Zomebazam
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 451222461
| IUPAC_name = 1,3,8-trimethyl-4-phenylpyrazolo[3,4-b][1,4]diazepine-5,7-dione
| image = Zomebazam structure.svg
| width = 155
| tradename =
| legal_status =
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 78466-70-3
| ATC_prefix =
| PubChem = 132677
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = G563Y6G60K
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 117132
| smiles = O=C1N(c2c(N(C(=O)C1)C)n(nc2C)C)c3ccccc3
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C15H16N4O2/c1-10-14-15(18(3)16-10)17(2)12(20)9-13(21)19(14)11-7-5-4-6-8-11/h4-8H,9H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = BFWACMHTIVUWJS-UHFFFAOYSA-N
| C=15 | H=16 | N=4 | O=2
}}
Zomebazam{{cite patent | country = US | number = 3558605 | title = 4-Aryl-5,6,7,8-tetrahydropyrazolo(3,4-B)-(1,5)diazepine-1H,4H-5,7-diones and medicaments containing same }} produced by Hoechst is a pyrazolodiazepinone derivative drug with anxiolytic properties. It is structurally related to razobazam and zometapine.{{Cite web | url = http://www.psychotropics.dk/moleculeView/default.aspx?ID=1480&Catalogtype=A&ChapterID=237&Thissortorder=2 | title = Zomebazam | access-date = 7 December 2009 | year = 2003 | publisher = psychotropics.dk }}
Synthesis
The catalytic hydrogenation of N,2,5-trimethyl-4-phenyldiazenylpyrazol-3-amine{{efn|[https://pubchem.ncbi.nlm.nih.gov/compound/136203602 CID:136203602]}} (1) over Raney nickel gives 4-amino-1,3-dimethyl-5-methylaminopyrazole{{efn| [https://pubchem.ncbi.nlm.nih.gov/compound/10219477 CID:10219477]}} (2). Treatment with methyl malonyl chloride{{efn|CAS# [37517-81-0] }} (3) gives 4-α-ethoxycarbonylacetylamino-1,3-dimethyl-5-methylaminopyrazole{{efn|[https://pubchem.ncbi.nlm.nih.gov/compound/20561101 CID:20561101]}} (4). Base-catalyzed lactamization gives (5). The Goldberg reaction completes the synthesis of zomebazam (6).{{cite journal | vauthors = Renger B | title = Direkte N-Arylierung von Amiden: Eine Verbesserung der Goldberg-Reaktion. | journal = Synthesis | date = 1985 | volume = 1985 | issue = 9 | pages = 856–560 | doi = 10.1055/s-1985-31364
| s2cid = 93397774 }}{{cite patent | country = US | number = 4302468 | inventor = Rackur G, Hoffmann I | gdate = 1981 | assign1 = Hoechst Aktiengesellschaft }}
See also
References
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Notes
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{{Benzodiazepines}}
{{GABAAR PAMs}}