CH504436A - Verfahren zur Herstellung von Estern - Google Patents

Verfahren zur Herstellung von Estern

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Publication number
CH504436A
CH504436A CH343170A CH343170A CH504436A CH 504436 A CH504436 A CH 504436A CH 343170 A CH343170 A CH 343170A CH 343170 A CH343170 A CH 343170A CH 504436 A CH504436 A CH 504436A
Authority
CH
Switzerland
Prior art keywords
carbon atoms
alkyl
radical
alk
pyridine
Prior art date
Application number
CH343170A
Other languages
English (en)
Inventor
Doyle Peter
Joseph Stacey Gilbert
Original Assignee
Ici Ltd
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
Priority claimed from GB54135/66A external-priority patent/GB1147068A/en
Application filed by Ici Ltd filed Critical Ici Ltd
Publication of CH504436A publication Critical patent/CH504436A/de

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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
    • C07D213/54—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
    • 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
    • C07D213/61—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
    • C07D213/60—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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen 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
    • C07D213/60—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
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description


  Verfahren zur Herstellung von Estern    Die Erfindung     betrifft        ein    Verfahren zur Herstellung  von neuen Estern, die entzündungshemmende,     schmerz-          stillende    und antipyretische Eigenschaften haben und die  Konzentration von Fibrinogen sowie von Cholesterin  und/oder Triglyceriden im Blut herabzusetzen vermögen  und somit für die     Behandlung    oder Prophylaxe von  Koronararterienkrankheit und Atherosklerose geeignet  sind.  



  Gemäss der Erfindung werden Ester der Formel I  
EMI0001.0005     
    in welcher X Wasserstoff, einen Alkyl- oder Alkoxyrest  mit höchstens 3 C-Atomen oder ein Halogenatom, Y  einen gegebenenfalls durch ein oder zwei Halogenatome  substituierten Phenylrest, RÚ Wasserstoff, einen Alkyl  rest mit höchstens 3 C-Atomen oder einen     Alkoxycarbo-          nylrest    mit höchstens 6 C-Atomen und R2 einen Alkyl  rest mit höchstens 5 C-Atomen bedeuten, Alk für einen  Alkylrest mit höchstens 3 C-Atomen steht und die Reste  Y und - C(Alk)RÚ - COORê nicht an benachbarte     C-          Atome    des Pyridinkerns gebunden sind, hergestellt.  



  Das     erfindungsgemässe        Verfahren        besteht        darin,    dass  man ein Pyridinderivat der Formel II  
EMI0001.0014     
    oder eine Alkalimetallverbindung davon, in welcher X,  Y, RÚ und R2 die obige Bedeutung besitzen und die  Reste Y und - C(Alk)RÚ-COORê nicht an benachbarte  C-Atome gebunden sind, entsprechend alkyliert.  



  Zweckmässig kann X z.B. ein Wasserstoffatom, ein  Methyl- oder Methoxyradikal oder ein Chlor- oder       Bromatom.    darstellen.  



       Als    Beispiele für das oder die Halogenatome, die  gegebenenfalls im Y-Radikal vorhanden sind, kann man  Fluor-, Chlor- und Bromatome erwähnen. Die Verbin  dungen, bei denen das Y-Radikal einen oder zwei     Halo-          gensubstituenten    enthält, stellen bevorzugte Verbindun  gen dar, weil sie im allgemeinen aktiver     sind,    als die  entsprechenden urisubstituierten Phenylderivate.  



  RÚ kann Wasserstoff oder ein Methyl-,     Methoxy-          carbonyl-    oder Äthoxycarbonylrest sein. Das Symbol  Alk kann z.B. das Methyl- oder Athylradikal darstellen.  



  Als Salze der Pyridinderivate sind insbesondere die  pharmazeutisch zulässigen Säureadditionssalze, wie z.B.  Hydrochloride, Hydrobromide, Sulfate oder Phosphate,  geeignet.  



  Die als Ausgangsprodukte verwendeten     Pyridinderi-          vate    der Formel II können nach an sich bekannten  Methoden hergestellt werden. Die Erfindung ist im  folgenden anhand von Ausführungsbeispielen näher  erläutert.  



  <I>Beispiel I</I>  Es wurden 3,0g     Dimethyl-3-(4-chlorphenyl)-2-me-          thoxypyrid-6-ylmalonat    1 Stunde mit Natriumhydrid  (0,4l g ; 501%-ige Dispersion, die vor Gebrauch zur  Ölentfernung gewaschen wurde) in 25 ml trockenen     Di-          methylformamide    verrührt. Dann wurden 2,5 ml     Me-          thyliodid    hinzugegeben, so     dass    eine milde     exotherme     Reaktion stattfand.

   Die     Mischung    wurde 1 Stunde bei       35-4011    C     gerührt,        dann        m-iit        :etwa    30     ml        Wasser        verdünnt         und unter     vermindertem    Druck erwärmt, um das über  schüssige Methyliodid abzudampfen. Der vorhandene  Feststoff wurde mit Äther herausgelöst, der dann 3 mal  mit Wasser gewaschen, an Natriumsulfat getrocknet und  zur Trockne eingedampft wurde. Der Rückstand wurde  aus Methanol in Gegenwart von Kohle umkristallisiert.

