JP2015503597A5 - - Google Patents
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- JP2015503597A5 JP2015503597A5 JP2014551508A JP2014551508A JP2015503597A5 JP 2015503597 A5 JP2015503597 A5 JP 2015503597A5 JP 2014551508 A JP2014551508 A JP 2014551508A JP 2014551508 A JP2014551508 A JP 2014551508A JP 2015503597 A5 JP2015503597 A5 JP 2015503597A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- fluoro
- substituted
- compound
- amino
- Prior art date
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 229
- 150000003839 salts Chemical class 0.000 claims description 214
- 125000000217 alkyl group Chemical group 0.000 claims description 161
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 84
- 125000005843 halogen group Chemical group 0.000 claims description 79
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 125000004414 alkyl thio group Chemical group 0.000 claims description 42
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 42
- -1 amino, carboxy Chemical group 0.000 claims description 41
- 150000002431 hydrogen Chemical group 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims description 22
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 19
- 125000004423 acyloxy group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 125000002346 iodo group Chemical group I* 0.000 claims description 14
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical group [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 13
- 125000001246 bromo group Chemical group Br* 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000000651 prodrug Substances 0.000 claims description 12
- 229940002612 prodrug Drugs 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- NCXQEKULAYAEMA-UHFFFAOYSA-N 4-fluoro-5-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-1,2,3-benzothiadiazole-6-carboxamide Chemical compound OCCONC(=O)C1=CC=2SN=NC=2C(F)=C1NC1=CC=C(I)C=C1F NCXQEKULAYAEMA-UHFFFAOYSA-N 0.000 claims description 4
- UFZJUVFSSINETF-UHFFFAOYSA-N 4-fluoro-5-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-1,3-benzothiazole-6-carboxamide Chemical compound OCCONC(=O)C1=CC=2SC=NC=2C(F)=C1NC1=CC=C(I)C=C1F UFZJUVFSSINETF-UHFFFAOYSA-N 0.000 claims description 4
- KALDBJONLIOQJS-UHFFFAOYSA-N 4-fluoro-5-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-1,3-benzoxazole-6-carboxamide Chemical compound OCCONC(=O)C1=CC=2OC=NC=2C(F)=C1NC1=CC=C(I)C=C1F KALDBJONLIOQJS-UHFFFAOYSA-N 0.000 claims description 4
- GGMRJHYZPWGUMQ-UHFFFAOYSA-N 5-(4-bromo-2-chloroanilino)-4-fluoro-n-(2-hydroxyethoxy)-1,3-benzoxazole-6-carboxamide Chemical compound OCCONC(=O)C1=CC=2OC=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl GGMRJHYZPWGUMQ-UHFFFAOYSA-N 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 230000033115 angiogenesis Effects 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- IVGFMRMTHAGJIO-UHFFFAOYSA-N 1-(2,3-dihydroxypropyl)-n-[4-fluoro-5-(2-fluoro-4-iodoanilino)-1,2,3-benzothiadiazol-6-yl]cyclopropane-1-sulfonamide Chemical compound C=1C=2SN=NC=2C(F)=C(NC=2C(=CC(I)=CC=2)F)C=1NS(=O)(=O)C1(CC(O)CO)CC1 IVGFMRMTHAGJIO-UHFFFAOYSA-N 0.000 claims description 3
