GB1123601A - New derivatives of trans-4a-acylaminodecalin - Google Patents

New derivatives of trans-4a-acylaminodecalin

Info

Publication number
GB1123601A
GB1123601A GB1061365A GB1061365A GB1123601A GB 1123601 A GB1123601 A GB 1123601A GB 1061365 A GB1061365 A GB 1061365A GB 1061365 A GB1061365 A GB 1061365A GB 1123601 A GB1123601 A GB 1123601A
Authority
GB
United Kingdom
Prior art keywords
radical
alkyl
halogen
hydroxy
alkoxy
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
GB1061365A
Inventor
Philip Neil Edwards
Douglas Lintin Swallow
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB1061365A priority Critical patent/GB1123601A/en
Priority to FR53082A priority patent/FR1491242A/en
Priority to FR65118A priority patent/FR5585M/fr
Publication of GB1123601A publication Critical patent/GB1123601A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring

Landscapes

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

Abstract

Novel trans-4a-acylaminodecalin derivatives of the general formula <FORM:1123601/C2/1> (wherein R1 represents H or an alkyl or alkenyl radical and R2 represents an unsubstituted alkyl radical of at least 2 carbon atoms; a cycloalkyl radical optionally substituted by an aryl radical; or an alkyl radical bearing one or more substituents selected from halogen atoms, alkoxy and alkenyl radicals, and aryl, aryloxy, arylthio, arylamino, heterocyclyl, heterocyclyloxy and heterocyclythio radicals themselves optionally bearing one or more halogen, alkyl, alkoxy, aryloxy, acyl, hydroxy or nitro substituents, or R1 and R2 jointly form an alkylene radical, and wherein the decalin ring may optionally carry one or more halogen or OH substituents) are prepared as follows: (a) (when R1=H and the decalin ring is not further substituted) by reacting a carbonium ion of the formula <FORM:1123601/C2/2> with a cyano compound R2CN in the presence of a strong acid; (b) (when R1 is an alkyl or alkenyl radical) by reacting the corresponding compound in which R1 is H with an alkylating or alkenylating agent R1X (wherein X is a halogen atom, an alkane- or arene-sulphonyloxy radical or a sulphate radical); (e) (when R2 is a radical -CH2R4, where R4 is an alkoxy radical or an optionally substituted aryloxy, arylthio, arylamino, heterocyclyl, heterocyclyloxy or heterocyclythio radical as defined above) by reacting a compound of the formula <FORM:1123601/C2/3> (wherein Y is a halogen atom, an alkane- or arene-sulphonyloxy radical or a sulphate radical and the decalin ring may be further substituted as indicated above) with a compound R4H; (d) (in all cases where R1 and R2 are not joined together to form an alkylene radical) by acylation of the corresponding compounds containing H in place of -COR2, by means of an acylating agent derived from an acid R2COOH. The carbonium ion in process (a) may be formed by treating a - or b -decalol, D 1,8a- or D 4a ,8a-octalin or 2 - hydroxycyclohexanespirocyclopentane with a strong acid. 4 - Hydroxy - 2 - n - propylpyrimidin - 5 -ylacetic acid is prepared by heating diethyl 2-formylsuccinate with butyramidine hydrochloride in a solution of sodium in ethanol and hydrolysing the resulting ethyl-4-hydroxy-2-n-propylpyrimidin-5-ylacetate. 1b - Hydroxy - 4ab - trans - decalylamine hydrochloride is prepared by shaking 1b ,11-epoxy - 4ab - ethylideneamino - trans - decalin with hot aqueous caustic soda, isolating the resulting base and treating it with ethereal HCl solution.ALSO:Pharmaceutical compositions, useful for treating viral diseases, comprise, in association with a pharmaceutically acceptable diluent or carrier, one or more trans-4a-acylaminodecalin derivatives of the general formula:- <FORM:1123601/A5-A6/1> (wherein R1 represents H or an alkyl or alkenyl radical and R2 represents an unsubstituted alkyl radical of at least 2 carbon atoms; a cycloalkyl radical optionally substituted by an aryl radical; or an alkyl radical bearing one or more substituents selected from halogen atoms, alkoxy and alkenyl radicals, and aryl, aryloxy, arylthio, arylamino, heterocyclyl, heterocyclyloxy and heterocyclylthio radicals themselves optionally bearing one or more halogen, alkyl, alkoxy, aryloxy, acyl, hydroxy or nitro substituents, or R1 and R2 jointly form an alkylene radical, and wherein the decalin ring may optionally carry one or more halogen or hydroxy substituents), with or without one or more known antiviral agents, e.g. 1-adamantanamine hydrochloride.
GB1061365A 1965-03-12 1965-03-12 New derivatives of trans-4a-acylaminodecalin Expired GB1123601A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB1061365A GB1123601A (en) 1965-03-12 1965-03-12 New derivatives of trans-4a-acylaminodecalin
FR53082A FR1491242A (en) 1965-03-12 1966-03-11 New derivatives of decalin
FR65118A FR5585M (en) 1965-03-12 1966-06-10

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1061365A GB1123601A (en) 1965-03-12 1965-03-12 New derivatives of trans-4a-acylaminodecalin

Publications (1)

Publication Number Publication Date
GB1123601A true GB1123601A (en) 1968-08-14

Family

ID=9971096

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1061365A Expired GB1123601A (en) 1965-03-12 1965-03-12 New derivatives of trans-4a-acylaminodecalin

Country Status (2)

Country Link
FR (1) FR5585M (en)
GB (1) GB1123601A (en)

Also Published As

Publication number Publication date
FR5585M (en) 1967-12-04

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