JP2020517677A5 - - Google Patents
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- Publication number
- JP2020517677A5 JP2020517677A5 JP2019557764A JP2019557764A JP2020517677A5 JP 2020517677 A5 JP2020517677 A5 JP 2020517677A5 JP 2019557764 A JP2019557764 A JP 2019557764A JP 2019557764 A JP2019557764 A JP 2019557764A JP 2020517677 A5 JP2020517677 A5 JP 2020517677A5
- Authority
- JP
- Japan
- Prior art keywords
- triazole
- acetamide
- amino
- phenyl
- compound
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 46
- -1 5,7-dimethoxyquinazoline-4-yl Chemical group 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 10
- 230000005855 radiation Effects 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- IXWMDZDYMSJYQR-UHFFFAOYSA-N COC1=C(C=NC=N2)C2=CC(OC2COCC2)=C1 Chemical compound COC1=C(C=NC=N2)C2=CC(OC2COCC2)=C1 IXWMDZDYMSJYQR-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- VMWJUQZGLCWWDV-UHFFFAOYSA-N acetamide;4-methylbenzenesulfonic acid Chemical compound CC(N)=O.CC1=CC=C(S(O)(=O)=O)C=C1 VMWJUQZGLCWWDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IIUNKDCOPLGITA-UHFFFAOYSA-N 4-N-(5,7-dimethoxyquinazolin-4-yl)benzene-1,4-diamine Chemical compound COc1cc(OC)c2c(Nc3ccc(N)cc3)ncnc2c1 IIUNKDCOPLGITA-UHFFFAOYSA-N 0.000 description 1
- AMCMSZVLSWCVQX-UHFFFAOYSA-N 5,7-dimethoxy-1h-quinazolin-4-one Chemical compound N1C=NC(=O)C=2C1=CC(OC)=CC=2OC AMCMSZVLSWCVQX-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762490859P | 2017-04-27 | 2017-04-27 | |
| US62/490,859 | 2017-04-27 | ||
| PCT/EP2018/060798 WO2018197642A1 (en) | 2017-04-27 | 2018-04-26 | C5-anilinoquinazoline compounds and their use in treating cancer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020517677A JP2020517677A (ja) | 2020-06-18 |
| JP2020517677A5 true JP2020517677A5 (enExample) | 2021-04-22 |
| JP7128204B2 JP7128204B2 (ja) | 2022-08-30 |
Family
ID=62091877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019557764A Active JP7128204B2 (ja) | 2017-04-27 | 2018-04-26 | 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 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US10273227B2 (enExample) |
| EP (1) | EP3615522B1 (enExample) |
| JP (1) | JP7128204B2 (enExample) |
| KR (1) | KR102603153B1 (enExample) |
| CN (1) | CN110573505B (enExample) |
| AR (1) | AR111494A1 (enExample) |
| AU (1) | AU2018259078B2 (enExample) |
| CA (1) | CA3059283A1 (enExample) |
| ES (1) | ES2888298T3 (enExample) |
| MX (1) | MX389244B (enExample) |
| RU (1) | RU2769694C2 (enExample) |
| TW (1) | TWI774758B (enExample) |
| WO (1) | WO2018197642A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2018259078B2 (en) * | 2017-04-27 | 2021-10-07 | Astrazeneca Ab | C5-anilinoquinazoline compounds and their use in treating cancer |
| US20210380685A1 (en) * | 2018-10-18 | 2021-12-09 | Sinomab Bioscience Limited | Methods of Treating Rheumatoid Arthritis |
| AR117788A1 (es) * | 2019-01-14 | 2021-08-25 | Pi Industries Ltd | Compuestos de fenilamidina 3-sustituida, preparación y uso |
| KR20230008775A (ko) | 2020-05-08 | 2023-01-16 | 젠맵 에이/에스 | Cd3 및 cd20에 대한 이중특이적 항체 |
| US20240034788A1 (en) * | 2020-08-20 | 2024-02-01 | The Board Of Trustees Of The Leland Stanford Junior University | Abscopal therapy for cancer |
| WO2022053657A1 (en) | 2020-09-10 | 2022-03-17 | Genmab A/S | Bispecific antibody against cd3 and cd20 in combination therapy for treating diffuse large b-cell lymphoma |
| CN116437956A (zh) | 2020-09-10 | 2023-07-14 | 健玛保 | 用于治疗慢性淋巴细胞白血病的针对cd3和cd20的双特异性抗体 |
| JP2023542290A (ja) | 2020-09-10 | 2023-10-06 | ジェンマブ エー／エス | 濾胞性リンパ腫を治療するための併用療法におけるｃｄ３及びｃｄ２０に対する二重特異性抗体 |
