JP2020505396A5 - - Google Patents
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- JP2020505396A5 JP2020505396A5 JP2019540041A JP2019540041A JP2020505396A5 JP 2020505396 A5 JP2020505396 A5 JP 2020505396A5 JP 2019540041 A JP2019540041 A JP 2019540041A JP 2019540041 A JP2019540041 A JP 2019540041A JP 2020505396 A5 JP2020505396 A5 JP 2020505396A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pharmaceutically acceptable
- prodrug
- acceptable salt
- stereoisomer
- 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 66
- 150000003839 salts Chemical class 0.000 claims description 34
- 229940002612 prodrug Drugs 0.000 claims description 33
- 239000000651 prodrug Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 102200124918 rs121913250 Human genes 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 16
- 102100029974 GTPase HRas Human genes 0.000 claims description 14
- 102100030708 GTPase KRas Human genes 0.000 claims description 14
- 101000584633 Homo sapiens GTPase HRas Proteins 0.000 claims description 14
- 101000584612 Homo sapiens GTPase KRas Proteins 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 12
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 230000035772 mutation Effects 0.000 claims description 11
- 125000002837 carbocyclic group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 102200006538 rs121913530 Human genes 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 102200006614 rs104894229 Human genes 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 102000008300 Mutant Proteins Human genes 0.000 claims description 4
- 108010021466 Mutant Proteins Proteins 0.000 claims description 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
- 201000005787 hematologic cancer Diseases 0.000 claims description 4
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 201000002528 pancreatic cancer Diseases 0.000 claims description 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
- 208000015768 polyposis Diseases 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 206010027476 Metastases Diseases 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 230000009401 metastasis Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 230000035755 proliferation Effects 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 230000000155 isotopic effect Effects 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 102100039788 GTPase NRas Human genes 0.000 claims 1
- 101000744505 Homo sapiens GTPase NRas Proteins 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229910017464 nitrogen compound Inorganic materials 0.000 claims 1
- 150000002830 nitrogen compounds Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 0 CN(C)C1CN(*)C1 Chemical compound CN(C)C1CN(*)C1 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- FFNLWEUALKRHIF-UHFFFAOYSA-N C=CC(N(C1)CC1N(C=C(CCN(c1c(cccc2)c2cc(O)c1)C1=O)C1=C1)C1=O)=O Chemical compound C=CC(N(C1)CC1N(C=C(CCN(c1c(cccc2)c2cc(O)c1)C1=O)C1=C1)C1=O)=O FFNLWEUALKRHIF-UHFFFAOYSA-N 0.000 description 1
