FI80694B - Foerfarande foer framstaellning av teraoeutiskt aktiva 5,6,7,8-tetrahydroimidazo/1,5-a/pyridiner. - Google Patents

Foerfarande foer framstaellning av teraoeutiskt aktiva 5,6,7,8-tetrahydroimidazo/1,5-a/pyridiner. Download PDF

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FI80694B
FI80694B FI852399A FI852399A FI80694B FI 80694 B FI80694 B FI 80694B FI 852399 A FI852399 A FI 852399A FI 852399 A FI852399 A FI 852399A FI 80694 B FI80694 B FI 80694B
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formula
compound
reacted
hydrogen
alkyl
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FI852399A
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FI80694C (sv
FI852399L (fi
FI852399A0 (fi
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Leslie J Browne
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Ciba Geigy Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • 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
    • C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/30—Oestrogens
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • 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
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Claims (4)

1. Förfarande för framställning av terapeutiskt aktiva 5,6,7,8-tetrahydroimidazo[l,5-a]pyridiner med formeln I* < 7 / \=.l ‘W ·' · IN \/ i, i vilken formel Rj^ betecknar cyano, halogen, C1-C4-alkyl el-ler amino och R2 betecknar väte, fenyl-Cj-C^-alkyl, C^-C^-alkyltio eller C1-C4-alkoxikarbonyl, och deras stereoisome-rer, blandningar av stereoisomerer eller farmaceutiskt god-tagbara salter, kännetecknat därav, att d) en förening med formeln V / \ h* (y) • r · I II 'V' i. i vilken Rj^ och R2 betecknar detsamma som ovan i formeln I* och är halogen, omsätts med en bas, eller e) en förening med formeln VI 65 8 0 6 9 4 /X . I*’ · (VI) /\ I II ‘v./’ L i vilken formel och R2 betecknar detsamma som ovan i for-meln I* och X2 är halogen, omsätts med en bas, eller f) 1 en förenlng med formeln vii / \ • · 3SSSE2 · \A> • · ** \ (VII) / \ • · I II V i,· i vilken Rj' är en i en cyanogrupp överförbar grupp och R2 betecknar detsamma som ovan i formeln I*, ' överförs i en cyanogrupp med en av de följande överföringsreaktionerna: (1) en förenlng med formeln VII, väri Rj' är formyl, omsätts med hydrazinsyra, eller (2) en förening med formeln VII, väri R1' är karbamoyl eller Cj-^-alkylkarbamoyl, omsätts med ett dehydratiseringsmedel, eller g) en förening med formeln IX 66 8 0 6 9 4 A._. ϊ=° HÄX Jl (IX ) y \ I II V i. i vilken R-j^ betecknar detsamma som ovan i formeln I*, om-sätts i närvaro av ett reducerande medel, eller h) en förening med formeln Vllc / \ __ ^00H (Vllc) I II V k, i vilken och R2 betecknar detsamma som ovan i formeln I*, dekarboxyleras, eller i) en förening med formeln I /\=. \A./* y\ <*> I n V’ t> eller ett 7,8-dihydroderivat därav, väri betecknar det- II 67 80694 samma som ovan i formeln I* eller Mr hydroximetyl, reduceras eventuellt genom att reducera samtidigt substituenten R^_ = CH2OH till gruppen = CH3; och/eller (1) för framställning av en förening med formeln I*, väri R2 Sr väte, en förening med formeln I*, väri R2 är C-l-C^-alkoxikarbonyl, omsätts först med natriumhydroxid och sedan med klorvätesyra; (2) för framställning av en förening med formeln I*, väri R2 är C^-C^-alkyltio, den motsvarande föreningen med formeln I*, väri R2 är väte, omsätts med di-C1-C4-alkyldisulfid; (3) för framställning av en förening med formeln I*, väri R2 är C1-C4-alkoxikarbonyl, den motsvarande föreningen med formeln I*, väri R2 är väte, omsätts med C1-C4-alkylhalogenfor-miat; (4) för framställning av en förening med formeln I*, väri R! är amino, den motsvarande föreningen med formeln I*, väri Rj^ är karboxi, omsätts med hydrazinsyra; (5) för framställning av en förening med formeln I*, väri R2 är fenyl-Cj-C^-alkyl, den motsvarande föreningen med formeln I*, väri R2 är väte, omsätts med fenyl-C1-C4-alkylhalogenid; (6) för framställning av en förening med formeln I*, väri Rj är cyano, den motsvarande föreningen med formeln I*, väri Rx är halogen, omsätts med ett cyanidsalt; (7) för framställning av en förening med formeln I*, väri Rj^ är cyano, den motsvarande föreningen med formeln I*, väri R1 är amino, omsätts först med ett alkalinitritsalt och sedan med koppar(I)cyanid; och/eller ett erhället sait överförs i en fri förening eller ett annat sait och/eller en fri förening överförs i ett sait 68 80694 och/eller en enantiomerisk blandning, säsom ett racemat, uppdelas i optiska isomerer.
2. Förfarande för framställning av terapeutiskt aktiva 5,6,7,8-tetrahydroimidazo[l,5-a]pyridiner med formeln Ib i 7 /\ = .l '\λ> ·' · I II V tl i vilken formel Rj betecknar cyano eller C1-C4-alkyl och R2 är väte, fenyl-C1-C4-alkyl eller C1-C4-alkyltio, stereoiso-merer, blandningar av stereoisomerer eller farmaceutiskt godtagbara salter av dessa föreningar, känneteck-n a t därav, att d) en förening med formeln Vb · · / \ • · =S5 · x>4h/</ Λ (Vb) • · I H ’V* k i vilken Rx betecknar detsamma som ovan i formeln Ib och X1 Sr halogen, omsätts med en bas, eller e) en förening med formeln VIb li 69 80694 /\_. • · |V (VIb) /\ ι' · I ιι V’ il i vilken formel R-j^ och R2 betecknar detsamma som ovan i formeln Ib och X2 är halogen, omsätts med en bas, eller f) 1 en förening med formeln Vllb / \ • »SSSS5· • · R* \ (Vllb) S \ I N V* i»· i vilken R!' är en grupp eller rest, som kan överföras i en cyanogrupp och R2 betecknar detsamma som ovan i formeln Ib, R2' överförs i cyano med en av de följande överföringsreak-tionerna: (1) en förening med formeln Vllb, väri ' är halogen, omsätts med ett cyanidsalt, (2) en förening med formeln Vllb, väri R^' är karbamoyl eller C^-C^-alkylkarbamoyl, omsätts med ett starkt dehydra-tiseringsmedel, (3) en förening med formeln Vllb, väri är formyl, omsätts med hydrazinsyra, eller 70 80694 (4) en förening med formeln Vllb, väri R^' är amino, omsätts först med ett alkalinitritsalt och sedan med koppar(I)cya-nid, eller i) en förening med formeln Ia 7 / \==.» I II V* i. eller ett 7,8-dihydroderivat därav reduceras med väte i när-varo av en hydreringskatalysator och/eller (1) för framställning av en förening med formeln Ib, väri R2 är C1-C4-alkyltio, den motsvarande föreningen med formeln Ib, väri R2 är väte, omsätts med di-C^-C^-alkyldisulfid, och/eller ett erhället sait överförs i en fri förening eller ett annat sait och/eller en fri förening med en saltbildande grupp i ett sait och/eller en erhällen racemisk blandning uppdelas i enskilda enantiomerer.
3. Förfarande enligt patentkravet 1, känneteck- n a t därav, att man framställer 5-(p-cyanofenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin, eller ett farmaceutiskt godtagbart syraadditionssalt därav
4. Förfarande enligt patentkravet 2, känneteck- n a t därav, att man framställer 5-(p-cyanofenyl)-5,6,7,8-tetrahydroimidazo[l,5-a]pyridin, eller ett farmaceutiskt godtagbart syraadditionssalt därav. il
FI852399A 1984-06-20 1985-06-17 Förfarande för framställning av terapeutiskt aktiva 5,6,7,8-tetrahydro imidazo/1,5-a/pyridiner FI80694C (sv)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FI882863A FI83079C (sv) 1984-06-20 1988-06-15 Förfarande för framställning av terapeutiskt aktiva 5-fenyl-imidazo/1, 5-a/pyridiner

