JPWO2020009156A5 - - Google Patents
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- Publication number
- JPWO2020009156A5 JPWO2020009156A5 JP2020529034A JP2020529034A JPWO2020009156A5 JP WO2020009156 A5 JPWO2020009156 A5 JP WO2020009156A5 JP 2020529034 A JP2020529034 A JP 2020529034A JP 2020529034 A JP2020529034 A JP 2020529034A JP WO2020009156 A5 JPWO2020009156 A5 JP WO2020009156A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- fluoro
- propa
- group
- piperidine
- 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.)
- Granted
Links
- 239000013078 crystal Substances 0.000 claims 31
- -1 5-methyl-1,3,4-oxadiazole-2-yl Chemical group 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 14
- 238000000634 powder X-ray diffraction Methods 0.000 claims 11
- 230000005855 radiation Effects 0.000 claims 11
- 206010028980 Neoplasm Diseases 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 8
- 230000037431 insertion Effects 0.000 claims 8
- 238000003780 insertion Methods 0.000 claims 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 8
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 7
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims 6
- 230000035772 mutation Effects 0.000 claims 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims 4
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 4
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 4
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims 4
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims 4
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims 4
- 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 4
- VKGDPIFIZRSHPU-UHFFFAOYSA-N 1-[4-[4-[2-fluoro-4-[1-(5-fluoro-6-methylpyridin-3-yl)pyrazol-3-yl]oxyanilino]-7-methoxyquinazolin-6-yl]oxypiperidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(NC2=NC=NC3=CC(=C(C=C23)OC2CCN(CC2)C(C=C)=O)OC)C=CC(=C1)OC1=NN(C=C1)C=1C=NC(=C(C=1)F)C VKGDPIFIZRSHPU-UHFFFAOYSA-N 0.000 claims 3
- COHVRMIFKBUSQQ-UHFFFAOYSA-N 3-[3-fluoro-4-[[7-methoxy-6-(1-prop-2-enoylpiperidin-4-yl)oxyquinazolin-4-yl]amino]phenoxy]-N-(1-fluoro-2-methylpropan-2-yl)pyrazole-1-carboxamide Chemical compound FC=1C=C(OC2=NN(C=C2)C(=O)NC(CF)(C)C)C=CC=1NC1=NC=NC2=CC(=C(C=C12)OC1CCN(CC1)C(C=C)=O)OC COHVRMIFKBUSQQ-UHFFFAOYSA-N 0.000 claims 3
- 206010005003 Bladder cancer Diseases 0.000 claims 3
- 206010006187 Breast cancer Diseases 0.000 claims 3
- 208000026310 Breast neoplasm Diseases 0.000 claims 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 3
- 206010033128 Ovarian cancer Diseases 0.000 claims 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 201000005202 lung cancer Diseases 0.000 claims 3
- 208000020816 lung neoplasm Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 201000005112 urinary bladder cancer Diseases 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- FCDYJWAOZRIKCZ-UHFFFAOYSA-N CS(=O)(=O)O.C(C)(C)(C)NC(=O)N1N=C(C=C1)OC1=CC(=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)OC1CCN(CC1)C(C=C)=O)OC)F Chemical compound CS(=O)(=O)O.C(C)(C)(C)NC(=O)N1N=C(C=C1)OC1=CC(=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)OC1CCN(CC1)C(C=C)=O)OC)F FCDYJWAOZRIKCZ-UHFFFAOYSA-N 0.000 claims 2
