AU785385B2 - Novel derivatives and analogues of galanthamin - Google Patents

Novel derivatives and analogues of galanthamin Download PDF

Info

Publication number
AU785385B2
AU785385B2 AU42085/01A AU4208501A AU785385B2 AU 785385 B2 AU785385 B2 AU 785385B2 AU 42085/01 A AU42085/01 A AU 42085/01A AU 4208501 A AU4208501 A AU 4208501A AU 785385 B2 AU785385 B2 AU 785385B2
Authority
AU
Australia
Prior art keywords
mmol
nmr
sph
methoxy
treatment
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.)
Ceased
Application number
AU42085/01A
Other languages
English (en)
Other versions
AU4208501A (en
Inventor
Laszlo Czollner
Johannes Frohlich
Manfred Hirnschall
Ulrich Jordis
Beate Kalz
Matthias Treu
Stefan Welzig
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.)
Sanochemia Pharmazeutika AG
Original Assignee
Sanochemia Pharmazeutika AG
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 Sanochemia Pharmazeutika AG filed Critical Sanochemia Pharmazeutika AG
Publication of AU4208501A publication Critical patent/AU4208501A/en
Application granted granted Critical
Publication of AU785385B2 publication Critical patent/AU785385B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/28—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
    • 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
    • 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic 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
    • C07D491/02—Heterocyclic 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
    • C07D491/10—Spiro-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Psychology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Emergency Medicine (AREA)
  • Vascular Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Urology & Nephrology (AREA)
  • Cardiology (AREA)
  • Endocrinology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Furan Compounds (AREA)
AU42085/01A 2000-03-31 2001-03-22 Novel derivatives and analogues of galanthamin Ceased AU785385B2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
AT5462000 2000-03-31
AT546/2000 2000-03-31
AT2382001 2001-02-15
AT238/2001 2001-02-15
PCT/AT2001/000082 WO2001074820A1 (de) 2000-03-31 2001-03-22 Neue derivate und analoga von galanthamin

Publications (2)

Publication Number Publication Date
AU4208501A AU4208501A (en) 2001-10-15
AU785385B2 true AU785385B2 (en) 2007-03-29

Family

ID=25608130

Family Applications (1)

Application Number Title Priority Date Filing Date
AU42085/01A Ceased AU785385B2 (en) 2000-03-31 2001-03-22 Novel derivatives and analogues of galanthamin

Country Status (26)

