 1
- PHUFEHZWAZPJCF-UHFFFAOYSA-N n-(5-chloro-3-phenoxypyridin-2-yl)-4-(2-methylpropyl)-1,3-thiazol-2-amine Chemical compound CC(C)CC1=CSC(NC=2C(=CC(Cl)=CN=2)OC=2C=CC=CC=2)=N1 PHUFEHZWAZPJCF-UHFFFAOYSA-N 0.000 claims 1
- QWKZSVFIEQFOIR-UHFFFAOYSA-N n-(5-chloro-3-phenoxypyridin-2-yl)-4-cyclopropyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1OC1=CC(Cl)=CN=C1NC(SC=1)=NC=1C1CC1 QWKZSVFIEQFOIR-UHFFFAOYSA-N 0.000 claims 1
- VNYJRZHTYDZDBX-UHFFFAOYSA-N n-(5-chloro-3-phenoxypyridin-2-yl)-4-ethyl-1,3-thiazol-2-amine Chemical compound CCC1=CSC(NC=2C(=CC(Cl)=CN=2)OC=2C=CC=CC=2)=N1 VNYJRZHTYDZDBX-UHFFFAOYSA-N 0.000 claims 1
- QAXSICFRGTWUGW-UHFFFAOYSA-N n-(5-chloro-3-phenoxypyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(Cl)=CN=2)OC=2C=CC=CC=2)=N1 QAXSICFRGTWUGW-UHFFFAOYSA-N 0.000 claims 1
- BXTIRCRUGBXQPV-UHFFFAOYSA-N n-(5-cyclohexylsulfanyl-3-phenoxypyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC3CCCCC3)=CN=2)OC=2C=CC=CC=2)=N1 BXTIRCRUGBXQPV-UHFFFAOYSA-N 0.000 claims 1
- WLKKYJTUGFQXMN-UHFFFAOYSA-N n-(5-furo[3,2-c]pyridin-4-ylsulfanyl-3-phenoxypyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=4C=COC=4C=CN=3)=CN=2)OC=2C=CC=CC=2)=N1 WLKKYJTUGFQXMN-UHFFFAOYSA-N 0.000 claims 1
- NLKZQMMEHYPIJH-UHFFFAOYSA-N n-(5-methoxy-3-phenoxypyridin-2-yl)-4-methyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1OC1=CC(OC)=CN=C1NC1=NC(C)=CS1 NLKZQMMEHYPIJH-UHFFFAOYSA-N 0.000 claims 1
- RBHKNDALAJHGNN-UHFFFAOYSA-N n-[1-[4-[2-[[3-(4-fluorophenoxy)-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]-1-oxopropan-2-yl]acetamide Chemical compound C1CN(C(=O)C(NC(C)=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC(F)=CC=2)=N1 RBHKNDALAJHGNN-UHFFFAOYSA-N 0.000 claims 1
- CUIJELFPDVKLSJ-UHFFFAOYSA-N n-[2-[4-[2-[[3-(4-fluorophenoxy)-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl]amino]-1,3-thiazol-4-yl]piperidin-1-yl]-2-oxoethyl]acetamide Chemical compound C1CN(C(=O)CNC(=O)C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC(F)=CC=2)=N1 CUIJELFPDVKLSJ-UHFFFAOYSA-N 0.000 claims 1
- XHXHYJOUKOXJTJ-UHFFFAOYSA-N n-[3,5-bis(phenylsulfanyl)pyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=CC=CC=3)=CN=2)SC=2C=CC=CC=2)=N1 XHXHYJOUKOXJTJ-UHFFFAOYSA-N 0.000 claims 1
- WXGMRPGMTXZAHH-UHFFFAOYSA-N n-[3-(1-methylimidazol-2-yl)sulfanylpyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound CN1C=CN=C1SC1=CC=CN=C1NC1=NC2=CC=CN=C2S1 WXGMRPGMTXZAHH-UHFFFAOYSA-N 0.000 claims 1
- FUNXDHDDNIBQLZ-UHFFFAOYSA-N n-[3-(2,6-dichlorophenyl)sulfanylpyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC=CN=2)SC=2C(=CC=CC=2Cl)Cl)=N1 FUNXDHDDNIBQLZ-UHFFFAOYSA-N 0.000 claims 1
- CUNMSXMHHPYQOG-UHFFFAOYSA-N n-[3-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenyl)sulfanylpyridin-2-yl]-4-piperidin-4-yl-1,3-thiazol-2-amine Chemical compound COC1=CC=CC(SC=2C=C(OC=3C(=CC(F)=CC=3)Br)C(NC=3SC=C(N=3)C3CCNCC3)=NC=2)=C1 CUNMSXMHHPYQOG-UHFFFAOYSA-N 0.000 claims 1
- JTAWEBQTVJTKFT-UHFFFAOYSA-N n-[3-(2-bromo-5-morpholin-4-ylphenoxy)pyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC=CN=2)OC=2C(=CC=C(C=2)N2CCOCC2)Br)=N1 JTAWEBQTVJTKFT-UHFFFAOYSA-N 0.000 claims 1
