HRP20010473A2 - Combination chemotherapy - Google Patents

Info

Publication number

HRP20010473A2

HRP20010473A2 HR20010473A HRP20010473A HRP20010473A2 HR P20010473 A2 HRP20010473 A2 HR P20010473A2 HR 20010473 A HR20010473 A HR 20010473A HR P20010473 A HRP20010473 A HR P20010473A HR P20010473 A2 HRP20010473 A2 HR P20010473A2

Authority

HR

Croatia

Prior art keywords

methyl

phenylamino

iodo

benzamide

difluoro

Prior art date

1998-12-22

Links

• Espacenet
• Global Dossier
• Discuss

• 238000009096 combination chemotherapy Methods 0.000 title 1
• -1 aryl heteroaryl Chemical group 0.000 claims description 164
• 229940124647 MEK inhibitor Drugs 0.000 claims description 63
• 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims description 63
• 239000003112 inhibitor Substances 0.000 claims description 55
• 230000011278 mitosis Effects 0.000 claims description 44
• 238000000034 method Methods 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 239000001257 hydrogen Substances 0.000 claims description 35
• 229930012538 Paclitaxel Natural products 0.000 claims description 33
• 229960001592 paclitaxel Drugs 0.000 claims description 33
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 33
• 150000002431 hydrogen Chemical class 0.000 claims description 23
• 125000000217 alkyl group Chemical group 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 206010028980 Neoplasm Diseases 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 17
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 239000000460 chlorine Substances 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
• 201000011510 cancer Diseases 0.000 claims description 14
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000003282 alkyl amino group Chemical group 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 150000001408 amides Chemical class 0.000 claims description 10
• 150000002148 esters Chemical class 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• GFMMXOIFOQCCGU-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-N-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 GFMMXOIFOQCCGU-UHFFFAOYSA-N 0.000 claims description 8
• HSDBAZASWXUUHX-UHFFFAOYSA-N 4-fluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NO HSDBAZASWXUUHX-UHFFFAOYSA-N 0.000 claims description 8
• 102100031480 Dual specificity mitogen-activated protein kinase kinase 1 Human genes 0.000 claims description 8
• 101710146526 Dual specificity mitogen-activated protein kinase kinase 1 Proteins 0.000 claims description 8
• 102100023266 Dual specificity mitogen-activated protein kinase kinase 2 Human genes 0.000 claims description 8
• 101710146529 Dual specificity mitogen-activated protein kinase kinase 2 Proteins 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 229960003668 docetaxel Drugs 0.000 claims description 8
• 239000011737 fluorine Substances 0.000 claims description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 229940002612 prodrug Drugs 0.000 claims description 8
• 239000000651 prodrug Substances 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• VJNZMSLGVUSPCF-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-n-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C1CC1CONC(=O)C=1C=C(Br)C(F)=C(F)C=1NC1=CC=C(I)C=C1Cl VJNZMSLGVUSPCF-UHFFFAOYSA-N 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims description 7
• 229960004528 vincristine Drugs 0.000 claims description 7
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 claims description 7
• IPJAGDMRFVGHCN-UHFFFAOYSA-N 5-bromo-3,4-difluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NO IPJAGDMRFVGHCN-UHFFFAOYSA-N 0.000 claims description 6
• CLOSFYSFDCNULT-UHFFFAOYSA-N 5-iodo-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(=O)NOCC1=CC=CC=C1 CLOSFYSFDCNULT-UHFFFAOYSA-N 0.000 claims description 6
• JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 229960003048 vinblastine Drugs 0.000 claims description 6
• JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 6
• 229960002066 vinorelbine Drugs 0.000 claims description 6
• SRMDAFUJVQJZFI-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl SRMDAFUJVQJZFI-UHFFFAOYSA-N 0.000 claims description 5
• 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 claims description 5
• 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 claims description 5
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• BZSLAYDTMNXEOY-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-4-fluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1Cl BZSLAYDTMNXEOY-UHFFFAOYSA-N 0.000 claims description 4
• JUVFXZWQSKISCB-UHFFFAOYSA-N 5-bromo-n-(cyclopropylmethoxy)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1CC1 JUVFXZWQSKISCB-UHFFFAOYSA-N 0.000 claims description 4
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 4
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
• ROCRLSIAQQGIPN-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-(cyclobutylmethoxy)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CCC1 ROCRLSIAQQGIPN-UHFFFAOYSA-N 0.000 claims description 3
• UDMYBSQMRDBEIC-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-hydroxyethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCO UDMYBSQMRDBEIC-UHFFFAOYSA-N 0.000 claims description 3
• ILYBIGUHBUIMMX-UHFFFAOYSA-N 3,4-difluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NO ILYBIGUHBUIMMX-UHFFFAOYSA-N 0.000 claims description 3
• WBQVEORRHAMIPY-UHFFFAOYSA-N 5-bromo-n-(cyclobutylmethoxy)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1CCC1 WBQVEORRHAMIPY-UHFFFAOYSA-N 0.000 claims description 3
• HXACAYXLBFGWMG-UHFFFAOYSA-N 5-bromo-n-ethoxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C HXACAYXLBFGWMG-UHFFFAOYSA-N 0.000 claims description 3
• IHNKPBIVPDAOMS-UHFFFAOYSA-N 5-chloro-n-(3-hydroxypropyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCCO IHNKPBIVPDAOMS-UHFFFAOYSA-N 0.000 claims description 3
• NADMNUUKFZOEHQ-UHFFFAOYSA-N COC1=C(C=CC(=C1NC2=C(C=C(C=C2)I)Cl)C(=O)NC3CC3)F Chemical compound COC1=C(C=CC(=C1NC2=C(C=C(C=C2)I)Cl)C(=O)NC3CC3)F NADMNUUKFZOEHQ-UHFFFAOYSA-N 0.000 claims description 3
• QAFJIVFPYARMAT-UHFFFAOYSA-N [5-bromo-2-(4-iodo-2-methylanilino)phenyl]methanol Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1CO QAFJIVFPYARMAT-UHFFFAOYSA-N 0.000 claims description 3
• KARCBUCWSFRWNA-UHFFFAOYSA-N [5-chloro-2-(4-iodo-2-methylanilino)phenyl]methanol Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1CO KARCBUCWSFRWNA-UHFFFAOYSA-N 0.000 claims description 3
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• PINUTQQQUYREAM-UHFFFAOYSA-N n,n-diethyl-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)C(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C PINUTQQQUYREAM-UHFFFAOYSA-N 0.000 claims description 3
• AZTURQUTRYVAEY-UHFFFAOYSA-N n-(2,3-dihydroxypropyl)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCC(O)CO AZTURQUTRYVAEY-UHFFFAOYSA-N 0.000 claims description 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
• RDTSNRQFNRNSCU-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-n-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Br)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 RDTSNRQFNRNSCU-UHFFFAOYSA-N 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• FVMKNRIUORTHMN-UHFFFAOYSA-N 5-chloro-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1F FVMKNRIUORTHMN-UHFFFAOYSA-N 0.000 claims description 2
• FUISGEKSDHFZAN-UHFFFAOYSA-N 5-chloro-n-(cyclopropylmethoxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound FC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Cl)C=C1C(=O)NOCC1CC1 FUISGEKSDHFZAN-UHFFFAOYSA-N 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
• 239000012635 anticancer drug combination Substances 0.000 claims 4
• 229940046044 combinations of antineoplastic agent Drugs 0.000 claims 4
• GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 claims 3
• HSGXTSFMJJMFLA-UHFFFAOYSA-N 2-(2-amino-3-methylphenyl)chromen-4-one Chemical group CC1=CC=CC(C=2OC3=CC=CC=C3C(=O)C=2)=C1N HSGXTSFMJJMFLA-UHFFFAOYSA-N 0.000 claims 1
• YPHIRZRSVJUGDJ-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-cyclopentyloxy-3,4-difluorobenzamide;3,4,5-trifluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C(=O)NO.CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOC1CCCC1 YPHIRZRSVJUGDJ-UHFFFAOYSA-N 0.000 claims 1
• WRVUIVHFBVUINE-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-N-hydroxybenzamide 2-(2-fluoro-4-iodoanilino)-N-hydroxy-4-nitrobenzamide Chemical compound FC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)[N+](=O)[O-].BrC=1C(=C(C(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)Cl)F)F WRVUIVHFBVUINE-UHFFFAOYSA-N 0.000 claims 1
• ULNXZJCDUXUBBY-UHFFFAOYSA-N 5-bromo-N-[3-(dimethylamino)propyl]-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide 4-fluoro-N-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound BrC=1C(=C(C(=C(C(=O)NCCCN(C)C)C1)NC1=C(C=C(C=C1)I)C)F)F.FC1=CC(=C(C(=O)NCCO)C=C1)NC1=C(C=C(C=C1)I)C ULNXZJCDUXUBBY-UHFFFAOYSA-N 0.000 claims 1
• MYXJMTKOGODVJC-UHFFFAOYSA-N 5-chloro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide;5-fluoro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCO.CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCO MYXJMTKOGODVJC-UHFFFAOYSA-N 0.000 claims 1
• URBXTMJFOINPCZ-UHFFFAOYSA-N BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=C(C(=C1F)F)Cl.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=C(C(=C1F)F)F Chemical compound BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=C(C(=C1F)F)Cl.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=C(C(=C1F)F)F URBXTMJFOINPCZ-UHFFFAOYSA-N 0.000 claims 1
• SKMQXQZKZOAOJP-UHFFFAOYSA-N BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1F)F Chemical compound BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1F)F SKMQXQZKZOAOJP-UHFFFAOYSA-N 0.000 claims 1
• FATOFNYONVLPRK-UHFFFAOYSA-N BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=C(C(=C1F)F)Cl.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=C(C(=C1F)F)F Chemical compound BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=C(C(=C1F)F)Cl.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=C(C(=C1F)F)F FATOFNYONVLPRK-UHFFFAOYSA-N 0.000 claims 1
• NJAMRYLSIQKWNE-UHFFFAOYSA-N BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1F)F Chemical compound BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=CC(=C1F)F NJAMRYLSIQKWNE-UHFFFAOYSA-N 0.000 claims 1
• NREFUVGFZLIYAV-UHFFFAOYSA-N BrC1=C(C=CC(=C1)I)NC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-].BrC1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1)F)C.IC1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1)[N+](=O)[O-])C Chemical compound BrC1=C(C=CC(=C1)I)NC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-].BrC1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1)F)C.IC1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC(=C1)[N+](=O)[O-])C NREFUVGFZLIYAV-UHFFFAOYSA-N 0.000 claims 1
• BPANOSLNNSXDIO-UHFFFAOYSA-N BrC=1C(=C(C(=C(C(=O)NCCC2=CC=NC=C2)C1)NC1=C(C=C(C=C1)I)C)F)F.BrC=1C(=C(C(=C(C(=O)NCCN2CCCC2)C1)NC1=C(C=C(C=C1)I)C)F)F Chemical compound BrC=1C(=C(C(=C(C(=O)NCCC2=CC=NC=C2)C1)NC1=C(C=C(C=C1)I)C)F)F.BrC=1C(=C(C(=C(C(=O)NCCN2CCCC2)C1)NC1=C(C=C(C=C1)I)C)F)F BPANOSLNNSXDIO-UHFFFAOYSA-N 0.000 claims 1
• KUFJHSZCAZYYSA-UHFFFAOYSA-N BrC=1C(=C(C(=C(C(=O)NCCO)C1)NC1=C(C=C(C=C1)I)C)F)F.BrC=1C=CC(=C(C(=O)N(C)C)C1)NC1=C(C=C(C=C1)I)C Chemical compound BrC=1C(=C(C(=C(C(=O)NCCO)C1)NC1=C(C=C(C=C1)I)C)F)F.BrC=1C=CC(=C(C(=O)N(C)C)C1)NC1=C(C=C(C=C1)I)C KUFJHSZCAZYYSA-UHFFFAOYSA-N 0.000 claims 1
• DZJDFQYJPXGMBW-UHFFFAOYSA-N BrC=1C(=C(C(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)F)F)F.ClC=1C(=C(C(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)C)F)F Chemical compound BrC=1C(=C(C(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)F)F)F.ClC=1C(=C(C(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)C)F)F DZJDFQYJPXGMBW-UHFFFAOYSA-N 0.000 claims 1
• VRKZGXRTJPVTSW-UHFFFAOYSA-N BrC=1C(=C(C(=C(C(=O)NOCC2CC2)C1)NC1=C(C=C(C=C1)I)F)F)F.ClC=1C(=C(C(=C(C(=O)NOCC2CC2)C1)NC1=C(C=C(C=C1)I)C)F)F Chemical compound BrC=1C(=C(C(=C(C(=O)NOCC2CC2)C1)NC1=C(C=C(C=C1)I)F)F)F.ClC=1C(=C(C(=C(C(=O)NOCC2CC2)C1)NC1=C(C=C(C=C1)I)C)F)F VRKZGXRTJPVTSW-UHFFFAOYSA-N 0.000 claims 1
• YMLHWGZYJPPMRR-UHFFFAOYSA-N BrC=1C(=C(C(=C(C(=O)NOCC=C(C)C)C1)NC1=C(C=C(C=C1)I)C)F)F.BrC=1C(=C(C(=C(C(=O)NOCCCC)C1)NC1=C(C=C(C=C1)I)C)F)F Chemical compound BrC=1C(=C(C(=C(C(=O)NOCC=C(C)C)C1)NC1=C(C=C(C=C1)I)C)F)F.BrC=1C(=C(C(=C(C(=O)NOCCCC)C1)NC1=C(C=C(C=C1)I)C)F)F YMLHWGZYJPPMRR-UHFFFAOYSA-N 0.000 claims 1
