Chemistry:Imolamine

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Short description: Chemical compound
Imolamine
Skeletal formula
Space-filling model
Clinical data
Trade namesAngolon, Angoril, Circuline, Irri-Cor, Irrigor, Coremax
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC14H20N4O
Molar mass260.341 g·mol−1
3D model (JSmol)
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Imolamine (INN, BAN; brand names Angolon, Angoril, Circuline, Irri-Cor, Irrigor, Coremax) is a coronary vasodilator which is used in the treatment of angina pectoris and as a local anesthetic.[1][2]

Use patents:[3][4]

Synthesis

Butalamine has very similar synthesis but is alkylated on the alternate nitrogen position.

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Thieme Patent[5]

The reaction of benzoylchloride oxime [698-16-8] (2) with Cyanamide (3) gives 3-Phenyl-1,2,4-oxadiazol-5-amine [3663-37-4] (4). Alkylation with 2-chlorotriethylamine [100-35-6] (5) in the presence of KOH base occurs at the endocyclic ring nitrogen completing the synthesis of imolamine (6).

EFforts towards Onepot method (section 2.5 & 2.6).

References

  1. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 547–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA547. 
  2. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 680–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA680. 
  3. Anne Rolland, EP patent 0191253 (1986 to Laboratoires Albert Rolland SA).
  4. Anne Rolland, FR patent 2576789 (1986 to Laboratoires Albert Rolland SA).
  5. FR2023M idem J M D Aron-Samuel & J J Sterne, GB patent 1010231 (1965-11-17).