FI85011B - Foerfarande foer framstaellning av farmakologiskt vaerdefulla fenetanolaminderivat. - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla fenetanolaminderivat. Download PDFInfo
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Claims (2)
1. Menetelmä valmistaa farmakologisesti arvokkaita fenetanoli-amiini johdannaisia, joiden kaava I on HOCH2 OH J \_ CHCH2NHC(CH2)m-0-(CH2)n-Ar (I) X=J jossa m on kokonaisluku 2 - 8 ja n on kokonaisluku 1 - 7 edellyttäen, että kokonaissumma m + n on 4 - 12; Ar on fenyy1iryhmä, joka valinnaisesti on substituoitu yhdellä tai kahdella substituenti11 a valittuna halogeeniatomeista, C1 - a alkyyli-ja C1-3 alkoksiryhmistä, ja R1 ja R2, jotka kukin voivat olla samoja tai erilaisia, tarkoittavat kukin vetyatomia tai C1-3 a 1 kyy 1iryhmää edellyttäen, että hiiliatomien kokonaismäärä ryhmissä R1 ja R2 ei ole enempää kuin 4; tai sen fysiologisesti hyväksyttävää suolaa tai hydraattia, tunnettu siitä, että (1) yleiskaavan (I) mukaisen yhdisteen, jossa R1 on vetyatomi valmistamiseksi alkyloidaan yleiskaavan (II) mukainen amiini R6OCH2 R50 _/ \ CHCH2NR3R4 (II) \=/ Ah jossa R3, R5 ja R6 tarkoittavat kukin vetyatomia tai suoja-ryhmää, esim. aralkyyli-, asyyli- tai pyranyy1iryhmää ja R4 on vetyatomi, 69 8501 1 a) yleiskaavan (III) mukaisella alkylointiaineella LCH(CH2)mO(CH2)nAr (Ml) R2 jossa m, n, R2 ja Ar tarkoittavat samaa kuin yleiskaavassa (I) ja L on poistuva ryhmä, esim. halogeeni tai hydroksikarbonyy1i-sulfonyy1ioksi ryhmä, b) tai yleiskaavan (IV) mukaisella yhdisteellä R2C0(CH2)m-0-(CH2)nAr (IV) jossa R2, m, n ja Ar tarkoittavat samaa kuin yleiskaavassa (I) pelkistimen läsnäollessa, minkä jälkeen poistetaan mahdollisesti läsnäolevat suojaryhmät; tai (2) pelkistetään yleiskaavan (VI) mukainen välituote X R50 X1-X2-x3-CH20CH2X4-Ar (VI) jossa Ar tarkoittaa samaa kuin yleiskaavassa (I), R* on vetyatomi tai edellä mainittu suojaryhmä ja ainakin yksi ryhmistä X, X1, X2, X3 ja X4 on pelkistyvä ryhmä, kuten esim. X on ryhmä -C02R7, jossa R7 on vetyatomi tai alkyyli-, aryyli-tai aralkyyliryhmä tai -CHO, X1 on ryhmä -C=0, X2 on ryhmä -CH2NY, jossa Y on ryhmä, joka voidaan muuntaa vedyksi tai imiini (-CH=N-)-ryhmä tai ryhmä -CONH-, ja X3 on ryhmä -C0(CH2)m-1, tai ryhmä -CR^zx»-, jossa X5 on C2-7 alkenyyli tai C2-7 alkynyleeni, tai X2-x3- on ryhmä -CH2N=CH2(CH2)m-1, ja X4 on C2-6 alkenyleeni tai C2-6 alkynyleeni ja jäljelle 70 8 501 1 jäänyt ryhmä tai ryhmät tarkoittavat: X on -CH2OR€, Xx on -CH(OH)-, X1 on -CH2NR3# ja X2 3 on -CRXR2(CH2)m-i ja X« on ~(CH2)n-1/ joissa R6, R2, R2, ri, m ja n tarkoittavat samaa kuin edellä, tai sen suojattu johdos, minkä jälkeen poistetaan mahdollisesti läsnäolevat suojaryhmät; tai (3) yleiskaavan (VII) mukainen yhdiste: RgQCH^ R40 -- Z jossa Z on ryhmä -CHCH2L tai -CH - CH2, 1 \ / OH O jolloin R4 ja R6, jotka voivat olla samoja tai erilaisia, tarkoittavat kukin vetyatomia tai suojaryhmää ja L on poistuva ryhmä, saatetaan reagoimaan yleiskaavan (VIII) mukaisen