JP6289485B2 - Pde4のヘテロアリール阻害剤 - Google Patents

Pde4のヘテロアリール阻害剤 Download PDF

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JP6289485B2
JP6289485B2 JP2015539801A JP2015539801A JP6289485B2 JP 6289485 B2 JP6289485 B2 JP 6289485B2 JP 2015539801 A JP2015539801 A JP 2015539801A JP 2015539801 A JP2015539801 A JP 2015539801A JP 6289485 B2 JP6289485 B2 JP 6289485B2
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formula
compound according
pde4
certain embodiments
lower alkyl
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JP2016505512A5 (enExample
JP2016505512A (ja
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マーク イー ガーニー
マーク イー ガーニー
ティモシー ジェイ ハーゲン
ティモシー ジェイ ハーゲン
シュエシェン モー
シュエシェン モー
エー ベレクープ
エー ベレクープ
ドナ エル ロメロ
ドナ エル ロメロ
ロバート エフ キャンベル
ロバート エフ キャンベル
ジョエル アール ウォーカー
ジョエル アール ウォーカー
レイ ジュー
レイ ジュー
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テトラ ディスカバリー パートナーズ エルエルシー
テトラ ディスカバリー パートナーズ エルエルシー
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    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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    • A61K31/5375—1,4-Oxazines, e.g. morpholine
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Families Citing this family (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI2861566T1 (sl) 2012-06-13 2017-03-31 F. Hoffmann-La Roche Ag Novi diazaspirocikloalkan in azaspirocikloalkan
PL2900669T3 (pl) 2012-09-25 2020-01-31 F. Hoffmann-La Roche Ag Pochodne heksahydropirolo[3,4-C]pirolu i związki pokrewne jako inhibitory autotaksyny (ATX) oraz inhibitory produkcji kwasu lizofosfatydowego (LPA) do leczenia np. chorób nerek
WO2014066659A1 (en) 2012-10-25 2014-05-01 Tetra Discovery Partners, Llc. Heteroaryl inhibitors of pde4
MX2015009678A (es) * 2013-02-04 2015-11-25 Gruenenthal Gmbh Compuestos de pirimidina condensada sustituida con amino en la posicion 4 como inhibidores de fosfodiesterasa 4 (pde4).
JP6307525B2 (ja) * 2013-02-04 2018-04-04 グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 新規の置換縮合ピリミジン化合物
AR095079A1 (es) 2013-03-12 2015-09-16 Hoffmann La Roche Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo
AU2014356583B2 (en) 2013-11-26 2019-02-28 F. Hoffmann-La Roche Ag New octahydro-cyclobuta (1,2-c;3,4-c')dipyrrol-2-yl
CR20160418A (es) 2014-03-26 2016-11-07 Hoffmann La Roche Nuevos compuestos biciclicos de 7 eslabones
MA50635A (fr) 2014-03-26 2020-08-12 Hoffmann La Roche Nouveaux composés bicycliques comme inhibiteurs de la production d'autotaxin (atx) et de l'acide lysophosphatidique
WO2016161268A1 (en) 2015-04-01 2016-10-06 Enanta Pharmaceuticals, Inc. Hepatitis b antviral agents
MA41898A (fr) 2015-04-10 2018-02-13 Hoffmann La Roche Dérivés de quinazolinone bicyclique
US10738035B2 (en) 2015-05-13 2020-08-11 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
WO2017011552A1 (en) 2015-07-13 2017-01-19 Enanta Pharmaceuticals, Inc. Hepatitis b antiviral agents
US10301255B2 (en) 2015-07-22 2019-05-28 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
EP3344619B1 (en) 2015-09-04 2020-10-28 H. Hoffnabb-La Roche Ag Phenoxymethyl derivatives
WO2017050747A1 (en) 2015-09-24 2017-03-30 F. Hoffmann-La Roche Ag New bicyclic compounds as dual atx/ca inhibitors
AU2016328437A1 (en) 2015-09-24 2018-01-25 F. Hoffmann-La Roche Ag Bicyclic compounds as ATX inhibitors
BR112018006080A2 (pt) 2015-09-24 2018-10-09 F. Hoffmann-La Roche Ag novos compostos bicíclicos como inibidores de dupla ação de atx/ca
MA42918A (fr) 2015-09-24 2018-08-01 Hoffmann La Roche Composés bicycliques utilisés en tant qu'inhibiteurs d'atx
