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)

Applications Claiming Priority (2)

Publications (1)

Family

ID=20331764

Family Applications (1)

Country Status (13)

Cited By (7)

• 1977
  • 1977-07-04 SE SE7707707A patent/SE409861B/sv unknown
• 1978
  • 1978-06-26 WO PCT/SE1978/000009 patent/WO1979000023A1/en unknown
  • 1978-06-26 CH CH329979A patent/CH641163A5/de not_active IP Right Cessation
  • 1978-06-27 CA CA306,260A patent/CA1082198A/en not_active Expired
  • 1978-06-29 DK DK782953A patent/DK295378A/da not_active Application Discontinuation
  • 1978-06-30 ES ES471302A patent/ES471302A1/es not_active Expired
  • 1978-06-30 FI FI782115A patent/FI64581C/fi not_active IP Right Cessation
  • 1978-06-30 IT IT50123/78A patent/IT1105226B/it active
  • 1978-07-03 NO NO782304A patent/NO782304L/no unknown
  • 1978-07-04 AT AT0483778A patent/AT365171B/de not_active IP Right Cessation
  • 1978-07-04 NL NL7807246A patent/NL7807246A/xx not_active Application Discontinuation
  • 1978-07-04 JP JP8182078A patent/JPS5414976A/ja active Pending
• 1979
  • 1979-08-03 SU SU792798502A patent/SU923366A3/ru active

Non-Patent Citations (1)

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