KR102716092B1 - Prmt5 저해제로서 사용하기 위한 신규한 6-6 이환식 방향족 고리 치환 뉴클레오시드 유사체 - Google Patents

Prmt5 저해제로서 사용하기 위한 신규한 6-6 이환식 방향족 고리 치환 뉴클레오시드 유사체 Download PDF

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KR102716092B1
KR102716092B1 KR1020187007810A KR20187007810A KR102716092B1 KR 102716092 B1 KR102716092 B1 KR 102716092B1 KR 1020187007810 A KR1020187007810 A KR 1020187007810A KR 20187007810 A KR20187007810 A KR 20187007810A KR 102716092 B1 KR102716092 B1 KR 102716092B1
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hydrogen
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KR20180041222A (ko
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통페이 우
디르크 브레머
리즈스 베케
안 뵉스
가스톤 스타니슬라스 마르셀라 디엘스
로날두즈 아르노두스 헨드리카 조셉 길리센
에드워드 챨스 로슨
비네트 판데
마르쿠스 코르넬리스 베르나르두스 카타리나 파라데
빔 버트 그리에트 스케펜스
요한네스 빌헬무스 존 에프 투링
마르셀 비엘레포에
웨이메이 선
리벤 미어포엘
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얀센 파마슈티카 엔브이
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KR1020187007810A 2015-08-26 2016-08-25 Prmt5 저해제로서 사용하기 위한 신규한 6-6 이환식 방향족 고리 치환 뉴클레오시드 유사체 Active KR102716092B1 (ko)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201562209941P 2015-08-26 2015-08-26
US62/209,941 2015-08-26
EP15184011.3 2015-09-07
EP15184011 2015-09-07
US201662306233P 2016-03-10 2016-03-10
US62/306,233 2016-03-10
PCT/EP2016/070097 WO2017032840A1 (en) 2015-08-26 2016-08-25 Novel 6-6 bicyclic aromatic ring substituted nucleoside analogues for use as prmt5 inhibitors

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KR20180041222A KR20180041222A (ko) 2018-04-23
KR102716092B1 true KR102716092B1 (ko) 2024-10-10

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Families Citing this family (78)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI870767B (zh) * 2015-08-26 2025-01-21 比利時商健生藥品公司 使用作為prmt5抑制劑之新穎經6-6雙環芳香環取代之核苷類似物
TN2018000310A1 (en) * 2016-03-10 2020-01-16 Janssen Pharmaceutica Nv Substituted nucleoside analogues for use as prmt5 inhibitors
CA2969295A1 (en) * 2016-06-06 2017-12-06 Pfizer Inc. Substituted carbonucleoside derivatives, and use thereof as a prmt5 inhibitor
CN109689663B (zh) 2016-09-14 2023-04-14 詹森药业有限公司 Menin-mll相互作用的螺二环抑制剂
MA46228A (fr) 2016-09-14 2019-07-24 Janssen Pharmaceutica Nv Inhibiteurs bicycliques fusionnés de l'interaction ménine-mll
US12084462B2 (en) 2016-09-14 2024-09-10 Janssen Pharmaceutica Nv Spiro bicyclic inhibitors of menin-MLL interaction
CN115626935B (zh) 2016-10-03 2025-07-15 詹森药业有限公司 用作prmt5抑制剂的单环和双环系统取代的卡巴核苷类似物
BR112019012106A2 (pt) 2016-12-15 2019-10-29 Janssen Pharmaceutica Nv inibidores de azepano de interação menin-mill
GB201700526D0 (en) * 2017-01-12 2017-03-01 Univ Of Hull Therapeutic use
EA201990851A1 (ru) 2017-02-24 2019-09-30 Янссен Фармацевтика Нв Новые аналоги карбануклеозида, замещенные моноциклической и бициклической кольцевой системой, для применения в качестве ингибиторов prmt5
CN110382707A (zh) 2017-02-27 2019-10-25 詹森药业有限公司 生物标志在鉴定将对用prmt5抑制剂治疗有响应的癌症患者中的用途
