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 |
|---|---|---|---|
| GB1704325.8 | 2017-03-17 | ||
| GBGB1704325.8A GB201704325D0 (en) | 2017-03-17 | 2017-03-17 | Compounds |
| 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 (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201905780D0 (en) | 2019-04-25 | 2019-06-05 | La Thangue Nicholas | Cancer therapy |
| KR102278691B1 (ko) * | 2019-08-09 | 2021-07-16 | 한국화학연구원 | 신규한 피리미딘 설폰아마이드 유도체 |
| WO2021029450A1 (ko) * | 2019-08-09 | 2021-02-18 | 한국화학연구원 | 신규한 피리미딘 설폰아마이드 유도체 및 이를 유효성분으로 포함하는 암 예방 또는 치료용 약학 조성물 |
| KR102282712B1 (ko) * | 2019-08-09 | 2021-07-27 | 한국화학연구원 | 신규한 피리미딘 설폰아마이드 유도체를 유효성분으로 포함하는 암 예방 또는 치료용 약학 조성물 |
| CN114929691A (zh) | 2019-10-02 | 2022-08-19 | 爱思开生物制药株式会社 | 双环化合物及其用途 |
| 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 |
| 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 |
| CN117088891A (zh) * | 2023-07-13 | 2023-11-21 | 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 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP4471404B2 (ja) | 1996-02-13 | 2010-06-02 | アストラゼネカ ユーケイ リミテッド | Ｖｅｇｆインヒビターとしてのキナゾリン誘導体 |
| ATE211134T1 (de) | 1996-03-05 | 2002-01-15 | 4-anilinochinazolin derivate | |
| 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 |
| DK1553097T3 (da) | 1999-02-10 | 2010-12-13 | Astrazeneca Ab | Quinazolinderivat som angiogeneseinhibitor og mellemprodukter dertil |
| NZ522074A (en) | 2000-05-31 | 2004-06-25 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| UA73993C2 (uk) | 2000-06-06 | 2005-10-17 | Астразенека Аб | Хіназолінові похідні для лікування пухлин та фармацевтична композиція |
| CA2410562A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| JP2004502766A (ja) | 2000-07-07 | 2004-01-29 | アンギオジェン・ファーマシューティカルズ・リミテッド | 血管損傷剤としてのコルヒノール誘導体 |
| AUPR201600A0 (en) | 2000-12-11 | 2001-01-11 | Fujisawa Pharmaceutical Co., Ltd. | Quinazolinone derivative |
| US20090238761A1 (en) * | 2005-01-03 | 2009-09-24 | Universita Degli Studi Di Siena | Novel Aryl Piperazine Derivatives With Medical Utility |
| 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 |
| US8940726B2 (en) | 2012-12-21 | 2015-01-27 | Epizyme, Inc. | PRMT5 inhibitors and uses thereof |
| AU2014205065A1 (en) | 2013-01-14 | 2015-07-30 | Ent Associates Of Los Alamos, Llc | Honey nasal rinse |
| CA2909894A1 (en) | 2013-04-23 | 2014-10-30 | Ramon Merce-Vidal | 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 |
| JP2017519737A (ja) | 2014-05-26 | 2017-07-20 | バイエル・ファルマ・アクティエンゲゼルシャフト | 置換テトラヒドロピリドチエノピリミジン |
| WO2015200677A2 (en) * | 2014-06-25 | 2015-12-30 | Epizyme, Inc. | Prmt5 inhibitors and uses thereof |
| CA2953572A1 (en) * | 2014-08-04 | 2016-02-11 | Epizyme, Inc. | Prmt5 inhibitors and uses thereof |
-
2017
- 2017-03-17 GB GBGB1704325.8A patent/GB201704325D0/en not_active Ceased
-
2018
- 2018-03-16 KR KR1020197029438A patent/KR102604942B1/ko active Active
- 2018-03-16 CA CA3056726A patent/CA3056726A1/en active Pending
- 2018-03-16 CN CN201880031972.3A patent/CN110621675B/zh active Active
- 2018-03-16 US US16/494,570 patent/US11274098B2/en active Active
- 2018-03-16 EP EP18711927.6A patent/EP3596073B1/en active Active
- 2018-03-16 WO PCT/EP2018/056675 patent/WO2018167276A1/en not_active Ceased
- 2018-03-16 JP JP2019571789A patent/JP7308765B2/ja active Active
- 2018-03-16 ES ES18711927T patent/ES2925115T3/es active Active
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