FI68828C - Foerfarande foer framstaellning av nya neuroleptiska 2-(aminoalkyl)-5-fenyl-2,3,4,4a,5,9b-hexahydro-4a,9b-trans-1h-pyrido(4,3-b)indolderivat - Google Patents
Foerfarande foer framstaellning av nya neuroleptiska 2-(aminoalkyl)-5-fenyl-2,3,4,4a,5,9b-hexahydro-4a,9b-trans-1h-pyrido(4,3-b)indolderivat Download PDFInfo
- Publication number
- FI68828C FI68828C FI802371A FI802371A FI68828C FI 68828 C FI68828 C FI 68828C FI 802371 A FI802371 A FI 802371A FI 802371 A FI802371 A FI 802371A FI 68828 C FI68828 C FI 68828C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- trans
- pyrido
- hexahydro
- amino
- Prior art date
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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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Claims (5)
1. Förfarande för framställning av nya neuroleptiska(+)-enantiomerer, blandningar av (+)-och (-)-enantiomerer och (-)-racemat av 2-(aminoalkyl)-5-fenyl-2,3/4,4a,5,9b-hexahydro-4a,9b-trans-lH-pyrido/4,3'b7indolderivat med formeln I H ’m'r·* 7 A ΙΟΙ Y väri m är 2-9, X och Y är oberoende av varandra H eller F och R är H, alkanoyl med 1-3 kolatomer, alkoxikarbonyl med 2-3 kolatomer eller en eventuellt monosubstituerad bensoyl- eller fenylsulfonylgrupp varvid substituenten är CH^, F, Cl, Br eller OCH^, samt för framställning av deras farmakologiskt godtagbara salter, känne-t e c k n a t därav, att en nitril med formeln IV H x- ;_i fopT r,CH2’”-iCN A (OJ \ Y väri X, Y och m betecknar samma som ovan, reduceras med metallhydrid i eterhaltigt lösningsmedel eller med väte över en ädelmetallkataly- 21 68828 sator i ett inert organiskt lösningsmedel till en förening med forraeln I, väri R är H, och da man vill framställa en förening med formeln I, väri R anger annat än väte, bringas den erhällna föreninger med formeln I, väri R är väte, att reagera med en acyl- eller sulfonylhalogenid (klorid eller bromid), som kan vara alkanoylhalogenid med 1-3 kol-atomer, alkoxikarbonylhalogenid med 2 eller 3 kolatomer, bensoyl-halogenid, fenylsulfonylhalogenid eller monosubstituerad bensoyl-eller fenylsulfonylhalogenid varvid substituenten är CH^, F, Cl, Br eller OCH^ i inert lösningsmedel, som innehäller ett neutrali-serande medel, eller en förening med formeln I, där R är väte, bringas att reagera med karboxylsyra eller sulfonsyra som motsvarar acyl- eller sulfonylhalogenid i inert lösningsmedel som innehäller dicyklohexylkarbodiimid, och om man sä vill, kan den erhällna föreningen med formeln I förvandlas tili syraadditionssalt.
2. Förfarande enligt patentkravet 1 för framställning av (+)- eller (-)-2-(N-bensoyl-1'-amino-n-but-4'-yl)-5-(p-fluorfenyl)- 8-fluor-2,3,4,4a,5,9b-hexahydro-4a,9b-trans--lH-pyrido/T,3-b7indol» kännetecknat därav, att ( + )- eller (-)-2-(4'-amino-n-but-4 '-yl)-5-(p-fluorfenyl)-8-fluor-2,3,4,4a,5,9b-hexähydro-4a,9b-trans-lH-pyrido/4,3-b7indol bringas att reagera med bensoylklorid.
3. Förfarande enligt patentkravet 1 för framställning av ( + )- eller (-)-2-,/N-(o-metoxibensoyl)-1'-amino-n-but-4 '-yl7~5- (p-fluorfenyl)-8-fluor-2,3,4,4a,5,9b-hexahydro-4a,9b-trans-lH-pyrido/_4,3-b7indol, kännetecknat därav, att (+)- eller ( —)—2—(4 *-amino-n-but-4'-yl)-5-(p-fluorfenyl)-8-fluor-2,3,4,4a,5,9b-hexahydro-4a,9b-trans-lH-pyrido^4,3-b/indol bringas att reagera med o-metoxibensoylklorid.