PL3665179T3 (pl) 2017-08-09 2021-11-29 Prelude Therapeutics, Incorporated Selektywne inhibitory metylotransferazy argininowej białek 5 (prmt5)
WO2019084470A1 (en) * 2017-10-26 2019-05-02 Prelude Therapeutics, Incorporated SELECTIVE INHIBITORS OF THE PROTEIN ARGININE METHYLTRANSFERASE 5 (PRMT5)
CA3084253A1 (en) * 2017-12-05 2019-06-13 Angex Pharmaceutical, Inc. Heterocyclic compounds as prmt5 inhibitors
IL275129B2 (en) * 2017-12-08 2023-10-01 Janssen Pharmaceutica Nv Novel spirobicyclic analogues
HUE059945T2 (hu) 2017-12-13 2023-01-28 Lupin Ltd Helyettesített biciklusos heterociklusos vegyületek, mint PRMT5 inhibitorok
US11396517B1 (en) 2017-12-20 2022-07-26 Janssen Pharmaceutica Nv Exo-aza spiro inhibitors of menin-MLL interaction
US10711007B2 (en) 2018-03-14 2020-07-14 Prelude Therapeutics Incorporated Selective inhibitors of protein arginine methyltransferase 5 (PRMT5)
BR112020018636A2 (pt) * 2018-03-14 2020-12-29 Prelude Therapeutics, Incorporated Inibidores seletivos de proteína arginina metiltransferase 5 (prmt5)
WO2020033282A1 (en) 2018-08-07 2020-02-13 Merck Sharp & Dohme Corp. Prmt5 inhibitors
US11981701B2 (en) 2018-08-07 2024-05-14 Merck Sharp & Dohme Llc PRMT5 inhibitors
WO2020033288A1 (en) 2018-08-07 2020-02-13 Merck Sharp & Dohme Corp. Prmt5 inhibitors
EP3833669A4 (en) * 2018-08-07 2022-05-11 Merck Sharp & Dohme Corp. PRMT5 INHIBITORS
WO2020132603A2 (en) * 2018-12-21 2020-06-25 Memorial Sloan-Kettering Cancer Center Salicyl-adenosinemonosulfamate analogs and uses thereof
CN109400545B (zh) * 2018-12-24 2022-03-25 济南大学 一种精氨酸甲基转移酶5抑制剂及其应用
CN109369507A (zh) * 2018-12-26 2019-02-22 重庆市碚圣医药科技股份有限公司 一种n-(2,2-二乙氧基乙基)邻苯二甲酰亚胺的提纯方法
AU2020223058A1 (en) * 2019-02-13 2021-09-09 Prelude Therapeutics, Incorporated Selective inhibitor of protein arginine methyltransferase 5 (PRMT5)
WO2020190073A1 (ko) * 2019-03-20 2020-09-24 한국화학연구원 신규한 아졸로피리미딘 헤테로고리 화합물을 유효 성분으로 함유하는 약제학적 조성물
EP3947387B1 (en) * 2019-03-25 2024-10-23 California Institute Of Technology Prmt5 inhibitors and uses thereof
AU2020256166A1 (en) 2019-04-02 2021-10-14 Aligos Therapeutics, Inc. Compounds targeting PRMT5
US20220152072A1 (en) * 2019-04-05 2022-05-19 Prelude Therapeutics, Incorporated Selective Inhibitors Of Protein Arginine Methyltransferase 5 (PRMT5)
WO2020206299A1 (en) 2019-04-05 2020-10-08 Prelude Therapeutics, Incorporated Selective inhibitors of protein arginine methyltransferase 5
KR20220016194A (ko) * 2019-05-30 2022-02-08 앤젝스 파마수티컬, 인크. Prmt5 억제제로서의 헤테로시클릭 화합물
TW202112375A (zh) * 2019-06-06 2021-04-01 比利時商健生藥品公司 使用prmt5抑制劑治療癌症之方法
PL3980417T3 (pl) * 2019-06-10 2024-03-18 Lupin Limited Inhibitory prmt5
JP7598338B2 (ja) * 2019-06-12 2024-12-11 ヤンセン ファーマシューティカ エヌ.ベー. 新規なスピロ二環式中間体
WO2021055797A1 (en) * 2019-09-18 2021-03-25 Prelude Therapeutics, Incorporated Selective inhibitors of protein arginine methyltransferase 5 (prmt5)
AU2020372002A1 (en) * 2019-10-21 2022-05-26 Accent Therapeutics, Inc Mettl3 modulators
UA128683C2 (uk) * 2019-10-22 2024-09-25 Люпін Лімітед Фармацевтична комбінація на основі інгібіторів prmt5
