YU48020B - Postupak za dobijanje novih farmakoloških aktivnih ketholnih derivata - Google Patents

Postupak za dobijanje novih farmakoloških aktivnih ketholnih derivata

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Publication number
YU48020B
YU48020B YU2189A YU2189A YU48020B YU 48020 B YU48020 B YU 48020B YU 2189 A YU2189 A YU 2189A YU 2189 A YU2189 A YU 2189A YU 48020 B YU48020 B YU 48020B
Authority
YU
Yugoslavia
Prior art keywords
cyano
compound
acyl
optionally substituted
formula
Prior art date
Application number
YU2189A
Other languages
English (en)
Other versions
YU2189A (en
Inventor
R.J. Backstrom
K.E. Heinola
E.J. Honkanen
S.K. Kaakkola
P.J. Kairsalo
I-B.Y. Linden
P.T. Mannistro
E.A.O. Nissinen
P. Pohto
A.K. Ippuri
J.J. Pystynen
Original Assignee
Orion-Yhtymaoy Saunatontuntie
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26158050&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=YU48020(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from FI864875A external-priority patent/FI864875A0/fi
Application filed by Orion-Yhtymaoy Saunatontuntie filed Critical Orion-Yhtymaoy Saunatontuntie
Publication of YU2189A publication Critical patent/YU2189A/xx
Priority to HR921250A priority Critical patent/HRP921250B1/xx
Publication of YU48020B publication Critical patent/YU48020B/sh

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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms
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Abstract

POSTUPAK ZA DOBIJANJE NOVIH FARMAKOLOSKIH AKTIVNIH KETHOLNIH DERIVATA, formule I u kojoj R1 i R2 nezavisno predstavljaju vodonik, po izboru supstituisani acil ili po izboru supstituisani aroil, X je elektronegativni supstituent kao sto je halogen, nitro, cijano, i R3 je gde R4 predstavlja vodonik, alkil, cijano ili acil i R5 predstavlja cijano, karboksil, alkoksikarbonil, alkoksikarbonilalkil, kar-boksialkilkarbonil, nitro, acil, hidroksialkil, COZ gde Z je po izboru supstituisani heterociklicni prsten ili jedna od sledecih po izboru supstituisanih grupa: karbamoil, aroil ili heteroaril, ili R4 i R5 zajedno obrazuju pet do sedmoclani supstituisani cikloalkanonski prsten, naznacen time, sto se kiselinski ili bazno katalizuje reakcija kondenzacije jedinjenja formule II u kojoj R1, R2 i X imaju napred definisana znacenja, sa jedinjenjem formule III koje ima aktivnu metil ili metilen grupu i u kojoj R4 i R5 su kao sto je prethodno definisano, tako da nastaje jedinjenje formule Ia pri cemu kada R4 je vodonik ili cijano i R5 je heteroaril, karboksi, nitro, alkoksikarbonil ili R4 i R5 oba su cijano, tada se jedinjenja II i III najpre zagrevaju u piridinu na 80°C ili refluktuju u anhidridu sircetne kiseline ili nizem alkoholu posle cega se smesa zakiseli hlorovodonicnom kiselinom, ili kada R4 je vodonik, alkil ili acil i R5 je acil, karboksialkilarbonil ili alkoksikarbonilalkil ili po izboru supstituisan aroil, ili R4 i R5 zajedno obrazuju pet do sedmoclani supstituisan cikloalkanon prsten, tada se jedinjenja II i III mesaju i dodaje se gasoviti hlorovodonik ili se ona rastvaraju u tetrahidrofuranu ili nizem alkoholu ili nizem alkanonu uz dodavanje gasovitog hlorovodonika, i kad R4 je cijano i R5 je po izboru supstituisan karbamoil ili je COZ gde Z je po izboru supstituisan heterocik-licni prsten tada se jedinjenja formule II i III kondenzuju uz upotrebu piperidin acetata kao katalizatora, posle cega ovako dobiveno jedinjenje moze da se, po potrebi, esterifikuje refluk-tujuci sa odgovarajucim anhidridom kiseline ili sa odgovarajucim hloridom kiseline u tetrahidrofuranu ili u diok-sanu, ili jedinjenje u kojem R4 je vodonik i R5 je acil moze da se redukuje sa natrijum borhidridom u jedinjenje u kojem R5 je hidroksialkil, ili jedinjenje u kojem R4 je cijano i R5 je cijano ili alkoksikarbonil moze da se redukuje sa natrijum bor-hidridom u jedinjenje u kojem R3 je -CH2-CHR4R5 gde R4 je cijano i R5 je cijano ili alkoksikarbonil.
YU2189A 1986-11-28 1989-01-06 Postupak za dobijanje novih farmakoloških aktivnih ketholnih derivata YU48020B (sh)

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FI864875A FI864875A0 (fi) 1986-11-28 1986-11-28 Nya farmakologiskt aktiva foereningar, dessa innehaollande kompositioner samt foerfarande och mellanprodukter foer anvaendning vid framstaellning av dessa.
GB878712437A GB8712437D0 (en) 1986-11-28 1987-05-27 Pharmacologically active compounds

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IT8722790A0 (it) 1987-11-27
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LU87050A1 (fr) 1988-05-03
CA1289078C (en) 1991-09-17
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HK75594A (en) 1994-08-12
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PL269091A1 (en) 1988-12-08
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AT401053B (de) 1996-06-25
PT86236A (en) 1987-12-01
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EG18338A (en) 1992-09-30
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NL300136I2 (nl) 2004-02-02
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YU47790B (sr) 1996-01-09
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MTP1012B (en) 1988-10-18
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