4. Förfarande enligt patentkravet 1 för framställning av (+)- eller (-)-2-(N-etoxikarbonyl-1'-amino-n-but-4'-yl)-5-(p-fluorfenyl ) -8-f luor-2,3, \ ,4a , 5,9b-hexahydro-4a , 9b-trans-lH-pyrido/_4,3-b/-indol, kännetecknat därav, att ( + )- eller ( —)—2—(4 * — amino-n-but-4'-yl)-5-(p-fluorfenyl)-8-fluor-2,3,4,4a,5,9b-hexahydro-4a,9b-trans-lH-pyrido/4,3-byindol bringas att reagera med etoxi-karbonylklorid.
5. Förfarande enligt patentkravet 1 för framställning av (+)- eller (-)-2-(N-acetyl-1’-amino-n-but-4'-yl)-5-fenyl-2,3,4,4a,5,9b-
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/061,573 US4252811A (en) | 1979-07-30 | 1979-07-30 | Hexahydro-trans-pyridoindole neuroleptic agents |
| US6157379 | 1979-07-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI802371A FI802371A (fi) | 1981-01-31 |
| FI68828B FI68828B (fi) | 1985-07-31 |
| FI68828C true FI68828C (fi) | 1985-11-11 |
Family
ID=22036658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI802371A FI68828C (fi) | 1979-07-30 | 1980-07-29 | Foerfarande foer framstaellning av nya neuroleptiska 2-(aminoalkyl)-5-fenyl-2,3,4,4a,5,9b-hexahydro-4a,9b-trans-1h-pyrido(4,3-b)indolderivat |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4252811A (sv) |
| JP (1) | JPS5626891A (sv) |
| KR (1) | KR840000914B1 (sv) |
| AR (1) | AR226314A1 (sv) |
| AT (1) | AT375659B (sv) |
| AU (1) | AU513948B2 (sv) |
| BE (1) | BE884530A (sv) |
| CA (1) | CA1133483A (sv) |
| CH (1) | CH644379A5 (sv) |
| CS (1) | CS221974B2 (sv) |
| DD (1) | DD153691A5 (sv) |
| DE (1) | DE3028555A1 (sv) |
| DK (1) | DK148140C (sv) |
| EG (1) | EG14903A (sv) |
| ES (1) | ES8105732A1 (sv) |
| FI (1) | FI68828C (sv) |
| FR (1) | FR2463140A1 (sv) |
| GB (1) | GB2055372B (sv) |
| GR (1) | GR69664B (sv) |
| IE (1) | IE50035B1 (sv) |
| IL (1) | IL60695A (sv) |
| IT (1) | IT1194815B (sv) |
| LU (1) | LU82662A1 (sv) |
| NL (1) | NL180216C (sv) |
| NO (1) | NO153729C (sv) |
| NZ (1) | NZ194467A (sv) |
| PH (1) | PH22657A (sv) |
| PL (1) | PL133456B1 (sv) |
| PT (1) | PT71623B (sv) |
| SE (1) | SE438505B (sv) |
| SU (1) | SU1172450A3 (sv) |
| YU (1) | YU42223B (sv) |
| ZA (1) | ZA804604B (sv) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337250A (en) * | 1979-07-30 | 1982-06-29 | Pfizer Inc. | Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents |
| US4748247A (en) * | 1986-10-21 | 1988-05-31 | American Home Products Corporation | 2-[4-[4-(2-Pyrimidinyl)-1-piperazinyl]alkyl]alkyl]pyrido- and pyrazino-indole-1,3-dione derivatives as histamine H1 antagonists |
| US5102889B1 (en) * | 1990-09-27 | 1993-05-11 | 2-(4-piperidinyl)-1h-pyrido(4,3-b)indol-1-ones and related compounds | |
| US5229517A (en) * | 1990-09-27 | 1993-07-20 | Hoechst-Roussel Pharmaceuticals Incorporated | 2-(4-Piperindinyl)-1H-pyrido[4,3-B]indol-1-ones and related compounds |
