WO1990009993A3 - Procede de synthese de l'huperzine a et ses analogues, et composes utiles dans cette synthese - Google Patents

Procede de synthese de l'huperzine a et ses analogues, et composes utiles dans cette synthese Download PDF

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Publication number
WO1990009993A3
WO1990009993A3 PCT/US1990/000925 US9000925W WO9009993A3 WO 1990009993 A3 WO1990009993 A3 WO 1990009993A3 US 9000925 W US9000925 W US 9000925W WO 9009993 A3 WO9009993 A3 WO 9009993A3
Authority
WO
WIPO (PCT)
Prior art keywords
huperzine
analogs
synthesis
compounds useful
fused ring
Prior art date
Application number
PCT/US1990/000925
Other languages
English (en)
Other versions
WO1990009993A2 (fr
Inventor
Alan P Kozikowski
Yan Xia
Original Assignee
Univ Pittsburgh
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 Univ Pittsburgh filed Critical Univ Pittsburgh
Priority to DK90904089T priority Critical patent/DK0460062T3/da
Priority to DE69033970T priority patent/DE69033970T2/de
Priority to CA002047744A priority patent/CA2047744C/fr
Priority to JP2504063A priority patent/JP2933386B2/ja
Priority to AT90904089T priority patent/ATE219061T1/de
Priority to EP90904089A priority patent/EP0460062B1/fr
Publication of WO1990009993A2 publication Critical patent/WO1990009993A2/fr
Publication of WO1990009993A3 publication Critical patent/WO1990009993A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La présente invention concerne un procédé de synthèse de certaines pyridines cycliques pontées fusionnées. De telles pyridines cycliques pontées fusionnées peuvent être converties en huperzine A et en analogues de l'huperzine A. La présente invention concerne également de telles pyridines cycliques pontées fusionnées, des composés utilisés pour la préparation des pyridines cycliques pontées fusionnées et des analogues de l'huperzine A.
PCT/US1990/000925 1989-02-21 1990-02-21 Procede de synthese de l'huperzine a et ses analogues, et composes utiles dans cette synthese WO1990009993A2 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
DK90904089T DK0460062T3 (da) 1989-02-21 1990-02-21 Huperzin A-analoger
DE69033970T DE69033970T2 (de) 1989-02-21 1990-02-21 Huperzin a analoge verbindungen
CA002047744A CA2047744C (fr) 1989-02-21 1990-02-21 Methode de synthese de l'huperzine a et de ses analogues et composes utilises pour ce faire
JP2504063A JP2933386B2 (ja) 1989-02-21 1990-02-21 ヒュペルジンａおよびその類似体の合成法およびその中で有用な化合物
AT90904089T ATE219061T1 (de) 1989-02-21 1990-02-21 Huperzin a analoge verbindungen
EP90904089A EP0460062B1 (fr) 1989-02-21 1990-02-21 Huperzine a analogues

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/313,118 US4929731A (en) 1989-02-21 1989-02-21 Method for the synthesis of huperzine A and analogs thereof and compounds useful therein
US313,118 1989-02-21

Publications (2)

Publication Number Publication Date
WO1990009993A2 WO1990009993A2 (fr) 1990-09-07
WO1990009993A3 true WO1990009993A3 (fr) 1990-11-01

Family

ID=23214460

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1990/000925 WO1990009993A2 (fr) 1989-02-21 1990-02-21 Procede de synthese de l'huperzine a et ses analogues, et composes utiles dans cette synthese

Country Status (10)

Country Link
US (1) US4929731A (fr)
EP (3) EP1026157B1 (fr)
JP (1) JP2933386B2 (fr)
AT (3) ATE219061T1 (fr)
CA (2) CA2296915A1 (fr)
DE (3) DE69034226T2 (fr)
DK (2) DK1167354T3 (fr)
ES (2) ES2194003T3 (fr)
HK (1) HK1030604A1 (fr)
WO (1) WO1990009993A2 (fr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5177082A (en) * 1985-11-05 1993-01-05 Yu Chao Mei Huperzines and analogs
US5104880A (en) * 1991-05-01 1992-04-14 Mayo Foundation For Medical Education And Research Huperzine a analogs as acetylcholinesterase inhibitors
US5206393A (en) * 1991-09-30 1993-04-27 Union Carbide Chemicals & Plastics Technology Corporation Oxa-bicyclic polyfunctional compounds and preparation thereof
US5145973A (en) * 1991-09-30 1992-09-08 Union Carbide Chemicals & Plastics Technology Corporation Oxa-Bicyclic polyfunctional compounds and preparation thereof
US5547960A (en) * 1994-09-07 1996-08-20 Mayo Foundation For Medical Education And Research C-10 analogs of huperzine a
USRE38460E1 (en) 1994-12-28 2004-03-09 Shanghai Institute Of Materia Medica Chinese Academy Of Sciences Huperzine A derivatives, their preparation and their use
CN1125725A (zh) * 1994-12-28 1996-07-03 中国科学院上海药物研究所 一类海克林碱衍生物及它的用途
AU6053900A (en) * 1999-06-25 2001-01-31 Morris Notelovitz Compositions for treating or preventing neurodegeneration and cognitive decline
US6271379B1 (en) 2000-03-08 2001-08-07 Georgetown University Intermediates useful for the synthesis of huperzine A
US6436972B1 (en) 2000-04-10 2002-08-20 Dalhousie University Pyridones and their use as modulators of serine hydrolase enzymes
US6369052B1 (en) 2000-08-07 2002-04-09 Georgetown University Combination of huperzine and nicotinic compounds as a neuroprotective agent
KR100390777B1 (ko) * 2000-12-19 2003-07-10 한국화학연구원 피리돈 유도체의 제조방법
US6967206B2 (en) 2002-12-05 2005-11-22 Access Business Group International Llc Compositions and methods for increasing growth hormone levels
US20060264455A1 (en) * 2005-05-23 2006-11-23 Schachter Steven C Use of huperzine for disorders
US8097726B2 (en) * 2006-05-17 2012-01-17 Industrial Technology Research Institute Huperzine a compound for treatment of alzheimer's disease
WO2009120774A2 (fr) * 2008-03-25 2009-10-01 Debiopharm S.A. Procédé de préparation d'huperzine a et des dérivés de celle-ci
WO2010028134A2 (fr) * 2008-09-04 2010-03-11 President And Fellows Of Harvard College Traitement de troubles neurologiques à l'aide d'huperzine
CN104496900A (zh) * 2014-12-15 2015-04-08 陕西嘉禾植物化工有限责任公司 一种2-甲氧基-6-酮-5,7,8-三氢-喹啉的制备方法
CN104496998B (zh) * 2014-12-15 2017-07-11 陕西嘉禾生物科技股份有限公司 一种1′‑苄基‑2′‑酮‑5′，7′，8′‑三氢‑螺‑[1，3‑二氧五环‑2]‑喹啉的制备方法
CN109705038B (zh) * 2017-10-25 2020-11-03 广州市朗启医药科技有限责任公司 石杉碱甲的合成方法
CN114716449B (zh) * 2022-04-12 2023-09-29 浙江工业大学 一种2-甲氧基-6-乙二醇缩酮-5,7,8-三氢喹啉的制备方法

