Imolamine

Imolamine
Clinical data
Trade names	Angolon, Angoril, Circuline, Irri-Cor, Irrigor, Coremax
ATC code	C01DX09 (WHO) ;
Identifiers
	IUPAC name Diethyl[2-(5-imino-3-phenyl-4,5-dihydro-1,2,4-oxadiazol-4-yl)ethyl]amine;
CAS Number	318-23-0 ; 15823-89-9 (HCl);
PubChem CID	27501;
DrugBank	DB09284 ;
ChemSpider	10669810 ;
UNII	K5F4RU5VQJ;
KEGG	D07159 ;
ChEMBL	ChEMBL2104282 ;
CompTox Dashboard (EPA)	DTXSID00861870 ;
ECHA InfoCard	100.005.699
Chemical and physical data
Formula	C14H20N4O
Molar mass	260.341 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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,3-4,10-11H2,1-2H3 ; Key:MGSPDRWOUCPKNZ-UHFFFAOYSA-N ;
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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.

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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[1] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 547–. ISBN 978-3-88763-075-1.

[Elks2014-2] 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.

[3] Anne Rolland, EP 0191253 (1986 to Laboratoires Albert Rolland SA).

[4] Anne Rolland, FR 2576789 (1986 to Laboratoires Albert Rolland SA).

[5] FR2023M idem J M D Aron-Samuel & J J Sterne, GB 1010231 (1965-11-17).

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v t e Vasodilators used in cardiac diseases (C01D)
Nitrovasodilators	Nitroglycerin # Isosorbide dinitrate # Isosorbide mononitrate Itramin tosilate Linsidomine Molsidomine Nicorandil Pentaerythritol tetranitrate Propatylnitrate Tenitramine Trolnitrate
Quinolone vasodilators	Flosequinan^‡
Others	Benziodarone Carbocromen Cinepazet Cloridarol Dilazep Efloxate Etafenone Gapicomine Heptaminol Hexobendine Imolamine Levosimendan Nesiritide Nicorandil Oxyfedrine Pimobendan Prenylamine Serelaxin Trapidil Vericiguat
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III