- XWJFQIKXCKGGCK-UHFFFAOYSA-N C=CC(N(C1)CC1N(C=Nc1c2cncc1Nc1c(cccc3)c3cc(O)c1)C2=O)=O Chemical compound C=CC(N(C1)CC1N(C=Nc1c2cncc1Nc1c(cccc3)c3cc(O)c1)C2=O)=O XWJFQIKXCKGGCK-UHFFFAOYSA-N 0.000 description 1
- PZLHLJCYHSJRPO-UHFFFAOYSA-N C=CC(N(C1)CC1c(nc1C#N)nc(N=CN2c3cc(O)cc4ccccc34)c1C2=O)=O Chemical compound C=CC(N(C1)CC1c(nc1C#N)nc(N=CN2c3cc(O)cc4ccccc34)c1C2=O)=O PZLHLJCYHSJRPO-UHFFFAOYSA-N 0.000 description 1
- MNGVGWBMEWRXKJ-UHFFFAOYSA-N CC(N(C1=O)c(c(F)ccc2)c2O)=Cc2c1nc[n]2C(C1)CN1C(C=C)=O Chemical compound CC(N(C1=O)c(c(F)ccc2)c2O)=Cc2c1nc[n]2C(C1)CN1C(C=C)=O MNGVGWBMEWRXKJ-UHFFFAOYSA-N 0.000 description 1
- ILBZSNOGPTUKHC-UHFFFAOYSA-N CC1CN(C)C1 Chemical compound CC1CN(C)C1 ILBZSNOGPTUKHC-UHFFFAOYSA-N 0.000 description 1
- CVMPATQNGCTWPN-UHFFFAOYSA-N CN(C(C(C1)CN1C(C=C)=O)=NC(CCN1c2cc(O)cc3ccccc23)=C2C1=O)C2=O Chemical compound CN(C(C(C1)CN1C(C=C)=O)=NC(CCN1c2cc(O)cc3ccccc23)=C2C1=O)C2=O CVMPATQNGCTWPN-UHFFFAOYSA-N 0.000 description 1
- UNPPKRYQBIFBRX-UHFFFAOYSA-N Cc(ccc1c2cn[nH]1)c2N(C=Nc1c2c(C#N)nc(C(C3)CN3C(C=C)=O)n1)C2=O Chemical compound Cc(ccc1c2cn[nH]1)c2N(C=Nc1c2c(C#N)nc(C(C3)CN3C(C=C)=O)n1)C2=O UNPPKRYQBIFBRX-UHFFFAOYSA-N 0.000 description 1
- GVFZIQUPIGUBQJ-UHFFFAOYSA-N Cc(ccc1c2cn[nH]1)c2N(C=Nc1nc(C(C2)CN2C(C=C)=O)nc(C(N)=O)c11)C1=O Chemical compound Cc(ccc1c2cn[nH]1)c2N(C=Nc1nc(C(C2)CN2C(C=C)=O)nc(C(N)=O)c11)C1=O GVFZIQUPIGUBQJ-UHFFFAOYSA-N 0.000 description 1
- XLMVGHCERAYHBW-UHFFFAOYSA-N Cc(ccc1c2cn[nH]1)c2N(CCC(C1=C2)=CN(C(C3)CN3C(C=C)=O)C2=O)C1=O Chemical compound Cc(ccc1c2cn[nH]1)c2N(CCC(C1=C2)=CN(C(C3)CN3C(C=C)=O)C2=O)C1=O XLMVGHCERAYHBW-UHFFFAOYSA-N 0.000 description 1
- OBPBXIDBCSCMIL-UHFFFAOYSA-N Cc1ccc2[nH]ncc2c1N(CCC(N=C(C(C1)CN1C(C=C)=O)N1C)=C2C1=O)C2=O Chemical compound Cc1ccc2[nH]ncc2c1N(CCC(N=C(C(C1)CN1C(C=C)=O)N1C)=C2C1=O)C2=O OBPBXIDBCSCMIL-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
- 125000004474 heteroalkylene group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023122385A JP2023129662A (ja) | 2017-01-26 | 2023-07-27 | 縮合ヘテロ－ヘテロ二環式化合物およびその使用方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762450962P | 2017-01-26 | 2017-01-26 | |
| US62/450,962 | 2017-01-26 | ||
| PCT/US2018/015233 WO2018140600A1 (en) | 2017-01-26 | 2018-01-25 | Fused hetero-hetero bicyclic compounds and methods of use thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023122385A Division JP2023129662A (ja) | 2017-01-26 | 2023-07-27 | 縮合ヘテロ－ヘテロ二環式化合物およびその使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020505396A JP2020505396A (ja) | 2020-02-20 |
| JP2020505396A5 true JP2020505396A5 (enExample) | 2021-03-04 |
| JP7327802B2 JP7327802B2 (ja) | 2023-08-16 |
Family
ID=61189557
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019540041A Active JP7327802B2 (ja) | 2017-01-26 | 2018-01-25 | 縮合ヘテロ－ヘテロ二環式化合物およびその使用方法 |