| JPH05101365A (ja) * | 1991-03-22 | 1993-04-23 | Tdk Corp | 垂直磁気記録媒体およびその製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3687961A (en) * | 1971-05-03 | 1972-08-29 | Abbott Lab | 8-fluoro-2-{8 3-(4-fluorophenylanilinopropyl{9 -gamma-carboline |
| AR205452A1 (es) * | 1973-12-06 | 1976-05-07 | Endo Lab | Metodo para preparar nuevos trans-2, 3, 4, 4a, 5, 9b-hexahidro-5-fenil-1h-pirido(4,3-b) indoles |
| JPS50126699A (sv) * | 1974-03-20 | 1975-10-04 | ||
| US4001263A (en) * | 1974-04-01 | 1977-01-04 | Pfizer Inc. | 5-Aryl-1,2,3,4-tetrahydro-γ-carbolines |
| SE7702301L (sv) * | 1976-04-08 | 1977-10-09 | Endo Lab | Trans-hexahydro-pyrido-indoler |
-
1979
- 1979-07-30 US US06/061,573 patent/US4252811A/en not_active Expired - Lifetime
-
1980
- 1980-06-18 DK DK260080A patent/DK148140C/da not_active IP Right Cessation
- 1980-07-18 CH CH552180A patent/CH644379A5/fr not_active IP Right Cessation
- 1980-07-24 SU SU802955229A patent/SU1172450A3/ru active
- 1980-07-25 CS CS805260A patent/CS221974B2/cs unknown
- 1980-07-28 JP JP10353280A patent/JPS5626891A/ja active Granted
- 1980-07-28 KR KR1019800003000A patent/KR840000914B1/ko active IP Right Grant
- 1980-07-28 NZ NZ194467A patent/NZ194467A/en unknown
- 1980-07-28 GR GR62556A patent/GR69664B/el unknown
- 1980-07-28 GB GB8024682A patent/GB2055372B/en not_active Expired
- 1980-07-28 AR AR281942A patent/AR226314A1/es active
- 1980-07-28 DE DE19803028555 patent/DE3028555A1/de not_active Ceased
- 1980-07-28 DD DD80222915A patent/DD153691A5/de unknown
- 1980-07-28 LU LU82662A patent/LU82662A1/fr unknown
- 1980-07-28 PL PL1980225940A patent/PL133456B1/pl unknown
- 1980-07-29 AU AU60869/80A patent/AU513948B2/en not_active Ceased
- 1980-07-29 IE IE1576/80A patent/IE50035B1/en unknown
- 1980-07-29 PH PH24365A patent/PH22657A/en unknown
- 1980-07-29 PT PT71623A patent/PT71623B/pt unknown
- 1980-07-29 IL IL60695A patent/IL60695A/xx unknown
- 1980-07-29 NL NLAANVRAGE8004332,A patent/NL180216C/xx not_active IP Right Cessation
- 1980-07-29 YU YU1917/80A patent/YU42223B/xx unknown
- 1980-07-29 ZA ZA00804604A patent/ZA804604B/xx unknown
- 1980-07-29 NO NO802274A patent/NO153729C/no unknown
- 1980-07-29 ES ES493818A patent/ES8105732A1/es not_active Expired
- 1980-07-29 BE BE0/201571A patent/BE884530A/fr not_active IP Right Cessation
- 1980-07-29 FR FR8016698A patent/FR2463140A1/fr active Granted
- 1980-07-29 SE SE8005453A patent/SE438505B/sv not_active IP Right Cessation
- 1980-07-29 CA CA357,265A patent/CA1133483A/en not_active Expired
- 1980-07-29 IT IT23785/80A patent/IT1194815B/it active
- 1980-07-29 AT AT0393280A patent/AT375659B/de not_active IP Right Cessation
- 1980-07-29 FI FI802371A patent/FI68828C/fi not_active IP Right Cessation
- 1980-07-30 EG EG458/80A patent/EG14903A/xx active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: PFIZER INC. |