GB201915447D0 (en) * 2019-10-24 2019-12-11 Johnson Matthey Plc Polymorphs of avapritinib and methods of preparing the polymorphs
US20230066014A1 (en) * 2019-12-03 2023-03-02 Lupin Limited Substituted nucleoside analogs as prmt5 inhibitors
EP4076460B1 (en) 2019-12-17 2026-01-21 Merck Sharp & Dohme LLC 1,4-dihydro-2h-spiro[isoquinoline-3,4'-piperidine derivatives as prmt5 inhibitors for the treatment of cancer
JP7589247B2 (ja) 2019-12-17 2024-11-25 メルク・シャープ・アンド・ドーム・エルエルシー Prmt5阻害剤
CN115003303B (zh) 2019-12-17 2024-03-08 默沙东公司 Prmt5抑制剂
JP7554829B2 (ja) 2019-12-19 2024-09-20 ヤンセン ファーマシューティカ エヌ.ベー. 置換直鎖スピロ誘導体
TWI794742B (zh) 2020-02-18 2023-03-01 美商基利科學股份有限公司 抗病毒化合物
TWI775313B (zh) * 2020-02-18 2022-08-21 美商基利科學股份有限公司 抗病毒化合物
AU2021224588B2 (en) 2020-02-18 2024-07-18 Gilead Sciences, Inc. Antiviral compounds
CN111233869B (zh) * 2020-03-12 2022-09-16 杭州新博思生物医药有限公司 用于制备瑞德西韦关键中间体的新化合物及其制备方法
WO2021202480A1 (en) * 2020-04-01 2021-10-07 Aligos Therapeutics, Inc. Compounds targeting prmt5
US20240101589A1 (en) * 2020-10-08 2024-03-28 Strom Therapeutics Limited Inhibitors of mettl3
CN112645875A (zh) * 2020-12-09 2021-04-13 深圳海王医药科技研究院有限公司 一种盐酸丙卡特罗杂质的制备方法
EP4323362B1 (en) 2021-04-16 2025-05-07 Gilead Sciences, Inc. Methods of preparing carbanucleosides using amides
CN113234079B (zh) * 2021-04-30 2022-02-01 上海湃隆生物科技有限公司 用作prmt5抑制剂的核苷类似物
WO2023001133A1 (zh) * 2021-07-20 2023-01-26 上海齐鲁制药研究中心有限公司 Prmt5抑制剂
CN115703796A (zh) * 2021-08-09 2023-02-17 苏州恩泰新材料科技有限公司 一种瑞德西韦重要中间体制备方法
AU2022328698B2 (en) 2021-08-18 2025-02-20 Gilead Sciences, Inc. Phospholipid compounds and methods of making and using the same
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
CN116655638B (zh) * 2022-05-12 2024-01-26 上海齐鲁制药研究中心有限公司 氘代prmt5抑制剂
CN116003339B (zh) * 2022-12-01 2024-06-28 南京师范大学 一种巨噬细胞迁移抑制因子mif双光子荧光探针及其制备方法和应用
WO2024170488A1 (en) 2023-02-13 2024-08-22 Astrazeneca Ab Prmt5 inhibitor for use in cancer therapy
AU2024265078A1 (en) 2023-05-04 2025-12-11 Revolution Medicines, Inc. Combination therapy for a ras related disease or disorder
IL326136A (en) 2023-08-07 2026-03-01 Revolution Medicines Inc RMC-6291 for use in the treatment of a disease or disorder associated with the RAS protein
US20250154171A1 (en) 2023-10-12 2025-05-15 Revolution Medicines, Inc. Ras inhibitors
EP4553080A1 (en) 2023-11-07 2025-05-14 Ustav Organicke Chemie a Biochemie AV CR, v.v.i. Nucleoside derivatives as antiviral agents against coronaviruses
WO2025171296A1 (en) 2024-02-09 2025-08-14 Revolution Medicines, Inc. Ras inhibitors
WO2025240847A1 (en) 2024-05-17 2025-11-20 Revolution Medicines, Inc. Ras inhibitors
US20250375445A1 (en) 2024-06-07 2025-12-11 Revolution Medicines, Inc. Methods of treating a ras protein-related disease or disorder
WO2025265060A1 (en) 2024-06-21 2025-12-26 Revolution Medicines, Inc. Therapeutic compositions and methods for managing treatment-related effects
WO2026006747A1 (en) 2024-06-28 2026-01-02 Revolution Medicines, Inc. Ras inhibitors