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
Acta Pharmaceutica Sinica Vol. 22, #11, CHEN, et al. "The Effect of Fordine on Learning and Memory in Rats" pp. 801-806 1987 see Abstract. *
Acta Pharmacologica Sinica Vol. 9, #3, WANG, et al. "Pharmacokinetics of huperzine A in rats and mice" pp. 193-196 1988 see Abstract. *
Canadian Journal of Chemistry Vol. 62, GRAVEL, et al. "Total regiospecific synthesis of the sclagine tricyclic ring system" pp. 2945-2847 1984 see synthesis diagrams. *
Canadian Journal of Chemistry, Vol. 64, LIU, et al. "The structures of huperzine A and B...." pp. 837-839 1986 see full document. *
CHEMICAL ABSTRACTS Vol. 101, 1984 of Tai-Wan Yao Hsueh Tsu Chih Vol. 36, 1984 CHEN, et al. "Studies on the bioactive lycopodium alkaloid-the structure and activity of isoselagine from lycopodium serratum var. longipetiolatum". Abstract No. 101:143940W. *
CHEMICAL ABSTRACTS Vol. 106, 1987 of Zhongguo Yaoli Xuebau Vol. 7 No. 6 1986 TANG, et al. "Effects of huperzine A on learning and retrieval process of discrimination performance in rats" Abstracts No. 106:12878n. *
CHEMICAL ABSTRACTS Vol. 107, 1987 of Huaxue Xuebao Vol. 44 No. 10 1986 LIU, et al. "Chemistry of huperzine A B" Abstract No. 107:115821p see full Abstract. *
CHEMICAL ABSTRACTS Vol. 86, 1977 of Bull. Soc. Chim. Belg. Vol. 85, No. 8 1976 NYAMBO, et al. "Alkaloids of lycopodium gnidioides and lycopodium verticillatum" Abstract No. 86:90108u. *
Heterocycles Vol. 21, No. 1, 1984 KENDE, et al. "New tactics in Heterocyclic Synthesis" pp. 91-106. See bottom of p. 101-p. 104. *

Also Published As

Publication number Publication date
EP1167354A2 (fr) 2002-01-02
CA2047744C (fr) 2000-05-02
EP1026157B1 (fr) 2006-06-21
US4929731A (en) 1990-05-29
DE69034226D1 (de) 2006-08-03
HK1030604A1 (en) 2001-05-11
EP1167354B1 (fr) 2003-05-07
DE69034226T2 (de) 2007-06-21
EP0460062B1 (fr) 2002-06-12
EP1026157A3 (fr) 2004-08-11
DE69033970D1 (de) 2002-07-18
DE69033970T2 (de) 2002-10-02
CA2047744A1 (fr) 1990-08-22
EP1026157A2 (fr) 2000-08-09
WO1990009993A2 (fr) 1990-09-07
DK0460062T3 (da) 2002-08-26
EP0460062A4 (en) 1992-07-01
EP1167354A3 (fr) 2002-01-09
DE69034070D1 (de) 2003-06-12
JP2933386B2 (ja) 1999-08-09
DK1167354T3 (da) 2003-09-01
ATE219061T1 (de) 2002-06-15
EP0460062A1 (fr) 1991-12-11
ES2194003T3 (es) 2003-11-16
ES2173858T3 (es) 2002-11-01
CA2296915A1 (fr) 1990-08-22
DE69034070T2 (de) 2003-12-18
ATE330943T1 (de) 2006-07-15
ATE239709T1 (de) 2003-05-15

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