Uldazepam

Uldazepam
Clinical data
Other names	7-chloro-5-(2-chlorophenyl)-N-prop-2-enoxy-3H-1,4-benzodiazepin-2-amine
ATC code	none;
Identifiers
	IUPAC name (2Z)-7-Chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one O-allyloxime;
CAS Number	28546-58-9 ;
PubChem CID	34274;
ChemSpider	31577 ;
UNII	VAE9C0350C;
KEGG	D06263 ;
CompTox Dashboard (EPA)	DTXSID70182766 ;
Chemical and physical data
Formula	C18H15Cl2N3O
Molar mass	360.24 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc3ccccc3C/2=N/CC(=N/c1c\2cc(Cl)cc1)\NOC\C=C;
	InChI InChI=1S/C18H15Cl2N3O/c1-2-9-24-23-17-11-21-18(13-5-3-4-6-15(13)20)14-10-12(19)7-8-16(14)22-17/h2-8,10H,1,9,11H2,(H,22,23) ; Key:DTMPGSXFUXZBDK-UHFFFAOYSA-N ;
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Uldazepam is a drug which is a benzodiazepine derivative.^[1] It has sedative and anxiolytic effects similar to those of other benzodiazepines.^[2]^[3]

Synthesis

Thio thionamide is even more prone to amidine formation than the lactam itself.

Reaction of thionamide (2) with O-allyl-hydroxylamine gave the oximino (3) uldazepam.

^ "Uldazepam U 31920". Psychotropics. Retrieved 12 June 2013.
^ Oelschläger H, Ellaithy MM, Volke J (February 1988). "[Mechanism of the polarographic reduction of the tranquilizer uldazepam]". Archiv der Pharmazie (in German). 321 (2): 69–72. doi:10.1002/ardp.19883210205. PMID 3369929. S2CID 96356746.
^ Itil TM, Akpinar S, Ozkut H, Balki N, Herrmann WM (June 1974). "Clinical and computerized EEG effects of U-31,920, a new anxiolytic". Current Therapeutic Research, Clinical and Experimental. 16 (6): 642–54. PMID 4211146.
^ DE 2005176, Hester Jr., Jackson Boling, "3H-1,4-benzodiazepine und Verfahren zu deren Herstellung [3H-1,4-benzodiazepines and processes for their preparation]", published 1970-09-10, assigned to The Upjohn Co.