JP6936814B2 - Nik阻害剤としてのシアノインドリン誘導体 - Google Patents

Nik阻害剤としてのシアノインドリン誘導体 Download PDF

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JP6936814B2
JP6936814B2 JP2018562323A JP2018562323A JP6936814B2 JP 6936814 B2 JP6936814 B2 JP 6936814B2 JP 2018562323 A JP2018562323 A JP 2018562323A JP 2018562323 A JP2018562323 A JP 2018562323A JP 6936814 B2 JP6936814 B2 JP 6936814B2
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alkyl
substituted
het
ring
cycloalkyl
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JP2019524646A5 (OSRAM
JP2019524646A (ja
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スタンスフィールド,イアン
ケロル,オリビエ,アレクシス,ジョルジュ
リニー,ヤニック,エメ,エディ
グロス,ジェラルド,マックス
ジャコビー,エドガー
ミーアポール,リーベン
グリーン,サイモン,リチャード
ハインド,ジョージ
クラゴウスキ,ヤヌシュ,ヨゼフ
マクラウド,カラム
マン,サミュエル,エドワード
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ヤンセン ファーマシューティカ エヌ.ベー.
ヤンセン ファーマシューティカ エヌ.ベー.
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5365Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines ortho- or peri-condensed with heterocyclic ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/53751,4-Oxazines, e.g. morpholine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04Ortho-condensed systems
    • C07D491/044Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/052Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D498/00Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
JP2018562323A 2016-06-30 2017-06-29 Nik阻害剤としてのシアノインドリン誘導体 Active JP6936814B2 (ja)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
EP16177142 2016-06-30
EP16177131.6 2016-06-30
EP16177147 2016-06-30
EP16177131 2016-06-30
EP16177142.3 2016-06-30
EP16177147.2 2016-06-30
PCT/EP2017/066125 WO2018002219A1 (en) 2016-06-30 2017-06-29 Cyanoindoline derivatives as nik inhibitors

Publications (3)

Publication Number Publication Date
JP2019524646A JP2019524646A (ja) 2019-09-05
JP2019524646A5 JP2019524646A5 (OSRAM) 2020-08-06
JP6936814B2 true JP6936814B2 (ja) 2021-09-22

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JP2018562323A Active JP6936814B2 (ja) 2016-06-30 2017-06-29 Nik阻害剤としてのシアノインドリン誘導体

Country Status (8)

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US (2) US20190119299A1 (OSRAM)
EP (1) EP3478673B1 (OSRAM)
JP (1) JP6936814B2 (OSRAM)
KR (1) KR102587619B1 (OSRAM)
CN (1) CN109689645B (OSRAM)
AU (1) AU2017289317B2 (OSRAM)
ES (1) ES2837157T3 (OSRAM)
WO (1) WO2018002219A1 (OSRAM)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI3405196T1 (sl) 2016-01-22 2020-03-31 Janssen Pharmaceutica Nv Novi substituirani derivati cianoindolina kot inhibitorji NIK
KR102720461B1 (ko) 2016-01-22 2024-10-21 잔센파마슈티카엔.브이. Nik 억제제로서의 신규 6원 헤테로방향족 치환된 시아노인돌린 유도체
ES2837157T3 (es) 2016-06-30 2021-06-29 Janssen Pharmaceutica Nv Derivados de cianoindolina como inhibidores de NIK
CA3027416A1 (en) 2016-06-30 2018-01-04 Janssen Pharmaceutica Nv Heteroaromatic derivatives as nik inhibitors
RS66105B1 (sr) 2019-05-31 2024-11-29 Janssen Pharmaceutica Nv Inhibitori malih molekula nf-kb koji indukuju kinazu
MA56462A (fr) * 2019-07-04 2022-05-11 Qilu Regor Therapeutics Inc Inhibiteurs de hpk1 et leurs utilisations
WO2022214008A1 (zh) * 2021-04-08 2022-10-13 杭州阿诺生物医药科技有限公司 高活性hpk1激酶抑制剂
CN114380806B (zh) * 2022-03-24 2022-06-10 中国药科大学 2-氨基-4-吲哚基嘧啶类化合物及其制备方法与应用