- YLABLNGZCLLPKS-UHFFFAOYSA-N 1-(2,3-dihydroxypropyl)-n-[4-fluoro-5-(2-fluoro-4-iodoanilino)-1,3-benzothiazol-6-yl]cyclopropane-1-sulfonamide Chemical compound C=1C=2SC=NC=2C(F)=C(NC=2C(=CC(I)=CC=2)F)C=1NS(=O)(=O)C1(CC(O)CO)CC1 YLABLNGZCLLPKS-UHFFFAOYSA-N 0.000 claims description 3
- GNCVQXJQAMRTTQ-UHFFFAOYSA-N 5-(4-bromo-2-chloroanilino)-n-(2,3-dihydroxypropoxy)-4-fluoro-1,2,3-benzothiadiazole-6-carboxamide Chemical compound OCC(O)CONC(=O)C1=CC=2SN=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl GNCVQXJQAMRTTQ-UHFFFAOYSA-N 0.000 claims description 3
- RDSLUYCJFHGBFK-UHFFFAOYSA-N 5-(4-bromo-2-chloroanilino)-n-(2,3-dihydroxypropoxy)-4-fluoro-1,3-benzothiazole-6-carboxamide Chemical compound OCC(O)CONC(=O)C1=CC=2SC=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl RDSLUYCJFHGBFK-UHFFFAOYSA-N 0.000 claims description 3
- ZUNDYGYIUYOIAJ-UHFFFAOYSA-N 5-(4-bromo-2-chloroanilino)-n-(2,3-dihydroxypropoxy)-4-fluoro-1,3-benzoxazole-6-carboxamide Chemical compound OCC(O)CONC(=O)C1=CC=2OC=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl ZUNDYGYIUYOIAJ-UHFFFAOYSA-N 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- YVKXPLMHOZUAJJ-UHFFFAOYSA-N n-(2,3-dihydroxypropoxy)-4-fluoro-5-(2-fluoro-4-iodoanilino)-1,2,3-benzothiadiazole-6-carboxamide Chemical compound OCC(O)CONC(=O)C1=CC=2SN=NC=2C(F)=C1NC1=CC=C(I)C=C1F YVKXPLMHOZUAJJ-UHFFFAOYSA-N 0.000 claims description 3
- ZPIQKRUUBSNJIV-UHFFFAOYSA-N n-(2,3-dihydroxypropoxy)-4-fluoro-5-(2-fluoro-4-iodoanilino)-1,3-benzothiazole-6-carboxamide Chemical compound OCC(O)CONC(=O)C1=CC=2SC=NC=2C(F)=C1NC1=CC=C(I)C=C1F ZPIQKRUUBSNJIV-UHFFFAOYSA-N 0.000 claims description 3
- XHPSQAJXPCJPIP-UHFFFAOYSA-N n-(2,3-dihydroxypropoxy)-4-fluoro-5-(2-fluoro-4-iodoanilino)-1,3-benzoxazole-6-carboxamide Chemical compound OCC(O)CONC(=O)C1=CC=2OC=NC=2C(F)=C1NC1=CC=C(I)C=C1F XHPSQAJXPCJPIP-UHFFFAOYSA-N 0.000 claims description 3
- MZYPAEXPISOZOC-UHFFFAOYSA-N n-[4-fluoro-5-(2-fluoro-4-iodoanilino)-1,2,3-benzothiadiazol-6-yl]cyclopropanesulfonamide Chemical compound FC1=CC(I)=CC=C1NC(C(=C1N=NSC1=C1)F)=C1NS(=O)(=O)C1CC1 MZYPAEXPISOZOC-UHFFFAOYSA-N 0.000 claims description 3
- CWBQVQKLFOWIQT-UHFFFAOYSA-N n-[4-fluoro-5-(2-fluoro-4-iodoanilino)-1,3-benzothiazol-6-yl]cyclopropanesulfonamide Chemical compound FC1=CC(I)=CC=C1NC(C(=C1)NS(=O)(=O)C2CC2)=C(F)C2=C1SC=N2 CWBQVQKLFOWIQT-UHFFFAOYSA-N 0.000 claims description 3
- AQUXUXBXROMQDQ-UHFFFAOYSA-N n-[4-fluoro-5-(2-fluoro-4-iodoanilino)-1,3-benzoxazol-6-yl]cyclopropanesulfonamide Chemical compound FC1=CC(I)=CC=C1NC(C(=C1)NS(=O)(=O)C2CC2)=C(F)C2=C1OC=N2 AQUXUXBXROMQDQ-UHFFFAOYSA-N 0.000 claims description 3