• KFGHLCHKPYJCMN-UHFFFAOYSA-N BrC=1C=CC(=C(C(=O)NCC2=CC=C(C=C2)S(N)(=O)=O)C1)NC1=C(C=C(C=C1)I)C.IC=1C=CC(=C(C(=O)NCC2=CC=C(C=C2)S(N)(=O)=O)C1)NC1=C(C=C(C=C1)I)C Chemical compound BrC=1C=CC(=C(C(=O)NCC2=CC=C(C=C2)S(N)(=O)=O)C1)NC1=C(C=C(C=C1)I)C.IC=1C=CC(=C(C(=O)NCC2=CC=C(C=C2)S(N)(=O)=O)C1)NC1=C(C=C(C=C1)I)C KFGHLCHKPYJCMN-UHFFFAOYSA-N 0.000 claims 1
• AOQKQLVXOJVXGN-UHFFFAOYSA-N BrC=1C=CC(=C(C(=O)NCCCN2CCCCC2)C1)NC1=C(C=C(C=C1)I)C.BrC=1C=CC(=C(C(=O)NCCCO)C1)NC1=C(C=C(C=C1)I)C Chemical compound BrC=1C=CC(=C(C(=O)NCCCN2CCCCC2)C1)NC1=C(C=C(C=C1)I)C.BrC=1C=CC(=C(C(=O)NCCCO)C1)NC1=C(C=C(C=C1)I)C AOQKQLVXOJVXGN-UHFFFAOYSA-N 0.000 claims 1
• LXGZYCXMQVRVDR-UHFFFAOYSA-N BrC=1C=CC(=C(C(=O)NCCO)C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NCCC)C=C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NCC(=O)O)C1)NC1=C(C=C(C=C1)I)C Chemical compound BrC=1C=CC(=C(C(=O)NCCO)C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NCCC)C=C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NCC(=O)O)C1)NC1=C(C=C(C=C1)I)C LXGZYCXMQVRVDR-UHFFFAOYSA-N 0.000 claims 1
• RFUNYUNHZAYKME-UHFFFAOYSA-N C1(CC1)CONC(C1=C(C(=C(C(=C1)F)F)F)NC1=C(C=C(C=C1)I)F)=O.C1(CC1)CONC(C1=C(C=C(C=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O Chemical compound C1(CC1)CONC(C1=C(C(=C(C(=C1)F)F)F)NC1=C(C=C(C=C1)I)F)=O.C1(CC1)CONC(C1=C(C=C(C=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O RFUNYUNHZAYKME-UHFFFAOYSA-N 0.000 claims 1
• TTXYJRUWBDNCLK-UHFFFAOYSA-N C1(CC1)CONC(C1=C(C=C(C=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)F)=O.BrC=1C(=C(C(=C(C(=O)NOCC2CC2)C1)NC1=C(C=C(C=C1)I)Cl)F)F Chemical compound C1(CC1)CONC(C1=C(C=C(C=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)F)=O.BrC=1C(=C(C(=C(C(=O)NOCC2CC2)C1)NC1=C(C=C(C=C1)I)Cl)F)F TTXYJRUWBDNCLK-UHFFFAOYSA-N 0.000 claims 1
• NFIRGMYOOKTWKF-UHFFFAOYSA-N C1(CC1)NC(C1=C(C=CC(=C1)F)NC1=C(C=C(C=C1)I)C)=O.BrC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C Chemical compound C1(CC1)NC(C1=C(C=CC(=C1)F)NC1=C(C=C(C=C1)I)C)=O.BrC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C NFIRGMYOOKTWKF-UHFFFAOYSA-N 0.000 claims 1
• HDTFVRBDNMSAGV-UHFFFAOYSA-N C1(CC1)NC(C1=C(C=CC(=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O.FC=1C=CC(=C(C(=O)NCC2=CC=C(C=C2)S(N)(=O)=O)C1)NC1=C(C=C(C=C1)I)C Chemical compound C1(CC1)NC(C1=C(C=CC(=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O.FC=1C=CC(=C(C(=O)NCC2=CC=C(C=C2)S(N)(=O)=O)C1)NC1=C(C=C(C=C1)I)C HDTFVRBDNMSAGV-UHFFFAOYSA-N 0.000 claims 1
• WXCXDWRNURPBRU-UHFFFAOYSA-N C=1C=C(I)C=CC=1N(Cl)C1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 Chemical compound C=1C=C(I)C=CC=1N(Cl)C1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 WXCXDWRNURPBRU-UHFFFAOYSA-N 0.000 claims 1
• DNLREKHLBCOMIH-UHFFFAOYSA-N ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)C.BrC=1C(=C(C(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)Br)F)F Chemical compound ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)C.BrC=1C(=C(C(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)Br)F)F DNLREKHLBCOMIH-UHFFFAOYSA-N 0.000 claims 1
• SAHKSTUKOOYEPV-UHFFFAOYSA-N ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)F.FC=1C(=C(C(=O)NO)C=CC1F)NC1=C(C=C(C=C1)I)F Chemical compound ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)F.FC=1C(=C(C(=O)NO)C=CC1F)NC1=C(C=C(C=C1)I)F SAHKSTUKOOYEPV-UHFFFAOYSA-N 0.000 claims 1
• QPHAYFMRZOZDNO-UHFFFAOYSA-N ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC)C=CC(=C1)[N+](=O)[O-].BrC=1C(=C(C(=C(C(=O)NOCC)C1)NC1=C(C=C(C=C1)I)Br)F)F Chemical compound ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC)C=CC(=C1)[N+](=O)[O-].BrC=1C(=C(C(=C(C(=O)NOCC)C1)NC1=C(C=C(C=C1)I)Br)F)F QPHAYFMRZOZDNO-UHFFFAOYSA-N 0.000 claims 1
• CFDROCXDGVHMGT-UHFFFAOYSA-N ClC=1C(=C(C(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)Cl)F)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=C(C(=C1F)F)F Chemical compound ClC=1C(=C(C(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)Cl)F)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=C(C(=C1F)F)F CFDROCXDGVHMGT-UHFFFAOYSA-N 0.000 claims 1
• SKSQEMHMGZOKJR-UHFFFAOYSA-N ClC=1C(=C(C(=C(C(=O)NOCC2CC2)C1)NC1=C(C=C(C=C1)I)Cl)F)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=C(C(=C1F)F)F Chemical compound ClC=1C(=C(C(=C(C(=O)NOCC2CC2)C1)NC1=C(C=C(C=C1)I)Cl)F)F.ClC1=C(C=CC(=C1)I)NC1=C(C(=O)NOCC2CC2)C=C(C(=C1F)F)F SKSQEMHMGZOKJR-UHFFFAOYSA-N 0.000 claims 1
• WNRQWVJMIIJHND-UHFFFAOYSA-N ClC=1C=CC(=C(C(=O)N(C2=CC=CC=C2)C)C1)NC1=C(C=C(C=C1)I)C.BrC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C.C1(CC1)NC(C1=C(C=CC(=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O Chemical compound ClC=1C=CC(=C(C(=O)N(C2=CC=CC=C2)C)C1)NC1=C(C=C(C=C1)I)C.BrC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C.C1(CC1)NC(C1=C(C=CC(=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O WNRQWVJMIIJHND-UHFFFAOYSA-N 0.000 claims 1
• YREBQENZDVFKER-UHFFFAOYSA-N ClC=1C=CC(=C(C(=O)N(CC)CC)C1)NC1=C(C=C(C=C1)I)C.C(CCC)NC(C1=C(C=C(C=C1)F)NC1=C(C=C(C=C1)I)C)=O.C(C)N(C(C1=C(C=CC(=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O)CC Chemical compound ClC=1C=CC(=C(C(=O)N(CC)CC)C1)NC1=C(C=C(C=C1)I)C.C(CCC)NC(C1=C(C=C(C=C1)F)NC1=C(C=C(C=C1)I)C)=O.C(C)N(C(C1=C(C=CC(=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O)CC YREBQENZDVFKER-UHFFFAOYSA-N 0.000 claims 1
• CLXHXIIAFZOHJZ-UHFFFAOYSA-N ClC=1C=CC(=C(C(=O)NOC2OCCCC2)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)C Chemical compound ClC=1C=CC(=C(C(=O)NOC2OCCCC2)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)C CLXHXIIAFZOHJZ-UHFFFAOYSA-N 0.000 claims 1
• NEBXZSZQBQSZOJ-UHFFFAOYSA-M ClC=1C=CC(=C(C(=O)[O-])C1)NC1=C(C=C(C=C1)I)C.[Na+].ClC=1C=CC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)I)C.BrC=1C(=C(C(=C(C(=O)O)C1)NC1=C(C=C(C=C1)I)C)F)F Chemical compound ClC=1C=CC(=C(C(=O)[O-])C1)NC1=C(C=C(C=C1)I)C.[Na+].ClC=1C=CC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)I)C.BrC=1C(=C(C(=C(C(=O)O)C1)NC1=C(C=C(C=C1)I)C)F)F NEBXZSZQBQSZOJ-UHFFFAOYSA-M 0.000 claims 1
• IJPWOLXIVFMSIK-UHFFFAOYSA-N FC1=CC(=C(C(=O)NO)C=C1)NC1=C(C=C(C=C1)I)F.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)[N+](=O)[O-] Chemical compound FC1=CC(=C(C(=O)NO)C=C1)NC1=C(C=C(C=C1)I)F.BrC1=C(C=CC(=C1)I)NC1=C(C(=O)NO)C=CC(=C1)[N+](=O)[O-] IJPWOLXIVFMSIK-UHFFFAOYSA-N 0.000 claims 1
• NSSBRUHASPXVJA-UHFFFAOYSA-N FC1=CC(=C(C(=O)NOC2CCCC2)C=C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NOCC2CC2)C=C1)NC1=C(C=C(C=C1)I)C Chemical compound FC1=CC(=C(C(=O)NOC2CCCC2)C=C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NOCC2CC2)C=C1)NC1=C(C=C(C=C1)I)C NSSBRUHASPXVJA-UHFFFAOYSA-N 0.000 claims 1
• XGLLBCGIHJLUBO-UHFFFAOYSA-N FC1=CC(=C(C(=O)NOCC#C)C=C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NOC)C=C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NO)C=C1)NC1=C(C=C(C=C1)I)C Chemical compound FC1=CC(=C(C(=O)NOCC#C)C=C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NOC)C=C1)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)NO)C=C1)NC1=C(C=C(C=C1)I)C XGLLBCGIHJLUBO-UHFFFAOYSA-N 0.000 claims 1
• CTSIRQWSJFDATP-UHFFFAOYSA-N FC1=CC(=C(C(=O)NOCC2=CC=CC=C2)C=C1)NC1=C(C=C(C=C1)I)C.BrC1=CC(=C(C(=O)NOCC2=CC=CC=C2)C=C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NOC)C1)NC1=C(C=C(C=C1)I)C Chemical compound FC1=CC(=C(C(=O)NOCC2=CC=CC=C2)C=C1)NC1=C(C=C(C=C1)I)C.BrC1=CC(=C(C(=O)NOCC2=CC=CC=C2)C=C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NOC)C1)NC1=C(C=C(C=C1)I)C CTSIRQWSJFDATP-UHFFFAOYSA-N 0.000 claims 1
• FIADZNOLMGNYDK-UHFFFAOYSA-N FC=1C(=C(C(=O)NCCC2=CC=NC=C2)C=CC1F)NC1=C(C=C(C=C1)I)C.FC=1C(=C(C(=O)NCCN2CCCC2)C=CC1F)NC1=C(C=C(C=C1)I)C Chemical compound FC=1C(=C(C(=O)NCCC2=CC=NC=C2)C=CC1F)NC1=C(C=C(C=C1)I)C.FC=1C(=C(C(=O)NCCN2CCCC2)C=CC1F)NC1=C(C=C(C=C1)I)C FIADZNOLMGNYDK-UHFFFAOYSA-N 0.000 claims 1
• LZUGEBZWACZESH-UHFFFAOYSA-N FC=1C(=C(C(=O)NO)C=C(C1F)F)NC1=C(C=C(C=C1)I)F.ONC(C1=C(C=C(C=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O Chemical compound FC=1C(=C(C(=O)NO)C=C(C1F)F)NC1=C(C=C(C=C1)I)F.ONC(C1=C(C=C(C=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O LZUGEBZWACZESH-UHFFFAOYSA-N 0.000 claims 1
• VHDQHBLAPGJDTF-UHFFFAOYSA-N FC=1C(=C(C(=O)NOCC#CC(C)(C)C)C=CC1F)NC1=C(C=C(C=C1)Br)C.FC=1C(=C(C(=O)NOCC#CC2=CC(=CC=C2)F)C=CC1F)NC1=C(C=C(C=C1)Br)C Chemical compound FC=1C(=C(C(=O)NOCC#CC(C)(C)C)C=CC1F)NC1=C(C=C(C=C1)Br)C.FC=1C(=C(C(=O)NOCC#CC2=CC(=CC=C2)F)C=CC1F)NC1=C(C=C(C=C1)Br)C VHDQHBLAPGJDTF-UHFFFAOYSA-N 0.000 claims 1
• YHGRUXLEVQCLJP-UHFFFAOYSA-N FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)I)C.FC=1C(=C(C(=O)O)C=C(C1F)F)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)O)C=C1)NC1=C(C=C(C=C1)I)C Chemical compound FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)I)C.FC=1C(=C(C(=O)O)C=C(C1F)F)NC1=C(C=C(C=C1)I)C.FC1=CC(=C(C(=O)O)C=C1)NC1=C(C=C(C=C1)I)C YHGRUXLEVQCLJP-UHFFFAOYSA-N 0.000 claims 1
• CHXHPIRRYRGXBG-UHFFFAOYSA-N FC=1C=CC(=C(C(=O)N(C2=CC=CC=C2)C)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C Chemical compound FC=1C=CC(=C(C(=O)N(C2=CC=CC=C2)C)C1)NC1=C(C=C(C=C1)I)C.ClC=1C=CC(=C(C(=O)NC2CC2)C1)NC1=C(C=C(C=C1)I)C CHXHPIRRYRGXBG-UHFFFAOYSA-N 0.000 claims 1
• IYNYOWHOUWWBSK-UHFFFAOYSA-N FC=1C=CC(=C(C(=O)NCC2=CC=C(C=C2)S(N)(=O)=O)C1)NC1=C(C=C(C=C1)I)C.C(C1=CC=CC=C1)ONC(C1=C(C=CC(=C1)I)NC1=C(C=C(C=C1)I)C)=O Chemical compound FC=1C=CC(=C(C(=O)NCC2=CC=C(C=C2)S(N)(=O)=O)C1)NC1=C(C=C(C=C1)I)C.C(C1=CC=CC=C1)ONC(C1=C(C=CC(=C1)I)NC1=C(C=C(C=C1)I)C)=O IYNYOWHOUWWBSK-UHFFFAOYSA-N 0.000 claims 1
• CRASLNLHNNQNOO-UHFFFAOYSA-N FC=1C=CC(=C(C(=O)NCCN2CCCC2)C1)NC1=C(C=C(C=C1)I)C.BrC=1C=CC(=C(C(=O)NCCN2CCCCC2)C1)NC1=C(C=C(C=C1)I)C Chemical compound FC=1C=CC(=C(C(=O)NCCN2CCCC2)C1)NC1=C(C=C(C=C1)I)C.BrC=1C=CC(=C(C(=O)NCCN2CCCCC2)C1)NC1=C(C=C(C=C1)I)C CRASLNLHNNQNOO-UHFFFAOYSA-N 0.000 claims 1
• CBAZYTDIGQKODF-UHFFFAOYSA-N IC=1C=CC(=C(C(=O)NOCC2=CC=CC=C2)C1)NC1=C(C=C(C=C1)I)C.FC=1C=CC(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)C Chemical compound IC=1C=CC(=C(C(=O)NOCC2=CC=CC=C2)C1)NC1=C(C=C(C=C1)I)C.FC=1C=CC(=C(C(=O)NO)C1)NC1=C(C=C(C=C1)I)C CBAZYTDIGQKODF-UHFFFAOYSA-N 0.000 claims 1
• QHQSDKLERZNQTE-UHFFFAOYSA-N IC=1C=CC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)I)C.FC=1C=CC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)I)C.IC1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC=C1)C Chemical compound IC=1C=CC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)I)C.FC=1C=CC(=C(C(=O)O)C1)NC1=C(C=C(C=C1)I)C.IC1=CC(=C(C=C1)NC1=C(C(=O)O)C=CC=C1)C QHQSDKLERZNQTE-UHFFFAOYSA-N 0.000 claims 1
• HXEOWZGLSMUDBL-UHFFFAOYSA-N N-benzyl-4-fluoro-2-(4-iodo-2-methylanilino)benzamide N-[3-(dimethylamino)propyl]-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound C(C1=CC=CC=C1)NC(C1=C(C=C(C=C1)F)NC1=C(C=C(C=C1)I)C)=O.CN(CCCNC(C1=C(C(=C(C=C1)F)F)NC1=C(C=C(C=C1)I)C)=O)C HXEOWZGLSMUDBL-UHFFFAOYSA-N 0.000 claims 1
• BMZKHPTXLPDFPV-UHFFFAOYSA-N OCCCNC(C1=C(C=CC(=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O.BrC=1C=CC(=C(C(=O)NCCCN(C)C)C1)NC1=C(C=C(C=C1)I)C Chemical compound OCCCNC(C1=C(C=CC(=C1)[N+](=O)[O-])NC1=C(C=C(C=C1)I)C)=O.BrC=1C=CC(=C(C(=O)NCCCN(C)C)C1)NC1=C(C=C(C=C1)I)C BMZKHPTXLPDFPV-UHFFFAOYSA-N 0.000 claims 1
• AERSZUTUGFQQED-UHFFFAOYSA-N OCCN(CCNC(C1=C(C=CC(=C1)Cl)NC1=C(C=C(C=C1)I)C)=O)CCO.BrC=1C=CC(=C(C(=O)NCCN(CC)CC)C1)NC1=C(C=C(C=C1)I)C Chemical compound OCCN(CCNC(C1=C(C=CC(=C1)Cl)NC1=C(C=C(C=C1)I)C)=O)CCO.BrC=1C=CC(=C(C(=O)NCCN(CC)CC)C1)NC1=C(C=C(C=C1)I)C AERSZUTUGFQQED-UHFFFAOYSA-N 0.000 claims 1
• WEIKYIWCHZIAHU-UHFFFAOYSA-N OCCN(CCNC(C1=C(C=CC(=C1)F)NC1=C(C=C(C=C1)I)C)=O)CCO.ClC=1C=CC(=C(C(=O)NCCCN(C)C)C1)NC1=C(C=C(C=C1)I)C Chemical compound OCCN(CCNC(C1=C(C=CC(=C1)F)NC1=C(C=C(C=C1)I)C)=O)CCO.ClC=1C=CC(=C(C(=O)NCCCN(C)C)C1)NC1=C(C=C(C=C1)I)C WEIKYIWCHZIAHU-UHFFFAOYSA-N 0.000 claims 1
• NFXXOOKASIVLTM-UHFFFAOYSA-N OCCNC(C1=C(C=CC(=C1)I)NC1=C(C=C(C=C1)I)C)=O.BrC=1C=CC(=C(C(=O)NCCO)C1)NC1=C(C=C(C=C1)I)C Chemical compound OCCNC(C1=C(C=CC(=C1)I)NC1=C(C=C(C=C1)I)C)=O.BrC=1C=CC(=C(C(=O)NCCO)C1)NC1=C(C=C(C=C1)I)C NFXXOOKASIVLTM-UHFFFAOYSA-N 0.000 claims 1
• 238000011319 anticancer therapy Methods 0.000 claims 1
• 239000000243 solution Substances 0.000 description 52
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 47
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 46
• 150000001875 compounds Chemical class 0.000 description 45
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 24
• 210000004027 cell Anatomy 0.000 description 24
• 239000003795 chemical substances by application Substances 0.000 description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
• 238000002360 preparation method Methods 0.000 description 22
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
• 238000006243 chemical reaction Methods 0.000 description 20
• 239000000203 mixture Substances 0.000 description 20
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 239000007787 solid Substances 0.000 description 18
• 238000002844 melting Methods 0.000 description 17
