NZ518726A - Method of treating or inhibiting neutrophil chemotaxis by administering a mek inhibitor - Google Patents

Info

Publication number

NZ518726A

NZ518726A NZ518726A NZ51872602A NZ518726A NZ 518726 A NZ518726 A NZ 518726A NZ 518726 A NZ518726 A NZ 518726A NZ 51872602 A NZ51872602 A NZ 51872602A NZ 518726 A NZ518726 A NZ 518726A

Authority

NZ

New Zealand

Prior art keywords

phenylamino

benzamide

iodo

methyl

difluoro

Prior art date

2001-05-09

Links

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• Global Dossier
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• 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 title claims abstract description 55
• 229940124647 MEK inhibitor Drugs 0.000 title claims abstract description 51
• 230000002401 inhibitory effect Effects 0.000 title claims abstract description 13
• 238000000034 method Methods 0.000 title claims description 34
• 230000011242 neutrophil chemotaxis Effects 0.000 title claims description 15
• 210000000440 neutrophil Anatomy 0.000 claims abstract description 61
• 230000005012 migration Effects 0.000 claims abstract description 25
• 238000013508 migration Methods 0.000 claims abstract description 25
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 claims abstract description 23
• 239000012828 PI3K inhibitor Substances 0.000 claims abstract description 21
• 201000010099 disease Diseases 0.000 claims abstract description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
• 230000001404 mediated effect Effects 0.000 claims abstract description 12
• 239000003814 drug Substances 0.000 claims abstract description 7
• 201000003883 Cystic fibrosis Diseases 0.000 claims abstract description 5
• 230000001154 acute effect Effects 0.000 claims abstract description 5
• 238000004519 manufacturing process Methods 0.000 claims abstract description 5
• GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims abstract description 4
• 208000033116 Asbestos intoxication Diseases 0.000 claims abstract description 4
• 206010014561 Emphysema Diseases 0.000 claims abstract description 4
• 208000037487 Endotoxemia Diseases 0.000 claims abstract description 4
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims abstract description 4
• 206010063837 Reperfusion injury Diseases 0.000 claims abstract description 4
• 206010040047 Sepsis Diseases 0.000 claims abstract description 4
• 206010003441 asbestosis Diseases 0.000 claims abstract description 4
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims abstract description 4
• 208000012947 ischemia reperfusion injury Diseases 0.000 claims abstract description 4
• 208000023504 respiratory system disease Diseases 0.000 claims abstract description 4
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 4
• -1 [5-Fluoro-2-(4-iodo-2-methyl-phenylamino)-phenyl]-(3-hydroxy-pyrrolidin-l-yl)- Chemical class 0.000 claims description 118
• 125000000217 alkyl group Chemical group 0.000 claims description 90
• 150000001875 compounds Chemical class 0.000 claims description 80
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 239000001257 hydrogen Substances 0.000 claims description 46
• 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 34
• 125000003545 alkoxy group Chemical group 0.000 claims description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000005843 halogen group Chemical group 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 17
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 150000001408 amides Chemical class 0.000 claims description 15
• 150000002148 esters Chemical class 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 239000005711 Benzoic acid Substances 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 12
• 125000004104 aryloxy group Chemical group 0.000 claims description 12
• 125000004122 cyclic group Chemical group 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 229940002612 prodrug Drugs 0.000 claims description 9
• 239000000651 prodrug Substances 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
• 229910052731 fluorine Chemical group 0.000 claims description 8
• 239000011737 fluorine Chemical group 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
• SUDAHWBOROXANE-SECBINFHSA-N PD 0325901 Chemical compound OC[C@@H](O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F SUDAHWBOROXANE-SECBINFHSA-N 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 7
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 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 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
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 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 claims 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 claims 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 claims description 4
• 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 claims description 4
• 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 claims 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 claims 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 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• IGVMHOOQGPQIMZ-UHFFFAOYSA-N n-(2-anilinoethoxy)-2-(2-chloro-4-iodoanilino)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCCNC1=CC=CC=C1 IGVMHOOQGPQIMZ-UHFFFAOYSA-N 0.000 claims 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 claims description 4