Country Link
US (2) US7166588B2 (enExample)
EP (1) EP1181294B1 (enExample)
JP (1) JP2003529602A (enExample)
CN (1) CN1380883A (enExample)
AT (1) ATE263171T1 (enExample)
AU (1) AU785385B2 (enExample)
BG (1) BG65134B1 (enExample)
BR (1) BR0105563A (enExample)
CA (1) CA2368966A1 (enExample)
CZ (1) CZ300160B6 (enExample)
DE (1) DE50101827D1 (enExample)
DK (1) DK1181294T3 (enExample)
ES (1) ES2215885T3 (enExample)
HK (1) HK1049832A1 (enExample)
HU (1) HUP0202233A3 (enExample)
IS (1) IS2287B (enExample)
MX (1) MXPA01012275A (enExample)
NO (1) NO326458B1 (enExample)
NZ (1) NZ516302A (enExample)
PL (1) PL202463B1 (enExample)
PT (1) PT1181294E (enExample)
RU (1) RU2241001C2 (enExample)
SI (1) SI1181294T1 (enExample)
SK (1) SK285909B6 (enExample)
TR (1) TR200400857T4 (enExample)
WO (1) WO2001074820A1 (enExample)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4721386B2 (ja) * 2001-07-10 2011-07-13 第一三共株式会社 新規ガランタミン類縁体
WO2003080623A1 (de) * 2002-03-25 2003-10-02 Sanochemia Pharmazeutika Aktiengesellschaft Verfahren zur herstellung von norgalanthamin, ihren isomeren, salzen und hydraten
AT414125B (de) * 2003-09-29 2006-09-15 Sanochemia Pharmazeutika Ag Neue derivate des 4a,5,9,10,11,12-hexahydro- benzofuro(3a,3,2)(2) benzazepin, verfahren zu deren herstellung sowie deren verwendung zur herstellung von arzneimitteln
AT500143A1 (de) * 2004-04-22 2005-11-15 Sanochemia Pharmazeutika Ag Cholinesterase-inhibitoren in liposomen sowie deren herstellung und verwendung
US7877350B2 (en) * 2005-06-27 2011-01-25 Ab Initio Technology Llc Managing metadata for graph-based computations
ATE473219T1 (de) * 2005-09-22 2010-07-15 Galantos Pharma Gmbh Cholinerge enhancer mit verbesserter durchgängigkeit durch die blut-hirn-schranke zur behandlung von krankheiten, die mit kognitiven störungen einhergehen
US20090253654A1 (en) 2005-09-22 2009-10-08 Galantos Pharma Gmbh Cholinergic enhancers with improved blood-brain barrier permeability for the treatment of diseases accompanied by cognitive impairment
WO2008022365A2 (de) * 2006-08-24 2008-02-28 Sanochemia Ltd. Mittel zum beeinflussen der wirkungen von organophosphorverbindungen und verwendung von galanthamin, dessen derivaten und analoga zum herstellen solcher mittel
EP2137192B8 (en) 2008-04-14 2014-06-11 Neurodyn Life Sciences Inc. Derivatives of galantamine as pro-drugs for the treatment of human brain diseases
BG110141A (en) * 2008-05-23 2009-12-31 "Софарма" Ад GALANTAMINE DERIVATIVES, METHODS FOR THEIR PREPARATION AND USE
WO2011159759A1 (en) 2010-06-15 2011-12-22 Ab Initio Technology Llc Dynamically loading graph-based computations
WO2013160728A1 (en) 2012-04-26 2013-10-31 Alma Mater Studiorum - Universita' Di Bologna Dual targeting compounds for the treatment of alzheimer's disease
US10108521B2 (en) * 2012-11-16 2018-10-23 Ab Initio Technology Llc Dynamic component performance monitoring
SG11201604525TA (en) 2013-12-05 2016-07-28 Ab Initio Technology Llc Managing interfaces for dataflow graphs composed of sub-graphs
CN106687918B (zh) 2014-09-02 2020-08-28 起元科技有限公司 编译基于图的程序规范
SG11201701662XA (en) 2014-09-02 2017-04-27 Ab Initio Technology Llc Visually specifying subsets of components in graph-based programs through user interactions
US10657134B2 (en) 2015-08-05 2020-05-19 Ab Initio Technology Llc Selecting queries for execution on a stream of real-time data
US12006301B1 (en) 2021-05-13 2024-06-11 Florida A&M University And synthesis of dual 5-HT1A and 5-HT7 receptor ligands
CN116082352A (zh) * 2023-02-16 2023-05-09 西南交通大学 一种加兰他敏衍生物及其制备方法和用途
CN118908968B (zh) * 2024-10-09 2025-03-04 威胜生物医药(苏州)股份有限公司 一种加兰他敏中间体衍生物及其催化氧化制备方法
CN119528922B (zh) * 2024-11-22 2025-12-09 泰安汉威集团有限公司 一种氢溴酸加兰他敏关键杂质-氢溴酸表加兰他敏的手性合成方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2203183A1 (en) * 1994-10-21 1996-05-02 Laszlo Czollner Process for producing derivatives of 4a,5,9,10,11,12,-hexahydro-6h-benzofuro[3a,3,2-ef][2]benzazepine

