FI93211B - Förfarande för framställning av nya, terapeutiskt användbara 1,2,5,6-tetrahydropyridinderivat - Google Patents
Förfarande för framställning av nya, terapeutiskt användbara 1,2,5,6-tetrahydropyridinderivat Download PDFInfo
- Publication number
- FI93211B FI93211B FI881892A FI881892A FI93211B FI 93211 B FI93211 B FI 93211B FI 881892 A FI881892 A FI 881892A FI 881892 A FI881892 A FI 881892A FI 93211 B FI93211 B FI 93211B
- Authority
- FI
- Finland
- Prior art keywords
- compound
- formula
- compounds
- tetrahydropyridine
- radical
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
Landscapes
- 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)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Psychiatry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Claims (5)
1. Förfarande för framställning av terapeutiskt användbara 1,2,5,6-tetrahydropyridinderivat med formeln 5 (I) samt syraadditionssalter därav: f1 C=N 0 R 2 10 lNJ (I) R där R betecknar en väteatom, en hydroxylradikal, en li-15 neär, förgrenad eller cyklisk, mättad eller omättad alkyl-radikal med högst 4 kolatomer, Rj^ betecknar en lineär, förgrenad eller cyklisk, mättad eller omättad alkylradikal med högst 8 kolatomer och R2 betecknar en lineär, mättad eller omättad alkylradikal med högst 6 kolatomer, förut-20 satt, att R ej kan vara metyl, kännetecknat därav, att a) för framställning av föreningar med formeln (I), där Rx och R2 betecknar samma som ovan och R betecknar sam-ma som ovan, förutom hydroxyl, omsätts en förening med 25 formeln (II): 0rLi
30. N/ där Rx betecknar samma som ovan, med en förening, som har 35 formeln (III): ti 29 9321 1 nh2or'2 eller med ett salt därav, där R'2 betecknar en lineär, mät-5 tad eller omättad alkylradikal med högst 6 kolatomer, för erhällande av en förening med formeln (IV): f1 10 r^N— c=nor'2 r f (lv» 15 som omsätts med en alkylhalogenid, som har formeln (V) R*-Hai där Hai betecknar en halogenatom och R' betecknar en li-20 neär, förgrenad eller cyklisk, mättad eller omättad alkylradikal med högst 4 kolatomer, för erhällande av en förening med formeln (VI): R1
25 I 1 7|-C=N0R' 7 ^ (VI) R'®Hal® som omsätts med en hydrogenerande förening, säsom natrium-borhydrid, för erhällande av en förening med formeln (IA): 30 9321 1 R1 i^^V-C^NOR'j U 5 ' . R' där R', Rx och R’2 betecknar sanuna som ovan, vilken förening, om sä önskas, omvandlas till ett salt, eller 10 b) för framställning av föreningar med formeln (I), där R2 och R2 betecknar sanuna som ovan och R betecknar en hydroxylradikal, omsätts en förening, som har formeln (VIII):
15 R-L aC=N0R2 (VIII) Ϊ o 20 med ett reduceringsmedel, säsom natriumborhydrid, för er-hällande av en förening med formeln (IF): 25 Ri I ^ ^ —C=N0R2 (I,) OH 30 där Rx och R2 betecknar samma som ovan, vilken förening, om sä önskas, omvandlas tili ett sait.
2. Förfarande enligt patentkravet 1, k ä n n e -35 tecknat därav, att som utgängsämne används en förening, där Rx betecknar en metylradikal. Il: 31 9321 1
3. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att som utgängsämne används en före-ning, där R'2 eller R2 betecknar en metylradikal.
4. Förfarande enligt patentkravet 1, känne- 5 tecknat därav, att man framställer en förening med formeln (I), där R betecknar en väteatom eller en hydro-xylradikal, samt syraadditionssalter därav.
5. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer följande före- 10 ningar med formeln (I): 3-acetyl-l,2,5,6-tetrahydropyridin-0-metyloxim och en hydroklorid därav, l-N-hydroxyl-3-acetyl-l,2,5,6-tetrahydropyridin-0-metyloxim.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20260/87A IT1203971B (it) | 1987-04-24 | 1987-04-24 | Derivati di 1,2,5,6-tetraidropiridina, loro procedimento di preparazione e loro applicazione come medicamenti |
| IT2026087 | 1987-04-24 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI881892A0 FI881892A0 (sv) | 1988-04-22 |
| FI881892A FI881892A (sv) | 1988-10-25 |
| FI93211B true FI93211B (sv) | 1994-11-30 |
| FI93211C FI93211C (sv) | 1995-03-10 |
Family
ID=11165225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI881892A FI93211C (sv) | 1987-04-24 | 1988-04-22 | Förfarande för framställning av nya, terapeutiskt användbara 1,2,5,6-tetrahydropyridinderivat |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0288394B1 (sv) |
| JP (1) | JP2727192B2 (sv) |
| KR (1) | KR960012365B1 (sv) |
| AT (1) | ATE80387T1 (sv) |
| AU (1) | AU614283B2 (sv) |
| CA (1) | CA1340986C (sv) |
| DE (1) | DE3874396T2 (sv) |
| DK (1) | DK167758B1 (sv) |
| ES (1) | ES2043863T3 (sv) |
| FI (1) | FI93211C (sv) |
| GR (1) | GR3005647T3 (sv) |
| HU (1) | HU199795B (sv) |
| IE (1) | IE63172B1 (sv) |
| IL (1) | IL86157A (sv) |
| IT (1) | IT1203971B (sv) |
| MX (1) | MX11201A (sv) |
| NZ (1) | NZ224357A (sv) |
| OA (1) | OA08835A (sv) |
| PH (1) | PH25574A (sv) |
| PT (1) | PT87290B (sv) |
| SU (1) | SU1678203A3 (sv) |
| ZA (1) | ZA882595B (sv) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL81610A (en) * | 1986-02-27 | 1990-12-23 | Roussel Uclaf | Derivatives of 1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime,their preparation and pharmaceutical compositions containing them |
| US4786648A (en) * | 1986-12-08 | 1988-11-22 | Warner-Lambert Company | O-substituted tetrahydropyridine oxime cholinergic agents |
| IT1222526B (it) * | 1987-08-21 | 1990-09-05 | Roussel Maestretti Spa | Derivati dell' ossima della 1,2,5,6-tetraidropiridin-3-carbossaldeide,loro procedimento di preparazione e loro impiego come sostanze medicinali |
| US5110828A (en) * | 1988-04-15 | 1992-05-05 | Beecham Group P.L.C. | Azabicyclo oxime derivatives |
| US5278170A (en) * | 1989-04-13 | 1994-01-11 | Beecham Group P.L.C. | Azabicylo oxime compounds |
| EP0392803B1 (en) * | 1989-04-13 | 2004-06-16 | Beecham Group p.l.c. | Novel compounds |
| IE912974A1 (en) * | 1990-08-24 | 1992-02-26 | Beecham Group Plc | Novel compounds |
| GB9019095D0 (en) * | 1990-09-01 | 1990-10-17 | Beecham Group Plc | Novel compounds |
| EP0552213A1 (en) * | 1990-10-12 | 1993-07-28 | Beecham Group Plc | 1,2,5,6-tetrahydropyridine oxime derivatives |
| CA2080536A1 (en) * | 1991-10-17 | 1993-04-18 | John S. Ward | Nicotinic activity of a series of arecolones and isoarecolones |
| WO1993011767A1 (en) * | 1991-12-18 | 1993-06-24 | Warner-Lambert Company | Transdermal delivery of (e)-1,2,5,6-tetrahydro-1-methyl-3-pyridine-carboxaldehyde-o-methyloxine hcl and related compounds in the treatment of cognitive disorders and for analgesia |