- WYOFPHLFFREYLO-UHFFFAOYSA-N n-[3-(2-chlorophenyl)sulfanyl-5-[3-(dimethylamino)propylsulfanyl]pyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=C(Cl)C=1SC1=CC(SCCCN(C)C)=CN=C1NC1=NC(C)=CS1 WYOFPHLFFREYLO-UHFFFAOYSA-N 0.000 claims 1
- UNFKWHKVFGBMCJ-UHFFFAOYSA-N n-[3-(2-chlorophenyl)sulfanyl-5-pyridin-4-ylsulfanylpyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=CN=CC=3)=CN=2)SC=2C(=CC=CC=2)Cl)=N1 UNFKWHKVFGBMCJ-UHFFFAOYSA-N 0.000 claims 1
- KZTJLGQWIBXHPO-UHFFFAOYSA-N n-[3-(2-chlorophenyl)sulfanyl-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)SC=2C(=CC=CC=2)Cl)=N1 KZTJLGQWIBXHPO-UHFFFAOYSA-N 0.000 claims 1
- FKSCYYRJKFVRMY-UHFFFAOYSA-N n-[3-(2-chlorophenyl)sulfanylpyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC=CN=2)SC=2C(=CC=CC=2)Cl)=N1 FKSCYYRJKFVRMY-UHFFFAOYSA-N 0.000 claims 1
- AHHZQRSGDZDXNX-UHFFFAOYSA-N n-[3-(2-fluorophenyl)sulfanyl-5-phenylsulfanylpyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=CC=CC=3)=CN=2)SC=2C(=CC=CC=2)F)=N1 AHHZQRSGDZDXNX-UHFFFAOYSA-N 0.000 claims 1
- ATHASTOSRSDHEV-UHFFFAOYSA-N n-[3-(3-methoxyphenyl)sulfanylpyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound COC1=CC=CC(SC=2C(=NC=CC=2)NC=2SC=C(C)N=2)=C1 ATHASTOSRSDHEV-UHFFFAOYSA-N 0.000 claims 1
- WAURKBLSZQEHGM-UHFFFAOYSA-N n-[3-(4-fluorophenoxy)-5-(2-methylthieno[3,2-b]pyridin-7-yl)sulfanylpyridin-2-yl]-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound C=12SC(C)=CC2=NC=CC=1SC(C=C1OC=2C=CC(F)=CC=2)=CN=C1NC(SC=1)=NC=1CCC1=CC=CC=C1 WAURKBLSZQEHGM-UHFFFAOYSA-N 0.000 claims 1
- YDEFFAPIKIETKK-UHFFFAOYSA-N n-[3-(4-fluorophenoxy)-5-(5-methylpyrazolo[1,5-a]pyrimidin-7-yl)sulfanylpyridin-2-yl]-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound N12N=CC=C2N=C(C)C=C1SC(C=C1OC=2C=CC(F)=CC=2)=CN=C1NC(SC=1)=NC=1CCC1=CC=CC=C1 YDEFFAPIKIETKK-UHFFFAOYSA-N 0.000 claims 1
- ZPRZPIMKXQQJPA-UHFFFAOYSA-N n-[3-(4-fluorophenoxy)-5-[(3-methyl-[1,2]oxazolo[5,4-b]pyridin-4-yl)sulfanyl]pyridin-2-yl]-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound C=12C(C)=NOC2=NC=CC=1SC(C=C1OC=2C=CC(F)=CC=2)=CN=C1NC(SC=1)=NC=1CCC1=CC=CC=C1 ZPRZPIMKXQQJPA-UHFFFAOYSA-N 0.000 claims 1
- OQAXVLSCKNMVNG-UHFFFAOYSA-N n-[3-(4-fluorophenoxy)-5-[(3-methyl-[1,2]oxazolo[5,4-b]pyridin-4-yl)sulfanyl]pyridin-2-yl]-4-piperidin-4-yl-1,3-thiazol-2-amine Chemical compound C=12C(C)=NOC2=NC=CC=1SC(C=C1OC=2C=CC(F)=CC=2)=CN=C1NC(SC=1)=NC=1C1CCNCC1 OQAXVLSCKNMVNG-UHFFFAOYSA-N 0.000 claims 1
- YURHXCQKJZETKQ-UHFFFAOYSA-N n-[3-(4-fluorophenoxy)-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl]-3-(1-methylsulfonylpiperidin-4-yl)-1,2,4-thiadiazol-5-amine Chemical compound C1CN(S(=O)(=O)C)CCC1C1=NSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC(F)=CC=2)=N1 YURHXCQKJZETKQ-UHFFFAOYSA-N 0.000 claims 1
- BVCWFIJQSNGAHJ-UHFFFAOYSA-N n-[3-(4-fluorophenoxy)-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl]-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound C1=CC(F)=CC=C1OC1=CC(SC=2C=3SC=CC=3N=CC=2)=CN=C1NC1=NC(CCC=2C=CC=CC=2)=CS1 BVCWFIJQSNGAHJ-UHFFFAOYSA-N 0.000 claims 1
