KR101738195B1 - 항종양 활성을 갖는 크로메논 유도체 - Google Patents

항종양 활성을 갖는 크로메논 유도체 Download PDF

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KR101738195B1
KR101738195B1 KR1020127012933A KR20127012933A KR101738195B1 KR 101738195 B1 KR101738195 B1 KR 101738195B1 KR 1020127012933 A KR1020127012933 A KR 1020127012933A KR 20127012933 A KR20127012933 A KR 20127012933A KR 101738195 B1 KR101738195 B1 KR 101738195B1
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ethyl
oxo
chromen
morpholino
formula
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KR20120098724A (ko
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베르나르 크리스토퍼 발람
세바스틴 루이스 데고스
데 브렝트 크리스틴 마리 폴 랑베르-반
레미 로버트 모르겐팅
패트릭 쁠레
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아스트라제네카 아베
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/275—Nitriles; Isonitriles
    • A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
    • A—HUMAN NECESSITIES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
    • A—HUMAN NECESSITIES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic 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
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
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    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
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    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C—CHEMISTRY; METALLURGY
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    • C07D405/00—Heterocyclic 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
    • C07D405/02—Heterocyclic 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
    • C07D405/06—Heterocyclic 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 linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
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    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • General Health & Medical Sciences (AREA)
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  • Pharmacology & Pharmacy (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
KR1020127012933A 2009-10-27 2010-10-25 항종양 활성을 갖는 크로메논 유도체 Expired - Fee Related KR101738195B1 (ko)

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EP09306017.6 2009-10-27
EP09306017 2009-10-27
PCT/GB2010/051788 WO2011051704A1 (en) 2009-10-27 2010-10-25 Chromenone derivatives with anti-tumour activity

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KR20120098724A KR20120098724A (ko) 2012-09-05
KR101738195B1 true KR101738195B1 (ko) 2017-05-19

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021230733A1 (ko) * 2020-05-15 2021-11-18 제이투에이치바이오텍 주식회사 3원환 화합물 및 이의 의약 용도

