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  N 15823-89-9 (HCl)
PubChem CID	27501
DrugBank	DB09284  Y
ChemSpider	10669810  N
UNII	K5F4RU5VQJ
KEGG	D07159  Y
ChEMBL	ChEMBL2104282  N
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 N Key:MGSPDRWOUCPKNZ-UHFFFAOYSA-N N
NY  (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]}

Use patents: ^{[3] [4]}

Synthesis

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

Thieme Patent

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.
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).