- NADUBKUJSSJCCJ-UHFFFAOYSA-N n-[3-(4-fluorophenoxy)-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl]-4-piperidin-4-yl-1,3-thiazol-2-amine Chemical compound C1=CC(F)=CC=C1OC1=CC(SC=2C=3SC=CC=3N=CC=2)=CN=C1NC1=NC(C2CCNCC2)=CS1 NADUBKUJSSJCCJ-UHFFFAOYSA-N 0.000 claims 1
- ZKUKYVYCLGHYCR-UHFFFAOYSA-N n-[3-phenoxy-5-(piperidin-4-ylmethylsulfanyl)pyridin-2-yl]-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound C=1SC(NC=2C(=CC(SCC3CCNCC3)=CN=2)OC=2C=CC=CC=2)=NC=1CCC1=CC=CC=C1 ZKUKYVYCLGHYCR-UHFFFAOYSA-N 0.000 claims 1
- FLGWLHIPACWBMD-UHFFFAOYSA-N n-[4-[[6-[(4-methyl-1,3-thiazol-2-yl)amino]-5-phenoxypyridin-3-yl]sulfanylmethyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(CSC=2C=C(OC=3C=CC=CC=3)C(NC=3SC=C(C)N=3)=NC=2)=C1 FLGWLHIPACWBMD-UHFFFAOYSA-N 0.000 claims 1
- VJHRGXLBZPURFQ-UHFFFAOYSA-N n-[5-(2,5-dichlorophenyl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C(=CC=C(Cl)C=3)Cl)=CN=2)OC=2C=CC=CC=2)=N1 VJHRGXLBZPURFQ-UHFFFAOYSA-N 0.000 claims 1
- FXKZKCDFOZJFQN-UHFFFAOYSA-N n-[5-(2,5-dimethoxyphenyl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound COC1=CC=C(OC)C(SC=2C=C(OC=3C=CC=CC=3)C(NC=3SC=C(C)N=3)=NC=2)=C1 FXKZKCDFOZJFQN-UHFFFAOYSA-N 0.000 claims 1
- RYQNHVXQOUTDOT-UHFFFAOYSA-N n-[5-(2,5-dimethylphenyl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C(=CC=C(C)C=3)C)=CN=2)OC=2C=CC=CC=2)=N1 RYQNHVXQOUTDOT-UHFFFAOYSA-N 0.000 claims 1
- AGGMPYTYVSEGJK-UHFFFAOYSA-N n-[5-(2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl)sulfanyl-3-(4-fluorophenoxy)pyridin-2-yl]-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound N12N=C(C)C=C2N=C(C)C=C1SC(C=C1OC=2C=CC(F)=CC=2)=CN=C1NC(SC=1)=NC=1CCC1=CC=CC=C1 AGGMPYTYVSEGJK-UHFFFAOYSA-N 0.000 claims 1
- PDUALVDYXDMKSS-UHFFFAOYSA-N n-[5-(2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl)sulfanyl-3-phenoxypyridin-2-yl]-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound N12N=C(C)C=C2N=C(C)C=C1SC(C=C1OC=2C=CC=CC=2)=CN=C1NC(SC=1)=NC=1CCC1=CC=CC=C1 PDUALVDYXDMKSS-UHFFFAOYSA-N 0.000 claims 1
- DRXPIVANAGWFRX-UHFFFAOYSA-N n-[5-(2-chloro-5-methoxyphenyl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound COC1=CC=C(Cl)C(SC=2C=C(OC=3C=CC=CC=3)C(NC=3SC=C(C)N=3)=NC=2)=C1 DRXPIVANAGWFRX-UHFFFAOYSA-N 0.000 claims 1
- AOBMOKDONAYUKZ-UHFFFAOYSA-N n-[5-(2-chloropyrimidin-4-yl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3N=C(Cl)N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 AOBMOKDONAYUKZ-UHFFFAOYSA-N 0.000 claims 1
- RQUFERRLHLMUNY-UHFFFAOYSA-N n-[5-(2-iodothieno[3,2-b]pyridin-7-yl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=4SC(I)=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 RQUFERRLHLMUNY-UHFFFAOYSA-N 0.000 claims 1
- LNFVCFATVFISIQ-UHFFFAOYSA-N n-[5-(2-iodothieno[3,2-b]pyridin-7-yl)sulfanyl-3-phenoxypyridin-2-yl]-4-piperidin-4-yl-1,3-thiazol-2-amine Chemical compound C=12SC(I)=CC2=NC=CC=1SC(C=C1OC=2C=CC=CC=2)=CN=C1NC(SC=1)=NC=1C1CCNCC1 LNFVCFATVFISIQ-UHFFFAOYSA-N 0.000 claims 1