• 230000008018 melting Effects 0.000 description 17
• 239000011541 reaction mixture Substances 0.000 description 17
• 239000003921 oil Substances 0.000 description 16
• 235000019198 oils Nutrition 0.000 description 16
• 239000002904 solvent Substances 0.000 description 16
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• 239000005711 Benzoic acid Substances 0.000 description 14
• 235000010233 benzoic acid Nutrition 0.000 description 13
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• 238000005160 1H NMR spectroscopy Methods 0.000 description 11
• 102000004190 Enzymes Human genes 0.000 description 11
• 108090000790 Enzymes Proteins 0.000 description 11
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
• 238000004458 analytical method Methods 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
• 235000019341 magnesium sulphate Nutrition 0.000 description 10
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
• 235000019441 ethanol Nutrition 0.000 description 9
• 206010009944 Colon cancer Diseases 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• 102000029749 Microtubule Human genes 0.000 description 7
• 108091022875 Microtubule Proteins 0.000 description 7
• 239000013543 active substance Substances 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 210000004688 microtubule Anatomy 0.000 description 7
• 238000004293 19F NMR spectroscopy Methods 0.000 description 6
• GUAFZVVAOQFCPJ-UHFFFAOYSA-N 5-bromo-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCO GUAFZVVAOQFCPJ-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 229960004756 ethanol Drugs 0.000 description 6
• 238000001704 evaporation Methods 0.000 description 6
• 230000008020 evaporation Effects 0.000 description 6
• ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 6
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 239000003960 organic solvent Substances 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• IIJDQEBBOFOXKL-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(O)=O IIJDQEBBOFOXKL-UHFFFAOYSA-N 0.000 description 5
• DMXADGCWZHCXBU-UHFFFAOYSA-N 5-chloro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCO DMXADGCWZHCXBU-UHFFFAOYSA-N 0.000 description 5
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
• GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 5
• 230000006907 apoptotic process Effects 0.000 description 5
• 125000004104 aryloxy group Chemical group 0.000 description 5
• 238000003556 assay Methods 0.000 description 5
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 238000004587 chromatography analysis Methods 0.000 description 5
• 208000029742 colonic neoplasm Diseases 0.000 description 5
• 238000002425 crystallisation Methods 0.000 description 5
• 230000008025 crystallization Effects 0.000 description 5
• 230000000547 effect on apoptosis Effects 0.000 description 5
• 238000010828 elution Methods 0.000 description 5
• 239000006260 foam Substances 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 239000012044 organic layer Substances 0.000 description 5
• 229920001223 polyethylene glycol Polymers 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 238000010561 standard procedure Methods 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IELIFDKJSA-N 0.000 description 5
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
• WRIPZDWCGAIYEF-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-nitro-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCC1=CC=C(S(N)(=O)=O)C=C1 WRIPZDWCGAIYEF-UHFFFAOYSA-N 0.000 description 4
• BGKLFAQCHHCZRZ-UHFFFAOYSA-N 4-iodo-2-methylaniline Chemical compound CC1=CC(I)=CC=C1N BGKLFAQCHHCZRZ-UHFFFAOYSA-N 0.000 description 4
• DSFQOJWTJQNGSU-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCC1=CC=C(S(N)(=O)=O)C=C1 DSFQOJWTJQNGSU-UHFFFAOYSA-N 0.000 description 4
• YNAWORHNPLOBBU-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-methyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC(Br)=CC=C1NC1=CC=C(I)C=C1C YNAWORHNPLOBBU-UHFFFAOYSA-N 0.000 description 4
• AANZSIPSXXHMRM-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NOCC1=CC=CC=C1 AANZSIPSXXHMRM-UHFFFAOYSA-N 0.000 description 4
• IHCADDZQYYEXFH-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(O)=O IHCADDZQYYEXFH-UHFFFAOYSA-N 0.000 description 4
• VBFVICYZHVZQIF-UHFFFAOYSA-N 5-bromo-n-cyclopropyl-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NC1CC1 VBFVICYZHVZQIF-UHFFFAOYSA-N 0.000 description 4
• OQWXTWHGTZIWBE-UHFFFAOYSA-N 5-chloro-n-[3-(dimethylamino)propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C OQWXTWHGTZIWBE-UHFFFAOYSA-N 0.000 description 4
• NRQYGGWYEHEXEJ-UHFFFAOYSA-N 5-chloro-n-cyclopropyl-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NC1CC1 NRQYGGWYEHEXEJ-UHFFFAOYSA-N 0.000 description 4
• PJCPYFYKAWDPLX-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCC1=CC=C(S(N)(=O)=O)C=C1 PJCPYFYKAWDPLX-UHFFFAOYSA-N 0.000 description 4
• CCGNHTHRIVEZPG-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NOCC1=CC=CC=C1 CCGNHTHRIVEZPG-UHFFFAOYSA-N 0.000 description 4
• YSXVOTVVUSIKNI-UHFFFAOYSA-N 5-fluoro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCO YSXVOTVVUSIKNI-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
• 150000007513 acids Chemical class 0.000 description 4
• 230000000259 anti-tumor effect Effects 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 125000004663 dialkyl amino group Chemical group 0.000 description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
• 150000002443 hydroxylamines Chemical class 0.000 description 4
• RYOCQJVSICWPKA-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCCO RYOCQJVSICWPKA-UHFFFAOYSA-N 0.000 description 4
• JDQKKPHXLMZTFM-UHFFFAOYSA-N n-(2-hydroxyethyl)-5-iodo-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(=O)NCCO JDQKKPHXLMZTFM-UHFFFAOYSA-N 0.000 description 4
• HPFQWCKXOZLYJQ-UHFFFAOYSA-N n-but-2-enoxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC=CCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C HPFQWCKXOZLYJQ-UHFFFAOYSA-N 0.000 description 4
• IDXFBAOJNKCQTB-UHFFFAOYSA-N n-cyclopropyl-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NC1CC1 IDXFBAOJNKCQTB-UHFFFAOYSA-N 0.000 description 4
• APDFSUINPPLQLM-UHFFFAOYSA-N n-cyclopropyl-5-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NC1CC1 APDFSUINPPLQLM-UHFFFAOYSA-N 0.000 description 4
• 231100000252 nontoxic Toxicity 0.000 description 4
• 230000003000 nontoxic effect Effects 0.000 description 4
• 239000000546 pharmaceutical excipient Substances 0.000 description 4
• 230000002829 reductive effect Effects 0.000 description 4
• 238000005070 sampling Methods 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 125000000547 substituted alkyl group Chemical group 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• QFWCYNPOPKQOKV-UHFFFAOYSA-N 2-(2-amino-3-methoxyphenyl)chromen-4-one Chemical group COC1=CC=CC(C=2OC3=CC=CC=C3C(=O)C=2)=C1N QFWCYNPOPKQOKV-UHFFFAOYSA-N 0.000 description 3
• LUDUVSBHPMEVQH-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-propan-2-yloxybenzamide Chemical compound CC(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C LUDUVSBHPMEVQH-UHFFFAOYSA-N 0.000 description 3
• SLODYXNZAINLFD-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-but-2-enoxy-3,4-difluorobenzamide Chemical compound CC=CCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C SLODYXNZAINLFD-UHFFFAOYSA-N 0.000 description 3
• YDBKFXZLWHEYBN-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-ethoxy-3,4-difluorobenzamide Chemical compound CCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C YDBKFXZLWHEYBN-UHFFFAOYSA-N 0.000 description 3
• LFKXETJHTXTXSA-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-nitrobenzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(O)=O LFKXETJHTXTXSA-UHFFFAOYSA-N 0.000 description 3
• XKRVQEHFHLIYHN-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-n-methyl-5-nitro-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(I)C=C1C XKRVQEHFHLIYHN-UHFFFAOYSA-N 0.000 description 3
• IKYHHUKKYADHCL-UHFFFAOYSA-N 3,4,5-trifluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C(O)=O IKYHHUKKYADHCL-UHFFFAOYSA-N 0.000 description 3
• ZWXXSMYLKXWUIM-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-prop-2-ynoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC#C ZWXXSMYLKXWUIM-UHFFFAOYSA-N 0.000 description 3
• XRNCNLRJMNWXRG-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(O)=O XRNCNLRJMNWXRG-UHFFFAOYSA-N 0.000 description 3
• IVJXLCPTSRJPLQ-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCC1=CC=CC=C1 IVJXLCPTSRJPLQ-UHFFFAOYSA-N 0.000 description 3
• MTTOQVVDHYZDHE-UHFFFAOYSA-N 5-(5-chloro-2-fluorophenyl)-2h-tetrazole Chemical compound FC1=CC=C(Cl)C=C1C1=NN=NN1 MTTOQVVDHYZDHE-UHFFFAOYSA-N 0.000 description 3
• MFISPQKUQORGHB-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-methyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C MFISPQKUQORGHB-UHFFFAOYSA-N 0.000 description 3
• MBXXUKAZBOOXOL-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(O)=O MBXXUKAZBOOXOL-UHFFFAOYSA-N 0.000 description 3
• YPPGTJWMYLGECO-UHFFFAOYSA-N 5-chloro-n-cyclohexyl-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NC1CCCCC1 YPPGTJWMYLGECO-UHFFFAOYSA-N 0.000 description 3
• KCOUCDQMKMTOGV-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-methyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC(F)=CC=C1NC1=CC=C(I)C=C1C KCOUCDQMKMTOGV-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
• 108091054455 MAP kinase family Proteins 0.000 description 3
• 102000043136 MAP kinase family Human genes 0.000 description 3
• 241001465754 Metazoa Species 0.000 description 3
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
• 239000002671 adjuvant Substances 0.000 description 3
• 230000008901 benefit Effects 0.000 description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
• 229910052794 bromium Inorganic materials 0.000 description 3
• 238000009833 condensation Methods 0.000 description 3
• 230000005494 condensation Effects 0.000 description 3
• 229940043279 diisopropylamine Drugs 0.000 description 3
• 239000006185 dispersion Substances 0.000 description 3
• 238000004821 distillation Methods 0.000 description 3
• 239000003995 emulsifying agent Substances 0.000 description 3
• 239000000284 extract Substances 0.000 description 3
• 238000003818 flash chromatography Methods 0.000 description 3
• 125000001153 fluoro group Chemical group F* 0.000 description 3
• 235000011187 glycerol Nutrition 0.000 description 3
• 239000003906 humectant Substances 0.000 description 3
• 229940090044 injection Drugs 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• 238000002156 mixing Methods 0.000 description 3
• VWYKMLWQWMJQSO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CN(C)CCCNC(=O)C1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(I)C=C1C VWYKMLWQWMJQSO-UHFFFAOYSA-N 0.000 description 3
• HHVULRUXZSEDQK-UHFFFAOYSA-N n-but-3-ynoxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCCC#C HHVULRUXZSEDQK-UHFFFAOYSA-N 0.000 description 3
• GNBCJLIYQMNLNA-UHFFFAOYSA-N n-cyclopropyl-5-iodo-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(=O)NC1CC1 GNBCJLIYQMNLNA-UHFFFAOYSA-N 0.000 description 3
• 239000012074 organic phase Substances 0.000 description 3
• 229940108949 paclitaxel injection Drugs 0.000 description 3
• 239000006187 pill Substances 0.000 description 3
• 239000007909 solid dosage form Substances 0.000 description 3
• 239000000829 suppository Substances 0.000 description 3
• RCINICONZNJXQF-XAZOAEDWSA-N taxol® Chemical compound O([C@@H]1[C@@]2(CC(C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3(C21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-XAZOAEDWSA-N 0.000 description 3
• 239000008096 xylene Substances 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 2
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
• IWZZOJQMYWDXJN-UHFFFAOYSA-N 2,3,5-trifluoro-4-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C=C(C(O)=O)C(F)=C1F IWZZOJQMYWDXJN-UHFFFAOYSA-N 0.000 description 2
• NJYBIFYEWYWYAN-UHFFFAOYSA-N 2,4-difluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1F NJYBIFYEWYWYAN-UHFFFAOYSA-N 0.000 description 2
• QMALWSSCPZJMOO-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(I)C=C1Br QMALWSSCPZJMOO-UHFFFAOYSA-N 0.000 description 2
• QBTVPUBNRWFMGL-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCN1CCOCC1 QBTVPUBNRWFMGL-UHFFFAOYSA-N 0.000 description 2
• NITWKACUMSHLOB-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-phenoxyethoxy)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCCOC1=CC=CC=C1 NITWKACUMSHLOB-UHFFFAOYSA-N 0.000 description 2
• PFLMFENBMHGHFI-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-phenylethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCC1=CC=CC=C1 PFLMFENBMHGHFI-UHFFFAOYSA-N 0.000 description 2
