JP2020526499A5 - - Google Patents
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- JP2020526499A5 JP2020526499A5 JP2019572412A JP2019572412A JP2020526499A5 JP 2020526499 A5 JP2020526499 A5 JP 2020526499A5 JP 2019572412 A JP2019572412 A JP 2019572412A JP 2019572412 A JP2019572412 A JP 2019572412A JP 2020526499 A5 JP2020526499 A5 JP 2020526499A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- independently
- cyano
- halo
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 167
- -1 chloro, bromo, methyl Chemical group 0.000 claims description 112
- 150000001875 compounds Chemical class 0.000 claims description 98
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 88
- 125000003545 alkoxy group Chemical group 0.000 claims description 82
- 125000005843 halogen group Chemical group 0.000 claims description 68
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
- 150000002148 esters Chemical class 0.000 claims description 54
- 239000000651 prodrug Substances 0.000 claims description 54
- 229940002612 prodrug Drugs 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 54
- 239000012453 solvate Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 125000002252 acyl group Chemical group 0.000 claims description 37
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000002950 monocyclic group Chemical group 0.000 claims description 24
- 125000002619 bicyclic group Chemical group 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 230000035772 mutation Effects 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 8
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 8
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 8
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 206010009944 Colon cancer 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
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
- 208000002495 Uterine Neoplasms Diseases 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 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
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 201000011549 stomach cancer Diseases 0.000 claims description 2
- 206010046766 uterine cancer Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 description 17
- 238000000034 method Methods 0.000 description 13
- 0 CC(C)*1N[C@@](C[C@@](C)I)CC1 Chemical compound CC(C)*1N[C@@](C[C@@](C)I)CC1 0.000 description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- 150000003536 tetrazoles Chemical class 0.000 description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 2
- DFWIEHNMEDMIIL-BYPYZUCNSA-N O[C@@H]1C[IH]CC1 Chemical compound O[C@@H]1C[IH]CC1 DFWIEHNMEDMIIL-BYPYZUCNSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229940043355 kinase inhibitor Drugs 0.000 description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 2
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- XFWYMAUDTKMZNM-FNORWQNLSA-N CNCCN(C)c(cc1)cc(OC)c1NC1=NC2C(c(cc3C#N)cc(CC/C=C/C=O)c3NC)=C2CN1 Chemical compound CNCCN(C)c(cc1)cc(OC)c1NC1=NC2C(c(cc3C#N)cc(CC/C=C/C=O)c3NC)=C2CN1 XFWYMAUDTKMZNM-FNORWQNLSA-N 0.000 description 1
- VFFHVTKUQCVAIG-UHFFFAOYSA-N Cc1c[nH]c(c(C#N)c2)c1cc2-c1ccnc(Nc(cc(c(N(C)CCN(C)C)c2)NC(C=C)=O)c2OC)n1 Chemical compound Cc1c[nH]c(c(C#N)c2)c1cc2-c1ccnc(Nc(cc(c(N(C)CCN(C)C)c2)NC(C=C)=O)c2OC)n1 VFFHVTKUQCVAIG-UHFFFAOYSA-N 0.000 description 1
- IKHRSWSIFCXLQZ-UHFFFAOYSA-N Cc1c[nH]c(c(C(N)=O)c2)c1cc2-c1ccnc(Nc(cc(c(N(C)CCN(C)C)c2)NC(C=C)=O)c2OC)n1 Chemical compound Cc1c[nH]c(c(C(N)=O)c2)c1cc2-c1ccnc(Nc(cc(c(N(C)CCN(C)C)c2)NC(C=C)=O)c2OC)n1 IKHRSWSIFCXLQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 229940121647 egfr inhibitor Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000005961 oxazepanyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000005475 oxolanyl group Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762528697P | 2017-07-05 | 2017-07-05 | |
| US62/528,697 | 2017-07-05 | ||
| PCT/US2018/040904 WO2019010295A1 (en) | 2017-07-05 | 2018-07-05 | SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF EGFR TYROSINE KINASE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020526499A JP2020526499A (ja) | 2020-08-31 |
| JP2020526499A5 true JP2020526499A5 (OSRAM) | 2021-07-26 |