- GAENHJPUUAEBEV-UHFFFAOYSA-N N-tert-butyl-3-[3-fluoro-4-[[7-methoxy-6-(1-prop-2-enoylpiperidin-4-yl)oxyquinazolin-4-yl]amino]phenoxy]pyrazole-1-carboxamide Chemical compound C(C)(C)(C)NC(=O)N1N=C(C=C1)OC1=CC(=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)OC1CCN(CC1)C(C=C)=O)OC)F GAENHJPUUAEBEV-UHFFFAOYSA-N 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 238000002703 mutagenesis Methods 0.000 claims 2
- 231100000350 mutagenesis Toxicity 0.000 claims 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- BGKHRRRPRQMKQL-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;prop-2-enal Chemical compound C=CC=O.OC(=O)CC(O)(C(O)=O)CC(O)=O BGKHRRRPRQMKQL-UHFFFAOYSA-N 0.000 claims 1
- COOCHZXIHFLMNV-UHFFFAOYSA-N C1(=CC=CC=2C(=CC=CC12)S(=O)(=O)O)S(=O)(=O)O.C(C=C)=O Chemical compound C1(=CC=CC=2C(=CC=CC12)S(=O)(=O)O)S(=O)(=O)O.C(C=C)=O COOCHZXIHFLMNV-UHFFFAOYSA-N 0.000 claims 1
- ZMXCFLLCFFCQIE-UHFFFAOYSA-N CC(C)(CF)NC(=O)N1C=CC(=N1)OC2=CC(=C(C=C2)NC3=NC=NC4=CC(=C(C=C43)OC5CCN(CC5)C(=O)C=C)OC)F.C1=CC2=C(C=CC=C2S(=O)(=O)O)C(=C1)S(=O)(=O)O Chemical compound CC(C)(CF)NC(=O)N1C=CC(=N1)OC2=CC(=C(C=C2)NC3=NC=NC4=CC(=C(C=C43)OC5CCN(CC5)C(=O)C=C)OC)F.C1=CC2=C(C=CC=C2S(=O)(=O)O)C(=C1)S(=O)(=O)O ZMXCFLLCFFCQIE-UHFFFAOYSA-N 0.000 claims 1
- OITIZWFIUUVEFC-UHFFFAOYSA-N CC1=C(C=C(C=N1)N2C=CC(=N2)OC3=CC(=C(C=C3)NC4=NC=NC5=CC(=C(C=C54)OC6CCN(CC6)C(=O)C=C)OC)F)F.C(C(=O)O)C(CC(=O)O)(C(=O)O)O Chemical compound CC1=C(C=C(C=N1)N2C=CC(=N2)OC3=CC(=C(C=C3)NC4=NC=NC5=CC(=C(C=C54)OC6CCN(CC6)C(=O)C=C)OC)F)F.C(C(=O)O)C(CC(=O)O)(C(=O)O)O OITIZWFIUUVEFC-UHFFFAOYSA-N 0.000 claims 1
- SYHCFFBKVHPNBQ-UHFFFAOYSA-N CC1=C(C=C(C=N1)N2C=CC(=N2)OC3=CC(=C(C=C3)NC4=NC=NC5=CC(=C(C=C54)OC6CCN(CC6)C(=O)C=C)OC)F)F.C(C(C(=O)O)O)(C(=O)O)O Chemical compound CC1=C(C=C(C=N1)N2C=CC(=N2)OC3=CC(=C(C=C3)NC4=NC=NC5=CC(=C(C=C54)OC6CCN(CC6)C(=O)C=C)OC)F)F.C(C(C(=O)O)O)(C(=O)O)O SYHCFFBKVHPNBQ-UHFFFAOYSA-N 0.000 claims 1
- DXSQJCNTRDXTOP-UHFFFAOYSA-N CC1=C(C=C(C=N1)N2C=CC(=N2)OC3=CC(=C(C=C3)NC4=NC=NC5=CC(=C(C=C54)OC6CCN(CC6)C(=O)C=C)OC)F)F.C1=CC=C(C=C1)S(=O)(=O)O Chemical compound CC1=C(C=C(C=N1)N2C=CC(=N2)OC3=CC(=C(C=C3)NC4=NC=NC5=CC(=C(C=C54)OC6CCN(CC6)C(=O)C=C)OC)F)F.C1=CC=C(C=C1)S(=O)(=O)O DXSQJCNTRDXTOP-UHFFFAOYSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- CXYNQYMJBXSWIU-UHFFFAOYSA-N prop-2-enal hydrochloride Chemical compound Cl.C=CC=O CXYNQYMJBXSWIU-UHFFFAOYSA-N 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018127829 | 2018-07-04 | ||
| JP2018127829 | 2018-07-04 | ||
| PCT/JP2019/026483 WO2020009156A1 (ja) | 2018-07-04 | 2019-07-03 | ビアリールエーテル型キナゾリン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPWO2020009156A1 JPWO2020009156A1 (ja) | 2021-07-15 |
| JPWO2020009156A5 true JPWO2020009156A5 (https=) | 2022-05-26 |
| JP7288904B2 JP7288904B2 (ja) | 2023-06-08 |
Family
ID=69059535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020529034A Active JP7288904B2 (ja) | 2018-07-04 | 2019-07-03 | ビアリールエーテル型キナゾリン誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20230025510A1 (https=) |
| EP (1) | EP3822263A4 (https=) |
| JP (1) | JP7288904B2 (https=) |
| KR (1) | KR20210029165A (https=) |
| CN (1) | CN112334460A (https=) |
| AU (1) | AU2019297889A1 (https=) |
| BR (1) | BR112020027064A2 (https=) |
| CA (1) | CA3105602A1 (https=) |
| CO (1) | CO2021000800A2 (https=) |
| IL (1) | IL279858A (https=) |
| MX (1) | MX2021000014A (https=) |
| PH (1) | PH12021550003A1 (https=) |
| SG (1) | SG11202013218QA (https=) |
| TW (1) | TW202012391A (https=) |