| JP2023122385A Pending JP2023129662A (ja) | 2017-01-26 | 2023-07-27 | 縮合ヘテロ－ヘテロ二環式化合物およびその使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023122385A Pending JP2023129662A (ja) | 2017-01-26 | 2023-07-27 | 縮合ヘテロ－ヘテロ二環式化合物およびその使用方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US11059819B2 (enExample) |
| EP (1) | EP3573967A1 (enExample) |
| JP (2) | JP7327802B2 (enExample) |
| CN (1) | CN110382482A (enExample) |
| WO (1) | WO2018140600A1 (enExample) |
Families Citing this family (118)
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|---|---|---|---|---|
| US9227978B2 (en) | 2013-03-15 | 2016-01-05 | Araxes Pharma Llc | Covalent inhibitors of Kras G12C |
| JO3805B1 (ar) | 2013-10-10 | 2021-01-31 | Araxes Pharma Llc | مثبطات كراس جي12سي |
| ES2898765T3 (es) | 2015-04-10 | 2022-03-08 | Araxes Pharma Llc | Compuestos de quinazolina sustituidos y métodos de uso de los mismos |
| EP3356347A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| US10975071B2 (en) | 2015-09-28 | 2021-04-13 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| US10689356B2 (en) | 2015-09-28 | 2020-06-23 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| EP3356353A1 (en) | 2015-09-28 | 2018-08-08 | Araxes Pharma LLC | Inhibitors of kras g12c mutant proteins |
| US10730867B2 (en) | 2015-09-28 | 2020-08-04 | Araxes Pharma Llc | Inhibitors of KRAS G12C mutant proteins |
| WO2017058792A1 (en) | 2015-09-28 | 2017-04-06 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| US10414757B2 (en) | 2015-11-16 | 2019-09-17 | Araxes Pharma Llc | 2-substituted quinazoline compounds comprising a substituted heterocyclic group and methods of use thereof |
| WO2017172979A1 (en) | 2016-03-30 | 2017-10-05 | Araxes Pharma Llc | Substituted quinazoline compounds and methods of use |
| SG11201810171SA (en) | 2016-05-18 | 2018-12-28 | Mirati Therapeutics Inc | Kras g12c inhibitors |
| WO2018064510A1 (en) | 2016-09-29 | 2018-04-05 | Araxes Pharma Llc | Inhibitors of kras g12c mutant proteins |
| EP3573954A1 (en) | 2017-01-26 | 2019-12-04 | Araxes Pharma LLC | Fused bicyclic benzoheteroaromatic compounds and methods of use thereof |
| EP3573971A1 (en) | 2017-01-26 | 2019-12-04 | Araxes Pharma LLC | 1-(3-(6-(3-hydroxynaphthalen-1-yl)benzofuran-2-yl)azetidin-1yl)prop-2-en-1-one derivatives and similar compounds as kras g12c modulators for treating cancer |
| WO2018140599A1 (en) | 2017-01-26 | 2018-08-02 | Araxes Pharma Llc | Benzothiophene and benzothiazole compounds and methods of use thereof |
| US11136308B2 (en) | 2017-01-26 | 2021-10-05 | Araxes Pharma Llc | Substituted quinazoline and quinazolinone compounds and methods of use thereof |
| KR20200010306A (ko) | 2017-05-25 | 2020-01-30 | 아락세스 파마 엘엘씨 | Kras의 공유적 억제제 |
| CN110869357A (zh) | 2017-05-25 | 2020-03-06 | 亚瑞克西斯制药公司 | 化合物及其用于治疗癌症的使用方法 |
| WO2018218069A1 (en) | 2017-05-25 | 2018-11-29 | Araxes Pharma Llc | Quinazoline derivatives as modulators of mutant kras, hras or nras |
| US10647715B2 (en) | 2017-11-15 | 2020-05-12 | Mirati Therapeutics, Inc. | KRas G12C inhibitors |
| PT3710439T (pt) | 2017-11-15 | 2023-05-15 | Array Biopharma Inc | Inibidores de kras g12c |