Family
ID=64950363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019572412A Pending JP2020526499A (ja) | 2017-07-05 | 2018-07-05 | Ｅｇｆｒチロシンキナーゼの臨床上重要な突然変異体の選択的阻害剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20200131176A1 (OSRAM) |
| EP (1) | EP3648753A4 (OSRAM) |
| JP (1) | JP2020526499A (OSRAM) |
| KR (1) | KR20200028966A (OSRAM) |
| CN (1) | CN111093645A (OSRAM) |
| CA (1) | CA3068854A1 (OSRAM) |
| WO (1) | WO2019010295A1 (OSRAM) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019501222A (ja) | 2016-01-07 | 2019-01-17 | シーエス ファーマテック リミテッド | Ｅｇｆｒチロシンキナーゼの臨床的に重要な変異体の選択的阻害薬 |
| KR102388312B1 (ko) * | 2017-06-13 | 2022-04-19 | 베이징 아다메이들 바이오테크놀로지 리미티드 라이어빌리티 컴퍼니 | 아미노피리미딘 화합물, 이의 제조방법 및 용도 |
| US20210101881A1 (en) * | 2018-02-12 | 2021-04-08 | Ancureall Pharmaceutical (Shanghai) Co., Ltd. | Pyrimidine compound, preparation method thereof and medical use thereof |
| US12157730B2 (en) | 2019-03-19 | 2024-12-03 | Voronoi Inc. | Heteroaryl derivative, method for producing same, and pharmaceutical composition comprising same as effective component |
| PL3943491T3 (pl) * | 2019-03-19 | 2025-11-17 | Voronoi Inc. | Pochodna heteroarylowa, sposób jej wytwarzania i kompozycja farmaceutyczna zawierająca ją jako skuteczny składnik |
| KR20210142154A (ko) | 2019-03-21 | 2021-11-24 | 옹쎄오 | 암 치료를 위한 키나제 억제제와 조합된 dbait 분자 |
| CN111747950B (zh) | 2019-03-29 | 2024-01-23 | 深圳福沃药业有限公司 | 用于治疗癌症的嘧啶衍生物 |
| WO2020245208A1 (en) | 2019-06-04 | 2020-12-10 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Use of cd9 as a biomarker and as a biotarget in glomerulonephritis or glomerulosclerosis |
| MX2022003769A (es) | 2019-10-03 | 2022-04-20 | Bristol Myers Squibb Co | Indazol carboxamidas como inhibidores de cinasas. |
| CN114761006A (zh) | 2019-11-08 | 2022-07-15 | Inserm(法国国家健康医学研究院) | 对激酶抑制剂产生耐药性的癌症的治疗方法 |
| TW202128670A (zh) * | 2019-11-26 | 2021-08-01 | 大陸商上海翰森生物醫藥科技有限公司 | 含氮多環類衍生物抑制劑、其製備方法和應用 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| WO2021243596A1 (en) * | 2020-06-03 | 2021-12-09 | InventisBio Co., Ltd. | Aminopyrimidine compounds, preparation methods and uses thereof |
| WO2022131741A1 (ko) * | 2020-12-14 | 2022-06-23 | 보로노이바이오 주식회사 | 아이소옥사졸리딘 유도체 화합물 및 이의 용도 |
| KR20240027583A (ko) * | 2021-04-30 | 2024-03-04 | 수조우 푸허 바이오파마 컴퍼니 리미티드 | 폐암 치료를 위한 피리미디닐아미노벤젠 |
| CA3180295A1 (en) | 2021-05-17 | 2022-11-24 | Youn Ho Lee | Heteroaryl derivative compounds, and uses thereof |
| CN113651800B (zh) * | 2021-09-07 | 2022-08-19 | 山东铂源药业股份有限公司 | 一种甲磺酸奥希替尼的制备方法 |
| CN115650974B (zh) * | 2022-08-04 | 2024-06-18 | 天津大学 | N-[5-(嘧啶-2-氨基)-2,4-二取代苯基]-顺式戊二烯酰胺衍生物及应用 |
| WO2024094064A1 (en) * | 2022-11-02 | 2024-05-10 | Suzhou Puhe Biopharma Co., Ltd | Pyrimidinylaminobenzenes for treating lung cancer with distant metastasis |
| AU2023371904A1 (en) * | 2022-11-03 | 2025-04-17 | Voronoi Inc. | Fumarate, tartrate, malate, and citrate salts of an egfr inhibitor |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI458721B (zh) * | 2008-06-27 | 2014-11-01 | Celgene Avilomics Res Inc | 雜芳基化合物及其用途 |
| CN104860941B (zh) * | 2014-02-25 | 2017-03-22 | 上海海雁医药科技有限公司 | 2,4‑二取代苯‑1,5‑二胺衍生物及其应用以及由其制备的药物组合物和药用组合物 |
| WO2016105525A2 (en) * | 2014-12-23 | 2016-06-30 | Dana-Farber Cancer Institute, Inc. | Novel pyrimidines as egfr inhibitors and methods of treating disorders |
| JP2019501222A (ja) * | 2016-01-07 | 2019-01-17 | シーエス ファーマテック リミテッド | Ｅｇｆｒチロシンキナーゼの臨床的に重要な変異体の選択的阻害薬 |
| EP3492462B1 (en) * | 2016-07-26 | 2023-08-30 | Shenzhen TargetRx, Inc. | Amino pyrimidine compound for inhibiting protein tyrosine kinase activity |
-
2018
- 2018-07-05 EP EP18827860.0A patent/EP3648753A4/en not_active Withdrawn
- 2018-07-05 JP JP2019572412A patent/JP2020526499A/ja active Pending
- 2018-07-05 US US16/628,831 patent/US20200131176A1/en not_active Abandoned
- 2018-07-05 CN CN201880044480.8A patent/CN111093645A/zh active Pending
- 2018-07-05 CA CA3068854A patent/CA3068854A1/en not_active Abandoned
- 2018-07-05 KR KR1020207003387A patent/KR20200028966A/ko not_active Withdrawn
- 2018-07-05 WO PCT/US2018/040904 patent/WO2019010295A1/en not_active Ceased
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