ZA200104000B

ZA200104000B - Antiviral method using MEK inhibitors.

Antiviral method using MEK inhibitors. Download PDF

Info

Publication number: ZA200104000B
Authority: ZA; South Africa
Prior art keywords: methyl; phenylamino; iodo; benzamide; difluoro
Prior art date: 1999-01-07

Application number

ZA200104000A

Other languages

English (en)

Inventor

Alexander James Bridges

Stephen Joseph Gracheck

Alan Robert Saltiel

David Thomas Dudley

Annette Lynn Meyer

Judith Sebolt-Leopold

Original Assignee

Warner Lambert Co

Priority date

1999-01-07

Filing date

2001-05-16

Publication date

2002-08-16

2001-05-16 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2002-08-16 Publication of ZA200104000B publication Critical patent/ZA200104000B/en

Links

238000000034 method Methods 0.000 title claims description 63
239000002829 mitogen activated protein kinase inhibitor Substances 0.000 title claims description 38
230000000840 anti-viral effect Effects 0.000 title claims description 11
-1 phenyl amine compound Chemical class 0.000 claims description 114
150000001875 compounds Chemical class 0.000 claims description 83
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 63
125000000217 alkyl group Chemical group 0.000 claims description 48
239000000203 mixture Substances 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 39
229940124647 MEK inhibitor Drugs 0.000 claims description 29
241000124008 Mammalia Species 0.000 claims description 28
208000036142 Viral infection Diseases 0.000 claims description 27
239000000126 substance Substances 0.000 claims description 27
230000009385 viral infection Effects 0.000 claims description 27
150000002431 hydrogen Chemical group 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 21
125000000753 cycloalkyl group Chemical group 0.000 claims description 21
125000001072 heteroaryl group Chemical group 0.000 claims description 20
229910052760 oxygen Inorganic materials 0.000 claims description 20
239000005711 Benzoic acid Substances 0.000 claims description 19
125000005843 halogen group Chemical group 0.000 claims description 18
125000005842 heteroatom Chemical group 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 16
125000001153 fluoro group Chemical group F* 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 15
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000003282 alkyl amino group Chemical group 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 12
150000001408 amides Chemical class 0.000 claims description 12
125000004122 cyclic group Chemical group 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
125000000623 heterocyclic group Chemical group 0.000 claims description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
229940002612 prodrug Drugs 0.000 claims description 8
239000000651 prodrug Substances 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
230000003612 virological effect Effects 0.000 claims description 7
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 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000003831 tetrazolyl group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
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 claims description 5
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
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 claims description 4
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 claims description 4
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 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
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 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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
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 claims description 3
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 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
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
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 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 claims description 3
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 claims description 3
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 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
125000001246 bromo group Chemical group Br* 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
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
BQQMUASDAHOKDU-UHFFFAOYSA-N 2-(2-ethyl-4-iodoanilino)-n-(2-hydroxyethyl)-5-nitrobenzamide Chemical compound CCC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCCO BQQMUASDAHOKDU-UHFFFAOYSA-N 0.000 claims description 2
XYIWZWHCZQKVEH-UHFFFAOYSA-N 2-(2-morpholin-4-ylethyl)benzamide Chemical compound NC(=O)C1=CC=CC=C1CCN1CCOCC1 XYIWZWHCZQKVEH-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 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 claims 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 claims 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 claims description 2
OLAJIJDQDNHPHA-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-nitro-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCCCN1CCCCC1 OLAJIJDQDNHPHA-UHFFFAOYSA-N 0.000 claims description 2
BJULGELJDWFRAX-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-nitro-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(=O)NOCC1=CC=CC=C1 BJULGELJDWFRAX-UHFFFAOYSA-N 0.000 claims 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 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
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 claims 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 claims 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 claims 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 claims 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 claims 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 claims description 2
BGKLFAQCHHCZRZ-UHFFFAOYSA-N 4-iodo-2-methylaniline Chemical compound CC1=CC(I)=CC=C1N BGKLFAQCHHCZRZ-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims description 2
HCJZFECDFDVVFQ-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(3-methylpent-2-en-4-ynoxy)benzamide Chemical compound C#CC(C)=CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C HCJZFECDFDVVFQ-UHFFFAOYSA-N 0.000 claims description 2
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 claims 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 claims 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 claims 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 claims description 2
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 claims description 2
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 claims 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 claims 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 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
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 claims description 2
LESLNRINHALPLQ-UHFFFAOYSA-N 5-chloro-3,4-difluoro-2-(4-iodoanilino)benzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1 LESLNRINHALPLQ-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
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 claims 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 claims description 2
GUGZLIXQNJDNQN-UHFFFAOYSA-N 5-chloro-n-[3-(diethylamino)propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)CCCNC(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C GUGZLIXQNJDNQN-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
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 claims 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 claims description 2
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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 claims description 2
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150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
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208000002672 hepatitis B Diseases 0.000 claims 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 2
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 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 claims 2
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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 claims 1
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 claims 1
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 claims 1
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 claims 1
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 claims 1
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 1
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 1
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JIIYFBKNQCBEGE-UHFFFAOYSA-N 2-(pyridin-3-ylmethoxy)benzamide Chemical compound NC(=O)C1=CC=CC=C1OCC1=CC=CN=C1 JIIYFBKNQCBEGE-UHFFFAOYSA-N 0.000 claims 1
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 claims 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 claims 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 claims 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 claims 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 claims 1
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 claims 1
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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 claims 1
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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 claims 1
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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 claims 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 claims 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 claims 1
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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 claims 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 claims 1
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 claims 1
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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 claims 1
PFWAYQMMRCDJJX-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-prop-2-enoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCC=C PFWAYQMMRCDJJX-UHFFFAOYSA-N 0.000 claims 1
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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 claims 1
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 claims 1
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 claims 1
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 claims 1
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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 claims 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 claims 1
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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 claims 1
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 claims 1
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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 claims 1
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 claims 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 claims 1
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 claims 1
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UICIKQQORQRHGH-UHFFFAOYSA-N 5-bromo-N-[2-[di(propan-2-yl)amino]ethyl]-2-(4-iodo-2-methylanilino)benzamide [5-fluoro-2-(4-iodo-2-methylanilino)phenyl]-(3-hydroxypyrrolidin-1-yl)methanone Chemical compound Cc1cc(I)ccc1Nc1ccc(F)cc1C(=O)N1CCC(O)C1.CC(C)N(CCNC(=O)c1cc(Br)ccc1Nc1ccc(I)cc1C)C(C)C UICIKQQORQRHGH-UHFFFAOYSA-N 0.000 claims 1
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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 claims 1
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 claims 1
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