WO2026008533A1 (en) 2024-07-01 2026-01-08 Janssen Pharmaceutica Nv Prmt5 inhibitors for treating adenomas
WO2026015790A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Methods of treating a ras related disease or disorder
WO2026015796A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Methods of treating a ras related disease or disorder
WO2026015825A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Use of ras inhibitor for treating pancreatic cancer
WO2026015801A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Methods of treating a ras related disease or disorder
WO2026050446A1 (en) 2024-08-29 2026-03-05 Revolution Medicines, Inc. Ras inhibitors
WO2026072904A2 (en) 2024-09-26 2026-04-02 Revolution Medicines, Inc. Compositions and methods for treating lung cancer

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003074083A1 (en) 2002-03-04 2003-09-12 Pfizer Inc. Combination therapies for treating methylthioadenosine phosphorylase deficient cells
JP2005527502A (ja) 2002-02-19 2005-09-15 シーブイ・セラピューティクス・インコーポレイテッド A1アデノシン受容体の部分的および全アゴニスト
WO2014100695A1 (en) 2012-12-21 2014-06-26 Epizyme, Inc. Prmt5 inhibitors and uses thereof

Family Cites Families (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4224438A (en) 1970-07-14 1980-09-23 Boehringer Mannheim Gmbh Adenosine-5'-carboxylic acid amides
US6143749A (en) 1995-06-07 2000-11-07 Abbott Laboratories Heterocyclic substituted cyclopentane compounds
AU2002351077A1 (en) 2001-11-05 2003-05-19 Exiqon A/S Oligonucleotides modified with novel alpha-l-rna analogues
US7034147B2 (en) 2001-11-29 2006-04-25 Irm Llc Nucleoside analog libraries
US7144674B2 (en) * 2002-03-20 2006-12-05 Sumitomo Chemical Company, Limited Positive resist composition
AU2002951247A0 (en) 2002-09-06 2002-09-19 Alchemia Limited Compounds that interact with kinases
US20060167241A1 (en) 2003-07-15 2006-07-27 Mitsui Chemicals, Inc. Method for synthesizing cyclic bisdinucleoside
AU2004311702A1 (en) 2003-12-19 2005-07-21 Koronis Pharmaceuticals, Inc. Mutagenic heterocycles
WO2006078752A2 (en) 2005-01-21 2006-07-27 Methylgene, Inc. Inhibitors of dna methyltransferase
WO2008001101A2 (en) 2006-06-29 2008-01-03 Astex Therapeutics Limited Pharmaceutical combinations
US20080132525A1 (en) 2006-12-04 2008-06-05 Methylgene Inc. Inhibitors of DNA Methyltransferase
EP2342616A2 (en) 2008-09-23 2011-07-13 Alnylam Pharmaceuticals Inc. Chemical modifications of monomers and oligonucleotides with cycloaddition
AU2010330823A1 (en) 2009-12-18 2012-07-05 Joslin Diabetes Center, Inc. Beta-cell replication promoting compounds and methods of their use
CA2819620A1 (en) 2010-12-03 2012-06-21 Epizyme, Inc. Modulators of histone methyltransferase, and methods of use thereof
EP2646454B1 (en) * 2010-12-03 2015-07-08 Epizyme, Inc. 7-deazapurine modulators of histone methyltransferase, and methods of use thereof
MX2013006951A (es) 2010-12-16 2013-10-03 Abbvie Inc Compuestos antivirales.