• MSOPPMSDGHOWLB-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-piperidin-1-ylethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCN1CCCCC1 MSOPPMSDGHOWLB-UHFFFAOYSA-N 0.000 description 2
• YGHCZGICKAIMTC-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-pyridin-4-ylethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCC1=CC=NC=C1 YGHCZGICKAIMTC-UHFFFAOYSA-N 0.000 description 2
• JILKHIVXSCYZRF-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCN1CCCC1 JILKHIVXSCYZRF-UHFFFAOYSA-N 0.000 description 2
• JGKIBUDEERWECG-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-thiophen-2-ylethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCC1=CC=CS1 JGKIBUDEERWECG-UHFFFAOYSA-N 0.000 description 2
• MPKKNJJTFVARIP-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(3-hydroxypropyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCCO MPKKNJJTFVARIP-UHFFFAOYSA-N 0.000 description 2
• DLCASGFAOPGKAH-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(3-phenylprop-2-ynoxy)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC#CC1=CC=CC=C1 DLCASGFAOPGKAH-UHFFFAOYSA-N 0.000 description 2
• ULZOCHGQJGYENN-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(thiophen-2-ylmethoxy)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1=CC=CS1 ULZOCHGQJGYENN-UHFFFAOYSA-N 0.000 description 2
• MCDZEUZYVPGCQV-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-[3-(3-fluorophenyl)prop-2-ynoxy]benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC#CC1=CC=CC(F)=C1 MCDZEUZYVPGCQV-UHFFFAOYSA-N 0.000 description 2
• WGIDTTDBLPTUHP-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-methoxybenzamide Chemical compound CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C WGIDTTDBLPTUHP-UHFFFAOYSA-N 0.000 description 2
• HNXJNPOQVWVOGW-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-propoxybenzamide Chemical compound CCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C HNXJNPOQVWVOGW-UHFFFAOYSA-N 0.000 description 2
• OKAIUFBLOQNKIS-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluorobenzoic acid Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(O)=O OKAIUFBLOQNKIS-UHFFFAOYSA-N 0.000 description 2
• DFYRJMXCUCOACA-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-4-fluorobenzoic acid Chemical compound CC1=CC(Br)=CC=C1NC1=CC(F)=CC=C1C(O)=O DFYRJMXCUCOACA-UHFFFAOYSA-N 0.000 description 2
• QTCFRZPPKGEZKF-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-(4,4-dimethylpent-2-ynoxy)-3,4-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC#CC(C)(C)C QTCFRZPPKGEZKF-UHFFFAOYSA-N 0.000 description 2
• RASWBMJSCOCCOP-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-[3-(dimethylamino)propyl]-3,4-difluorobenzamide Chemical compound CN(C)CCCNC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C RASWBMJSCOCCOP-UHFFFAOYSA-N 0.000 description 2
• LNTZEUIWPWPUGC-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-but-3-yn-2-yloxy-3,4-difluorobenzamide Chemical compound C#CC(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C LNTZEUIWPWPUGC-UHFFFAOYSA-N 0.000 description 2
• LWZBCTIJTITZBA-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-but-3-ynoxy-3,4-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCCC#C LWZBCTIJTITZBA-UHFFFAOYSA-N 0.000 description 2
• LUVODTHAYCCRJL-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-cyclobutyloxy-3,4-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOC1CCC1 LUVODTHAYCCRJL-UHFFFAOYSA-N 0.000 description 2
• BZEJFQCJTPHNOF-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-cyclopentyloxy-3,4-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOC1CCCC1 BZEJFQCJTPHNOF-UHFFFAOYSA-N 0.000 description 2
• IPJKPORKWBURKZ-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-4-nitrobenzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC([N+]([O-])=O)=CC=C1C(O)=O IPJKPORKWBURKZ-UHFFFAOYSA-N 0.000 description 2
• OPSQYIMKGZTWMH-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-methylbenzoic acid Chemical compound OC(=O)C1=CC(C)=CC=C1NC1=CC=C(I)C=C1C OPSQYIMKGZTWMH-UHFFFAOYSA-N 0.000 description 2
• KLYXRBOQQVDCRR-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-n-[(3-methylphenyl)methyl]-5-nitrobenzamide Chemical compound CC1=CC=CC(CNC(=O)C=2C(=CC=C(C=2)[N+]([O-])=O)NC=2C(=CC(I)=CC=2)C)=C1 KLYXRBOQQVDCRR-UHFFFAOYSA-N 0.000 description 2
• XLTVXGORWXCJNJ-UHFFFAOYSA-N 2-(4-iodoanilino)-5-methoxybenzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC=C(I)C=C1 XLTVXGORWXCJNJ-UHFFFAOYSA-N 0.000 description 2
• LNWRKPWPMUWTGU-UHFFFAOYSA-N 2-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound NC(=O)C1=CC=C(F)C(F)=C1OCC1CC1 LNWRKPWPMUWTGU-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• VXBGETLMHVNAMH-UHFFFAOYSA-N 2-[[5-chloro-2-(4-iodo-2-methylanilino)benzoyl]amino]acetic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCC(O)=O VXBGETLMHVNAMH-UHFFFAOYSA-N 0.000 description 2
• IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 2
• NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
• XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 description 2
• HYIXUGDJHLKVGF-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-phenoxyethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCCOC1=CC=CC=C1 HYIXUGDJHLKVGF-UHFFFAOYSA-N 0.000 description 2
• OSWADHCUFNBMDE-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-pyridin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCC1=CC=NC=C1 OSWADHCUFNBMDE-UHFFFAOYSA-N 0.000 description 2
• HSRZYLYUHGKRQA-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCN1CCCC1 HSRZYLYUHGKRQA-UHFFFAOYSA-N 0.000 description 2
• RLUBNNSZZPDBIV-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(3-phenylprop-2-ynoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC#CC1=CC=CC=C1 RLUBNNSZZPDBIV-UHFFFAOYSA-N 0.000 description 2
• JWVMVMKROCWQQV-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCCN1CCCCC1 JWVMVMKROCWQQV-UHFFFAOYSA-N 0.000 description 2
• HAONTWSXIVMMHV-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(thiophen-2-ylmethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1=CC=CS1 HAONTWSXIVMMHV-UHFFFAOYSA-N 0.000 description 2
• YFDMZMSYQKSLLM-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-propan-2-yloxybenzamide Chemical compound CC(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C YFDMZMSYQKSLLM-UHFFFAOYSA-N 0.000 description 2
• FUDMVYZZNQDLOV-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-propoxybenzamide Chemical compound CCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C FUDMVYZZNQDLOV-UHFFFAOYSA-N 0.000 description 2
• KEAXMKQPXUVLBO-UHFFFAOYSA-N 3,4-difluoro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCO KEAXMKQPXUVLBO-UHFFFAOYSA-N 0.000 description 2
• YPKLFSUXFMFTNP-UHFFFAOYSA-N 3,4-difluoro-n-(furan-3-ylmethoxy)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1=COC=C1 YPKLFSUXFMFTNP-UHFFFAOYSA-N 0.000 description 2
• LEYZOHZNXYPUBL-UHFFFAOYSA-N 4-chloro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC(Cl)=CC=C1C(O)=O LEYZOHZNXYPUBL-UHFFFAOYSA-N 0.000 description 2
• FYFHVQLFQOKLEM-UHFFFAOYSA-N 4-chloro-4-iodo-6-methyl-6-(2h-tetrazol-5-yl)cyclohex-2-en-1-amine Chemical compound N1=NNN=C1C1(C)CC(Cl)(I)C=CC1N FYFHVQLFQOKLEM-UHFFFAOYSA-N 0.000 description 2
• KVCZARDORIUTAK-UHFFFAOYSA-N 4-fluoro-2-(4-fluoro-2-methylanilino)-n-hydroxybenzamide Chemical compound CC1=CC(F)=CC=C1NC1=CC(F)=CC=C1C(=O)NO KVCZARDORIUTAK-UHFFFAOYSA-N 0.000 description 2
• GHJJMBQQZZBWJC-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C GHJJMBQQZZBWJC-UHFFFAOYSA-N 0.000 description 2
• XYPDOWBXGOOEOA-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-phenoxyethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCCOC1=CC=CC=C1 XYPDOWBXGOOEOA-UHFFFAOYSA-N 0.000 description 2
• JPFLPYISXHNBBZ-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-phenylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCC1=CC=CC=C1 JPFLPYISXHNBBZ-UHFFFAOYSA-N 0.000 description 2
• TXVFFQLHNCTHDG-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-pyridin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCC1=CC=NC=C1 TXVFFQLHNCTHDG-UHFFFAOYSA-N 0.000 description 2
• ALEXORMOTRNKGS-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCN1CCCC1 ALEXORMOTRNKGS-UHFFFAOYSA-N 0.000 description 2
• FXKGVPODJZKPSN-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-thiophen-2-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCC1=CC=CS1 FXKGVPODJZKPSN-UHFFFAOYSA-N 0.000 description 2
• KYPCIWQNEIGNMW-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2h-tetrazol-5-yl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NC1=NN=NN1 KYPCIWQNEIGNMW-UHFFFAOYSA-N 0.000 description 2
• PBAMOEUDSFIDGM-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(thiophen-2-ylmethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCC1=CC=CS1 PBAMOEUDSFIDGM-UHFFFAOYSA-N 0.000 description 2
• PEZQORQECWUYJA-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-methoxybenzamide Chemical compound CONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C PEZQORQECWUYJA-UHFFFAOYSA-N 0.000 description 2
• HHSBHFSKYJRNAR-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C HHSBHFSKYJRNAR-UHFFFAOYSA-N 0.000 description 2
• VFLRZRPXLGMONP-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-prop-2-ynoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCC#C VFLRZRPXLGMONP-UHFFFAOYSA-N 0.000 description 2
• WOHHWWLIRJXRJT-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-propylbenzamide Chemical compound CCCNC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C WOHHWWLIRJXRJT-UHFFFAOYSA-N 0.000 description 2
• COEXMYRMIABFRK-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(N)=O COEXMYRMIABFRK-UHFFFAOYSA-N 0.000 description 2
• DWXSHLDPWGVUAY-UHFFFAOYSA-N 4-fluoro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCO DWXSHLDPWGVUAY-UHFFFAOYSA-N 0.000 description 2
• RBSKNOAECVHCJC-UHFFFAOYSA-N 4-iodo-2-methyl-n-[2-(2h-tetrazol-5-yl)phenyl]aniline Chemical compound CC1=CC(I)=CC=C1NC1=CC=CC=C1C1=NN=NN1 RBSKNOAECVHCJC-UHFFFAOYSA-N 0.000 description 2
• VLVCDUSVTXIWGW-UHFFFAOYSA-N 4-iodoaniline Chemical compound NC1=CC=C(I)C=C1 VLVCDUSVTXIWGW-UHFFFAOYSA-N 0.000 description 2
• YGSACSKOTDWEIY-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC(Br)=CC=C1NC1=CC=C(I)C=C1C YGSACSKOTDWEIY-UHFFFAOYSA-N 0.000 description 2
• KACROHVGLWUBCA-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCN1CCOCC1 KACROHVGLWUBCA-UHFFFAOYSA-N 0.000 description 2
• IAVNIGIRNWGCLU-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-(2-piperidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCN1CCCCC1 IAVNIGIRNWGCLU-UHFFFAOYSA-N 0.000 description 2
• NJJDWJWIEWSECZ-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCN1CCCC1 NJJDWJWIEWSECZ-UHFFFAOYSA-N 0.000 description 2
• HIDZKFBLBMEGIG-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCCN1CCCCC1 HIDZKFBLBMEGIG-UHFFFAOYSA-N 0.000 description 2
• MXCDWFRGCXEWHI-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-[(3-methylphenyl)methyl]benzamide Chemical compound CC1=CC=CC(CNC(=O)C=2C(=CC=C(Br)C=2)NC=2C(=CC(I)=CC=2)C)=C1 MXCDWFRGCXEWHI-UHFFFAOYSA-N 0.000 description 2
• GTXGFBQHXPMFRF-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(N)=O GTXGFBQHXPMFRF-UHFFFAOYSA-N 0.000 description 2
• BSFZRPNXKUHUAO-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(O)=O BSFZRPNXKUHUAO-UHFFFAOYSA-N 0.000 description 2
• LOWHNAGNDJCFSR-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-pyridin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCC1=CC=NC=C1 LOWHNAGNDJCFSR-UHFFFAOYSA-N 0.000 description 2
• RDSDFNHYHOTLTQ-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCN1CCCC1 RDSDFNHYHOTLTQ-UHFFFAOYSA-N 0.000 description 2
• SQGHOLDHMVSJEQ-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(pyridin-4-ylmethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCC1=CC=NC=C1 SQGHOLDHMVSJEQ-UHFFFAOYSA-N 0.000 description 2
• NCTFSDXSASAYPI-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-propan-2-yloxybenzamide Chemical compound CC(C)ONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C NCTFSDXSASAYPI-UHFFFAOYSA-N 0.000 description 2
• IGSVYYMTMKJIDZ-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-propoxybenzamide Chemical compound CCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C IGSVYYMTMKJIDZ-UHFFFAOYSA-N 0.000 description 2
• DSNSWZOBIUQUBS-UHFFFAOYSA-N 5-bromo-3,4-difluoro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCO DSNSWZOBIUQUBS-UHFFFAOYSA-N 0.000 description 2
• KAURXOFXGMYTLE-UHFFFAOYSA-N 5-bromo-3,4-difluoro-n-[3-(2-fluorophenyl)prop-2-ynoxy]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC#CC1=CC=CC=C1F KAURXOFXGMYTLE-UHFFFAOYSA-N 0.000 description 2
