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WO1979000023A1 - Nouveau procede de preparation d'un compose therapeutique a base de pyridine - Google Patents

Nouveau procede de preparation d'un compose therapeutique a base de pyridine Download PDF

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Publication number
WO1979000023A1
WO1979000023A1 PCT/SE1978/000009 SE7800009W WO7900023A1 WO 1979000023 A1 WO1979000023 A1 WO 1979000023A1 SE 7800009 W SE7800009 W SE 7800009W WO 7900023 A1 WO7900023 A1 WO 7900023A1
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
therapeutically active
compound
formula
novel process
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.)
Ceased
Application number
PCT/SE1978/000009
Other languages
English (en)
Inventor
P Bamberg
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.)
Astra Lakemedel AB
Original Assignee
Astra Lakemedel AB
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 Astra Lakemedel AB filed Critical Astra Lakemedel AB
Publication of WO1979000023A1 publication Critical patent/WO1979000023A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom

Definitions

  • the present invention is related to a novel process for pre- paration of a therapeutically active compound.
  • An object of the invention is to provide a process enabling improved economy of production and avoiding use of chemicals that are difficult to handle.
  • Swedish Patent 361 663 discloses i . a . a compound of the formu la
  • the main disadvantages of the known method is that the pre ⁇ paration of the intermediate is complicated, involving chemicals which are difficult to handle, such as butyl lithi and that only a low overall yield may be obtained.
  • Ph denotes phenyl and R denotes CH- or H, and reacted with 4-bromophenyl-3-pyridylketcne in the presence of sodium methylate according to the following scheme:
  • the last reaction is suitably carried out in a solvent such as dimethylforma ide, hexamethylphosphorus-triamide or di- methylsulfoxide.
  • a solvent such as dimethylforma ide, hexamethylphosphorus-triamide or di- methylsulfoxide.
  • the new manner of preparing the Wittig re agent has surprisingly been found to be operable and is technically advantageous.
  • a further advantage of the new process is that the simple reactant sodium methylate may be used as a base instead of butyl ' -lithium often used in simil reactions.
  • Butyl lithium is, as mentioned, difficult to handle and should if possible be avoided in production on a technical scale because of its strong reactivity, which i.a may lead to self-ignition.
  • the therapeutically active end compound VI exists in two stereoisomeric forms, a Z-form and an E-form according to t IUPAC nomenclature.
  • the preferred isomer is the Z-isomer, having the configuration
  • the preferred isomer may be obtained by isolation from an isom ⁇ ric mixture of the end compound VI..
  • a modified manner of preparing the end compound is along t reaction route:.
  • R represents methyl or hydrogen
  • X is a leaving group selected from the halogens suc as Cl or Br methylsulfonyl and toluenesulfonyl, introduced reacting the compound of formula IV with a halogenating age such as HC1, HBr, PBr 3 , PClg, S0C1 , PCI or methylsulfonic toluenesulfonic acids and wherein R is as defined above.
  • the compound and the methods of the invention are useful in the pharmaceutical industry, especially in preparation of a compound of formula VI above in a technical scale.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Procede de preparation de composes a base de pyridine a action therapeutique comprenant la preparation d'un reactif de Wittig et son emploi dans une reaction du type suivant:
PCT/SE1978/000009 1977-07-04 1978-06-26 Nouveau procede de preparation d'un compose therapeutique a base de pyridine Ceased WO1979000023A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE7707707A SE409861B (sv) 1977-07-04 1977-07-04 Ett nytt forfarande for framstellning av en terapeutisk aktiv pyridinforening
SE7707707 1977-07-04

Publications (1)

Publication Number Publication Date
WO1979000023A1 true WO1979000023A1 (fr) 1979-01-25

Family

ID=20331764

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SE1978/000009 Ceased WO1979000023A1 (fr) 1977-07-04 1978-06-26 Nouveau procede de preparation d'un compose therapeutique a base de pyridine

Country Status (13)

Country Link
JP (1) JPS5414976A (fr)
AT (1) AT365171B (fr)
CA (1) CA1082198A (fr)
CH (1) CH641163A5 (fr)
DK (1) DK295378A (fr)
ES (1) ES471302A1 (fr)
FI (1) FI64581C (fr)
IT (1) IT1105226B (fr)
NL (1) NL7807246A (fr)
NO (1) NO782304L (fr)
SE (1) SE409861B (fr)
SU (1) SU923366A3 (fr)
WO (1) WO1979000023A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0081478A3 (en) * 1979-11-16 1984-01-04 Astra Lakemedel Aktiebolag Novel halophenyl-pyridyl-allylamine derivatives, processes and intermediates as well as pharmaceutical preparations thereof
US20120217101A1 (en) * 2009-10-23 2012-08-30 Kone Corporation Elevator arrangement and method
US20120291395A1 (en) * 2009-12-31 2012-11-22 Kone Corporation Method in the manufacture of an elevator
US20130118838A1 (en) * 2010-05-28 2013-05-16 Kone Corporation Method and elevator arrangement
US20130233655A1 (en) * 2012-03-06 2013-09-12 Kone Corporation Method and an elevator arrangement
US20130248299A1 (en) * 2010-12-01 2013-09-26 Kone Corporation Elevator arrangement and method
US9388020B2 (en) * 2012-03-06 2016-07-12 Kone Corporation Method and an elevator arrangement

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
ORGANIC REACTIONS 1965 (Wiley & Sons, New York) vol 14, p. 319-321, 334, 388-398 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0081478A3 (en) * 1979-11-16 1984-01-04 Astra Lakemedel Aktiebolag Novel halophenyl-pyridyl-allylamine derivatives, processes and intermediates as well as pharmaceutical preparations thereof
US20120217101A1 (en) * 2009-10-23 2012-08-30 Kone Corporation Elevator arrangement and method
US20120291395A1 (en) * 2009-12-31 2012-11-22 Kone Corporation Method in the manufacture of an elevator
US20130118838A1 (en) * 2010-05-28 2013-05-16 Kone Corporation Method and elevator arrangement
US20130248299A1 (en) * 2010-12-01 2013-09-26 Kone Corporation Elevator arrangement and method
US20130233655A1 (en) * 2012-03-06 2013-09-12 Kone Corporation Method and an elevator arrangement
US9388020B2 (en) * 2012-03-06 2016-07-12 Kone Corporation Method and an elevator arrangement

Also Published As

Publication number Publication date
ATA483778A (de) 1981-05-15
SE7707707L (sv) 1979-01-05
SU923366A3 (ru) 1982-04-23
NL7807246A (nl) 1979-01-08
FI64581B (fi) 1983-08-31
JPS5414976A (en) 1979-02-03
IT1105226B (it) 1985-10-28
NO782304L (no) 1979-01-05
CA1082198A (fr) 1980-07-22
ES471302A1 (es) 1979-09-01
SE409861B (sv) 1979-09-10
IT7850123A0 (it) 1978-06-30
FI64581C (fi) 1983-12-12
AT365171B (de) 1981-12-28
DK295378A (da) 1979-01-05
FI782115A7 (fi) 1979-01-05
CH641163A5 (de) 1984-02-15

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