FI93350B - Förfarande för framställning av nya farmakologiskt aktiva katekolderivat - Google Patents

Förfarande för framställning av nya farmakologiskt aktiva katekolderivat Download PDF

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Publication number
FI93350B
FI93350B FI875229A FI875229A FI93350B FI 93350 B FI93350 B FI 93350B FI 875229 A FI875229 A FI 875229A FI 875229 A FI875229 A FI 875229A FI 93350 B FI93350 B FI 93350B
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Finland
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formula
dihydroxy
compound
yield
cyano
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FI875229A
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English (en)
Finnish (fi)
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FI875229A0 (sv
FI93350C (sv
FI875229A (sv
Inventor
Reijo Johannes Baeckstroem
Kalevi Evert Heinola
Erkki Juhani Honkanen
Seppo Kalevi Kaakkola
Pekka Juhani Kairisalo
Inge-Britt Yvonne Linden
Pekka Topias Maennistoe
Erkki Aarne Olavi Nissinen
Pentti Pohto
Aino Kyllikki Pippuri
Jarmo Johan Pystynen
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Orion Yhtymae Oy
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Priority to FI875229A priority Critical patent/FI93350C/sv
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Publication of FI875229A publication Critical patent/FI875229A/sv
Publication of FI93350B publication Critical patent/FI93350B/sv
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Publication of FI93350C publication Critical patent/FI93350C/sv

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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
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Claims (7)

