CA2720818A1 - Phenoxybenzamides substitues - Google Patents

Phenoxybenzamides substitues Download PDF

Info

Publication number: CA2720818A1
Authority: CA; Canada
Prior art keywords: fluoro; iodo; phenylamino; benzamide; group
Prior art date: 2008-04-22
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA2720818A

Other languages

English (en)

Inventor

Marion Hitchcock

Ingo Hartung

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Intellectual Property GmbH

Original Assignee

Bayer Schering Pharma AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2008-04-22

Filing date

2009-04-09

Publication date

2009-10-29

2009-04-09 Application filed by Bayer Schering Pharma AG filed Critical Bayer Schering Pharma AG

2009-04-09 Priority claimed from PCT/EP2009/002675 external-priority patent/WO2009129938A1/fr

2009-10-29 Publication of CA2720818A1 publication Critical patent/CA2720818A1/fr

Status Abandoned legal-status Critical Current

Links

CJCOBMTYEDBBSY-UHFFFAOYSA-N 2-phenoxybenzamide Chemical class NC(=O)C1=CC=CC=C1OC1=CC=CC=C1 CJCOBMTYEDBBSY-UHFFFAOYSA-N 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 230
238000000034 method Methods 0.000 claims abstract description 99
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 42
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
201000010099 disease Diseases 0.000 claims abstract description 18
230000003463 hyperproliferative effect Effects 0.000 claims abstract description 11
230000033115 angiogenesis Effects 0.000 claims abstract description 7
-1 C1-C6-alkoxyalkyl Chemical group 0.000 claims description 215
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 167
125000003118 aryl group Chemical group 0.000 claims description 143
125000000753 cycloalkyl group Chemical group 0.000 claims description 134
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 130
125000001072 heteroaryl group Chemical group 0.000 claims description 120
210000004027 cell Anatomy 0.000 claims description 87
125000005843 halogen group Chemical group 0.000 claims description 78
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 66
238000002360 preparation method Methods 0.000 claims description 62
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 61
206010028980 Neoplasm Diseases 0.000 claims description 50
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 44
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
201000011510 cancer Diseases 0.000 claims description 24
239000003795 chemical substances by application Substances 0.000 claims description 23
208000035475 disorder Diseases 0.000 claims description 23
150000002148 esters Chemical class 0.000 claims description 22
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 20
239000003814 drug Substances 0.000 claims description 20
108091000080 Phosphotransferase Proteins 0.000 claims description 19
125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
102000020233 phosphotransferase Human genes 0.000 claims description 19
239000012453 solvate Substances 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 13
239000002207 metabolite Substances 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
125000004122 cyclic group Chemical group 0.000 claims description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
229940002612 prodrug Drugs 0.000 claims description 10
239000000651 prodrug Substances 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000003112 inhibitor Substances 0.000 claims description 8
230000002401 inhibitory effect Effects 0.000 claims description 8
201000001441 melanoma Diseases 0.000 claims description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
125000004434 sulfur atom Chemical group 0.000 claims description 7
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 6
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
210000000056 organ Anatomy 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
230000002159 abnormal effect Effects 0.000 claims description 5
230000010261 cell growth Effects 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims description 5
208000026310 Breast neoplasm Diseases 0.000 claims description 4
