Imolamine
Chemical compound
- C01DX09 (WHO)
- Diethyl[2-(5-imino-3-phenyl-4,5-dihydro-1,2,4-oxadiazol-4-yl)ethyl]amine
- 318-23-0
N
15823-89-9 (HCl)
- 27501
- DB09284
Y
- 10669810 N
- K5F4RU5VQJ
- D07159 Y
- ChEMBL2104282 N
- DTXSID00861870
- Interactive image
- CCN(CC)CCN2C(=N)O\N=C2\c1ccccc1
InChI
- InChI=1S/C14H20N4O/c1-3-17(4-2)10-11-18-13(16-19-14(18)15)12-8-6-5-7-9-12/h5-9,15H,3-4,10-11H2,1-2H3N
- Key:MGSPDRWOUCPKNZ-UHFFFAOYSA-NN
N
Y (what is this?) (verify)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]
Synthesis
Butalamine has very similar synthesis but is alkylated on the alternate nitrogen position.
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
- ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 547–. ISBN 978-3-88763-075-1.
- ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 680–. ISBN 978-1-4757-2085-3.
- ^ Anne Rolland, EP 0191253 (1986 to Laboratoires Albert Rolland SA).
- ^ Anne Rolland, FR 2576789 (1986 to Laboratoires Albert Rolland SA).
- ^ FR2023M idem J M D Aron-Samuel & J J Sterne, GB 1010231 (1965-11-17).
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- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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