ZA200105219B - 1-Heterocycle substituted diarylamines. - Google Patents
1-Heterocycle substituted diarylamines. Download PDFInfo
- Publication number
- ZA200105219B ZA200105219B ZA200105219A ZA200105219A ZA200105219B ZA 200105219 B ZA200105219 B ZA 200105219B ZA 200105219 A ZA200105219 A ZA 200105219A ZA 200105219 A ZA200105219 A ZA 200105219A ZA 200105219 B ZA200105219 B ZA 200105219B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- phenyl
- iodo
- phenylamino
- compound
- Prior art date
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- 125000005266 diarylamine group Chemical group 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 57
- -1 hydrocarbon radical Chemical class 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- 201000011510 cancer Diseases 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 230000002062 proliferating effect Effects 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 238000002512 chemotherapy Methods 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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- 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 3
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- 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 3
- 229960004528 vincristine Drugs 0.000 claims description 3
- 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 3
- 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 3
- 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 claims description 3
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- 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 description 3
- 229960002066 vinorelbine Drugs 0.000 claims description 3
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- 210000001185 bone marrow Anatomy 0.000 claims description 2
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- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
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- 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 2
- 239000000126 substance Substances 0.000 claims 53
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- FLWVAHBGRKYNEE-UHFFFAOYSA-N 2-sulfanyl-3h-oxadiazole Chemical compound SN1NC=CO1 FLWVAHBGRKYNEE-UHFFFAOYSA-N 0.000 claims 3
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- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims 1
- WFDALXPULMQOGY-UHFFFAOYSA-N 1-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-4-methyltetrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1N1C(=O)N(C)N=N1 WFDALXPULMQOGY-UHFFFAOYSA-N 0.000 claims 1
- FVTJNFQCZSPAPJ-UHFFFAOYSA-N 1-[4-fluoro-2-(4-iodo-2-methylanilino)-5-nitrophenyl]-4-methyltetrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C([N+]([O-])=O)C=C1N1C(=O)N(C)N=N1 FVTJNFQCZSPAPJ-UHFFFAOYSA-N 0.000 claims 1
- FATBYIUGJJGIOP-UHFFFAOYSA-N 1-[5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-4-methyltetrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1N1C(=O)N(C)N=N1 FATBYIUGJJGIOP-UHFFFAOYSA-N 0.000 claims 1
- UBJAZLPIPCIXCH-UHFFFAOYSA-N 1-methyl-4-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]tetrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1N1C(=O)N(C)N=N1 UBJAZLPIPCIXCH-UHFFFAOYSA-N 0.000 claims 1
- MACMNSLOLFMQKL-UHFFFAOYSA-N 1-sulfanyltriazole Chemical compound SN1C=CN=N1 MACMNSLOLFMQKL-UHFFFAOYSA-N 0.000 claims 1
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- ZICMEXBGXFWOAD-UHFFFAOYSA-N 4-[3,4-difluoro-2-(4-iodo-2-methylanilino)phenyl]-2-methyl-1h-pyrazol-5-one Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C1=CN(C)N=C1O ZICMEXBGXFWOAD-UHFFFAOYSA-N 0.000 claims 1
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- LKQJQXKFAZEKEK-UHFFFAOYSA-N 4-bromo-6-(4,4-dimethyl-5h-1,3-oxazol-2-yl)-2,3-difluoro-n-(4-iodo-2-methylphenyl)aniline Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C1=NC(C)(C)CO1 LKQJQXKFAZEKEK-UHFFFAOYSA-N 0.000 claims 1