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3947445A (en) 1974-05-09 1976-03-30 Stanford Research Institute Diazabicyclooctanes and diazabicycloheptanes
US4663318A (en) 1986-01-15 1987-05-05 Bonnie Davis Method of treating Alzheimer's disease
DE3856594D1 (de) 1987-05-04 2008-11-27 Bonnie Davis Mittel zur behandlung der alzheimer-krankheit
NL8800350A (nl) 1988-02-12 1989-09-01 Stichting Biomedical Research Synthetische galanthamine-derivaten, werkwijze voor het bereiden daarvan, en farmaceutische samenstellingen.
US4954502A (en) 1988-06-10 1990-09-04 Bristol-Myers Squibb Company 1-indolyalkyl-4-(substituted-pyridinyl)piperazines
US5336675A (en) 1991-05-14 1994-08-09 Ernir Snorrason Method of treating mania in humans
US5153193A (en) 1991-10-01 1992-10-06 Hoechst-Roussel Pharmaceuticals Incorporated Carbamate derivatives of 4-amino-3-isoxazolidinones, 3-amino-1-hydroxypyrrolidin-2-ones and 1-amino-1-cyclopropanecarboxylic acid analogs
US6323195B1 (en) 1993-10-15 2001-11-27 Aventis Pharmaceuticals Inc. Galanthamine derivatives as acetylcholinesterase inhibitors
US6323196B1 (en) 1993-10-15 2001-11-27 Aventis Pharmaceuticals Inc. Galanthamine derivatives as acetylcholinesterase inhibitors
US5428159A (en) 1994-04-08 1995-06-27 Ciba-Geigy Corporation Method of manufacture of (-)-galanthamine in high yield and purity substantially free of epigalanthamine
AT401058B (de) 1994-10-21 1996-06-25 Waldheim Pharmazeutika Gmbh Verfahren zum herstellen von derivaten des 4a,5, 9,10,11,12,-hexahydro-6h-benzofuro(3a,-3,2-ef) (2)benzazepins
US6407229B1 (en) 1994-10-21 2002-06-18 Sanochemia Pharmazeutika Ag Processes for the preparation of derivatives of 4a,5,9,10,11,12-hexahydro-6H-benzofuro-[3a,3,2-ef][2] benzazapine
GB9514821D0 (en) * 1995-07-19 1995-09-20 Sod Conseils Rech Applic Galanthamine derivatives
GB9519268D0 (en) 1995-09-21 1995-11-22 Chiroscience Ltd Preparation of alkaloids
AT403803B (de) 1996-04-19 1998-05-25 Sanochemia Ltd Neue benzazepinderivate, diese enthaltende arzneimittel und verwendung derselben zum herstellen von arzneimitteln
GB9716879D0 (en) * 1997-08-08 1997-10-15 Shire Int Licensing Bv Treatment of attention deficit disorders
AU1430099A (en) * 1998-12-01 2000-06-19 Sanochemia Pharmazeutika Aktiengesellschaft Use of galanthamine and galanthamine derivatives in the case of acute functionalbrain damage
AT414125B (de) 2003-09-29 2006-09-15 Sanochemia Pharmazeutika Ag Neue derivate des 4a,5,9,10,11,12-hexahydro- benzofuro(3a,3,2)(2) benzazepin, verfahren zu deren herstellung sowie deren verwendung zur herstellung von arzneimitteln

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2203183A1 (en) * 1994-10-21 1996-05-02 Laszlo Czollner Process for producing derivatives of 4a,5,9,10,11,12,-hexahydro-6h-benzofuro[3a,3,2-ef][2]benzazepine
US6043359A (en) * 1994-10-21 2000-03-28 Sanochemia Pharmazeutica Aktiengesellschaft Processes for the preparation of derivatives of 4a,5,9,10,11,12-hexahydro-6H-benzofuro-[3a,3,2-ef][2]benzazepine

