JP2009507080A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009507080A5 JP2009507080A5 JP2008530213A JP2008530213A JP2009507080A5 JP 2009507080 A5 JP2009507080 A5 JP 2009507080A5 JP 2008530213 A JP2008530213 A JP 2008530213A JP 2008530213 A JP2008530213 A JP 2008530213A JP 2009507080 A5 JP2009507080 A5 JP 2009507080A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- triazole
- carbonyl
- optionally substituted
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 cyano, nitro, oxo, thioxo, trimethylsilanyl Chemical group 0.000 claims 187
- 125000000217 alkyl group Chemical group 0.000 claims 114
- 125000003710 aryl alkyl group Chemical group 0.000 claims 88
- 125000001188 haloalkyl group Chemical group 0.000 claims 80
- 125000005843 halogen group Chemical group 0.000 claims 79
- 229910052739 hydrogen Inorganic materials 0.000 claims 75
- 239000001257 hydrogen Substances 0.000 claims 75
- 125000001072 heteroaryl group Chemical group 0.000 claims 73
- 125000001424 substituent group Chemical group 0.000 claims 71
- 125000003118 aryl group Chemical group 0.000 claims 59
- 125000000623 heterocyclic group Chemical group 0.000 claims 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims 52
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 49
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 46
- 150000002431 hydrogen Chemical class 0.000 claims 46
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 42
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 29
- 125000004450 alkenylene group Chemical group 0.000 claims 28
- 125000002947 alkylene group Chemical group 0.000 claims 28
- 125000003107 substituted aryl group Chemical group 0.000 claims 23
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
- 125000003342 alkenyl group Chemical group 0.000 claims 21
- 125000000304 alkynyl group Chemical group 0.000 claims 21
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 21
- 125000000262 haloalkenyl group Chemical group 0.000 claims 21
- 125000000232 haloalkynyl group Chemical group 0.000 claims 21
- 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 21
- 125000004043 oxo group Chemical group O=* 0.000 claims 19
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 17
- 229910052757 nitrogen Inorganic materials 0.000 claims 15
- 125000004419 alkynylene group Chemical group 0.000 claims 14
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 14
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 12
- XTMRUJFITBKHKF-UHFFFAOYSA-N O=C=C1NC=NN1 Chemical compound O=C=C1NC=NN1 XTMRUJFITBKHKF-UHFFFAOYSA-N 0.000 claims 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 7
- NHAZGSRLKBTDBF-UHFFFAOYSA-N 1,2,4-triazol-1-amine Chemical compound NN1C=NC=N1 NHAZGSRLKBTDBF-UHFFFAOYSA-N 0.000 claims 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- ZORDVGLUJGYQHC-UHFFFAOYSA-N (3-amino-1,2,4-triazol-1-yl)-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2N=C(N)N=C2)=C1 ZORDVGLUJGYQHC-UHFFFAOYSA-N 0.000 claims 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- HPTBXUZCYQBJJP-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-isocyanato-1,2,4-triazole Chemical compound C(=O)=NN1N=C(N=C1)C1=CC2=C(OCCO2)C=C1 HPTBXUZCYQBJJP-UHFFFAOYSA-N 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- UAJVBJHJSGNUDP-UHFFFAOYSA-N O=C=C1NNC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 Chemical compound O=C=C1NNC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 UAJVBJHJSGNUDP-UHFFFAOYSA-N 0.000 claims 2
- DUNODFUDHXGRMR-UHFFFAOYSA-N O=C=C1NNC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 Chemical compound O=C=C1NNC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 DUNODFUDHXGRMR-UHFFFAOYSA-N 0.000 claims 2
- QTHWVDYFXXHCKO-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 QTHWVDYFXXHCKO-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 2
- QGIAQCGAUXRCQN-UHFFFAOYSA-N (2-chlorophenyl)-[2,5-diamino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3H-1,2,4-triazol-1-yl]methanone Chemical compound NC1=NC(N(N1C(=O)C1=C(C=CC=C1)Cl)N)C1=CC2=C(OCCO2)C=C1 QGIAQCGAUXRCQN-UHFFFAOYSA-N 0.000 claims 1
- UMZSCTIOTGRPNG-UHFFFAOYSA-N (3-chlorophenyl)-[2,5-diamino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3H-1,2,4-triazol-1-yl]methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC(=CC=C1)Cl)N)C1=CC2=C(OCCO2)C=C1 UMZSCTIOTGRPNG-UHFFFAOYSA-N 0.000 claims 1
- PNZPNYODHVFLRC-UHFFFAOYSA-N (4-chlorophenyl)-[2,5-diamino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3H-1,2,4-triazol-1-yl]methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC=C(C=C1)Cl)N)C1=CC2=C(OCCO2)C=C1 PNZPNYODHVFLRC-UHFFFAOYSA-N 0.000 claims 1
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims 1
- NRFGIUAJIAWVSM-UHFFFAOYSA-N 1-[2-[4-[[5-amino-1-(3-morpholin-4-ylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]ethyl]pyrrolidin-2-one Chemical compound N=1N(C(=O)C=2C=C(C=CC=2)N2CCOCC2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1=O NRFGIUAJIAWVSM-UHFFFAOYSA-N 0.000 claims 1
- IHMXXMVGQXHFTN-UHFFFAOYSA-N 1-[2-[4-[[5-amino-1-(4-morpholin-4-ylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]ethyl]pyrrolidin-2-one Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)N2CCOCC2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1=O IHMXXMVGQXHFTN-UHFFFAOYSA-N 0.000 claims 1
- XCPODFGJDNBJIR-UHFFFAOYSA-N 1-[2-[4-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]ethyl]pyrrolidin-2-one Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3C(CCC3)=O)=CC=2)=N1 XCPODFGJDNBJIR-UHFFFAOYSA-N 0.000 claims 1
- STPJYJRCCBVRDB-UHFFFAOYSA-N 1-[2-[4-[[5-amino-1-[4-(thiadiazol-4-yl)benzoyl]-1,2,4-triazol-3-yl]amino]phenoxy]ethyl]pyrrolidin-2-one Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)C=2N=NSC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1=O STPJYJRCCBVRDB-UHFFFAOYSA-N 0.000 claims 1
- QCLROQCLVYUOBI-UHFFFAOYSA-N 1-[2-[4-[[5-amino-1-[4-[(2-methylpropan-2-yl)oxy]benzoyl]-1,2,4-triazol-3-yl]amino]phenoxy]ethyl]pyrrolidin-2-one Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3C(CCC3)=O)=CC=2)=N1 QCLROQCLVYUOBI-UHFFFAOYSA-N 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- DXMODMWMLNYQAH-UHFFFAOYSA-N 2-[3-[[5-amino-1-(2-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetonitrile Chemical compound CC1=CC=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OCC#N)C=CC=2)=N1 DXMODMWMLNYQAH-UHFFFAOYSA-N 0.000 claims 1
- RIXUNLLOBWWNHG-UHFFFAOYSA-N 2-[3-[[5-amino-1-(3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]-n-cyclohexylacetamide Chemical compound CC1=CC=CC(C(=O)N2C(=NC(NC=3C=C(OCC(=O)NC4CCCCC4)C=CC=3)=N2)N)=C1 RIXUNLLOBWWNHG-UHFFFAOYSA-N 0.000 claims 1
- XJRWFNSWOOWKFM-UHFFFAOYSA-N 2-[3-[[5-amino-1-(3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]-n-methylacetamide Chemical compound CNC(=O)COC1=CC=CC(NC2=NN(C(N)=N2)C(=O)C=2C=C(C)C=CC=2)=C1 XJRWFNSWOOWKFM-UHFFFAOYSA-N 0.000 claims 1
- VSUSEMIMJXCYLF-UHFFFAOYSA-N 2-[3-[[5-amino-1-(3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetonitrile Chemical compound CC1=CC=CC(C(=O)N2C(=NC(NC=3C=C(OCC#N)C=CC=3)=N2)N)=C1 VSUSEMIMJXCYLF-UHFFFAOYSA-N 0.000 claims 1
- GIADVRXJCAKMTN-UHFFFAOYSA-N 2-[3-[[5-amino-1-(4-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetonitrile Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OCC#N)C=CC=2)=N1 GIADVRXJCAKMTN-UHFFFAOYSA-N 0.000 claims 1
- HRDAREHLSSSHBT-UHFFFAOYSA-N 2-[3-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetonitrile Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OCC#N)C=CC=2)=N1 HRDAREHLSSSHBT-UHFFFAOYSA-N 0.000 claims 1
- KTQVEJGFDVZXDD-UHFFFAOYSA-N 2-[3-[[5-amino-2-(3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]-n-cyclohexylacetamide Chemical compound CC1=CC=CC(C(=O)N2C(=NC(N)=N2)NC=2C=C(OCC(=O)NC3CCCCC3)C=CC=2)=C1 KTQVEJGFDVZXDD-UHFFFAOYSA-N 0.000 claims 1
- NCJZUMFNIHRNPJ-UHFFFAOYSA-N 2-[4-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetonitrile Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCC#N)=CC=2)=N1 NCJZUMFNIHRNPJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- VZOUJKBRNNSEGL-UHFFFAOYSA-N 3-[[5-amino-1-(1h-indole-6-carbonyl)-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=C2C=CNC2=CC(C(=O)N2C(N)=NC(=N2)NC2C3CC(C=C3)C2C(=O)N)=C1 VZOUJKBRNNSEGL-UHFFFAOYSA-N 0.000 claims 1
- SZCMEIUZIVDZKU-UHFFFAOYSA-N 3-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC2C(C3CC2C=C3)C(N)=O)=N1 SZCMEIUZIVDZKU-UHFFFAOYSA-N 0.000 claims 1
- OQQWRMVCEJFSBE-UHFFFAOYSA-N 3-[[5-amino-1-[3-(dimethylamino)benzoyl]-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CN(C)C1=CC=CC(C(=O)N2C(=NC(NC3C(C4CC3C=C4)C(N)=O)=N2)N)=C1 OQQWRMVCEJFSBE-UHFFFAOYSA-N 0.000 claims 1
- GRZCEOUYNCPZJG-UHFFFAOYSA-N 3-[[5-amino-1-[4-(dimethylamino)benzoyl]-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(N)=NC(NC2C(C3CC2C=C3)C(N)=O)=N1 GRZCEOUYNCPZJG-UHFFFAOYSA-N 0.000 claims 1
- CYXNUEGTPOTDHD-UHFFFAOYSA-N 3-[[5-amino-2-(1h-indole-6-carbonyl)-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=C2C=CNC2=CC(C(=O)N2N=C(N)N=C2NC2C3CC(C=C3)C2C(=O)N)=C1 CYXNUEGTPOTDHD-UHFFFAOYSA-N 0.000 claims 1
- NOHPLIRXGAGHEQ-UHFFFAOYSA-N 3-[[5-amino-2-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(NC2C(C3CC2C=C3)C(N)=O)=NC(N)=N1 NOHPLIRXGAGHEQ-UHFFFAOYSA-N 0.000 claims 1
- BTNRXORWAUSFNH-UHFFFAOYSA-N 3-[[5-amino-2-[3-(dimethylamino)benzoyl]-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CN(C)C1=CC=CC(C(=O)N2C(=NC(N)=N2)NC2C(C3CC2C=C3)C(N)=O)=C1 BTNRXORWAUSFNH-UHFFFAOYSA-N 0.000 claims 1
- MKKKMNSNNKBPNA-UHFFFAOYSA-N 3-[[5-amino-2-[4-(dimethylamino)benzoyl]-1,2,4-triazol-3-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(NC2C(C3CC2C=C3)C(N)=O)=NC(N)=N1 MKKKMNSNNKBPNA-UHFFFAOYSA-N 0.000 claims 1
- FHHQLWMLTNNLPW-UHFFFAOYSA-N 3-amino-n-(1,3-benzodioxol-5-yl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C=1C=C2OCOC2=CC=1NC(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCCC1 FHHQLWMLTNNLPW-UHFFFAOYSA-N 0.000 claims 1