- NFRNXQCUJHGTOD-UHFFFAOYSA-N 5-[2-(2-amino-4-iodoanilino)-3,4,5-trifluorophenyl]-1-methyltriazol-4-ol Chemical compound CN1N=NC(O)=C1C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1N NFRNXQCUJHGTOD-UHFFFAOYSA-N 0.000 claims 1
- POZBLOICDUEJOH-UHFFFAOYSA-N 5-[2-(2-amino-4-iodoanilino)-3,4-difluorophenyl]-1-methyltriazol-4-ol Chemical compound CN1N=NC(O)=C1C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1N POZBLOICDUEJOH-UHFFFAOYSA-N 0.000 claims 1
- RHGLMCDRXHZKPZ-UHFFFAOYSA-N 5-[2-(2-amino-4-iodoanilino)-4-fluorophenyl]-1-methyltriazol-4-ol Chemical compound CN1N=NC(O)=C1C1=CC=C(F)C=C1NC1=CC=C(I)C=C1N RHGLMCDRXHZKPZ-UHFFFAOYSA-N 0.000 claims 1
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- KJOHWOXRXVNBIO-UHFFFAOYSA-N 5-[3,4,5-trifluoro-2-(4-iodo-2-methylanilino)phenyl]-1,3,4-oxadiazol-2-amine Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C1=NN=C(N)O1 KJOHWOXRXVNBIO-UHFFFAOYSA-N 0.000 claims 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| US11587599P | 1999-01-13 | 1999-01-13 |
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| ZA200105219B true ZA200105219B (en) | 2002-09-25 |
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| ZA200105219A ZA200105219B (en) | 1999-01-13 | 2001-06-25 | 1-Heterocycle substituted diarylamines. |
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| JP (1) | JP2000204077A (https=) |
| UA (1) | UA72239C2 (https=) |
| ZA (1) | ZA200105219B (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010068738A1 (en) | 2008-12-10 | 2010-06-17 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| WO2011106298A1 (en) | 2010-02-25 | 2011-09-01 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| WO2013169858A1 (en) | 2012-05-08 | 2013-11-14 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| US11078540B2 (en) | 2010-03-09 | 2021-08-03 | Dana-Farber Cancer Institute, Inc. | Methods of diagnosing and treating cancer in patients having or developing resistance to a first cancer therapy |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE480527T1 (de) | 2001-12-11 | 2010-09-15 | Kyowa Hakko Kirin Co Ltd | Thiadiazolinderivate zur krebsbehandlung |
| SG2013013339A (en) | 2002-03-13 | 2014-12-30 | Array Biopharma Inc | N3 alkylated benzimidazole derivatives as mek inhibitors |
| CA2522594C (en) | 2003-04-18 | 2012-01-24 | Kyowa Hakko Kogyo Co., Ltd. | Mitotic kinesin inhibitor |
| EP1908755A4 (en) | 2005-06-24 | 2009-06-24 | Kyowa Hakko Kirin Co Ltd | THERAPEUTIC AGENT AGAINST RESTENOSIS |
| NZ601408A (en) | 2009-12-25 | 2013-12-20 | Mochida Pharm Co Ltd | Novel 3-hydroxy-5-arylisothiazole derivative |
| BR112013027883A2 (pt) | 2011-04-27 | 2017-08-08 | Mochida Pharm Co Ltd | novo derivado de 1-óxido de 3-hidroxiisotiazol |
-
1999
- 1999-03-02 JP JP11053564A patent/JP2000204077A/ja not_active Abandoned
- 1999-12-21 UA UA2001085705A patent/UA72239C2/uk unknown
-
2001
- 2001-06-25 ZA ZA200105219A patent/ZA200105219B/en unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010068738A1 (en) | 2008-12-10 | 2010-06-17 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| WO2011106298A1 (en) | 2010-02-25 | 2011-09-01 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| EP3028699A1 (en) | 2010-02-25 | 2016-06-08 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| US11078540B2 (en) | 2010-03-09 | 2021-08-03 | Dana-Farber Cancer Institute, Inc. | Methods of diagnosing and treating cancer in patients having or developing resistance to a first cancer therapy |
| US12522872B2 (en) | 2010-03-09 | 2026-01-13 | Dana-Farber Cancer Institute, Inc. | Methods of diagnosing and treating cancer in patients having or developing resistance to a first cancer therapy |
| WO2013169858A1 (en) | 2012-05-08 | 2013-11-14 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000204077A (ja) | 2000-07-25 |
| UA72239C2 (en) | 2005-02-15 |
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