CA2837549A1 - Hyperforin analogs, methods of synthesis, and uses thereof - Google Patents

Hyperforin analogs, methods of synthesis, and uses thereof Download PDF

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Publication number
CA2837549A1
CA2837549A1 CA2837549A CA2837549A CA2837549A1 CA 2837549 A1 CA2837549 A1 CA 2837549A1 CA 2837549 A CA2837549 A CA 2837549A CA 2837549 A CA2837549 A CA 2837549A CA 2837549 A1 CA2837549 A1 CA 2837549A1
Authority
CA
Canada
Prior art keywords
optionally substituted
membered heteroaryl
alkyl
membered heterocyclyl
alkynyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA2837549A
Other languages
English (en)
French (fr)
Inventor
Matthew D. Shair
Brian A. Sparling
David MOEBIUS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Harvard University
Original Assignee
Harvard University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Harvard University filed Critical Harvard University
Publication of CA2837549A1 publication Critical patent/CA2837549A1/en
Abandoned legal-status Critical Current

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    • 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
    • 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
    • C07C49/703—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
    • 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
    • C07C49/743—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

Landscapes

  • 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)
CA2837549A 2011-06-03 2012-06-01 Hyperforin analogs, methods of synthesis, and uses thereof Abandoned CA2837549A1 (en)

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 (1)

Publication Number Publication Date
CA2837549A1 true CA2837549A1 (en) 2012-12-06

Family

ID=47260359

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2837549A Abandoned CA2837549A1 (en) 2011-06-03 2012-06-01 Hyperforin analogs, methods of synthesis, and uses thereof

Country Status (13)

Country Link
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)

* Cited by examiner, † Cited by third party
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

Family Cites Families (7)

* 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
IT1301679B1 (it) * 1998-06-10 2000-07-07 Indena Spa Derivati dell'iperforina, loro uso e formulazioni che licontengono.
AU3744100A (en) * 1999-03-15 2000-10-04 Shaman Pharmaceuticals, Inc. Bicyclo(3.3.1)nonenes useful for the treatment of diabetes
AU3738700A (en) * 1999-03-15 2000-10-04 Shaman Pharmaceuticals, Inc. Stabilized bicyclo(3.3.1)nonenes and methods of use
DE10157033A1 (de) * 2001-11-21 2003-05-28 Siegfried Seeber Substituierte Bicyclo[3.3.1]nonan-2,4,9-trione als pharmazeutische Wirkstoffe
ITMI20020872A1 (it) 2002-04-23 2003-10-23 Indena Spa Derivati dell'iperforina loro uso e formulazioni che li contengono
ITMI20020871A1 (it) 2002-04-23 2003-10-23 Indena Spa Derivati alogenati dell'iperforina loro uso e formulazioni che li contengono

Also Published As

Publication number Publication date
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
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
JP2014527508A (ja) 2014-10-16
IL229742A0 (en) 2014-01-30

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Legal Events

Date Code Title Description
FZDE Discontinued

Effective date: 20180601