| US5362860A (en) * | 1993-02-01 | 1994-11-08 | Warner-Lambert Company | Neutral stabilization complex for CI-979 HCl, a cognition activator |
| US5424301A (en) * | 1993-02-01 | 1995-06-13 | Warner-Lambert Company | Starch stabilized o-substituted tetrahydropyridine oxime cholinergic agents |
| US6250886B1 (en) | 1999-09-03 | 2001-06-26 | Chittom International, Inc. | Axial flow fan and fan blade |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1258847A (fr) * | 1960-02-12 | 1961-04-21 | Ciba Geigy | Procédé de préparation de nouveaux dérivés pyridiniques, entre autres de l'oxime de la l-méthyl-3 ou 4-acétyl-1, 2, 5, 6-tétrahydropyridine |
| IL81610A (en) * | 1986-02-27 | 1990-12-23 | Roussel Uclaf | Derivatives of 1,2,5,6-tetrahydropyridin-3-carboxaldehyde oxime,their preparation and pharmaceutical compositions containing them |
| JPH0641332B2 (ja) * | 1986-09-17 | 1994-06-01 | 株式会社共同精機工作所 | 断裁機へのシ−ト類供給装置 |
| US4786648A (en) * | 1986-12-08 | 1988-11-22 | Warner-Lambert Company | O-substituted tetrahydropyridine oxime cholinergic agents |
| US4710508A (en) * | 1986-12-08 | 1987-12-01 | Warner-Lambert Company | O-substituted tetrahydropyridine oxime cholinergic agents |
| US4798841A (en) * | 1987-03-31 | 1989-01-17 | Warner-Lambert Company | Tetrahydropyridine oxime cholinergic agents and method of treatment |
-
1987
- 1987-04-24 IT IT20260/87A patent/IT1203971B/it active
-
1988
- 1988-04-13 ZA ZA882595A patent/ZA882595B/xx unknown
- 1988-04-21 DK DK216388A patent/DK167758B1/da not_active IP Right Cessation
- 1988-04-21 PT PT87290A patent/PT87290B/pt not_active IP Right Cessation
- 1988-04-21 MX MX1120188A patent/MX11201A/es unknown
- 1988-04-22 PH PH36830A patent/PH25574A/en unknown
- 1988-04-22 ES ES88400996T patent/ES2043863T3/es not_active Expired - Lifetime
- 1988-04-22 SU SU884355793A patent/SU1678203A3/ru active
- 1988-04-22 HU HU882057A patent/HU199795B/hu not_active IP Right Cessation
- 1988-04-22 JP JP63098476A patent/JP2727192B2/ja not_active Expired - Fee Related
- 1988-04-22 IE IE120788A patent/IE63172B1/en not_active IP Right Cessation
- 1988-04-22 IL IL8615788A patent/IL86157A/en not_active IP Right Cessation
- 1988-04-22 OA OA59335A patent/OA08835A/xx unknown
- 1988-04-22 FI FI881892A patent/FI93211C/sv not_active IP Right Cessation
- 1988-04-22 EP EP88400996A patent/EP0288394B1/fr not_active Expired - Lifetime
- 1988-04-22 NZ NZ224357A patent/NZ224357A/en unknown
- 1988-04-22 CA CA000564817A patent/CA1340986C/fr not_active Expired - Fee Related
- 1988-04-22 DE DE8888400996T patent/DE3874396T2/de not_active Expired - Fee Related
- 1988-04-22 AT AT88400996T patent/ATE80387T1/de not_active IP Right Cessation
- 1988-04-22 AU AU15111/88A patent/AU614283B2/en not_active Ceased
- 1988-04-23 KR KR1019880004709A patent/KR960012365B1/ko not_active IP Right Cessation
-
1992
- 1992-09-10 GR GR920401660T patent/GR3005647T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| PC | Transfer of assignment of patent |
Owner name: HOECHST MARION ROUSSEL |
|
| FG | Patent granted |
Owner name: AVENTIS PHARMA S.A. |
|
| MA | Patent expired |