| ES2969284T3 (es) | 2018-01-19 | 2024-05-17 | Medshine Discovery Inc | Derivado de piridona-pirimidina que actúa como inhibidor de la muteína krasg12c |
| WO2019217307A1 (en) | 2018-05-07 | 2019-11-14 | Mirati Therapeutics, Inc. | Kras g12c inhibitors |
| TW202012415A (zh) | 2018-05-08 | 2020-04-01 | 瑞典商阿斯特捷利康公司 | 化學化合物 |
| CA3107168A1 (en) | 2018-08-01 | 2020-02-06 | Araxes Pharma Llc | Heterocyclic spiro compounds and methods of use thereof for the treatment of cancer |
| JP2022500385A (ja) * | 2018-09-10 | 2022-01-04 | ミラティ セラピューティクス， インコーポレイテッド | 組み合わせ療法 |
| PT3849534T (pt) * | 2018-09-10 | 2025-04-01 | Mirati Therapeutics Inc | Combinação de dasatinib e adagrasib para utilização no tratamento de cancro do pulmão de células não pequenas |
| EP3849537B1 (en) * | 2018-09-10 | 2024-10-23 | Mirati Therapeutics, Inc. | Combination therapies |
| IL281344B2 (en) | 2018-09-10 | 2025-09-01 | Mirati Therapeutics Inc | Combination of adagrasib and cetuximab for cancer treatment |
| CA3111980A1 (en) | 2018-09-10 | 2020-03-19 | Mirati Therapeutics, Inc. | Combination therapies |
| JP7451419B2 (ja) | 2018-10-26 | 2024-03-18 | 大鵬薬品工業株式会社 | 新規なインダゾール化合物又はその塩 |
| CA3112129A1 (en) | 2018-12-05 | 2020-06-11 | Mirati Therapeutics, Inc. | Combination therapies |
| EP3908283A4 (en) | 2019-01-10 | 2022-10-12 | Mirati Therapeutics, Inc. | KRAS G12C INHIBITORS |
| WO2020165732A1 (en) | 2019-02-12 | 2020-08-20 | Novartis Ag | Pharmaceutical combination comprising tno155 and a krasg12c inhibitor |
| CR20210504A (es) | 2019-03-05 | 2022-02-08 | Astrazeneca Ab | Compuestos tricíclicos condensados útiles como agentes anticancerígenos |
| WO2020234103A1 (en) | 2019-05-21 | 2020-11-26 | Bayer Aktiengesellschaft | Identification and use of kras inhibitors |
| CN110256421A (zh) * | 2019-06-26 | 2019-09-20 | 微境生物医药科技(上海)有限公司 | Kras-g12c抑制剂 |
| CN112300153B (zh) * | 2019-07-26 | 2023-06-13 | 博瑞生物医药（苏州）股份有限公司 | 一种杂环化合物、药物组合物和用途 |
| CN112300173B (zh) * | 2019-07-30 | 2021-10-01 | 上海凌达生物医药有限公司 | 一类含氮多环类化合物、制备方法和用途 |
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| US12122787B2 (en) | 2019-09-20 | 2024-10-22 | Shanghai Jemincare Pharmaceuticals Co., Ltd | Fused pyridone compound, and preparation method therefor and use thereof |
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| JP7823816B2 (ja) | 2019-11-04 | 2026-03-04 | レヴォリューション・メディスンズ，インコーポレイテッド | Ｒａｓ阻害剤 |
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-
2018
- 2018-01-25 WO PCT/US2018/015233 patent/WO2018140600A1/en not_active Ceased
- 2018-01-25 CN CN201880008591.3A patent/CN110382482A/zh active Pending
- 2018-01-25 US US16/480,874 patent/US11059819B2/en not_active Expired - Fee Related
- 2018-01-25 EP EP18704374.0A patent/EP3573967A1/en not_active Withdrawn
- 2018-01-25 JP JP2019540041A patent/JP7327802B2/ja active Active
-
2023
- 2023-07-27 JP JP2023122385A patent/JP2023129662A/ja active Pending
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