- JTGHDONKRMXCRD-UHFFFAOYSA-N n-[5-(2-methylthieno[3,2-b]pyridin-7-yl)sulfanyl-3-phenoxypyridin-2-yl]-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound C=12SC(C)=CC2=NC=CC=1SC(C=C1OC=2C=CC=CC=2)=CN=C1NC(SC=1)=NC=1CCC1=CC=CC=C1 JTGHDONKRMXCRD-UHFFFAOYSA-N 0.000 claims 1
- IAOWTKNQXHOXHT-UHFFFAOYSA-N n-[5-(3-bromophenoxy)-3-(3-methoxyphenyl)sulfanylpyridin-2-yl]-3-(oxolan-2-yl)-1,2,4-thiadiazol-5-amine Chemical compound COC1=CC=CC(SC=2C(=NC=C(OC=3C=C(Br)C=CC=3)C=2)NC=2SN=C(N=2)C2OCCC2)=C1 IAOWTKNQXHOXHT-UHFFFAOYSA-N 0.000 claims 1
- LXROYGKHDHTOGJ-UHFFFAOYSA-N n-[5-(4,6-dimethoxypyrimidin-2-yl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound COC1=CC(OC)=NC(SC=2C=C(OC=3C=CC=CC=3)C(NC=3SC=C(C)N=3)=NC=2)=N1 LXROYGKHDHTOGJ-UHFFFAOYSA-N 0.000 claims 1
- XWZWSUFDQPTKLU-UHFFFAOYSA-N n-[5-(4,6-dimethylpyrimidin-2-yl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3N=C(C)C=C(C)N=3)=CN=2)OC=2C=CC=CC=2)=N1 XWZWSUFDQPTKLU-UHFFFAOYSA-N 0.000 claims 1
- FLTRELBVASKVTJ-UHFFFAOYSA-N n-[5-(4-methoxyphenyl)sulfanyl-3-phenoxypyridin-2-yl]-3-methyl-1,2,4-thiadiazol-5-amine Chemical compound C1=CC(OC)=CC=C1SC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=NS1 FLTRELBVASKVTJ-UHFFFAOYSA-N 0.000 claims 1
- DEGRRIJHECPKKX-UHFFFAOYSA-N n-[5-(4-methoxypyrimidin-2-yl)sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound COC1=CC=NC(SC=2C=C(OC=3C=CC=CC=3)C(NC=3SC=C(C)N=3)=NC=2)=N1 DEGRRIJHECPKKX-UHFFFAOYSA-N 0.000 claims 1
- MTKXEONPGVLPRS-UHFFFAOYSA-N n-[5-(5-methylpyrazolo[1,5-a]pyrimidin-7-yl)sulfanyl-3-phenoxypyridin-2-yl]-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound N12N=CC=C2N=C(C)C=C1SC(C=C1OC=2C=CC=CC=2)=CN=C1NC(SC=1)=NC=1CCC1=CC=CC=C1 MTKXEONPGVLPRS-UHFFFAOYSA-N 0.000 claims 1
- GHDASPWTMZTSGF-UHFFFAOYSA-N n-[5-(6,7-dihydro-5h-pyrrolo[3,4-b]pyridin-4-ylsulfanyl)-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=4CNCC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 GHDASPWTMZTSGF-UHFFFAOYSA-N 0.000 claims 1
- SNQYTJSIASQNTP-UHFFFAOYSA-N n-[5-(isoquinolin-1-ylmethylsulfanyl)-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SCC=3C4=CC=CC=C4C=CN=3)=CN=2)OC=2C=CC=CC=2)=N1 SNQYTJSIASQNTP-UHFFFAOYSA-N 0.000 claims 1
- IVDJDVXMPBILES-UHFFFAOYSA-N n-[5-[(2-chlorophenyl)methylsulfanyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SCC=3C(=CC=CC=3)Cl)=CN=2)OC=2C=CC=CC=2)=N1 IVDJDVXMPBILES-UHFFFAOYSA-N 0.000 claims 1
- XCRQDDAPGANNBE-UHFFFAOYSA-N n-[5-[(2-fluorophenyl)methylsulfanyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SCC=3C(=CC=CC=3)F)=CN=2)OC=2C=CC=CC=2)=N1 XCRQDDAPGANNBE-UHFFFAOYSA-N 0.000 claims 1
- JIVDJANMUTYWLW-UHFFFAOYSA-N n-[5-[(2-methoxyphenyl)methylsulfanyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound COC1=CC=CC=C1CSC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 JIVDJANMUTYWLW-UHFFFAOYSA-N 0.000 claims 1
- OHVVSYZARBYMRA-UHFFFAOYSA-N n-[5-[(3,5-dimethyl-1,2-oxazol-4-yl)methylsulfanyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SCC3=C(ON=C3C)C)=CN=2)OC=2C=CC=CC=2)=N1 OHVVSYZARBYMRA-UHFFFAOYSA-N 0.000 claims 1