206010027476 Metastases Diseases 0.000 claims description 4
206010039491 Sarcoma Diseases 0.000 claims description 4
210000001508 eye Anatomy 0.000 claims description 4
230000001850 reproductive effect Effects 0.000 claims description 4
HCIHIEDCJGITCR-UHFFFAOYSA-N 2-[3-(dimethylcarbamoylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CN(C)C(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 HCIHIEDCJGITCR-UHFFFAOYSA-N 0.000 claims description 3
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
206010025323 Lymphomas Diseases 0.000 claims description 3
201000004681 Psoriasis Diseases 0.000 claims description 3
210000004556 brain Anatomy 0.000 claims description 3
210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
239000003102 growth factor Substances 0.000 claims description 3
208000032839 leukemia Diseases 0.000 claims description 3
230000009401 metastasis Effects 0.000 claims description 3
239000003226 mitogen Substances 0.000 claims description 3
210000002345 respiratory system Anatomy 0.000 claims description 3
208000037803 restenosis Diseases 0.000 claims description 3
210000003491 skin Anatomy 0.000 claims description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
LFWUZXYQEJVYLU-UHFFFAOYSA-N tert-butyl n-[3-[2-cyano-5-fluoro-3-(2-fluoro-4-iodoanilino)phenoxy]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C#N)=C1 LFWUZXYQEJVYLU-UHFFFAOYSA-N 0.000 claims description 3
210000001635 urinary tract Anatomy 0.000 claims description 3
AVAVHNRICSBUBJ-UHFFFAOYSA-N 2-(3,4-dihydroxy-4-methylpentoxy)-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CC(C)(O)C(O)CCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O AVAVHNRICSBUBJ-UHFFFAOYSA-N 0.000 claims description 2
WYIWPULEPGGJII-UHFFFAOYSA-N 2-(3-acetamidophenoxy)-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CC(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 WYIWPULEPGGJII-UHFFFAOYSA-N 0.000 claims description 2
FZDHOKPYJLKZIM-UHFFFAOYSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CN(C)S(=O)(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 FZDHOKPYJLKZIM-UHFFFAOYSA-N 0.000 claims description 2
IYDYIISAJXJBLH-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(2-methylpropanoylamino)phenoxy]benzamide Chemical compound CC(C)C(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 IYDYIISAJXJBLH-UHFFFAOYSA-N 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
229940123587 Cell cycle inhibitor Drugs 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
239000004037 angiogenesis inhibitor Substances 0.000 claims description 2
230000003388 anti-hormonal effect Effects 0.000 claims description 2
230000000340 anti-metabolite Effects 0.000 claims description 2
229940100197 antimetabolite Drugs 0.000 claims description 2
239000002256 antimetabolite Substances 0.000 claims description 2
239000002532 enzyme inhibitor Substances 0.000 claims description 2
210000003128 head Anatomy 0.000 claims description 2
206010020718 hyperplasia Diseases 0.000 claims description 2
239000012444 intercalating antibiotic Substances 0.000 claims description 2
210000004185 liver Anatomy 0.000 claims description 2
210000003739 neck Anatomy 0.000 claims description 2
125000006308 propyl amino group Chemical group 0.000 claims description 2
RXWSGPIWIWNUED-UHFFFAOYSA-N tert-butyl n-[3-[2-carbamoyl-5-fluoro-3-(2-fluoro-4-iodoanilino)phenoxy]phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 RXWSGPIWIWNUED-UHFFFAOYSA-N 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 3
TYJGFPQIUGKKPU-UHFFFAOYSA-N 2-(3,4-dihydroxy-3-methylbutoxy)-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound OCC(O)(C)CCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O TYJGFPQIUGKKPU-UHFFFAOYSA-N 0.000 claims 2
HFQVHXGDYFLGGT-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[(1-methylsulfonylpyrrolidin-3-yl)methoxy]benzamide Chemical compound C1N(S(=O)(=O)C)CCC1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O HFQVHXGDYFLGGT-UHFFFAOYSA-N 0.000 claims 2
206010066476 Haematological malignancy Diseases 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