- XPWWFEIYDZXDGX-UHFFFAOYSA-N 3-amino-n-(3,5-dimethoxyphenyl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound COC1=CC(OC)=CC(NC(=O)N2C(=NC(N)=N2)NC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 XPWWFEIYDZXDGX-UHFFFAOYSA-N 0.000 claims 1
- PAKVXTXEMKZLGR-UHFFFAOYSA-N 3-amino-n-(3-methylphenyl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2C(=NC(N)=N2)NC=2C=CC(OCCN3CCCCC3)=CC=2)=C1 PAKVXTXEMKZLGR-UHFFFAOYSA-N 0.000 claims 1
- QEOMQUZNUXBEDX-UHFFFAOYSA-N 3-amino-n-(4-butoxyphenyl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1NC(=O)N1C(NC=2C=CC(OCCN3CCCCC3)=CC=2)=NC(N)=N1 QEOMQUZNUXBEDX-UHFFFAOYSA-N 0.000 claims 1
- RZUJWQSMYGJDRX-UHFFFAOYSA-N 3-amino-n-(4-methoxyphenyl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)N1C(NC=2C=CC(OCCN3CCCCC3)=CC=2)=NC(N)=N1 RZUJWQSMYGJDRX-UHFFFAOYSA-N 0.000 claims 1
- PNBMCFSJJPCLTP-UHFFFAOYSA-N 3-amino-n-(4-methylphenyl)-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(C)=CC=C1NC(=O)N1C(NC=2C=CC(OCCN3CCCCC3)=CC=2)=NC(N)=N1 PNBMCFSJJPCLTP-UHFFFAOYSA-N 0.000 claims 1
- NBXVLSOIHGPLCB-UHFFFAOYSA-N 3-amino-n-cyclohexyl-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1CCCCC1NC(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCCC1 NBXVLSOIHGPLCB-UHFFFAOYSA-N 0.000 claims 1
- YPQKZFJFBDPWCW-UHFFFAOYSA-N 3-amino-n-cyclopentyl-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1CCCC1NC(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCCC1 YPQKZFJFBDPWCW-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- IQSMMJOQMRCYDT-UHFFFAOYSA-N 4-[5-amino-3-(4-morpholin-4-ylanilino)-1,2,4-triazole-1-carbonyl]benzenesulfonamide Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)S(N)(=O)=O)C(N)=NC=1NC(C=C1)=CC=C1N1CCOCC1 IQSMMJOQMRCYDT-UHFFFAOYSA-N 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- QUSPJWAWDJCOCQ-UHFFFAOYSA-N 5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-n-(4-propan-2-ylphenyl)-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 QUSPJWAWDJCOCQ-UHFFFAOYSA-N 0.000 claims 1
- BTOYEEBQOWRPRR-UHFFFAOYSA-N 5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-n-(2,4,6-trifluorophenyl)-1,2,4-triazole-1-carbothioamide Chemical compound N=1N(C(=S)NC=2C(=CC(F)=CC=2F)F)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 BTOYEEBQOWRPRR-UHFFFAOYSA-N 0.000 claims 1
- NIGJHYOSJINNKT-UHFFFAOYSA-N 5-amino-n-(1,3-benzodioxol-5-yl)-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound N=1N(C(=O)NC=2C=C3OCOC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCCC1 NIGJHYOSJINNKT-UHFFFAOYSA-N 0.000 claims 1
- OCJLUGBCXCZFLO-UHFFFAOYSA-N 5-amino-n-(1,3-benzodioxol-5-yl)-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound N=1N(C(=O)NC=2C=C3OCOC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 OCJLUGBCXCZFLO-UHFFFAOYSA-N 0.000 claims 1
- FAIQUQZLHCFIGZ-UHFFFAOYSA-N 5-amino-n-(2,6-difluorophenyl)-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carbothioamide Chemical compound N=1N(C(=S)NC=2C(=CC=CC=2F)F)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 FAIQUQZLHCFIGZ-UHFFFAOYSA-N 0.000 claims 1
- CGSXLCRJRJCZQF-UHFFFAOYSA-N 5-amino-n-(3-methoxyphenyl)-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound COC1=CC=CC(NC(=O)N2C(=NC(NC=3C=CC(OCCN4CCCC4)=CC=3)=N2)N)=C1 CGSXLCRJRJCZQF-UHFFFAOYSA-N 0.000 claims 1
- FETOGIDRJAFSQY-UHFFFAOYSA-N 5-amino-n-(3-methylphenyl)-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2C(=NC(NC=3C=CC(OCCN4CCCCC4)=CC=3)=N2)N)=C1 FETOGIDRJAFSQY-UHFFFAOYSA-N 0.000 claims 1
- VYFBEISNIGMDGI-UHFFFAOYSA-N 5-amino-n-(3-methylphenyl)-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2C(=NC(NC=3C=CC(OCCN4CCCC4)=CC=3)=N2)N)=C1 VYFBEISNIGMDGI-UHFFFAOYSA-N 0.000 claims 1
- PTRXCAWWXXDVNF-UHFFFAOYSA-N 5-amino-n-(4-butoxyphenyl)-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1NC(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 PTRXCAWWXXDVNF-UHFFFAOYSA-N 0.000 claims 1
- CWVPBBILDVOUCB-UHFFFAOYSA-N 5-amino-n-(4-chlorophenyl)-3-(4-methoxyanilino)-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(OC)=CC=C1NC1=NN(C(=O)NC=2C=CC(Cl)=CC=2)C(N)=N1 CWVPBBILDVOUCB-UHFFFAOYSA-N 0.000 claims 1
- VIHVYWMMMNIANY-UHFFFAOYSA-N 5-amino-n-(4-cyanophenyl)-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound N=1N(C(=O)NC=2C=CC(=CC=2)C#N)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCCC1 VIHVYWMMMNIANY-UHFFFAOYSA-N 0.000 claims 1
- MEUIOPYIZCSGQF-UHFFFAOYSA-N 5-amino-n-(4-methoxyphenyl)-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 MEUIOPYIZCSGQF-UHFFFAOYSA-N 0.000 claims 1
- MMSDOUWVYRMHLJ-UHFFFAOYSA-N 5-amino-n-(4-methylphenyl)-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(C)=CC=C1NC(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 MMSDOUWVYRMHLJ-UHFFFAOYSA-N 0.000 claims 1
- UGVPDLRHCWVEJW-UHFFFAOYSA-N 5-amino-n-(4-methylphenyl)-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(C)=CC=C1NC(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 UGVPDLRHCWVEJW-UHFFFAOYSA-N 0.000 claims 1
- QYCOLLKOCUDRML-UHFFFAOYSA-N 5-amino-n-[4-(dimethylamino)phenyl]-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 QYCOLLKOCUDRML-UHFFFAOYSA-N 0.000 claims 1
- MLJXZBSCALPVLI-UHFFFAOYSA-N 5-amino-n-cyclohexyl-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound N=1N(C(=O)NC2CCCCC2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCCC1 MLJXZBSCALPVLI-UHFFFAOYSA-N 0.000 claims 1
- PORXTZDLWYFDLW-UHFFFAOYSA-N 5-amino-n-cyclopentyl-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound N=1N(C(=O)NC2CCCC2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCCC1 PORXTZDLWYFDLW-UHFFFAOYSA-N 0.000 claims 1
- OVRQYZBJLHHTOZ-UHFFFAOYSA-N 6-[5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carbonyl]-2,2-dimethyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C2NC(=O)C(C)(C)OC2=CC=C1C(=O)N(C(=N1)N)N=C1NC(C=C1)=CC=C1OCCN1CCCCC1 OVRQYZBJLHHTOZ-UHFFFAOYSA-N 0.000 claims 1
- QHHRFPWWUKSBKP-UHFFFAOYSA-N 6-[5-amino-3-[4-[2-(dimethylamino)ethoxy]anilino]-1,2,4-triazole-1-carbonyl]-2,2-dimethyl-4h-1,4-benzoxazin-3-one Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NN(C(=O)C=2C=C3NC(=O)C(C)(C)OC3=CC=2)C(N)=N1 QHHRFPWWUKSBKP-UHFFFAOYSA-N 0.000 claims 1
- UJVKQVLKMIBWAH-UHFFFAOYSA-N 6-[5-amino-3-[4-[2-(dimethylamino)propoxy]anilino]-1,2,4-triazole-1-carbonyl]-2,2-dimethyl-4h-1,4-benzoxazin-3-one Chemical compound C1=CC(OCC(C)N(C)C)=CC=C1NC1=NN(C(=O)C=2C=C3NC(=O)C(C)(C)OC3=CC=2)C(N)=N1 UJVKQVLKMIBWAH-UHFFFAOYSA-N 0.000 claims 1
- LHOUTXAZCFTRGH-UHFFFAOYSA-N [2,3-diamino-5-[3-[4-(2-chloro-6-fluorophenyl)piperazin-1-yl]propyl]-3h-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C(=NC(N)N2N)CCCN2CCN(CC2)C=2C(=CC=CC=2F)Cl)=C1 LHOUTXAZCFTRGH-UHFFFAOYSA-N 0.000 claims 1
- CQOUVRUJIPXIEZ-UHFFFAOYSA-N [2,5-diamino-3-(1,3-benzothiazol-2-yl)-3H-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC(=CC=C1)C)N)C=1SC2=C(N=1)C=CC=C2 CQOUVRUJIPXIEZ-UHFFFAOYSA-N 0.000 claims 1
- URKOBTDLSZYYOP-UHFFFAOYSA-N [2,5-diamino-3-(1,3-benzothiazol-6-yl)-3H-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC(=CC=C1)C)N)C1=CC2=C(N=CS2)C=C1 URKOBTDLSZYYOP-UHFFFAOYSA-N 0.000 claims 1
- YBWFKUVYTRUFIJ-UHFFFAOYSA-N [2,5-diamino-3-(1-benzofuran-5-yl)-3H-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC(=CC=C1)C)N)C=1C=CC2=C(C=CO2)C=1 YBWFKUVYTRUFIJ-UHFFFAOYSA-N 0.000 claims 1
- DEQPSUYLJXDODD-UHFFFAOYSA-N [2,5-diamino-3-(1-methylsulfonylpiperidin-4-yl)-3h-1,2,4-triazol-1-yl]-(2,6-difluorophenyl)methanone Chemical compound C1CN(S(=O)(=O)C)CCC1C1N(N)N(C(=O)C=2C(=CC=CC=2F)F)C(N)=N1 DEQPSUYLJXDODD-UHFFFAOYSA-N 0.000 claims 1
- FUAOVWRLKMLUTP-UHFFFAOYSA-N [2,5-diamino-3-(1-methylsulfonylpiperidin-4-yl)-3h-1,2,4-triazol-1-yl]-(4-morpholin-4-ylphenyl)methanone Chemical compound C1CN(S(=O)(=O)C)CCC1C1N(N)N(C(=O)C=2C=CC(=CC=2)N2CCOCC2)C(N)=N1 FUAOVWRLKMLUTP-UHFFFAOYSA-N 0.000 claims 1
- MWMNIKBCPLJPIN-UHFFFAOYSA-N [2,5-diamino-3-(1-methylsulfonylpiperidin-4-yl)-3h-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(C2CCN(CC2)S(C)(=O)=O)N1N MWMNIKBCPLJPIN-UHFFFAOYSA-N 0.000 claims 1
- XYIABQLOZPMVGT-UHFFFAOYSA-N [2,5-diamino-3-(1-methylsulfonylpiperidin-4-yl)-3h-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(C2CCN(CC2)S(C)(=O)=O)N1N XYIABQLOZPMVGT-UHFFFAOYSA-N 0.000 claims 1
- XMFZDWKBRWTQLW-UHFFFAOYSA-N [2,5-diamino-3-(1H-indazol-5-yl)-3H-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC(=CC=C1)C)N)C=1C=C2C=NNC2=CC=1 XMFZDWKBRWTQLW-UHFFFAOYSA-N 0.000 claims 1
- SSIHETFPKVFYTK-UHFFFAOYSA-N [2,5-diamino-3-(1H-indazol-6-yl)-3H-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC(=CC=C1)C)N)C1=CC=C2C=NNC2=C1 SSIHETFPKVFYTK-UHFFFAOYSA-N 0.000 claims 1
- SAWYAVDLNYURHI-UHFFFAOYSA-N [2,5-diamino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3H-1,2,4-triazol-1-yl]-(3,4-dimethylphenyl)methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC(=C(C=C1)C)C)N)C1=CC2=C(OCCO2)C=C1 SAWYAVDLNYURHI-UHFFFAOYSA-N 0.000 claims 1
- WUMLFCZJZXBPBL-UHFFFAOYSA-N [2,5-diamino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3H-1,2,4-triazol-1-yl]-(3-ethoxyphenyl)methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC(=CC=C1)OCC)N)C1=CC2=C(OCCO2)C=C1 WUMLFCZJZXBPBL-UHFFFAOYSA-N 0.000 claims 1
- NBEVFTZMUZNICA-UHFFFAOYSA-N [2,5-diamino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3h-1,2,4-triazol-1-yl]-(3-hydroxyphenyl)methanone Chemical compound NN1C(C=2C=C3OCCOC3=CC=2)N=C(N)N1C(=O)C1=CC=CC(O)=C1 NBEVFTZMUZNICA-UHFFFAOYSA-N 0.000 claims 1
- QJVSUXGQKZYQGM-UHFFFAOYSA-N [2,5-diamino-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3h-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(C=2C=C3OCCOC3=CC=2)N1N QJVSUXGQKZYQGM-UHFFFAOYSA-N 0.000 claims 1
- XRELMNGFVBNAPA-UHFFFAOYSA-N [2,5-diamino-3-(2-methylindazol-5-yl)-3h-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C(=NC(N2N)C2=CC3=CN(C)N=C3C=C2)N)=C1 XRELMNGFVBNAPA-UHFFFAOYSA-N 0.000 claims 1
- HRZIILRJQYONQH-UHFFFAOYSA-N [2,5-diamino-3-[2-(methylaminomethyl)-1-benzofuran-5-yl]-3h-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound C=1C=C2OC(CNC)=CC2=CC=1C(N1N)N=C(N)N1C(=O)C1=CC=CC(C)=C1 HRZIILRJQYONQH-UHFFFAOYSA-N 0.000 claims 1
