DE1445649A1 - Verfahren zur Herstellung neuer pharmazeutisch wirksamer Verbindungen - Google Patents

Verfahren zur Herstellung neuer pharmazeutisch wirksamer Verbindungen

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Publication number
DE1445649A1
DE1445649A1 DE19621445649 DE1445649A DE1445649A1 DE 1445649 A1 DE1445649 A1 DE 1445649A1 DE 19621445649 DE19621445649 DE 19621445649 DE 1445649 A DE1445649 A DE 1445649A DE 1445649 A1 DE1445649 A1 DE 1445649A1
Authority
DE
Germany
Prior art keywords
general formula
compound
alk
preparation
group
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
DE19621445649
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English (en)
Other versions
DE1445649C (de
Inventor
Helmut Beschke
Schuler Dr Wilhelm
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
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
Application filed by Degussa GmbH filed Critical Degussa GmbH
Publication of DE1445649A1 publication Critical patent/DE1445649A1/de
Application granted granted Critical
Publication of DE1445649C publication Critical patent/DE1445649C/de
Expired legal-status Critical Current

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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
    • C07D213/60—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
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D213/70—Sulfur 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
    • C07D213/60—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
    • 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
    • C07D213/81—Amides; Imides
    • 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

Landscapes

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

Description

DEUTSCHE GOLD- UND SIIiBER-SCHBIDEAHSiALT VORMALS ROESSLER Frankfurt am Hain·» Weissfrauenstrasae 9 14456 Verfahren zur Herstellung neuer pharmazeutisch wirksamer Verbindungen
Die Erfindung betrifft ein Verfahren zur Herstellung neuer Pyridinderivate der allgemeinen Formel
X - Alk
ihrer Salze und quartären Ammoniumyerbindungeno
In dieser formel bedeuten R1 und Rg Alkylreote, vorzugsweia® solche, die zu einem Ring geschlossen sind, der ein weiteres H eteroatom, insbesondere Sauerstoff, enthalten kann« Alk bedeutet eine gerade oder verzweigte niedere Alkylenkette mit höchstens 4 C-Atomeng X bedeutet Schwefel, Sauerstoff oder die NH-Gruppe* Y kann ein Halogen, vorzugsweise in 3-f?tellung, aber auoh eine Trihalogenmethyl», ZoB» eine Trifluormethyl-, Alkyl-, vorzugsweise Methyl-, oder Alkoxy», vorsugeweiae lletiioxygruppe, bedeuten
Die beanspruchten Verbindungen haben gute pharmakologische Eigenschaften, inebesonderen analgetische baw, antiphlogi-8tische Wirkungen«
Die beanspruchten Verbindungen können erhalten werden durch Umsetzung eines Pyridinderivates der allgemeinen Formel
- Hal mi% einer Verbindung der allgemeinen Formel
HX - Alk - H^ 1 R2
9098057097^
~2~ 144564S
wobei Hal Chlor oder Brom bedeutete BIe Umsetzung erfolgt vorzugsweise bei erhöhter Temperatur und unter Verwendung von basischen Kondensat! onsraitteln-, wie Pottasohe, Natriumäthylat oder anderer basischer Stoffe« ZoBo tertiärer Amine«
Man kann auch ein Pyridinderivat der allgemeinen Formel
I- XH
mit einer Verbindung der allgemeinen Formel
Hai - Alk -
kondensieren8 vorzugsweise in Gegenwart baalscher Stoffe, wie Natrlummethylat oder Natrlumamid, bei erhöhter Temperatur ο
Sohl ie s si i oh können die erfindungsgemässen Verbindungen auch durch Umsetzung einer Verbindung der allgemeinen formel
X - Alk - Hai mit einem sekundären Amin der allgemeinen Formel
gewonnen werden, vorzugsweise in einem inerten Lösungsmittel unter Verwendung basischer Kondensationsmittel, zoB. Pottasche»
Die so erhaltenen Basen können in an sich bekannter Weis*
in ihre Salze oder quartären Ammoniumverbindungen übergeführt werdeno
144564S
Beispiel It
32 feile Morpholinoathylmereaptan, in 300 !eilen Xylol gelöst, werden unter Sieden an Rückfluss ait 20 Seilen einer SO 5&igen Suspension τοη latriumamid in Toluol versetzt« Nach beendeter Gasentwicklung «erden 33 Teile 2f3*-Sichlorpyridinf in 200 Seilen Xylol gelSst» zugetropft und das Gemisch 1 Stunde an Rückfluss gekocht, 5ach de» Abkühlen wird der Ansatz alt Wasser sersetzt, die Xylolsohicht mit verdünnter Salzsäure bei einen pH-Wert τοη 4 extrahiert und hierauf die saure wässrige Phase «it natronlauge und Äther aufgearbeitete Der Ätierextrakt wird getrocknet und im Vakuum destillierte Bei 0,5 m Brück und 164 bis 168° 0 gehen 32 g 2~(MorpholinoäthyliB8rcapto)-3~ohlorpyridin über. Sas salBsaure Salz« aus Xsopropanol gefallt und uekriatallisiert, schallst bei 131° 6c
Beispiel 2*
75 Seil· 2-Oxy-6-chlor-=pyridin9 in 750 Teilen Toluol gelöst, werden nit 43 Teilen einer 50 fSigen Suspension von Satriueamid in Toluol unter Sieden aa Eüokflua? versetzto Anscblieesend tropft »an 70 Teile Dimethylaminoäthylchlorid sni und kocht noch 3 Stunden weitere Haoh Aufarbeitung entsprechend Beispiel 1 werden bei Ep11I 115 bis 122° C 53 Seile 2-{Meett»yle»inc£thory)«6-chlorpyridin erhalten« Das Hydrochlorid schBilet bei 146 bis 148° 0«,
Beispiel 3»
Entsprechend Beispiel 2, aber unter Verwendung τοη Blaethylaminopropylchlorid, wird 2-(Diaetliylaainopropyloxy»)*6-' chlorpyridin το» Kp10 ! 134 bis 13β° C erhalten» Bas Hydrocblorid schmilzt bei 181 bis 183° C0
4 -
909805/0972
144564S
Beispiel 4s
74 Seile 2f6-Bichlorpyridizi und 102 iDeile !^Dimethylamine« propylamin-3- werden auf dem ölbad vorsichtig erhitzt· Bei etwa 90° C setzt eine heftige Reaktion einte !fach dem Abkühlen wird in einem Gemisch von Wasser und. Äther gelöst9 mit Pottasche alkalisch gemacht und die; Itherlösung aufgearbeitete Bei Ep11? 176 bis 182° 0 werden 58 g 2«(Dimethylaminopropyl~ amino)=»6=chlorpyridin erhalten0 Das Hydroohlorid schmilzt bei 83 bis 85° C0
909805/0972