Applications Claiming Priority (2)

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US06/622,421 US4617307A (en) 1984-06-20 1984-06-20 Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors
US62242184 1984-06-20

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FI852399A0 FI852399A0 (fi) 1985-06-17
FI852399L FI852399L (fi) 1985-12-21
FI80694B true FI80694B (fi) 1990-03-30
FI80694C FI80694C (sv) 1990-07-10

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US (1) US4617307A (sv)
EP (1) EP0165904B1 (sv)
JP (1) JPS6112688A (sv)
KR (1) KR900008566B1 (sv)
AT (1) ATE62415T1 (sv)
AU (1) AU589565B2 (sv)
BG (7) BG60262B2 (sv)
CA (1) CA1276633C (sv)
CS (1) CS268672B2 (sv)
CY (1) CY1750A (sv)
DD (1) DD237510A5 (sv)
DE (1) DE3582452D1 (sv)
DK (1) DK170302B1 (sv)
DZ (1) DZ799A1 (sv)
ES (6) ES8702406A1 (sv)
FI (1) FI80694C (sv)
GR (1) GR851487B (sv)
HK (1) HK23494A (sv)
HU (1) HU202529B (sv)
IE (1) IE58070B1 (sv)
IL (1) IL75546A (sv)
MA (1) MA20459A1 (sv)
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NO (1) NO162467C (sv)
NZ (1) NZ212483A (sv)
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