- BALMEHDCBFUISW-UHFFFAOYSA-N [2,5-diamino-3-[3-fluoro-4-(2-pyrrolidin-1-ylethoxy)phenyl]-3H-1,2,4-triazol-1-yl]-(4-morpholin-4-ylphenyl)methanone Chemical compound NC1=NC(N(N1C(=O)C1=CC=C(C=C1)N1CCOCC1)N)C1=CC(=C(C=C1)OCCN1CCCC1)F BALMEHDCBFUISW-UHFFFAOYSA-N 0.000 claims 1
- KJUDSXRBQYZOHP-UHFFFAOYSA-N [3-amino-5-(4-morpholin-4-ylanilino)-1,2,4-triazol-1-yl]-(3-chlorophenyl)methanone Chemical compound C=1C=CC(Cl)=CC=1C(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1N1CCOCC1 KJUDSXRBQYZOHP-UHFFFAOYSA-N 0.000 claims 1
- YAMHTOIRBNHPRV-UHFFFAOYSA-N [3-amino-5-(4-morpholin-4-ylanilino)-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(NC=2C=CC(=CC=2)N2CCOCC2)=NC(N)=N1 YAMHTOIRBNHPRV-UHFFFAOYSA-N 0.000 claims 1
- GSACMOLWQWNHHC-UHFFFAOYSA-N [3-amino-5-(4-piperidin-1-ylanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(NC=2C=CC(=CC=2)N2CCCCC2)=NC(N)=N1 GSACMOLWQWNHHC-UHFFFAOYSA-N 0.000 claims 1
- ARWILRUPFKEXIH-UHFFFAOYSA-N [3-amino-5-(4-propan-2-yloxyanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NC(N)=NN1C(=O)C1=CC=C(C)C=C1 ARWILRUPFKEXIH-UHFFFAOYSA-N 0.000 claims 1
- IGGDGWHKKRPYTG-UHFFFAOYSA-N [3-amino-5-(4-pyrrolidin-1-ylanilino)-1,2,4-triazol-1-yl]-(4-tert-butylphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)N1C(NC=2C=CC(=CC=2)N2CCCC2)=NC(N)=N1 IGGDGWHKKRPYTG-UHFFFAOYSA-N 0.000 claims 1
- YWUDFDCAHCLFLP-UHFFFAOYSA-N [3-amino-5-[3-fluoro-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-morpholin-4-ylphenyl)methanone Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)N1N=C(N)N=C1NC(C=C1F)=CC=C1OCCN1CCCC1 YWUDFDCAHCLFLP-UHFFFAOYSA-N 0.000 claims 1
- KACSJMQYPBBPAD-UHFFFAOYSA-N [3-amino-5-[4-(2-imidazol-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1-benzothiophen-5-yl)methanone Chemical compound C=1C=C2SC=CC2=CC=1C(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1C=CN=C1 KACSJMQYPBBPAD-UHFFFAOYSA-N 0.000 claims 1
- GOGVMCNWFRNLKH-UHFFFAOYSA-N [3-amino-5-[4-(2-imidazol-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1h-indol-6-yl)methanone Chemical compound C=1C=C2C=CNC2=CC=1C(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1C=CN=C1 GOGVMCNWFRNLKH-UHFFFAOYSA-N 0.000 claims 1
- GDOCQJQECKTDQF-UHFFFAOYSA-N [3-amino-5-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(NC=2C=CC(OCCN3CCCCC3)=CC=2)=NC(N)=N1 GDOCQJQECKTDQF-UHFFFAOYSA-N 0.000 claims 1
- HSYMYBLAGUXLNV-UHFFFAOYSA-N [3-amino-5-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1-benzothiophen-2-yl)methanone Chemical compound C=1C2=CC=CC=C2SC=1C(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCC1 HSYMYBLAGUXLNV-UHFFFAOYSA-N 0.000 claims 1
- HJZCNLFCOYPRAM-UHFFFAOYSA-N [3-amino-5-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1h-indol-5-yl)methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCC1 HJZCNLFCOYPRAM-UHFFFAOYSA-N 0.000 claims 1
- MNVTWSZOIHDXSQ-UHFFFAOYSA-N [3-amino-5-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(NC=2C=CC(OCCN3CCCC3)=CC=2)=NC(N)=N1 MNVTWSZOIHDXSQ-UHFFFAOYSA-N 0.000 claims 1
- SQVXTPGSUBDZOI-UHFFFAOYSA-N [3-amino-5-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-tert-butylphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)N1C(NC=2C=CC(OCCN3CCCC3)=CC=2)=NC(N)=N1 SQVXTPGSUBDZOI-UHFFFAOYSA-N 0.000 claims 1
- DOPLDBXCAMNGSL-KRWDZBQOSA-N [3-amino-5-[4-[2-[(3s)-3-fluoropyrrolidin-1-yl]ethoxy]anilino]-1,2,4-triazol-1-yl]-(1h-indol-6-yl)methanone Chemical compound C=1C=C2C=CNC2=CC=1C(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1CC[C@H](F)C1 DOPLDBXCAMNGSL-KRWDZBQOSA-N 0.000 claims 1
- FHABOEPEJLGKFW-INIZCTEOSA-N [3-amino-5-[4-[2-[(3s)-3-fluoropyrrolidin-1-yl]ethoxy]anilino]-1,2,4-triazol-1-yl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound C=1C=C2OCCOC2=CC=1C(=O)N1N=C(N)N=C1NC(C=C1)=CC=C1OCCN1CC[C@H](F)C1 FHABOEPEJLGKFW-INIZCTEOSA-N 0.000 claims 1
- ZOXXNISZCDJSHC-UHFFFAOYSA-N [5-amino-2-(methylamino)-3-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-3h-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound CNN1C(C=2C=CC(OCCN3CCCC3)=CC=2)N=C(N)N1C(=O)C1=CC=C(OC(C)(C)C)C=C1 ZOXXNISZCDJSHC-UHFFFAOYSA-N 0.000 claims 1
- OQPIXYBUHNAERJ-UHFFFAOYSA-N [5-amino-3-(2-fluoroanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C(=CC=CC=2)F)=N1 OQPIXYBUHNAERJ-UHFFFAOYSA-N 0.000 claims 1
- BFUDPBXLPDVIHJ-UHFFFAOYSA-N [5-amino-3-(2-hydroxyanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C(=CC=CC=2)O)=N1 BFUDPBXLPDVIHJ-UHFFFAOYSA-N 0.000 claims 1
- NUGLQFHGROHIHK-UHFFFAOYSA-N [5-amino-3-(2-methoxyanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound COC1=CC=CC=C1NC1=NN(C(=O)C=2C=CC(C)=CC=2)C(N)=N1 NUGLQFHGROHIHK-UHFFFAOYSA-N 0.000 claims 1
- PAVZHTWJNDMVJR-UHFFFAOYSA-N [5-amino-3-(2-methylanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C(=CC=CC=2)C)=N1 PAVZHTWJNDMVJR-UHFFFAOYSA-N 0.000 claims 1
- ZTMDOCGXWCVKFJ-UHFFFAOYSA-N [5-amino-3-(3,4-dihydro-2h-1,4-benzoxazin-6-ylamino)-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C(=NC(NC=3C=C4NCCOC4=CC=3)=N2)N)=C1 ZTMDOCGXWCVKFJ-UHFFFAOYSA-N 0.000 claims 1
- YROSLKRJRJJCGJ-UHFFFAOYSA-N [5-amino-3-(3-cyclopentyloxyanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OC3CCCC3)C=CC=2)=N1 YROSLKRJRJJCGJ-UHFFFAOYSA-N 0.000 claims 1
- RVTCPELFVGUGTQ-UHFFFAOYSA-N [5-amino-3-(3-ethoxyanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound CCOC1=CC=CC(NC2=NN(C(N)=N2)C(=O)C=2C=CC(OC(C)C)=CC=2)=C1 RVTCPELFVGUGTQ-UHFFFAOYSA-N 0.000 claims 1
- OEKSEYFYLJZANB-UHFFFAOYSA-N [5-amino-3-(3-fluoroanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(F)C=CC=2)=N1 OEKSEYFYLJZANB-UHFFFAOYSA-N 0.000 claims 1
- XWQXAZWAOANAOL-UHFFFAOYSA-N [5-amino-3-(3-hydroxyanilino)-1,2,4-triazol-1-yl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)N1C(N)=NC(NC=2C=C(O)C=CC=2)=N1 XWQXAZWAOANAOL-UHFFFAOYSA-N 0.000 claims 1
- SBAMECVUBCXTJJ-UHFFFAOYSA-N [5-amino-3-(3-hydroxyanilino)-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C(=NC(NC=3C=C(O)C=CC=3)=N2)N)=C1 SBAMECVUBCXTJJ-UHFFFAOYSA-N 0.000 claims 1
- NIEWTZVVVCBHRP-UHFFFAOYSA-N [5-amino-3-(3-hydroxyanilino)-1,2,4-triazol-1-yl]-(3-propan-2-yloxyphenyl)methanone Chemical compound CC(C)OC1=CC=CC(C(=O)N2C(=NC(NC=3C=C(O)C=CC=3)=N2)N)=C1 NIEWTZVVVCBHRP-UHFFFAOYSA-N 0.000 claims 1
- ZSPOTARGUFXWEP-UHFFFAOYSA-N [5-amino-3-(3-hydroxyanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(O)C=CC=2)=N1 ZSPOTARGUFXWEP-UHFFFAOYSA-N 0.000 claims 1
- NTOSOZWMONIQTO-UHFFFAOYSA-N [5-amino-3-(3-methoxyanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound COC1=CC=CC(NC2=NN(C(N)=N2)C(=O)C=2C=CC(C)=CC=2)=C1 NTOSOZWMONIQTO-UHFFFAOYSA-N 0.000 claims 1
- JTWWSMPKROFXHG-UHFFFAOYSA-N [5-amino-3-(3-methoxyanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound COC1=CC=CC(NC2=NN(C(N)=N2)C(=O)C=2C=CC(OC(C)C)=CC=2)=C1 JTWWSMPKROFXHG-UHFFFAOYSA-N 0.000 claims 1
- XSDWBHUBORHKIM-UHFFFAOYSA-N [5-amino-3-(3-methylanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(C)C=CC=2)=N1 XSDWBHUBORHKIM-UHFFFAOYSA-N 0.000 claims 1
- XXYFMLFSXBQDAL-UHFFFAOYSA-N [5-amino-3-(3-phenylmethoxyanilino)-1,2,4-triazol-1-yl]-(3-propan-2-yloxyphenyl)methanone Chemical compound CC(C)OC1=CC=CC(C(=O)N2C(=NC(NC=3C=C(OCC=4C=CC=CC=4)C=CC=3)=N2)N)=C1 XXYFMLFSXBQDAL-UHFFFAOYSA-N 0.000 claims 1
- IEADOYIUQKTHAN-UHFFFAOYSA-N [5-amino-3-(3-phenylmethoxyanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 IEADOYIUQKTHAN-UHFFFAOYSA-N 0.000 claims 1
- CTVFPODABLHDFW-UHFFFAOYSA-N [5-amino-3-(3-phenylmethoxyanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 CTVFPODABLHDFW-UHFFFAOYSA-N 0.000 claims 1
- ZCKMXMWHQPYTFB-UHFFFAOYSA-N [5-amino-3-(3-piperidin-1-ylanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(C=CC=2)N2CCCCC2)=N1 ZCKMXMWHQPYTFB-UHFFFAOYSA-N 0.000 claims 1
- KVHNGXZTVYSMKG-UHFFFAOYSA-N [5-amino-3-(3-propan-2-yloxyanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OC(C)C)C=CC=2)=N1 KVHNGXZTVYSMKG-UHFFFAOYSA-N 0.000 claims 1
- CRWTXAWSTOUBPY-UHFFFAOYSA-N [5-amino-3-(4-cyclopentyloxyanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OC3CCCC3)=CC=2)=N1 CRWTXAWSTOUBPY-UHFFFAOYSA-N 0.000 claims 1
- KTWKCWXRONAAME-UHFFFAOYSA-N [5-amino-3-(4-ethoxyanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OCC)=CC=C1NC1=NN(C(=O)C=2C=CC(OC(C)C)=CC=2)C(N)=N1 KTWKCWXRONAAME-UHFFFAOYSA-N 0.000 claims 1
- AFQXHTAGFYVRPW-UHFFFAOYSA-N [5-amino-3-(4-fluoroanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(F)=CC=2)=N1 AFQXHTAGFYVRPW-UHFFFAOYSA-N 0.000 claims 1
- OVIUCSJCXKKNJJ-UHFFFAOYSA-N [5-amino-3-(4-hydroxyanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(O)=CC=2)=N1 OVIUCSJCXKKNJJ-UHFFFAOYSA-N 0.000 claims 1
- ROMZHUACZANVAS-UHFFFAOYSA-N [5-amino-3-(4-hydroxyanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(O)=CC=2)=N1 ROMZHUACZANVAS-UHFFFAOYSA-N 0.000 claims 1
- PGRFZXCATCWPFQ-UHFFFAOYSA-N [5-amino-3-(4-methoxyanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(OC)=CC=C1NC1=NN(C(=O)C=2C=CC(C)=CC=2)C(N)=N1 PGRFZXCATCWPFQ-UHFFFAOYSA-N 0.000 claims 1
- JWOMSOYDNCERMM-UHFFFAOYSA-N [5-amino-3-(4-methoxyanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1NC1=NN(C(=O)C=2C=CC(OC(C)C)=CC=2)C(N)=N1 JWOMSOYDNCERMM-UHFFFAOYSA-N 0.000 claims 1
- JXMJWYRRCBQRKQ-UHFFFAOYSA-N [5-amino-3-(4-methylanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1NC1=NN(C(=O)C=2C=CC(C)=CC=2)C(N)=N1 JXMJWYRRCBQRKQ-UHFFFAOYSA-N 0.000 claims 1
- WPDXVUKKZVHUMT-UHFFFAOYSA-N [5-amino-3-(4-morpholin-4-ylanilino)-1,2,4-triazol-1-yl]-(3-chlorophenyl)methanone Chemical compound N=1N(C(=O)C=2C=C(Cl)C=CC=2)C(N)=NC=1NC(C=C1)=CC=C1N1CCOCC1 WPDXVUKKZVHUMT-UHFFFAOYSA-N 0.000 claims 1
- GBIWMBFZQDGSRG-UHFFFAOYSA-N [5-amino-3-(4-morpholin-4-ylanilino)-1,2,4-triazol-1-yl]-(3-hydroxyphenyl)methanone Chemical compound N=1N(C(=O)C=2C=C(O)C=CC=2)C(N)=NC=1NC(C=C1)=CC=C1N1CCOCC1 GBIWMBFZQDGSRG-UHFFFAOYSA-N 0.000 claims 1