| WO (1) | WO2020009156A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020262998A1 (ko) * | 2019-06-26 | 2020-12-30 | 한미약품 주식회사 | 항 종양 활성을 갖는 신규 퀴나졸린 유도체 및 이를 포함하는 약학 조성물 |
| US20230271936A1 (en) * | 2020-08-10 | 2023-08-31 | Abbisko Therapeutics Co., Ltd | Efgr inhibitor, preparation method therefor and application thereof |
| WO2022105908A1 (zh) * | 2020-11-23 | 2022-05-27 | 上海和誉生物医药科技有限公司 | Egfr抑制剂及其制备方法与在药学上的应用 |
| CN113264888A (zh) * | 2021-03-04 | 2021-08-17 | 江苏康可得生物技术股份有限公司 | 酪氨酸激酶抑制剂及其药物应用 |
| KR20230156767A (ko) * | 2021-03-19 | 2023-11-14 | 베이징 사이텍-엠큐 파마슈티컬즈 리미티드 | 퀴나졸린계 화합물, 조성물 및 퀴나졸린계 화합물의 적용 |
| EP4323356A1 (en) | 2021-04-13 | 2024-02-21 | Nuvalent, Inc. | Amino-substituted heterocycles for treating cancers with egfr mutations |
| US20250136595A1 (en) * | 2022-02-09 | 2025-05-01 | Enliven Inc. | Acylated heterocyclic quinazoline derivatives as inhibitors of erbb2 |
| TW202404590A (zh) * | 2022-04-05 | 2024-02-01 | 美商纜圖藥品公司 | Ｅｇｆｒ抑制劑 |
| CN117384162A (zh) * | 2022-05-17 | 2024-01-12 | 浙江文达医药科技有限公司 | 选择性her2抑制剂 |
| WO2025167927A1 (zh) * | 2024-02-05 | 2025-08-14 | 苏州韬略生物科技股份有限公司 | 三取代喹唑啉衍生物及其酸加成盐及其药物组合物和用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU228446B1 (en) * | 1996-04-12 | 2013-03-28 | Warner Lambert Co | Kinazoline derivatives as irreversible inhibitors of protein-kinase, pharmaceutical compositions containing these compounds and use thereof |
| CA2527017A1 (en) * | 2003-05-27 | 2004-12-09 | Pfizer Products Inc. | Quinazolines and pyrido [3,4-d] pyrimidines as receptor tyrosine kinase inhibitors |
| TWI377944B (en) * | 2007-06-05 | 2012-12-01 | Hanmi Holdings Co Ltd | Novel amide derivative for inhibiting the growth of cancer cells |
| WO2013173254A1 (en) * | 2012-05-14 | 2013-11-21 | Dawei Zhang | Bicyclic compounds as kinases inhibitors |
| CN103965120B (zh) * | 2013-01-25 | 2016-08-17 | 上海医药集团股份有限公司 | 喹啉及喹唑啉衍生物、制备方法、中间体、组合物及应用 |
| MA46852A (fr) | 2016-11-17 | 2019-09-25 | Univ Texas | Composés à activité antitumorale contre des cellules cancéreuses porteuses de mutations egfr ou her2 exon 20 |
| WO2020262998A1 (ko) * | 2019-06-26 | 2020-12-30 | 한미약품 주식회사 | 항 종양 활성을 갖는 신규 퀴나졸린 유도체 및 이를 포함하는 약학 조성물 |
-
2019
- 2019-07-02 TW TW108123293A patent/TW202012391A/zh unknown
- 2019-07-03 WO PCT/JP2019/026483 patent/WO2020009156A1/ja not_active Ceased
- 2019-07-03 CA CA3105602A patent/CA3105602A1/en active Pending
- 2019-07-03 JP JP2020529034A patent/JP7288904B2/ja active Active
- 2019-07-03 BR BR112020027064-4A patent/BR112020027064A2/pt not_active Application Discontinuation
- 2019-07-03 AU AU2019297889A patent/AU2019297889A1/en not_active Abandoned
- 2019-07-03 KR KR1020207038066A patent/KR20210029165A/ko not_active Withdrawn
- 2019-07-03 MX MX2021000014A patent/MX2021000014A/es unknown
- 2019-07-03 EP EP19830650.8A patent/EP3822263A4/en not_active Withdrawn
- 2019-07-03 CN CN201980044514.8A patent/CN112334460A/zh active Pending
- 2019-07-03 SG SG11202013218QA patent/SG11202013218QA/en unknown
- 2019-07-03 US US17/257,238 patent/US20230025510A1/en not_active Abandoned
-
2020
- 2020-12-30 IL IL279858A patent/IL279858A/en unknown
-
2021
- 2021-01-03 PH PH12021550003A patent/PH12021550003A1/en unknown
- 2021-01-25 CO CONC2021/0000800A patent/CO2021000800A2/es unknown
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