JPWO2021093839A5 - - Google Patents
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- Publication number
- JPWO2021093839A5 JPWO2021093839A5 JP2022528124A JP2022528124A JPWO2021093839A5 JP WO2021093839 A5 JPWO2021093839 A5 JP WO2021093839A5 JP 2022528124 A JP2022528124 A JP 2022528124A JP 2022528124 A JP2022528124 A JP 2022528124A JP WO2021093839 A5 JPWO2021093839 A5 JP WO2021093839A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- pharmaceutically acceptable
- acceptable salt
- compound
- compound according
- 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 36
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- -1 phenoxy, 2-fluorophenoxy Chemical group 0.000 claims 2
- 239000003909 protein kinase inhibitor Substances 0.000 claims 2
- 125000005554 pyridyloxy group Chemical group 0.000 claims 2
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 241000699670 Mus sp. Species 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 5
- 229940079593 drug Drugs 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000233805 Phoenix Species 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- RVWUHFFPEOKYLB-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium Chemical compound CC1(C)CCCC(C)(C)[NH+]1[O-] RVWUHFFPEOKYLB-UHFFFAOYSA-N 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical compound C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 238000011579 SCID mouse model Methods 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 108010082117 matrigel Proteins 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911109773.2 | 2019-11-13 | ||
| CN201911109773 | 2019-11-13 | ||
| CN201911288492 | 2019-12-13 | ||
| CN201911288492.8 | 2019-12-13 | ||
| CN202010096582 | 2020-02-17 | ||
| CN202010096582.3 | 2020-02-17 | ||
| CN202010711270.9 | 2020-07-22 | ||
| CN202010711270 | 2020-07-22 | ||
| PCT/CN2020/128597 WO2021093839A1 (zh) | 2019-11-13 | 2020-11-13 | 作为btk抑制剂的吡咯并嘧啶类化合物及其应用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2023506691A JP2023506691A (ja) | 2023-02-20 |
| JPWO2021093839A5 true JPWO2021093839A5 (enrdf_load_html_response) | 2023-02-28 |
| JP7473642B2 JP7473642B2 (ja) | 2024-04-23 |
Family
ID=75912541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022528124A Active JP7473642B2 (ja) | 2019-11-13 | 2020-11-13 | Ｂｔｋ阻害剤としてのピロロピリミジン系化合物およびその使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US12378253B2 (enrdf_load_html_response) |
| EP (1) | EP4059935A4 (enrdf_load_html_response) |
| JP (1) | JP7473642B2 (enrdf_load_html_response) |
| KR (1) | KR102793446B1 (enrdf_load_html_response) |
| CN (2) | CN117551103A (enrdf_load_html_response) |
| WO (1) | WO2021093839A1 (enrdf_load_html_response) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20240002377A1 (en) * | 2020-12-07 | 2024-01-04 | Medshine Discovery Inc. | Pyrrolopyridine compound and application thereof |
| CN114761410B (zh) * | 2021-04-06 | 2023-08-25 | 广州必贝特医药股份有限公司 | 吡咯并嘧啶酮类化合物及其应用 |
| WO2022213932A1 (zh) * | 2021-04-06 | 2022-10-13 | 广州必贝特医药股份有限公司 | 吡咯并嘧啶酮类化合物及其应用 |
| KR20240004588A (ko) * | 2021-05-12 | 2024-01-11 | 제지앙 롱샴 바이오-테크 파르마. 씨오., 엘티디. | 피롤로피리미딘류 화합물의 결정형 및 이의 제조 방법 |
| JP2025500886A (ja) | 2021-12-14 | 2025-01-15 | クロスファイアー オンコロジー ホールディング ビー．ヴイ． | 大環状ｂｔｋ阻害剤 |
| CN115894500B (zh) * | 2022-11-02 | 2024-05-28 | 中国药科大学 | 一种作为btk激酶抑制剂的化合物及其制备方法与用途 |
| CN118702697A (zh) * | 2023-03-18 | 2024-09-27 | 山东新时代药业有限公司 | 苯甲酰基吡咯并嘧啶类衍生物及其用途和制备方法 |
| CN116375715B (zh) * | 2023-04-06 | 2025-04-04 | 中国药科大学 | 一种作为非共价btk激酶抑制剂的化合物及其生物用途 |
| WO2024246287A1 (en) | 2023-06-02 | 2024-12-05 | Crossfire Oncology Holding B.V. | Medical use of a macrocyclic reversible btk inhibitor |
| WO2024245577A1 (en) | 2023-06-02 | 2024-12-05 | Netherlands Translational Research Center Holding B.V. | Therapeutic combinations of an irreversible btk inhibitor and a reversible btk inhibitor |
| WO2024245578A1 (en) | 2023-06-02 | 2024-12-05 | Netherlands Translational Research Center Holding B.V. | Therapeutic combinations of an irreversible btk inhibitor and a macrocyclic reversible btk inhibitor |
| WO2024256568A1 (en) | 2023-06-13 | 2024-12-19 | Crossfire Oncology Holding B.V. | Salt and crystal forms of a macrocyclic btk inhibitor |
| WO2024256574A1 (en) | 2023-06-13 | 2024-12-19 | Crossfire Oncology Holding B.V. | Process for preparing macrocyclic btk inhibitors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI398252B (zh) * | 2006-05-26 | 2013-06-11 | Novartis Ag | 吡咯并嘧啶化合物及其用途 |
| NZ629807A (en) * | 2012-08-06 | 2017-04-28 | Acea Biosciences Inc | Novel pyrrolopyrimidine compounds as inhibitors of protein kinases |
| EP3042903B1 (en) * | 2015-01-06 | 2019-08-14 | Impetis Biosciences Ltd. | Substituted hetero-bicyclic compounds, compositions and medicinal applications thereof |
| MX384022B (es) | 2015-12-23 | 2025-03-14 | Arqule Inc | Tetrahidropiranil amino-pirrolopirimidinona y metodos de uso de la misma. |
| MX2019002212A (es) * | 2016-08-24 | 2019-07-08 | Arqule Inc | Compuestos de amino-pirrolo-pirimidinona y metodos de uso de los mismos. |
-
2020
- 2020-11-13 US US17/776,873 patent/US12378253B2/en active Active
- 2020-11-13 KR KR1020227018702A patent/KR102793446B1/ko active Active
- 2020-11-13 WO PCT/CN2020/128597 patent/WO2021093839A1/zh not_active Ceased
- 2020-11-13 CN CN202311079865.7A patent/CN117551103A/zh not_active Withdrawn
- 2020-11-13 EP EP20887944.5A patent/EP4059935A4/en active Pending
- 2020-11-13 JP JP2022528124A patent/JP7473642B2/ja active Active
- 2020-11-13 CN CN202080078768.4A patent/CN114728974B/zh active Active
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