- XWFONUMJSAGLMV-UHFFFAOYSA-N [5-amino-3-(4-morpholin-4-ylanilino)-1,2,4-triazol-1-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(=CC=3)N3CCOCC3)=N2)N)=C1 XWFONUMJSAGLMV-UHFFFAOYSA-N 0.000 claims 1
- KRHGGQWBCNCQHB-UHFFFAOYSA-N [5-amino-3-(4-morpholin-4-ylanilino)-1,2,4-triazol-1-yl]-(3-nitrophenyl)methanone Chemical compound N=1N(C(=O)C=2C=C(C=CC=2)[N+]([O-])=O)C(N)=NC=1NC(C=C1)=CC=C1N1CCOCC1 KRHGGQWBCNCQHB-UHFFFAOYSA-N 0.000 claims 1
- CACQLVPHSRQTNR-UHFFFAOYSA-N [5-amino-3-(4-morpholin-4-ylanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(=CC=2)N2CCOCC2)=N1 CACQLVPHSRQTNR-UHFFFAOYSA-N 0.000 claims 1
- KHSASCQGHQWGFP-UHFFFAOYSA-N [5-amino-3-(4-morpholin-4-ylanilino)-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(=CC=2)N2CCOCC2)=N1 KHSASCQGHQWGFP-UHFFFAOYSA-N 0.000 claims 1
- CIHXFXPATZZNPJ-UHFFFAOYSA-N [5-amino-3-(4-phenylmethoxyanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 CIHXFXPATZZNPJ-UHFFFAOYSA-N 0.000 claims 1
- JOSZMABFCXHDBH-UHFFFAOYSA-N [5-amino-3-(4-phenylmethoxyanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 JOSZMABFCXHDBH-UHFFFAOYSA-N 0.000 claims 1
- MSJGEBDRJWUUEM-UHFFFAOYSA-N [5-amino-3-(4-propan-2-yloxyanilino)-1,2,4-triazol-1-yl]-(3-chlorophenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NN(C(=O)C=2C=C(Cl)C=CC=2)C(N)=N1 MSJGEBDRJWUUEM-UHFFFAOYSA-N 0.000 claims 1
- DEBRYXIHPKWISX-UHFFFAOYSA-N [5-amino-3-(4-propan-2-yloxyanilino)-1,2,4-triazol-1-yl]-(3-hydroxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NN(C(=O)C=2C=C(O)C=CC=2)C(N)=N1 DEBRYXIHPKWISX-UHFFFAOYSA-N 0.000 claims 1
- AFMJPXURBDPFNN-UHFFFAOYSA-N [5-amino-3-(4-propan-2-yloxyanilino)-1,2,4-triazol-1-yl]-(3-nitrophenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NN(C(=O)C=2C=C(C=CC=2)[N+]([O-])=O)C(N)=N1 AFMJPXURBDPFNN-UHFFFAOYSA-N 0.000 claims 1
- ZIMISXMLZKIXOO-UHFFFAOYSA-N [5-amino-3-(4-propan-2-yloxyanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(C)=CC=2)C(N)=N1 ZIMISXMLZKIXOO-UHFFFAOYSA-N 0.000 claims 1
- WUKWQNAOZUIDJV-UHFFFAOYSA-N [5-amino-3-(4-propan-2-yloxyanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(OC(C)C)=CC=2)C(N)=N1 WUKWQNAOZUIDJV-UHFFFAOYSA-N 0.000 claims 1
- USKQOUSSJZOGFN-UHFFFAOYSA-N [5-amino-3-(4-pyrrolidin-1-ylanilino)-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(=CC=2)N2CCCC2)=N1 USKQOUSSJZOGFN-UHFFFAOYSA-N 0.000 claims 1
- GWHUZSGTRWLXTN-UHFFFAOYSA-N [5-amino-3-(4-pyrrolidin-1-ylanilino)-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(=CC=2)N2CCCC2)=N1 GWHUZSGTRWLXTN-UHFFFAOYSA-N 0.000 claims 1
- DUUWJCNYIUQURS-UHFFFAOYSA-N [5-amino-3-(4-pyrrolidin-1-ylanilino)-1,2,4-triazol-1-yl]-(4-tert-butylphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(=CC=2)N2CCCC2)=N1 DUUWJCNYIUQURS-UHFFFAOYSA-N 0.000 claims 1
- ZAWSNEMNSCRYEH-UHFFFAOYSA-N [5-amino-3-(4-pyrrolidin-1-ylanilino)-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(=CC=2)N2CCCC2)=N1 ZAWSNEMNSCRYEH-UHFFFAOYSA-N 0.000 claims 1
- GZLJNBYMXFJVIA-UHFFFAOYSA-N [5-amino-3-(4-pyrrolidin-1-ylanilino)-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(=CC=2)N2CCCC2)=N1 GZLJNBYMXFJVIA-UHFFFAOYSA-N 0.000 claims 1
- WRUJVGCHPMKKBX-UHFFFAOYSA-N [5-amino-3-[3-(1,3-oxazol-5-yl)anilino]-1,2,4-triazol-1-yl]-(3-propan-2-yloxyphenyl)methanone Chemical compound CC(C)OC1=CC=CC(C(=O)N2C(=NC(NC=3C=C(C=CC=3)C=3OC=NC=3)=N2)N)=C1 WRUJVGCHPMKKBX-UHFFFAOYSA-N 0.000 claims 1
- XQGHEZHFRSCLGG-UHFFFAOYSA-N [5-amino-3-[3-(1,3-oxazol-5-yl)anilino]-1,2,4-triazol-1-yl]-(4-tert-butylphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(C=CC=2)C=2OC=NC=2)=N1 XQGHEZHFRSCLGG-UHFFFAOYSA-N 0.000 claims 1
- UNJVSZVPQZHWDD-UHFFFAOYSA-N [5-amino-3-[3-(1,3-oxazol-5-yl)anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(C=CC=2)C=2OC=NC=2)=N1 UNJVSZVPQZHWDD-UHFFFAOYSA-N 0.000 claims 1
- MQWXEAYFRAPFDJ-UHFFFAOYSA-N [5-amino-3-[3-(2,2,2-trifluoroethoxy)anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OCC(F)(F)F)C=CC=2)=N1 MQWXEAYFRAPFDJ-UHFFFAOYSA-N 0.000 claims 1
- KMCDDVSCAQHYFA-UHFFFAOYSA-N [5-amino-3-[3-(2-methoxyethoxymethoxy)anilino]-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound COCCOCOC1=CC=CC(NC2=NN(C(N)=N2)C(=O)C=2C=C(C)C=CC=2)=C1 KMCDDVSCAQHYFA-UHFFFAOYSA-N 0.000 claims 1
- QPWSKUAWBAVQDT-UHFFFAOYSA-N [5-amino-3-[3-[2-(1,3-dioxolan-2-yl)ethoxy]anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(OCCC3OCCO3)C=CC=2)=N1 QPWSKUAWBAVQDT-UHFFFAOYSA-N 0.000 claims 1
- XITMXCIKKYYJKM-UHFFFAOYSA-N [5-amino-3-[3-chloro-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3,5-dichlorophenyl)methanone Chemical compound N=1N(C(=O)C=2C=C(Cl)C=C(Cl)C=2)C(N)=NC=1NC(C=C1Cl)=CC=C1OCCN1CCCC1 XITMXCIKKYYJKM-UHFFFAOYSA-N 0.000 claims 1
- GUUQUTINQDKMLJ-UHFFFAOYSA-N [5-amino-3-[3-fluoro-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1h-indol-6-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3NC=CC3=CC=2)C(N)=NC=1NC(C=C1F)=CC=C1OCCN1CCCC1 GUUQUTINQDKMLJ-UHFFFAOYSA-N 0.000 claims 1
- OSGDJRWDQMDIDW-UHFFFAOYSA-N [5-amino-3-[3-fluoro-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(F)C(OCCN3CCCC3)=CC=2)=N1 OSGDJRWDQMDIDW-UHFFFAOYSA-N 0.000 claims 1
- DQMITHQZJPBMCK-UHFFFAOYSA-N [5-amino-3-[3-fluoro-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-(thiadiazol-4-yl)phenyl]methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)C=2N=NSC=2)C(N)=NC=1NC(C=C1F)=CC=C1OCCN1CCCC1 DQMITHQZJPBMCK-UHFFFAOYSA-N 0.000 claims 1
- WQNMUCAEKYIKPD-UHFFFAOYSA-N [5-amino-3-[3-fluoro-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=C(F)C(OCCN3CCCC3)=CC=2)=N1 WQNMUCAEKYIKPD-UHFFFAOYSA-N 0.000 claims 1
- ZYMYIFUSNBYWMO-UHFFFAOYSA-N [5-amino-3-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1h-indol-6-yl)methanone Chemical compound COC1=CC(NC2=NN(C(N)=N2)C(=O)C=2C=C3NC=CC3=CC=2)=CC=C1OCCN1CCCC1 ZYMYIFUSNBYWMO-UHFFFAOYSA-N 0.000 claims 1
- URMOUCIRWULZEC-UHFFFAOYSA-N [5-amino-3-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-morpholin-4-ylphenyl)methanone Chemical compound C=1C=C(OCCN2CCCC2)C(OC)=CC=1NC(=N1)N=C(N)N1C(=O)C(C=1)=CC=CC=1N1CCOCC1 URMOUCIRWULZEC-UHFFFAOYSA-N 0.000 claims 1
- ZDANCCLBWWQTLX-UHFFFAOYSA-N [5-amino-3-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C=1C=C(OCCN2CCCC2)C(OC)=CC=1NC(=N1)N=C(N)N1C(=O)C1=CC=C(OC(C)C)C=C1 ZDANCCLBWWQTLX-UHFFFAOYSA-N 0.000 claims 1
- UVEHFXQUYPPGSJ-UHFFFAOYSA-N [5-amino-3-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-tert-butylphenyl)methanone Chemical compound C=1C=C(OCCN2CCCC2)C(OC)=CC=1NC(=N1)N=C(N)N1C(=O)C1=CC=C(C(C)(C)C)C=C1 UVEHFXQUYPPGSJ-UHFFFAOYSA-N 0.000 claims 1
- UPNCSRBLWNDCLA-UHFFFAOYSA-N [5-amino-3-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-(thiadiazol-4-yl)phenyl]methanone Chemical compound C=1C=C(OCCN2CCCC2)C(OC)=CC=1NC(=N1)N=C(N)N1C(=O)C(C=C1)=CC=C1C1=CSN=N1 UPNCSRBLWNDCLA-UHFFFAOYSA-N 0.000 claims 1
- JMNJCGDJIZJZDI-UHFFFAOYSA-N [5-amino-3-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C=1C=C(OCCN2CCCC2)C(OC)=CC=1NC(=N1)N=C(N)N1C(=O)C1=CC=C(OC(C)(C)C)C=C1 JMNJCGDJIZJZDI-UHFFFAOYSA-N 0.000 claims 1
- PISIQYPJOQFVTJ-UHFFFAOYSA-N [5-amino-3-[4-(2,2,2-trifluoroethoxy)anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCC(F)(F)F)=CC=2)=N1 PISIQYPJOQFVTJ-UHFFFAOYSA-N 0.000 claims 1
- MIVCWJJPHJIZIB-UHFFFAOYSA-N [5-amino-3-[4-(2-imidazol-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1-benzothiophen-2-yl)methanone Chemical compound N=1N(C(=O)C=2SC3=CC=CC=C3C=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1C=CN=C1 MIVCWJJPHJIZIB-UHFFFAOYSA-N 0.000 claims 1
- BQUBZOLEDXRCRX-UHFFFAOYSA-N [5-amino-3-[4-(2-imidazol-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1-benzothiophen-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3C=CSC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1C=CN=C1 BQUBZOLEDXRCRX-UHFFFAOYSA-N 0.000 claims 1
- MHGGOJPSDKGXSZ-UHFFFAOYSA-N [5-amino-3-[4-(2-imidazol-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1h-indol-6-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3NC=CC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1C=CN=C1 MHGGOJPSDKGXSZ-UHFFFAOYSA-N 0.000 claims 1
- FEHRWSIQRQSCMY-UHFFFAOYSA-N [5-amino-3-[4-(2-imidazol-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3C=NC=C3)=CC=2)=N1 FEHRWSIQRQSCMY-UHFFFAOYSA-N 0.000 claims 1
- DOUNFQJIVHESII-UHFFFAOYSA-N [5-amino-3-[4-(2-imidazol-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[3-(dimethylamino)phenyl]methanone Chemical compound CN(C)C1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4C=NC=C4)=CC=3)=N2)N)=C1 DOUNFQJIVHESII-UHFFFAOYSA-N 0.000 claims 1
- RVDDPBMCAOCDTF-UHFFFAOYSA-N [5-amino-3-[4-(2-imidazol-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[3-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound CC(C)(C)OC1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4C=NC=C4)=CC=3)=N2)N)=C1 RVDDPBMCAOCDTF-UHFFFAOYSA-N 0.000 claims 1
- MYKPNNASKZETTG-UHFFFAOYSA-N [5-amino-3-[4-(2-imidazol-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3C=NC=C3)=CC=2)=N1 MYKPNNASKZETTG-UHFFFAOYSA-N 0.000 claims 1
- ZACGBOPBKWBMNQ-UHFFFAOYSA-N [5-amino-3-[4-(2-imidazol-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3C=NC=C3)=CC=2)=N1 ZACGBOPBKWBMNQ-UHFFFAOYSA-N 0.000 claims 1
- CCEDDBIKOFRKAH-UHFFFAOYSA-N [5-amino-3-[4-(2-morpholin-4-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1h-indol-6-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3NC=CC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCOCC1 CCEDDBIKOFRKAH-UHFFFAOYSA-N 0.000 claims 1
- LWSNIUDTSIXZLQ-UHFFFAOYSA-N [5-amino-3-[4-(2-morpholin-4-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-propan-2-yloxyphenyl)methanone Chemical compound CC(C)OC1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCOCC4)=CC=3)=N2)N)=C1 LWSNIUDTSIXZLQ-UHFFFAOYSA-N 0.000 claims 1
- BNCJZNFFMKONCE-UHFFFAOYSA-N [5-amino-3-[4-(2-morpholin-4-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-tert-butylphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCOCC3)=CC=2)=N1 BNCJZNFFMKONCE-UHFFFAOYSA-N 0.000 claims 1