JJXVSLLFPWWEFZ-UHFFFAOYSA-N 2-(1-acetylpiperidin-4-yl)oxy-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1CN(C(=O)C)CCC1OC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O JJXVSLLFPWWEFZ-UHFFFAOYSA-N 0.000 claims 1
JGNLHJYICDNIAM-UHFFFAOYSA-N 2-(3,4-dihydroxy-3-methylbutoxy)-4-fluoro-6-(2-fluoro-4-iodoanilino)benzonitrile Chemical compound OCC(O)(C)CCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C#N JGNLHJYICDNIAM-UHFFFAOYSA-N 0.000 claims 1
OTKMFLNYYJQOPF-UHFFFAOYSA-N 2-(3,4-dihydroxy-4-methylpentoxy)-3,4,5-trifluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CC(C)(O)C(O)CCOC1=C(F)C(F)=C(F)C(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O OTKMFLNYYJQOPF-UHFFFAOYSA-N 0.000 claims 1
JJFLYVDEDJXZGW-UHFFFAOYSA-N 2-(3,4-dihydroxy-4-methylpentoxy)-4-fluoro-6-(2-fluoro-4-iodoanilino)benzonitrile Chemical compound CC(C)(O)C(O)CCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C#N JJFLYVDEDJXZGW-UHFFFAOYSA-N 0.000 claims 1
WXJHXASYORDZGQ-UHFFFAOYSA-N 2-(3-carbamoylphenoxy)-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound NC(=O)C1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 WXJHXASYORDZGQ-UHFFFAOYSA-N 0.000 claims 1
SQSPYUBWJXOLHW-UHFFFAOYSA-N 2-(4-acetamidophenoxy)-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=CC(NC(=O)C)=CC=C1OC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O SQSPYUBWJXOLHW-UHFFFAOYSA-N 0.000 claims 1
BYZRLIICKLFGRZ-UHFFFAOYSA-N 2-(4-ethynyl-2-fluoroanilino)-4-fluoro-6-[3-(propylsulfamoylamino)phenoxy]benzamide Chemical compound CCCNS(=O)(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(=CC=3)C#C)F)C=C(F)C=2)C(N)=O)=C1 BYZRLIICKLFGRZ-UHFFFAOYSA-N 0.000 claims 1
PPLNALAGSCYCEK-UHFFFAOYSA-N 2-[(1,4-dimethylpiperazin-2-yl)methoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1N(C)CCN(C)C1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O PPLNALAGSCYCEK-UHFFFAOYSA-N 0.000 claims 1
XMKZFLYLNCTWIP-UHFFFAOYSA-N 2-[(1-acetylazetidin-3-yl)methoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1N(C(=O)C)CC1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O XMKZFLYLNCTWIP-UHFFFAOYSA-N 0.000 claims 1
GZAOCFWEQMGJET-UHFFFAOYSA-N 2-[(1-acetylpiperazin-2-yl)methoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CC(=O)N1CCNCC1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O GZAOCFWEQMGJET-UHFFFAOYSA-N 0.000 claims 1
CXHIVSRMAOKPJC-UHFFFAOYSA-N 2-[(1-acetylpiperidin-3-yl)methoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1N(C(=O)C)CCCC1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O CXHIVSRMAOKPJC-UHFFFAOYSA-N 0.000 claims 1
KIKJVUQFAVPDHH-UHFFFAOYSA-N 2-[(1-ethylpyrrolidin-2-yl)methoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CCN1CCCC1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O KIKJVUQFAVPDHH-UHFFFAOYSA-N 0.000 claims 1
QKPHRRIVKXMLHR-UHFFFAOYSA-N 2-[(1-ethylsulfonylpiperidin-3-yl)methoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1N(S(=O)(=O)CC)CCCC1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O QKPHRRIVKXMLHR-UHFFFAOYSA-N 0.000 claims 1
VQFWDQUHPOQCHL-GOSISDBHSA-N 2-[(3r)-3,4-dihydroxy-4-methylpentoxy]-6-(4-ethynyl-2-fluoroanilino)-4-fluorobenzamide Chemical compound CC(C)(O)[C@H](O)CCOC1=CC(F)=CC(NC=2C(=CC(=CC=2)C#C)F)=C1C(N)=O VQFWDQUHPOQCHL-GOSISDBHSA-N 0.000 claims 1
LPRVJMYZJZWDJX-UHFFFAOYSA-N 2-[2-(1-cyclopropylsulfonylpiperidin-2-yl)ethoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OCCC2N(CCCC2)S(=O)(=O)C2CC2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F LPRVJMYZJZWDJX-UHFFFAOYSA-N 0.000 claims 1
AEYNGVZRZZWANM-UHFFFAOYSA-N 2-[2-(1-ethylsulfonylpiperidin-2-yl)ethoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CCS(=O)(=O)N1CCCCC1CCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O AEYNGVZRZZWANM-UHFFFAOYSA-N 0.000 claims 1
JPSQDSVIQJFMQK-ZDUSSCGKSA-N 2-[2-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound O1C(C)(C)OC[C@@H]1CCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O JPSQDSVIQJFMQK-ZDUSSCGKSA-N 0.000 claims 1
ZRYQTOUVKMHXMB-UHFFFAOYSA-N 2-[2-[2-carbamoyl-5-fluoro-3-(2-fluoro-4-iodoanilino)phenoxy]ethyl]-n,n-dimethylpiperidine-1-carboxamide Chemical compound CN(C)C(=O)N1CCCCC1CCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O ZRYQTOUVKMHXMB-UHFFFAOYSA-N 0.000 claims 1
