JP2020510092A5 - - Google Patents
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- Publication number
- JP2020510092A5 JP2020510092A5 JP2019571789A JP2019571789A JP2020510092A5 JP 2020510092 A5 JP2020510092 A5 JP 2020510092A5 JP 2019571789 A JP2019571789 A JP 2019571789A JP 2019571789 A JP2019571789 A JP 2019571789A JP 2020510092 A5 JP2020510092 A5 JP 2020510092A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- propyl
- indole
- cycloalkyl
- pyrido
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims 56
- 150000001875 compounds Chemical class 0.000 claims 30
- 150000003839 salts Chemical class 0.000 claims 29
- 239000012453 solvate Substances 0.000 claims 28
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 26
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 24
- -1 = O Chemical class 0.000 claims 23
- 229910052736 halogen Inorganic materials 0.000 claims 23
- 150000002367 halogens Chemical class 0.000 claims 23
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 15
- 150000002431 hydrogen Chemical class 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 11
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 11
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 9
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
- 230000014509 gene expression Effects 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 102100034607 Protein arginine N-methyltransferase 5 Human genes 0.000 claims 2
- 101710084427 Protein arginine N-methyltransferase 5 Proteins 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000000338 in vitro Methods 0.000 claims 2
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 2
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 1
- IJXFUGSRMZWZTG-UHFFFAOYSA-N N-[2-hydroxy-3-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)propyl]-3,4-dihydro-1H-isoquinoline-2-carboxamide Chemical compound OC(CNC(=O)N1CC2=CC=CC=C2CC1)CN1CC=2NC3=CC=CC=C3C=2CC1 IJXFUGSRMZWZTG-UHFFFAOYSA-N 0.000 claims 1
- FDDDLKYUJOYUPP-UHFFFAOYSA-N N-[2-hydroxy-3-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)propyl]-3-phenylpiperidine-1-carboxamide Chemical compound OC(CNC(=O)N1CC(CCC1)C1=CC=CC=C1)CN1CC=2NC3=CC=CC=C3C=2CC1 FDDDLKYUJOYUPP-UHFFFAOYSA-N 0.000 claims 1
- VXTOIHWDEBRQSW-UHFFFAOYSA-N N-[2-hydroxy-3-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)propyl]-3-phenylpyrrolidine-1-carboxamide Chemical compound OC(CNC(=O)N1CCC(C1)C1=CC=CC=C1)CN1CCC2=C(C1)NC1=CC=CC=C21 VXTOIHWDEBRQSW-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- AUYNWRLEXAPZAJ-UHFFFAOYSA-N piperazine;trihydrochloride Chemical compound Cl.Cl.Cl.C1CNCCN1 AUYNWRLEXAPZAJ-UHFFFAOYSA-N 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 238000007614 solvation Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 *CC(CN(*)C(C1CCCCCCC1)=O)O Chemical compound *CC(CN(*)C(C1CCCCCCC1)=O)O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1704325.8A GB201704325D0 (en) | 2017-03-17 | 2017-03-17 | Compounds |
| GB1704325.8 | 2017-03-17 | ||
| PCT/EP2018/056675 WO2018167276A1 (en) | 2017-03-17 | 2018-03-16 | Tricyclic compounds for use in treatment of proliferative disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020510092A JP2020510092A (ja) | 2020-04-02 |
| JP2020510092A5 true JP2020510092A5 (enExample) | 2021-04-22 |
| JP7308765B2 JP7308765B2 (ja) | 2023-07-14 |
Family