- QIUSAXDTVFDSSC-UHFFFAOYSA-N n-[5-(4-bromo-2-chloroanilino)-4-fluoro-1,2,3-benzothiadiazol-6-yl]-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide Chemical compound C=1C=2SN=NC=2C(F)=C(NC=2C(=CC(Br)=CC=2)Cl)C=1NS(=O)(=O)C1(CC(O)CO)CC1 QIUSAXDTVFDSSC-UHFFFAOYSA-N 0.000 claims description 3
- LFUHXJFYAXLVKX-UHFFFAOYSA-N n-[5-(4-bromo-2-chloroanilino)-4-fluoro-1,2,3-benzothiadiazol-6-yl]cyclopropanesulfonamide Chemical compound C1CC1S(=O)(=O)NC1=CC=2SN=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl LFUHXJFYAXLVKX-UHFFFAOYSA-N 0.000 claims description 3
- AITYBOUARXLEQK-UHFFFAOYSA-N n-[5-(4-bromo-2-chloroanilino)-4-fluoro-1,3-benzothiazol-6-yl]-1-(2,3-dihydroxypropyl)cyclopropane-1-sulfonamide Chemical compound C=1C=2SC=NC=2C(F)=C(NC=2C(=CC(Br)=CC=2)Cl)C=1NS(=O)(=O)C1(CC(O)CO)CC1 AITYBOUARXLEQK-UHFFFAOYSA-N 0.000 claims description 3
- RFWUBRVJSLVOKP-UHFFFAOYSA-N n-[5-(4-bromo-2-chloroanilino)-4-fluoro-1,3-benzothiazol-6-yl]cyclopropanesulfonamide Chemical compound C1CC1S(=O)(=O)NC1=CC=2SC=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl RFWUBRVJSLVOKP-UHFFFAOYSA-N 0.000 claims description 3
- NDQJPHQEBUKDIR-UHFFFAOYSA-N n-[5-(4-bromo-2-chloroanilino)-4-fluoro-1,3-benzoxazol-6-yl]cyclopropanesulfonamide Chemical compound C1CC1S(=O)(=O)NC1=CC=2OC=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl NDQJPHQEBUKDIR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- HOCULWJPJJSOON-UHFFFAOYSA-N 5-(4-bromo-2-chloroanilino)-n-(cyclopropylmethyl)-4-fluoro-1,2,3-benzothiadiazole-6-carboxamide Chemical compound C1CC1CNC(=O)C1=CC=2SN=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl HOCULWJPJJSOON-UHFFFAOYSA-N 0.000 claims description 2
- UJFHHNJUMIXDJJ-UHFFFAOYSA-N 5-(4-bromo-2-chloroanilino)-n-(cyclopropylmethyl)-4-fluoro-1,3-benzothiazole-6-carboxamide Chemical compound C1CC1CNC(=O)C1=CC=2SC=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl UJFHHNJUMIXDJJ-UHFFFAOYSA-N 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 208000000094 Chronic Pain Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 2
- 208000037976 chronic inflammation Diseases 0.000 claims description 2
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000030533 eye disease Diseases 0.000 claims description 2
- 150000002443 hydroxylamines Chemical class 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims description 2
- SJHCMRCSWRLRJV-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-fluoro-5-(2-fluoro-4-iodoanilino)-1,2,3-benzothiadiazole-6-carboxamide Chemical compound FC1=CC(I)=CC=C1NC(C(=C1)C(=O)NCC2CC2)=C(F)C2=C1SN=N2 SJHCMRCSWRLRJV-UHFFFAOYSA-N 0.000 claims description 2
- IBRCSDXVMRNLTO-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-fluoro-5-(2-fluoro-4-iodoanilino)-1,3-benzothiazole-6-carboxamide Chemical compound FC1=CC(I)=CC=C1NC(C(=C1)C(=O)NCC2CC2)=C(F)C2=C1SC=N2 IBRCSDXVMRNLTO-UHFFFAOYSA-N 0.000 claims description 2