DKPAKUBYYNHCNI-UHFFFAOYSA-N 2-[2-amino-3-(diethylsulfamoyl)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1N DKPAKUBYYNHCNI-UHFFFAOYSA-N 0.000 claims 1
ZLPDQYQPSSEGOG-UHFFFAOYSA-N 2-[3-(2,2-dimethylpropanoylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 ZLPDQYQPSSEGOG-UHFFFAOYSA-N 0.000 claims 1
ZZKURBCBYQTMCY-UHFFFAOYSA-N 2-[3-(2,3-dihydroxypropylsulfonylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)CC(O)CO)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F ZZKURBCBYQTMCY-UHFFFAOYSA-N 0.000 claims 1
YCZKNPYDEWUODO-UHFFFAOYSA-N 2-[3-(2-chloropropan-2-ylsulfonylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CC(C)(Cl)S(=O)(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 YCZKNPYDEWUODO-UHFFFAOYSA-N 0.000 claims 1
ZNOZDILSQQMLRA-UHFFFAOYSA-N 2-[3-(3-chloropropylsulfonylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)CCCCl)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F ZNOZDILSQQMLRA-UHFFFAOYSA-N 0.000 claims 1
WQGVYFIFKORIQF-UHFFFAOYSA-N 2-[3-(acetamidomethyl)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CC(=O)NCC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 WQGVYFIFKORIQF-UHFFFAOYSA-N 0.000 claims 1
PINYROBEPUSDLB-UHFFFAOYSA-N 2-[3-(aminomethyl)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound NCC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 PINYROBEPUSDLB-UHFFFAOYSA-N 0.000 claims 1
DLHASIHSESIANQ-UHFFFAOYSA-N 2-[3-(cyclobutanecarbonylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NC(=O)C3CCC3)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F DLHASIHSESIANQ-UHFFFAOYSA-N 0.000 claims 1
NOHRPDRKGOKMHR-UHFFFAOYSA-N 2-[3-(cyclobutylsulfonylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)C3CCC3)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F NOHRPDRKGOKMHR-UHFFFAOYSA-N 0.000 claims 1
XYXKXKAWACRULD-UHFFFAOYSA-N 2-[3-(cyclohexylsulfamoyl)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OC=2C=C(C=CC=2)S(=O)(=O)NC2CCCCC2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F XYXKXKAWACRULD-UHFFFAOYSA-N 0.000 claims 1
FBBVCAGOBKMRMN-UHFFFAOYSA-N 2-[3-(cyclopentanecarbonylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NC(=O)C3CCCC3)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F FBBVCAGOBKMRMN-UHFFFAOYSA-N 0.000 claims 1
CSXCRPJPPBRCLX-UHFFFAOYSA-N 2-[3-(cyclopentylsulfonylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)C3CCCC3)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F CSXCRPJPPBRCLX-UHFFFAOYSA-N 0.000 claims 1
HGVWOBXHFZJVLK-UHFFFAOYSA-N 2-[3-(cyclopropanecarbonylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NC(=O)C3CC3)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F HGVWOBXHFZJVLK-UHFFFAOYSA-N 0.000 claims 1
NVHSWKLAAPHDQU-UHFFFAOYSA-N 2-[3-(cyclopropylsulfonylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)C3CC3)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F NVHSWKLAAPHDQU-UHFFFAOYSA-N 0.000 claims 1
VYOCUHLSOILTHM-UHFFFAOYSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-3,4,5-trifluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CN(C)S(=O)(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C(F)=C(F)C=2F)C(N)=O)=C1 VYOCUHLSOILTHM-UHFFFAOYSA-N 0.000 claims 1
RHANQDJQIUJMGI-UHFFFAOYSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethyl)benzamide Chemical compound CN(C)S(=O)(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(=O)NCCO)=C1 RHANQDJQIUJMGI-UHFFFAOYSA-N 0.000 claims 1
TYUCBRSONKRTHU-UHFFFAOYSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)-n-(2-hydroxypropyl)benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)N(C)C)C=CC=2)C(C(=O)NCC(O)C)=C1NC1=CC=C(I)C=C1F TYUCBRSONKRTHU-UHFFFAOYSA-N 0.000 claims 1
RHYCDNBTNRUSJU-CQSZACIVSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)-n-[(2r)-1-hydroxypropan-2-yl]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)N(C)C)C=CC=2)C(C(=O)N[C@@H](CO)C)=C1NC1=CC=C(I)C=C1F RHYCDNBTNRUSJU-CQSZACIVSA-N 0.000 claims 1
TYUCBRSONKRTHU-CQSZACIVSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)-n-[(2r)-2-hydroxypropyl]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)N(C)C)C=CC=2)C(C(=O)NC[C@H](O)C)=C1NC1=CC=C(I)C=C1F TYUCBRSONKRTHU-CQSZACIVSA-N 0.000 claims 1
