JP2021512055A5 - - Google Patents
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- JP2021512055A5 JP2021512055A5 JP2020539206A JP2020539206A JP2021512055A5 JP 2021512055 A5 JP2021512055 A5 JP 2021512055A5 JP 2020539206 A JP2020539206 A JP 2020539206A JP 2020539206 A JP2020539206 A JP 2020539206A JP 2021512055 A5 JP2021512055 A5 JP 2021512055A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- alkoxy
- membered
- optionally substituted
- 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 30
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 175
- 125000001424 substituent group Chemical group 0.000 claims 151
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 124
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 99
- 229910005965 SO 2 Inorganic materials 0.000 claims 93
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 79
- 125000000623 heterocyclic group Chemical group 0.000 claims 63
- 125000003545 alkoxy group Chemical group 0.000 claims 59
- 229910052739 hydrogen Inorganic materials 0.000 claims 58
- 239000001257 hydrogen Substances 0.000 claims 58
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims 42
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 40
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 37
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 37
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 35
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims 33
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 229910052736 halogen Inorganic materials 0.000 claims 32
- 150000002367 halogens Chemical group 0.000 claims 32
- 125000001072 heteroaryl group Chemical group 0.000 claims 27
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 27
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims 24
- 125000005843 halogen group Chemical group 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 24
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 20
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 18
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 18
- 150000002148 esters Chemical class 0.000 claims 16
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 15
- OHOQEZWSNFNUSY-UHFFFAOYSA-N Cy3-bifunctional dye zwitterion Chemical compound O=C1CCC(=O)N1OC(=O)CCCCCN1C2=CC=C(S(O)(=O)=O)C=C2C(C)(C)C1=CC=CC(C(C1=CC(=CC=C11)S([O-])(=O)=O)(C)C)=[N+]1CCCCCC(=O)ON1C(=O)CCC1=O OHOQEZWSNFNUSY-UHFFFAOYSA-N 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000004122 cyclic group Chemical group 0.000 claims 12
- 229940079593 drug Drugs 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Chemical group 0.000 claims 7
- 239000011737 fluorine Chemical group 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 125000004429 atom Chemical group 0.000 claims 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 5
- 108091077436 Tam family Proteins 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 5
- 108020003175 receptors Proteins 0.000 claims 5
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 4
- 239000003446 ligand Substances 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- -1 oxacyclopropyl group Chemical group 0.000 claims 4
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 3
- 230000002159 abnormal effect Effects 0.000 claims 3
- 125000006193 alkinyl group Chemical group 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 3
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 230000014509 gene expression Effects 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
- 201000009273 Endometriosis Diseases 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 101000916644 Homo sapiens Macrophage colony-stimulating factor 1 receptor Proteins 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 208000024248 Vascular System injury Diseases 0.000 claims 2
- 208000012339 Vascular injury Diseases 0.000 claims 2
- 206010047571 Visual impairment Diseases 0.000 claims 2
- 239000012190 activator Substances 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000033 alkoxyamino group Chemical group 0.000 claims 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000036039 immunity Effects 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 230000003902 lesion Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 208000019553 vascular disease Diseases 0.000 claims 2
- 208000029257 vision disease Diseases 0.000 claims 2
- 230000004393 visual impairment Effects 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical group C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 1
- QMDFJHAAWUGVKQ-UHFFFAOYSA-N 2h-thiopyran Chemical group C1SC=CC=C1 QMDFJHAAWUGVKQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 1
