BR9815237A - Processo para preparação de derivados de aminocarbonil de geneserolina que possuem atividade anticolinesterase seletiva no cérebro - Google Patents
Processo para preparação de derivados de aminocarbonil de geneserolina que possuem atividade anticolinesterase seletiva no cérebroInfo
- Publication number
- BR9815237A BR9815237A BR9815237-8A BR9815237A BR9815237A BR 9815237 A BR9815237 A BR 9815237A BR 9815237 A BR9815237 A BR 9815237A BR 9815237 A BR9815237 A BR 9815237A
- Authority
- BR
- Brazil
- Prior art keywords
- geneseroline
- brain
- preparing
- formula
- selective
- Prior art date
Links
- 210000004556 brain Anatomy 0.000 title abstract 3
- 239000000544 cholinesterase inhibitor Substances 0.000 title abstract 2
- 230000000694 effects Effects 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 title 1
- OPAXVHIAQIXNAM-STQMWFEESA-N (4as,9as)-2,4a,9-trimethyl-4,9a-dihydro-3h-oxazino[6,5-b]indol-6-ol Chemical compound C12=CC(O)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN(C)O2 OPAXVHIAQIXNAM-STQMWFEESA-N 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 150000004703 alkoxides Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- CNBHDDBNEKKMJH-UHFFFAOYSA-N (2,4a,9-trimethyl-4,9a-dihydro-3h-oxazino[6,5-b]indol-6-yl) n-methylcarbamate Chemical compound O1N(C)CCC2(C)C3=CC(OC(=O)NC)=CC=C3N(C)C21 CNBHDDBNEKKMJH-UHFFFAOYSA-N 0.000 abstract 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 abstract 1
- 229960001697 physostigmine Drugs 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PROCESSO PARA PREPARAçãO DE DERIVADOS DE AMINOCARBONIL DE GENESEROLINA QUE POSSUEM ATIVIDADE ANTICOLINESTERASE SELETIVA NO CéREBRO Um processo para a preparação dos compostos da fórmula (I): onde R é C~ 2~-C~ 20~ alcil linear ou ramificado, C~ 3~-C~ 7~ cicloalcil, fenila ou benzila, que podem, opcionalmente ser substituídos por C~ 1~-C~ 4~ alcil, halógeno ou C~ 1~-C~ 4~ grupo alcóxido, e este processo compreende: a) oxidação da eserina com peróxido de hidrogênio na presença de uma base e a subseq³ente hidrólise para geneserolina, sem o isolamento da geneserina intermediária; b) acilação da geneserolina com um isocianato da fórmula R-N=C=0, onde R é conforme definido acima, na presença de um catalisador básico; c) transformação opcional em um sal farmaceuticamente aceitável. Compostos da fórmula (I), onde R é fenila ou benzila, que podem, opcionalmente. ser substituídos por alcil, halógeno ou alcóxido, como inibidores seletivos potentes da anticolinesterase no cérebro.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT002300 IT1295310B1 (it) | 1997-10-10 | 1997-10-10 | Amminocarbonil derivati di geneserolina ad attivita' anticolinesterasica selettiva a livello cerebrale |
| IT002299 IT1295309B1 (it) | 1997-10-10 | 1997-10-10 | Procedimento per la preparazione di amminocarbonil derivati di geneserolina |
| PCT/EP1998/006377 WO1999019329A1 (en) | 1997-10-10 | 1998-10-07 | A process for the preparation of aminocarbonyl derivatives of geneseroline having selective brain anticholinesterase activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BR9815237A true BR9815237A (pt) | 2000-10-31 |
Family
ID=26331547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR9815237-8A BR9815237A (pt) | 1997-10-10 | 1998-10-07 | Processo para preparação de derivados de aminocarbonil de geneserolina que possuem atividade anticolinesterase seletiva no cérebro |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6297237B1 (pt) |