• 125000001424 substituent group Chemical group 0.000 claims 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 claims description 3
• CKIRZXDWDRUDIR-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxy-2-methylpropoxy)benzamide Chemical compound CC(C)(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F CKIRZXDWDRUDIR-UHFFFAOYSA-N 0.000 claims description 3
• JXQALZUQMVXFAC-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-[2-(methylamino)ethoxy]benzamide Chemical compound CNCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F JXQALZUQMVXFAC-UHFFFAOYSA-N 0.000 claims description 3
• YZVHIDUDGXLOLY-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(3-hydroxypropoxy)benzamide Chemical compound OCCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl YZVHIDUDGXLOLY-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• 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 claims description 3
• KCPUBYHTMMZAFC-UHFFFAOYSA-N 5-chloro-2-(2,4-difluoroanilino)-3,4-difluoro-n-(2-hydroxy-3-phenoxypropoxy)benzamide Chemical compound C=1C=CC=CC=1OCC(O)CONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(F)C=C1F KCPUBYHTMMZAFC-UHFFFAOYSA-N 0.000 claims description 3
• UVQPYTNHXUMIMH-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydroxypropoxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound OCC(O)CONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1F UVQPYTNHXUMIMH-UHFFFAOYSA-N 0.000 claims description 3
• UVQPYTNHXUMIMH-MRVPVSSYSA-N 5-chloro-n-[(2r)-2,3-dihydroxypropoxy]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound OC[C@@H](O)CONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1F UVQPYTNHXUMIMH-MRVPVSSYSA-N 0.000 claims description 3
• 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 claims 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 claims description 3
• 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 claims description 3
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
• SUDAHWBOROXANE-VIFPVBQESA-N PD 0325901-Cl Chemical compound OC[C@H](O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F SUDAHWBOROXANE-VIFPVBQESA-N 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 239000000460 chlorine Substances 0.000 claims description 3
• AEAMPCCYDKGXCC-UHFFFAOYSA-N n-(1,3-dihydroxypropan-2-yloxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound OCC(CO)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F AEAMPCCYDKGXCC-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 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 claims description 2
• GLQYKBQRDMOSAE-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-3,4-difluoro-n-(1-hydroxypropan-2-yloxy)benzamide Chemical compound OCC(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(F)C=C1F GLQYKBQRDMOSAE-UHFFFAOYSA-N 0.000 claims description 2
• BUCUZFYTODLSLK-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-3,4-difluoro-n-(2-hydroxy-3-methoxypropoxy)benzamide Chemical compound COCC(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(F)C=C1F BUCUZFYTODLSLK-UHFFFAOYSA-N 0.000 claims description 2
• BWUUVBZRYCJUGJ-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-3,4-difluoro-n-(2-hydroxy-3-phenoxypropoxy)benzamide Chemical compound C=1C=CC=CC=1OCC(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(F)C=C1F BWUUVBZRYCJUGJ-UHFFFAOYSA-N 0.000 claims description 2
• YQHATYMDYRAGRC-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-3,4-difluoro-n-(2-hydroxybutoxy)benzamide Chemical compound CCC(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(F)C=C1F YQHATYMDYRAGRC-UHFFFAOYSA-N 0.000 claims description 2
• QEIPHLNZHZGILN-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-3,4-difluoro-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(F)C=C1F QEIPHLNZHZGILN-UHFFFAOYSA-N 0.000 claims description 2
• CMEINIFNSBBEPU-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-3,4-difluoro-n-(2-hydroxypropoxy)benzamide Chemical compound CC(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(F)C=C1F CMEINIFNSBBEPU-UHFFFAOYSA-N 0.000 claims description 2
• AJBLOQYWEWENKM-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-3,4-difluoro-n-[[1-(hydroxymethyl)cyclopropyl]methoxy]benzamide Chemical compound C=1C=C(F)C(F)=C(NC=2C(=CC(F)=CC=2)F)C=1C(=O)NOCC1(CO)CC1 AJBLOQYWEWENKM-UHFFFAOYSA-N 0.000 claims description 2
• HTAQKRHMBXAWBW-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-3,4-difluoro-n-[[2-(hydroxymethyl)cyclopropyl]methoxy]benzamide Chemical compound OCC1CC1CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(F)C=C1F HTAQKRHMBXAWBW-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims 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 claims description 2
• 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 claims description 2
• 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
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
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• 229910052705 radium Inorganic materials 0.000 claims description 2
• 229910052701 rubidium Inorganic materials 0.000 claims description 2
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