• PADIEEAWBNJBQS-UHFFFAOYSA-N 5-bromo-n-(3-hydroxypropyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCCO PADIEEAWBNJBQS-UHFFFAOYSA-N 0.000 description 2
• AZVJODFNVSECTP-UHFFFAOYSA-N 5-bromo-n-[2-(diethylamino)ethyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Br)=CC=C1NC1=CC=C(I)C=C1C AZVJODFNVSECTP-UHFFFAOYSA-N 0.000 description 2
• IVARVMGCQQJYCS-UHFFFAOYSA-N 5-bromo-n-[2-[di(propan-2-yl)amino]ethyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC(C)N(C(C)C)CCNC(=O)C1=CC(Br)=CC=C1NC1=CC=C(I)C=C1C IVARVMGCQQJYCS-UHFFFAOYSA-N 0.000 description 2
• YUKGGEUVPFOCFI-UHFFFAOYSA-N 5-bromo-n-[3-(dimethylamino)propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC(Br)=CC=C1NC1=CC=C(I)C=C1C YUKGGEUVPFOCFI-UHFFFAOYSA-N 0.000 description 2
• JETNCDYHKNDALF-UHFFFAOYSA-N 5-bromo-n-[3-(dimethylamino)propyl]-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C JETNCDYHKNDALF-UHFFFAOYSA-N 0.000 description 2
• ZQOIUOMBQVPIAV-UHFFFAOYSA-N 5-bromo-n-but-2-enoxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC=CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C ZQOIUOMBQVPIAV-UHFFFAOYSA-N 0.000 description 2
• HOCJGOUUCDSSIA-UHFFFAOYSA-N 5-bromo-n-but-3-ynoxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCCC#C HOCJGOUUCDSSIA-UHFFFAOYSA-N 0.000 description 2
• GNQPYQRZLIRIAD-UHFFFAOYSA-N 5-bromo-n-cyclohexyl-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NC1CCCCC1 GNQPYQRZLIRIAD-UHFFFAOYSA-N 0.000 description 2
• YGRHTDDIYZYUDW-UHFFFAOYSA-N 5-chloro-2-(2-chloro-4-iodoanilino)-n-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=C(F)C(F)=C(Cl)C=C1C(=O)NOCC1CC1 YGRHTDDIYZYUDW-UHFFFAOYSA-N 0.000 description 2
• LVSSVNULIKSVNX-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C LVSSVNULIKSVNX-UHFFFAOYSA-N 0.000 description 2
• UQFNVBACOUIFNY-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-(2-piperidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCN1CCCCC1 UQFNVBACOUIFNY-UHFFFAOYSA-N 0.000 description 2
• ANJGKWAYKBLXEK-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCCN1CCCCC1 ANJGKWAYKBLXEK-UHFFFAOYSA-N 0.000 description 2
• HFKKIAJNJRTIFR-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-(oxan-2-yloxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NOC1OCCCC1 HFKKIAJNJRTIFR-UHFFFAOYSA-N 0.000 description 2
• RTCMPVBAZMDRHK-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-[(3-methylphenyl)methyl]benzamide Chemical compound CC1=CC=CC(CNC(=O)C=2C(=CC=C(Cl)C=2)NC=2C(=CC(I)=CC=2)C)=C1 RTCMPVBAZMDRHK-UHFFFAOYSA-N 0.000 description 2
• ORDKSJQARZCGBK-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-methoxybenzamide Chemical compound CONC(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C ORDKSJQARZCGBK-UHFFFAOYSA-N 0.000 description 2
• WDTUCEMLUHTMCB-UHFFFAOYSA-N 5-chloro-2-fluorobenzaldehyde Chemical compound FC1=CC=C(Cl)C=C1C=O WDTUCEMLUHTMCB-UHFFFAOYSA-N 0.000 description 2
• GJNJDELEHIGPKJ-UHFFFAOYSA-N 5-chloro-2-fluorobenzonitrile Chemical compound FC1=CC=C(Cl)C=C1C#N GJNJDELEHIGPKJ-UHFFFAOYSA-N 0.000 description 2
• FZJKEESBPVPDBV-UHFFFAOYSA-N 5-chloro-n,n-diethyl-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)C(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C FZJKEESBPVPDBV-UHFFFAOYSA-N 0.000 description 2
• NYSBUFZXTTZARS-UHFFFAOYSA-N 5-chloro-n-(cyclopropylmethoxy)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Cl)C=C1C(=O)NOCC1CC1 NYSBUFZXTTZARS-UHFFFAOYSA-N 0.000 description 2
• WPTQCTMJDFCZSI-UHFFFAOYSA-N 5-chloro-n-[2-(diethylamino)ethyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C WPTQCTMJDFCZSI-UHFFFAOYSA-N 0.000 description 2
• TUWOHSIPLLUTFB-UHFFFAOYSA-N 5-chloro-n-[2-[di(propan-2-yl)amino]ethyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC(C)N(C(C)C)CCNC(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C TUWOHSIPLLUTFB-UHFFFAOYSA-N 0.000 description 2
• HHLZFIBFGYVDRZ-UHFFFAOYSA-N 5-chloro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NO HHLZFIBFGYVDRZ-UHFFFAOYSA-N 0.000 description 2
• RMDPNUIMTHQHBO-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCN1CCOCC1 RMDPNUIMTHQHBO-UHFFFAOYSA-N 0.000 description 2
• TYGDKZJTFRTMAO-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-(2-piperidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCN1CCCCC1 TYGDKZJTFRTMAO-UHFFFAOYSA-N 0.000 description 2
• SFKIHCBPGXCYLE-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCN1CCCC1 SFKIHCBPGXCYLE-UHFFFAOYSA-N 0.000 description 2
• XTIXMUNFVWCJGM-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCCN1CCCCC1 XTIXMUNFVWCJGM-UHFFFAOYSA-N 0.000 description 2
• ADRDDDZHIAHVOS-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-(pyridin-4-ylmethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCC1=CC=NC=C1 ADRDDDZHIAHVOS-UHFFFAOYSA-N 0.000 description 2
• BNECLIPSPRXTNW-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-[(3-methylphenyl)methyl]benzamide Chemical compound CC1=CC=CC(CNC(=O)C=2C(=CC=C(F)C=2)NC=2C(=CC(I)=CC=2)C)=C1 BNECLIPSPRXTNW-UHFFFAOYSA-N 0.000 description 2
• NDLMMYHLEMKNIS-UHFFFAOYSA-N 5-fluoro-n-(3-hydroxypropyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCCO NDLMMYHLEMKNIS-UHFFFAOYSA-N 0.000 description 2
• USDURDZZSHBDOA-UHFFFAOYSA-N 5-iodo-2-(4-iodo-2-methylanilino)-n-[(3-methylphenyl)methyl]benzamide Chemical compound CC1=CC=CC(CNC(=O)C=2C(=CC=C(I)C=2)NC=2C(=CC(I)=CC=2)C)=C1 USDURDZZSHBDOA-UHFFFAOYSA-N 0.000 description 2
• LOUSDJOLFFYIHT-UHFFFAOYSA-N 5-iodo-2-(4-iodo-2-methylanilino)-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(=O)NCC1=CC=C(S(N)(=O)=O)C=C1 LOUSDJOLFFYIHT-UHFFFAOYSA-N 0.000 description 2
• ISSKCCWEUYSNQW-UHFFFAOYSA-N 5-iodo-2-(4-iodo-2-methylanilino)-n-methyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC(I)=CC=C1NC1=CC=C(I)C=C1C ISSKCCWEUYSNQW-UHFFFAOYSA-N 0.000 description 2
• KOXXMRABYKWLII-UHFFFAOYSA-N 5-iodo-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(O)=O KOXXMRABYKWLII-UHFFFAOYSA-N 0.000 description 2
• 229920001817 Agar Polymers 0.000 description 2
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
• 206010006187 Breast cancer Diseases 0.000 description 2
• 208000026310 Breast neoplasm Diseases 0.000 description 2
• 241000282472 Canis lupus familiaris Species 0.000 description 2
• 239000004215 Carbon black (E152) Substances 0.000 description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• 101000876610 Dictyostelium discoideum Extracellular signal-regulated kinase 2 Proteins 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• 241000206672 Gelidium Species 0.000 description 2
• 101001052493 Homo sapiens Mitogen-activated protein kinase 1 Proteins 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
• 206010020751 Hypersensitivity Diseases 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• 108040008097 MAP kinase activity proteins Proteins 0.000 description 2
• 102000019149 MAP kinase activity proteins Human genes 0.000 description 2
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 description 2
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
• 238000005481 NMR spectroscopy Methods 0.000 description 2
• 206010033128 Ovarian cancer Diseases 0.000 description 2
• 206010061535 Ovarian neoplasm Diseases 0.000 description 2
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
• KPKZJLCSROULON-QKGLWVMZSA-N Phalloidin Chemical compound N1C(=O)[C@@H]([C@@H](O)C)NC(=O)[C@H](C)NC(=O)[C@H](C[C@@](C)(O)CO)NC(=O)[C@H](C2)NC(=O)[C@H](C)NC(=O)[C@@H]3C[C@H](O)CN3C(=O)[C@@H]1CSC1=C2C2=CC=CC=C2N1 KPKZJLCSROULON-QKGLWVMZSA-N 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• 206010040070 Septic Shock Diseases 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• 102000004243 Tubulin Human genes 0.000 description 2
• 108090000704 Tubulin Proteins 0.000 description 2
• AEWSGTALCFCSLJ-UHFFFAOYSA-N [5-bromo-2-(4-iodo-2-methylanilino)phenyl]-(3-hydroxypyrrolidin-1-yl)methanone Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)N1CC(O)CC1 AEWSGTALCFCSLJ-UHFFFAOYSA-N 0.000 description 2
• BUMLXUPLPMQWRK-UHFFFAOYSA-N [5-fluoro-2-(4-iodo-2-methylanilino)phenyl]-[4-(2-hydroxyethyl)piperazin-1-yl]methanone Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)N1CCN(CCO)CC1 BUMLXUPLPMQWRK-UHFFFAOYSA-N 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• 230000002411 adverse Effects 0.000 description 2
• 235000010419 agar Nutrition 0.000 description 2
• 235000010443 alginic acid Nutrition 0.000 description 2
• 229920000615 alginic acid Polymers 0.000 description 2
• 125000005741 alkyl alkenyl group Chemical group 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 238000003782 apoptosis assay Methods 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• 239000000440 bentonite Substances 0.000 description 2
• 235000012216 bentonite Nutrition 0.000 description 2
• 229910000278 bentonite Inorganic materials 0.000 description 2
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
• 229940054066 benzamide antipsychotics Drugs 0.000 description 2
• 150000003936 benzamides Chemical class 0.000 description 2
• 235000019445 benzyl alcohol Nutrition 0.000 description 2
• 150000003938 benzyl alcohols Chemical class 0.000 description 2
• SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
• 125000002619 bicyclic group Chemical group 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
• 235000010216 calcium carbonate Nutrition 0.000 description 2
• 229910000019 calcium carbonate Inorganic materials 0.000 description 2
• 125000004432 carbon atom Chemical group C* 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 238000004113 cell culture Methods 0.000 description 2
• 239000007810 chemical reaction solvent Substances 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• 238000000576 coating method Methods 0.000 description 2
• 238000007796 conventional method Methods 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• 238000000354 decomposition reaction Methods 0.000 description 2
• SYZWSSNHPZXGML-UHFFFAOYSA-N dichloromethane;oxolane Chemical compound ClCCl.C1CCOC1 SYZWSSNHPZXGML-UHFFFAOYSA-N 0.000 description 2
• 235000005911 diet Nutrition 0.000 description 2
• 230000037213 diet Effects 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
• 239000012153 distilled water Substances 0.000 description 2
• 239000002552 dosage form Substances 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 239000000835 fiber Substances 0.000 description 2
• 239000000945 filler Substances 0.000 description 2
• 230000006870 function Effects 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 229930195733 hydrocarbon Natural products 0.000 description 2
• 150000002430 hydrocarbons Chemical class 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• 230000002401 inhibitory effect Effects 0.000 description 2
• 230000016507 interphase Effects 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 239000008297 liquid dosage form Substances 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 229910052751 metal Inorganic materials 0.000 description 2
• 239000002184 metal Substances 0.000 description 2
• 230000003547 miosis Effects 0.000 description 2
• 239000003226 mitogen Substances 0.000 description 2
• 238000012544 monitoring process Methods 0.000 description 2
• SKMCJUSFAIWLJG-UHFFFAOYSA-N n,n-diethyl-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CCN(CC)C(=O)C1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(I)C=C1C SKMCJUSFAIWLJG-UHFFFAOYSA-N 0.000 description 2
• HVMSAZSBXQHNDL-UHFFFAOYSA-N n-(2,3-dihydroxypropyl)-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCC(O)CO HVMSAZSBXQHNDL-UHFFFAOYSA-N 0.000 description 2
• DMGLLVWXKXWTIL-UHFFFAOYSA-N n-(3-hydroxypropyl)-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCCCO DMGLLVWXKXWTIL-UHFFFAOYSA-N 0.000 description 2
• HGXUEXUZCRYPLV-UHFFFAOYSA-N n-(cyclopropylmethoxy)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 HGXUEXUZCRYPLV-UHFFFAOYSA-N 0.000 description 2
• ZQRHTXJWJRVYGA-UHFFFAOYSA-N n-(cyclopropylmethoxy)-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCC1CC1 ZQRHTXJWJRVYGA-UHFFFAOYSA-N 0.000 description 2
• YGOLWJMMEQRTQY-UHFFFAOYSA-N n-[(5-chloro-2-fluorophenyl)methylidene]hydroxylamine Chemical compound ON=CC1=CC(Cl)=CC=C1F YGOLWJMMEQRTQY-UHFFFAOYSA-N 0.000 description 2
• SXKAKDLNOMWWGH-UHFFFAOYSA-N n-[2-[bis(2-hydroxyethyl)amino]ethyl]-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCCN(CCO)CCO SXKAKDLNOMWWGH-UHFFFAOYSA-N 0.000 description 2
• QFICQLHYTPHHHZ-UHFFFAOYSA-N n-[2-[bis(2-hydroxyethyl)amino]ethyl]-5-bromo-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCN(CCO)CCO QFICQLHYTPHHHZ-UHFFFAOYSA-N 0.000 description 2
• RESDNAOQJMJZLG-UHFFFAOYSA-N n-[2-[bis(2-hydroxyethyl)amino]ethyl]-5-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCN(CCO)CCO RESDNAOQJMJZLG-UHFFFAOYSA-N 0.000 description 2