WO2017136403A1 (en) 2016-02-02 2017-08-10 Enanta Pharmaceuticals, Inc. Hepatitis b antiviral agents
KR102398439B1 (ko) 2016-03-07 2022-05-16 이난타 파마슈티칼스, 인코포레이티드 B형 간염 항바이러스제
EP3468561A4 (en) 2016-06-10 2019-12-04 Enanta Pharmaceuticals, Inc. Hepatitis b antiviral agents
RU2019132254A (ru) 2017-03-16 2021-04-16 Ф. Хоффманн-Ля Рош Аг Гетероциклические соединения, пригодные в качестве дуальных ингибиторов atx/ca
EP3596060B1 (en) 2017-03-16 2023-09-20 F. Hoffmann-La Roche AG New bicyclic compounds as atx inhibitors
SG11202001685TA (en) 2017-08-28 2020-03-30 Enanta Pharm Inc Hepatitis b antiviral agents
US11365204B2 (en) 2017-09-20 2022-06-21 UNION therapeutics A/S Substituted dihydrothienopyrimidines and their use as phosphodiesterase inhibitors
WO2019113173A1 (en) 2017-12-06 2019-06-13 Enanta Pharmaceuticals, Inc. Hepatitis b antiviral agents
US10723733B2 (en) 2017-12-06 2020-07-28 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
WO2019115774A1 (en) 2017-12-15 2019-06-20 Leo Pharma A/S Substituted azetidine dihydrothienopyrimidines and their use as phosphodiesterase inhibitors
WO2019115776A1 (en) 2017-12-15 2019-06-20 Leo Pharma A/S Substituted azetidine dihydrothienopyridines and their use as phosphodiesterase inhibitors
US11058678B2 (en) 2018-01-22 2021-07-13 Enanta Pharmaceuticals, Inc. Substituted heterocycles as antiviral agents
US10729688B2 (en) 2018-03-29 2020-08-04 Enanta Pharmaceuticals, Inc. Hepatitis B antiviral agents
CA3135420A1 (en) * 2018-04-05 2019-10-10 Universiteit Hasselt Selective pde4d inhibitors against demyelinating diseases
CN108997394A (zh) * 2018-06-12 2018-12-14 广州百霆医药科技有限公司 苯并氧杂硼杂环戊烷类化合物及其制备方法
TW202024093A (zh) 2018-09-21 2020-07-01 美商安塔製藥公司 作為抗病毒劑之官能化雜環
KR102576125B1 (ko) * 2018-10-05 2023-09-08 화이자 인코포레이티드 붕소 함유 pde4 억제제
EP3883570A4 (en) 2018-11-21 2022-07-13 Enanta Pharmaceuticals, Inc. FUNCTIONALIZED HETEROCYCLES AS ANTIVIRAL AGENTS
CN111635400A (zh) 2019-03-02 2020-09-08 察略盛医药科技(上海)有限公司 吡唑并[1,5-a]吡啶类衍生物、及其制备方法和用途
WO2020214874A1 (en) * 2019-04-18 2020-10-22 Tetra Discovery Partners, Inc. Salts and polymorphs of a pde4 inhibitor
EP3969458A4 (en) 2019-05-13 2023-05-17 Borah, Inc. CHEMICAL COMPOUNDS
WO2020247444A1 (en) 2019-06-03 2020-12-10 Enanta Pharmaceuticals, Inc, Hepatitis b antiviral agents
US11472808B2 (en) 2019-06-04 2022-10-18 Enanta Pharmaceuticals, Inc. Substituted pyrrolo[1,2-c]pyrimidines as hepatitis B antiviral agents
WO2020247561A1 (en) 2019-06-04 2020-12-10 Enanta Pharmaceuticals, Inc, Hepatitis b antiviral agents
EP3994142A4 (en) 2019-07-03 2023-09-06 Borah, Inc. CHEMICAL COMPOUNDS
WO2021007488A1 (en) 2019-07-11 2021-01-14 Enanta Pharmaceuticals, Inc. Substituted heterocycles as antiviral agents
WO2021055425A2 (en) 2019-09-17 2021-03-25 Enanta Pharmaceuticals, Inc. Functionalized heterocycles as antiviral agents
US11802125B2 (en) 2020-03-16 2023-10-31 Enanta Pharmaceuticals, Inc. Functionalized heterocyclic compounds as antiviral agents
CN114149410B (zh) * 2020-09-07 2025-02-25 四川科伦博泰生物医药股份有限公司 吡啶并环类化合物及其制备方法和用途
US20240116856A1 (en) * 2020-11-05 2024-04-11 Young Biopharma, Llc Novel capsaicin analogs and uses thereof
EP4748445A3 (en) * 2020-12-25 2026-06-03 Reistone Biopharma Company Limited Borate derivative and uses thereof
CN115521946B (zh) * 2022-10-14 2024-06-21 浙江玖世生物科技有限公司 一种TiOx基光酶催化剂合成(R)-1-[3,5-二(三氟甲基)]苯乙醇的方法
JPWO2024135840A1 (enExample) * 2022-12-23 2024-06-27
CN118871444A (zh) * 2023-02-28 2024-10-29 上海翊石医药科技有限公司 二氢噻吩并嘧啶衍生物的制备方法和用途