RHYCDNBTNRUSJU-AWEZNQCLSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)-n-[(2s)-1-hydroxypropan-2-yl]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)N(C)C)C=CC=2)C(C(=O)N[C@H](CO)C)=C1NC1=CC=C(I)C=C1F RHYCDNBTNRUSJU-AWEZNQCLSA-N 0.000 claims 1
TYUCBRSONKRTHU-AWEZNQCLSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)-n-[(2s)-2-hydroxypropyl]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)N(C)C)C=CC=2)C(C(=O)NC[C@@H](O)C)=C1NC1=CC=C(I)C=C1F TYUCBRSONKRTHU-AWEZNQCLSA-N 0.000 claims 1
NZNUWRVMBAUDEB-UHFFFAOYSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)-n-methylbenzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)N(C)C)C=CC=2)C(C(=O)NC)=C1NC1=CC=C(I)C=C1F NZNUWRVMBAUDEB-UHFFFAOYSA-N 0.000 claims 1
XXYWDDIQDYFYTC-UHFFFAOYSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-4-fluoro-6-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)S(=O)(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)C)C=C(F)C=2)C(N)=O)=C1 XXYWDDIQDYFYTC-UHFFFAOYSA-N 0.000 claims 1
UQRUONQSIXIRET-UHFFFAOYSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-4-fluoro-6-(4-iodoanilino)benzamide Chemical compound CN(C)S(=O)(=O)NC1=CC=CC(OC=2C(=C(NC=3C=CC(I)=CC=3)C=C(F)C=2)C(N)=O)=C1 UQRUONQSIXIRET-UHFFFAOYSA-N 0.000 claims 1
MYACYWVPMQTEJY-UHFFFAOYSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-6-(4-ethynyl-2-fluoroanilino)-3,4,5-trifluorobenzamide Chemical compound CN(C)S(=O)(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(=CC=3)C#C)F)C(F)=C(F)C=2F)C(N)=O)=C1 MYACYWVPMQTEJY-UHFFFAOYSA-N 0.000 claims 1
MKUVNALVNOXNOP-UHFFFAOYSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-6-(4-ethynyl-2-fluoroanilino)-4-fluorobenzamide Chemical compound CN(C)S(=O)(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(=CC=3)C#C)F)C=C(F)C=2)C(N)=O)=C1 MKUVNALVNOXNOP-UHFFFAOYSA-N 0.000 claims 1
ATDNVSARIVPFDT-UHFFFAOYSA-N 2-[3-(dimethylsulfamoylamino)phenoxy]-n-ethyl-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)N(C)C)C=CC=2)C(C(=O)NCC)=C1NC1=CC=C(I)C=C1F ATDNVSARIVPFDT-UHFFFAOYSA-N 0.000 claims 1
HAKOJLPLSRPXQQ-UHFFFAOYSA-N 2-[4-(dimethylsulfamoylamino)cyclohexyl]oxy-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1CC(NS(=O)(=O)N(C)C)CCC1OC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O HAKOJLPLSRPXQQ-UHFFFAOYSA-N 0.000 claims 1
DTRORBBFGPTBOP-CQSZACIVSA-N 2-[[(2r)-1-acetylpyrrolidin-2-yl]methoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CC(=O)N1CCC[C@@H]1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O DTRORBBFGPTBOP-CQSZACIVSA-N 0.000 claims 1
JNQMJJOKUWHNMB-CQSZACIVSA-N 2-[[(2r)-1-ethylsulfonylpyrrolidin-2-yl]methoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CCS(=O)(=O)N1CCC[C@@H]1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O JNQMJJOKUWHNMB-CQSZACIVSA-N 0.000 claims 1
JNQMJJOKUWHNMB-AWEZNQCLSA-N 2-[[(2s)-1-ethylsulfonylpyrrolidin-2-yl]methoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound CCS(=O)(=O)N1CCC[C@H]1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O JNQMJJOKUWHNMB-AWEZNQCLSA-N 0.000 claims 1
ZJVBUPOUGFCNMA-UHFFFAOYSA-N 2-[[1-(benzenesulfonyl)piperidin-3-yl]methoxy]-4-fluoro-6-(2-fluoro-4-iodoanilino)benzamide Chemical compound C1=C(F)C=C(OCC2CN(CCC2)S(=O)(=O)C=2C=CC=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F ZJVBUPOUGFCNMA-UHFFFAOYSA-N 0.000 claims 1
JATTVYJZXYCVHQ-UHFFFAOYSA-N 2-cyclopent-3-en-1-yloxy-4-fluoro-6-(2-fluoro-4-iodoanilino)benzonitrile Chemical compound N#CC=1C(OC2CC=CC2)=CC(F)=CC=1NC1=CC=C(I)C=C1F JATTVYJZXYCVHQ-UHFFFAOYSA-N 0.000 claims 1
NPMWXHKORZAOAR-UHFFFAOYSA-N 3-[2-carbamoyl-5-fluoro-3-(2-fluoro-4-iodoanilino)phenoxy]benzoic acid Chemical compound C1=C(F)C=C(OC=2C=C(C=CC=2)C(O)=O)C(C(=O)N)=C1NC1=CC=C(I)C=C1F NPMWXHKORZAOAR-UHFFFAOYSA-N 0.000 claims 1
RMTIFICPEANZHX-UHFFFAOYSA-N 3-[3-[2-cyano-5-fluoro-3-(2-fluoro-4-iodoanilino)phenoxy]phenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C#N)=C1 RMTIFICPEANZHX-UHFFFAOYSA-N 0.000 claims 1
VXTLALWYFGKOQJ-UHFFFAOYSA-N 3-[[2-carbamoyl-5-fluoro-3-(2-fluoro-4-iodoanilino)phenoxy]methyl]pyrrolidine-1-sulfonic acid Chemical compound C1=C(F)C=C(OCC2CN(CC2)S(O)(=O)=O)C(C(=O)N)=C1NC1=CC=C(I)C=C1F VXTLALWYFGKOQJ-UHFFFAOYSA-N 0.000 claims 1