• MFTVPZWSFTVKDW-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C MFTVPZWSFTVKDW-UHFFFAOYSA-N 0.000 description 2
• YNKVTTVVGYTRNM-UHFFFAOYSA-N n-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=CC=C1C(=O)NCCCN1CCN(CCO)CC1 YNKVTTVVGYTRNM-UHFFFAOYSA-N 0.000 description 2
• PMRYRJFGVUNXAW-UHFFFAOYSA-N n-benzyl-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCC1=CC=CC=C1 PMRYRJFGVUNXAW-UHFFFAOYSA-N 0.000 description 2
• VWFSFOHXGXBXFO-UHFFFAOYSA-N n-but-3-yn-2-yloxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound C#CC(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C VWFSFOHXGXBXFO-UHFFFAOYSA-N 0.000 description 2
• QVEIDMMXXOMGHZ-UHFFFAOYSA-N n-butyl-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCCCNC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C QVEIDMMXXOMGHZ-UHFFFAOYSA-N 0.000 description 2
• OMWXQRPRACBVAD-UHFFFAOYSA-N n-cyclobutyloxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOC1CCC1 OMWXQRPRACBVAD-UHFFFAOYSA-N 0.000 description 2
• ZHKTXUBWPSVDAP-UHFFFAOYSA-N n-cyclohexyl-2-(4-iodo-2-methylanilino)-5-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NC1CCCCC1 ZHKTXUBWPSVDAP-UHFFFAOYSA-N 0.000 description 2
• ZTMPSQKWWVAXQV-UHFFFAOYSA-N n-cyclohexyl-5-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NC1CCCCC1 ZTMPSQKWWVAXQV-UHFFFAOYSA-N 0.000 description 2
• NVABLGSLZIYASV-UHFFFAOYSA-N n-cyclopentyloxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOC1CCCC1 NVABLGSLZIYASV-UHFFFAOYSA-N 0.000 description 2
• ISERPJZNOJTETH-UHFFFAOYSA-N n-cyclopentyloxy-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOC1CCCC1 ISERPJZNOJTETH-UHFFFAOYSA-N 0.000 description 2
• MBSHGFWRDZJDMZ-UHFFFAOYSA-N n-ethoxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C MBSHGFWRDZJDMZ-UHFFFAOYSA-N 0.000 description 2
• CDOZIVZPNPKUPY-UHFFFAOYSA-N n-ethyl-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCNC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C CDOZIVZPNPKUPY-UHFFFAOYSA-N 0.000 description 2
• 239000002674 ointment Substances 0.000 description 2
• 239000004006 olive oil Substances 0.000 description 2
• 235000008390 olive oil Nutrition 0.000 description 2
• 230000000144 pharmacologic effect Effects 0.000 description 2
• 239000012071 phase Substances 0.000 description 2
• 239000011148 porous material Substances 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• 230000002265 prevention Effects 0.000 description 2
• 230000005522 programmed cell death Effects 0.000 description 2
• 230000002062 proliferating effect Effects 0.000 description 2
• 230000002035 prolonged effect Effects 0.000 description 2
• 229960004063 propylene glycol Drugs 0.000 description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
• 229920006395 saturated elastomer Polymers 0.000 description 2
• 150000003335 secondary amines Chemical class 0.000 description 2
• 230000036303 septic shock Effects 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 229910000104 sodium hydride Inorganic materials 0.000 description 2
• LWWPTYNMVLDNII-UHFFFAOYSA-M sodium;5-chloro-2-(4-iodo-2-methylanilino)benzoate Chemical compound [Na+].CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C([O-])=O LWWPTYNMVLDNII-UHFFFAOYSA-M 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 231100000331 toxic Toxicity 0.000 description 2
• 230000002588 toxic effect Effects 0.000 description 2
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
• 238000003828 vacuum filtration Methods 0.000 description 2
• 239000003981 vehicle Substances 0.000 description 2
• 239000001993 wax Substances 0.000 description 2
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 description 1
• 229940058015 1,3-butylene glycol Drugs 0.000 description 1
• MUUAQFJJUGVBGB-UHFFFAOYSA-N 1-bromo-2,3,4-trifluorobenzene Chemical compound FC1=CC=C(Br)C(F)=C1F MUUAQFJJUGVBGB-UHFFFAOYSA-N 0.000 description 1
• RJCGZNCCVKIBHO-UHFFFAOYSA-N 1-chloro-4-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1 RJCGZNCCVKIBHO-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• ZHMSIFGQMCBYIY-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-3,4,5-trifluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1Br ZHMSIFGQMCBYIY-UHFFFAOYSA-N 0.000 description 1
• BZJWSLFAFFNFIW-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1Br BZJWSLFAFFNFIW-UHFFFAOYSA-N 0.000 description 1
• XYYUOXLXTADKMW-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-4-fluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1Br XYYUOXLXTADKMW-UHFFFAOYSA-N 0.000 description 1
• AVIWCXSGNKPKKK-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-5-chloro-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1Br AVIWCXSGNKPKKK-UHFFFAOYSA-N 0.000 description 1
• KBJDNLWKCWKLMD-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-5-chloro-n-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C1CC1CONC(=O)C=1C=C(Cl)C(F)=C(F)C=1NC1=CC=C(I)C=C1Br KBJDNLWKCWKLMD-UHFFFAOYSA-N 0.000 description 1
• BWOZEHCSZGOGER-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-n-(cyclopropylmethoxy)-3,4,5-trifluorobenzamide Chemical compound C=1C=C(I)C=C(Br)C=1NC=1C(F)=C(F)C(F)=CC=1C(=O)NOCC1CC1 BWOZEHCSZGOGER-UHFFFAOYSA-N 0.000 description 1
• LZRKJVJJXDFWLG-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-n-(cyclopropylmethoxy)-4-fluorobenzamide Chemical compound C=1C=C(I)C=C(Br)C=1NC1=CC(F)=CC=C1C(=O)NOCC1CC1 LZRKJVJJXDFWLG-UHFFFAOYSA-N 0.000 description 1
• LHZVMSNGGDZKFO-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-n-(cyclopropylmethoxy)-4-nitrobenzamide Chemical compound C=1C=C(I)C=C(Br)C=1NC1=CC([N+](=O)[O-])=CC=C1C(=O)NOCC1CC1 LHZVMSNGGDZKFO-UHFFFAOYSA-N 0.000 description 1
• NMGPTKSLPIARAK-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-n-hydroxy-4-nitrobenzamide Chemical compound ONC(=O)C1=CC=C([N+]([O-])=O)C=C1NC1=CC=C(I)C=C1Br NMGPTKSLPIARAK-UHFFFAOYSA-N 0.000 description 1
• JHBIWAOIBNORTA-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4,5-trifluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl JHBIWAOIBNORTA-UHFFFAOYSA-N 0.000 description 1
• NXUSIIDZHWMSCV-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl NXUSIIDZHWMSCV-UHFFFAOYSA-N 0.000 description 1
• YVSLCRVTJGUKSV-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-(cyclopropylmethoxy)-3,4,5-trifluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC=1C(F)=C(F)C(F)=CC=1C(=O)NOCC1CC1 YVSLCRVTJGUKSV-UHFFFAOYSA-N 0.000 description 1
• DVENTWJICBBDAJ-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-(cyclopropylmethoxy)-4-fluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=CC(F)=CC=C1C(=O)NOCC1CC1 DVENTWJICBBDAJ-UHFFFAOYSA-N 0.000 description 1
• BOWUZVRUZUWLAM-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-ethoxy-4-nitrobenzamide Chemical compound CCONC(=O)C1=CC=C([N+]([O-])=O)C=C1NC1=CC=C(I)C=C1Cl BOWUZVRUZUWLAM-UHFFFAOYSA-N 0.000 description 1
• SHNRDYXLGNJCOC-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-hydroxy-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NO)C(NC=2C(=CC(I)=CC=2)Cl)=C1 SHNRDYXLGNJCOC-UHFFFAOYSA-N 0.000 description 1
• KIUBJCBWGNLTFG-UHFFFAOYSA-N 2-(2-fluoro-4-iodoanilino)-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(I)C=C1F KIUBJCBWGNLTFG-UHFFFAOYSA-N 0.000 description 1
• UOPHVVWHOCFXFI-UHFFFAOYSA-N 2-(2-fluoro-4-iodoanilino)-n-hydroxy-4-nitrobenzamide Chemical compound ONC(=O)C1=CC=C([N+]([O-])=O)C=C1NC1=CC=C(I)C=C1F UOPHVVWHOCFXFI-UHFFFAOYSA-N 0.000 description 1
• IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
• UPPHUQVTOWZROO-UHFFFAOYSA-N 2-(3-chloro-4-iodo-2-methylanilino)-4-fluorobenzoic acid Chemical compound CC1=C(Cl)C(I)=CC=C1NC1=CC(F)=CC=C1C(O)=O UPPHUQVTOWZROO-UHFFFAOYSA-N 0.000 description 1
• BYNKDEUDKDVPPJ-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-methylprop-2-enoxy)benzamide Chemical compound CC(=C)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C BYNKDEUDKDVPPJ-UHFFFAOYSA-N 0.000 description 1
• YDOWUWRHGYWZHT-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(furan-3-ylmethoxy)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1=COC=C1 YDOWUWRHGYWZHT-UHFFFAOYSA-N 0.000 description 1
• FSCLSXYRUIVDGC-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(pyridin-4-ylmethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCC1=CC=NC=C1 FSCLSXYRUIVDGC-UHFFFAOYSA-N 0.000 description 1
• IXBSECQHCYLYAJ-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-4-fluoro-n-hydroxybenzamide Chemical compound CC1=CC(Br)=CC=C1NC1=CC(F)=CC=C1C(=O)NO IXBSECQHCYLYAJ-UHFFFAOYSA-N 0.000 description 1
• BHEYIPCYQCTTAR-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 BHEYIPCYQCTTAR-UHFFFAOYSA-N 0.000 description 1
• OTMQSOXSEGNQHJ-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-3-methyl-5-nitro-n-pyridin-4-ylbenzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(C)C=C([N+]([O-])=O)C=C1C(=O)NC1=CC=NC=C1 OTMQSOXSEGNQHJ-UHFFFAOYSA-N 0.000 description 1
• XVLPEYUVEHKUBW-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-nitro-n-(2-piperidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCCN1CCCCC1 XVLPEYUVEHKUBW-UHFFFAOYSA-N 0.000 description 1
• FHXQAXYOKQYKHH-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=CC=C1C(O)=O FHXQAXYOKQYKHH-UHFFFAOYSA-N 0.000 description 1
• VVTCLTONLVZMDI-UHFFFAOYSA-N 2-anilino-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=CC=C1NC1=CC=CC=C1 VVTCLTONLVZMDI-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• DAHWLPNSVWRDFB-UHFFFAOYSA-N 2-chloro-6-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=CC(Cl)=C1C(O)=O DAHWLPNSVWRDFB-UHFFFAOYSA-N 0.000 description 1
• CZDVKBNPCLSXTF-UHFFFAOYSA-N 2-fluoro-6-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=CC(F)=C1C(O)=O CZDVKBNPCLSXTF-UHFFFAOYSA-N 0.000 description 1
• GKSQCZBTWKAFIV-UHFFFAOYSA-N 2-phenylethyl 2-(4-iodo-2-methylanilino)-5-nitrobenzoate Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)OCCC1=CC=CC=C1 GKSQCZBTWKAFIV-UHFFFAOYSA-N 0.000 description 1
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• PYEBOHZEONEOFB-UHFFFAOYSA-N 3,4,5-trifluoro-2-(2-fluoro-4-iodoanilino)-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1F PYEBOHZEONEOFB-UHFFFAOYSA-N 0.000 description 1
• CCYWUMAAAUNDJX-UHFFFAOYSA-N 3,4,5-trifluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C(=O)NO CCYWUMAAAUNDJX-UHFFFAOYSA-N 0.000 description 1
• IPVITVKNQFEBEA-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F IPVITVKNQFEBEA-UHFFFAOYSA-N 0.000 description 1
• HDLXUSUTCIBXQZ-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-methylprop-2-enoxy)benzamide Chemical compound CC(=C)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C HDLXUSUTCIBXQZ-UHFFFAOYSA-N 0.000 description 1
• SXAYAMZOIRULRY-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCN1CCOCC1 SXAYAMZOIRULRY-UHFFFAOYSA-N 0.000 description 1
• ILKRGOONQZFQPI-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(3-methyl-5-phenylpent-2-en-4-ynoxy)benzamide Chemical compound C=1C=CC=CC=1C#CC(C)=CCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C ILKRGOONQZFQPI-UHFFFAOYSA-N 0.000 description 1
• UYUHIMXYEAWUTA-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(pyridin-4-ylmethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCC1=CC=NC=C1 UYUHIMXYEAWUTA-UHFFFAOYSA-N 0.000 description 1
• YKZJWZFIUUQRCQ-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-methoxybenzamide Chemical compound CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C YKZJWZFIUUQRCQ-UHFFFAOYSA-N 0.000 description 1
• XKKPRURDQYWGIU-UHFFFAOYSA-N 3,4-difluoro-n-(3-hydroxypropyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCCO XKKPRURDQYWGIU-UHFFFAOYSA-N 0.000 description 1
• OEYRWOJRMOBKSM-UHFFFAOYSA-N 3,4-difluoro-n-[3-(2-fluorophenyl)prop-2-ynoxy]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC#CC1=CC=CC=C1F OEYRWOJRMOBKSM-UHFFFAOYSA-N 0.000 description 1
• ZBAQISAJHKDXIH-UHFFFAOYSA-N 3,4-difluoro-n-[3-(3-fluorophenyl)prop-2-ynoxy]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC#CC1=CC=CC(F)=C1 ZBAQISAJHKDXIH-UHFFFAOYSA-N 0.000 description 1
• FPENCTDAQQQKNY-UHFFFAOYSA-N 3,4-difluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(F)=C1 FPENCTDAQQQKNY-UHFFFAOYSA-N 0.000 description 1
• RLFNSOUBVMLCHS-UHFFFAOYSA-N 3-chloro-2-(2-chloro-4-iodoanilino)benzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1NC1=CC=C(I)C=C1Cl RLFNSOUBVMLCHS-UHFFFAOYSA-N 0.000 description 1
• HKDQXFITKMWGCA-UHFFFAOYSA-N 3-fluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C=CC=C1C(O)=O HKDQXFITKMWGCA-UHFFFAOYSA-N 0.000 description 1
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
• 125000006192 3-phenylprop-2-enyl group Chemical group [H]\C(=C(\[H])C([H])([H])*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• OFJHKJAWPYMKAO-UHFFFAOYSA-N 4-bromo-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(Br)=CC=C1C(=O)NOCC1=CC=CC=C1 OFJHKJAWPYMKAO-UHFFFAOYSA-N 0.000 description 1