- JPPJJTBLJIPAPV-UHFFFAOYSA-N [5-amino-3-[4-(2-morpholin-4-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(5-propan-2-yloxypyridin-3-yl)methanone Chemical compound CC(C)OC1=CN=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCOCC4)=CC=3)=N2)N)=C1 JPPJJTBLJIPAPV-UHFFFAOYSA-N 0.000 claims 1
- YSSWVNQEOOTDTP-UHFFFAOYSA-N [5-amino-3-[4-(2-morpholin-4-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCOCC3)=CC=2)=N1 YSSWVNQEOOTDTP-UHFFFAOYSA-N 0.000 claims 1
- BPEVRXXPXGUPDS-UHFFFAOYSA-N [5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1,3-benzodioxol-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3OCOC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCCC1 BPEVRXXPXGUPDS-UHFFFAOYSA-N 0.000 claims 1
- FDJDVHPUNMJXQS-UHFFFAOYSA-N [5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCCC4)=CC=3)=N2)N)=C1 FDJDVHPUNMJXQS-UHFFFAOYSA-N 0.000 claims 1
- NYITYFXTQCODBO-UHFFFAOYSA-N [5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCCC4)=CC=3)=N2)N)=C1 NYITYFXTQCODBO-UHFFFAOYSA-N 0.000 claims 1
- BYZKVVOYVLHTOF-UHFFFAOYSA-N [5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-propan-2-yloxyphenyl)methanone Chemical compound CC(C)OC1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCCC4)=CC=3)=N2)N)=C1 BYZKVVOYVLHTOF-UHFFFAOYSA-N 0.000 claims 1
- VWAKZHUAFAJYAX-UHFFFAOYSA-N [5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-cyclohexylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)C2CCCCC2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCCC1 VWAKZHUAFAJYAX-UHFFFAOYSA-N 0.000 claims 1
- XEVZDAFRTZGAGE-UHFFFAOYSA-N [5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-methoxycyclohexyl)methanone Chemical compound C1CC(OC)CCC1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 XEVZDAFRTZGAGE-UHFFFAOYSA-N 0.000 claims 1
- SNRIEVIEGREGBS-UHFFFAOYSA-N [5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 SNRIEVIEGREGBS-UHFFFAOYSA-N 0.000 claims 1
- BKLAEZKISLKCGC-UHFFFAOYSA-N [5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-propan-2-ylphenyl)methanone Chemical compound C1=CC(C(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 BKLAEZKISLKCGC-UHFFFAOYSA-N 0.000 claims 1
- YGWABRHGGYRWCP-UHFFFAOYSA-N [5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[3-(dimethylamino)phenyl]methanone Chemical compound CN(C)C1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCCC4)=CC=3)=N2)N)=C1 YGWABRHGGYRWCP-UHFFFAOYSA-N 0.000 claims 1
- BOHVUNKJZMUFQG-UHFFFAOYSA-N [5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 BOHVUNKJZMUFQG-UHFFFAOYSA-N 0.000 claims 1
- FHGYTIPUBYTWLH-UHFFFAOYSA-N [5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCC3)=CC=2)=N1 FHGYTIPUBYTWLH-UHFFFAOYSA-N 0.000 claims 1
- ZIQGXJRCUSDDSP-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1,3-benzodioxol-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3OCOC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 ZIQGXJRCUSDDSP-UHFFFAOYSA-N 0.000 claims 1
- NPOGYEKLJFATEZ-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1,3-benzothiazol-6-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3SC=NC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 NPOGYEKLJFATEZ-UHFFFAOYSA-N 0.000 claims 1
- IQVMMLHCIWFEMX-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1-benzothiophen-2-yl)methanone Chemical compound N=1N(C(=O)C=2SC3=CC=CC=C3C=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 IQVMMLHCIWFEMX-UHFFFAOYSA-N 0.000 claims 1
- BMTGRPKVKCRHNL-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1-benzothiophen-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3C=CSC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 BMTGRPKVKCRHNL-UHFFFAOYSA-N 0.000 claims 1
- ONIFBTFCFMFNLG-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1h-indol-2-yl)methanone Chemical compound N=1N(C(=O)C=2NC3=CC=CC=C3C=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 ONIFBTFCFMFNLG-UHFFFAOYSA-N 0.000 claims 1
- CSAVOUREYLKSFH-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1h-indol-3-yl)methanone Chemical compound N=1N(C(=O)C=2C3=CC=CC=C3NC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 CSAVOUREYLKSFH-UHFFFAOYSA-N 0.000 claims 1
- IYTRLEVOIVCSKS-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1h-indol-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3C=CNC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 IYTRLEVOIVCSKS-UHFFFAOYSA-N 0.000 claims 1
- ZDODCAMEJADIMO-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(1h-indol-6-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3NC=CC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 ZDODCAMEJADIMO-UHFFFAOYSA-N 0.000 claims 1
- WHUVIORJCJRDGQ-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3OCCOC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 WHUVIORJCJRDGQ-UHFFFAOYSA-N 0.000 claims 1
- OFQZIFROVVDBOL-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(2,3-dihydro-1-benzofuran-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3CCOC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 OFQZIFROVVDBOL-UHFFFAOYSA-N 0.000 claims 1
- PQKHESAPHRHJGE-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(2,6-difluorophenyl)methanone Chemical compound N=1N(C(=O)C=2C(=CC=CC=2F)F)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 PQKHESAPHRHJGE-UHFFFAOYSA-N 0.000 claims 1
- CORYDBAMRNVLSN-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(2h-benzotriazol-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3N=NNC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 CORYDBAMRNVLSN-UHFFFAOYSA-N 0.000 claims 1
- JFPTZTHNFDZNSH-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3,5-difluoro-4-methoxyphenyl)methanone Chemical compound C1=C(F)C(OC)=C(F)C=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 JFPTZTHNFDZNSH-UHFFFAOYSA-N 0.000 claims 1
- JOMLJZGDYYOAHL-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=C(F)C(OC)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 JOMLJZGDYYOAHL-UHFFFAOYSA-N 0.000 claims 1
- LPNNBSRAMLWSKI-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCC4)=CC=3)=N2)N)=C1 LPNNBSRAMLWSKI-UHFFFAOYSA-N 0.000 claims 1
- VGJBJKUKHFUGTO-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCC4)=CC=3)=N2)N)=C1 VGJBJKUKHFUGTO-UHFFFAOYSA-N 0.000 claims 1
- YYEUAPZIXFZNMD-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-methylthiophen-2-yl)methanone Chemical compound C1=CSC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCC4)=CC=3)=N2)N)=C1C YYEUAPZIXFZNMD-UHFFFAOYSA-N 0.000 claims 1
- FVBWHRIQXBWKJL-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-morpholin-4-ylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=C(C=CC=2)N2CCOCC2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 FVBWHRIQXBWKJL-UHFFFAOYSA-N 0.000 claims 1
- PMJKSODWBZVCKQ-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3-thiophen-2-ylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=C(C=CC=2)C=2SC=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 PMJKSODWBZVCKQ-UHFFFAOYSA-N 0.000 claims 1
- XYCPGWBYOGDHGU-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(3h-benzimidazol-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3N=CNC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 XYCPGWBYOGDHGU-UHFFFAOYSA-N 0.000 claims 1
- JRTMMKHRRJVMIA-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-imidazol-1-ylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)N2C=NC=C2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 JRTMMKHRRJVMIA-UHFFFAOYSA-N 0.000 claims 1
- YPDRFTHPKGCNKC-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 YPDRFTHPKGCNKC-UHFFFAOYSA-N 0.000 claims 1
- XCNPORZRTBGECV-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-methylsulfanylphenyl)methanone Chemical compound C1=CC(SC)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 XCNPORZRTBGECV-UHFFFAOYSA-N 0.000 claims 1
- VQBUVCCAVJNXTB-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-morpholin-4-ylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)N2CCOCC2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 VQBUVCCAVJNXTB-UHFFFAOYSA-N 0.000 claims 1
- WPWOVYCWRHJLFI-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-phenoxyphenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 WPWOVYCWRHJLFI-UHFFFAOYSA-N 0.000 claims 1
- HNGQGDXHGHDVQQ-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-phenylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 HNGQGDXHGHDVQQ-UHFFFAOYSA-N 0.000 claims 1
- PFUCBZSHERSSMK-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-piperidin-1-ylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)N2CCCCC2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 PFUCBZSHERSSMK-UHFFFAOYSA-N 0.000 claims 1
- NZFYFXXAFWORRR-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 NZFYFXXAFWORRR-UHFFFAOYSA-N 0.000 claims 1
- ZWCJHARTEPCQKR-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-pyrrol-1-ylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)N2C=CC=C2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 ZWCJHARTEPCQKR-UHFFFAOYSA-N 0.000 claims 1
- JURGVAAAABAXNS-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-thiophen-2-ylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)C=2SC=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 JURGVAAAABAXNS-UHFFFAOYSA-N 0.000 claims 1
- MDOGREYYFSEAQG-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-thiophen-3-ylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)C2=CSC=C2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 MDOGREYYFSEAQG-UHFFFAOYSA-N 0.000 claims 1
- BKVPHHPGQXHQIG-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(5-methylthiophen-2-yl)methanone Chemical compound S1C(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 BKVPHHPGQXHQIG-UHFFFAOYSA-N 0.000 claims 1
- LYQSVOHKMQPJQX-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(6-methylpyridin-3-yl)methanone Chemical compound C1=NC(C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 LYQSVOHKMQPJQX-UHFFFAOYSA-N 0.000 claims 1