    Somit erhielt man farblose Prismen aus     Dimethyl-a-(3-          (4-chlorphenyl)-2-methoxypyrid-6-yl)-a-methylmalonat,     Smp. 106-107 C.    <I>Beispiel 2</I>    Nach dem Verfahren gemäss Beispiel 1,     mit    der  Abweichung, dass     Dimethyl-5-(4-chlorphenyl)pyrid-2-yl-          malonat    anstelle von     Dimethyl-3-(4-chlorphenyl)-2-me-          thoxypyrid-6-ylmalonat    verwendet wurde, erhielt man       Dimethyl-a-(5-(4-chlorphenyl)-pyrid-2-yl)-a-methylmalo-          nat.    Dieses wurde ber sein Hydrochlorid gereinigt, das  aus einer ätherischen Lösung der rohen Base     isoliert,

      in  die Base zurückverwandelt und aus Petroläther (Sdp. 60  80 C)     umkristallisiert    wurde. Die gereinigte Base hatte  einen Schmelzpunkt von 58,5-60 C.    <I>Beispiel 3</I>  Es wurden 0,247 g Natriumhydrid zu einer Lösung  von 1,5 g     Dimethyl-4-(4-chlorphenyl)-6-methoxypyrid-2-          ylmalonat    in 15 ml wasserfreien Dimethylformamids zu  gegeben. Die Mischung wurde in einer Stickstoffatmo  sphäre gerührt, bis kein Wasserstoff mehr entwickelt  wurde und die Auflösung vollendet war. Die klare  Lösung wurde dann mit Methyljodid (0,915 g) behandelt  und noch 1 Stunde bei Raumtemperatur     gerührt.    Die  gelbe Suspension wurde in 150m1 Wasser eingegossen  und 3mal mit Äthylacetat extrahiert.

   Die vereinigten  organischen Extrakte wurden mit Wasser gewaschen, an  Magnesiumsulfat getrocknet und unter vermindertem  Druck zu einem gelben Feststoff eingedampft. Der Fest  stoff wurde so weit wie möglich in Äther gelöst, und die       Mischuni    wurde durch eine Kolonne aus Tonerde  (Spence-Korngrösse   O   30 g) filtriert. Vom Filtrat  wurde das Lösungsmittel abgedampft. Somit erhielt man       Dimethyl-a-methyl-a-(4-(4-chlorphenyl)-6-methoxypyrid-          2-yl)malonat,    Smp. 118-120  C nach Umkristallisierung  aus Petroläther (Sdp. 80-100  C).

Claims (1)

  1. PATENTANSPRUCH Verfahren zur Herstellung von Estern der Formel EMI0002.0019 in welcher X Wasserstoff, einen Alkyl- oder Alkoxyrest mit höchstens 3 C-Atomen oder ein Halogenatom, Y einen gegebenenfalls durch ein oder zwei Halogenatome substituierten Phenylrest, RÚ Wasserstoff, einen Alkyl rest mit höchstens 3 C-Atomen oder einen Alkoxycar- bonylrest mit höchstens 6 C-Atomen und R2 einen Alkyl rest mit höchstens 5 C-Atomen bedeuten, Alk für einen Alkylrest mit höchstens 3 C-Atomen steht und die Reste Y und - C(Alk)RÚ - COORê nicht an benachbarte C- Atome des Pyridinkerns gebunden sind, dadurch gekenn zeichnet,
    dass man ein Pyridinderivat der Formel EMI0002.0024 oder eine Alkalimetallverbindung davon, in welcher X, Y, RÚ und R2 die obige Bedeutung besitzen und die Reste Y und - C(Alk)RÚ - COORê nicht an benachbarte C-Atome gebunden sind, entsprechend alkyliert. UNTERANSPRÜCHE 1. Verfahren nach Patentanspruch, dadurch gekenn zeichnet, dass die Alkylierung durch Umsetzung eines 1 bis 3 C-Atome enthaltenden Alkylhalogenids mit einer Alkalimetallverbindung des Pyridinderivates durchge- führt wird. 2.
    Verfahren nach Patentanspruch oder Unteran- spruch 1, dadurch gekennzeichnet, dass die Alkylierung in einem organischen Lösungsmittel durchgeführt wird. 3. Verfahren nach Patentanspruch, dadurch gekenn zeichnet, dass man die Verfahrensprodukte in Salze, insbesondere in .pharmazeutisch zulässige Säureadditions- salze, überführt.
CH343170A 1966-12-02 1967-12-01 Verfahren zur Herstellung von Estern CH504436A (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB54135/66A GB1147068A (en) 1966-12-02 1966-12-02 Phenyl-pyridine derivatives
CH1696967A CH492712A (de) 1966-12-02 1967-12-01 Verfahren zur Herstellung von Pyridinderivaten

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CH504436A true CH504436A (de) 1971-03-15

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CH343070A CH492714A (de) 1966-12-02 1967-12-01 Verfahren zur Herstellung von Pyridyl-alkancarbonsäuren

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