RU2769694C2 - C5-Анилинохиназолиновые соединения и их использование в лечении рака - Google Patents
C5-Анилинохиназолиновые соединения и их использование в лечении рака Download PDFInfo
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- RU2769694C2 RU2769694C2 RU2019136279A RU2019136279A RU2769694C2 RU 2769694 C2 RU2769694 C2 RU 2769694C2 RU 2019136279 A RU2019136279 A RU 2019136279A RU 2019136279 A RU2019136279 A RU 2019136279A RU 2769694 C2 RU2769694 C2 RU 2769694C2
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- Prior art keywords
- compound
- triazol
- amino
- acetamide
- phenyl
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- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 52
- 201000011510 cancer Diseases 0.000 title claims abstract description 46
- 238000011282 treatment Methods 0.000 title claims abstract description 34
- LKOVMZOJAULFNX-UHFFFAOYSA-N n-phenylquinazolin-5-amine Chemical class C=1C=CC2=NC=NC=C2C=1NC1=CC=CC=C1 LKOVMZOJAULFNX-UHFFFAOYSA-N 0.000 title description 2
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- 239000011737 fluorine Chemical group 0.000 claims abstract description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
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- FLJOFQUXYAWOPE-UHFFFAOYSA-N N-[4-[[5-fluoro-7-(2-methoxyethoxy)quinazolin-4-yl]amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound FC1=C2C(=NC=NC2=CC(=C1)OCCOC)NC1=CC=C(C=C1)NC(CN1N=NC(=C1)C(C)C)=O FLJOFQUXYAWOPE-UHFFFAOYSA-N 0.000 claims description 32
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 26
- 241001465754 Metazoa Species 0.000 claims description 17
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- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
- SRGPWBUXBAUYDE-UHFFFAOYSA-N N-[4-[(5,7-dimethoxyquinazolin-4-yl)amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound COC1=CC(OC)=C2C(NC3=CC=C(NC(=O)CN4C=C(N=N4)C(C)C)C=C3)=NC=NC2=C1 SRGPWBUXBAUYDE-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003566 oxetanyl group Chemical group 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- MFPLMURQMQGFCG-UHFFFAOYSA-N 2-(4-propan-2-yltriazol-1-yl)-N-[4-[(5,6,7-trimethoxyquinazolin-4-yl)amino]phenyl]acetamide Chemical compound COC1=C(OC)C(OC)=C2C(NC3=CC=C(NC(=O)CN4C=C(N=N4)C(C)C)C=C3)=NC=NC2=C1 MFPLMURQMQGFCG-UHFFFAOYSA-N 0.000 claims description 3
- FBFRRDLCELTRHJ-UHFFFAOYSA-N N-[4-[(5,7-diethoxyquinazolin-4-yl)amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound C(C)OC1=C2C(=NC=NC2=CC(=C1)OCC)NC1=CC=C(C=C1)NC(CN1N=NC(=C1)C(C)C)=O FBFRRDLCELTRHJ-UHFFFAOYSA-N 0.000 claims description 3
- LZALBHKSKNGTHH-UHFFFAOYSA-N N-[4-[(5,7-dimethoxyquinazolin-4-yl)amino]-3-fluorophenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound COC1=CC(OC)=C2C(NC3=C(F)C=C(NC(=O)CN4C=C(N=N4)C(C)C)C=C3)=NC=NC2=C1 LZALBHKSKNGTHH-UHFFFAOYSA-N 0.000 claims description 3
- ZIDCCLUJGIGJMQ-UHFFFAOYSA-N N-[4-[(5-ethoxy-7-methoxyquinazolin-4-yl)amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound CCOC1=C2C(NC3=CC=C(NC(=O)CN4C=C(N=N4)C(C)C)C=C3)=NC=NC2=CC(OC)=C1 ZIDCCLUJGIGJMQ-UHFFFAOYSA-N 0.000 claims description 3
- GQSOEXIDXOEEPP-UHFFFAOYSA-N N-[4-[(5-fluoro-6,7-dimethoxyquinazolin-4-yl)amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound COC1=C(OC)C(F)=C2C(NC3=CC=C(NC(=O)CN4C=C(N=N4)C(C)C)C=C3)=NC=NC2=C1 GQSOEXIDXOEEPP-UHFFFAOYSA-N 0.000 claims description 3
- ZHSBZQFDAKQEPZ-UHFFFAOYSA-N N-[4-[(5-fluoro-7-methoxyquinazolin-4-yl)amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound COC1=CC(F)=C2C(NC3=CC=C(NC(=O)CN4C=C(N=N4)C(C)C)C=C3)=NC=NC2=C1 ZHSBZQFDAKQEPZ-UHFFFAOYSA-N 0.000 claims description 3
