FI61484C - Foerfarande foer framstaellning av z-3-(4-bromfenyl)-n-metyl-3-(3-pyridyl)-allylamin med antidepressiv och aongestdaempande verkan - Google Patents
Foerfarande foer framstaellning av z-3-(4-bromfenyl)-n-metyl-3-(3-pyridyl)-allylamin med antidepressiv och aongestdaempande verkan Download PDFInfo
- Publication number
- FI61484C FI61484C FI753260A FI753260A FI61484C FI 61484 C FI61484 C FI 61484C FI 753260 A FI753260 A FI 753260A FI 753260 A FI753260 A FI 753260A FI 61484 C FI61484 C FI 61484C
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- FI
- Finland
- Prior art keywords
- bromophenyl
- methyl
- compound
- pyridyl
- formula
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (1)
- 28 61 484 Säsom framgär ur tabellen har föreningen enligt formeln (I) en kraftig inhiberande verkan pä upptaget av 5-hydroxitryptamin och noradrenalin i neuroner. Föreningarna uppvisar en kraftigare in-hibering av 5-HT-upptaget in vivo än nägon annan av de testade tidigare kända föreningarna. Dessutom har föreningen enligt formeln (I), som testades som hydro-klorid, en kraftigare inhibering av 5-HT-upptaget in vitro än nägon annan av de testade, tidigare kända föreningarna. (Skillnaden mellan oxalatet och hydrokloriden torde bero pä det, att hydrokloriden framställdes ur oxalatet, varvid erhölls en renare Z-isomer). In-hiberingen av upptaget av 5-hydroxitryptamin och noradrenalin i neuroner kan ge föreningen enligt uppfinningen värde som anti-depressivt medel. Likaledes kan föreningen enligt uppfinningen vara användbar som ängestdämpande medel. Patenttivaatimus Menetelmä lääkeaineena käytettävän Z-3-(4-bromifenyyli)-N-metyyli- 3-(3-pyridyyli)-allyyliamiinin, jolla on kaava Br ί chch2n \ CH3 tai sen farmaseuttisesti hyväksyttävän suolan valmistamiseksi, tunnettu siitä, että a) dehydratoidaan 3-(4-bromifenyyli)-3-hydroksi-N-metyyli-3-(3-pyridyyli)-propyyliamiinia, jolla on kaava 0H^[ CH2-CH2N/ CH3 61484 29 b) monometyyliamiini alkyloidaan 3-(^-bromifenyyli)-3-(3-pyri-dyyli)-allyylijohdannaisella, jolla on kaava . Br i^ji j^T II CHCH2-Y jossa Y on lohkaistavissa oleva ryhmä, kaavan I mukaisen yhdisteen muodostamiseksi, c) 3-(^f-bromifenyyli )-3~ ( 3-pyr’idyyli )-allyyliamiinin, jolla on kaava Γ^'Χ Br s CHCH2NH2 viedään sinänsä tunnetulla tavalla metyyliryhmä kaavan I mukaisen yhdisteen muodostamiseksi, tai d) 3~(k-bromifenyyli)-3-hydroksi-N-metyyli-3-(3-pyridyyli)-propyyliamiinin asyyli- tai sulfonyyliyhdistettä, jolla on kaava / C\ HO CH2CH2-NCH3-Z jossa kaavassa Z on asyyli- tai sulfonyyliryhmä, käsitellään hydrolysoivissa olosuhteissa, jolloin muodostuu kaavan I mukainen yhdiste joko suoraan tai tyydyttämättömän asyyli- tai sulfonyyliyhdis-teen välityksellä, minkä jälkeen jollakin menetelmistä a) - d) saatu yhdiste mahdollisesti muutetaan/erotetaan puhtaaksi Z-isomee-riksi ja mahdollisesti muutetaan farmaseuttisesti hyväksyttäväksi suolakseen. a . t 30 6 1 4 8 4 Förfarande för framställning av Z-3-(^-bromfenyl)-N-metyl-3-(3-pyridyl)-allyl-amin tili användning soin läkemedel enligt forme In Il /H CHCH0N ^ CH3 eller ett farmaceutiskt acceptabelt sait därav, kanne-tecknat av att man a) dehydratiserar 3-(4-bromfenyl)-2-hydroxi-N-metyl-3-(3-pyridyl)-propylamin . Br H ΠΓ c I H OH I CH2-CH2N ^ CHj tili bildning av en förening enligt formel I, b) alkylerar monometylamin med ett 3-(^-bromfenyl)-3-(3-pynidyl)-allylderivat enligt formeln i CHCH2-Y där Y är en avspaltbar grupp tili bildning av en förening enligt formel I, c) inför en metylgrupp pä i och för sig känt sätt i 3-(^-brom-fenyl)-3-(3-pyridyl)-allylamin enligt formeln
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI811434A FI811434L (fi) | 1974-11-21 | 1981-05-11 | Foereningar till anvaendning som mellanprodukter foer framstaellning av terapeutiskt vaerdefulla fenylpyridylallylaminer och deras salter |
| FI813271A FI64353C (fi) | 1974-11-21 | 1981-10-20 | Foerfarande foer framstaellning av e-3-(4-bromfenyl)-n-metyl-3-(3-pyridyl)-allylamin till anvaendning som laekemedel |
| FI824476A FI824476L (fi) | 1974-11-21 | 1982-12-27 | 3-(4-bromfenyl)-3-(3-pyridyl)-allylamin och salter daerav till anvaendning som mellanprodukter foerframstaellning av terapeutiskt vaerdefulla fenyl- pyridyl-allylaminer |
| FI824475A FI824475L (fi) | 1974-11-21 | 1982-12-27 | 3-(4-bromfenyl)-3-(3-pyridyl)-allylderivat och salter daerav till anvaendning som mellanprodukter fframstaellning av terapeutiskt vaerdefulla fenyl- pyridyl-allylaminer |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7414622A SE388854B (sv) | 1974-11-21 | 1974-11-21 | Forfarande for framstellning av fenylpyridylaminderivat |
| SE7414622 | 1974-11-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI753260A FI753260A (sv) | 1976-05-22 |
| FI61484B FI61484B (fi) | 1982-04-30 |
| FI61484C true FI61484C (fi) | 1982-08-10 |
Family
ID=20322772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI753260A FI61484C (fi) | 1974-11-21 | 1975-11-19 | Foerfarande foer framstaellning av z-3-(4-bromfenyl)-n-metyl-3-(3-pyridyl)-allylamin med antidepressiv och aongestdaempande verkan |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5176278A (sv) |
| AR (2) | AR211921A1 (sv) |
| AT (1) | AT346328B (sv) |
| AU (1) | AU501915B2 (sv) |
| BE (1) | BE835802A (sv) |
| CA (1) | CA1056834A (sv) |
| CH (4) | CH614937A5 (sv) |
| DD (1) | DD122528A5 (sv) |
| DE (1) | DE2550005A1 (sv) |
| DK (1) | DK147179C (sv) |
| ES (4) | ES442758A1 (sv) |
| FI (1) | FI61484C (sv) |
| FR (1) | FR2291751A1 (sv) |
| GB (1) | GB1530804A (sv) |
| HU (1) | HU171206B (sv) |
| IE (1) | IE42615B1 (sv) |
| IL (1) | IL48409A (sv) |
| LU (1) | LU73844A1 (sv) |
| NL (1) | NL7513648A (sv) |
| NO (1) | NO149775C (sv) |
| NZ (1) | NZ179247A (sv) |
| PL (2) | PL103999B1 (sv) |
| SE (1) | SE388854B (sv) |
| SU (1) | SU686614A3 (sv) |
| YU (1) | YU39153B (sv) |
| ZA (1) | ZA756893B (sv) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2857020A1 (de) * | 1977-07-04 | 1981-01-08 | Astra Laekemedel Ab | A novel intermediate for preparation of therapeutically active pyridine compounds |
