JP2009507080A - Ａｘｌ阻害剤として有用なトリアゾール誘導体 - Google Patents

Info

Publication number

JP2009507080A

JP2009507080A JP2008530213A JP2008530213A JP2009507080A JP 2009507080 A JP2009507080 A JP 2009507080A JP 2008530213 A JP2008530213 A JP 2008530213A JP 2008530213 A JP2008530213 A JP 2008530213A JP 2009507080 A JP2009507080 A JP 2009507080A

Authority

JP

Japan

Prior art keywords

optionally substituted

amino

group

alkyl

triazole

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.)

Pending

Links

• Espacenet
• Global Dossier
• Discuss

• 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title abstract description 4
• 239000003112 inhibitor Substances 0.000 title description 3
• 201000010099 disease Diseases 0.000 claims abstract description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
• 238000000034 method Methods 0.000 claims abstract description 11
• 230000000694 effects Effects 0.000 claims abstract description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 559
• -1 cyano, nitro, oxo, thioxo, trimethylsilanyl Chemical group 0.000 claims description 385
• 125000001188 haloalkyl group Chemical group 0.000 claims description 378
• 239000001257 hydrogen Substances 0.000 claims description 367
• 229910052739 hydrogen Inorganic materials 0.000 claims description 367
• 125000001072 heteroaryl group Chemical group 0.000 claims description 366
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 356
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 329
• 125000000623 heterocyclic group Chemical group 0.000 claims description 320
• 125000005843 halogen group Chemical group 0.000 claims description 315
• 125000001424 substituent group Chemical group 0.000 claims description 307
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 257
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 222
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 219
• 125000003118 aryl group Chemical group 0.000 claims description 207
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 200
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 176
• 125000003107 substituted aryl group Chemical group 0.000 claims description 170
• 125000002947 alkylene group Chemical group 0.000 claims description 163
• 125000004450 alkenylene group Chemical group 0.000 claims description 159
• 150000001875 compounds Chemical class 0.000 claims description 135
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 128
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 115
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 113
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 107
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 99
• 125000003342 alkenyl group Chemical group 0.000 claims description 96
• 125000000304 alkynyl group Chemical group 0.000 claims description 94
• 125000004043 oxo group Chemical group O=* 0.000 claims description 84
• 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 82
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 79
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 79
• 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 78
• 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 77
• 229910052757 nitrogen Inorganic materials 0.000 claims description 64
• 125000004419 alkynylene group Chemical group 0.000 claims description 58
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 58
• 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 50
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
• PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
• 239000000651 prodrug Substances 0.000 claims description 18
• 229940002612 prodrug Drugs 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 17
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 15
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
• 241000124008 Mammalia Species 0.000 claims description 14
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 10
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 239000000203 mixture Substances 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 239000012453 solvate Substances 0.000 claims description 8
• 206010028980 Neoplasm Diseases 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 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 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 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 description 6
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 201000009273 Endometriosis Diseases 0.000 claims description 4
• 208000002780 macular degeneration Diseases 0.000 claims description 4
• 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims description 3
• 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 description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
• 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 description 3
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
• 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 description 3
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
• 206010014733 Endometrial cancer Diseases 0.000 claims description 3
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 150000001204 N-oxides Chemical class 0.000 claims description 3
• 206010033128 Ovarian cancer Diseases 0.000 claims description 3
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 206010038389 Renal cancer Diseases 0.000 claims description 3
• 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 3
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
• 208000024248 Vascular System injury Diseases 0.000 claims description 3
• 208000012339 Vascular injury Diseases 0.000 claims description 3
• PWIGYBONXWGOQE-UHFFFAOYSA-N alizarin complexone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(CN(CC(O)=O)CC(=O)O)C(O)=C2O PWIGYBONXWGOQE-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
• 201000010982 kidney cancer Diseases 0.000 claims description 3
• 208000017169 kidney disease Diseases 0.000 claims description 3
• 208000025113 myeloid leukemia Diseases 0.000 claims description 3
• 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 description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• 201000002510 thyroid cancer Diseases 0.000 claims description 3
• 208000002177 Cataract Diseases 0.000 claims description 2
• 206010025323 Lymphomas Diseases 0.000 claims description 2
• 206010047571 Visual impairment Diseases 0.000 claims description 2
• 239000000654 additive Substances 0.000 claims description 2
• 239000007788 liquid Substances 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 2
• UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 2
• 201000008482 osteoarthritis Diseases 0.000 claims description 2
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
• 208000019553 vascular disease Diseases 0.000 claims description 2
• 208000029257 vision disease Diseases 0.000 claims description 2
• 230000004393 visual impairment Effects 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 198
