GB589152A - Improvements in or relating to new antimalarials and process of producing the same - Google Patents

Improvements in or relating to new antimalarials and process of producing the same

Info

Publication number
GB589152A
GB589152A GB94/45A GB9445A GB589152A GB 589152 A GB589152 A GB 589152A GB 94/45 A GB94/45 A GB 94/45A GB 9445 A GB9445 A GB 9445A GB 589152 A GB589152 A GB 589152A
Authority
GB
United Kingdom
Prior art keywords
epichlorohydrin
reacting
methyl
methoxy
aminoquinoline
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
GB94/45A
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB589152A publication Critical patent/GB589152A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Substituted quinolines which are antimalarial compounds having the formula <FORM:0589152/IV/1> in which R represents hydrogen or a lower alkyl radical containing not more than 3 3 carbon atoms, R1 represents an alkyl, cycloalkyl or alkenyl radical in which the number of carbon atoms is from 1 to 10 inclusive, and R2 represents an alkyl, cycloalkyl or alkenyl radical in which the number of carbon atoms is from 3 to 10 inclusive, are obtained by condensing, e.g. by refluxing at a temperature of from 90 DEG to 130 DEG C. for 1 to 3 days, a 2-, 3-, or 4-methyl-6-methoxy-8-aminoquinoline or a hydrohalide thereof with a substituted haloamine of the following general formula <FORM:0589152/IV/2> (in which Ha represents chlorine or bromine) or a hydrohalide thereof. The 2-hydroxy-2-R-3-(R1, R2-disubstituted amino)-propyl halide is obtained by reacting an epichlorohydrin or epibromohydrin with the corresponding secondary amine. In examples: (1)-(6) 2-methyl-6 - methoxy - 8 - aminoquinoline is condensed with the product obtained by reacting (1) epichlorohydrin with diisobutylamine; (2) epichlorohydrin with di-n-butylamine; (3) epichlorohydrin with isopropyl - isobutylamine; (4) epichlorohydrin with n-butyl-isobutylamine; (5) b -methylepichlorohydrin with diisobutylamine; (6) b -methyl-epichlorohydrin with isobutyl-sec-butylamine; (7) 3-methyl-6-methoxy-8-amino quinoline is condensed with the product obtained by reacting b -methylepichlorohydrin with diallylamine; (8) 4-methyl - 6 - methoxy - 8 - aminoquinoline is condensed with the product obtained by reacting epichlorohydrin with isobutyl-cyclopentylamine. Alternatively the epibromohydrins may be used to produce the corresponding bromoamines and the same final products. Specification 267,169, [Class 2 (iii)], is referred to. The secondary amines used above are prepared by reacting a primary amine containing one desired R1 or R2 substituent with hydrogen and an aldehyde or ketone having the carbon skeleton of the other desired R1 or R2 substituent in the presence of a catalyst such as Raney nickel or Adams platinum oxide.
GB94/45A 1944-01-26 1945-01-01 Improvements in or relating to new antimalarials and process of producing the same Expired GB589152A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US589152XA 1944-01-26 1944-01-26

Publications (1)

Publication Number Publication Date
GB589152A true GB589152A (en) 1947-06-12

Family

ID=22019699

Family Applications (1)

Application Number Title Priority Date Filing Date
GB94/45A Expired GB589152A (en) 1944-01-26 1945-01-01 Improvements in or relating to new antimalarials and process of producing the same

Country Status (1)

Country Link
GB (1) GB589152A (en)

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