JP2014527508A - ハイパーフォリン類似物、合成方法、およびその使用 - Google Patents

ハイパーフォリン類似物、合成方法、およびその使用 Download PDF

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JP2014527508A
JP2014527508A JP2014513726A JP2014513726A JP2014527508A JP 2014527508 A JP2014527508 A JP 2014527508A JP 2014513726 A JP2014513726 A JP 2014513726A JP 2014513726 A JP2014513726 A JP 2014513726A JP 2014527508 A JP2014527508 A JP 2014527508A
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JP2014527508A5 (enExample
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シェア,マシュー,ディー.
スパーリング,ブライアン,エー.
メビウス,デビット
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Harvard University
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
    • C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
    • C07C49/733—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system having two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/743—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups having unsaturation outside the rings, e.g. humulones, lupulones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/46—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing nine carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Pulmonology (AREA)
  • Psychology (AREA)
  • Psychiatry (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Emergency Medicine (AREA)
  • Hematology (AREA)
  • Hospice & Palliative Care (AREA)
  • Anesthesiology (AREA)
  • Vascular Medicine (AREA)
  • Dermatology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Endocrinology (AREA)
  • Rheumatology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Epoxy Compounds (AREA)
JP2014513726A 2011-06-03 2012-06-01 ハイパーフォリン類似物、合成方法、およびその使用 Pending JP2014527508A (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161493250P 2011-06-03 2011-06-03
US61/493,250 2011-06-03
PCT/US2012/040379 WO2012167021A2 (en) 2011-06-03 2012-06-01 Hyperforin analogs, methods of synthesis, and uses thereof

Publications (2)

Publication Number Publication Date
JP2014527508A true JP2014527508A (ja) 2014-10-16
JP2014527508A5 JP2014527508A5 (enExample) 2015-08-20

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JP2014513726A Pending JP2014527508A (ja) 2011-06-03 2012-06-01 ハイパーフォリン類似物、合成方法、およびその使用

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US (1) US9321713B2 (enExample)
EP (1) EP2714638A4 (enExample)
JP (1) JP2014527508A (enExample)
KR (1) KR20140041610A (enExample)
CN (1) CN103732568A (enExample)
AU (1) AU2012262084A1 (enExample)
BR (1) BR112013030986A2 (enExample)
CA (1) CA2837549A1 (enExample)
IL (1) IL229742A0 (enExample)
MX (1) MX2013014162A (enExample)
RU (1) RU2013157954A (enExample)
SG (1) SG195210A1 (enExample)
WO (1) WO2012167021A2 (enExample)

Families Citing this family (6)

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Publication number Priority date Publication date Assignee Title
CN103980231B (zh) * 2014-06-04 2016-03-30 中国科学院上海有机化学研究所 一种五氟苯基环氧丙烷的合成方法
US20180071269A1 (en) 2015-08-12 2018-03-15 Tianxin Wang Therapeutical methods, formulations and nutraceutical formulations
CN106496171B (zh) * 2016-10-20 2019-09-13 贵州省中国科学院天然产物化学重点实验室 具有抗肿瘤活性的多环多异戊烯基间苯三酚类化合物、其制备方法及应用
CN106967016B (zh) * 2017-04-25 2020-05-19 华中科技大学 贯叶连翘次生代谢产物中具有乙酰胆碱酯酶抑制作用化合物及分离制备和用途
CN109044999A (zh) * 2018-10-15 2018-12-21 上海市第六人民医院 贯叶金丝桃素在制备促进白色脂肪棕色化并且提高棕色脂肪活性的药物中的用途
DE102022129895A1 (de) * 2022-11-11 2024-05-16 Technische Universität Dresden, Körperschaft des öffentlichen Rechts 4-Hydroxybicyclo[3.3.1]non-3-en-2,9-dion-Derivate und deren Verwendung

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000054785A2 (en) * 1999-03-15 2000-09-21 Shaman Pharmaceuticals, Inc. Stabilized bicyclo[3.3.1]nonenes and methods of use
WO2000054760A2 (en) * 1999-03-15 2000-09-21 Shaman Pharmaceuticals, Inc. Bicyclo (3.3.1) nonenes useful for the treatment of diabetes and hypertriglyceridemia
JP2002517478A (ja) * 1998-06-10 2002-06-18 インデナ エッセ ピ ア ハイパーフォリン誘導体、その利用及びこれを含む調剤
JP2005515979A (ja) * 2001-11-21 2005-06-02 ゼーバー,ジークフリート 活性な薬物成分としてのビシクロ[3.3.1]ノナン−2,4,9−トリオン置換体
JP2005523917A (ja) * 2002-04-23 2005-08-11 インデナ・ソチエタ・ペル・アチオニ ハイパーフォリン誘導体、それらの使用及びそれらを含有している製剤