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2725014C (en) 2008-05-30 2014-06-17 Amgen Inc. Inhibitors of pi3 kinase
US8399460B2 (en) * 2009-10-27 2013-03-19 Astrazeneca Ab Chromenone derivatives
UY34013A (es) * 2011-04-13 2012-11-30 Astrazeneca Ab ?compuestos de cromenona con actividad anti-tumoral?.
EP2948447B1 (en) 2013-01-23 2016-09-21 Astrazeneca AB Chemical compounds
KR102222346B1 (ko) * 2013-03-04 2021-03-02 아스트라제네카 아베 조합 치료
EA201692266A1 (ru) 2014-06-13 2017-06-30 Джилид Сайэнс, Инк. Ингибиторы фосфатидилинозитол-3-киназы
MX2016016530A (es) 2014-06-13 2017-03-27 Gilead Sciences Inc Inhibidores de fosfatidilinositol 3-quinasa.
NZ726638A (en) 2014-06-13 2018-04-27 Gilead Sciences Inc Phosphatidylinositol 3-kinase inhibitors
EA201692267A1 (ru) 2014-06-13 2017-06-30 Джилид Сайэнс, Инк. Ингибиторы фосфатидилинозитол-3-киназы
HK1231477A1 (zh) 2014-06-13 2017-12-22 吉利德科学公司 磷脂酰肌醇3-激酶抑制剂
CN104744376A (zh) * 2015-03-14 2015-07-01 长沙深橙生物科技有限公司 一种2-异丙基嘧啶衍生物的制备方法
CN104803921A (zh) * 2015-03-14 2015-07-29 长沙深橙生物科技有限公司 一种苯取代嘧啶衍生物的制备方法
KR101766731B1 (ko) 2015-06-23 2017-08-10 충남대학교산학협력단 강심 활성을 갖는 크로메논 유도체 및 이를 포함하는 심부전의 예방 또는 치료용 약학 조성물
JP6912460B2 (ja) * 2015-10-09 2021-08-04 ヤンセン ファーマシューティカ エヌ．ベー． ＰＩ３Ｋβ阻害剤としてのキノキサリンおよびピリドピラジン誘導体
TW201825465A (zh) 2016-09-23 2018-07-16 美商基利科學股份有限公司 磷脂醯肌醇3-激酶抑制劑
TW201813963A (zh) 2016-09-23 2018-04-16 美商基利科學股份有限公司 磷脂醯肌醇3-激酶抑制劑
WO2018057808A1 (en) 2016-09-23 2018-03-29 Gilead Sciences, Inc. Benzimidazole derivatives and their use as phosphatidylinositol 3-kinase inhibitors
TW201815787A (zh) 2016-09-23 2018-05-01 美商基利科學股份有限公司 磷脂醯肌醇3-激酶抑制劑
AR121719A1 (es) 2020-04-03 2022-06-29 Petra Pharma Corp Inhibidores alostéricos de cromenona del fosfoinosítido 3-quinasa (pi3k) para el tratamiento de enfermedades
CN117615763A (zh) * 2021-02-01 2024-02-27 健道生物医药有限公司 磷酸肌醇3激酶β抑制剂及其组合物和制备方法
US20230014445A1 (en) * 2021-05-03 2023-01-19 Petra Pharma Corporation Allosteric chromenone inhibitors of phosphoinositide 3-kinase (pi3k) for the treatment of disease
WO2022235574A1 (en) 2021-05-03 2022-11-10 Petra Pharma Corporation Allosteric chromenone inhibitors of phosphoinositide 3-kinase (pi3k) for the treatment of disease
EP4347040A1 (en) * 2021-05-27 2024-04-10 Petra Pharma Corporation Allosteric chromenone inhibitors of phosphoinositide 3-kinase (pi3k) for the treatment of cancer
TW202329930A (zh) 2021-09-30 2023-08-01 美商佩特拉製藥公司 用於治療疾病之磷酸肌醇3-激酶(pi3k)之異位色烯酮抑制劑
CA3232906A1 (en) * 2021-10-07 2023-04-13 Alessandro Boezio Pi3k-alpha inhibitors and methods of use thereof
WO2023104111A1 (en) * 2021-12-08 2023-06-15 Nanjing Zenshine Pharmaceuticals Co., Ltd. Fused heterocyclic compounds as pi3kalpha inhibitors
WO2024003241A1 (en) 2022-06-30 2024-01-04 Astrazeneca Ab Treatment for immuno-oncology resistant subjects with an anti pd-l1 antibody an antisense targeted to stat3 and an inhibitor of ctla-4
EP4602031A1 (en) * 2022-10-14 2025-08-20 Genesis Therapeutics, Inc. Methods for treating cancer
TW202506119A (zh) * 2023-08-02 2025-02-16 大陸商鄭州同源康醫藥有限公司 稠環類化合物及其用途

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004016607A1 (en) 2002-08-16 2004-02-26 Kinacia Pty Ltd. Inhibition of phosphoinositide 3-kinase beta