NVBROIHDAOTDGJ-UHFFFAOYSA-N 4-[2-[2-carbamoyl-5-fluoro-3-(2-fluoro-4-iodoanilino)phenoxy]ethyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O NVBROIHDAOTDGJ-UHFFFAOYSA-N 0.000 claims 1
QVAWIFCRQLKCOS-UHFFFAOYSA-N 4-[2-carbamoyl-5-fluoro-3-(2-fluoro-4-iodoanilino)phenoxy]-n,n-dimethylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCC1OC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O QVAWIFCRQLKCOS-UHFFFAOYSA-N 0.000 claims 1
WXDLHEVCELBIPM-UHFFFAOYSA-N 4-[2-carbamoyl-5-fluoro-3-(2-fluoro-4-iodoanilino)phenoxy]phthalic acid Chemical compound C1=C(F)C=C(OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)C(C(=O)N)=C1NC1=CC=C(I)C=C1F WXDLHEVCELBIPM-UHFFFAOYSA-N 0.000 claims 1
WWZDLOBTLSRJQZ-UHFFFAOYSA-N 4-[2-cyano-5-fluoro-3-(2-fluoro-4-iodoanilino)phenoxy]piperidine-1-carboxylic acid Chemical compound C(#N)C1=C(OC2CCN(CC2)C(=O)O)C=C(C=C1NC1=C(C=C(C=C1)I)F)F WWZDLOBTLSRJQZ-UHFFFAOYSA-N 0.000 claims 1
JBJWDYWVXBDXTK-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-(1-methylpiperidin-4-yl)oxybenzamide Chemical compound C1CN(C)CCC1OC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O JBJWDYWVXBDXTK-UHFFFAOYSA-N 0.000 claims 1
FTHJWGKSBCJFBP-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-(1-methylpyrazol-4-yl)oxybenzamide Chemical compound C1=NN(C)C=C1OC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O FTHJWGKSBCJFBP-UHFFFAOYSA-N 0.000 claims 1
FSEXERLSWAESRU-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-(1-methylsulfonylpiperidin-4-yl)oxybenzamide Chemical compound C1CN(S(=O)(=O)C)CCC1OC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O FSEXERLSWAESRU-UHFFFAOYSA-N 0.000 claims 1
NZQQDZZBAKWQOT-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-(3-methylbut-3-enoxy)benzonitrile Chemical compound CC(=C)CCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C#N NZQQDZZBAKWQOT-UHFFFAOYSA-N 0.000 claims 1
RRHBRRREQRRXIX-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-(3-methylsulfonylphenoxy)benzamide Chemical compound CS(=O)(=O)C1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 RRHBRRREQRRXIX-UHFFFAOYSA-N 0.000 claims 1
WTUDOCKADJZZAP-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-(4-methylpent-3-enoxy)benzonitrile Chemical compound CC(C)=CCCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C#N WTUDOCKADJZZAP-UHFFFAOYSA-N 0.000 claims 1
WDIUPPJXBYPJBI-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[(1-methylpiperazin-2-yl)methoxy]benzamide Chemical compound CN1CCNCC1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O WDIUPPJXBYPJBI-UHFFFAOYSA-N 0.000 claims 1
RWTYYTJLADAHPE-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[(1-methylsulfonylazetidin-3-yl)methoxy]benzamide Chemical compound C1N(S(=O)(=O)C)CC1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O RWTYYTJLADAHPE-UHFFFAOYSA-N 0.000 claims 1
SOSKPJGFVKCAJE-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[(1-methylsulfonylpiperidin-3-yl)methoxy]benzamide Chemical compound C1N(S(=O)(=O)C)CCCC1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O SOSKPJGFVKCAJE-UHFFFAOYSA-N 0.000 claims 1
UODXNUGEDPGTFW-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[(1-morpholin-4-ylsulfonylpyrrolidin-3-yl)methoxy]benzamide Chemical compound C1=C(F)C=C(OCC2CN(CC2)S(=O)(=O)N2CCOCC2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F UODXNUGEDPGTFW-UHFFFAOYSA-N 0.000 claims 1
HWRNGKFLRCPRPM-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[(4-methylsulfonylmorpholin-2-yl)methoxy]benzamide Chemical compound C1N(S(=O)(=O)C)CCOC1COC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O HWRNGKFLRCPRPM-UHFFFAOYSA-N 0.000 claims 1
USNBGBGXKSWRJQ-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[(4-morpholin-4-ylsulfonylmorpholin-2-yl)methoxy]benzamide Chemical compound C1=C(F)C=C(OCC2OCCN(C2)S(=O)(=O)N2CCOCC2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F USNBGBGXKSWRJQ-UHFFFAOYSA-N 0.000 claims 1
GASCDBFLCUGWLP-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[2-(1-methylsulfonylpiperidin-2-yl)ethoxy]benzamide Chemical compound CS(=O)(=O)N1CCCCC1CCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O GASCDBFLCUGWLP-UHFFFAOYSA-N 0.000 claims 1
