GB770624A - Substituted endoxy-perhydroisoindolines - Google Patents

Substituted endoxy-perhydroisoindolines

Info

Publication number
GB770624A
GB770624A GB19424/54A GB1942454A GB770624A GB 770624 A GB770624 A GB 770624A GB 19424/54 A GB19424/54 A GB 19424/54A GB 1942454 A GB1942454 A GB 1942454A GB 770624 A GB770624 A GB 770624A
Authority
GB
United Kingdom
Prior art keywords
methyl
endoxyperhydroisoindoline
dimethyl
salts
alkyl radical
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
GB19424/54A
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.)
GESCHICKTER FUND MED RES
Original Assignee
GESCHICKTER FUND MED RES
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 GESCHICKTER FUND MED RES filed Critical GESCHICKTER FUND MED RES
Publication of GB770624A publication Critical patent/GB770624A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/18—Bridged systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises 4,7-endoxyperhydroisoindolines of the general formul <FORM:0770624/IV(b)/1> and <FORM:0770624/IV(b)/2> wherein R1 represents a straight-chain alkyl radical or a branched chain alkyl radical containing one branched chain and having 1 to 12 carbon atoms, x is a whole number from 1 to 6, and R represents an alkyl radical containing from 1 to 6 carbon atoms or <FORM:0770624/IV(b)/3> represents the residue a saturated nitrogen-containing heterocyclic base, and wherein the <FORM:0770624/IV(b)/4> ring may contain alkyl substituents, and the acid addition and quaternary salts thereof, and the preparation thereof by reacting the required perhydrophthalic anhydride with the required amine to form an acid amide which is cyclised to an imide by heating, and the imide is reduced electrolytically or by means of lithium aluminium hydride to form the required 4,7-endoxyperhydroisoindoline, and the acid addition, and bis-quaternary salts may then be prepared by the usual methods. The group <FORM:0770624/IV(b)/5> may represent the residue of piperidine, morpholine or pyrrolidine, and R1 may represent a methyl, isopropyl or isoamyl radical. The alkyl ring-substituted compounds of the above perhydroisoindolines may be a 4-methyl-, 4,7-dimethyl-, 8,9-dimethyl- or 4,5,6,7-tetramethyl-4,7-endoxyperhydroisoindoline. The cyclization step may be brought about by heating for 2 to 5 hours, a suitable temperature being in the range of 160 DEG to 180 DEG C. In the examples the following compounds are prepared: N-b -dimethylaminoethyl- and N-b -diethylaminoethylperhydro-4,7-endoxyisoindoline and the dihydrochloride and bis-methonium iodide salts thereof, 4,7-dimethyl-, 4-methyl-, and 8,9-dimethyl - N - b - dimethylaminoethyl - 4,7 - endoxyperhydroisoindoline and the dihydrochloride and dimethiodide salts thereof, N-methyl-4-methyl - 4,7 - endoxyperhydroisoindoline, and N - g - dimethylaminopropyl-, N - g - diethylaminopropyl -, N - g - dibutylaminopropyl -, N - b - dihexylaminoethyl -, N - o - diethylaminohexyl -, b - (N - morpholino) - ethyl -, g - (N - morpholino) propyl - and b - (N - piperidino) ethyl - perhydro - 4,7 - endoxyisoindoline. Specification 770,625 is referred to.
GB19424/54A 1953-10-20 1954-07-02 Substituted endoxy-perhydroisoindolines Expired GB770624A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US770624XA 1953-10-20 1953-10-20

Publications (1)

Publication Number Publication Date
GB770624A true GB770624A (en) 1957-03-20

Family

ID=22135857

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19424/54A Expired GB770624A (en) 1953-10-20 1954-07-02 Substituted endoxy-perhydroisoindolines

Country Status (1)

Country Link
GB (1) GB770624A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3092630A (en) * 1958-12-19 1963-06-04 Gen Aniline & Film Corp Preparation of nu-substituted-3-morpholones
WO1994009006A1 (en) * 1992-10-09 1994-04-28 The Du Pont Merck Pharmaceutical Company 3a,6-bridged hexahydroisoindoles and related hydroisoquinolines and hydrobenzazepines and their use as radioimaging and pharmaceutical agents

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3092630A (en) * 1958-12-19 1963-06-04 Gen Aniline & Film Corp Preparation of nu-substituted-3-morpholones
WO1994009006A1 (en) * 1992-10-09 1994-04-28 The Du Pont Merck Pharmaceutical Company 3a,6-bridged hexahydroisoindoles and related hydroisoquinolines and hydrobenzazepines and their use as radioimaging and pharmaceutical agents

Similar Documents

Publication Publication Date Title
GB952187A (en) Thermographic copying materials
YU41886B (en) Process for obtaining a new pyrrolyl- pyridazine amine derivatives
GB770624A (en) Substituted endoxy-perhydroisoindolines
GB913866A (en) Improvements in or relating to amino-norcamphane compounds
ES436109A1 (en) Procedure for the preparation of new derivatives of pyridine. (Machine-translation by Google Translate, not legally binding)
GB933504A (en) New piperidine derivatives and methods for preparing the same
GB774883A (en) Phenthiazine derivatives
ES448594A1 (en) Diarylbutanolamines
GB770625A (en) Substituted endoxy-perhydrophthalimides
ES306767A1 (en) Procedure for the preparation of new basic derivatives of tiepine and oxepine. (Machine-translation by Google Translate, not legally binding)
GB866791A (en) A process for preparing new physiologically effective salts of the aminoalkyl derivatives of homophenothiazine
ES276073A1 (en) Procedure for the preparation of new derivatives of oxazolidinone (Machine-translation by Google Translate, not legally binding)
ES264624A1 (en) New phenothiazine derivatives and a process for the production thereof
ES451293A1 (en) A procedure for the preparation of tienotiacin derivatives. (Machine-translation by Google Translate, not legally binding)
ES223287A1 (en) A procedure for manufacturing amidas of N-alkyl piperidin monocarboxylic acid and N-alkyl pirrolidin alpha-monocarboxylic acid (Machine-translation by Google Translate, not legally binding)
ES369751A1 (en) Procedure for the preparation of new indol derivatives. (Machine-translation by Google Translate, not legally binding)
ES444644A1 (en) Process for the preparation of thieno-pyridine derivatives
ES259353A1 (en) Procedure for the preparation of new derivatives of phenoxyactic acid (Machine-translation by Google Translate, not legally binding)
GB739944A (en) New derivatives of colchicoside and process for their preparation
ES223288A1 (en) A procedure for the preparation of amidas of N-alkyl piperidin monocarboxylic acid and N-alkyl pirrolidin alpha-monocarboxylic acid (Machine-translation by Google Translate, not legally binding)
ES412484A1 (en) Procedure for the preparation of carbostirilic derivatives. (Machine-translation by Google Translate, not legally binding)
ES258045A1 (en) Procedure for the obtaining of derivatives of the ftalimiento for the obtaining of ftalimidina (Machine-translation by Google Translate, not legally binding)
ES245070A3 (en) Procedure for the obtaining of new biscuaternary compounds (Machine-translation by Google Translate, not legally binding)
GR18381B (en) METHOD OF PREPARATION OF AMIDES OF N - ALKYLO - PEPERIDINE MONOCARBOXYLIC ACID AND N - ALKYLO - PYROROLIDINE - A - MONOCARBOXYLIC ACID.
ES247608A1 (en) Procedure for the obtaining of 1.1 sulfamilo dioxides -3,4 dihydro 1-2,4 benzotiadicin (Machine-translation by Google Translate, not legally binding)