• OEDQBUOUDGINPB-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1F OEDQBUOUDGINPB-UHFFFAOYSA-N 0.000 description 1
• BCZRQTHOUDQRMG-UHFFFAOYSA-N 4-fluoro-2-(3-fluoro-4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=C(F)C(I)=CC=C1NC1=CC(F)=CC=C1C(O)=O BCZRQTHOUDQRMG-UHFFFAOYSA-N 0.000 description 1
• HUNHDWQNBANZPB-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCN1CCOCC1 HUNHDWQNBANZPB-UHFFFAOYSA-N 0.000 description 1
• IURDPGNSPNCXAT-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCCCN1CCCCC1 IURDPGNSPNCXAT-UHFFFAOYSA-N 0.000 description 1
• SQKWOEQAJIDRHG-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(pyridin-4-ylmethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NCC1=CC=NC=C1 SQKWOEQAJIDRHG-UHFFFAOYSA-N 0.000 description 1
• JDMFRBBBOJOMDZ-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-propan-2-yloxybenzamide Chemical compound CC(C)ONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C JDMFRBBBOJOMDZ-UHFFFAOYSA-N 0.000 description 1
• OGHFGSSUBKOEFE-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-propoxybenzamide Chemical compound CCCONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C OGHFGSSUBKOEFE-UHFFFAOYSA-N 0.000 description 1
• FHCLXSBNNQGXFD-UHFFFAOYSA-N 4-fluoro-2-[(4-iodo-5,6,6-trimethylcyclohexa-2,4-dien-1-yl)amino]benzoic acid Chemical compound CC1(C)C(C)=C(I)C=CC1NC1=CC(F)=CC=C1C(O)=O FHCLXSBNNQGXFD-UHFFFAOYSA-N 0.000 description 1
• JBJLRROXDYRUHQ-UHFFFAOYSA-N 4-fluoro-n-hydroxy-2-(2-methylanilino)benzamide Chemical compound CC1=CC=CC=C1NC1=CC(F)=CC=C1C(=O)NO JBJLRROXDYRUHQ-UHFFFAOYSA-N 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• CXSHZTDJFXMXPL-UHFFFAOYSA-N 4-iodo-6-methyl-4-nitro-6-(2h-tetrazol-5-yl)cyclohex-2-en-1-amine Chemical compound N1=NNN=C1C1(C)CC(I)([N+]([O-])=O)C=CC1N CXSHZTDJFXMXPL-UHFFFAOYSA-N 0.000 description 1
• WDCVVUHGOMOJNR-UHFFFAOYSA-N 4-methoxy-n-(4-methoxyphenyl)-3-nitrobenzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=C(OC)C([N+]([O-])=O)=C1 WDCVVUHGOMOJNR-UHFFFAOYSA-N 0.000 description 1
• XQIATTAAVBLNAN-UHFFFAOYSA-N 5-bromo-2,3,4-trifluorobenzoic acid Chemical compound OC(=O)C1=CC(Br)=C(F)C(F)=C1F XQIATTAAVBLNAN-UHFFFAOYSA-N 0.000 description 1
• RPWNJSYAWBWAFW-UHFFFAOYSA-N 5-bromo-2-(2-bromo-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Br RPWNJSYAWBWAFW-UHFFFAOYSA-N 0.000 description 1
• ZMFXUELOZZCDTA-UHFFFAOYSA-N 5-bromo-2-(2-bromo-4-iodoanilino)-n-ethoxy-3,4-difluorobenzamide Chemical compound CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Br ZMFXUELOZZCDTA-UHFFFAOYSA-N 0.000 description 1
• CTKGCVOMHALRNE-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-(2-piperazin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCN1CCNCC1 CTKGCVOMHALRNE-UHFFFAOYSA-N 0.000 description 1
• LUAWFZQWIXYGPQ-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1F LUAWFZQWIXYGPQ-UHFFFAOYSA-N 0.000 description 1
• QTDDKGUPEPKNIP-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-piperidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCN1CCCCC1 QTDDKGUPEPKNIP-UHFFFAOYSA-N 0.000 description 1
• NKRZYDJKGYMRDY-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(3-methylbut-2-enoxy)benzamide Chemical compound CC(C)=CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C NKRZYDJKGYMRDY-UHFFFAOYSA-N 0.000 description 1
• CYHKFEHMDJDUCY-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(pyridin-3-ylmethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1=CC=CN=C1 CYHKFEHMDJDUCY-UHFFFAOYSA-N 0.000 description 1
• XJWYMYUEQFWKPG-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(thiophen-2-ylmethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1=CC=CS1 XJWYMYUEQFWKPG-UHFFFAOYSA-N 0.000 description 1
• ZXCWXANNFFPFMA-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-[3-(3-methoxyphenyl)prop-2-ynoxy]benzamide Chemical compound COC1=CC=CC(C#CCONC(=O)C=2C(=C(F)C(F)=C(Br)C=2)NC=2C(=CC(I)=CC=2)C)=C1 ZXCWXANNFFPFMA-UHFFFAOYSA-N 0.000 description 1
• JDYMILCDQZFLCK-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-prop-2-ynoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC#C JDYMILCDQZFLCK-UHFFFAOYSA-N 0.000 description 1
• OKRDHHWCFHEDRY-UHFFFAOYSA-N 5-bromo-3,4-difluoro-n-(furan-3-ylmethoxy)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1=COC=C1 OKRDHHWCFHEDRY-UHFFFAOYSA-N 0.000 description 1
• PHJXBTSQFDDWJS-UHFFFAOYSA-N 5-bromo-n-(cyclopropylmethoxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound FC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1CC1 PHJXBTSQFDDWJS-UHFFFAOYSA-N 0.000 description 1
• JREYCDFOVXBKQM-UHFFFAOYSA-N 5-bromo-n-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCCN1CCN(CCO)CC1 JREYCDFOVXBKQM-UHFFFAOYSA-N 0.000 description 1
• BPBVLRKSHJEHCJ-UHFFFAOYSA-N 5-bromo-n-butoxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C BPBVLRKSHJEHCJ-UHFFFAOYSA-N 0.000 description 1
• MKRVIYRPNNYISB-UHFFFAOYSA-N 5-chloro-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl MKRVIYRPNNYISB-UHFFFAOYSA-N 0.000 description 1
• MVHVCAWSOBHXIJ-UHFFFAOYSA-N 5-chloro-2-(2-chloro-4-iodoanilino)-3,4-difluorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl MVHVCAWSOBHXIJ-UHFFFAOYSA-N 0.000 description 1
• DESOLFCZYNVVHJ-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCN1CCCC1 DESOLFCZYNVVHJ-UHFFFAOYSA-N 0.000 description 1
• STJGIOUQRPNOBU-UHFFFAOYSA-N 5-chloro-3,4-difluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Cl)C=C1C(O)=O STJGIOUQRPNOBU-UHFFFAOYSA-N 0.000 description 1
• RCKXWJPGNUQSAX-UHFFFAOYSA-N 5-chloro-3,4-difluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Cl)C=C1C(=O)NO RCKXWJPGNUQSAX-UHFFFAOYSA-N 0.000 description 1
• HVYIBSVDNMZNKR-UHFFFAOYSA-N 5-chloro-n-(cyclopropylmethoxy)-3,4-difluoro-2-(4-iodoanilino)benzamide Chemical compound C=1C=C(I)C=CC=1NC1=C(F)C(F)=C(Cl)C=C1C(=O)NOCC1CC1 HVYIBSVDNMZNKR-UHFFFAOYSA-N 0.000 description 1
• CLAKDMJHMLECDQ-UHFFFAOYSA-N 5-chloro-n-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCCN1CCN(CCO)CC1 CLAKDMJHMLECDQ-UHFFFAOYSA-N 0.000 description 1
• PDFLHOZPRYZDDW-UHFFFAOYSA-N 5-chloro-n-hydroxy-2-(4-iodo-2-methylanilino)-n-methylbenzamide Chemical compound CN(O)C(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C PDFLHOZPRYZDDW-UHFFFAOYSA-N 0.000 description 1
• LTGBDYINTUIVIR-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-(oxan-2-yloxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NOC1OCCCC1 LTGBDYINTUIVIR-UHFFFAOYSA-N 0.000 description 1
• PPBHPHGQDGGSHX-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(O)=O PPBHPHGQDGGSHX-UHFFFAOYSA-N 0.000 description 1
• KDWCTADZBWWBLF-UHFFFAOYSA-N 5-fluoro-n-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCCN1CCN(CCO)CC1 KDWCTADZBWWBLF-UHFFFAOYSA-N 0.000 description 1
• FUJLYVVUOAQPRQ-UHFFFAOYSA-N 5-fluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NO FUJLYVVUOAQPRQ-UHFFFAOYSA-N 0.000 description 1
• GGZZISOUXJHYOY-UHFFFAOYSA-N 8-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1O GGZZISOUXJHYOY-UHFFFAOYSA-N 0.000 description 1
• 102000007469 Actins Human genes 0.000 description 1
• 108010085238 Actins Proteins 0.000 description 1
• 239000005995 Aluminium silicate Substances 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• XGRVWKWWJMDGTJ-UHFFFAOYSA-N CC1=C(C=CC(=C1)I)NC2=C(C=CC(=C2C)F)C(=O)NC3=CC=NC=C3 Chemical compound CC1=C(C=CC(=C1)I)NC2=C(C=CC(=C2C)F)C(=O)NC3=CC=NC=C3 XGRVWKWWJMDGTJ-UHFFFAOYSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 241000283707 Capra Species 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 108090000695 Cytokines Proteins 0.000 description 1
• 102000004127 Cytokines Human genes 0.000 description 1
• 102000010831 Cytoskeletal Proteins Human genes 0.000 description 1
• 108010037414 Cytoskeletal Proteins Proteins 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• 102100023275 Dual specificity mitogen-activated protein kinase kinase 3 Human genes 0.000 description 1
• 108030004793 Dual-specificity kinases Proteins 0.000 description 1
• 102000001301 EGF receptor Human genes 0.000 description 1
• 108060006698 EGF receptor Proteins 0.000 description 1
• 239000004097 EU approved flavor enhancer Substances 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101001115394 Homo sapiens Dual specificity mitogen-activated protein kinase kinase 3 Proteins 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• 206010020772 Hypertension Diseases 0.000 description 1
• 208000001953 Hypotension Diseases 0.000 description 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
• 206010022095 Injection Site reaction Diseases 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 241000124008 Mammalia Species 0.000 description 1
• 240000003183 Manihot esculenta Species 0.000 description 1
• 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• UHAXDAKQGVISBZ-UHFFFAOYSA-N N-(cyclopropylmethoxy)-3,4,5-trifluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C(=O)NOCC1CC1 UHAXDAKQGVISBZ-UHFFFAOYSA-N 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• 108010009711 Phalloidine Proteins 0.000 description 1
• 102000014750 Phosphorylase Kinase Human genes 0.000 description 1
• 108010064071 Phosphorylase Kinase Proteins 0.000 description 1
• 102000009097 Phosphorylases Human genes 0.000 description 1
• 108010073135 Phosphorylases Proteins 0.000 description 1
• 108091000080 Phosphotransferase Proteins 0.000 description 1
• 239000004698 Polyethylene Substances 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 102000001253 Protein Kinase Human genes 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• 102100033479 RAF proto-oncogene serine/threonine-protein kinase Human genes 0.000 description 1
• 229940078123 Ras inhibitor Drugs 0.000 description 1
• 101100017604 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) HOR7 gene Proteins 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• SSZBUIDZHHWXNJ-UHFFFAOYSA-N Stearinsaeure-hexadecylester Natural products CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCC SSZBUIDZHHWXNJ-UHFFFAOYSA-N 0.000 description 1
• 241000282887 Suidae Species 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 102000040945 Transcription factor Human genes 0.000 description 1
• 108091023040 Transcription factor Proteins 0.000 description 1
• 229940123468 Transferase inhibitor Drugs 0.000 description 1
• 108091000117 Tyrosine 3-Monooxygenase Proteins 0.000 description 1
• 102000048218 Tyrosine 3-monooxygenases Human genes 0.000 description 1
• 229940122803 Vinca alkaloid Drugs 0.000 description 1
• 206010047700 Vomiting Diseases 0.000 description 1
• 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
• PNWJMZMIJSAVRR-UHFFFAOYSA-N [2-(4-iodo-2-methylanilino)-5-nitrophenyl]methanol Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1CO PNWJMZMIJSAVRR-UHFFFAOYSA-N 0.000 description 1
• NCFUTJOYXRJVMX-UHFFFAOYSA-N [5-fluoro-2-(4-iodo-2-methylanilino)phenyl]-(3-hydroxypyrrolidin-1-yl)methanone Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)N1CC(O)CC1 NCFUTJOYXRJVMX-UHFFFAOYSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 239000003655 absorption accelerator Substances 0.000 description 1
• 150000001242 acetic acid derivatives Chemical class 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 239000003463 adsorbent Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 208000026935 allergic disease Diseases 0.000 description 1
• 208000030961 allergic reaction Diseases 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• 239000003708 ampul Substances 0.000 description 1
• 150000001448 anilines Chemical class 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 230000001093 anti-cancer Effects 0.000 description 1
• 229940044684 anti-microtubule agent Drugs 0.000 description 1
• 239000003429 antifungal agent Substances 0.000 description 1
• 229940121375 antifungal agent Drugs 0.000 description 1
• 239000000427 antigen Substances 0.000 description 1
• 229940034982 antineoplastic agent Drugs 0.000 description 1
• 239000002246 antineoplastic agent Substances 0.000 description 1
• 239000008365 aqueous carrier Substances 0.000 description 1
• 239000006286 aqueous extract Substances 0.000 description 1
• 238000000429 assembly Methods 0.000 description 1
• 230000000712 assembly Effects 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 229960002903 benzyl benzoate Drugs 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 230000036760 body temperature Effects 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 229910000085 borane Inorganic materials 0.000 description 1
• UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
• 208000006218 bradycardia Diseases 0.000 description 1