- VXSSMUDYMVEHPO-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-fluoro-5-(2-fluoro-4-iodoanilino)-1,3-benzoxazole-6-carboxamide Chemical compound FC1=CC(I)=CC=C1NC(C(=C1)C(=O)NCC2CC2)=C(F)C2=C1OC=N2 VXSSMUDYMVEHPO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 201000000849 skin cancer Diseases 0.000 claims description 2
- 208000017520 skin disease Diseases 0.000 claims description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 20
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 16
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 15
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 description 22
- 125000000304 alkynyl group Chemical group 0.000 description 16
- 0 CCCC(*)C(*1)=Nc2c1c(*)c(*(C)(C)C(C=C*CC)=CC*)c(C(OC)=O)c2* Chemical compound CCCC(*)C(*1)=Nc2c1c(*)c(*(C)(C)C(C=C*CC)=CC*)c(C(OC)=O)c2* 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- BDVAZGTYKFDZRE-UHFFFAOYSA-N 5-(4-bromo-2-chloroanilino)-n-(cyclopropylmethyl)-4-fluoro-1,3-benzoxazole-6-carboxamide Chemical compound C1CC1CNC(=O)C1=CC=2OC=NC=2C(F)=C1NC1=CC=C(Br)C=C1Cl BDVAZGTYKFDZRE-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical group 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210014021.X | 2012-01-17 | ||
| CN201210014021 | 2012-01-17 | ||
| CN201210190520.4 | 2012-06-08 | ||
| CN201210190520.4A CN103204825B (zh) | 2012-01-17 | 2012-06-08 | 作为蛋白激酶抑制剂的苯并噻唑化合物及其制备方法和用途 |
| CN201210189087.2A CN103204827B (zh) | 2012-01-17 | 2012-06-08 | 作为蛋白激酶抑制剂的苯并噻二唑化合物及其制备方法和用途 |
| CN201210189086.8A CN103204822B (zh) | 2012-01-17 | 2012-06-08 | 作为蛋白激酶抑制剂的苯并噁唑化合物及其制备方法和用途 |
| CN201210189086.8 | 2012-06-08 | ||
| CN201210189087.2 | 2012-06-08 | ||
| PCT/CN2013/000037 WO2013107283A1 (en) | 2012-01-17 | 2013-01-16 | Benzoheterocyclic compounds and use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015503597A JP2015503597A (ja) | 2015-02-02 |
| JP2015503597A5 true JP2015503597A5 (enExample) | 2016-03-10 |
| JP6077006B2 JP6077006B2 (ja) | 2017-02-08 |
Family
ID=48752254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014551508A Active JP6077006B2 (ja) | 2012-01-17 | 2013-01-16 | ベンゾ複素環式化合物およびその使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9290468B2 (enExample) |
| EP (1) | EP2804855B1 (enExample) |
| JP (1) | JP6077006B2 (enExample) |
| CN (3) | CN103204827B (enExample) |
| CA (1) | CA2897259C (enExample) |
| NZ (1) | NZ627631A (enExample) |
| WO (1) | WO2013107283A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104710417B (zh) * | 2013-12-11 | 2020-09-08 | 上海科州药物研发有限公司 | 氮杂吲哚类衍生物及其合成方法 |
| CN105384738B (zh) * | 2014-08-21 | 2017-08-29 | 上海科州药物研发有限公司 | 作为蛋白激酶抑制剂的杂环类化合物及其制备方法和用途 |
| CN105859543A (zh) * | 2016-05-06 | 2016-08-17 | 蚌埠中实化学技术有限公司 | 一种2,6-二氟-4-溴苯甲酰氯的制备方法 |
| WO2020103930A1 (zh) * | 2018-11-22 | 2020-05-28 | 上海科技大学 | 噻唑并环类化合物、其制备方法、中间体和应用 |
| CN114364798A (zh) | 2019-03-21 | 2022-04-15 | 欧恩科斯欧公司 | 用于治疗癌症的Dbait分子与激酶抑制剂的组合 |
