FI108723B - Förfarande för framställning av 6-esterderivat av terapeutiskt avändbara 4a,5,9,10,11,12-hexahydro-11-metyl-6H-bensofuro[3a,3,2-ef][2]bensazepin-3,6-diol - Google Patents
Förfarande för framställning av 6-esterderivat av terapeutiskt avändbara 4a,5,9,10,11,12-hexahydro-11-metyl-6H-bensofuro[3a,3,2-ef][2]bensazepin-3,6-diol Download PDFInfo
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- FI108723B FI108723B FI944821A FI944821A FI108723B FI 108723 B FI108723 B FI 108723B FI 944821 A FI944821 A FI 944821A FI 944821 A FI944821 A FI 944821A FI 108723 B FI108723 B FI 108723B
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- 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
- C07D491/04—Ortho-condensed systems
-
- 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
-
- 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
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- 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
- C07D491/06—Peri-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (4)
1. Förfarande för framställning av terapeutiskt användbara 6-esterderivat av 4a,5,9,10,11,12-hexahydro-11-5 metyl-6H-bensofuro[3a,3,2-ef][2]bensazepin-3,6-diol eller farmaceutiskt godtagbara salter därav, OR2 JL o .OH ra> V CH3 15 där R2 är (C3-C6) alkenylkarbonyl, (C3-C8) cykloalkyl- karbonyl, (C3-C8) cykloalkylarainokarbonyl, (C3-C6) alkynyl- karbonyl, (C3-C6) cykloalkyl-(C-l-C.^) alkylkarbonyl, adaman-tylkarbonyl, adamantylmetylkarbonyl, pyridyl, tetrahydro- 20 isokinolylkarbonyl, morfolinokarbonyl, halogen(C1-C6)alkyl-sulfonyl eller (C^-Cg) alkylsilyl, * ' kännetecknat därav, att | (a) galantamin med formeln (III) 25 ch,o :i' rV°vVH
30 N-^ / ch3 O-demetyleras, varvid erhälls en förening med formeln (IV) 35 37 1 08723 OH 0γ0τύ: N—^ CH3 io (b) om sä önskas, omsätts föreningen, som har for- meln (IV), med ett lämpligt cykloalkylisocyanat, varvid erhälls en förening med formeln (II) , där R2 är (C3-C8) cykloalkylaminokarbonyl, (c) om sd önskas, omsätts föreningen, som har for-15 mein (IV), med en lämplig karboxylsyrahalogenid, varvid ! erhälls en förening med formeln (II) , där R är (C3-C8) alkenylkarbonyl, (C3-C6) alkynylkarbonyl eller (C3 -C8) cykloalkylkarbonyl, (d) om sd önskas, omsätts föreningen, som har for-20 mein (IV), med ett lämpligt halogenpyridin, varvid erhälls en förening med formeln (II), där R2 är pyridyl, (e) om sä önskas, omsätts föreningen, som har for- , ; mein (IV), med en lämplig alkylsilylhalogenid, varvid er- . / hälls en förening med formeln (II) , där R2 är (C^-Cg) - l 25 alkylsilyl, *·*; (f) om sä önskas, omsätts föreningen, som har for- • · · ·*·: mein (IV) , med en lämplig sulfonsyraanhydrid, varvid er- halls en förening med formeln (II) , där R2 är halogen- (Οχ - Cs) alkylsulf onyl, 30 (g) om sä önskas, omsätts föreningen, som har for- ”*: mein (IV), med ett lämpligt koppi ingsmedel, säsom 1,1- . karbonyldiimidazol eller dicyklohexyldikarbodiimid, ooh en ‘ ; lämplig karboxylsyra, tetrahydroisokinolin eller morfolin, varvid erhälls en förening med formeln (II), där R2 är 35 (C3-C8) cykloalkylkarbonyl, adamantylkarbonyl, adamantyl- metylkarbonyl, tetrahydroisokinolylkarbonyl eller morfo-linokarbonyl. 33 1 08723
2. Förfarande enligt patentkrav 1, kanne- t e c k n a t därav, att man framställer en förening med formeln (II), där R2 är (C3_6)-alkenylkarbonyl, (C3_6) - alkynylkarbonyl, (C3_8) -cykloalkylkarbonyl, (C3.8)-cykloal- 5 kyl-(C1_12) -alkylkarbonyl, pyridyl, morfolinokarbonyl eller tetrahydroisokinolylkarbonyl.