ID=58688220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019571789A Active JP7308765B2 (ja) | 2017-03-17 | 2018-03-16 | 増殖性障害の治療に使用される三環式化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US11274098B2 (enExample) |
| EP (1) | EP3596073B1 (enExample) |
| JP (1) | JP7308765B2 (enExample) |
| KR (1) | KR102604942B1 (enExample) |
| CN (1) | CN110621675B (enExample) |
| CA (1) | CA3056726A1 (enExample) |
| ES (1) | ES2925115T3 (enExample) |
| GB (1) | GB201704325D0 (enExample) |
| WO (1) | WO2018167276A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201905780D0 (en) | 2019-04-25 | 2019-06-05 | La Thangue Nicholas | Cancer therapy |
| KR102282712B1 (ko) * | 2019-08-09 | 2021-07-27 | 한국화학연구원 | 신규한 피리미딘 설폰아마이드 유도체를 유효성분으로 포함하는 암 예방 또는 치료용 약학 조성물 |
| WO2021029450A1 (ko) * | 2019-08-09 | 2021-02-18 | 한국화학연구원 | 신규한 피리미딘 설폰아마이드 유도체 및 이를 유효성분으로 포함하는 암 예방 또는 치료용 약학 조성물 |
| KR102278691B1 (ko) * | 2019-08-09 | 2021-07-16 | 한국화학연구원 | 신규한 피리미딘 설폰아마이드 유도체 |
| WO2021066578A1 (ko) | 2019-10-02 | 2021-04-08 | 에스케이바이오팜 주식회사 | 바이사이클릭 화합물 및 이의 용도 |
| CN111454260B (zh) * | 2020-05-25 | 2023-02-28 | 贵州大学 | 一类含异丙醇胺亚结构的1，2，3，4-四氢-β-咔啉类化合物及其制备方法和应用 |
| CN111892593B (zh) * | 2020-08-19 | 2021-11-16 | 南通大学 | 一种8-甲氧基-5H-吡啶并[4,3-b]吲哚及其合成方法 |
| CN117062816A (zh) * | 2021-02-04 | 2023-11-14 | 美国安进公司 | 三环-酰胺-双环prmt5抑制剂 |
| CN113105517B (zh) * | 2021-04-10 | 2022-03-01 | 台州仙琚药业有限公司 | 雄甾-1,4,9-三烯-3,17-二酮的合成方法 |
| GB202108383D0 (en) * | 2021-06-11 | 2021-07-28 | Argonaut Therapeutics Ltd | Compounds useful in the treatment or prevention of a prmt5-mediated disorder |
| GB202117230D0 (en) | 2021-11-29 | 2022-01-12 | Argonaut Therapeutics Ltd | Peptide vaccine |
| GB202203588D0 (en) | 2022-03-15 | 2022-04-27 | Argonaut Therapeutics Ltd | Cancer diagnostic |
| CN115521306B (zh) * | 2022-09-26 | 2024-03-26 | 贵州大学 | 一种1,2,3,4-四氢-β-咔啉衍生物及其制备方法和应用 |
| CN117088891B (zh) * | 2023-07-13 | 2026-06-16 | 浙江大学 | 含四氢苯并[4,5]呋喃[2,3-c]吡啶类羟肟酸化合物及其制备方法和应用 |
| CN121226371B (zh) * | 2025-10-28 | 2026-07-14 | 百色学院 | 四氢吡嗪[1,2-a]吲哚类组蛋白去乙酰化酶抑制剂及其制备方法与应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3317524A (en) * | 1965-02-04 | 1967-05-02 | American Home Prod | Substituted 1, 2, 3, 4-tetrahydro-pyrazino[1, 2-a]indoles |
| US3687961A (en) * | 1971-05-03 | 1972-08-29 | Abbott Lab | 8-fluoro-2-{8 3-(4-fluorophenylanilinopropyl{9 -gamma-carboline |
| US4001263A (en) | 1974-04-01 | 1977-01-04 | Pfizer Inc. | 5-Aryl-1,2,3,4-tetrahydro-γ-carbolines |
| DE2854014A1 (de) * | 1978-12-14 | 1980-07-03 | Troponwerke Gmbh & Co Kg | 7,8,9,10-tetrahydrothieno eckige klammer auf 3,2-e eckige klammer zu pyrido eckige klammer auf 4,3-b eckige klammer zu indole, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4719211A (en) | 1984-05-01 | 1988-01-12 | American Home Products Corporation | 2,3,4,9-tetrahydro-2-heteroarylalkyl-1H-pyrido(3,4-B)indoles having antihypertensive properties |
| SU1248223A1 (ru) * | 1985-01-07 | 1995-09-20 | Научно-Исследовательский Институт По Биологическим Испытаниям Химических Соединений | ДИГИДРОХЛОРИД 2-(3-ИЗОПРОПИЛАМИНО-2-ГИДРОКСИПРОПИЛ)-1,2,3,4-ТЕТРАГИДРО- β -КАРБОЛИНА, ОБЛАДАЮЩИЙ АНТИАЛКОГОЛЬНЫМ И ПСИХОТРОПНЫМ ДЕЙСТВИЕМ |
| US4663456A (en) * | 1985-09-16 | 1987-05-05 | American Home Products Corporation | 2-(substituted piperazinylalkyl)β-carbolines useful in treatment of psychological disorders |
| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| CA2242425C (en) | 1996-02-13 | 2006-07-18 | Zeneca Limited | Quinazoline derivatives as vegf inhibitors |