• XTMRUJFITBKHKF-UHFFFAOYSA-N O=C=C1NC=NN1 Chemical compound O=C=C1NC=NN1 XTMRUJFITBKHKF-UHFFFAOYSA-N 0.000 claims 9
• 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
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])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
• 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 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
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
• 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
• 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
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
• 230000005740 tumor formation Effects 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
• 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
• 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
• 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
• 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
• 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
• JIWSSFJGSGHESS-UHFFFAOYSA-N 5-amino-n-(3-methoxyphenyl)-3-[4-(2-piperidin-1-ylethoxy)anilino]-1,2,4-triazole-1-carboxamide Chemical compound COC1=CC=CC(NC(=O)N2C(=NC(NC=3C=CC(OCCN4CCCCC4)=CC=3)=N2)N)=C1 JIWSSFJGSGHESS-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
• 201000005969 Uveal melanoma Diseases 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
• GWIJZXSMIBPPJK-UHFFFAOYSA-N [5-amino-3-(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(N)=NC(NC=2C=CC(=CC=2)N2CCCCC2)=N1 GWIJZXSMIBPPJK-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
• CJQSCIOUAXMXTQ-UHFFFAOYSA-N [5-amino-3-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-(4-morpholin-4-ylphenyl)methanone Chemical compound C=1C=C(OCCN2CCCC2)C(OC)=CC=1NC(=N1)N=C(N)N1C(=O)C(C=C1)=CC=C1N1CCOCC1 CJQSCIOUAXMXTQ-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
• 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
• 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
• 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
• VVXKZDOHRSPBKA-UHFFFAOYSA-N [5-amino-3-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,2,4-triazol-1-yl]-pyridin-2-ylmethanone Chemical compound N=1N(C(=O)C=2N=CC=CC=2)C(N)=NC=1NC(C=C1)=CC=C1OCCN1CCCC1 VVXKZDOHRSPBKA-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
• 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
• 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 claims 1
• 230000036571 hydration Effects 0.000 claims 1
• 238000006703 hydration reaction Methods 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
• 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
• JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical compound C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 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
• 230000003197 catalytic effect Effects 0.000 abstract description 4
• 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 abstract description 2
• 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 abstract description 2
• 230000002401 inhibitory effect Effects 0.000 abstract description 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 50
• 125000004432 carbon atom Chemical group C* 0.000 description 24
• 150000003254 radicals Chemical class 0.000 description 17
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
• 208000024891 symptom Diseases 0.000 description 8
• 239000002253 acid Substances 0.000 description 7
• 125000001183 hydrocarbyl group Chemical group 0.000 description 7
• 125000000464 thioxo group Chemical group S=* 0.000 description 7
• 150000001721 carbon Chemical group 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• 239000003446 ligand Substances 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
• 230000033115 angiogenesis Effects 0.000 description 4
• 125000004429 atom Chemical group 0.000 description 4
• RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
• 230000011664 signaling Effects 0.000 description 4
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• 101150022345 GAS6 gene Proteins 0.000 description 3
• 101000807561 Homo sapiens Tyrosine-protein kinase receptor UFO Proteins 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
• 102100037236 Tyrosine-protein kinase receptor UFO Human genes 0.000 description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
• 210000004027 cell Anatomy 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 239000003814 drug Substances 0.000 description 3
• 230000006870 function Effects 0.000 description 3
• 238000001727 in vivo Methods 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• 150000007530 organic bases Chemical class 0.000 description 3
• 125000003367 polycyclic group Chemical group 0.000 description 3
• 235000018102 proteins Nutrition 0.000 description 3
• 102000004169 proteins and genes Human genes 0.000 description 3
• 108090000623 proteins and genes Proteins 0.000 description 3
• 229920006395 saturated elastomer Polymers 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• 150000003852 triazoles Chemical class 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
• QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 description 2
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
• XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 241000282412 Homo Species 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• 102000001253 Protein Kinase Human genes 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 208000007536 Thrombosis Diseases 0.000 description 2
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
• 101150098329 Tyro3 gene Proteins 0.000 description 2
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
• 206010064930 age-related macular degeneration Diseases 0.000 description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 235000001014 amino acid Nutrition 0.000 description 2
• 150000001413 amino acids Chemical class 0.000 description 2
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
• 125000004104 aryloxy group Chemical group 0.000 description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
• 125000002619 bicyclic group Chemical group 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 229960001948 caffeine Drugs 0.000 description 2
• VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
• 239000011575 calcium Substances 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 125000003636 chemical group Chemical group 0.000 description 2
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
• 229960001231 choline Drugs 0.000 description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
• GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
• 238000010586 diagram Methods 0.000 description 2
• JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
• 210000002889 endothelial cell Anatomy 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 230000014509 gene expression Effects 0.000 description 2
• KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
• 229940093915 gynecological organic acid Drugs 0.000 description 2
