CA2621503C - Triazole derivatives useful as axl inhibitors - Google Patents

Info

Publication number

CA2621503C

CA2621503C CA2621503A CA2621503A CA2621503C CA 2621503 C CA2621503 C CA 2621503C CA 2621503 A CA2621503 A CA 2621503A CA 2621503 A CA2621503 A CA 2621503A CA 2621503 C CA2621503 C CA 2621503C

Authority

CA

Canada

Prior art keywords

optionally substituted

group

amino

triazole

phenylamino

Prior art date

2005-09-07

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.)

Expired - Fee Related

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• 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title abstract description 6
• 239000003112 inhibitor Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 268
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
• -1 2-(pyrrolidin-1-yl)ethyl Chemical group 0.000 claims description 447
• 125000001188 haloalkyl group Chemical group 0.000 claims description 393
• 125000001424 substituent group Chemical group 0.000 claims description 385
• 125000001072 heteroaryl group Chemical group 0.000 claims description 381
• 239000001257 hydrogen Substances 0.000 claims description 355
• 229910052739 hydrogen Inorganic materials 0.000 claims description 355
• 125000000623 heterocyclic group Chemical group 0.000 claims description 329
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 307
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 280
• 150000002431 hydrogen Chemical group 0.000 claims description 275
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 239
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 210
• 125000003107 substituted aryl group Chemical group 0.000 claims description 208
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 199
• 125000002947 alkylene group Chemical group 0.000 claims description 188
• 125000004450 alkenylene group Chemical group 0.000 claims description 183
• 125000003118 aryl group Chemical group 0.000 claims description 178
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 178
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 165
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 152
• 125000000217 alkyl group Chemical group 0.000 claims description 127
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 123
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 93
• 125000003342 alkenyl group Chemical group 0.000 claims description 90
• 125000000304 alkynyl group Chemical group 0.000 claims description 89
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 81
• 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 81
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 80
• 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 80
• 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 80
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 80
• 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 79
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 77
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 76
• 125000004419 alkynylene group Chemical group 0.000 claims description 67
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 44
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 239000000203 mixture Substances 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 19
• KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 150000001204 N-oxides Chemical class 0.000 claims description 4
• 125000001475 halogen functional group Chemical group 0.000 claims 44
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• VGWPIIJLYJCPRW-UHFFFAOYSA-N [5-amino-3-[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(N)=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=N1 VGWPIIJLYJCPRW-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
• 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
• NJDPZQPHBBSKSH-UHFFFAOYSA-N [5-amino-3-[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=C1)=CC=C1OCCN1CCCC1 NJDPZQPHBBSKSH-UHFFFAOYSA-N 0.000 claims 1
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