- ADVRHODTWBXWRD-UHFFFAOYSA-N N-[4-[(5-methoxy-7-propan-2-yloxyquinazolin-4-yl)amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound COC1=C2C(NC3=CC=C(NC(=O)CN4C=C(N=N4)C(C)C)C=C3)=NC=NC2=CC(OC(C)C)=C1 ADVRHODTWBXWRD-UHFFFAOYSA-N 0.000 claims description 3
- KNIDFCMWOFTDMU-UHFFFAOYSA-N N-[4-[(7-ethoxy-5-methoxyquinazolin-4-yl)amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound CCOC1=CC(OC)=C2C(NC3=CC=C(NC(=O)CN4C=C(N=N4)C(C)C)C=C3)=NC=NC2=C1 KNIDFCMWOFTDMU-UHFFFAOYSA-N 0.000 claims description 3
- IIKVGFPGSYHKNK-UHFFFAOYSA-N N-[4-[[5-ethoxy-7-(oxan-4-yloxy)quinazolin-4-yl]amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound C(C)OC1=C2C(=NC=NC2=CC(=C1)OC1CCOCC1)NC1=CC=C(C=C1)NC(CN1N=NC(=C1)C(C)C)=O IIKVGFPGSYHKNK-UHFFFAOYSA-N 0.000 claims description 3
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- HLZBMFSNSIXJLW-FQEVSTJZSA-N N-[4-[[5-ethoxy-7-[(3S)-oxolan-3-yl]oxyquinazolin-4-yl]amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound CCOC1=C2C(NC3=CC=C(NC(=O)CN4C=C(N=N4)C(C)C)C=C3)=NC=NC2=CC(O[C@H]2CCOC2)=C1 HLZBMFSNSIXJLW-FQEVSTJZSA-N 0.000 claims description 3
- FMZCELDVKFMZNZ-UHFFFAOYSA-N N-[4-[[5-methoxy-7-(2-methoxyethoxy)quinazolin-4-yl]amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound COCCOC1=CC(OC)=C2C(NC3=CC=C(NC(=O)CN4C=C(N=N4)C(C)C)C=C3)=NC=NC2=C1 FMZCELDVKFMZNZ-UHFFFAOYSA-N 0.000 claims description 3
- VFEQCPUSIATBEI-UHFFFAOYSA-N N-[4-[[5-methoxy-7-(oxan-4-yloxy)quinazolin-4-yl]amino]phenyl]-2-(4-propan-2-yltriazol-1-yl)acetamide Chemical compound COC1=C2C(NC3=CC=C(NC(=O)CN4C=C(N=N4)C(C)C)C=C3)=NC=NC2=CC(OC2CCOCC2)=C1 VFEQCPUSIATBEI-UHFFFAOYSA-N 0.000 claims description 3
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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| AR117788A1 (es) * | 2019-01-14 | 2021-08-25 | Pi Industries Ltd | Compuestos de fenilamidina 3-sustituida, preparación y uso |
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| WO2022040341A1 (en) * | 2020-08-20 | 2022-02-24 | The Board Of Trustees Of The Leland Stanford Junior University | Abscopal therapy for cancer |
| CN116782933A (zh) | 2020-09-10 | 2023-09-19 | 健玛保 | 用于治疗弥漫性大b细胞淋巴瘤的联合疗法中的针对cd3和cd20的双特异性抗体 |
| KR20230066040A (ko) | 2020-09-10 | 2023-05-12 | 젠맵 에이/에스 | 만성 림프구성 백혈병을 치료하기 위한 cd3 및 cd20에 대한 이중특이적 항체 |
| CA3189883A1 (en) | 2020-09-10 | 2022-03-17 | Brian Elliott | Bispecific antibody against cd3 and cd20 in combination therapy for treating follicular lymphoma |
| CA3190376A1 (en) | 2020-09-10 | 2022-03-17 | Brian Elliott | Bispecific antibody against cd3 and cd20 in combination therapy for treating follicular lymphoma |
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| US20060178382A1 (en) * | 2003-06-17 | 2006-08-10 | Astrazeneca Ab | Chinazoline derivatives as aurora kinase inhibitors |
| US7709479B1 (en) * | 1999-09-21 | 2010-05-04 | Astrazeneca | Quinazoline derivatives and their use as pharmaceuticals |
| RU2434010C2 (ru) * | 2007-06-05 | 2011-11-20 | Ханми Фарм. Ко., Лтд. | Новое амидное производное для ингибирования роста раковых клеток |
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| GB9514265D0 (en) | 1995-07-13 | 1995-09-13 | Wellcome Found | Hetrocyclic compounds |
| DK1382604T3 (da) | 2001-04-27 | 2006-04-18 | Kirin Brewery | Quinolinderivater med en azolylgruppe og quinazolinderivater |
| EP1684762A4 (en) * | 2003-11-13 | 2009-06-17 | Ambit Biosciences Corp | UREA DERIVATIVES AS MODULATORS OF KINASE |
| BRPI0516093A (pt) | 2004-10-12 | 2008-08-19 | Astrazeneca Ab | derivado de quinazolina, processo para a preparação do mesmo, composição farmacêutica, uso de um derivado de quinazolina, e, método para tratamento de distúrbios proliferativos celulares em um animal de sanque quente |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| US20070106549A1 (en) | 2005-11-04 | 2007-05-10 | Stocking Christine A | Turnkey aviation budget management |