- 108091008036 Immune checkpoint proteins Proteins 0.000 claims 1
- 102000037982 Immune checkpoint proteins Human genes 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 108700025716 Tumor Suppressor Genes Proteins 0.000 claims 1
- 102000044209 Tumor Suppressor Genes Human genes 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 229940022399 cancer vaccine Drugs 0.000 claims 1
- 238000009566 cancer vaccine Methods 0.000 claims 1
- 238000002659 cell therapy Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003102 growth factor Substances 0.000 claims 1
- 229940125697 hormonal agent Drugs 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 238000009169 immunotherapy Methods 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000002018 overexpression Effects 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 229940126586 small molecule drug Drugs 0.000 claims 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 claims 1
- 0 C*1COCC1 Chemical compound C*1COCC1 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000001262 western blot Methods 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N C1CCSCC1 Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N CC1COCC1 Chemical compound CC1COCC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810043348.7 | 2018-01-17 | ||
| CN201810043348 | 2018-01-17 | ||
| CN201810891111 | 2018-08-07 | ||
| CN201810891111.4 | 2018-08-07 | ||
| CN201811354582.8 | 2018-11-14 | ||
| CN201811354582 | 2018-11-14 | ||
| PCT/CN2019/072083 WO2019141202A1 (zh) | 2018-01-17 | 2019-01-17 | Tam家族激酶/和csf1r激酶抑制剂及其用途 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021512055A JP2021512055A (ja) | 2021-05-13 |
| JP2021512055A5 true JP2021512055A5 (enExample) | 2021-12-02 |
| JP7282397B2 JP7282397B2 (ja) | 2023-05-29 |
Family
ID=67274177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020539206A Active JP7282397B2 (ja) | 2018-01-17 | 2019-01-17 | Ｔａｍファミリーキナーゼ／及びｃｓｆ１ｒキナーゼ阻害剤及びその用途 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20210177828A1 (enExample) |
| EP (1) | EP3741752A4 (enExample) |
| JP (1) | JP7282397B2 (enExample) |
| CN (1) | CN110041316B (enExample) |
| WO (1) | WO2019141202A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113302188A (zh) * | 2019-01-03 | 2021-08-24 | 阵列生物制药公司 | 作为tam及met激酶抑制剂的喹啉化合物 |
| US12479850B2 (en) * | 2019-09-06 | 2025-11-25 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Compound having Axl and c-Met kinase inhibitory activity, preparation thereof and application thereof |
| EP4036086A1 (en) * | 2019-09-24 | 2022-08-03 | Transthera Sciences (Nanjing), Inc. | Heterocyclic derivative and use thereof |
| CN112625026B (zh) * | 2019-09-24 | 2022-09-09 | 药捷安康(南京)科技股份有限公司 | Tam家族激酶抑制剂的喹啉衍生物 |
| JP2022551422A (ja) * | 2019-09-26 | 2022-12-09 | エグゼリクシス， インコーポレイテッド | ピリドン化合物およびタンパク質キナーゼの調節における使用の方法 |
| PE20230823A1 (es) * | 2020-03-30 | 2023-05-19 | Hutchison Medipharma Ltd | Compuestos de amida y usos de los mismos |
| WO2022266236A1 (en) | 2021-06-18 | 2022-12-22 | Aligos Therapeutics, Inc. | Methods and compositions for targeting pd-l1 |
| JPWO2023286719A1 (enExample) * | 2021-07-13 | 2023-01-19 | ||
| US12428427B2 (en) | 2021-12-16 | 2025-09-30 | Aligos Therapeutics, Inc. | Methods and compositions for targeting PD-L1 |
| CN115894198B (zh) * | 2022-11-04 | 2024-05-17 | 浙江永太科技股份有限公司 | Qulipta的关键中间体1-(2,3,6-三氟苯基)丙烷-2-酮的制备方法 |
| CN116751162B (zh) * | 2023-06-28 | 2025-02-28 | 中国人民解放军军事科学院军事医学研究院 | 一种喹啉类化合物、其制备方法、药物组合物及医药用途 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO2787B1 (en) * | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| TWI365185B (en) * | 2008-07-24 | 2012-06-01 | Lilly Co Eli | Amidophenoxyindazoles useful as inhibitors of c-met |
| DK2780338T3 (en) * | 2011-11-14 | 2016-12-19 | Ignyta Inc | Uracil AS AXL- AND C-MET kinase inhibitors |
| TWI723572B (zh) * | 2014-07-07 | 2021-04-01 | 日商第一三共股份有限公司 | 具有四氫吡喃基甲基之吡啶酮衍生物及其用途 |
| CN106467541B (zh) * | 2015-08-18 | 2019-04-05 | 暨南大学 | 取代喹诺酮类衍生物或其药学上可接受的盐或立体异构体及其药用组合物和应用 |
| CN107151240A (zh) * | 2016-03-04 | 2017-09-12 | 中国科学院上海药物研究所 | 一类多取代喹诺酮类化合物及其制备方法和用途 |
| EP3436461B1 (en) * | 2016-03-28 | 2023-11-01 | Incyte Corporation | Pyrrolotriazine compounds as tam inhibitors |
| CN108250200A (zh) * | 2016-12-28 | 2018-07-06 | 中国科学院上海药物研究所 | 一种具有Axl抑制活性的化合物及其制备和应用 |
-
2019
- 2019-01-17 US US15/733,382 patent/US20210177828A1/en not_active Abandoned
- 2019-01-17 JP JP2020539206A patent/JP7282397B2/ja active Active
- 2019-01-17 WO PCT/CN2019/072083 patent/WO2019141202A1/zh not_active Ceased
- 2019-01-17 CN CN201910046133.5A patent/CN110041316B/zh active Active
- 2019-01-17 EP EP19741754.6A patent/EP3741752A4/en not_active Withdrawn
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