GB839943A - Substituted toluidides and compositions containing them - Google Patents

Substituted toluidides and compositions containing them

Info

Publication number
GB839943A
GB839943A GB18127/58A GB1812758A GB839943A GB 839943 A GB839943 A GB 839943A GB 18127/58 A GB18127/58 A GB 18127/58A GB 1812758 A GB1812758 A GB 1812758A GB 839943 A GB839943 A GB 839943A
Authority
GB
United Kingdom
Prior art keywords
alpha
heated
yield
toluidine
iso
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB18127/58A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AstraZeneca AB
Original Assignee
Astra AB
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Astra AB filed Critical Astra AB
Publication of GB839943A publication Critical patent/GB839943A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

Abstract

The invention comprises o-toluidides of the general formula <FORM:0839943/IV (b)/1> (wherein R is an alkyl group of 2 to 4 carbon atoms) and their pharmaceutically useful acidaddition salts. In examples: (1) o-toluidine and alpha-bromopropionyl bromide in glacial acetic acid give alpha-bromopropio-o-toluidide and this with monoethylamine in benzene gives an o-toluidide of the above formula wherein R is ethyl; (2) a water-soluble organic solvent replaces the acetic acid of (1); (3) to (6) the corresponding compounds wherein R is n- and iso-propyl and n-, iso- and sec.-butyl are prepared as in (1); (7) o-tolylphosphazo-o-toluidide and alpha-(n-propylamino)-propionic acid hydrochloride are heated together to yield the compound wherein R is n-propyl; (8) o-toluidine and alpha-(iso-propylamino)-propionic acid hydrochloride are heated with P2O5 to yield the compound wherein R is iso-propyl; (9) sodium alpha - (N - carbobenzoxy - iso - propylamino)-propionic acid and o-toluidine are heated in benzene containing benzoyl chloride and triethylamine and the product is hydrogenated in the presence of palladium to yield the product of (8); (10) alpha-(p-toluenesulphonyloxy)-propionyl chloride and o-toluidine are heated in benzene to give alpha - (p - toluenesulphonyloxy) - propio - o - toluidide and this is heated with monoethylamine in benzene to yield the product of (1); (11) ethyl alpha - (n - propyl-amino)-propionate and o-toluidine are heated in benzene containing sodamide to yield the product of (7); and (12) alpha - (n - butylamino)-propionic acid and o-tolylisocyanate are heated in pyridine, the pyridine is removed and the residue is heated with hydrochloric acid to yield the compound wherein R is n-butyl. Some of the products are isolated as their hydrochlorides. Specification 634,072 is referred to.ALSO:Pharmaceutical compositions comprise a local anaesthetic compound of the general formula <FORM:0839943/VI/1> (wherein R is an alkyl group of 2 to 4 carbon atoms) or an acid-addition salt thereof in admixture with an inert diluent or diluents. Specification 634,072 is referred to.
GB18127/58A 1957-06-26 1958-06-06 Substituted toluidides and compositions containing them Expired GB839943A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE839943X 1957-06-26

Publications (1)

Publication Number Publication Date
GB839943A true GB839943A (en) 1960-06-29

Family

ID=20354182

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18127/58A Expired GB839943A (en) 1957-06-26 1958-06-06 Substituted toluidides and compositions containing them

Country Status (1)

Country Link
GB (1) GB839943A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4891058A (en) * 1988-07-18 1990-01-02 Ici Americas Inc. 1-alkyl-3-aryl imidazolidine-2,4-diones and herbicidal use
JP2011513226A (en) * 2008-02-21 2011-04-28 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Amine compounds and ether compounds that modulate the CB2 receptor
CN102093248A (en) * 2010-12-22 2011-06-15 蚌埠丰原医药科技发展有限公司 Method for preparing N-(2-Methylphenyl)-2-(propylamino)propa-namide
CN104529812A (en) * 2014-12-31 2015-04-22 济南诚汇双达化工有限公司 Method for preparing propitocaine hydrochloride
CN105439887A (en) * 2015-12-25 2016-03-30 重庆康乐制药有限公司 Preparation method of prilocaine base

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4891058A (en) * 1988-07-18 1990-01-02 Ici Americas Inc. 1-alkyl-3-aryl imidazolidine-2,4-diones and herbicidal use
JP2011513226A (en) * 2008-02-21 2011-04-28 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Amine compounds and ether compounds that modulate the CB2 receptor
US8957063B2 (en) 2008-02-21 2015-02-17 Boehringer Ingelheim International Gmbh Amine and ether compounds which modulate the CB2 receptor
CN102093248A (en) * 2010-12-22 2011-06-15 蚌埠丰原医药科技发展有限公司 Method for preparing N-(2-Methylphenyl)-2-(propylamino)propa-namide
CN102093248B (en) * 2010-12-22 2013-12-04 蚌埠丰原医药科技发展有限公司 Method for preparing N-(2-Methylphenyl)-2-(propylamino)propa-namide
CN104529812A (en) * 2014-12-31 2015-04-22 济南诚汇双达化工有限公司 Method for preparing propitocaine hydrochloride
CN105439887A (en) * 2015-12-25 2016-03-30 重庆康乐制药有限公司 Preparation method of prilocaine base

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