Claims (1)

  1. ~5 ~ 144564S
    Patentanspruchs
    Verfahren zur Herstellung von Verbindungen der allgemeinen Formel
    wobei H1 und R2 Alkylreate, Ste vorzugsweise zu einen Hing ge achlos sen sind, der durch ein Heteroatom, insbesondere duroh Sauerstoff» unterbrochen sein kann, Alk eine gerade oder verareigte Alkylengruppe alt höchstens 4 C-Atomen, X vorzugsweise Schwefel, aber auch Sauerstoff oder die $H~£ruppe, und 7 Halogen, vorzugsweise in 3-Stellung, aber auch eine Alkyl-, Trihalogenmethyl- oder Alkorygruppe bedeuten, dadurch gekennaeiohnetf dass man
    a) eine Verbindung der allgemeinen Formel
    }- Hai
    mit einer Verbindung der allgemeinen Formel
    HX- Alk - H<
    uiieetst oder
    b) eine Verbindung der allgemeinen formel
    - XH
    ■it einer Verbindung der allgeneinen Formel
    - 6
    EaI - Alk
    umsetzt oder c) eine Verbindung der allgemeinen Formel
    144564J9
    ■Η,
    r J= X - Alk - Hai nit einem sekundären Amin der allgemeinen Formel
    umsetzt
    und d Ie erhaltenen Basen gegebenenfalls in ibre Salze oder quartären Verbindungen überführt»
    "■ ·-> ο Q Π ~ OQT/
DE19621445649 1962-03-27 1962-03-27 Pyridinderivate und Verfahren zu ihrer Herstellung Expired DE1445649C (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DED0038499 1962-03-27
DED0038499 1962-03-27

Publications (2)

Publication Number Publication Date
DE1445649A1 true DE1445649A1 (de) 1969-01-30
DE1445649C DE1445649C (de) 1973-06-07

Family

ID=

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0065757A1 (de) * 1981-05-26 1982-12-01 Merck & Co. Inc. 1-(3-Halogen-2-pyridinyl)piperazine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
US4474781A (en) * 1979-04-02 1984-10-02 Merck & Co., Inc. Treating hypertension with aminoalkoxypyridines
DE3443968A1 (de) * 1983-12-28 1985-10-31 Degussa Ag, 6000 Frankfurt Neue pyridin-2-ether beziehungsweise pyridin-2-thioether mit einem stickstoffhaltigen cycloaliphatischen ring

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4474781A (en) * 1979-04-02 1984-10-02 Merck & Co., Inc. Treating hypertension with aminoalkoxypyridines
EP0065757A1 (de) * 1981-05-26 1982-12-01 Merck & Co. Inc. 1-(3-Halogen-2-pyridinyl)piperazine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE3443968A1 (de) * 1983-12-28 1985-10-31 Degussa Ag, 6000 Frankfurt Neue pyridin-2-ether beziehungsweise pyridin-2-thioether mit einem stickstoffhaltigen cycloaliphatischen ring

Also Published As

Publication number Publication date
FR1451191A (fr) 1966-01-07
US3370059A (en) 1968-02-20
GB1041342A (en) 1966-09-07

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Legal Events

Date Code Title Description
C3 Grant after two publication steps (3rd publication)
E77 Valid patent as to the heymanns-index 1977