JPWO2019231942A5 - - Google Patents
Download PDFInfo
- Publication number
- JPWO2019231942A5 JPWO2019231942A5 JP2020566880A JP2020566880A JPWO2019231942A5 JP WO2019231942 A5 JPWO2019231942 A5 JP WO2019231942A5 JP 2020566880 A JP2020566880 A JP 2020566880A JP 2020566880 A JP2020566880 A JP 2020566880A JP WO2019231942 A5 JPWO2019231942 A5 JP WO2019231942A5
- Authority
- JP
- Japan
- Prior art keywords
- oxy
- methoxy
- quinoline
- morpholinopropoxy
- pyridin
- 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.)
- Pending
Links
- -1 5-((6-Methoxy-7- (3-morpholinopropoxy) quinoline-4-yl) oxy) pyridin-2-yl Chemical group 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 108091005706 TAM receptors Proteins 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 150000001204 N-oxides Chemical class 0.000 claims description 12
- 239000000651 prodrug Substances 0.000 claims description 12
- 229940002612 prodrugs Drugs 0.000 claims description 12
- FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000011780 sodium chloride Substances 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- DZJOBCWAEADIGO-UHFFFAOYSA-N COC=1C=C2C(=CC=NC2=CC=1OCCCN1CCOCC1)OC=1C=CC(=NC=1)NC(=O)C=1N=C(C2=C(N=1)C1CCN2CC1)C1=CC=CC=C1 Chemical compound COC=1C=C2C(=CC=NC2=CC=1OCCCN1CCOCC1)OC=1C=CC(=NC=1)NC(=O)C=1N=C(C2=C(N=1)C1CCN2CC1)C1=CC=CC=C1 DZJOBCWAEADIGO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 108020003175 receptors Proteins 0.000 claims description 8
- KEOWESKYLZPQEQ-UHFFFAOYSA-N C1CN(CCO1)CCCOC1=C(OC)C=C2C(OC3=CC=C(NC(=O)C4=NC5=C(C(=O)N4)C=CC=C5)N=C3)=CC=NC2=C1 Chemical compound C1CN(CCO1)CCCOC1=C(OC)C=C2C(OC3=CC=C(NC(=O)C4=NC5=C(C(=O)N4)C=CC=C5)N=C3)=CC=NC2=C1 KEOWESKYLZPQEQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atoms Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- WZFOPYGRZNUWSP-UHFFFAOYSA-N 7-oxa-2-azaspiro[3.5]nonane Chemical compound C1NCC11CCOCC1 WZFOPYGRZNUWSP-UHFFFAOYSA-N 0.000 claims description 4
- 206010000880 Acute myeloid leukaemia Diseases 0.000 claims description 4
- PKVMNIRVLVYOCI-UHFFFAOYSA-N C1CN(CCO1)CCCOC1=C(OC)C=C2C(OC3=CC=C(NC(=O)C4=NC(C5=CC=CC=C5)=CC=N4)N=C3)=CC=NC2=C1 Chemical compound C1CN(CCO1)CCCOC1=C(OC)C=C2C(OC3=CC=C(NC(=O)C4=NC(C5=CC=CC=C5)=CC=N4)N=C3)=CC=NC2=C1 PKVMNIRVLVYOCI-UHFFFAOYSA-N 0.000 claims description 4
- QRLRQIGXLZRZJK-UHFFFAOYSA-N COC=1C=C2C(=CC=NC2=CC=1OCCCN1CCCCC1)OC=1C=CC(=NC=1)NC(=O)C=1N=C(C2=C(N=1)C1CCN2CC1)C1=CC=CC=C1 Chemical compound COC=1C=C2C(=CC=NC2=CC=1OCCCN1CCCCC1)OC=1C=CC(=NC=1)NC(=O)C=1N=C(C2=C(N=1)C1CCN2CC1)C1=CC=CC=C1 QRLRQIGXLZRZJK-UHFFFAOYSA-N 0.000 claims description 4
- PBZONRVVNZJFHD-UHFFFAOYSA-N COC=1C=C2C(=CC=NC2=CC=1OCCCN1CCOCC1)OC=1C=CC(=NC=1)NC(=O)C1=NC2=CC=CC=C2C(=N1)C1=CC=CC=C1 Chemical compound COC=1C=C2C(=CC=NC2=CC=1OCCCN1CCOCC1)OC=1C=CC(=NC=1)NC(=O)C1=NC2=CC=CC=C2C(=N1)C1=CC=CC=C1 PBZONRVVNZJFHD-UHFFFAOYSA-N 0.000 claims description 4