LPYBUESJJBREJX-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[2-(4-methylsulfonylpiperazin-1-yl)ethoxy]benzamide Chemical compound C1CN(S(=O)(=O)C)CCN1CCOC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O LPYBUESJJBREJX-UHFFFAOYSA-N 0.000 claims 1
HLYNFQLBOGIRTM-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(1,1,2,2,2-pentafluoroethyl)phenoxy]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(C=CC=2)C(F)(F)C(F)(F)F)C(C(=O)N)=C1NC1=CC=C(I)C=C1F HLYNFQLBOGIRTM-UHFFFAOYSA-N 0.000 claims 1
ORSHEXIUHBFYQW-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(1h-1,2,4-triazol-5-ylsulfonylamino)phenoxy]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)C=3NC=NN=3)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F ORSHEXIUHBFYQW-UHFFFAOYSA-N 0.000 claims 1
AKWCEZPQSLBCML-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(1h-imidazol-5-ylsulfonylamino)phenoxy]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)C=3N=CNC=3)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F AKWCEZPQSLBCML-UHFFFAOYSA-N 0.000 claims 1
MIDJTVQRDNFBDZ-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(2,2,2-trifluoroethylsulfamoylamino)phenoxy]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)NCC(F)(F)F)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F MIDJTVQRDNFBDZ-UHFFFAOYSA-N 0.000 claims 1
CAEWZQSPABNBNU-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(2-methoxyethylsulfonylamino)phenoxy]benzamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 CAEWZQSPABNBNU-UHFFFAOYSA-N 0.000 claims 1
GHMVPMRNZMWOQN-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(methanesulfonamidomethyl)phenoxy]benzamide Chemical compound CS(=O)(=O)NCC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 GHMVPMRNZMWOQN-UHFFFAOYSA-N 0.000 claims 1
LTTBMISCDOGBFZ-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(methylsulfonylmethyl)phenoxy]benzamide Chemical compound CS(=O)(=O)CC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 LTTBMISCDOGBFZ-UHFFFAOYSA-N 0.000 claims 1
XNJCLJPFRWMUAG-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(morpholin-4-ylsulfonylamino)phenoxy]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)N3CCOCC3)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F XNJCLJPFRWMUAG-UHFFFAOYSA-N 0.000 claims 1
SHOKFLCYBWAJOL-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(pyrrolidin-1-ylsulfonylamino)phenoxy]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)N3CCCC3)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F SHOKFLCYBWAJOL-UHFFFAOYSA-N 0.000 claims 1
IWMDPOIAMPDYQT-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(sulfamoylamino)phenoxy]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(N)(=O)=O)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F IWMDPOIAMPDYQT-UHFFFAOYSA-N 0.000 claims 1
SAWIAPXBORSMPV-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-(sulfamoylmethyl)phenoxy]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(CS(N)(=O)=O)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F SAWIAPXBORSMPV-UHFFFAOYSA-N 0.000 claims 1
AKPMSUOWDRSZQF-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-[(1-hydroxycyclopropanecarbonyl)amino]phenoxy]benzamide Chemical compound C1=C(F)C=C(OC=2C=C(NC(=O)C3(O)CC3)C=CC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F AKPMSUOWDRSZQF-UHFFFAOYSA-N 0.000 claims 1
JOKMVLUYDDEODT-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[3-[(1-methylpyrazol-4-yl)sulfonylamino]phenoxy]benzamide Chemical compound C1=NN(C)C=C1S(=O)(=O)NC1=CC=CC(OC=2C(=C(NC=3C(=CC(I)=CC=3)F)C=C(F)C=2)C(N)=O)=C1 JOKMVLUYDDEODT-UHFFFAOYSA-N 0.000 claims 1
MOAWKVITHZALAO-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[4-[methyl(methylsulfonyl)amino]phenoxy]benzamide Chemical compound C1=CC(N(C)S(C)(=O)=O)=CC=C1OC1=CC(F)=CC(NC=2C(=CC(I)=CC=2)F)=C1C(N)=O MOAWKVITHZALAO-UHFFFAOYSA-N 0.000 claims 1
DHMWFSSFQPHFMV-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-6-[5-(1h-imidazol-5-ylsulfonylamino)pyridin-3-yl]oxybenzamide Chemical compound C1=C(F)C=C(OC=2C=C(NS(=O)(=O)C=3N=CNC=3)C=NC=2)C(C(=O)N)=C1NC1=CC=C(I)C=C1F DHMWFSSFQPHFMV-UHFFFAOYSA-N 0.000 claims 1
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XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 1