Family Cites Families (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2386218A1 (en) 1999-10-07 2001-04-12 Amgen Inc. Triazine kinase inhibitors
CA2400447C (en) 2000-02-17 2008-04-22 Amgen Inc. Kinase inhibitors
WO2001064642A2 (en) 2000-02-29 2001-09-07 Cor Therapeutics, Inc. Benzamides and related inhibitors of factor xa
ES2292753T4 (es) 2001-03-29 2009-02-16 Vertex Pharmaceuticals Incorporated Inhibidores de quinasas n-terminales c-jun (jnk) y otras proteina quinasas.
HUP0402352A2 (hu) 2001-06-19 2005-02-28 Bristol-Myers Squibb Co. Foszfodiészteráz (PDE) 7 inhibitorként alkalmazható pirimidinszármazékok és ezeket tartalmazó gyógyszerkészítmények
WO2003030909A1 (en) * 2001-09-25 2003-04-17 Bayer Pharmaceuticals Corporation 2- and 4-aminopyrimidines n-substtituded by a bicyclic ring for use as kinase inhibitors in the treatment of cancer
CN101039919A (zh) * 2004-10-13 2007-09-19 惠氏公司 经n-苯磺酰基取代的苯胺基嘧啶类似物
US20110086834A1 (en) * 2008-06-26 2011-04-14 Amgen Inc. Alkynyl alcohols as kinase inhibitors
NZ589843A (en) 2008-06-27 2012-12-21 Avila Therapeutics Inc Pyrimidine heteroaryl compounds and uses thereof as protein kinase inhibitors
WO2010042337A1 (en) * 2008-10-07 2010-04-15 Merck Sharp & Dohme Corp. Novel 6-azaindole aminopyrimidine derivatives having nik inhibitory activity
CN108752280A (zh) 2009-08-17 2018-11-06 纪念斯隆-凯特琳癌症中心 热休克蛋白结合化合物、组合物以及其制备和使用方法
WO2011153553A2 (en) 2010-06-04 2011-12-08 The Regents Of The University Of California Methods and compositions for kinase inhibition
KR101764952B1 (ko) 2010-07-29 2017-08-03 리겔 파마슈티칼스, 인크. Ampk-활성화 헤테로시클릭 화합물 및 그의 사용 방법
CA2832919A1 (en) 2011-04-12 2012-10-18 Ryan C. Holcomb Compounds, compositions, and therapeutic uses thereof
TWI663166B (zh) 2013-04-24 2019-06-21 健生藥品公司 新化合物
JP6524094B2 (ja) 2013-08-30 2019-06-05 ピーティーシー セラピューティクス, インコーポレイテッド 置換ピリミジンBmi−1阻害剤
TWI704146B (zh) * 2013-09-26 2020-09-11 比利時商健生藥品公司 用作NIK抑制劑之新的1-(4-嘧啶基)-1H-吡唑並[3,2-c]吡啶衍生物
TWI627173B (zh) 2013-09-26 2018-06-21 比利時商健生藥品公司 作為NIK抑制劑的新穎3-(1H-吡唑-4-基)-1H-吡咯并[2,3-c]吡啶衍生物
WO2015154038A1 (en) 2014-04-04 2015-10-08 Syros Pharmaceuticals, Inc. Inhibitors of cyclin-dependent kinase 7 (cdk7)
KR20170030474A (ko) 2014-05-22 2017-03-17 더 유니버시티 오브 시드니 오메가―3 유사체
WO2016022645A1 (en) 2014-08-06 2016-02-11 Merck Sharp & Dohme Corp. Heterocyclic cgrp receptor antagonists
JP6499282B2 (ja) 2014-09-26 2019-04-10 ギリアード サイエンシーズ, インコーポレイテッド Tank結合キナーゼ阻害剤化合物として有用なアミノトリアジン誘導体
CN106928216A (zh) 2015-12-31 2017-07-07 中国科学院上海药物研究所 具有erk激酶抑制活性的化合物、其制备方法和用途
SI3405196T1 (sl) 2016-01-22 2020-03-31 Janssen Pharmaceutica Nv Novi substituirani derivati cianoindolina kot inhibitorji NIK
KR102720461B1 (ko) 2016-01-22 2024-10-21 잔센파마슈티카엔.브이. Nik 억제제로서의 신규 6원 헤테로방향족 치환된 시아노인돌린 유도체
CN114539284A (zh) 2016-03-16 2022-05-27 库拉肿瘤学公司 经取代的menin-mll抑制剂及使用方法
CA3027416A1 (en) 2016-06-30 2018-01-04 Janssen Pharmaceutica Nv Heteroaromatic derivatives as nik inhibitors
ES2837157T3 (es) 2016-06-30 2021-06-29 Janssen Pharmaceutica Nv Derivados de cianoindolina como inhibidores de NIK

Also Published As

Publication number Publication date
KR102587619B1 (ko) 2023-10-11
US20210032267A1 (en) 2021-02-04
AU2017289317A1 (en) 2019-01-17
ES2837157T3 (es) 2021-06-29
US11186589B2 (en) 2021-11-30
CA3027418A1 (en) 2018-01-04
AU2017289317B2 (en) 2021-04-01
EP3478673A1 (en) 2019-05-08
WO2018002219A1 (en) 2018-01-04
CN109689645B (zh) 2022-06-03
EP3478673B1 (en) 2020-09-16
US20190119299A1 (en) 2019-04-25
KR20190025949A (ko) 2019-03-12
JP2019524646A (ja) 2019-09-05
CN109689645A (zh) 2019-04-26

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