FI95381B - Förfarande för framställning av terapeutiskt användbara racemiskt eller optiskt aktiva pyrido/1,2-a/pyraziner - Google Patents
Förfarande för framställning av terapeutiskt användbara racemiskt eller optiskt aktiva pyrido/1,2-a/pyraziner Download PDFInfo
- Publication number
- FI95381B FI95381B FI913510A FI913510A FI95381B FI 95381 B FI95381 B FI 95381B FI 913510 A FI913510 A FI 913510A FI 913510 A FI913510 A FI 913510A FI 95381 B FI95381 B FI 95381B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- preparation
- nmr
- optically active
- pyrido
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Claims (6)
1. Förfarande för framställning av ett racemiskt eller optiskt aktivt pyrido[l,2-a]pyratsin med formeln 5 H h (I) väri X är N eller CH; Y är r^N r^N N^N N— , I N—, i N— X N— ^ N</ N.-/ ' ‘-VN_/ ' (Vili) (IX) (X) χλ0 (XI) 20 o o 0 o (Γ* =Λ Λ Λ „ ' Si ' S( ' lCH=S ' " 0 0 0 0 (XII) (XIII) (XIV) (XV) 0 0 on JJ CH1v //
30 HN \ 3nN^\ :.· I N— I N — (CH') , 0 0 (XVI) (XVII) 35 39 95381 varvid grupperna enligt formler XV, XVI och XVII even-tuellt är substituerade vid kolatomen med högst tvä metyl-grupper, och n är 1 eller 2; 5 eller för framställning av ett farmaceutiskt godtagbart sait därav, kännetecknat av, att man omsätter a) en racemisk eller optisk aktiv förening med for- meln H I LH (XVIII) 15 väri X är N eller CH, med en förening med formeln YH, väri Y är ovan definierat, i närvaro av en kopplande reaktant, b) en racemisk eller optisk aktiv förening med formeln
20 H CHgSO-O^KN l-'H (xix) ... 25 » väri X är N eller CH, med en anjon med formeln Y~, vilken bildats av inverkan av en bas pä en förening YH; eller c) när Y4 är en grupp enligt nägon av formlerna XI, XII, XIII, XIV, XV eller XVII, en racemisk eller optisk 30 aktiv förening med formeln » « : H k (xx) 40 95381 med en anhydrid med fonneln o 0 0 0 I—V ^ rft_ s"^n °'J^ 5 c^Q0-' ^ ' S\ v· 0 0 'o 0 (XXI) (XXII) (XXIII) (XXIV) 10 0 0 // CH3s, // Γο— CCHjw0-- 15. o (xxv) (xxvi) varvid grupperna enligt formler XXV och XXVI eventuellt är substituerade vid kolatomen med högst tvä metylgrupper och n Sr 1 eller 2, och, 20 om si önskas, man omvandlar den erhällna föreningen med formeln I till ett farmaceutiskt godtagbart salt.
2. Förfarande enligt patentkrav 1, k ä n n e - t e c k n a d av, att man framställer en förening med formeln I, väri X är N och Y är en grupp med formeln XV .,, 25 ovh n är 1.
