Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Oxatomide: Difference between pages

{{Short description|Chemical compound}}

| verifiedrevid = 462266871

| width = 250px

| tradename = Tinset, others

| pregnancy_category =

| routes_of_administration = [[Oral administration|By mouth]]

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 60607-34-3

| ChEBI = 31943

| UNII_Ref = {{fdacite|correct|FDA}}

| synonyms = KW-4354; McN-JR 35443; R-35443

| SMILES = O=C2Nc1ccccc1N2CCCN5CCN(C(c3ccccc3)c4ccccc4)CC5

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'''Oxatomide''', sold under the brand name '''Tinset''' among others, is a [[antihistamine]] of the [[diphenylmethylpiperazine]] family which is marketed in [[Europe]], [[Japan]], and a number of other countries.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA912|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=912–}}</ref><ref name="pmid6138301">{{cite journal | vauthors = Ohmori K, Ishii H, Nito M, Shuto K, Nakamizo N | title = [Pharmacological studies on oxatomide (KW-4354). (7) Antagonistic effects on chemical mediators] | language = ja | journal = Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica | volume = 81 | issue = 5 | pages = 399–409 | date = May 1983 | pmid = 6138301 | doi = 10.1254/fpj.81.399 | doi-access = free }}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA768|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=768–}}</ref><ref name="Drugs.com">{{Cite web | url=https://www.drugs.com/international/oxatomide.html |title = Oxatomide | work = Drugs.com }}</ref> It was discovered at [[Janssen Pharmaceutica]] in 1975.<ref name="Schwartz1989">{{cite book| vauthors = Schwartz H |title=Breakthrough: the discovery of modern medicines at Janssen|url=https://archive.org/details/breakthroughdisc0000schw|url-access=registration|date=August 1989|publisher=Skyline Pub. Group|isbn=978-1-56019-100-1|page=[https://archive.org/details/breakthroughdisc0000schw/page/149 149]}}</ref> Oxatomide lacks any [[anticholinergic]] effects.<ref name="pmid6138301"/> In addition to its [[H1 receptor|H₁ receptor]] [[receptor antagonist|antagonism]], it also possesses [[antiserotonergic]] activity similarly to [[hydroxyzine]].<ref name="pmid6138301"/>

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It was patented in 1976 and came into medical use in 1981.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=548 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA548 |language=en}}</ref>

==Chemistry==

===Synthesis===

[[File:Oxatomide synthesis.svg|thumb|center|500px|Oxatomide synthesis:<ref>{{Cite patent|country=DE|number=2714437|pubdate=1977-10-20|title=Piperazin- und Piperidinderivate, Verfahren zu ihrer Herstellung und Arzneipräparate [Piperazine and piperide derivatives, procedures for their manufacturing and medicinal preparations]|assign=[[Janssen Pharmaceutica]] | inventor = Vandenberk J, Kennis LE, Van der Aa MJ, Van Heertum AH}}</ref><ref>{{cite patent | country = US | number = 4250176 | inventor = Vandenberk J, Kennis LE, Van der Aa MJ, Van Heertum AH | assign1 = Janssen Pharmaceutica NV | url = https://patents.google.com/patent/US4250176 | postscript = . | gdate = 10 February 1981 }}</ref>]]

Reaction of [[:de:Benzimidazolon|2-Benzimidazolinone]] with [[isopropenyl acetate]] leads to the singly protected imidazolone derivative ('''2'''). [[Alkylation]] of this with [[3-chloro-1-bromopropane]] affords the functionalized derivative ('''3'''). Alkylation of the [[Benzhydryl compounds|monobenzhydryl]] derivative of [[piperazine]] ('''4''') with '''3''' gives oxatomide ('''5'''), after hydrolytic removal of the [[protecting group]].

== References ==

{{Reflist|2}}

{{Antihistamines}}

{{Navboxes

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{{Histamine receptor modulators}}

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[[Category:Benzimidazoles]]

[[Category:Belgian inventions]]

[[Category:H1 receptor antagonists]]

[[Category:Janssen Pharmaceutica]]

[[Category:Gamma-lactams]]

[[Category:Cyclizines]]

[[Category:Ureas]]

{{Respiratory-system-drug-stub}}