US9284343B2 (en) 2011-04-04 2016-03-15 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services 2′-O-aminooxymethyl nucleoside derivatives for use in the synthesis and modification of nucleosides, nucleotides and oligonucleotides
JP2014530910A (ja) 2011-10-24 2014-11-20 グラクソスミスクライン、インテレクチュアル、プロパティー、ナンバー2、リミテッドGlaxosmithkline Intellectual Property No.2 Limited 新規化合物
WO2013151975A1 (en) 2012-04-02 2013-10-10 Northeastern University Compositions and methods for the inhibition of methyltransferases
WO2014035140A2 (en) * 2012-08-30 2014-03-06 Kainos Medicine, Inc. Compounds and compositions for modulating histone methyltransferase activity
US20140100184A1 (en) 2012-08-31 2014-04-10 Baylor College Of Medicine Selective inhibitors of histone methyltransferase dot1l
US9611257B2 (en) 2012-12-21 2017-04-04 Epizyme, Inc. PRMT5 inhibitors and uses thereof
UA118548C2 (uk) 2012-12-21 2019-02-11 Епізайм, Інк. Тетрагідро- та дигідроізохіноліни як інгібітори prmt5 та їх застосування
EP3406607A1 (en) 2012-12-21 2018-11-28 Epizyme, Inc. Prmt5 inhibitors containing a dihydro- or tetrahydroisoquinoline and uses thereof
JP6510485B2 (ja) 2013-03-15 2019-05-08 オハイオ・ステイト・イノベーション・ファウンデーション Prmt5インヒビターおよびそれらの使用方法
US10087151B2 (en) 2014-01-09 2018-10-02 The J. David Gladstone Institutes, A Testimentary Trust Established Under The Will Of J. David Gladstone Substituted benzoxazine and related compounds
WO2015200680A2 (en) 2014-06-25 2015-12-30 Epizyme, Inc. Prmt5 inhibitors and uses thereof
SG11201610476VA (en) 2014-07-01 2017-01-27 Millennium Pharm Inc Heteroaryl compounds useful as inhibitors of sumo activating enzyme
JP6584521B2 (ja) 2015-02-24 2019-10-02 ファイザー・インク 抗がん剤として有用な置換ヌクレオシド誘導体
TWI870767B (zh) * 2015-08-26 2025-01-21 比利時商健生藥品公司 使用作為prmt5抑制劑之新穎經6-6雙環芳香環取代之核苷類似物
PE20181894A1 (es) 2016-03-10 2018-12-11 Janssen Pharmaceutica Nv Nuevos analogos de nucleosidos sustituidos para su uso como inhibidores de prmt 5
CN115626935B (zh) * 2016-10-03 2025-07-15 詹森药业有限公司 用作prmt5抑制剂的单环和双环系统取代的卡巴核苷类似物
EA201990851A1 (ru) 2017-02-24 2019-09-30 Янссен Фармацевтика Нв Новые аналоги карбануклеозида, замещенные моноциклической и бициклической кольцевой системой, для применения в качестве ингибиторов prmt5
CN110382707A (zh) 2017-02-27 2019-10-25 詹森药业有限公司 生物标志在鉴定将对用prmt5抑制剂治疗有响应的癌症患者中的用途
IL275129B2 (en) 2017-12-08 2023-10-01 Janssen Pharmaceutica Nv Novel spirobicyclic analogues

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005527502A (ja) 2002-02-19 2005-09-15 シーブイ・セラピューティクス・インコーポレイテッド A1アデノシン受容体の部分的および全アゴニスト
WO2003074083A1 (en) 2002-03-04 2003-09-12 Pfizer Inc. Combination therapies for treating methylthioadenosine phosphorylase deficient cells
WO2014100695A1 (en) 2012-12-21 2014-06-26 Epizyme, Inc. Prmt5 inhibitors and uses thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Bioorganic & Medicinal Chemistry Letters, 2005, 15(11), pp.2829-2833.

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