Also Published As

Publication number Publication date
HK1045990A1 (en) 2002-12-20
IS2287B (is) 2007-10-15
SK17022001A3 (sk) 2003-02-04
EP1181294A1 (de) 2002-02-27
PL202463B1 (pl) 2009-06-30
CN1380883A (zh) 2002-11-20
BG65134B1 (bg) 2007-03-30
PL352638A1 (en) 2003-09-08
SK285909B6 (sk) 2007-10-04
MXPA01012275A (es) 2003-06-24
NO20015857L (no) 2002-01-29
DK1181294T3 (da) 2004-08-02
PT1181294E (pt) 2004-07-30
US7166588B2 (en) 2007-01-23
CZ20014178A3 (cs) 2002-11-13
NZ516302A (en) 2004-02-27
US20030199493A1 (en) 2003-10-23
CZ300160B6 (cs) 2009-02-25
DE50101827D1 (de) 2004-05-06
WO2001074820A1 (de) 2001-10-11
RU2241001C2 (ru) 2004-11-27
NO326458B1 (no) 2008-12-08
HUP0202233A3 (en) 2004-12-28
CA2368966A1 (en) 2001-10-11
BG106155A (en) 2002-08-30
BR0105563A (pt) 2002-04-02
ES2215885T3 (es) 2004-10-16
AU4208501A (en) 2001-10-15
JP2003529602A (ja) 2003-10-07
HUP0202233A2 (hu) 2002-11-28
NO20015857D0 (no) 2001-11-30
IS6174A (is) 2001-11-23
HK1049832A1 (zh) 2003-05-30
TR200400857T4 (tr) 2004-06-21
US20070027138A1 (en) 2007-02-01
SI1181294T1 (en) 2004-08-31
ATE263171T1 (de) 2004-04-15
EP1181294B1 (de) 2004-03-31

Similar Documents

Publication Publication Date Title
US20030199493A1 (en) Novel derivatives and analogues of galanthamin
JP7548814B2 (ja) Ｉｄｏ阻害剤および／またはｉｄｏ－ｈｄａｃ二重阻害剤としての多環式化合物
CA3246028A1 (en) KIF18A INHIBITOR
EP4472980A2 (en) Quinazoline pan-kras inhibitors
WO2004017908A2 (en) Calcium receptor modulating compound and use thereof
EP3224261B1 (en) Opioid receptor modulators
CN101235046B (zh) 长春碱衍生物、其制备方法和用途、以及包含该衍生物的药物组合物
CN111518110B (zh) 一种海鞘素化合物及其中间体的制备方法
WO1996030348A1 (en) Synthesis of bis-indolylmaleimides
MXPA98001179A (en) Isoquinolinas fused, novedosas as ligandos del receptor de dopam
CA2761287A1 (en) Synthesis of morphine and related derivatives
HU212579B (en) Process for producing 6-amino-octahydroindolizinetriol derivatives and pharmaceutical compositions containing the same
US20110124867A1 (en) Process and intermediates for the Synthesis of heterocyclic Substituted Piperazines with CXCR3 Antagonist Activity
Baldwin et al. Synthesis of bicyclic γ-lactams via oxazolidinones
Belov et al. An Easy Access to Bicyclic Peptides with an Octahydro [2H] pyrazino [1, 2‐a] pyrazine Skeleton
KR100768245B1 (ko) 신규한 갈란타민 유도체 및 유사체
HARADA et al. New Route to 1, 3, 3a, 8a-Tetrahydro-2H-benzofuro [2, 3-b] pyrrol-2-ones from Methyl α-Hydroxy-4H-1, 2-benzoxazine-4-acetates Obtained by Ring Transformation of 4-Aryl-2-isoxazoline 2-Oxides
Georgieva et al. Synthesis of 11H-4b, 10b-dihydro [1] benzopyrano [4, 3-c] isoquinoline-6, 11 (5H)-diones and 13H-6c, 12b-dihydronaphtho [1′, 2′: 5, 6]-pyrano [4-3c] isoquinoline-8, 13 (7H)-dione from homophthalic anhydride and N-(2-hydroxyarylidene) alkylamines
CA2607811A1 (en) Syntheses and preparations of narwedine and related novel compounds
EP0238226A1 (en) Substituted 1,3,4,9-tetrahydropyrano [3,4-b]indole-1-acetic acids
CN117088847A (zh) 一种并环化合物的制备、应用及用途
CN122029151A (zh) 他汀类衍生物及其使用方法
原田和穂 et al. Synthetic Reactions of Isoxazoline 2-oxides. Part XIV. New Route to 1, 3, 3a, 8a-Tetrahydro-2H-benzofuro (2, 3-b) pyrrol-2-ones from Methyl. ALPHA.-Hydroxy-4H-1, 2-benzoxazine-4-acetates Obtained by Ring Transformation of 4-Aryl-2-isoxazoline 2-Oxides.
HARADA et al. Transformation of 4-Aryl-2-isoxazoline 2-0xides”
JP2003183277A (ja) エピヒマンドラビン誘導体