- BECUPDFQJCCYEG-UHFFFAOYSA-N n-[5-[(3,5-dimethyl-[1,2]oxazolo[4,5-b]pyridin-7-yl)sulfanyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC=3C=4ON=C(C)C=4N=C(C)C=3)=CN=2)OC=2C=CC=CC=2)=N1 BECUPDFQJCCYEG-UHFFFAOYSA-N 0.000 claims 1
- VRWUTDJAPNPVKG-UHFFFAOYSA-N n-[5-[(3-chloropyridin-2-yl)-piperidin-4-ylmethyl]sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SC(C3CCNCC3)C=3C(=CC=CN=3)Cl)=CN=2)OC=2C=CC=CC=2)=N1 VRWUTDJAPNPVKG-UHFFFAOYSA-N 0.000 claims 1
- TXJZTEFGLWXOJQ-UHFFFAOYSA-N n-[5-[(3-methoxyphenyl)methylsulfanyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound COC1=CC=CC(CSC=2C=C(OC=3C=CC=CC=3)C(NC=3SC=C(C)N=3)=NC=2)=C1 TXJZTEFGLWXOJQ-UHFFFAOYSA-N 0.000 claims 1
- FGBBPDOXRBWSIZ-UHFFFAOYSA-N n-[5-[(3-methoxypyridin-2-yl)methylsulfanyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound COC1=CC=CN=C1CSC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 FGBBPDOXRBWSIZ-UHFFFAOYSA-N 0.000 claims 1
- ZUOLLPZBDIDEMS-UHFFFAOYSA-N n-[5-[(3-methyl-[1,2]oxazolo[5,4-b]pyridin-4-yl)sulfanyl]-3-phenoxypyridin-2-yl]-4-(1-methylpiperidin-4-yl)-1,3-thiazol-2-amine Chemical compound C1CN(C)CCC1C1=CSC(NC=2C(=CC(SC=3C=4C(C)=NOC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 ZUOLLPZBDIDEMS-UHFFFAOYSA-N 0.000 claims 1
- RDOLRZPBTJEJRQ-UHFFFAOYSA-N n-[5-[(4-methoxyphenyl)methylsulfanyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1=CC(OC)=CC=C1CSC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 RDOLRZPBTJEJRQ-UHFFFAOYSA-N 0.000 claims 1
- DKLCSEKVDZCTED-UHFFFAOYSA-N n-[5-[(5-chloro-1,2,4-thiadiazol-3-yl)methylsulfanyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SCC=3N=C(Cl)SN=3)=CN=2)OC=2C=CC=CC=2)=N1 DKLCSEKVDZCTED-UHFFFAOYSA-N 0.000 claims 1
- BNHQVIYMMWNLIW-UHFFFAOYSA-N n-[5-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methylsulfanyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SCC=3SC(=NN=3)C3CC3)=CN=2)OC=2C=CC=CC=2)=N1 BNHQVIYMMWNLIW-UHFFFAOYSA-N 0.000 claims 1
- RBCUNDUEOBCJDW-UHFFFAOYSA-N n-[5-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methylsulfanyl]-3-phenylsulfanylpyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(SCC=3SC(=NN=3)C3CC3)=CN=2)SC=2C=CC=CC=2)=N1 RBCUNDUEOBCJDW-UHFFFAOYSA-N 0.000 claims 1
- IPHZQWSWHWRMHW-UHFFFAOYSA-N n-[5-[1-[2-(dimethylamino)ethyl]tetrazol-5-yl]sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CN(C)CCN1N=NN=C1SC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 IPHZQWSWHWRMHW-UHFFFAOYSA-N 0.000 claims 1
- GWISANUPAJYEND-UHFFFAOYSA-N n-[5-[2-(methoxymethyl)pyrimidin-4-yl]sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound COCC1=NC=CC(SC=2C=C(OC=3C=CC=CC=3)C(NC=3SC=C(C)N=3)=NC=2)=N1 GWISANUPAJYEND-UHFFFAOYSA-N 0.000 claims 1
- RWIKJGIOGACCPV-UHFFFAOYSA-N n-[5-[3-(dimethylamino)-1-phenylpropyl]sulfanyl-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1C(CCN(C)C)SC(C=C1OC=2C=CC=CC=2)=CN=C1NC1=NC(C)=CS1 RWIKJGIOGACCPV-UHFFFAOYSA-N 0.000 claims 1
- GCSSOQMRJSGLFE-UHFFFAOYSA-N n-[5-[3-(dimethylamino)propylsulfanyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1OC1=CC(SCCCN(C)C)=CN=C1NC1=NC(C)=CS1 GCSSOQMRJSGLFE-UHFFFAOYSA-N 0.000 claims 1