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CA2720818A 2008-04-22 2009-04-09 Phenoxybenzamides substitues Abandoned CA2720818A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP08075314.8		2008-04-22
EP08168725.3		2008-11-10
PCT/EP2009/002675 WO2009129938A1 (fr)	2008-04-22	2009-04-09	Phénoxybenzamides substitués

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CA2720818A1 true CA2720818A1 (fr)	2009-10-29

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CA2720818A Abandoned CA2720818A1 (fr)	2008-04-22	2009-04-09	Phenoxybenzamides substitues

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN114929669A (zh) *	2020-01-22	2022-08-19	中外制药株式会社	具有抗肿瘤活性的芳基酰胺衍生物

2009
- 2009-04-09 CA CA2720818A patent/CA2720818A1/fr not_active Abandoned

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN114929669A (zh) *	2020-01-22	2022-08-19	中外制药株式会社	具有抗肿瘤活性的芳基酰胺衍生物

Publication	Publication Date	Title
US20110071125A1 (en)	2011-03-24	Substituted phenylamino-benzene derivatives useful for treating hyper-proliferative disorders and diseases associated with mitogen extracellular kinase activity
US20110039819A1 (en)	2011-02-17	Substituted phenoxybenzamides
EP2346818B1 (fr)	2012-12-05	Sulfonamido phénoxybenzamides substitués
JP5732662B2 (ja)	2015-06-10	置換アミドフェノキシベンズアミド
US9045429B2 (en)	2015-06-02	Substituted phenoxypyridines
CN102574782B (zh)	2014-10-08	取代的卤代苯氧基苯甲酰胺衍生物
US8962606B2 (en)	2015-02-24	Substituted benzosulphonamides
CA2720818A1 (fr)	2009-10-29	Phenoxybenzamides substitues
CA2777430A1 (fr)	2011-04-28	Benzosulfonamides substitues
HK1174325A (en)	2013-06-07	Substituted benzosulphonamides

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Date	Code	Title	Description
2014-03-26	EEER	Examination request	Effective date: 20140319
2016-10-20	FZDE	Dead	Effective date: 20160908

CA2720818A1 - Phenoxybenzamides substitues - Google Patents

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