GB1113802A - Improvements in or relating to substituted quinolines and the manufacture thereof - Google Patents

Improvements in or relating to substituted quinolines and the manufacture thereof

Info

Publication number
GB1113802A
GB1113802A GB2165565A GB2165565A GB1113802A GB 1113802 A GB1113802 A GB 1113802A GB 2165565 A GB2165565 A GB 2165565A GB 2165565 A GB2165565 A GB 2165565A GB 1113802 A GB1113802 A GB 1113802A
Authority
GB
United Kingdom
Prior art keywords
formulae
phenols
chloro
quinolinylamino
followed
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
GB2165565A
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.)
University of Michigan
Original Assignee
University of Michigan
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 University of Michigan filed Critical University of Michigan
Publication of GB1113802A publication Critical patent/GB1113802A/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
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
    • 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
    • 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
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms

Abstract

Novel 4 - (7 - chloro - 4 - quinolinylamino)-phenols of the formulae <FORM:1113802/C2/1> <FORM:1113802/C2/2> <FORM:1113802/C2/3> wherein R is a lower alkyl radical containing from 1 to 6 carbon atoms, and pharmaceutically acceptable acid addition salts thereof are prepared by condensatio of p-amino-phenols of the formulae <FORM:1113802/C2/4> with 4,7-dichloroquinoline, followed by reaction with pyrrolidine and formaldehyde in the case of 4 - (7 - chloro - 4 - quinolinylamino) - phenols of the first and second formulae above, and optional conversion of the resulting bases to pharmaceutically acceptable acid addition salts thereof. Pharmaceutical compositions useful in the treatment of malarial infections, rheumatoid arthritis and extraintestinal amebiasis, comprise as active ingredient a 4-(7-chloro-4-quinolinylamino)-phenol of the first, second or third formula above, together with a pharmaceutically acceptable carrier. p-Amino-phenols of the fourth and fifth formulae above are prepared by reaction of a -chloro-4-nitro-o-cresol with an amine of the formulae <FORM:1113802/C2/5> <FORM:1113802/C2/6> respectively, followed by reduction of the resulting p-nitro-phenols of the corresponding formulae <FORM:1113802/C2/7> <FORM:1113802/C2/8> The p-aminophenol of the sixth formula above is prepared by reaction of p-acetamidophenol, formaldehyde and pyrrolidine, followed by hydrolysis of the resulting 2,6-bis-(pyrrolidinomethyl)-4-acetamido-phenol.
GB2165565A 1964-06-01 1965-05-21 Improvements in or relating to substituted quinolines and the manufacture thereof Expired GB1113802A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US37181164A 1964-06-01 1964-06-01

Publications (1)

Publication Number Publication Date
GB1113802A true GB1113802A (en) 1968-05-15

Family

ID=23465490

Family Applications (3)

Application Number Title Priority Date Filing Date
GB2165565A Expired GB1113802A (en) 1964-06-01 1965-05-21 Improvements in or relating to substituted quinolines and the manufacture thereof
GB5237767A Expired GB1113803A (en) 1964-06-01 1965-05-21 Improvements in or relating to substituted quinolines and the manufacture thereof
GB5237867A Expired GB1113804A (en) 1964-06-01 1965-05-21 Improvements in or relating to substituted quinolines and the manufacture thereof

Family Applications After (2)

Application Number Title Priority Date Filing Date
GB5237767A Expired GB1113803A (en) 1964-06-01 1965-05-21 Improvements in or relating to substituted quinolines and the manufacture thereof
GB5237867A Expired GB1113804A (en) 1964-06-01 1965-05-21 Improvements in or relating to substituted quinolines and the manufacture thereof

Country Status (4)

Country Link
DE (2) DE1620228A1 (en)
GB (3) GB1113802A (en)
IL (1) IL23555A (en)
NL (1) NL6506950A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012048894A1 (en) * 2010-10-14 2012-04-19 Julius-Maximilians-Universität Würzburg Hybrid compounds of 4- and 8-aminoquinolines for the prophylactic and therapeutic treatment of malaria and other parasitic diseases

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020042537A1 (en) * 2000-07-13 2002-04-11 Ajinomoto Co., Inc. Method for producing lysine derivative
JP2006522814A (en) * 2003-04-11 2006-10-05 タイゲン・バイオテクノロジー Aminoquinoline compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012048894A1 (en) * 2010-10-14 2012-04-19 Julius-Maximilians-Universität Würzburg Hybrid compounds of 4- and 8-aminoquinolines for the prophylactic and therapeutic treatment of malaria and other parasitic diseases

Also Published As

Publication number Publication date
GB1113804A (en) 1968-05-15
DE1620228A1 (en) 1970-06-04
DE1620229A1 (en) 1970-06-04
IL23555A (en) 1969-05-28
NL6506950A (en) 1965-12-02
GB1113803A (en) 1968-05-15

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