- YMKUEUUCLUUIPQ-UHFFFAOYSA-N n-[5-[4-(dimethylamino)but-1-enyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1OC1=CC(C=CCCN(C)C)=CN=C1NC1=NC(C)=CS1 YMKUEUUCLUUIPQ-UHFFFAOYSA-N 0.000 claims 1
- WJRWOFUOKMLRMP-UHFFFAOYSA-N n-[5-[4-(dimethylamino)butyl]-3-phenoxypyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1OC1=CC(CCCCN(C)C)=CN=C1NC1=NC(C)=CS1 WJRWOFUOKMLRMP-UHFFFAOYSA-N 0.000 claims 1
- JEMIOSINFIJAFF-UHFFFAOYSA-N n-[5-bromo-3-(4-fluorophenoxy)pyrazin-2-yl]-3-methyl-1,2,4-thiadiazol-5-amine Chemical compound CC1=NSC(NC=2C(=NC(Br)=CN=2)OC=2C=CC(F)=CC=2)=N1 JEMIOSINFIJAFF-UHFFFAOYSA-N 0.000 claims 1
- MZPGVLUNZRTVBX-UHFFFAOYSA-N n-[5-bromo-3-(4-fluorophenoxy)pyridin-2-yl]-3-(2-methylpropyl)-1,2,4-thiadiazol-5-amine Chemical compound CC(C)CC1=NSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC(F)=CC=2)=N1 MZPGVLUNZRTVBX-UHFFFAOYSA-N 0.000 claims 1
- RFTYVXRMZAKYKN-UHFFFAOYSA-N n-[5-bromo-3-(4-fluorophenoxy)pyridin-2-yl]-3-methyl-1,2,4-thiadiazol-5-amine Chemical compound CC1=NSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC(F)=CC=2)=N1 RFTYVXRMZAKYKN-UHFFFAOYSA-N 0.000 claims 1
- VNISZGHWLHEYTM-UHFFFAOYSA-N n-[5-bromo-3-(4-fluorophenoxy)pyridin-2-yl]-4-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound C1=CC(F)=CC=C1OC1=CC(Br)=CN=C1NC1=NC(CCC=2C=CC=CC=2)=CS1 VNISZGHWLHEYTM-UHFFFAOYSA-N 0.000 claims 1
- WETQJZMTBPNLTP-UHFFFAOYSA-N n-[5-bromo-3-(4-fluorophenoxy)pyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1=CC(F)=CC=C1OC1=CC(Br)=CN=C1NC1=NC2=CC=CN=C2S1 WETQJZMTBPNLTP-UHFFFAOYSA-N 0.000 claims 1
- WXMKYNVFKCXIHQ-UHFFFAOYSA-N n-[5-bromo-3-(4-fluorophenyl)sulfanylpyridin-2-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(NC=2C(=CC(Br)=CN=2)SC=2C=CC(F)=CC=2)=N1 WXMKYNVFKCXIHQ-UHFFFAOYSA-N 0.000 claims 1
- UUWQBYZKCFBNHE-UHFFFAOYSA-N n-[5-bromo-3-(4-fluorophenyl)sulfanylpyridin-2-yl]-[1,3]thiazolo[5,4-b]pyridin-2-amine Chemical compound C1=CC(F)=CC=C1SC1=CC(Br)=CN=C1NC1=NC2=CC=CN=C2S1 UUWQBYZKCFBNHE-UHFFFAOYSA-N 0.000 claims 1
- USQOSZSONRBGLF-UHFFFAOYSA-N n-[5-bromo-3-[4-(trifluoromethyl)phenoxy]pyridin-2-yl]-3-(oxolan-2-yl)-1,2,4-thiadiazol-5-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1=CC(Br)=CN=C1NC1=NC(C2OCCC2)=NS1 USQOSZSONRBGLF-UHFFFAOYSA-N 0.000 claims 1
- KIPUKPUCEMNQHT-UHFFFAOYSA-N n-[[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]methyl]-5-methyl-1,3,4-oxadiazol-2-amine Chemical compound O1C(C)=NN=C1NCC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 KIPUKPUCEMNQHT-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- SVURVNFOMHSDJS-UHFFFAOYSA-N tert-butyl 3-methyl-4-[2-[(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,3-thiazol-4-yl]piperidine-1-carboxylate Chemical compound CC1CN(C(=O)OC(C)(C)C)CCC1C1=CSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 SVURVNFOMHSDJS-UHFFFAOYSA-N 0.000 claims 1
- XLYVNNFTLWKAIG-UHFFFAOYSA-N tert-butyl 4-[5-[(3-phenoxy-5-pyridin-2-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NSC(NC=2C(=CC(SC=3N=CC=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 XLYVNNFTLWKAIG-UHFFFAOYSA-N 0.000 claims 1