3. Förfarande enligt patentkrav 1, kanne-t e c k n a t därav, att man framställer en förening med formeln (II), där R2 är cyklopropylkarbonyl, cyklobutyl- 10 karbonyl, cyklohexylkarbonyl, metylcyklohexylkarbonyl, adamantylmetylkarbonyl, 2-metylpropenylkarbonyl, 2- propynylkarbonyl, cykloheptylaminokarbonyl, cyklohexyl-aminokarbonyl, morfolinokarbonyl eller tetrahydroisokino-linylkarbonyl. 15
4. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att man framställer (6-O-demetyl)-6-0-(1,2,3,4-tetrahydroisokinolin-2-yl)karbonylgalantamin eller ett farmaceutiskt godtagbart syraadditiossalt därav. ϊ * ! * * • · * t f \ t » * I t t · · » ! I » M M | »
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13744093 | 1993-10-15 | ||
| US08/137,440 US6323195B1 (en) | 1993-10-15 | 1993-10-15 | Galanthamine derivatives as acetylcholinesterase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI944821A0 FI944821A0 (sv) | 1994-10-13 |
| FI944821A FI944821A (sv) | 1995-04-16 |
| FI108723B true FI108723B (sv) | 2002-03-15 |
Family
ID=22477446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI944821A FI108723B (sv) | 1993-10-15 | 1994-10-13 | Förfarande för framställning av 6-esterderivat av terapeutiskt avändbara 4a,5,9,10,11,12-hexahydro-11-metyl-6H-bensofuro[3a,3,2-ef][2]bensazepin-3,6-diol |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US6323195B1 (sv) |
| EP (2) | EP0653427B1 (sv) |
| JP (1) | JP2664344B2 (sv) |
| KR (1) | KR0169114B1 (sv) |
| CN (1) | CN1039911C (sv) |
| AT (1) | ATE212348T1 (sv) |
| AU (1) | AU696249B2 (sv) |
| CA (1) | CA2118174C (sv) |
| CZ (1) | CZ287071B6 (sv) |
| DE (1) | DE69429708T2 (sv) |
| DK (1) | DK0653427T3 (sv) |
| EG (1) | EG20472A (sv) |
| ES (1) | ES2171428T3 (sv) |
| FI (1) | FI108723B (sv) |
| IL (1) | IL111274A (sv) |
| NO (1) | NO310415B1 (sv) |
| NZ (1) | NZ264683A (sv) |
| PL (1) | PL177730B1 (sv) |
| PT (1) | PT653427E (sv) |
| RO (1) | RO114133B1 (sv) |
| RU (1) | RU2114850C1 (sv) |
| TW (1) | TW363969B (sv) |
| ZA (1) | ZA948062B (sv) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9514821D0 (en) * | 1995-07-19 | 1995-09-20 | Sod Conseils Rech Applic | Galanthamine derivatives |
| AT403803B (de) | 1996-04-19 | 1998-05-25 | Sanochemia Ltd | Neue benzazepinderivate, diese enthaltende arzneimittel und verwendung derselben zum herstellen von arzneimitteln |
| WO2000030446A1 (en) * | 1998-11-23 | 2000-06-02 | Bonnie Davis | Dosage formulations for acetylcholinesterase inhibitors |
| CA2358062C (en) | 1998-12-24 | 2006-12-19 | Janssen Pharmaceutica N.V. | Controlled release galantamine composition |
| ATE355066T1 (de) * | 1999-01-11 | 2006-03-15 | Atanas Russinov Djananov | Nahrungszusatz aus kräutern zur steigerung der muskulären kraft und ausdauer von athleten |
| US8603546B2 (en) * | 1999-01-11 | 2013-12-10 | Herbaceuticals Inc. | Herbal supplement for increased muscle strength and endurance for athletes |
| US6372760B1 (en) * | 1999-03-31 | 2002-04-16 | Eisai Co., Ltd. | Stabilized composition comprising antidementia medicament |
| BR0015025A (pt) * | 1999-10-26 | 2002-06-18 | Janssen Pharmaceutica Nv | Solução oral contendo galantamina e um agente adoçante |
| US6670356B2 (en) | 1999-12-10 | 2003-12-30 | Bonnie Davis | Analogs of galanthamine and lycoramine as modulators of nicotinic receptors |
| DE50101827D1 (de) | 2000-03-31 | 2004-05-06 | Sanochemia Pharmazeutika Ag Wi | Neue derivate und analoga von galanthamin |
| US20030162770A1 (en) * | 2002-02-22 | 2003-08-28 | Davis Bonnie M. | Use of modulators of nicotinic receptors for treatment of cognitive dysfunction |
| US20050143350A1 (en) * | 2003-11-19 | 2005-06-30 | Seed John C. | Combination drug therapy to treat obesity |
| WO2005065661A2 (en) * | 2003-12-31 | 2005-07-21 | Actavis Group Hf | Immediate, controlled and sustained release formulations of galanthamine |
| CA2552114A1 (en) * | 2003-12-31 | 2005-07-21 | Actavis Group Hf | Solid dosage formulations of galantamine |
| US20080045500A1 (en) * | 2004-07-01 | 2008-02-21 | Eisai R&D Management Co., Ltd. | Nerve Regeneration Stimulator |
| PL1895994T3 (pl) * | 2005-05-13 | 2011-02-28 | Alza Corp | Wielowarstwowy system podawania leków z barierą zabezpieczającą przed wypływaniem materiału ze zbiornika |