- LOWLZSQVOBUWAV-UHFFFAOYSA-N COC=1C=C2C(=CC=NC2=CC=1OCCCN1CCOCC1)OC=1C=CC(=NC=1)NC(=O)C=1N=C(SC=1)C1=CC=CC=C1 Chemical compound COC=1C=C2C(=CC=NC2=CC=1OCCCN1CCOCC1)OC=1C=CC(=NC=1)NC(=O)C=1N=C(SC=1)C1=CC=CC=C1 LOWLZSQVOBUWAV-UHFFFAOYSA-N 0.000 claims description 4
- IMAONOMSGPEQBJ-UHFFFAOYSA-N FC=1C=C(C=CC=1OC1=CC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)NC(=O)C=1N=C(C2=C(N=1)C1CCN2CC1)C1=CC=CC=C1 Chemical compound FC=1C=C(C=CC=1OC1=CC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)NC(=O)C=1N=C(C2=C(N=1)C1CCN2CC1)C1=CC=CC=C1 IMAONOMSGPEQBJ-UHFFFAOYSA-N 0.000 claims description 4
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims description 4
- WFIPGJAUNMRIRT-UHFFFAOYSA-N O1CCN(CC1)CCCOC1=C(OC)C=C2C(OC3=CC=C(NC(=O)C4=NC(C5=CC=CC=C5)=CC=C4)N=C3)=CC=NC2=C1 Chemical compound O1CCN(CC1)CCCOC1=C(OC)C=C2C(OC3=CC=C(NC(=O)C4=NC(C5=CC=CC=C5)=CC=C4)N=C3)=CC=NC2=C1 WFIPGJAUNMRIRT-UHFFFAOYSA-N 0.000 claims description 4
- 101710013725 TYR Proteins 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 4
- 125000004434 sulfur atoms Chemical group 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 230000001404 mediated Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- NAZVZHAVXBADJW-UHFFFAOYSA-N C1CN(CCO1)CCCOC1=C(OC)C=C2C(OC3=CC=C(NC(=O)C4=CC(C5=CC=CC=C5)=CC=N4)N=C3)=CC=NC2=C1 Chemical compound C1CN(CCO1)CCCOC1=C(OC)C=C2C(OC3=CC=C(NC(=O)C4=CC(C5=CC=CC=C5)=CC=N4)N=C3)=CC=NC2=C1 NAZVZHAVXBADJW-UHFFFAOYSA-N 0.000 claims description 2
- POVPUENWCUYAEZ-UHFFFAOYSA-N C1CN(CCO1)CCCOC1=C(OC)C=C2C(OC3=CC=C(NC(=O)C4=NC=CC(=C4)C)N=C3)=CC=NC2=C1 Chemical compound C1CN(CCO1)CCCOC1=C(OC)C=C2C(OC3=CC=C(NC(=O)C4=NC=CC(=C4)C)N=C3)=CC=NC2=C1 POVPUENWCUYAEZ-UHFFFAOYSA-N 0.000 claims description 2
- KHTOJAONINORAG-UHFFFAOYSA-N COC=1C=C2C(=CC=NC2=CC=1OCCCN1CCOCC1)OC=1C=CC(=NC=1)NC(=O)C=1SC(=CN=1)C1=CC=CC=C1 Chemical compound COC=1C=C2C(=CC=NC2=CC=1OCCCN1CCOCC1)OC=1C=CC(=NC=1)NC(=O)C=1SC(=CN=1)C1=CC=CC=C1 KHTOJAONINORAG-UHFFFAOYSA-N 0.000 claims description 2
- 208000007046 Leukemia, Myeloid, Acute Diseases 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutic aid Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 239000003814 drug Substances 0.000 description 2
- HPJALMWOZYIZGE-UHFFFAOYSA-N 2-oxa-6-azaspiro[3.3]heptane Chemical compound C1NCC11COC1 HPJALMWOZYIZGE-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862679095P | 2018-06-01 | 2018-06-01 | |
| US62/679,095 | 2018-06-01 | ||
| PCT/US2019/034239 WO2019231942A1 (en) | 2018-06-01 | 2019-05-29 | Quinoline derivatives useful as tyrosine kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2021525755A JP2021525755A (ja) | 2021-09-27 |
| JPWO2019231942A5 true JPWO2019231942A5 (de) | 2022-06-02 |
Family
ID=67003644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020566880A Pending JP2021525755A (ja) | 2018-06-01 | 2019-05-29 | チロシンキナーゼ阻害剤として有用なキノリン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US10851093B2 (de) |
| EP (1) | EP3810596B1 (de) |
| JP (1) | JP2021525755A (de) |
| CN (1) | CN112513030A (de) |
| CA (1) | CA3101983A1 (de) |
