ES258418A1 - Improvements in and relating to n-heterocyclic compounds - Google Patents

Improvements in and relating to n-heterocyclic compounds

Info

Publication number
ES258418A1
ES258418A1 ES0258418A ES258418A ES258418A1 ES 258418 A1 ES258418 A1 ES 258418A1 ES 0258418 A ES0258418 A ES 0258418A ES 258418 A ES258418 A ES 258418A ES 258418 A1 ES258418 A1 ES 258418A1
Authority
ES
Spain
Prior art keywords
general formula
compounds
reacting
group
acid
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
ES0258418A
Other languages
Spanish (es)
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.)
Novartis AG
Original Assignee
JR Geigy AG
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
Priority claimed from CH98160A external-priority patent/CH381692A/en
Priority claimed from CH97960A external-priority patent/CH378893A/en
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of ES258418A1 publication Critical patent/ES258418A1/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated

Abstract

The invention comprises iminodibenzyl (10,11-dihydro-5H-dibenzo [b.f.] azepine) derivatives of the general formula <FORM:0926816/IV(a)/1> (wherein R represents a hydrogen atom, a C1-4 alkyl radical or an aralkyl radical, X represents an alkylene radical having 2-6 carbon atoms in a straight or branched chain, and Am represents a C1-4 alkylamino group, or a C2-8 dialkylamino group in which one alkyl radical may be bound direct to X or both alkyl radicals may be bound together direct or through an oxygen atom or an alkylimino, hydroxyalkylimino or alkanoyloxyalkylimino group, each alkyl or alkanoyl radical having at most 4 carbon atoms) and their salts with organic or inorganic acids, and the preparation thereof by reacting a compound of the general formula <FORM:0926816/IV(a)/2> (wherein R1 represents a C1-4 alkyl radical or an aralkyl, a -alkoxyalkyl or tetrahydropyranyl radical) with a reactive ester of an alcohol of the general formula HO-X-Am1 (III) (wherein Am1 has the meanings given for Am other than monoalkylamino, or represents an N - arylmethyl - alkylamino or N - acyl - alkylamino group) in the presence of an alkaline condensing agent, or reacting a reactive ester of a compound of the general formula <FORM:0926816/IV(a)/3> with a compound of the general formula Am-H (VI) or Am1-H (VII) in the presence of an acid binding agent, or (in certain cases) treating a compound of the general formula <FORM:0926816/IV(a)/4> (wherein Am11 represents an amino or C1-4 alkylamino group) with an appropriate alkylating agent, or reducing a compound of the general formula <FORM:0926816/IV(a)/5> (wherein X1 and Am111 have the meanings given for X and Am except that in at least one of them a methylene group attached to a nitrogen atom is replaced by a carbonyl group) by means of an alkali metal-earth metal hydride, and, in any of the foregoing cases where necessary, subjecting the product to acid hydrolysis, transacetalization or hydrogenolysis, or, when -OR is a hydroxy group in the 2-position, by oxidizing a compound of the general formula <FORM:0926816/IV(a)/6> with oxygen or hydrogen peroxide in a neutral to weakly acid aqueous solution in the presence of a compound containing the grouping - CO - C(OH) = C(OH) - or -CO-CO-CO and of iron, nickel, cobalt or manganese ions and, if desired, a complex former. Ethers of the general formula (II) above are prepared by diazotizing an amine of the general formula <FORM:0926816/IV(a)/7> (wherein Y represents an acyl radical easily split off), decomposing the diazonium salt, by heating with water or aqueous acid, to form a hydroxy compound of the general formula <FORM:0926816/IV(a)/8> and reacting this with an alkylating agent, an aralkyl halide, or an a -halo dialkyl ether, in the presence of an acid-binding agent, or with dihydropyran or a vinyl alkyl ether, before or after removal of the acyl radical Y by hydrolysis. Compounds (XII) in which Y is benzoyl or acetyl and the hydroxy group is in the 4-position are also obtainable by treating iminodibenzyl with an equimolecular proportion of benzoyl or acetyl peroxide. 2-Hydroxyiminodibenzyl is obtainable by hydrolysing corresponding compounds (XII) or by subjecting iminodibenzyl to oxidation with a solution of potassium nitrosodisulphonate and reducing the resulting 2-oxoderivative. Amines of the general formula (XI) are obtainable by subjecting corresponding compounds containing an acetyl group in place of the amino group to Schmidt reaction conditions and then partially hydrolysing the resulting acetamido compounds. Reactive esters of compounds of the general formula (V) above are prepared by reacting alkali metal compounds of OR1- substituted iminodibenzyls with preferably mixed diesters (e.g. dihalides or halide-sulphonates) of alkylene glycols, or with alkylene oxides followed by treatment of the hydroxyalkyl compounds (V) so obtained with inorganic acid halides, arylsulphonic acid chlorides or methane sulphochloride. Amides of the general formula (IX) above are prepared as follows: when there is a carbonyl group in X1 only, adjacent to Am11 by reacting compounds (II) with bromoalkanecarboxylic acid dialkylamides, pyrrolidides, piperidides, morpholides or 4-alkylpiperazides when there is a carbonyl group in X1 only, adjacent to the iminodibenzyl nucleus, by reacting alkali metal derivatives of compounds (II) with haloalkanecarboxylic acid halides and reacting the resulting 5-haloalkanoyl compounds with alkylamines, dialkylamines or piperidine when there are one or two carbonyl groups in Am111 only, by reacting reactive esters of compounds (V) with alkali metal compounds of, for example, alkanecarboxylic amides or N-alkylamides, di(alkanecarboxylic)amides, d -valerolactam, e -caprolactam, succinimide or glutarimide, or by acylating compounds (VIII). Aminoalkyl-iminodibenzyls of the general formula (X) above are prepared by reacting iminodibenzyl with a dialkylaminoalkyl halide, or a 5-haloalkyliminodibenzyl with an amine (VI). Pharmaceutical compositions.-The compounds of general formula (I) above may be administered orally, in the form of aqueous solutions of their non-toxic acid addition salts, or parenterally, as antiallergic, sedative, serotonin-antagonistic, antipyretic or thymoleptic agents.
ES0258418A 1959-05-28 1960-05-27 Improvements in and relating to n-heterocyclic compounds Expired ES258418A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH7368359 1959-05-28
CH98160A CH381692A (en) 1960-01-29 1960-01-29 Process for the preparation of new iminodibenzyl derivatives
CH97960A CH378893A (en) 1960-01-29 1960-01-29 Process for the preparation of new N-heterocyclic compounds

Publications (1)

Publication Number Publication Date
ES258418A1 true ES258418A1 (en) 1960-11-16

Family

ID=27172570

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0258418A Expired ES258418A1 (en) 1959-05-28 1960-05-27 Improvements in and relating to n-heterocyclic compounds

Country Status (3)

Country Link
BE (1) BE591293A (en)
ES (1) ES258418A1 (en)
GB (1) GB926816A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013078244A1 (en) 2011-11-21 2013-05-30 Promega Corporation Carboxy x rhodamine analogs

Also Published As

Publication number Publication date
BE591293A (en) 1960-11-28
GB926816A (en) 1963-05-22

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