EP4678644A1 (en) 2023-04-13 2026-01-14 Shanghai Yidi Biotechnology Co., Ltd. Substituted dihydrothienopyrimidine compound, preparation method therefor, and use thereof
GB202306663D0 (en) 2023-05-05 2023-06-21 Union Therapeutics As Combination therapy
CN122421966A (zh) 2023-10-12 2026-07-17 傲拓神经科学公司 用替伐普兰治疗神经精神病症
CN120398908A (zh) * 2024-02-01 2025-08-01 艾派克斯生物科技有限公司 Pde4b抑制剂及其药物组合物和用途
WO2025221488A1 (en) 2024-04-16 2025-10-23 Alto Neuroscience, Inc. Transdermal administration of pde4 inhibitors for reduction in adverse events
WO2025240378A1 (en) * 2024-05-13 2025-11-20 Board Of Regents Of The University Of Nebraska Inhibitors of phosphodiesterases
KR20260015118A (ko) * 2024-07-24 2026-02-02 제일약품주식회사 디하이드로티오피라노피리미딘 화합물 및 이의 용도

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK23392D0 (da) 1992-02-24 1992-02-24 Novo Nordisk As Heterocykliske forbindelser, deres anvendelse og fremstilling
FR2754260B1 (fr) 1996-10-04 1998-10-30 Adir Nouveaux derives substitues de biphenyle ou de phenylpyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
AU5648599A (en) * 1998-09-11 2000-04-03 Kyorin Pharmaceutical Co. Ltd. Phosphonic ester derivatives and process for producing the same
ATE368657T1 (de) 2002-03-08 2007-08-15 Lilly Co Eli Pyrrol-2,5-dion derivate und deren verwendung als gsk-3 inhibitoren
US20050014767A1 (en) 2003-01-29 2005-01-20 Magnus Pfahl Benzoxazole, benzothiazole, and benzimidazole derivatives for the treatment of cancer and other diseases
JP2006123639A (ja) 2004-10-27 2006-05-18 Mitsubishi Electric Corp ホームドア状態認識システム
WO2006123639A1 (ja) * 2005-05-18 2006-11-23 Asahi Kasei Pharma Corporation ピリミジン誘導体
US20060293343A1 (en) * 2005-05-18 2006-12-28 Asahi Kasei Pharma Corporation Pyrimidine derivatives
US7919519B2 (en) 2005-11-23 2011-04-05 Epix Pharmaceuticals Inc. S1P receptor modulating compounds and use thereof
WO2009146388A1 (en) 2008-05-28 2009-12-03 The Trustees Of Columbia University In The City Of New York Voxel-based methods for assessing subjects using positron emission tomography
WO2010027975A1 (en) * 2008-09-04 2010-03-11 Anacor Pharmaceuticals, Inc. Boron-containing small molecules
RU2380890C1 (ru) 2008-10-17 2010-02-10 Государственное образовательное учреждение высшего профессионального образования Марийский государственный технический университет Способ испытания травяного покрова на прирусловой пойме реки
WO2010059838A2 (en) 2008-11-20 2010-05-27 Decode Genetics Ehf Pde4 inhibitors selective for the long form of pde4 for treating inflammation and avoiding side effects
JP2012519160A (ja) * 2009-02-27 2012-08-23 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Pde4阻害剤及びnsaidを含有する組み合わせ薬
EP2380890A1 (en) * 2010-04-23 2011-10-26 Almirall, S.A. New 7,8-dihydro-1,6-naphthyridin-5(6h)-one-derivatives as PDE4 inhibitors
US8889123B2 (en) 2010-08-19 2014-11-18 Allergan, Inc. Compositions and soft tissue replacement methods
WO2014066659A1 (en) * 2012-10-25 2014-05-01 Tetra Discovery Partners, Llc. Heteroaryl inhibitors of pde4
JP6307525B2 (ja) * 2013-02-04 2018-04-04 グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング 新規の置換縮合ピリミジン化合物
WO2015048407A1 (en) 2013-09-26 2015-04-02 Tetra Discovery Partners, LLC Heteroaryl inhibitors of pde4
WO2016049595A1 (en) 2014-09-26 2016-03-31 Tetra Discovery Partners, LLC Heteroaryl inhibitors of pde4
WO2020214874A1 (en) * 2019-04-18 2020-10-22 Tetra Discovery Partners, Inc. Salts and polymorphs of a pde4 inhibitor

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