| ES (1) | ES2939358T3 (de) |
| WO (1) | WO2019231942A1 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117362275A (zh) * | 2022-06-29 | 2024-01-09 | 广州百霆医药科技有限公司 | 一种酪氨酸蛋白激酶抑制剂及其用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080004273A1 (en) * | 2006-05-30 | 2008-01-03 | Stephane Raeppel | Inhibitors of protein tyrosine kinase activity |
| EP2032538A2 (de) * | 2006-06-08 | 2009-03-11 | Array Biopharma, Inc. | Chinolinverbindungen und anwendungsverfahren dafür |
| EP2423208A1 (de) * | 2010-08-28 | 2012-02-29 | Lead Discovery Center GmbH | Pharmazeutisch aktive Zusammensetzungen als Axl-Hemmer |
| US9133162B2 (en) * | 2011-02-28 | 2015-09-15 | Sunshine Lake Pharma Co., Ltd. | Substituted quinoline compounds and methods of use |
| ES2614824T3 (es) * | 2011-11-14 | 2017-06-02 | Ignyta, Inc. | Derivados de uracil como inhibidores de la quinasa axl y c-met |
| CN103965107B (zh) * | 2013-02-06 | 2016-08-17 | 沈阳药科大学 | 2-芳基取代喹啉类化合物及其用途 |
| CN104072480B (zh) * | 2013-03-27 | 2016-12-28 | 沈阳药科大学 | 喹啉类化合物及其制备方法和应用 |
| TWI649308B (zh) * | 2013-07-24 | 2019-02-01 | 小野藥品工業股份有限公司 | 喹啉衍生物 |
| JP6708130B2 (ja) * | 2014-12-25 | 2020-06-10 | 小野薬品工業株式会社 | キノリン誘導体 |
-
2019
- 2019-05-29 CN CN201980049584.2A patent/CN112513030A/zh active Pending
- 2019-05-29 CA CA3101983A patent/CA3101983A1/en active Pending
- 2019-05-29 EP EP19733230.7A patent/EP3810596B1/de active Active
- 2019-05-29 ES ES19733230T patent/ES2939358T3/es active Active
- 2019-05-29 JP JP2020566880A patent/JP2021525755A/ja active Pending
- 2019-05-29 US US16/424,619 patent/US10851093B2/en active Active
- 2019-05-29 WO PCT/US2019/034239 patent/WO2019231942A1/en unknown
-
2020
- 2020-11-25 US US17/105,334 patent/US20210078990A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7058345B2 (ja) | Ｂｃｌ－２阻害剤及びＭＤＭ２阻害剤の組合せ製品並びに疾患の予防及び／又治療におけるその使用 | |
| KR102122244B1 (ko) | 설파모일-아릴아미드 및 b형 간염 치료제로서의 그 용도 | |
| JP6013375B2 (ja) | キナーゼ阻害剤としてのチアゾリルフェニル−ベンゼンスルホンアミド誘導体 | |
| JP2019527731A (ja) | Ｈｂｖ感染の治療のための新規治療薬 | |
| CA3093851A1 (en) | Substituted 1,1'-biphenyl compounds, analogues thereof, and methods using same | |
| AU2020286339B2 (en) | Compositions and methods for inhibiting kinases | |
| JP2019505595A5 (de) | ||
| JP2009529047A5 (de) | ||
| KR100764330B1 (ko) | 급성 및/또는 만성 신경학적 장애의 치료를 위한ｍＧｌｕＲ2 길항제 및 ＡＣｈＥ 억제제의 조합물 | |
| JP7330546B2 (ja) | 癌細胞の成長を抑制するピリミジン誘導体およびその医薬用途 | |
| CN101622229A (zh) | 具有脲基和氨基羰基作为取代基的新型吡咯衍生物 | |
| JP2010527984A5 (de) | ||
| JP2010527985A5 (de) | ||
| KR20190129034A (ko) | 금속효소 억제제 화합물 | |
| WO2022083657A1 (zh) | 取代苯并或吡啶并嘧啶胺类抑制剂及其制备方法和应用 | |
| TW201831469A (zh) | 金屬酶抑制劑化合物、醫藥組成物及使用該化合物和該組成物的方法 | |
| JPWO2019231942A5 (de) | ||
| WO2022171018A1 (zh) | 取代苯并或吡啶并嘧啶胺类抑制剂及其制备方法和应用 | |
| JP7065898B2 (ja) | 新規化合物、その調製およびその治療的使用 | |
| US20240010641A1 (en) | N-Linked Glycosylation Inhibitors and Methods of Using Same | |
| WO2021141538A1 (en) | Combination therapy | |
| JP2017507183A5 (de) | ||
| CN117357650A (zh) | 包含sos1抑制剂的药物组合物 |