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999041220A1 (de) 1998-02-13 1999-08-19 Dr. Willmar Schwabe Gmbh & Co. Stabile hyperforin-salze, verfahren zu ihrer herstellung und verwendung zur therapie der alzheimerschen krankheit
ITMI20020871A1 (it) 2002-04-23 2003-10-23 Indena Spa Derivati alogenati dell'iperforina loro uso e formulazioni che li contengono

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002517478A (ja) * 1998-06-10 2002-06-18 インデナ エッセ ピ ア ハイパーフォリン誘導体、その利用及びこれを含む調剤
WO2000054785A2 (en) * 1999-03-15 2000-09-21 Shaman Pharmaceuticals, Inc. Stabilized bicyclo[3.3.1]nonenes and methods of use
WO2000054760A2 (en) * 1999-03-15 2000-09-21 Shaman Pharmaceuticals, Inc. Bicyclo (3.3.1) nonenes useful for the treatment of diabetes and hypertriglyceridemia
JP2005515979A (ja) * 2001-11-21 2005-06-02 ゼーバー,ジークフリート 活性な薬物成分としてのビシクロ[3.3.1]ノナン−2,4,9−トリオン置換体
JP2005523917A (ja) * 2002-04-23 2005-08-11 インデナ・ソチエタ・ペル・アチオニ ハイパーフォリン誘導体、それらの使用及びそれらを含有している製剤

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
Title
JPN6015049541; Ma, Shuang-Gang et al.: 'Prenylated C6-C3 compounds with molecular diversity from the roots of Illicium oligandrum' Phytochemistry (Elsevier) 72(1), 2011, 115-125 *
JPN6015049542; Tang, Wen-Zhao et al.: 'Rearranged prenylated C6-C3 compounds and a highly oxygenated seco-prezizaane-type sesquiterpene fro' Journal of Natural Products 72(6), 2009, 1017-1021 *
JPN6015049544; Ahmad, Nadia M. et al.: 'Synthetic studies towards garsubellin A: Synthesis of model systems and potential mimics by regiosel' Organic & Biomolecular Chemistry 5(12), 2007, 1924-1934 *
JPN6015049546; Hashida, Koh; Ohara, Seiji; Makino, Rei: 'Base-catalyzed reactions of procyanidin B3: Formation of a novel catechinic acid-catechin dimer' Journal of Wood Chemistry and Technology 26(2), 2006, 125-140 *
JPN6015049547; Hashida, Koh; Ohara, Seiji; Makino, Rei: 'Base-Catalyzed Reactions of (-)-Epicatechin: Formation of Enantiomers of Base-Catalyzed Reaction Pro' Journal of Wood Chemistry and Technology 23(3 & 4), 2003, 227-232 *
JPN6015049548; Hashida, Koh; Ohara, Seiji: 'Formation of a novel catechinic acid stereoisomer from base-catalyzed reactions of (+)-catechin' Journal of Wood Chemistry and Technology 22(1), 2002, 11-23 *
JPN6015049549; Ohara, Seiji; Hemingway, Richard W.: 'Condensed tannins: the formation of a diarylpropanol-catechinic acid dimer from base-catalyzed reac' Journal of Wood Chemistry and Technology 11(2), 1991, 195-208 *
JPN6015049550; Inouye, Yoshinobu; Kojima, Tsutomu; Owada, Jun; Kakisawa, Hiroshi: 'Preparation of bicyclo[3.3.1]nonane-2,4-dione derivatives' Bulletin of the Chemical Society of Japan 60(12), 1987, 4369-75 *
JPN6015049551; Gravel, D.; Rahal, S.: 'New access to noradamantanes via generation of selectively protected bicyclic beta-diketones' Canadian Journal of Chemistry 53(17), 1975, 2671-3 *
JPN6015049552; Simpkins, Nigel S. et al.: 'Synthesis of nemorosone via a difficult bridgehead substitution reaction' Synlett (4), 2010, 639-643 *
JPN6015049553; Kraus, George A.; Nguyen, Tuan H.; Jeon, Insik: 'Synthesis of the core bicyclic system of hyperforin and nemorosone' Tetrahedron Letters 44(4), 2003, 659-661 *
JPN6015049554; Aredova, E. N. et al.: 'Derivatives of bicyclo[3.3.1]nonane-2,9-dione' Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (6), 1976, 1408-10 *

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MX2013014162A (es) 2014-09-08
AU2012262084A1 (en) 2014-01-09
BR112013030986A2 (pt) 2016-12-06
US9321713B2 (en) 2016-04-26
EP2714638A2 (en) 2014-04-09
CN103732568A (zh) 2014-04-16
RU2013157954A (ru) 2015-07-20
CA2837549A1 (en) 2012-12-06
US20140135287A1 (en) 2014-05-15
WO2012167021A2 (en) 2012-12-06
KR20140041610A (ko) 2014-04-04
SG195210A1 (en) 2013-12-30
EP2714638A4 (en) 2015-09-23
WO2012167021A3 (en) 2013-04-25
IL229742A0 (en) 2014-01-30

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