FI61484B - 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 PDF

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Publication number
FI61484B
FI61484B FI753260A FI753260A FI61484B FI 61484 B FI61484 B FI 61484B FI 753260 A FI753260 A FI 753260A FI 753260 A FI753260 A FI 753260A FI 61484 B FI61484 B FI 61484B
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Finland
Prior art keywords
bromophenyl
formula
pyridyl
compound
methyl
Prior art date
Application number
FI753260A
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English (en)
Finnish (fi)
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FI61484C (fi
FI753260A (sv
Inventor
Per Arvid Emil Carlsson
Bernt Sigfrid Emanuel Carnmalm
Svante Bertil Ross
Carl Bengt Johan Ulff
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Astra Laekemedel Ab
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Application filed by Astra Laekemedel Ab filed Critical Astra Laekemedel Ab
Publication of FI753260A publication Critical patent/FI753260A/fi
Priority to FI811434A priority Critical patent/FI811434L/fi
Priority to FI813271A priority patent/FI64353C/fi
Publication of FI61484B publication Critical patent/FI61484B/fi
Application granted granted Critical
Publication of FI61484C publication Critical patent/FI61484C/fi
Priority to FI824475A priority patent/FI824475A0/fi
Priority to FI824476A priority patent/FI824476L/fi

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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
    • 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
    • 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
    • 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
    • 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
    • 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

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  • 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)

  1. 61 484 28 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 I! "/H 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^jl jitpT !i 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 iT^jL ΓΎBr 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 /« 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 n j^r 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
FI753260A 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 FI61484C (fi)

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
FI824475A FI824475A0 (fi) 1974-11-21 1982-12-27 3-(4-bromfenyl)-3-(3-pyridyl)-allylderivat och salter daerav till anvaendning som mellanprodukter f framstaellning av terapeutiskt vaerdefulla fenyl- pyridyl-allylaminer
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

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 true FI61484B (fi) 1982-04-30
FI61484C 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) PL103784B1 (sv)
SE (1) SE388854B (sv)
SU (1) SU686614A1 (sv)
YU (1) YU39153B (sv)
ZA (1) ZA756893B (sv)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE409860B (sv) * 1977-07-04 1979-09-10 Astra Laekemedel Ab En ny mellanprodukt for framstellning av terapeutiskt aktiva pyridinforeningar
DE2857020A1 (de) * 1977-07-04 1981-01-08 Astra Laekemedel Ab A novel intermediate for preparation of therapeutically active pyridine compounds
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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
NO149775C (no) 1984-06-20
JPS5176278A (en) 1976-07-01
FR2291751A1 (fr) 1976-06-18
ES442758A1 (es) 1977-04-01
AU501915B2 (en) 1979-07-05
SU686614A3 (ru) 1979-09-15
DD122528A5 (sv) 1976-10-12
CH615665A5 (en) 1980-02-15
NL7513648A (nl) 1976-05-25
AU8662775A (en) 1977-05-19
CH626066A5 (en) 1981-10-30
BE835802A (fr) 1976-05-21
HU171206B (hu) 1977-12-28
CA1056834A (en) 1979-06-19
PL103784B1 (pl) 1979-07-31
AR210517A1 (es) 1977-08-15
AT346328B (de) 1978-11-10
ZA756893B (en) 1976-10-27
NO149775B (no) 1984-03-12
CH626065A5 (en) 1981-10-30
YU293975A (en) 1982-08-31
FR2291751B1 (sv) 1979-09-21
NO753849L (sv) 1976-05-24
AR211921A1 (es) 1978-04-14
NZ179247A (en) 1978-03-06
FI61484C (fi) 1982-08-10
ES452173A1 (es) 1977-10-01
IE42615B1 (en) 1980-09-10
PL103999B1 (pl) 1979-07-31
DE2550005A1 (de) 1976-05-26
ES452171A1 (es) 1977-10-01
ATA882275A (de) 1978-03-15
IE42615L (en) 1976-05-21
DK147179B (da) 1984-05-07
LU73844A1 (sv) 1976-09-06
DK147179C (da) 1984-11-19
SE388854B (sv) 1979-03-26
ES452172A1 (es) 1977-10-01
FI753260A (sv) 1976-05-22
SE7414622L (sv) 1976-05-24
DK518175A (da) 1976-05-22
GB1530804A (en) 1978-11-01
IL48409A (en) 1979-10-31
CH614937A5 (en) 1979-12-28
IL48409A0 (en) 1976-01-30
SU686614A1 (en) 1979-09-15
YU39153B (en) 1984-06-30

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Owner name: ASTRA LAEKEMEDEL AB