• 230000036471 bradycardia Effects 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 239000006172 buffering agent Substances 0.000 description 1
• 235000019437 butane-1,3-diol Nutrition 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• 230000004611 cancer cell death Effects 0.000 description 1
• 239000001569 carbon dioxide Substances 0.000 description 1
• 229910002092 carbon dioxide Inorganic materials 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 239000004359 castor oil Substances 0.000 description 1
• 235000019438 castor oil Nutrition 0.000 description 1
• 125000002091 cationic group Chemical group 0.000 description 1
• 230000022131 cell cycle Effects 0.000 description 1
• 230000030833 cell death Effects 0.000 description 1
• 230000003915 cell function Effects 0.000 description 1
• 229960000541 cetyl alcohol Drugs 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
• 150000001860 citric acid derivatives Chemical class 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 210000001072 colon Anatomy 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 235000005687 corn oil Nutrition 0.000 description 1
• 239000002285 corn oil 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
• ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229960000935 dehydrated alcohol Drugs 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• 239000007933 dermal patch Substances 0.000 description 1
• PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
• 125000005265 dialkylamine group Chemical group 0.000 description 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
• 239000000539 dimer Substances 0.000 description 1
• ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
• 201000010099 disease Diseases 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 230000005059 dormancy Effects 0.000 description 1
• 239000008298 dragée Substances 0.000 description 1
• 239000006196 drop Substances 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 238000005538 encapsulation Methods 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 238000001952 enzyme assay Methods 0.000 description 1
• 125000004185 ester group Chemical group 0.000 description 1
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
• 239000012259 ether extract Substances 0.000 description 1
• ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
• 229940093499 ethyl acetate Drugs 0.000 description 1
• LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
• 229940093471 ethyl oleate Drugs 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 239000003885 eye ointment Substances 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 1
• 125000006379 fluoropyridyl group Chemical group 0.000 description 1
• 235000019264 food flavour enhancer Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 239000003205 fragrance Substances 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
• LTPYMDGHUGZUBZ-UHFFFAOYSA-N furo[3,2-b]pyridin-2-amine Chemical compound C1=CC=C2OC(N)=CC2=N1 LTPYMDGHUGZUBZ-UHFFFAOYSA-N 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• 125000005612 glucoheptonate group Chemical group 0.000 description 1
• 235000001727 glucose Nutrition 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
• SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
• 239000003102 growth factor Substances 0.000 description 1
• 239000001963 growth medium Substances 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 239000010460 hemp oil Substances 0.000 description 1
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
• XBFMJHQFVWWFLA-UHFFFAOYSA-N hexane;pentane Chemical compound CCCCC.CCCCCC XBFMJHQFVWWFLA-UHFFFAOYSA-N 0.000 description 1
• 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
• 150000003840 hydrochlorides Chemical class 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 230000009610 hypersensitivity Effects 0.000 description 1
• 230000036543 hypotension Effects 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 239000003701 inert diluent Substances 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 239000013067 intermediate product Substances 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 239000012948 isocyanate Substances 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
• 230000002147 killing effect Effects 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 208000020816 lung neoplasm Diseases 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 150000002688 maleic acid derivatives Chemical class 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 230000035773 mitosis phase Effects 0.000 description 1
• 230000000394 mitotic effect Effects 0.000 description 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
• CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• TYHIZTJRCMNBDH-UHFFFAOYSA-N n-(cyclopropylmethoxy)-2-(2-fluoro-4-iodoanilino)-4-nitrobenzamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=CC([N+](=O)[O-])=CC=C1C(=O)NOCC1CC1 TYHIZTJRCMNBDH-UHFFFAOYSA-N 0.000 description 1
• RJPCFXZBKMJDCK-UHFFFAOYSA-N n-(cyclopropylmethoxy)-2-(4-iodo-2-methylanilino)-4-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC([N+]([O-])=O)=CC=C1C(=O)NOCC1CC1 RJPCFXZBKMJDCK-UHFFFAOYSA-N 0.000 description 1
• PNTKSRDALUNXIE-UHFFFAOYSA-N n-(cyclopropylmethoxy)-3,4,5-trifluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound C=1C=C(I)C=C(F)C=1NC=1C(F)=C(F)C(F)=CC=1C(=O)NOCC1CC1 PNTKSRDALUNXIE-UHFFFAOYSA-N 0.000 description 1
• DQHARHQBVRLSQS-UHFFFAOYSA-N n-(cyclopropylmethoxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 DQHARHQBVRLSQS-UHFFFAOYSA-N 0.000 description 1
• UESARFTYTCYCQK-UHFFFAOYSA-N n-(cyclopropylmethoxy)-4-fluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound C=1C=C(I)C=C(F)C=1NC1=CC(F)=CC=C1C(=O)NOCC1CC1 UESARFTYTCYCQK-UHFFFAOYSA-N 0.000 description 1
• ABMFCKSENBKLRK-UHFFFAOYSA-N n-[2-[bis(2-hydroxyethyl)amino]ethyl]-5-chloro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCN(CCO)CCO ABMFCKSENBKLRK-UHFFFAOYSA-N 0.000 description 1
• GSUQGEQHBNXARP-UHFFFAOYSA-N n-[2-[di(propan-2-yl)amino]ethyl]-5-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC(C)N(C(C)C)CCNC(=O)C1=CC(F)=CC=C1NC1=CC=C(I)C=C1C GSUQGEQHBNXARP-UHFFFAOYSA-N 0.000 description 1
• GEHFGHKNJRMMLE-UHFFFAOYSA-N n-but-2-enoxy-4-fluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC=CCONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1C GEHFGHKNJRMMLE-UHFFFAOYSA-N 0.000 description 1
• FKURQLBTBBUUAQ-UHFFFAOYSA-N n-cyclohexyl-5-iodo-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(=O)NC1CCCCC1 FKURQLBTBBUUAQ-UHFFFAOYSA-N 0.000 description 1
• IVKQAKIJQNIBIO-UHFFFAOYSA-N n-hydroxy-2-(4-iodo-2-methylanilino)-4-nitrobenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC([N+]([O-])=O)=CC=C1C(=O)NO IVKQAKIJQNIBIO-UHFFFAOYSA-N 0.000 description 1
• QAMBBWKIAJFFRF-UHFFFAOYSA-N n-hydroxy-2-(4-iodoanilino)benzamide Chemical class ONC(=O)C1=CC=CC=C1NC1=CC=C(I)C=C1 QAMBBWKIAJFFRF-UHFFFAOYSA-N 0.000 description 1
• FOGKWZGOCWAFPT-UHFFFAOYSA-N n-propan-2-yloxyethanamine Chemical compound CCNOC(C)C FOGKWZGOCWAFPT-UHFFFAOYSA-N 0.000 description 1
• 125000005487 naphthalate group Chemical group 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 229940097496 nasal spray Drugs 0.000 description 1
• 239000007922 nasal spray Substances 0.000 description 1
• 229930014626 natural product Natural products 0.000 description 1
• 229940086322 navelbine Drugs 0.000 description 1
• 150000002823 nitrates Chemical class 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• 125000004433 nitrogen atom Chemical group N* 0.000 description 1
• 125000006574 non-aromatic ring group Chemical group 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 239000012457 nonaqueous media Substances 0.000 description 1
• 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 229940127084 other anti-cancer agent Drugs 0.000 description 1
• 150000003891 oxalate salts Chemical class 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
• 239000008177 pharmaceutical agent Substances 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
• 235000021317 phosphate Nutrition 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 230000026731 phosphorylation Effects 0.000 description 1
• 238000006366 phosphorylation reaction Methods 0.000 description 1
• 102000020233 phosphotransferase Human genes 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 229920000573 polyethylene Polymers 0.000 description 1
• 229920005862 polyol Polymers 0.000 description 1
• 150000003077 polyols Chemical class 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 235000015320 potassium carbonate Nutrition 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
• 108060006633 protein kinase Proteins 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 125000003226 pyrazolyl 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
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 238000011084 recovery Methods 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 230000009703 regulation of cell differentiation Effects 0.000 description 1
• 230000025053 regulation of cell proliferation Effects 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 208000037803 restenosis Diseases 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• QTDJRZSPOPELPU-UHFFFAOYSA-N s-(2-phenylethyl) 5-chloro-2-(4-iodo-2-methylanilino)benzenecarbothioate Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)SCCC1=CC=CC=C1 QTDJRZSPOPELPU-UHFFFAOYSA-N 0.000 description 1
• QCZYEGJADPODIL-UHFFFAOYSA-N s-(2-phenylethyl) 5-fluoro-2-(4-iodo-2-methylanilino)benzenecarbothioate Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)SCCC1=CC=CC=C1 QCZYEGJADPODIL-UHFFFAOYSA-N 0.000 description 1
• MZWWXGJDHZGDNB-UHFFFAOYSA-N s-benzyl 2-(4-iodo-2-methylanilino)-5-nitrobenzenecarbothioate Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)SCC1=CC=CC=C1 MZWWXGJDHZGDNB-UHFFFAOYSA-N 0.000 description 1
• NUSWDIDPAXABIZ-UHFFFAOYSA-N s-benzyl 5-bromo-2-(4-iodo-2-methylanilino)benzenecarbothioate Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)SCC1=CC=CC=C1 NUSWDIDPAXABIZ-UHFFFAOYSA-N 0.000 description 1
• ARKSUULDABGYFK-UHFFFAOYSA-N s-benzyl 5-chloro-2-(4-iodo-2-methylanilino)benzenecarbothioate Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)SCC1=CC=CC=C1 ARKSUULDABGYFK-UHFFFAOYSA-N 0.000 description 1
• WKBDDXZGUFGFIP-UHFFFAOYSA-N s-benzyl 5-fluoro-2-(4-iodo-2-methylanilino)benzenecarbothioate Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)SCC1=CC=CC=C1 WKBDDXZGUFGFIP-UHFFFAOYSA-N 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 239000008159 sesame oil Substances 0.000 description 1
• 235000011803 sesame oil Nutrition 0.000 description 1
• 230000011664 signaling Effects 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
• 235000012239 silicon dioxide Nutrition 0.000 description 1
• 239000011734 sodium Substances 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 239000004334 sorbic acid Substances 0.000 description 1
• 235000010199 sorbic acid Nutrition 0.000 description 1
• 229940075582 sorbic acid Drugs 0.000 description 1
• 235000010356 sorbitol Nutrition 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 238000010186 staining Methods 0.000 description 1
• 150000003431 steroids Chemical class 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 125000003107 substituted aryl group Chemical group 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 150000003890 succinate salts Chemical class 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 238000001308 synthesis method Methods 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 150000003892 tartrate salts Chemical class 0.000 description 1
• 229940063683 taxotere Drugs 0.000 description 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
• KHVCOYGKHDJPBZ-WDCZJNDASA-N tetrahydrooxazine Chemical compound OC[C@H]1ONC[C@@H](O)[C@@H]1O KHVCOYGKHDJPBZ-WDCZJNDASA-N 0.000 description 1
• 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
• 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 125000005490 tosylate group Chemical group 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 239000003558 transferase inhibitor Substances 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• 210000004881 tumor cell Anatomy 0.000 description 1
• NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
• 229960000922 vinflunine Drugs 0.000 description 1
• CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
• 229960002166 vinorelbine tartrate Drugs 0.000 description 1
• GBABOYUKABKIAF-IWWDSPBFSA-N vinorelbinetartrate Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC(C23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IWWDSPBFSA-N 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1