- OABDRYPHXGUPKA-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(thiadiazol-4-yl)methanone Chemical compound N=1N(C(=O)C=2N=NSC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 OABDRYPHXGUPKA-UHFFFAOYSA-N 0.000 claims 1
- NUQOBIBOZOZSKA-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[3-(1,3-thiazol-2-yl)phenyl]methanone Chemical compound N=1N(C(=O)C=2C=C(C=CC=2)C=2SC=CN=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 NUQOBIBOZOZSKA-UHFFFAOYSA-N 0.000 claims 1
- GGYFSOQVTYQKKI-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[3-(dimethylamino)phenyl]methanone Chemical compound CN(C)C1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCC4)=CC=3)=N2)N)=C1 GGYFSOQVTYQKKI-UHFFFAOYSA-N 0.000 claims 1
- QKQFKLKHQPURLC-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[3-(trifluoromethoxy)phenyl]methanone Chemical compound N=1N(C(=O)C=2C=C(OC(F)(F)F)C=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 QKQFKLKHQPURLC-UHFFFAOYSA-N 0.000 claims 1
- WQABRBOHQKAGIX-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[3-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound CC(C)(C)OC1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCC4)=CC=3)=N2)N)=C1 WQABRBOHQKAGIX-UHFFFAOYSA-N 0.000 claims 1
- PQUGTXSHVVNXGK-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-(1,1-dioxo-1,4-thiazinan-4-yl)phenyl]methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)N2CCS(=O)(=O)CC2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 PQUGTXSHVVNXGK-UHFFFAOYSA-N 0.000 claims 1
- FRJPNVYGGMNDKH-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-(2-morpholin-4-ylethoxy)phenyl]methanone Chemical compound N=1N(C(=O)C=2C=CC(OCCN3CCOCC3)=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 FRJPNVYGGMNDKH-UHFFFAOYSA-N 0.000 claims 1
- WWBHUVBMAAKYTD-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-(4-methylpiperazin-1-yl)phenyl]methanone Chemical compound C1CN(C)CCN1C1=CC=C(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCC4)=CC=3)=N2)N)C=C1 WWBHUVBMAAKYTD-UHFFFAOYSA-N 0.000 claims 1
- QLIJTNYNWQTFJL-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 QLIJTNYNWQTFJL-UHFFFAOYSA-N 0.000 claims 1
- ULUOWDCBDMRKQY-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-(methylamino)phenyl]methanone Chemical compound C1=CC(NC)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 ULUOWDCBDMRKQY-UHFFFAOYSA-N 0.000 claims 1
- QPNSYKAASHLMTD-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-[4-(trifluoromethoxy)phenyl]methanone Chemical compound N=1N(C(=O)C=2C=CC(OC(F)(F)F)=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 QPNSYKAASHLMTD-UHFFFAOYSA-N 0.000 claims 1
- UNTQWXDZVIBUMJ-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-pyridin-4-ylmethanone Chemical compound N=1N(C(=O)C=2C=CN=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 UNTQWXDZVIBUMJ-UHFFFAOYSA-N 0.000 claims 1
- PAIGVINSUPDERH-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-quinolin-6-ylmethanone Chemical compound N=1N(C(=O)C=2C=C3C=CC=NC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 PAIGVINSUPDERH-UHFFFAOYSA-N 0.000 claims 1
- YEDRNIKVSDLMJF-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-thiophen-2-ylmethanone Chemical compound N=1N(C(=O)C=2SC=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 YEDRNIKVSDLMJF-UHFFFAOYSA-N 0.000 claims 1
- UXLMZOQRVBYXOV-UHFFFAOYSA-N [5-amino-3-[4-(3-pyrrolidin-1-ylpropoxy)anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCCN3CCCC3)=CC=2)=N1 UXLMZOQRVBYXOV-UHFFFAOYSA-N 0.000 claims 1
- NVAQRBJFFXCQBG-UHFFFAOYSA-N [5-amino-3-[4-(3-pyrrolidin-1-ylpropoxy)anilino]-1,2,4-triazol-1-yl]-[3-(dimethylamino)phenyl]methanone Chemical compound CN(C)C1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCCN4CCCC4)=CC=3)=N2)N)=C1 NVAQRBJFFXCQBG-UHFFFAOYSA-N 0.000 claims 1
- ATVCXCKXBKWGAJ-UHFFFAOYSA-N [5-amino-3-[4-(3-pyrrolidin-1-ylpropoxy)anilino]-1,2,4-triazol-1-yl]-[3-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound CC(C)(C)OC1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCCN4CCCC4)=CC=3)=N2)N)=C1 ATVCXCKXBKWGAJ-UHFFFAOYSA-N 0.000 claims 1
- WWKVOBHYPQZZRF-UHFFFAOYSA-N [5-amino-3-[4-(3-pyrrolidin-1-ylpropoxy)anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCCN3CCCC3)=CC=2)=N1 WWKVOBHYPQZZRF-UHFFFAOYSA-N 0.000 claims 1
- UWICBMGEYYSKFU-UHFFFAOYSA-N [5-amino-3-[4-(3-pyrrolidin-1-ylpropoxy)anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCCN3CCCC3)=CC=2)=N1 UWICBMGEYYSKFU-UHFFFAOYSA-N 0.000 claims 1
- DENMOERQBFNUFG-UHFFFAOYSA-N [5-amino-3-[4-(4-methylpiperazin-1-yl)anilino]-1,2,4-triazol-1-yl]-(3-bicyclo[2.2.1]heptanyl)methanone Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NN(C(=O)C2C3CCC(C3)C2)C(N)=N1 DENMOERQBFNUFG-UHFFFAOYSA-N 0.000 claims 1
- BXNUTPVLNVOCMN-UHFFFAOYSA-N [5-amino-3-[4-(4-methylpiperazin-1-yl)anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(=CC=2)N2CCN(C)CC2)=N1 BXNUTPVLNVOCMN-UHFFFAOYSA-N 0.000 claims 1
- DIQOIGFWGSXDON-UHFFFAOYSA-N [5-amino-3-[4-(4-methylpiperazin-1-yl)anilino]-1,2,4-triazol-1-yl]-[3-(dimethylamino)phenyl]methanone Chemical compound CN(C)C1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(=CC=3)N3CCN(C)CC3)=N2)N)=C1 DIQOIGFWGSXDON-UHFFFAOYSA-N 0.000 claims 1
- CXXLXGKNCWBXEF-UHFFFAOYSA-N [5-amino-3-[4-(4-methylpiperazin-1-yl)anilino]-1,2,4-triazol-1-yl]-[3-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NN(C(=O)C=2C=C(OC(C)(C)C)C=CC=2)C(N)=N1 CXXLXGKNCWBXEF-UHFFFAOYSA-N 0.000 claims 1
- FHOIHBNTAWYUMB-UHFFFAOYSA-N [5-amino-3-[4-(4-methylpiperazin-1-yl)anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(=CC=2)N2CCN(C)CC2)=N1 FHOIHBNTAWYUMB-UHFFFAOYSA-N 0.000 claims 1
- HUSFYRCJIYIBNM-UHFFFAOYSA-N [5-amino-3-[4-(4-methylpiperazin-1-yl)anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NN(C(=O)C=2C=CC(OC(C)(C)C)=CC=2)C(N)=N1 HUSFYRCJIYIBNM-UHFFFAOYSA-N 0.000 claims 1
- NFWQXJAPMJBITG-UHFFFAOYSA-N [5-amino-3-[4-[2-(1,3-dioxolan-2-yl)ethoxy]anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCC3OCCO3)=CC=2)=N1 NFWQXJAPMJBITG-UHFFFAOYSA-N 0.000 claims 1
- AGFVIAPXMFSUAD-UHFFFAOYSA-N [5-amino-3-[4-[2-(2,3-dihydro-1h-isoindol-1-yl)ethoxy]anilino]-1,2,4-triazol-1-yl]-(1h-indol-6-yl)methanone Chemical compound C1=C2C=CNC2=CC(C(=O)N2N=C(NC=3C=CC(OCCC4C5=CC=CC=C5CN4)=CC=3)N=C2N)=C1 AGFVIAPXMFSUAD-UHFFFAOYSA-N 0.000 claims 1
- MCNIHHXFAXQFSA-UHFFFAOYSA-N [5-amino-3-[4-[2-(2,3-dihydro-1h-isoindol-1-yl)ethoxy]anilino]-1,2,4-triazol-1-yl]-(4-morpholin-4-ylphenyl)methanone Chemical compound NC1=NC(NC=2C=CC(OCCC3C4=CC=CC=C4CN3)=CC=2)=NN1C(=O)C(C=C1)=CC=C1N1CCOCC1 MCNIHHXFAXQFSA-UHFFFAOYSA-N 0.000 claims 1
- GQOYUEBZDSPFPQ-UHFFFAOYSA-N [5-amino-3-[4-[2-(2,3-dihydro-1h-isoindol-1-yl)ethoxy]anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCC3C4=CC=CC=C4CN3)=CC=2)=N1 GQOYUEBZDSPFPQ-UHFFFAOYSA-N 0.000 claims 1
- MWSBFZGKQZMVBQ-UHFFFAOYSA-N [5-amino-3-[4-[2-(2,3-dihydro-1h-isoindol-1-yl)ethoxy]anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCC3C4=CC=CC=C4CN3)=CC=2)=N1 MWSBFZGKQZMVBQ-UHFFFAOYSA-N 0.000 claims 1
- GPJCXBGHNUNIDL-UHFFFAOYSA-N [5-amino-3-[4-[2-(azepan-1-yl)ethoxy]anilino]-1,2,4-triazol-1-yl]-(1h-indol-6-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3NC=CC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCCCC1 GPJCXBGHNUNIDL-UHFFFAOYSA-N 0.000 claims 1
- YMGVFBIXLYEEPG-UHFFFAOYSA-N [5-amino-3-[4-[2-(azepan-1-yl)ethoxy]anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCCC3)=CC=2)=N1 YMGVFBIXLYEEPG-UHFFFAOYSA-N 0.000 claims 1
- FBOSCOFUSXSJFR-UHFFFAOYSA-N [5-amino-3-[4-[2-(azepan-1-yl)ethoxy]anilino]-1,2,4-triazol-1-yl]-(4-tert-butylphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCCC3)=CC=2)=N1 FBOSCOFUSXSJFR-UHFFFAOYSA-N 0.000 claims 1
- WOSXALFTTCGOIZ-UHFFFAOYSA-N [5-amino-3-[4-[2-(azepan-1-yl)ethoxy]anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCCCC3)=CC=2)=N1 WOSXALFTTCGOIZ-UHFFFAOYSA-N 0.000 claims 1
- CMLKIUVKPPNMTF-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)ethoxy]anilino]-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(C)=CC=2)C(N)=N1 CMLKIUVKPPNMTF-UHFFFAOYSA-N 0.000 claims 1
- RTLULVTVVBDSDM-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)ethoxy]anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN(C)C)=CC=2)=N1 RTLULVTVVBDSDM-UHFFFAOYSA-N 0.000 claims 1
- LBBHRIGBOUDBRS-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)ethoxy]anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(=CC=2)N(C)C)C(N)=N1 LBBHRIGBOUDBRS-UHFFFAOYSA-N 0.000 claims 1
- SBYOFFSKGSUHND-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)ethoxy]anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(OC(C)(C)C)=CC=2)C(N)=N1 SBYOFFSKGSUHND-UHFFFAOYSA-N 0.000 claims 1
- DOAOXLBNDMKROY-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)propoxy]anilino]-1,2,4-triazol-1-yl]-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCC(C)N(C)C)=CC=2)=N1 DOAOXLBNDMKROY-UHFFFAOYSA-N 0.000 claims 1
- SWKQJEHGFYCCML-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)propoxy]anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(OCC(C)N(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(=CC=2)N(C)C)C(N)=N1 SWKQJEHGFYCCML-UHFFFAOYSA-N 0.000 claims 1
- MUQZHQIPUVMVNR-UHFFFAOYSA-N [5-amino-3-[4-[2-(dimethylamino)propoxy]anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OCC(C)N(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(OC(C)(C)C)=CC=2)C(N)=N1 MUQZHQIPUVMVNR-UHFFFAOYSA-N 0.000 claims 1
- XULOGEQBAXOQEB-KRWDZBQOSA-N [5-amino-3-[4-[2-[(3s)-3-fluoropyrrolidin-1-yl]ethoxy]anilino]-1,2,4-triazol-1-yl]-(1h-indol-6-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3NC=CC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CC[C@H](F)C1 XULOGEQBAXOQEB-KRWDZBQOSA-N 0.000 claims 1
- CGGDXBVNKUMGTM-INIZCTEOSA-N [5-amino-3-[4-[2-[(3s)-3-fluoropyrrolidin-1-yl]ethoxy]anilino]-1,2,4-triazol-1-yl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3OCCOC3=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CC[C@H](F)C1 CGGDXBVNKUMGTM-INIZCTEOSA-N 0.000 claims 1