| UY30183A1 (es) | 2006-03-02 | 2007-10-31 | Astrazeneca Ab | Derivados de quinolina |
| WO2008089310A2 (en) | 2007-01-18 | 2008-07-24 | Lexicon Pharmaceuticals, Inc. | Delta 5 desaturase inhibitors for the treatment of obesity |
| US20080194557A1 (en) | 2007-01-18 | 2008-08-14 | Joseph Barbosa | Methods and compositions for the treatment of pain, inflammation and cancer |
| AU2009246263B2 (en) | 2008-05-14 | 2014-08-21 | Amgen Inc. | Combinations VEGF(R) inhibitors and hepatocyte growth factor (c-Met) inhibitors for the treatment of cancer |
| WO2011153553A2 (en) | 2010-06-04 | 2011-12-08 | The Regents Of The University Of California | Methods and compositions for kinase inhibition |
| CN102532042A (zh) * | 2010-12-30 | 2012-07-04 | 上海医药工业研究院 | 一种芳基脲类化合物、其中间体及其应用 |
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| CN103254142B (zh) | 2013-04-26 | 2015-10-28 | 浙江工业大学 | 4-[4-(2-取代氨基乙酰氨基)苯胺基]喹唑啉类衍生物及制备和应用 |
| WO2014181287A1 (en) | 2013-05-09 | 2014-11-13 | Piramal Enterprises Limited | Heterocyclyl compounds and uses thereof |
| CN104130200B (zh) | 2014-07-01 | 2016-04-20 | 中山大学 | 一种2-取代苯基-4-芳胺基喹唑啉衍生物及其制备方法和应用 |
| JP7128204B2 (ja) * | 2017-04-27 | 2022-08-30 | アストラゼネカ・アクチエボラーグ | Ｃ５－アニリノキナゾリン化合物及び癌の処置におけるそれらの使用 |
| WO2018197643A1 (en) | 2017-04-27 | 2018-11-01 | Astrazeneca Ab | Phenoxyquinazoline compounds and their use in treating cancer |
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- 2018-04-26 ES ES18721348T patent/ES2888298T3/es active Active
- 2018-04-26 RU RU2019136279A patent/RU2769694C2/ru active
- 2018-04-26 WO PCT/EP2018/060798 patent/WO2018197642A1/en not_active Ceased
- 2018-04-27 AR ARP180101102A patent/AR111494A1/es active IP Right Grant
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2019
- 2019-03-05 US US16/292,817 patent/US10829479B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7709479B1 (en) * | 1999-09-21 | 2010-05-04 | Astrazeneca | Quinazoline derivatives and their use as pharmaceuticals |
| US20060178382A1 (en) * | 2003-06-17 | 2006-08-10 | Astrazeneca Ab | Chinazoline derivatives as aurora kinase inhibitors |
| RU2434010C2 (ru) * | 2007-06-05 | 2011-11-20 | Ханми Фарм. Ко., Лтд. | Новое амидное производное для ингибирования роста раковых клеток |
Non-Patent Citations (1)
| Title |
|---|
| Rao, G.-W. и др.: Synthesis, Antitumor Evaluation and Docking Study of Novel 4-Anilinoquinazoline Derivatives as Potential Epidermal Growth Factor Receptor (EGFR) Inhibitors, ChemMedChem, 2013, 8(6), с.928-933. * |
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| CA3059283A1 (en) | 2018-11-01 |
| US20180312490A1 (en) | 2018-11-01 |
| MX389244B (es) | 2025-03-20 |
| CN110573505B (zh) | 2023-04-11 |
| BR112019022229A2 (pt) | 2020-05-12 |
| JP7128204B2 (ja) | 2022-08-30 |
| RU2019136279A (ru) | 2021-05-27 |
| RU2019136279A3 (https=) | 2021-05-31 |
| AR111494A1 (es) | 2019-07-17 |
| ES2888298T3 (es) | 2022-01-03 |
| AU2018259078A1 (en) | 2019-10-17 |
| JP2020517677A (ja) | 2020-06-18 |
| EP3615522A1 (en) | 2020-03-04 |
| TWI774758B (zh) | 2022-08-21 |
| EP3615522B1 (en) | 2021-08-04 |
| MX2019012847A (es) | 2022-01-07 |
| TW201904960A (zh) | 2019-02-01 |
| AU2018259078B2 (en) | 2021-10-07 |
| US20190263787A1 (en) | 2019-08-29 |
| US10273227B2 (en) | 2019-04-30 |
| WO2018197642A1 (en) | 2018-11-01 |
| US10829479B2 (en) | 2020-11-10 |
| KR20190141203A (ko) | 2019-12-23 |
| CN110573505A (zh) | 2019-12-13 |
| KR102603153B1 (ko) | 2023-11-15 |
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