| EP (1) | EP1023297A1 (pt) |
| KR (1) | KR20010015714A (pt) |
| CN (1) | CN1278264A (pt) |
| AR (1) | AR018511A1 (pt) |
| AU (1) | AU750964B2 (pt) |
| BR (1) | BR9815237A (pt) |
| CA (1) | CA2274658A1 (pt) |
| EA (1) | EA003192B1 (pt) |
| HU (1) | HUP0003747A3 (pt) |
| IL (1) | IL135399A0 (pt) |
| NZ (1) | NZ503773A (pt) |
| PL (1) | PL339761A1 (pt) |
| SK (1) | SK5032000A3 (pt) |
| TR (1) | TR200000951T2 (pt) |
| TW (1) | TW490467B (pt) |
| WO (1) | WO1999019329A1 (pt) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1109003B (it) | 1977-09-20 | 1985-12-16 | Univ Firenze | Derivati dell 1 2 3 8 3 a 8 a esai dropirrolo 23 b indolo |
| US4791107A (en) | 1986-07-16 | 1988-12-13 | Hoechst-Roussel Pharmaceuticals, Inc. | Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and) 1,3A,8)-di(and tri)methylpyrrolo(2,3-B)indoles, compositions and use |
| IT1251166B (it) * | 1991-08-09 | 1995-05-04 | Chiesi Farma Spa | Derivati di geneserina,loro preparazione e composizioni farmaceutiche che li contengono |
| US5571929A (en) * | 1994-12-07 | 1996-11-05 | The United States Of America As Represented By The Department Of Health And Human Services | Resolution and reduction of physostigmine intermediates and derivatives |
| US5677457A (en) * | 1996-12-19 | 1997-10-14 | Hoechst Marion Roussel, Inc. | Method of preparation of physostigmine carbamate derivatives from eseroline ethers |
-
1998
- 1998-10-07 AU AU11516/99A patent/AU750964B2/en not_active Ceased
- 1998-10-07 NZ NZ503773A patent/NZ503773A/en unknown
- 1998-10-07 KR KR1020007003805A patent/KR20010015714A/ko not_active Withdrawn
- 1998-10-07 BR BR9815237-8A patent/BR9815237A/pt not_active IP Right Cessation
- 1998-10-07 EA EA200000300A patent/EA003192B1/ru not_active IP Right Cessation
- 1998-10-07 WO PCT/EP1998/006377 patent/WO1999019329A1/en not_active Ceased
- 1998-10-07 IL IL13539998A patent/IL135399A0/xx unknown
- 1998-10-07 EP EP98954370A patent/EP1023297A1/en not_active Withdrawn
- 1998-10-07 SK SK503-2000A patent/SK5032000A3/sk unknown
- 1998-10-07 CN CN98810683A patent/CN1278264A/zh active Pending
- 1998-10-07 CA CA002274658A patent/CA2274658A1/en not_active Abandoned
- 1998-10-07 PL PL98339761A patent/PL339761A1/xx unknown
- 1998-10-07 HU HU0003747A patent/HUP0003747A3/hu unknown
- 1998-10-07 US US09/319,693 patent/US6297237B1/en not_active Expired - Fee Related
- 1998-10-07 TR TR2000/00951T patent/TR200000951T2/xx unknown
- 1998-10-09 AR ARP980105062A patent/AR018511A1/es unknown
- 1998-10-23 TW TW087117571A patent/TW490467B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| AU1151699A (en) | 1999-05-03 |
| US6297237B1 (en) | 2001-10-02 |
| EA200000300A1 (ru) | 2000-12-25 |
| PL339761A1 (en) | 2001-01-02 |
| EP1023297A1 (en) | 2000-08-02 |
| HUP0003747A2 (hu) | 2001-10-28 |
| HUP0003747A3 (en) | 2001-12-28 |
| WO1999019329A1 (en) | 1999-04-22 |
| TW490467B (en) | 2002-06-11 |
| NZ503773A (en) | 2002-05-31 |
| AU750964B2 (en) | 2002-08-01 |
| AR018511A1 (es) | 2001-11-28 |
| EA003192B1 (ru) | 2003-02-27 |
| SK5032000A3 (en) | 2000-10-09 |
| KR20010015714A (ko) | 2001-02-26 |
| IL135399A0 (en) | 2001-05-20 |
| CN1278264A (zh) | 2000-12-27 |
| TR200000951T2 (tr) | 2000-07-21 |
| CA2274658A1 (en) | 1999-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE A 5O,6O,7O,8O, E A 9O ANUIDADES |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: REFERENTE AO DESPACHO 8.6 PUBLICADO NA RPI 1910 DE 14/08/2007. |