GB834336A - (4-biphenylyl-pyridyl)-carbinols - Google Patents

(4-biphenylyl-pyridyl)-carbinols

Info

Publication number
GB834336A
GB834336A GB2543057A GB2543057A GB834336A GB 834336 A GB834336 A GB 834336A GB 2543057 A GB2543057 A GB 2543057A GB 2543057 A GB2543057 A GB 2543057A GB 834336 A GB834336 A GB 834336A
Authority
GB
United Kingdom
Prior art keywords
bromide
phenyl
acid
pyridyl
biphenylyl
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
GB2543057A
Inventor
Guido Cavallini
Elena Massarani
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.)
Francesco Vismara SpA
Original Assignee
Francesco Vismara SpA
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 Francesco Vismara SpA filed Critical Francesco Vismara SpA
Priority to GB2543057A priority Critical patent/GB834336A/en
Publication of GB834336A publication Critical patent/GB834336A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms

Abstract

The invention comprises (4-biphenyl-pyridyl)-a -substituted carbinols of formula <FORM:0834336/IV (b)/1> in which X is a phenyl, substituted phenyl, alkyl, aralkyl or cycloalkyl radical. They may be prepared by reacting a 4-biphenylyl-pyridyl ketone with a Grignard reagent of the formula X-Mg-Y, in which Y is a halogen atom, in an organic solvent at elevated temperature and subjecting the resulting mixture to mild hydrolysis. The 4-biphenylyl-pyridyl ketones used as starting materials may be prepared by condensing isonicotinic acid chloride or nicotinic acid chloride, preferably in the presence of a condensing agent such as aluminium chloride, with diphenyl and hydrolysing the product. The condensation step is conveniently carried out in an organic solvent, e.g. carbon disulphide, at a temperature between 40 DEG and 150 DEG C. The ketones are converted as above to the carbinols using a Grignard reagent. Suitable halides for use in the Grignard reaction are, for example, phenyl bromide, m- and p-methyl phenyl bromide, p-methoxyphenyl bromide, o-, m- and p-chlorphenyl bromide, o-, m- and p-fluorophenyl bromide, dichlorophenyl bromide and lower alkyl and cycloalkyl bromides and iodides. Suitable solvents for the Grignard reaction are diethyl ether, tetrahydrofuran, benzene, toluene, xylene and anisole and the reaction is conveniently carried out at the boiling-point of the solvent, preferably between 30 DEG and 150 DEG C. The mild hydrolysis of the product may be carried out by an ammonium salt or by dilute acetic acid followed by dilute alkali. The compound may be isolated as the free base or as a crystalline salt by treating the free base with an acid such as hydrochloric acid. The products may be used in pharmacological compositions (see Group VI).ALSO:Pharmacological compositions comprise a drug active on the central nervous system as a stimulant or depressant, for example barbiturates, such as 5-(1-methylbutyl)-51-ethyl barbituric acid, 1.5 - dimethyl - 51 - cyclohexenyl barbituric acid and 2 - thio - 5 - ethyl-51 - (1 - methylbutyl) - barbituric acid, and a compound of general formula <FORM:0834336/VI/1> in which X is a phenyl, substituted phenyl, alkyl, aralkyl or cycloalkyl radical, used in an amount sufficient to potentiate the action of the drug.
GB2543057A 1957-08-12 1957-08-12 (4-biphenylyl-pyridyl)-carbinols Expired GB834336A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2543057A GB834336A (en) 1957-08-12 1957-08-12 (4-biphenylyl-pyridyl)-carbinols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2543057A GB834336A (en) 1957-08-12 1957-08-12 (4-biphenylyl-pyridyl)-carbinols

Publications (1)

Publication Number Publication Date
GB834336A true GB834336A (en) 1960-05-04

Family

ID=10227540

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2543057A Expired GB834336A (en) 1957-08-12 1957-08-12 (4-biphenylyl-pyridyl)-carbinols

Country Status (1)

Country Link
GB (1) GB834336A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106535635A (en) * 2014-04-15 2017-03-22 美国陶氏益农公司 Metalloenzyme inhibitor compounds as fungicides

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106535635A (en) * 2014-04-15 2017-03-22 美国陶氏益农公司 Metalloenzyme inhibitor compounds as fungicides
JP2017517493A (en) * 2014-04-15 2017-06-29 ダウ アグロサイエンシィズ エルエルシー Metalloenzyme inhibitor compounds as fungicides
EP3131400A4 (en) * 2014-04-15 2017-11-29 Dow AgroSciences LLC Metalloenzyme inhibitor compounds as fungicides
US9957252B2 (en) 2014-04-15 2018-05-01 Dow Agrosciences Llc Metalloenzyme inhibitor compounds as fungicides

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