3. Optiskt aktiv förening med formeln H 30 (XXVII) väri X är N eller CH;
35 Y3 är HO-, RSOjO-, RlCOO eller H2N-; 4ΐ 95381 Ί a R är metyl; och R1 är Cj.j-alkyl; eller ett optiskt aktivt syrasalt därav när Y3 är H2N. • « • ·
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1989/000275 WO1990008148A1 (en) | 1989-01-23 | 1989-01-23 | Bis-aza-bicyclic anxiolytic agents |
| US8900275 | 1989-01-23 | ||
| PCT/US1989/003811 WO1990008144A1 (en) | 1989-01-23 | 1989-09-01 | Bis-aza-bicyclic anxiolytic agents |
| US8903811 | 1989-09-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI913510A0 FI913510A0 (sv) | 1991-07-22 |
| FI95381B true FI95381B (sv) | 1995-10-13 |
| FI95381C FI95381C (sv) | 1996-01-25 |
Family
ID=22214801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI913510A FI95381C (sv) | 1989-01-23 | 1991-07-22 | Förfarande för framställning av terapeutiskt användbara racemiskt eller optiskt aktiva pyrido/1,2-a/pyraziner |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US5122525A (sv) |
| EP (1) | EP0380217B1 (sv) |
| JP (1) | JPH0643427B2 (sv) |
| KR (1) | KR910009289B1 (sv) |
| CN (1) | CN1022186C (sv) |
| AP (1) | AP128A (sv) |
| AR (1) | AR246969A1 (sv) |
| AT (1) | ATE82574T1 (sv) |
| AU (1) | AU614214B2 (sv) |
| BA (1) | BA98302A (sv) |
| BG (1) | BG51046A3 (sv) |
| CA (1) | CA2008108C (sv) |
| CZ (1) | CZ277698B6 (sv) |
| DD (1) | DD291560A5 (sv) |
| DE (1) | DE69000467T2 (sv) |
| DK (1) | DK0380217T3 (sv) |
| EG (1) | EG19306A (sv) |
| ES (1) | ES2053094T3 (sv) |
| FI (1) | FI95381C (sv) |
| GR (1) | GR3006925T3 (sv) |
| HU (1) | HU215154B (sv) |
| IE (1) | IE62670B1 (sv) |
| IL (1) | IL93073A (sv) |
| IS (1) | IS1667B (sv) |
| MA (1) | MA21735A1 (sv) |
| MX (1) | MX19222A (sv) |
| MY (1) | MY104861A (sv) |
| NO (1) | NO175978C (sv) |
| NZ (1) | NZ232168A (sv) |
| OA (1) | OA10041A (sv) |
| PL (1) | PL163836B1 (sv) |
| PT (1) | PT92919B (sv) |
| RO (1) | RO110142B1 (sv) |
| RU (1) | RU2015977C1 (sv) |
| SK (1) | SK279339B6 (sv) |
| WO (2) | WO1990008148A1 (sv) |
| YU (1) | YU47554B (sv) |
| ZA (1) | ZA90430B (sv) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990008148A1 (en) * | 1989-01-23 | 1990-07-26 | Pfizer Inc. | Bis-aza-bicyclic anxiolytic agents |
| WO1992000075A1 (en) * | 1990-06-29 | 1992-01-09 | Pfizer Inc. | Pyridopyrazine derivatives for treating substance abuse and addiction |
| ATE120746T1 (de) * | 1991-01-31 | 1995-04-15 | Pfizer | Recematspaltung von trans-2-(2-pyrimidinyl)-7- (hydroxymethyl)octahydro-2h-pyrido(1,2-a>- pyrazin. |
| US5185449A (en) * | 1991-02-27 | 1993-02-09 | Pfizer Inc. | Process and intermediate for certain bis-aza-bicyclic anxiolytic agents |
| US5157034A (en) * | 1991-02-27 | 1992-10-20 | Pfizer Inc. | Neuroleptic perhydro-1H-pyrido[1,2-a]pyrazines |
| EP0573464B1 (en) * | 1991-02-27 | 1997-03-19 | Pfizer Inc. | Process for preparing trans-piperidine-2,5-dicarboxylates |
| US5311195A (en) * | 1991-08-30 | 1994-05-10 | Etak, Inc. | Combined relative and absolute positioning method and apparatus |
| ATE146178T1 (de) * | 1991-09-25 | 1996-12-15 | Pfizer | Neuroleptisch 2-substituierte perhydro-1h- pyrido(1,2-a>pyrazine |
| EP0646116B1 (en) * | 1992-06-16 | 1999-10-13 | Pfizer Inc. | Process and intermediates for bis-aza-bicyclic anxiolytic agents |
| AU5291793A (en) * | 1992-09-24 | 1994-04-12 | National Institutes Of Health | Aralkyl diazabicycloalkane derivatives for cns disorders |