| SE409860B (sv) * | 1977-07-04 | 1979-09-10 | Astra Laekemedel Ab | En ny mellanprodukt for framstellning av terapeutiskt aktiva pyridinforeningar |
| SE7909514L (sv) | 1979-11-16 | 1981-05-17 | Astra Laekemedel Ab | Nya halofenyl-pyridyl-allylaminderivat |
| US4312368A (en) * | 1980-02-20 | 1982-01-26 | Philip Morris, Incorporated | Smoking compositions |
| US5148817A (en) * | 1980-11-07 | 1992-09-22 | Philip Morris Incorporated | Smoking compositions |
| CA1150269A (en) * | 1980-11-14 | 1983-07-19 | Carl B. J. Ulff | Process for preparing 3-(4-bromophenyl)-3-(3-pyridyl)-allylamines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH83A (fr) * | 1888-11-17 | 1889-01-10 | Fontainemelon Horlogerie | Perfectionnements apportés à la construction des montres de tous calibres |
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1974
- 1974-11-21 SE SE7414622A patent/SE388854B/sv unknown
-
1975
- 1975-11-03 ZA ZA00756893A patent/ZA756893B/xx unknown
- 1975-11-04 IL IL48409A patent/IL48409A/xx unknown
- 1975-11-07 DE DE19752550005 patent/DE2550005A1/de not_active Withdrawn
- 1975-11-14 NZ NZ179247A patent/NZ179247A/xx unknown
- 1975-11-14 AU AU86627/75A patent/AU501915B2/en not_active Expired
- 1975-11-17 NO NO753849A patent/NO149775C/no unknown
- 1975-11-18 ES ES442758A patent/ES442758A1/es not_active Expired
- 1975-11-18 DK DK518175A patent/DK147179C/da not_active IP Right Cessation
- 1975-11-19 FI FI753260A patent/FI61484C/fi not_active IP Right Cessation
- 1975-11-19 YU YU02939/75A patent/YU39153B/xx unknown
- 1975-11-19 SU SU2189809A patent/SU686614A3/ru active
- 1975-11-19 DD DD189559A patent/DD122528A5/xx unknown
- 1975-11-20 AT AT882275A patent/AT346328B/de not_active IP Right Cessation
- 1975-11-20 HU HU75AA00000833A patent/HU171206B/hu unknown
- 1975-11-20 PL PL1975184867A patent/PL103999B1/pl unknown
- 1975-11-20 CA CA240,075A patent/CA1056834A/en not_active Expired
- 1975-11-20 FR FR7535539A patent/FR2291751A1/fr active Granted
- 1975-11-20 IE IE2530/75A patent/IE42615B1/en unknown
- 1975-11-20 GB GB47800/75A patent/GB1530804A/en not_active Expired
- 1975-11-20 PL PL1975205688A patent/PL103784B1/pl unknown
- 1975-11-21 BE BE162059A patent/BE835802A/xx not_active IP Right Cessation
- 1975-11-21 AR AR261304A patent/AR211921A1/es active
- 1975-11-21 NL NL7513648A patent/NL7513648A/xx not_active Application Discontinuation
- 1975-11-21 CH CH1512975A patent/CH614937A5/xx not_active IP Right Cessation
- 1975-11-21 JP JP50140102A patent/JPS5176278A/ja active Pending
- 1975-11-21 LU LU73844A patent/LU73844A1/xx unknown
-
1976
- 1976-09-21 AR AR264786A patent/AR210517A1/es active
- 1976-10-07 ES ES452171A patent/ES452171A1/es not_active Expired
- 1976-10-07 ES ES452173A patent/ES452173A1/es not_active Expired
- 1976-10-07 ES ES452172A patent/ES452172A1/es not_active Expired
-
1979
- 1979-01-05 CH CH9279A patent/CH615665A5/de not_active IP Right Cessation
- 1979-01-05 CH CH9379A patent/CH626065A5/de not_active IP Right Cessation
- 1979-01-05 CH CH9479A patent/CH626066A5/de not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: ASTRA LAEKEMEDEL AB |