| WO2022053654A1 (en) | 2020-09-10 | 2022-03-17 | Genmab A/S | Bispecific antibody against cd3 and cd20 in combination therapy for treating diffuse large b-cell lymphoma |
| IL301086A (en) | 2020-09-10 | 2023-05-01 | Genmab As | Bispecific antibody against cd3 and cd20 in combination therapy for treating follicular lymphoma |
| KR20230064560A (ko) * | 2021-10-29 | 2023-05-10 | 보로노이바이오 주식회사 | 퀴나졸린 유도체 화합물 및 이의 용도 |
| MX2024007044A (es) * | 2021-12-09 | 2024-09-04 | Deciphera Pharmaceuticals Llc | Compuestos heterociclicos como inhibidores de kit quinasa. |
| US20250275978A1 (en) * | 2024-03-04 | 2025-09-04 | Cardiff Oncology, Inc. | Use of onvansertib as monotherapy and in combination with cetuximab in treating ras wild-type colorectal cancer |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9510757D0 (en) | 1994-09-19 | 1995-07-19 | Wellcome Found | Therapeuticaly active compounds |
| GB9514265D0 (en) | 1995-07-13 | 1995-09-13 | Wellcome Found | Hetrocyclic compounds |
| EE200200119A (et) | 1999-09-21 | 2003-04-15 | Astrazeneca Ab | Kinasoliini derivaadid ja nende kasutamine ravimitena |
| EP1382604B1 (en) | 2001-04-27 | 2005-12-28 | Kirin Beer Kabushiki Kaisha | Quinoline derivative having azolyl group and quinazoline derivative |
| TW200505452A (en) | 2003-06-17 | 2005-02-16 | Astrazeneca Ab | Chemical compounds |
| WO2005048953A2 (en) * | 2003-11-13 | 2005-06-02 | Ambit Biosciences Corporation | Amide derivatives as kinase modulators |
| MX2007004403A (es) | 2004-10-12 | 2007-04-27 | Astrazeneca Ab | Derivados de quinazolina. |
| 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 |
| US20080200458A1 (en) | 2007-01-18 | 2008-08-21 | Joseph Barbosa | Methods and compositions for the treatment of body composition disorders |
| WO2008089307A2 (en) | 2007-01-18 | 2008-07-24 | Lexicon Pharmaceuticals, Inc. | Delta 5 desaturase inhibitors for the treatment of pain, inflammation and cancer |
| TWI377944B (en) * | 2007-06-05 | 2012-12-01 | Hanmi Holdings Co Ltd | Novel amide derivative for inhibiting the growth of cancer cells |
| WO2009140549A1 (en) | 2008-05-14 | 2009-11-19 | 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 |
| CN102918029B (zh) * | 2011-05-17 | 2015-06-17 | 江苏康缘药业股份有限公司 | 4-苯胺-6-丁烯酰胺-7-烷醚喹唑啉衍生物及其制备方法和用途 |
| 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 |
| AU2018259078B2 (en) * | 2017-04-27 | 2021-10-07 | Astrazeneca Ab | C5-anilinoquinazoline compounds and their use in treating cancer |
| US11053223B2 (en) | 2017-04-27 | 2021-07-06 | Astrazeneca Ab | Phenoxyquinazoline compounds and their use in treating cancer |
-
2018
- 2018-04-26 AU AU2018259078A patent/AU2018259078B2/en active Active
- 2018-04-26 ES ES18721348T patent/ES2888298T3/es active Active
- 2018-04-26 JP JP2019557764A patent/JP7128204B2/ja active Active
- 2018-04-26 MX MX2019012847A patent/MX389244B/es unknown
- 2018-04-26 EP EP18721348.3A patent/EP3615522B1/en active Active
- 2018-04-26 TW TW107114297A patent/TWI774758B/zh active
- 2018-04-26 CA CA3059283A patent/CA3059283A1/en active Pending
- 2018-04-26 WO PCT/EP2018/060798 patent/WO2018197642A1/en not_active Ceased
- 2018-04-26 US US15/963,122 patent/US10273227B2/en active Active
- 2018-04-26 RU RU2019136279A patent/RU2769694C2/ru active
- 2018-04-26 KR KR1020197034070A patent/KR102603153B1/ko active Active
- 2018-04-26 CN CN201880027620.0A patent/CN110573505B/zh active Active
- 2018-04-27 AR ARP180101102A patent/AR111494A1/es active IP Right Grant
-
2019
- 2019-03-05 US US16/292,817 patent/US10829479B2/en active Active
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