| IL104506A (en) * | 1993-01-25 | 1997-11-20 | Israel State | Fast changing heating- cooling device and method, particularly for cryogenic and/or surgical use |
| US5637713A (en) * | 1993-08-20 | 1997-06-10 | Pfizer Inc. | Process for preparing trans-piperidine-2,5-dicarboxylates |
| US5455350A (en) * | 1993-10-13 | 1995-10-03 | Pfizer Inc. | Process and intermediate for certain bis-aza-bicyclic anxiolytic agents |
| IL107460A (en) * | 1993-11-01 | 1999-06-20 | Israel State | Controlled cryogenic contact system |
| JP3287574B2 (ja) * | 1994-09-30 | 2002-06-04 | ファイザー・インク | ２，７−置換オクタヒドロ−１ｈ−ピリド［１，２−ａ］ピラジン誘導体 |
| US5731307A (en) * | 1994-09-30 | 1998-03-24 | Pfizer, Inc. | Neuroleptic 2,7-disubtituted perhydro-1h-pyrido 1, 2-A!pyrazines |
| US6231833B1 (en) * | 1999-08-05 | 2001-05-15 | Pfizer Inc | 2,7-substituted octahydro-1H-pyrido[1,2-A]pyrazine derivatives as ligands for serotonin receptors |
| IL124453A0 (en) * | 1995-12-21 | 1998-12-06 | Pfizer | 2,7-substituted octahydro-pyrrolo [1,2-A]pyrazine derivatives |
| BR9710018A (pt) * | 1996-07-01 | 1999-08-10 | Pfizer | Preparação de (7S,trans)-2-(2-pirimidinil)-7-(hidroximetil)octa-hidro-2H-pirido[1,2-A]pirazina |
| PA8469101A1 (es) * | 1998-04-09 | 2000-09-29 | Pfizer Prod Inc | Ligandos azabiciclicos de receptores 5ht1 |
| US6251893B1 (en) * | 1998-06-15 | 2001-06-26 | Nps Allelix Corp. | Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity |
| HN1999000146A (es) * | 1998-09-21 | 2000-11-11 | Pfizer Prod Inc | Agentes farmaceuticos para el tratamiento de la enfermedad de parkinson, adhd y microadenomas. |
| US20020016334A1 (en) * | 2000-07-31 | 2002-02-07 | Coe Jotham Wadsworth | Pharmaceutical composition for the treatment of attention deficit hyperactivity disorder (ADHD) |
| US6670476B2 (en) | 2000-11-29 | 2003-12-30 | Pfizer Inc. | Resolution of trans-7-(hydroxy-methyl)octa-hydro-2H-pyrido[1,2-a]pyrazine |
| AU2004220327B2 (en) * | 2003-03-12 | 2010-06-24 | Pfizer Products Inc. | Pyridyloxymethyl and benzisoxazole azabicyclic derivatives |
| EP1633756B1 (en) | 2003-04-09 | 2008-12-24 | Biogen Idec MA Inc. | A2a adenosine receptor antagonists |
| JP4864719B2 (ja) * | 2003-11-26 | 2012-02-01 | ファイザー・プロダクツ・インク | Ｇｓｋ−３インヒビターとしてのアミノピラゾール誘導体 |
| US20070219201A1 (en) * | 2004-05-27 | 2007-09-20 | Warner-Lambert Company Llc | Combination of atomoxetine and a 5ht1a receptor agonist for treating adhd and other disorders |
| US7658206B2 (en) | 2006-12-05 | 2010-02-09 | Kohler Co. | Plumbing valve with stick control handle |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3388128A (en) * | 1965-09-03 | 1968-06-11 | Allan R. Day | Substituted 1, 4-diazabicyclo [4. 4. 9] decanes |
| US4182763A (en) * | 1978-05-22 | 1980-01-08 | Mead Johnson & Company | Buspirone anti-anxiety method |
| US4339579A (en) * | 1980-12-29 | 1982-07-13 | American Home Products Corporation | 2,6-Bis-(pyrrolopyrazinyl)pyrazines |
| US4400511A (en) * | 1982-05-07 | 1983-08-23 | American Home Products Corporation | 2-Substituted octahydropyrrolo(1,2-A)-pyrazine-3-carboxylic acids |
| US4414389A (en) * | 1982-05-25 | 1983-11-08 | American Home Products Corporation | 4-Substituted-piperidino carboxamides |
| US4517187A (en) * | 1982-10-18 | 1985-05-14 | Pennwalt Corporation | 1,3,4,6,7-11b-Hexahydro-7-phenyl-2H-pyrazino[2,1-a]isoquinolines methods of preparation, and use as antidepressants |