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6027A (en) * 1849-01-09 Rotary blacksmith s twyer
FI912995A0 (fi) 1988-12-21 1991-06-19 Upjohn Co Atiaterosklerotiska och antirombotiska 1-benzopyran-4-oner och 2-amino-1,3-benzoxazin-4-oner.
ATE158288T1 (de) 1990-06-20 1997-10-15 Upjohn Co Antiatherosklerotische und antithrombotische 1- benzopyran-4-on- und 2-amino-1,3-benzoxazin-4-on- derivate
DE4318756A1 (de) 1993-06-05 1994-12-08 Hoechst Ag Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
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
DE69709319T2 (de) 1996-03-05 2002-08-14 Astrazeneca Ab, Soedertaelje 4-anilinochinazolin derivate
GB9718972D0 (en) 1996-09-25 1997-11-12 Zeneca Ltd Chemical compounds
GB9714249D0 (en) 1997-07-08 1997-09-10 Angiogene Pharm Ltd Vascular damaging agents
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
CN1891699A (zh) 2000-01-24 2007-01-10 基纳西亚股份有限公司 用于治疗的吗啉代基取代的化合物
CN1431999A (zh) 2000-05-31 2003-07-23 阿斯特拉曾尼卡有限公司 具有血管损伤活性的吲哚衍生物
UA73993C2 (uk) 2000-06-06 2005-10-17 Астразенека Аб Хіназолінові похідні для лікування пухлин та фармацевтична композиція
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
RU2003103603A (ru) 2000-07-07 2004-08-20 Энджиоджен Фармасьютикалз Лимитед (Gb) Производные колхинола в качестве ингибиторов ангиогенеза
AR053358A1 (es) * 2005-04-15 2007-05-02 Cancer Rec Tech Ltd Inhibidores de adn - pk
AU2006303037A1 (en) 2005-10-21 2007-04-26 Merz Pharma Gmbh & Co Kgaa Chromenones and their use as modulators of metabotropic glutamate receptors
SI2004654T1 (sl) * 2006-04-04 2013-11-29 The Regents Of The University Of California Pirazolopirimidinski derivati za uporabo kot kinazni antagonisti
WO2008064244A2 (en) 2006-11-20 2008-05-29 The Trustees Of Columbia University In The City Of New York Phosphoinositide modulation for the treatment of neurodegenerative diseases
EP2112145A1 (en) 2008-04-24 2009-10-28 AxoGlia Therapeutics S.A. Chromenone derivatives useful for the treatment of neurodegenerative diseases
WO2010134082A1 (en) 2009-05-21 2010-11-25 Proteologics Ltd Chromenone derivatives for treatment of cancer
US8399460B2 (en) * 2009-10-27 2013-03-19 Astrazeneca Ab Chromenone derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004016607A1 (en) 2002-08-16 2004-02-26 Kinacia Pty Ltd. Inhibition of phosphoinositide 3-kinase beta
US20060276470A1 (en) 2002-08-16 2006-12-07 Jackson Shaun P Inhibition of phsphoinostide 3-dinase beta

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Journal of Medicinal Chemistry., 2005.01.27 Vol.48, No.2., pp 569-585

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021230733A1 (ko) * 2020-05-15 2021-11-18 제이투에이치바이오텍 주식회사 3원환 화합물 및 이의 의약 용도

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MX2012005027A (es) 2012-09-07
US20110098271A1 (en) 2011-04-28
SMT201500036B (it) 2015-05-05
DK2493870T3 (en) 2015-02-23
GT201200126A (es) 2014-03-03
CN104447657A (zh) 2015-03-25
KR20120098724A (ko) 2012-09-05
CN102712615A (zh) 2012-10-03
CL2012001056A1 (es) 2012-10-05
US9029374B2 (en) 2015-05-12
EP2493870A1 (en) 2012-09-05
EP2493870B1 (en) 2014-12-17
HRP20150146T1 (hr) 2015-05-22
JP5872016B2 (ja) 2016-03-01
EA020523B1 (ru) 2014-11-28
US20130158026A1 (en) 2013-06-20
AR078786A1 (es) 2011-11-30
US20140194419A1 (en) 2014-07-10
SI2493870T1 (sl) 2015-03-31
US20160272607A1 (en) 2016-09-22
JP5657010B2 (ja) 2015-01-21
CN104447657B (zh) 2016-08-17
PT2493870E (pt) 2015-02-18
CR20120217A (es) 2012-06-28
UA107474C2 (uk) 2015-01-12
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US9718800B2 (en) 2017-08-01
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BR112012010124B1 (pt) 2021-02-17
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US20160060240A1 (en) 2016-03-03
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