| US20220401436A1 (en) | 2019-11-08 | 2022-12-22 | INSERM (Institute National de la Santé et de la Recherche Médicale) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| CN113440616A (zh) * | 2020-03-25 | 2021-09-28 | 上海科州药物研发有限公司 | Ras或raf突变型癌症的联合疗法 |
| EP4663631A1 (en) * | 2023-02-10 | 2025-12-17 | Shanghai Kechow Pharma, Inc. | Polymorph as protein kinase mek inhibitor, and preparation method therefor and use thereof |
| WO2025073765A1 (en) | 2023-10-03 | 2025-04-10 | Institut National de la Santé et de la Recherche Médicale | Methods of prognosis and treatment of patients suffering from melanoma |
| WO2025242163A1 (zh) * | 2024-05-23 | 2025-11-27 | 上海科州药物股份有限公司 | 蛋白激酶mek抑制剂的盐及其用途 |
Family Cites Families (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA73073C2 (uk) | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
| WO1999001426A1 (en) | 1997-07-01 | 1999-01-14 | Warner-Lambert Company | 4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as mek inhibitors |
| NZ501277A (en) | 1997-07-01 | 2002-12-20 | Warner Lambert Co | -2(4-bromo or 4-iodo phenylamino) benzoic acid derivatives and their use as MEK inhibitors |
| US6120451A (en) | 1998-12-31 | 2000-09-19 | General Electric Company | Ultrasound color flow display optimization by adjustment of threshold |
| EP1144385B1 (en) * | 1999-01-13 | 2005-08-17 | Warner-Lambert Company Llc | Benzoheterocycles and their use as mek inhibitors |
| CA2348236A1 (en) | 1999-01-13 | 2000-07-20 | Stephen Douglas Barrett | 4-arylamino, 4-aryloxy, and 4-arylthio diarylamines and derivatives thereof as selective mek inhibitors |
| EE200100374A (et) | 1999-01-13 | 2002-12-16 | Warner-Lambert Company | 1-heterotsükliga asendatud diarüülamiinid |
| JP2000204079A (ja) * | 1999-01-13 | 2000-07-25 | Warner Lambert Co | ジアリ―ルアミン |
| WO2000042002A1 (en) | 1999-01-13 | 2000-07-20 | Warner-Lambert Company | Sulphohydroxamic acids and sulphohydroxamates and their use as mek inhibitors |
| JP2002534446A (ja) | 1999-01-13 | 2002-10-15 | ワーナー−ランバート・カンパニー | ４′ヘテロアリールジアリールアミン |
| GB9910577D0 (en) | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
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-
2012
- 2012-06-08 CN CN201210189087.2A patent/CN103204827B/zh active Active
- 2012-06-08 CN CN201210190520.4A patent/CN103204825B/zh active Active
- 2012-06-08 CN CN201210189086.8A patent/CN103204822B/zh active Active
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2013
- 2013-01-16 US US14/372,731 patent/US9290468B2/en active Active
- 2013-01-16 JP JP2014551508A patent/JP6077006B2/ja active Active
- 2013-01-16 WO PCT/CN2013/000037 patent/WO2013107283A1/en not_active Ceased
- 2013-01-16 CA CA2897259A patent/CA2897259C/en active Active
- 2013-01-16 NZ NZ627631A patent/NZ627631A/en unknown
- 2013-01-16 EP EP13738359.2A patent/EP2804855B1/en active Active
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2016
- 2016-02-22 US US15/050,045 patent/US9937158B2/en active Active
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