amiinin kanssa Ri i Y1NHC(CH2)m-0-(CH2)n-Ar (VIII) i R1 jossa Y1 on vetyatomi tai ryhmä, joka voidaan täksi muuntaa hydraamalla katalyyttisesti, ja R1, R1, m, n ja Ar tarkoittavat samaa kuin yleiskaavassa (I), minkä jälkeen poistetaan mahdollisesti läsnäolevat suojaryhmät; ja haluttaessa muunnetaan saatu yleiskaavan (I) mukainen yhdiste tai sen suola fysiologisesti sopivaksi suolakseen tai hydraatikseen. Patenttivaatimuksen 1 mukainen menetelmä, tunnettu 2 siitä, että valmistetaan 4-hydroksi-ax-[[[6-(4-fenyylibutoksi)- 3 heksyyli]amino]metyyli]-1,3-bentseenidimetanoli tai sen 4 fysiologisesti hyväksyttävä suola. n 8501 1
1. Förfarande för framställning av farmakologiskt värdefulla fenetanolaminderivat med formeln I HOCH2 -1 OH -(/ \\- CHCH2NHC(CH2)m-0-(CH2)n-Ar (I) \-/ OH R2 där m är heltalet 2-8 och n är heltalet 1-7 förutsatt, att totalsumman m + n är 4 - 12; Ar är en fenylgrupp, soin eventuellt är substituerad med en eller tvä substituenter valda bland haiogenatomer, Ci-3 alkyl- och C1-3 alkoxigrupper, och R1 och R2, som var och en kan vara lika eller olika, avser var och en en väteatom eller en C1-3 alkylgrupp förutsatt, att kol-atomernas totalantal i grupperna R1 och R2 inte är mera än 4; eller dess fysiologiskt godtagbara sait eller hydrat, kännetecknat därav, att (1) för framställning av en förening med den allmänna formeln (I), där R1 är en väteatom, alkyleras en amin med den allmänna formeln (II) R60CH2 R50 _/ v CHCH2NR3R4 (II) \=/ on där R3, R5 och R6 avser var och en en väteatom eller en skydds-grupp, t.ex. en aralkyl-, acyl- eller pyranylgrupp och R4 är en väteatom. 72 8501 1 a) med ett alkyleringsmedel med den allmänna formeln (III) LCH(CH2)m0(CH2)riAr (III) R2 där m, n, R2 och Ar avser det samma som i den allmänna formeln (I) och L är en avgäende grupp, t.ex. halogen eller en hydroxikarbonyl-sulfonyloxigrupp, b) eller med en förening med den allmänna formeln (IV) R2C0(CH2)m-0-(CH2)nAr (IV) där R2, m, n och Ar avser det samma som i den allmänna formeln (I) i närvaro av ett reduktionsmedel, varefter eventuella närvarande skyddsgrupper avlägsnas; eller (2) en mellanprodukt med den allmänna formeln (VI) X \_ R50 ~Cj~ X1-X2-X3-CH20CH2X4-Ar (VI) där Ar avser det samma som i den allmänna formeln (I), R5 är en väteatom eller ovan nämnda skyddsgrupp och ätminstone en av grupperna X, X1, X2, X3 och X4 är en reducerbar grupp, säsom t.ex. X är en grupp -CO2R7, där R7 är en väteatom eller en alkyl-, aryl- eller aralkylgrupp eller -CHO, X1 är en grupp -C=0, X2 är en grupp -CH2NY, där Y är en grupp, som kan omvandlas till väte eller en imin (-CH=N-)-grupp eller en grupp -CONH-, och X3 är en grupp -C0(CH2)m-i, eller en grupp -CR1R2X5-, där X5 är en C2-7 alkenyl eller C2-7 alkynylen, eller X2-X3- är en grupp -CH2N=CH2(CH2)m-i, och X4 är C2-6 73 8501 1 alkenylen eller C2-6 alkynylen och den kvarvarande gruppen eller grupperna avser: X är -CH2OR6, X1 är -CH(OH)-, X1 är -CH2NR2 3, och X2 är -CR1R1(CH2)m-i och X* är -(CH2)n-l, där R«, R2, R1, R2, m och n avser det samma som ovan, eller dess skyddad derivat recuderas, varefter eventuella närvarande skydds-grupper avlägsnas; eller (3) en förening med den allmänna formeln (VII): R6OCH2 R40 -- Z där Z är en grupp -CHCH2L eller -CH - CH2, I \ / OH O varvid R4 och R6, som kan vara lika eller olika, avser var och en en väteatom eller en skyddsgrupp och L är en avgäende grupp, omsätts med en amin med den allmänna formeln (VIII) R1 YiNHC(CH2)m-0-(CH2)n-Ar (VIII) R2 där Y1 är en väteatom eller en grupp, som kan omvandlas till en sädan genom katalytisk hydrering, och R1, R1, m, n och Ar avser det samma i som den allmänna formeln (I), varefter eventuella närvarande skyddsgrupper avlägsnas; och vid behov omvandlas den erhällna förening en med den allmänna formeln (I) eller dess salt till ett fysiologiskt lämpligt salt eller hydrat. Förfarande enligt patentkravet 1, kännetecknat 2 därav, att man framställer 4-hydroxi-a1-[[[6-(4-fenylbutoxi)- 3 hexyl]amino]mety1]-l,3-bensendimetanol eller dess fysiologiskt 4 godtagbara salt.
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
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GB838310477A GB8310477D0 (en) | 1983-04-18 | 1983-04-18 | Chemical compounds |
GB8310477 | 1983-04-18 | ||
GB838317087A GB8317087D0 (en) | 1983-06-23 | 1983-06-23 | Chemical compounds |
GB8317087 | 1983-06-23 | ||
GB838329568A GB8329568D0 (en) | 1983-11-04 | 1983-11-04 | Chemical compounds |
GB8329568 | 1983-11-04 | ||
GB848401889A GB8401889D0 (en) | 1984-01-25 | 1984-01-25 | Chemical compounds |
GB8401889 | 1984-01-25 |
Publications (4)
Publication Number | Publication Date |
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FI841548A0 FI841548A0 (fi) | 1984-04-18 |
FI841548A FI841548A (fi) | 1984-10-19 |
FI85011B true FI85011B (fi) | 1991-11-15 |
FI85011C FI85011C (sv) | 1992-02-25 |
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Application Number | Title | Priority Date | Filing Date |
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FI841548A FI85011C (sv) | 1983-04-18 | 1984-04-18 | Förfarande för framställning av farmakologiskt värdefulla fenetanolami nderivat |
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US (5) | US4992474A (sv) |
JP (2) | JPS63264443A (sv) |
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DK (2) | DK167493B1 (sv) |
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FI (1) | FI85011C (sv) |
FR (1) | FR2545482B1 (sv) |
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NO (2) | NO159016C (sv) |
NZ (2) | NZ207885A (sv) |
PH (1) | PH21574A (sv) |
PT (1) | PT78443B (sv) |
SE (1) | SE462594B (sv) |
SG (1) | SG12289G (sv) |
SK (1) | SK278120B6 (sv) |
ZW (1) | ZW6584A1 (sv) |
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1991
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Spc suppl protection certif: L13 Extension date: 20051025 |
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Owner name: GLAXO GROUP LIMITED |