1. Förfarande för framställning av nya farmakologisi aktiva katekolderivat med formeln I, RiO>._ R2°—^ y/””3 1 X väri R1 ooh R2, obaroende av varandra betecknar väte, alkylkarbonyl, fenylkarbonyl, eller lägre alkoxialkylkarbamoyl, X betecknar halogen, nitro eller cyano och R3 betecknar fenylalkenoyl, eventuellt substituerad med dialkylamino eller R3 betecknar alkyl, som är substituerad med en av följande grupper: alkoxialkoxi-eller karboxi alkyltio eller pyrrol eller Rs betecknar en grupp utvald bland /R4 ,R4 -CH=C^ -CH2CH R5 eller Krs väri R4 betecknar väte, cyano, alkyl eller alkylkarbonyl och Rg betecknar cyano, nitro, hydroxialkyl, alkylkarbonyl, alkoxikarbonyl eller karbamoyl, eventuellt substituerad med alkyl eller hydroxialkyl eller fenylkarbonyl, som är substituerad med 1-3 alkoxi, karboxi eller nitro eller grupp COZ, väri Z betecknar piperazinring, eventuellt substituerad med alkyl, förutsatt att R4 inte är väte eller alkyl när Rs betyder alkylkarbonyl eller alkoxikarbonyl, eller R4 och Rs bildar tillsammans en 5 tili 7 , . ledad cycloalkanonring, som är subsituerad med en benzylideniring, som är subsituerad med nitro och/eller hydroxi eller R3 betecknar -(CH2)m-COR väri m är 4 och R betecknar hydroxi, alkoxi eller amino, som är substituerad med alkyl, alkynyl eller adamantyl eller piperazin, som är eventuellt substiterad med fenylalkylgrupp; eller R3 betecknar grupp Π Λ -c~\ M 93350 väri R0 betecknar väte, RQ betecknar adamantyl eller fenylalkyl eller vari Ra 8 9 3 och Rg bildar tillsammans en piperidylgrupp, som eventuellt är substituerad med cycloalkylkarbonyl, med undantag av 3-(3,4-dihydroxi-5-nitrofeny 1)-1-propanol kännetecknat avatt metoden innefattar att man a) läter föreningen med formeln Γ R1°N._ r2o—^ \—R3' I X väri R , R och X har ovan angiven betydelse och väri R betecknar aldehyd reagera vid närvaro av syra- eller baskatalysator med en aktiv metyl- eller metylengrupp med formeln IV, ✓R4 CH, IV X vari R4 och R5 har ovan angiven betydelse varvid man ästadkommer föreningar med formeln la, RiO _^=\_ /R* r2°~^ la X vari R^ R2, X, R4och Rg harovan angiven betydelse och vari : dubbelbindningen eventuellt kan reduceras till en enkelbindning eller b) läter föreningen med formeln Γ R1°V._ R20“^ 1 x vari R3 betecknar grupp -COCH3 reagera vid närvaro av syra- eller baskatalysator med en aldehyd med formeln V, II 55 93350 -”7 0cH~O van R7 betecknar väte eller dialkylamino varvid man ästadkommer föreningar med formeln lb, R^>=\J Ib vari Rr R2> Xoch Ry har ovan angiven betydelse c) läter föreningen med formeln Γ RiO. _ R2°—^ jb-R3* Γ X Rg' betyder grupp -COY, väri Y betecknar halogen eller nägon annan aktiverande grupp, reagera med en amin med formeln VI, ✓Re HN VI s R9 vari R8 och Rg har ovan angiven betydelse, varvid man ästadkommer ’ föreningar med formeln Ic, RiO^ >=\ H /R° *yjc~u'*, x .: vari R1, R2, X, Rg och Rg har ovan angiven betydelse eller d) läter föreningen med formeln Γ vari R3' betecknar grupp -CH2OH reagera 1. med en alkohol med formeln VII, HO-R' VII 56 93350 väri R' betecknar en alkyl som är substituerad med alkoxi varvid man ästadkommer föreningar med formeln Id, R'°\_ R20—^ \ CH2OR' Id HL, väri R1, R2, R' och X har ovan angiven betydelse eller 2. med en tiol med formeln Vili, HS-R" Vili väri R" betecknar en alkyl som är substituerad med karboxi varvid man ästadkommer föreningar med formeln le R1<N=\ R20—^ CH2SR" Ie X^ väri Rr R2, R”och X har ovan angiven betydelse eller 3. med en pyrrol med formeln IX, o H varvid man ästadkommer föreningar med formeln If, X H väri R1, R2 och X har ovan angiven betydelse eller e) aminerar eller förestrar föreningen med formeln I väri R3 betecknar -(CH2)4COOH ti 57 93350 varvid man ästadkommar en förening mad formaln I väri R1( R2och X har ovan angivan batydalsa och R3 batacknar -(CH2)4COR väri R har ovan angivan batydalsa allar f) man daalkylarar förening mad formaln Γ Rl'°v _ R2O-^ ^-R3 Γ X väri dan ena av gruppama Ri' och R2' batacknar alkyi och dan andra batacknar väta allar alkyi varvid man ästadkommer an förening mad formaln I väri R-ι och R2 batacknar väta och X och Ra har ovan angivan batydalsa g) man reducerar förening mad formaln Γ RiO. _ R20—/ \ R3’ 1' X väri R3' batacknar grupp /CH3 —CH=C ; XOCHj tili förening mad formaln I väri R1, R2och X har ovan angivan batydalsa och R3 batacknar -CH=c' ΌΗ2ΟΗ j) evantuallt förestrar föraningan mad formaln I väri R1 och R2 batacknar väta alter man hydrolysarar förening mad formaln I väri Ri allar/och R2 batacknar alkylkarbonyl. 93350 58
2. Förfarandeenligtpatentkravet l.kännetecknat avatt man startar med förening med formeln Γ, van Ri’ och/eller R2' betecknar en alkyl grupp, och hydrolyserar denna eller dessa för att ästadkomma motsvarande fria slutprodukt med formeln I.
3. Förfarande enligt patentkravet l.kännetecknat av att R3 betecknar yR4 —CH=C^ R5 väri R betecknar cyano eller alkylkarbonyl och R betecknar cyano, alkylkarbonyl, hydroxialkyl, alkoxikarbonyl eller substituerad karbamoyl eller fenylkarbonyl eller grupp COZ, väri Z betecknar eventuellt substituerad piperazinring.
4. Förfarande enligt patentkravet 3, kännetecknat av att R4 och Rg betecknar alkylkarbonyl.
5. Förfarande enligt patentkravet 4, kännetecknat av att föreningen som skall framställas är 3-(3,4-dihydroxi-5-nitrobentsyliden)-2,4-pentandion.
6. Förfarande enligt patentkravet 3, kännetecknat av att R betecknar cyano och R betecknar subsituerad karbamoyl, alkoxikarbonyl 4 b eller hydroxialkyl.
7. Förfarande enligt patentkravet 6, k ä n n e t e c k n a t av att föreningen som skall framställas är utvald bland N,N-dimetyl-2-cyano-3-(3,4-dihydroxi-nitrofenyl)akrylamid, N,N-dietyl-2-cyano-3-(3,4-dihydroxi-nitrofenyl)akrylamid N-isopropyl-2-cyano-3-(3,4-dihydroxi-nitrofenyl)akrylamid, etyl 2-cyano-3-(3,4-dihydroxi-nitrofenyl)akrylat, neopentyl-2-cyano-3-(3,4-dihydroxi-nitrofenyl)akrylat eller N-(3-hydroxipropyl)-2-cyano-3-(3,4-dihydroxi-nitrofenyl)akrylamid. Il
FI875229A 1986-11-28 1987-11-27 Förfarande för framställning av nya farmakologiskt aktiva katekolderivat FI93350C (sv)

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