- NKMYMZZVJYWLMK-KRWDZBQOSA-N [5-amino-3-[4-[2-[(3s)-3-fluoropyrrolidin-1-yl]ethoxy]anilino]-1,2,4-triazol-1-yl]-[4-(dimethylamino)phenyl]methanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3C[C@@H](F)CC3)=CC=2)=N1 NKMYMZZVJYWLMK-KRWDZBQOSA-N 0.000 claims 1
- XLEJTDFDSNDDOA-SFHVURJKSA-N [5-amino-3-[4-[2-[(3s)-3-fluoropyrrolidin-1-yl]ethoxy]anilino]-1,2,4-triazol-1-yl]-[4-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3C[C@@H](F)CC3)=CC=2)=N1 XLEJTDFDSNDDOA-SFHVURJKSA-N 0.000 claims 1
- DGSVYYMCDPETKA-UHFFFAOYSA-N [5-amino-3-[4-[3-(dimethylamino)propoxy]anilino]-1,2,4-triazol-1-yl]-(4-methylphenyl)methanone Chemical compound C1=CC(OCCCN(C)C)=CC=C1NC1=NN(C(=O)C=2C=CC(C)=CC=2)C(N)=N1 DGSVYYMCDPETKA-UHFFFAOYSA-N 0.000 claims 1
- BYJZHXOTFQRQKF-UHFFFAOYSA-N [5-amino-3-[[2-(oxan-2-yloxymethyl)-1-benzofuran-5-yl]amino]-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C(=NC(NC=3C=C4C=C(COC5OCCCC5)OC4=CC=3)=N2)N)=C1 BYJZHXOTFQRQKF-UHFFFAOYSA-N 0.000 claims 1
- OHLSVDKURRPCMA-UHFFFAOYSA-N [5-amino-3-[n-(2-hydroxyethoxy)anilino]-1,2,4-triazol-1-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)N2C(=NC(=N2)N(OCCO)C=2C=CC=CC=2)N)=C1 OHLSVDKURRPCMA-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- RPSYDJLGXZBKTR-UHFFFAOYSA-N methyl 2-[3-[[5-amino-1-(3-methylbenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(NC2=NN(C(N)=N2)C(=O)C=2C=C(C)C=CC=2)=C1 RPSYDJLGXZBKTR-UHFFFAOYSA-N 0.000 claims 1
- RZELWGOKESWMKX-UHFFFAOYSA-N methyl 2-[3-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetate Chemical compound COC(=O)COC1=CC=CC(NC2=NN(C(N)=N2)C(=O)C=2C=CC(OC(C)C)=CC=2)=C1 RZELWGOKESWMKX-UHFFFAOYSA-N 0.000 claims 1
- HRHUEZYMNYVRKZ-UHFFFAOYSA-N methyl 2-[4-[[5-amino-1-(4-propan-2-yloxybenzoyl)-1,2,4-triazol-3-yl]amino]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OC)=CC=C1NC1=NN(C(=O)C=2C=CC(OC(C)C)=CC=2)C(N)=N1 HRHUEZYMNYVRKZ-UHFFFAOYSA-N 0.000 claims 1
- MWKVKSICXMIXCE-UHFFFAOYSA-N methyl 3-[5-amino-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carbonyl]benzoate Chemical compound COC(=O)C1=CC=CC(C(=O)N2C(=NC(NC=3C=CC(OCCN4CCCCC4)=CC=3)=N2)N)=C1 MWKVKSICXMIXCE-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- WFEVFIDXUMSSRB-UHFFFAOYSA-N n-[4-[5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carbonyl]phenyl]-2,2-dimethylpropanamide Chemical compound C1=CC(NC(=O)C(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 WFEVFIDXUMSSRB-UHFFFAOYSA-N 0.000 claims 1
- MEXNIACOWQTXMF-UHFFFAOYSA-N n-[5-amino-1-(3-methylbenzoyl)-1,2,4-triazol-3-yl]-n-[3-[4-(2-chloro-6-fluorophenyl)piperazin-1-yl]propyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)N(CCCN2CCN(CC2)C=2C(=CC=CC=2F)Cl)C2=NN(C(N)=N2)C(=O)C=2C=C(C)C=CC=2)=C1 MEXNIACOWQTXMF-UHFFFAOYSA-N 0.000 claims 1
- JGNUEHAWRGWWMP-UHFFFAOYSA-N n-phenyl-1,2,4-triazol-1-amine Chemical compound C1=NC=NN1NC1=CC=CC=C1 JGNUEHAWRGWWMP-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims 1
- JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical compound C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- AFNNIHIBTGXLNY-UHFFFAOYSA-N tert-butyl 5-amino-3-(4-piperidin-1-ylanilino)-1,2,4-triazole-1-carboxylate Chemical compound N1=C(N)N(C(=O)OC(C)(C)C)N=C1NC1=CC=C(N2CCCCC2)C=C1 AFNNIHIBTGXLNY-UHFFFAOYSA-N 0.000 claims 1
- FIVTXGSTVPHMFT-UHFFFAOYSA-N tert-butyl n-[4-[5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carbonyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 FIVTXGSTVPHMFT-UHFFFAOYSA-N 0.000 claims 1
- DHGXKEQQMGHMBH-UHFFFAOYSA-N tert-butyl n-[[4-[5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carbonyl]phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OC(C)(C)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 DHGXKEQQMGHMBH-UHFFFAOYSA-N 0.000 claims 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 0 *CC(*)*C(N**)=N Chemical compound *CC(*)*C(N**)=N 0.000 description 2
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71467305P | 2005-09-07 | 2005-09-07 | |
| US78016606P | 2006-03-07 | 2006-03-07 | |
| US81314306P | 2006-06-12 | 2006-06-12 | |
| PCT/US2006/034970 WO2007030680A2 (en) | 2005-09-07 | 2006-09-07 | Triazole derivatives useful as axl inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009507080A JP2009507080A (ja) | 2009-02-19 |
| JP2009507080A5 true JP2009507080A5 (enExample) | 2009-10-22 |
Family
ID=37622141
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008530213A Pending JP2009507080A (ja) | 2005-09-07 | 2006-09-07 | Ａｘｌ阻害剤として有用なトリアゾール誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7884119B2 (enExample) |
| EP (1) | EP1922310A2 (enExample) |
| JP (1) | JP2009507080A (enExample) |
| CA (1) | CA2621503C (enExample) |
| WO (1) | WO2007030680A2 (enExample) |
Families Citing this family (85)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9424392B2 (en) | 2005-11-26 | 2016-08-23 | Natera, Inc. | System and method for cleaning noisy genetic data from target individuals using genetic data from genetically related individuals |
| US11111544B2 (en) | 2005-07-29 | 2021-09-07 | Natera, Inc. | System and method for cleaning noisy genetic data and determining chromosome copy number |
| US11111543B2 (en) | 2005-07-29 | 2021-09-07 | Natera, Inc. | System and method for cleaning noisy genetic data and determining chromosome copy number |
| CA2710230C (en) | 2006-12-29 | 2016-02-23 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic aryl and bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CA2710051C (en) | 2006-12-29 | 2017-05-16 | Rigel Pharmaceuticals, Inc. | Substituted triazoles useful as axl inhibitors |
| RS53281B (sr) | 2006-12-29 | 2014-08-29 | Rigel Pharmaceuticals Inc. | Policiklični heteroaril supstituisani triazoli koji su korisni kao axl inhibitori |
| CN101622248B (zh) | 2006-12-29 | 2013-04-17 | 里格尔制药公司 | 用作axl抑制剂的n3-杂芳基取代的三唑和n5-杂芳基取代的三唑 |
| ES2406930T3 (es) | 2006-12-29 | 2013-06-10 | Rigel Pharmaceuticals, Inc. | Triazoles sustituidos con arilo bicíclico y heteroarilo bicíclico útiles como inhibidores de AXL |
| EP2170395A1 (en) * | 2007-07-02 | 2010-04-07 | Wyeth LLC | Modulators of axl for use in treating bone disorders |
| CA2704052C (en) * | 2007-10-26 | 2015-04-21 | Rigel Pharmaceuticals, Inc. | Polycyclic aryl substituted triazoles and polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CA2703519C (en) | 2007-11-09 | 2017-04-18 | The Salk Institute For Biological Studies | Use of tam receptor inhibitors as immunoenhancers and tam activators as immunosuppressors |
| CN101918452A (zh) | 2007-11-15 | 2010-12-15 | 中外制药株式会社 | 与Anexelekto结合的单克隆抗体及其利用 |
| HRP20170317T1 (hr) | 2008-02-15 | 2017-04-21 | Rigel Pharmaceuticals, Inc. | Spojevi pirimidin-2-amina i njihova uporaba kao inhibitora jak kinaza |
| CA2730231C (en) | 2008-07-09 | 2016-10-18 | Rigel Pharmaceuticals, Inc. | Polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CA2730251C (en) | 2008-07-09 | 2016-08-09 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| JP4644273B2 (ja) * | 2008-07-15 | 2011-03-02 | 本田技研工業株式会社 | 車両周辺監視装置 |
| AU2009330821B2 (en) * | 2008-12-24 | 2015-06-11 | Bial - Portela & Ca, S.A. | Pharmaceutical compounds |
| BRPI1007046B1 (pt) | 2009-01-16 | 2019-07-16 | Rigel Pharmaceuticals, Inc. | Inibidores axl para uso em terapia de combinação para evitar, tratar ou controlar o câncer metastático. |
| US12221653B2 (en) | 2010-05-18 | 2025-02-11 | Natera, Inc. | Methods for simultaneous amplification of target loci |
| US11339429B2 (en) | 2010-05-18 | 2022-05-24 | Natera, Inc. | Methods for non-invasive prenatal ploidy calling |
| US11326208B2 (en) | 2010-05-18 | 2022-05-10 | Natera, Inc. | Methods for nested PCR amplification of cell-free DNA |
| US11332793B2 (en) | 2010-05-18 | 2022-05-17 | Natera, Inc. | Methods for simultaneous amplification of target loci |
| US11322224B2 (en) | 2010-05-18 | 2022-05-03 | Natera, Inc. | Methods for non-invasive prenatal ploidy calling |
| US11408031B2 (en) | 2010-05-18 | 2022-08-09 | Natera, Inc. | Methods for non-invasive prenatal paternity testing |
| US11939634B2 (en) | 2010-05-18 | 2024-03-26 | Natera, Inc. | Methods for simultaneous amplification of target loci |
| US9677118B2 (en) | 2014-04-21 | 2017-06-13 | Natera, Inc. | Methods for simultaneous amplification of target loci |
| US10316362B2 (en) | 2010-05-18 | 2019-06-11 | Natera, Inc. | Methods for simultaneous amplification of target loci |
| EP2854058A3 (en) | 2010-05-18 | 2015-10-28 | Natera, Inc. | Methods for non-invasive pre-natal ploidy calling |
| US20190010543A1 (en) | 2010-05-18 | 2019-01-10 | Natera, Inc. | Methods for simultaneous amplification of target loci |
| US12152275B2 (en) | 2010-05-18 | 2024-11-26 | Natera, Inc. | Methods for non-invasive prenatal ploidy calling |
| US11332785B2 (en) | 2010-05-18 | 2022-05-17 | Natera, Inc. | Methods for non-invasive prenatal ploidy calling |
| AU2011348100B2 (en) | 2010-12-22 | 2016-08-25 | Natera, Inc. | Methods for non-invasive prenatal paternity testing |
| JP6153874B2 (ja) | 2011-02-09 | 2017-06-28 | ナテラ， インコーポレイテッド | 非侵襲的出生前倍数性呼び出しのための方法 |
| SG11201404505PA (en) | 2012-01-31 | 2014-10-30 | Daiichi Sankyo Co Ltd | Pyridone derivative |
| US20140010783A1 (en) * | 2012-07-06 | 2014-01-09 | Hoffmann-La Roche Inc. | Antiviral compounds |
| WO2014018535A1 (en) | 2012-07-25 | 2014-01-30 | Salk Institute For Biological Studies | Regulating the interaction between tam ligands and lipid membranes with exposed phosphatidylserine |
| US20140100126A1 (en) | 2012-08-17 | 2014-04-10 | Natera, Inc. | Method for Non-Invasive Prenatal Testing Using Parental Mosaicism Data |
| MX2015009176A (es) * | 2013-01-23 | 2015-11-09 | Hoffmann La Roche | Derivados de triazola antivirales. |
| AU2014353006B2 (en) | 2013-11-20 | 2019-04-04 | Signalchem Life Sciences Corp. | Quinazoline derivatives as TAM family kinase inhibitors |
| JP6496731B2 (ja) | 2013-11-27 | 2019-04-03 | シグナルケム・ライフサイエンシーズ・コーポレイションＳｉｇｎａｌｃｈｅｍ Ｌｉｆｅｓｃｉｅｎｃｅｓ Ｃｏｒｐｏｒａｔｉｏｎ | Ｔａｍファミリーキナーゼ阻害剤としてのアミノピリジン誘導体 |