| DE3321969A1 (de) * | 1983-06-18 | 1984-12-20 | Troponwerke GmbH & Co KG, 5000 Köln | 2-pyrimidinyl-1-piperazin-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| DE3409440A1 (de) * | 1984-03-15 | 1985-09-26 | Bayer Ag, 5090 Leverkusen | Imidazo(1,5-a)pyridyl-methan- und imidazo(1,5-b)pyridazinylmethan-derivate, ihre herstellung und sie enthaltende aufzeichnungsmaterialien |
| IT1204803B (it) * | 1986-02-17 | 1989-03-10 | Acraf | Composto farmacologicamente attivo e composizioni farmaceutiche che lo contengono,procedimento per prepararlo e intermedio utile in detto procedimento |
| US4788290A (en) * | 1987-12-11 | 1988-11-29 | American Home Products Corporation | Serotonergic pyrazine derivatives |
| JP2668259B2 (ja) * | 1988-02-18 | 1997-10-27 | 塩野義製薬株式会社 | 複素環化合物および抗潰瘍剤 |
| WO1990008148A1 (en) * | 1989-01-23 | 1990-07-26 | Pfizer Inc. | Bis-aza-bicyclic anxiolytic agents |
-
1989
- 1989-01-23 WO PCT/US1989/000275 patent/WO1990008148A1/en unknown
- 1989-01-23 MX MX1922290A patent/MX19222A/es unknown
- 1989-09-01 HU HU40/90A patent/HU215154B/hu not_active IP Right Cessation
- 1989-09-01 RO RO148053A patent/RO110142B1/ro unknown
- 1989-09-01 WO PCT/US1989/003811 patent/WO1990008144A1/en active IP Right Grant
- 1989-12-13 IS IS3529A patent/IS1667B/is unknown
-
1990
- 1990-01-12 EP EP90300362A patent/EP0380217B1/en not_active Expired - Lifetime
- 1990-01-12 DE DE9090300362T patent/DE69000467T2/de not_active Expired - Fee Related
- 1990-01-12 ES ES90300362T patent/ES2053094T3/es not_active Expired - Lifetime
- 1990-01-12 AT AT90300362T patent/ATE82574T1/de not_active IP Right Cessation
- 1990-01-12 DK DK90300362.2T patent/DK0380217T3/da active
- 1990-01-16 IL IL9307390A patent/IL93073A/en not_active IP Right Cessation
- 1990-01-18 BG BG090949A patent/BG51046A3/xx unknown
- 1990-01-19 NZ NZ232168A patent/NZ232168A/xx unknown
- 1990-01-19 MY MYPI90000101A patent/MY104861A/en unknown
- 1990-01-19 AR AR90315971A patent/AR246969A1/es active
- 1990-01-19 CA CA002008108A patent/CA2008108C/en not_active Expired - Fee Related
- 1990-01-21 EG EG3290A patent/EG19306A/xx active
- 1990-01-22 DD DD90337249A patent/DD291560A5/de not_active IP Right Cessation
- 1990-01-22 ZA ZA90430A patent/ZA90430B/xx unknown
- 1990-01-22 AP APAP/P/1990/000158A patent/AP128A/en active
- 1990-01-22 SK SK299-90A patent/SK279339B6/sk unknown
- 1990-01-22 IE IE22590A patent/IE62670B1/en not_active IP Right Cessation
- 1990-01-22 AU AU48679/90A patent/AU614214B2/en not_active Ceased
- 1990-01-22 CZ CS90299A patent/CZ277698B6/cs not_active IP Right Cessation
- 1990-01-22 CN CN90100291A patent/CN1022186C/zh not_active Expired - Fee Related
- 1990-01-22 PL PL90283395A patent/PL163836B1/pl not_active IP Right Cessation
- 1990-01-22 YU YU11190A patent/YU47554B/sh unknown
- 1990-01-22 MA MA21996A patent/MA21735A1/fr unknown
- 1990-01-22 PT PT92919A patent/PT92919B/pt not_active IP Right Cessation
- 1990-01-22 KR KR1019900000701A patent/KR910009289B1/ko not_active IP Right Cessation
- 1990-01-23 OA OA59727A patent/OA10041A/en unknown
- 1990-01-23 JP JP2013459A patent/JPH0643427B2/ja not_active Expired - Fee Related
-
1991
- 1991-07-09 US US07/721,537 patent/US5122525A/en not_active Expired - Lifetime
- 1991-07-22 FI FI913510A patent/FI95381C/sv not_active IP Right Cessation
- 1991-07-22 RU SU915001279A patent/RU2015977C1/ru not_active IP Right Cessation
- 1991-07-22 NO NO912863A patent/NO175978C/no unknown
-
1993
- 1993-01-28 GR GR930400172T patent/GR3006925T3/el unknown
-
1998
- 1998-03-30 BA BA980302A patent/BA98302A/bs unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MA | Patent expired |