| NZ331191A (en) | 1996-03-05 | 2000-03-27 | Zeneca Ltd | 4-anilinoquinazoline derivatives and pharmaceutical compositions thereof |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| UA52681C2 (uk) | 1997-04-08 | 2003-01-15 | Янссен Фармацевтика Н.В. | Похідні 1,2,3,4-тетрагідро-бензофуро[3,2,-c]піридину, спосіб їх одержання та фармацевтична композиція на їх основі |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| EP0905136A1 (en) | 1997-09-08 | 1999-03-31 | Janssen Pharmaceutica N.V. | Tetrahydro gamma-carbolines |
| GB9900334D0 (en) | 1999-01-07 | 1999-02-24 | Angiogene Pharm Ltd | Tricylic vascular damaging agents |
| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| EE05345B1 (et) | 1999-02-10 | 2010-10-15 | Astrazeneca Ab | Kinasoliini derivaadid angiogeneesi inhibiitoritena |
| BR0111230A (pt) | 2000-05-31 | 2003-06-10 | Astrazeneca Ab | Composto, e, uso e processo para a preparação do mesmo |
| UA73993C2 (uk) | 2000-06-06 | 2005-10-17 | Астразенека Аб | Хіназолінові похідні для лікування пухлин та фармацевтична композиція |
| KR20030014425A (ko) | 2000-07-07 | 2003-02-17 | 앤지오젠 파마슈티칼스 리미티드 | 혈관 손상제인 콜치놀 유도체 |
| EE200300015A (et) | 2000-07-07 | 2004-10-15 | Angiogene Pharmaceuticals Limited | Kolhinooli derivaadid kui angiogeneesi inhibiitorid |
| AUPR201600A0 (en) | 2000-12-11 | 2001-01-11 | Fujisawa Pharmaceutical Co., Ltd. | Quinazolinone derivative |
| NZ555491A (en) | 2005-01-03 | 2010-01-29 | Univ Siena | Aryl piperazine derivatives for the treatment of neuropsychiatric disorders |
| US20070213359A1 (en) | 2005-12-30 | 2007-09-13 | Acadia Pharmaceuticals Inc. | Bicyclic-nitrogen compounds as modulators of ghrelin receptor and uses thereof |
| US8853391B2 (en) | 2008-12-18 | 2014-10-07 | Merck Patent Gmbh | Tricyclic azaindoles |
| JP2016505002A (ja) * | 2012-12-21 | 2016-02-18 | エピザイム，インコーポレイティド | ジヒドロイソキノリンまたはテトラヒドロイソキノリンを含有するｐｒｍｔ５阻害剤およびその使用 |
| AU2014205065A1 (en) | 2013-01-14 | 2015-07-30 | Ent Associates Of Los Alamos, Llc | Honey nasal rinse |
| US9879015B2 (en) | 2013-04-23 | 2018-01-30 | Laboratorios Del Dr. Esteve S.A. | Pyrazino[1,2-a]indole compounds, their preparation and use in medicaments |
| JP6388456B2 (ja) | 2013-06-28 | 2018-09-12 | アルツプロテクト | 神経変性疾患の治療に使用可能なカルボリン化合物 |
| US10662193B2 (en) * | 2014-01-21 | 2020-05-26 | Ac Immune Sa | Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyloid-like proteins |
| US20170107229A1 (en) | 2014-05-26 | 2017-04-20 | Bayer Pharma Aktiengesellschaft | Substituted tetrahydropyridothienopyrimidines |
| EP3160466A4 (en) * | 2014-06-25 | 2017-12-27 | Epizyme, Inc. | Prmt5 inhibitors and uses thereof |
| AU2015301196A1 (en) * | 2014-08-04 | 2017-01-12 | Epizyme, Inc. | PRMT5 inhibitors and uses thereof |
-
2017
- 2017-03-17 GB GBGB1704325.8A patent/GB201704325D0/en not_active Ceased
-
2018
- 2018-03-16 CN CN201880031972.3A patent/CN110621675B/zh active Active
- 2018-03-16 EP EP18711927.6A patent/EP3596073B1/en active Active
- 2018-03-16 ES ES18711927T patent/ES2925115T3/es active Active
- 2018-03-16 JP JP2019571789A patent/JP7308765B2/ja active Active
- 2018-03-16 CA CA3056726A patent/CA3056726A1/en active Pending
- 2018-03-16 WO PCT/EP2018/056675 patent/WO2018167276A1/en not_active Ceased
- 2018-03-16 US US16/494,570 patent/US11274098B2/en active Active
- 2018-03-16 KR KR1020197029438A patent/KR102604942B1/ko active Active
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