GB770624A - Substituted endoxy-perhydroisoindolines - Google Patents
Substituted endoxy-perhydroisoindolinesInfo
- 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
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.
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)
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 |
-
1954
- 1954-07-02 GB GB19424/54A patent/GB770624A/en not_active Expired
Cited By (2)
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 |
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