| US20080188510A1 (en) * | 2005-05-23 | 2008-08-07 | Eisai R & D Management Co., Ltd. | Novel methods using zonisamide |
| 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 |
| EP1777222A1 (en) | 2005-09-22 | 2007-04-25 | Galantos Pharma GmbH | Cholinergic enhancers with improved blood-brain barrier permeability for the treatment of diseases accompanied by cognitive impairment |
| 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 |
| WO2007035941A2 (en) * | 2005-09-23 | 2007-03-29 | Alza Corporation | Transdermal galantamine delivery system |
| CN102007129B (zh) | 2008-04-14 | 2014-05-07 | 神经动力生命科学公司 | 用作治疗人类脑疾病的前药的雪花胺衍生物 |
| US20120184532A1 (en) * | 2009-07-23 | 2012-07-19 | Shire Llc | Galantamine amino acid and peptide prodrugs and uses thereof |
| WO2013160728A1 (en) | 2012-04-26 | 2013-10-31 | Alma Mater Studiorum - Universita' Di Bologna | Dual targeting compounds for the treatment of alzheimer's disease |
| EP3628315A1 (en) | 2018-09-28 | 2020-04-01 | Université de Caen Normandie | Combination of acetylcholinesterase inhibitor and 5-ht4 receptor agonist as neuroprotective agent in the treatment of neurodegenerative diseases |
| CN113292420A (zh) * | 2021-05-27 | 2021-08-24 | 神隆医药（常熟）有限公司 | 加兰他敏中间体原料2-溴-5-羟基-4-甲氧基苯甲酸回收方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL122665B1 (en) | 1978-11-21 | 1982-08-31 | Edinen Zentar Chim | Process for preparing novel dienones of narvedine type and their derivatives |
| US4663318A (en) | 1986-01-15 | 1987-05-05 | Bonnie Davis | Method of treating Alzheimer's disease |
| US6150354A (en) * | 1987-01-15 | 2000-11-21 | Bonnie Davis | Compounds for the treatment of Alzheimer's disease |
| ATE411026T1 (de) * | 1987-05-04 | 2008-10-15 | 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. |
| EP0515301A3 (en) | 1991-05-14 | 1993-06-16 | Ernir Snorrason | Improvements in benzodiazepine treatment by cholinesterterase inhibitors |
| US5231093A (en) * | 1991-10-01 | 1993-07-27 | Hoechst-Roussel Pharmaceuticals Incorporated | Carbamate derivatives of 4-amino-3-isoxazolidinones, 3-amino-1-hydroxypyrrolidin-2-ones and 1-amino-1-cyclopropanecarboxylic acid analogs |
| 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 |
-
1993
- 1993-10-15 US US08/137,440 patent/US6323195B1/en not_active Expired - Lifetime
-
1994
- 1994-10-10 EP EP94115959A patent/EP0653427B1/en not_active Expired - Lifetime
- 1994-10-10 AT AT94115959T patent/ATE212348T1/de active
- 1994-10-10 DE DE69429708T patent/DE69429708T2/de not_active Expired - Lifetime
- 1994-10-10 DK DK94115959T patent/DK0653427T3/da active
- 1994-10-10 PT PT94115959T patent/PT653427E/pt unknown
- 1994-10-10 ES ES94115959T patent/ES2171428T3/es not_active Expired - Lifetime
- 1994-10-10 EP EP00107570A patent/EP1020470A3/en not_active Withdrawn
- 1994-10-13 IL IL11127494A patent/IL111274A/xx not_active IP Right Cessation
- 1994-10-13 FI FI944821A patent/FI108723B/sv not_active IP Right Cessation
- 1994-10-13 EG EG64194A patent/EG20472A/xx active
- 1994-10-13 NZ NZ264683A patent/NZ264683A/en not_active IP Right Cessation
- 1994-10-13 RU RU94036448A patent/RU2114850C1/ru active
- 1994-10-14 TW TW083109526A patent/TW363969B/zh not_active IP Right Cessation
- 1994-10-14 ZA ZA948062A patent/ZA948062B/xx unknown
- 1994-10-14 CZ CZ19942546A patent/CZ287071B6/cs not_active IP Right Cessation
- 1994-10-14 AU AU75814/94A patent/AU696249B2/en not_active Expired
- 1994-10-14 KR KR1019940026303A patent/KR0169114B1/ko active IP Right Grant
- 1994-10-14 PL PL94305456A patent/PL177730B1/pl unknown
- 1994-10-14 RO RO94-01669A patent/RO114133B1/ro unknown
- 1994-10-14 CA CA002118174A patent/CA2118174C/en not_active Expired - Lifetime
- 1994-10-14 NO NO19943893A patent/NO310415B1/no not_active IP Right Cessation
- 1994-10-14 CN CN94117060A patent/CN1039911C/zh not_active Expired - Lifetime
- 1994-10-17 JP JP6250778A patent/JP2664344B2/ja not_active Expired - Fee Related
-
1995
- 1995-05-22 US US08/445,921 patent/US5777108A/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GB | Transfer or assigment of application |
Owner name: HOECHST MARION ROUSSEL, INC. |
|
| PC | Transfer of assignment of patent |
Owner name: AVENTISUB II INC. Free format text: AVENTISUB II INC. |
|
| MA | Patent expired |