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 2
• 150000007529 inorganic bases Chemical class 0.000 description 2
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 244000144972 livestock Species 0.000 description 2
• 201000001441 melanoma Diseases 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
• WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• 239000001301 oxygen Chemical group 0.000 description 2
• 239000000546 pharmaceutical excipient Substances 0.000 description 2
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
• 230000035790 physiological processes and functions Effects 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• 108060006633 protein kinase Proteins 0.000 description 2
• 125000000168 pyrrolyl group Chemical group 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 229910052717 sulfur Chemical group 0.000 description 2
• 239000011593 sulfur Chemical group 0.000 description 2
• 125000004434 sulfur atom Chemical group 0.000 description 2
• YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
• 125000003396 thiol group Chemical group [H]S* 0.000 description 2
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 125000001425 triazolyl group Chemical group 0.000 description 2
• 230000004614 tumor growth Effects 0.000 description 2
• 210000004509 vascular smooth muscle cell Anatomy 0.000 description 2
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 description 1
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
• 125000005877 1,4-benzodioxanyl group Chemical group 0.000 description 1
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
• SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
• RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
• 125000005987 1-oxo-thiomorpholinyl group Chemical group 0.000 description 1
• FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
• SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
• MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
• BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
• 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
• 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000006088 2-oxoazepinyl group Chemical group 0.000 description 1
• KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
• 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 description 1
• 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
• 125000005986 4-piperidonyl group Chemical group 0.000 description 1
• ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical class NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 201000004569 Blindness Diseases 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• 241000283707 Capra Species 0.000 description 1
• 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
• 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
• AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 208000007342 Diabetic Nephropathies Diseases 0.000 description 1
• 239000004097 EU approved flavor enhancer Substances 0.000 description 1
• 241000283086 Equidae Species 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 102000002090 Fibronectin type III Human genes 0.000 description 1
• 108050009401 Fibronectin type III Proteins 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
• IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
• 206010018364 Glomerulonephritis Diseases 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• 102100031487 Growth arrest-specific protein 6 Human genes 0.000 description 1
• 101000650322 Homo sapiens E3 ubiquitin-protein ligase Arkadia Proteins 0.000 description 1
• 101000923005 Homo sapiens Growth arrest-specific protein 6 Proteins 0.000 description 1
• 108060003951 Immunoglobulin Proteins 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• 239000005639 Lauric acid Substances 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
• HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• 102000005608 Neuronal Cell Adhesion Molecules Human genes 0.000 description 1
• 108010059604 Neuronal Cell Adhesion Molecules Proteins 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 235000021314 Palmitic acid Nutrition 0.000 description 1
• 208000031481 Pathologic Constriction Diseases 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• 229940096437 Protein S Drugs 0.000 description 1
• 102000029301 Protein S Human genes 0.000 description 1
• 108010066124 Protein S Proteins 0.000 description 1
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
• ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 206010041067 Small cell lung cancer Diseases 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 241000282887 Suidae Species 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
• 108010067390 Viral Proteins Proteins 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
• 229910001573 adamantine Inorganic materials 0.000 description 1
• 235000011037 adipic acid Nutrition 0.000 description 1
• 239000001361 adipic acid Substances 0.000 description 1
• 229960000250 adipic acid Drugs 0.000 description 1
• 239000002671 adjuvant Substances 0.000 description 1
• 230000002776 aggregation Effects 0.000 description 1
• 238000004220 aggregation Methods 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 230000008850 allosteric inhibition Effects 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 229960004909 aminosalicylic acid Drugs 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
• 230000006907 apoptotic process Effects 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 229960003121 arginine Drugs 0.000 description 1
• 125000005015 aryl alkynyl group Chemical group 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 229960005261 aspartic acid Drugs 0.000 description 1
• 238000003556 assay Methods 0.000 description 1
• 125000002785 azepinyl group Chemical group 0.000 description 1
• 230000004888 barrier function Effects 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000005870 benzindolyl group Chemical group 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• 125000005875 benzo[b][1,4]dioxepinyl group Chemical group 0.000 description 1
• 125000005876 benzo[b][1,4]oxazinyl group Chemical group 0.000 description 1
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 229960004365 benzoic acid Drugs 0.000 description 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
• 125000005878 benzonaphthofuranyl group Chemical group 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
• 229960003237 betaine Drugs 0.000 description 1
• 230000000975 bioactive effect Effects 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 230000023555 blood coagulation Effects 0.000 description 1
• 230000036770 blood supply Effects 0.000 description 1
• 210000000069 breast epithelial cell Anatomy 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
• 210000004899 c-terminal region Anatomy 0.000 description 1
• LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
• KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 238000000423 cell based assay Methods 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 230000024245 cell differentiation Effects 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 230000017455 cell-cell adhesion Effects 0.000 description 1
• 239000012069 chiral reagent Substances 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 210000001612 chondrocyte Anatomy 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 230000006957 competitive inhibition Effects 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 230000001086 cytosolic effect Effects 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 125000005507 decahydroisoquinolyl group Chemical group 0.000 description 1
• 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• 208000033679 diabetic kidney disease Diseases 0.000 description 1
• 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 150000004683 dihydrates Chemical class 0.000 description 1
• 238000006471 dimerization reaction Methods 0.000 description 1
• 125000005879 dioxolanyl group Chemical group 0.000 description 1
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 239000003937 drug carrier Substances 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 239000000975 dye Substances 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
• 125000001153 fluoro group Chemical group F* 0.000 description 1
• 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• 235000019264 food flavour enhancer Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 238000005755 formation reaction Methods 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 125000003844 furanonyl group Chemical group 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
• 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
• 229960005219 gentisic acid Drugs 0.000 description 1
• 239000000174 gluconic acid Substances 0.000 description 1
• 235000012208 gluconic acid Nutrition 0.000 description 1
• 229960002442 glucosamine Drugs 0.000 description 1
• 229940097043 glucuronic acid Drugs 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• 230000012010 growth Effects 0.000 description 1
• 125000005980 hexynyl group Chemical group 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
• 229960002885 histidine Drugs 0.000 description 1
• 235000003642 hunger Nutrition 0.000 description 1
• XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 125000005020 hydroxyalkenyl group Chemical group 0.000 description 1
• 125000005016 hydroxyalkynyl group Chemical group 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 102000018358 immunoglobulin Human genes 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• 108020001756 ligand binding domains Proteins 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 229960003646 lysine Drugs 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 230000009401 metastasis Effects 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• 230000005012 migration Effects 0.000 description 1
• 238000013508 migration Methods 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 150000004682 monohydrates Chemical class 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 230000009826 neoplastic cell growth Effects 0.000 description 1
• 210000002569 neuron Anatomy 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 229960003512 nicotinic acid Drugs 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
• 239000002773 nucleotide Substances 0.000 description 1
• 125000003729 nucleotide group Chemical group 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 description 1
• 125000005061 octahydroisoindolyl group Chemical group C1(NCC2CCCCC12)* 0.000 description 1
• 229960002446 octanoic acid Drugs 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 229960002969 oleic acid Drugs 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 229960005010 orotic acid Drugs 0.000 description 1
• 230000002018 overexpression Effects 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 229940116315 oxalic acid Drugs 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 229940098695 palmitic acid Drugs 0.000 description 1
• WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 230000001575 pathological effect Effects 0.000 description 1
• 230000007170 pathology Effects 0.000 description 1
• 235000019371 penicillin G benzathine Nutrition 0.000 description 1
• 125000005981 pentynyl group Chemical group 0.000 description 1
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
• 230000004962 physiological condition Effects 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 150000003141 primary amines Chemical class 0.000 description 1
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
• 229960004919 procaine Drugs 0.000 description 1
• 125000006410 propenylene group Chemical group 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 108091008598 receptor tyrosine kinases Proteins 0.000 description 1
• 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 230000000306 recurrent effect Effects 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 230000001850 reproductive effect Effects 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 125000006413 ring segment Chemical group 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 229940116353 sebacic acid Drugs 0.000 description 1
• 210000000717 sertoli cell Anatomy 0.000 description 1
• 210000002966 serum Anatomy 0.000 description 1
• 208000000587 small cell lung carcinoma Diseases 0.000 description 1
• AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 238000003797 solvolysis reaction Methods 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 230000037351 starvation Effects 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 229960004274 stearic acid Drugs 0.000 description 1
• 230000036262 stenosis Effects 0.000 description 1
• 208000037804 stenosis Diseases 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 229960001367 tartaric acid Drugs 0.000 description 1
• 150000004685 tetrahydrates Chemical class 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
• 229960004559 theobromine Drugs 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000005985 thienyl[1,3]dithianyl group Chemical group 0.000 description 1
• 230000001131 transforming effect Effects 0.000 description 1
• 238000002054 transplantation Methods 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• 150000004684 trihydrates Chemical class 0.000 description 1
• YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 125000005455 trithianyl group Chemical group 0.000 description 1
• 229960004418 trolamine Drugs 0.000 description 1
• 229960000281 trometamol Drugs 0.000 description 1
• 210000004881 tumor cell Anatomy 0.000 description 1
• 229960002703 undecylenic acid Drugs 0.000 description 1
• 210000003556 vascular endothelial cell Anatomy 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 230000007998 vessel formation Effects 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 230000029663 wound healing Effects 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1