- NEFUZTQATCGTKQ-UHFFFAOYSA-N tert-butyl 4-[5-[(3-phenoxy-5-thieno[3,2-b]pyridin-7-ylsulfanylpyridin-2-yl)amino]-1,2,4-thiadiazol-3-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NSC(NC=2C(=CC(SC=3C=4SC=CC=4N=CC=3)=CN=2)OC=2C=CC=CC=2)=N1 NEFUZTQATCGTKQ-UHFFFAOYSA-N 0.000 claims 1
- UMCKKHKRMANCHX-UHFFFAOYSA-N tert-butyl 4-[[2-[(5-bromo-3-phenoxypyridin-2-yl)amino]-1,3-thiazol-4-yl]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC=CC=2)=N1 UMCKKHKRMANCHX-UHFFFAOYSA-N 0.000 claims 1
- MOEXGHKXJXXWAR-UHFFFAOYSA-N tert-butyl 4-[[2-[[5-(3-methoxy-3-oxopropyl)sulfanyl-3-phenoxypyridin-2-yl]amino]-1,3-thiazol-4-yl]methyl]piperidine-1-carboxylate Chemical compound C=1C=CC=CC=1OC1=CC(SCCC(=O)OC)=CN=C1NC(SC=1)=NC=1CC1CCN(C(=O)OC(C)(C)C)CC1 MOEXGHKXJXXWAR-UHFFFAOYSA-N 0.000 claims 1
- ZAJCUPIAEIZAET-UHFFFAOYSA-N tert-butyl 4-[[2-[[5-bromo-3-(4-fluorophenoxy)pyridin-2-yl]amino]-1,3-thiazol-4-yl]methyl]-3-oxopiperazine-1-carboxylate Chemical compound O=C1CN(C(=O)OC(C)(C)C)CCN1CC1=CSC(NC=2C(=CC(Br)=CN=2)OC=2C=CC(F)=CC=2)=N1 ZAJCUPIAEIZAET-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract 2
- 206010012601 diabetes mellitus Diseases 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- KWNLASDDYJPRNX-UHFFFAOYSA-N CC(C)c1nc2cccnc2[s]1 Chemical compound CC(C)c1nc2cccnc2[s]1 KWNLASDDYJPRNX-UHFFFAOYSA-N 0.000 description 1
- 0 CIC(*=C)=C(N*)N=** Chemical compound CIC(*=C)=C(N*)N=** 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/12—Antidiarrhoeals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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| WO2008091770A1 (en) * | 2007-01-24 | 2008-07-31 | Array Biopharma Inc. | 2-aminopyridine derivatives as glucokinase activators |
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| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
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| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| JPWO2012121314A1 (ja) | 2011-03-09 | 2014-07-17 | 第一三共株式会社 | ジピリジルアミン誘導体 |
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| JP6177894B2 (ja) | 2012-05-18 | 2017-08-09 | アムジェン インコーポレイテッド | チアジアゾールの調製方法 |
| CN105164123A (zh) * | 2012-11-09 | 2015-12-16 | 安进股份有限公司 | (1s)-1-[5-({3-[(2-甲基吡啶-3-基)氧基]-5-(吡啶-2-基硫基)吡啶-2-基}氨基)-1,2,4-噻二唑-3-基]乙烷-1,2-二醇的结晶形式 |
| EP3421468B1 (en) | 2013-11-13 | 2020-11-04 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| WO2017093167A1 (en) | 2015-12-01 | 2017-06-08 | Basf Se | Pyridine compounds as fungicides |
| EP3383848B1 (en) | 2015-12-01 | 2020-01-08 | Basf Se | Pyridine compounds as fungicides |
| CN108329330B (zh) * | 2017-01-20 | 2021-05-04 | 复旦大学 | 2-苄氧苯基噁唑并吡啶类化合物及其药物用途 |
| CN110691776A (zh) | 2017-05-30 | 2020-01-14 | 巴斯夫欧洲公司 | 吡啶和吡嗪化合物 |
| GB201714777D0 (en) | 2017-09-14 | 2017-11-01 | Univ London Queen Mary | Agent |
| CN111372579B (zh) | 2017-10-30 | 2023-08-22 | 神经孔疗法股份有限公司 | 取代的苯基磺酰基苯基三唑硫酮和其用途 |
| EP3846793B1 (en) | 2018-09-07 | 2024-01-24 | PIC Therapeutics, Inc. | Eif4e inhibitors and uses thereof |