| US20150252370A1 (en) * | 2014-03-04 | 2015-09-10 | Academia Sinica | Use of atx inhibitors for treatment or prevention of influenza virus a infections |
| RU2717641C2 (ru) | 2014-04-21 | 2020-03-24 | Натера, Инк. | Обнаружение мутаций и плоидности в хромосомных сегментах |
| US20180173845A1 (en) | 2014-06-05 | 2018-06-21 | Natera, Inc. | Systems and Methods for Detection of Aneuploidy |
| TWI723572B (zh) | 2014-07-07 | 2021-04-01 | 日商第一三共股份有限公司 | 具有四氫吡喃基甲基之吡啶酮衍生物及其用途 |
| EP4428863A3 (en) | 2015-05-11 | 2024-12-11 | Natera, Inc. | Methods and compositions for determining ploidy |
| GB201509338D0 (en) | 2015-05-29 | 2015-07-15 | Bergenbio As | Combination therapy |
| ES2896079T3 (es) | 2016-02-26 | 2022-02-23 | Ono Pharmaceutical Co | Fármaco para la terapia del cáncer, caracterizado por la administración de la combinación entre un inhibidor de Axl y un inhibidor del punto de control inmunitario |
| JP7280044B2 (ja) | 2016-04-15 | 2023-05-23 | ナテラ， インコーポレイテッド | 肺癌の検出方法 |
| WO2018067517A1 (en) | 2016-10-04 | 2018-04-12 | Natera, Inc. | Methods for characterizing copy number variation using proximity-litigation sequencing |
| GB201618485D0 (en) | 2016-11-02 | 2016-12-14 | Ucl Business Plc | Method of detecting tumour recurrence |
| US10011870B2 (en) | 2016-12-07 | 2018-07-03 | Natera, Inc. | Compositions and methods for identifying nucleic acid molecules |
| EP3673907A4 (en) | 2017-08-23 | 2020-08-19 | ONO Pharmaceutical Co., Ltd. | CANCER TREATMENT PHARMACEUTICAL INCLUDING AX1 INHIBITOR AS AN EFFECTIVE INGREDIENT |
| US11826363B2 (en) | 2017-10-13 | 2023-11-28 | Ono Pharmaceutical Co., Ltd. | Therapeutic agent for solid cancers, which comprises Axl inhibitor as active ingredient |
| WO2019118926A1 (en) | 2017-12-14 | 2019-06-20 | Tai Diagnostics, Inc. | Assessing graft suitability for transplantation |
| EP3737773B1 (en) | 2018-01-12 | 2023-04-12 | Natera, Inc. | Novel primers and uses thereof |
| DK3781714T3 (da) | 2018-04-14 | 2026-03-30 | Natera Inc | Fremgangsmåder til cancerpåvisning og -overvågning ved personlig påvisning af cirkulerende tumor-dna |
| US12234509B2 (en) | 2018-07-03 | 2025-02-25 | Natera, Inc. | Methods for detection of donor-derived cell-free DNA |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| EP4617383A3 (en) | 2018-12-17 | 2025-12-24 | Natera, Inc. | Methods for analysis of circulating cells |
| WO2020168197A1 (en) | 2019-02-15 | 2020-08-20 | Incyte Corporation | Pyrrolo[2,3-d]pyrimidinone compounds as cdk2 inhibitors |
| TW202100520A (zh) | 2019-03-05 | 2021-01-01 | 美商英塞特公司 | 作為cdk2 抑制劑之吡唑基嘧啶基胺化合物 |
| CA3129665A1 (en) | 2019-03-21 | 2020-09-24 | Onxeo | A dbait molecule in combination with kinase inhibitor for the treatment of cancer |
| US11919904B2 (en) | 2019-03-29 | 2024-03-05 | Incyte Corporation | Sulfonylamide compounds as CDK2 inhibitors |
| WO2020223558A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | Tricyclic amine compounds as cdk2 inhibitors |
| WO2020223469A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | N-(1-(methylsulfonyl)piperidin-4-yl)-4,5-di hydro-1h-imidazo[4,5-h]quinazolin-8-amine derivatives and related compounds as cyclin-dependent kinase 2 (cdk2) inhibitors for treating cancer |
| US12305235B2 (en) | 2019-06-06 | 2025-05-20 | Natera, Inc. | Methods for detecting immune cell DNA and monitoring immune system |
| WO2021030537A1 (en) | 2019-08-14 | 2021-02-18 | Incyte Corporation | Imidazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| GB201912059D0 (en) | 2019-08-22 | 2019-10-09 | Bergenbio As | Combaination therapy of a patient subgroup |
| CR20220170A (es) | 2019-10-11 | 2022-10-10 | Incyte Corp | Aminas bicíclicas como inhibidoras de la cdk2 |
| KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| GB202004189D0 (en) | 2020-03-23 | 2020-05-06 | Bergenbio As | Combination therapy |
| WO2021204713A1 (en) | 2020-04-08 | 2021-10-14 | Bergenbio Asa | Axl inhibitors for antiviral therapy |
| GB202006072D0 (en) | 2020-04-24 | 2020-06-10 | Bergenbio Asa | Method of selecting patients for treatment with cmbination therapy |
| GB202104037D0 (en) | 2021-03-23 | 2021-05-05 | Bergenbio Asa | Combination therapy |
| AU2022261868A1 (en) | 2021-04-22 | 2023-10-26 | Natera, Inc. | Methods for determining velocity of tumor growth |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| CN118076750A (zh) | 2021-08-02 | 2024-05-24 | 纳特拉公司 | 用于检测孕妇体内的赘生物的方法 |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| JP2025502843A (ja) | 2022-01-04 | 2025-01-28 | ナテラ， インコーポレイテッド | がん検出及びモニタリングのための方法 |
| GB202209285D0 (en) | 2022-06-24 | 2022-08-10 | Bergenbio Asa | Dosage regimen for AXL inhibitor |
| WO2024051667A1 (zh) * | 2022-09-05 | 2024-03-14 | 南京正大天晴制药有限公司 | 具有axl抑制活性的取代三唑化合物 |
| US20260069610A1 (en) | 2022-09-09 | 2026-03-12 | University Of Rochester | Inhibition of efferocytosis as a treatment to prevent bone loss and increase bone density and strength |
| CN121039109A (zh) * | 2023-04-18 | 2025-11-28 | 国家科学研究中心 | 3,5-二氨基三唑衍生物及其用于治疗眼部疾病的用途 |
| CN119504619B (zh) * | 2024-10-10 | 2026-02-17 | 江苏省农业科学院 | 具有抗真菌活性的化合物及其制备方法和应用 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1403866A (en) | 1971-12-06 | 1975-08-28 | Wyeth John & Brother Ltd | Derivatives of 3-amino-1,2,4-triazoles |
| JPH07101942A (ja) * | 1993-07-23 | 1995-04-18 | Green Cross Corp:The | 新規トリアゾール誘導体 |
| EP0710654A4 (en) | 1993-07-23 | 1996-08-28 | Green Cross Corp | TRIAZOLE DERIVATIVE AND ITS PHARMACEUTICAL USE |
| GB9918180D0 (en) * | 1999-08-02 | 1999-10-06 | Smithkline Beecham Plc | Novel compositions |
| NZ526624A (en) | 2000-12-22 | 2005-07-29 | Ortho Mcneil Pharm Inc | Substituted triazole diamine derivatives as kinase inhibitors |
| TW201041580A (en) | 2001-09-27 | 2010-12-01 | Alcon Inc | Inhibitors of glycogen synthase kinase-3 (GSK-3) for treating glaucoma |
| MXPA04010778A (es) | 2002-05-03 | 2005-03-07 | Janssen Pharmaceutica Nv | Microemulsiones polimericas. |
| US20060293256A1 (en) | 2002-08-06 | 2006-12-28 | Masateru Yamada | Remedy or preventive for kidney disease and method of diagnosing kidney disease |
| EP1563094A4 (en) | 2002-10-29 | 2007-04-25 | Rigel Pharmaceuticals Inc | MODULATORS OF ANGIOGENESIS AND TUMORIGENESIS |
| AR042052A1 (es) | 2002-11-15 | 2005-06-08 | Vertex Pharma | Diaminotriazoles utiles como inhibidores de proteinquinasas |
| ATE455546T1 (de) | 2003-08-06 | 2010-02-15 | Vertex Pharma | Aminotriazol-verbindungen als proteinkinase- hemmer |
| WO2005077922A2 (en) * | 2004-02-11 | 2005-08-25 | Janssen Pharmaceutica, N.V. | Process for the preparation of substituted triazole compounds |
| ES2406930T3 (es) | 2006-12-29 | 2013-06-10 | Rigel Pharmaceuticals, Inc. | Triazoles sustituidos con arilo bicíclico y heteroarilo bicíclico útiles como inhibidores de AXL |
| CA2710230C (en) | 2006-12-29 | 2016-02-23 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic aryl and bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CN101622248B (zh) | 2006-12-29 | 2013-04-17 | 里格尔制药公司 | 用作axl抑制剂的n3-杂芳基取代的三唑和n5-杂芳基取代的三唑 |
| CA2710051C (en) | 2006-12-29 | 2017-05-16 | Rigel Pharmaceuticals, Inc. | Substituted triazoles useful as axl inhibitors |
| RS53281B (sr) | 2006-12-29 | 2014-08-29 | Rigel Pharmaceuticals Inc. | Policiklični heteroaril supstituisani triazoli koji su korisni kao axl inhibitori |
| BRPI0813356A2 (pt) | 2007-06-15 | 2014-12-30 | Irm Llc | Inibidores de proteína quinase e métodos para uso dos mesmos |
| CA2704052C (en) | 2007-10-26 | 2015-04-21 | Rigel Pharmaceuticals, Inc. | Polycyclic aryl substituted triazoles and polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CA2730251C (en) | 2008-07-09 | 2016-08-09 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CA2730231C (en) | 2008-07-09 | 2016-10-18 | Rigel Pharmaceuticals, Inc. | Polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
| BRPI1007046B1 (pt) | 2009-01-16 | 2019-07-16 | Rigel Pharmaceuticals, Inc. | Inibidores axl para uso em terapia de combinação para evitar, tratar ou controlar o câncer metastático. |
-
2006
- 2006-09-07 CA CA2621503A patent/CA2621503C/en not_active Expired - Fee Related
- 2006-09-07 JP JP2008530213A patent/JP2009507080A/ja active Pending
- 2006-09-07 EP EP20060814315 patent/EP1922310A2/en not_active Withdrawn
- 2006-09-07 WO PCT/US2006/034970 patent/WO2007030680A2/en not_active Ceased
- 2006-09-07 US US11/518,550 patent/US7884119B2/en active Active
-
2010
- 2010-12-10 US US12/965,545 patent/US8389557B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6583141B1 (en) | 4,5-dihydro-isoxazole derivatives and their pharmaceutical use | |
| US5496833A (en) | Piperidine tachykinin receptor antagonists | |
| US7884119B2 (en) | Triazole derivatives useful as Axl inhibitors | |
| CA2484188C (en) | Tachykinin receptor antagonists | |
| CA2483159C (en) | Triazole derivatives as tachykinin receptor antagonists | |
| RU2006130683A (ru) | Производные 3-замещенного 1, 5-дифенилпиразола, полезные в качестве св1 модуляторов | |
| CA2312720A1 (en) | Retinoic acid mimetic anilides | |
| DK2576543T3 (en) | Pyrazole compounds as sigma receptor inhibitors | |
| RU2366652C2 (ru) | Амиды аминоалкилзамещенных азетидинов, пирролидинов, пиперидинов и азепанов | |
| KR101683222B1 (ko) | 피페리딘 화합물, 이를 포함하는 약학적 조성물 및 그 용도 | |
| JP2008513500A5 (enExample) | ||
| WO2002040458A1 (en) | Isoxazole derivatives | |
| JP2002516909A5 (enExample) | ||
| WO1993021181A1 (en) | Azacyclic compounds | |
| JP2008509982A5 (enExample) | ||
| WO2009123316A1 (ja) | 複素環誘導体及びその用途 | |
| KR20150023686A (ko) | 네프릴리신 억제제 | |
| KR20050008846A (ko) | 세로토닌 수용체 제제로서의 ｎ-치환된 피페리딘 유도체 | |
| JP2005534627A5 (enExample) | ||
| US8399451B2 (en) | Heterocyclic compounds | |
| JP2005526815A5 (enExample) | ||
| ME02144B (me) | Jedinjenja aril triazola sa antitumorskom aktivnošću | |
| RU2006135482A (ru) | Терапевтические агенты | |
| KR101603487B1 (ko) | 3-치환된 프로판아민 화합물 | |
| RU2006135486A (ru) | Производные n-пиперидина в качестве модуляторов ссr3 |