| AU2021230289A1 (en) | 2020-03-03 | 2022-09-29 | PIC Therapeutics, Inc. | eIF4E inhibitors and uses thereof |
| JP2024532276A (ja) | 2021-08-25 | 2024-09-05 | ピク セラピューティクス, インコーポレイテッド | eIF4E阻害剤及びその使用 |
| CA3229560A1 (en) | 2021-08-25 | 2023-03-02 | Christopher L. Vandeusen | Eif4e inhibitors and uses thereof |
Citations (2)
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| RU2125053C1 (ru) * | 1994-03-28 | 1999-01-20 | Ниссан Кемикал Индастриз Лтд. (JP | Соединение тиазолидина пиридинового типа или его соль, гипогликемическое средство, антигликационное средство и фармацевтическое средство, ингибирующее гипергликемию, неферментативную гликацию и альдозоредуктазу, для предупреждения и лечения сахарного диабета и диабетических осложнений |
| EP1598349A1 (en) * | 2003-02-13 | 2005-11-23 | Banyu Pharmaceutical Co., Ltd. | Novel 2-pyridinecarboxamide derivatives |
Family Cites Families (12)
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| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| NZ225999A (en) | 1987-09-10 | 1992-04-28 | Merck Sharp & Dohme | Azacyclic- or azabicyclic-substituted thiadiazole derivatives and pharmaceutical compositions |
| AU7193394A (en) | 1993-08-13 | 1995-03-14 | Zeneca Limited | Thia- and oxadiazole derivatives and their use as fungicides or insecticides |
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| HUP0202682A3 (en) * | 1999-09-10 | 2003-03-28 | Merck & Co Inc | Tyrosine kinase inhibitors, pharmaceutical compositions containing them and their use |
| JP2005511573A (ja) | 2001-11-02 | 2005-04-28 | グラクソ グループ リミテッド | Hcv阻害剤としての4−(5−員)−ヘテロアリールアシルピロリジン誘導体 |
| WO2003062224A1 (en) | 2002-01-17 | 2003-07-31 | Eli Lilly And Company | Aza-cyclic compounds as modulators of acetylcholine receptors |
| ES2289279T3 (es) * | 2002-03-15 | 2008-02-01 | Vertex Pharmaceuticals Incorporated | Composiciones utiles como inhibidores de proteinquinasas. |
| AR049418A1 (es) | 2004-02-27 | 2006-08-02 | Bayer Pharmaceuticals Corp | Derivados de heteroarilaminopirazol y composiciones farmaceuticas para el tratamiento de la diabetes. |
| EP1734040A4 (en) * | 2004-03-23 | 2007-11-28 | Banyu Pharma Co Ltd | SUBSTITUTED CHINAZOLINE OR PYRIDOPYRIMIDINE DERIVATIVE |
| WO2007058482A1 (en) * | 2005-11-16 | 2007-05-24 | Lg Life Sciences, Ltd. | Novel inhibitors of protein kinase |
| SI2013204T1 (sl) | 2006-03-24 | 2015-06-30 | Array Biopharma, Inc. | Analogi 2-aminopriridina kot aktivatorji glukokinaze |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2125053C1 (ru) * | 1994-03-28 | 1999-01-20 | Ниссан Кемикал Индастриз Лтд. (JP | Соединение тиазолидина пиридинового типа или его соль, гипогликемическое средство, антигликационное средство и фармацевтическое средство, ингибирующее гипергликемию, неферментативную гликацию и альдозоредуктазу, для предупреждения и лечения сахарного диабета и диабетических осложнений |
| EP1598349A1 (en) * | 2003-02-13 | 2005-11-23 | Banyu Pharmaceutical Co., Ltd. | Novel 2-pyridinecarboxamide derivatives |
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