GB1113804A - 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
GB1113804A
GB1113804A GB5237867A GB5237867A GB1113804A GB 1113804 A GB1113804 A GB 1113804A GB 5237867 A GB5237867 A GB 5237867A GB 5237867 A GB5237867 A GB 5237867A GB 1113804 A GB1113804 A GB 1113804A
Authority
GB
United Kingdom
Prior art keywords
methyl
chloro
quinoline
amino
formula
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
GB5237867A
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 GB1113804A publication Critical patent/GB1113804A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/16Heterocyclic 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
    • C07D215/38Nitrogen atoms
    • C07D215/42Nitrogen atoms attached in position 4
    • C07D215/44Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/16Heterocyclic 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
    • C07D215/38Nitrogen atoms
    • C07D215/40Nitrogen atoms attached in position 8
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/16Heterocyclic 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
    • C07D215/38Nitrogen atoms
    • C07D215/42Nitrogen atoms attached in position 4
    • C07D215/46Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms

Landscapes

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

Abstract

Novel 7 - chloro - 4 - (1 - methyl - 2 - piperidinylmethylamino) - quinoline, 7 - chloro - 4 - (1 - methyl - 3 - piperidinylmethylamino)-quinoline, 7 - chloro - 4 - (4 - amino - 4 - methylpentylamino) - quinoline, 4 - substituted - 7 - chloroquinolines of the formula <FORM:1113804/C2/1> wherein R1 and R2 are lower alkyl radicals containing from 1 to 4 carbon atoms or R1 and R2, taken together with the N atom to which they are attached, form a pyrrolidino, piperidino or morpholino ring, and pharmaceutically acceptable acid addition salts thereof are prepared by condensation of 2-aminomethyl-1-methylpiperidine, 3 - amino - methyl - 1 - methylpiperidine, 1 - amino - 4 - methyl - 4 - nitropentane or a 1 - amino - 4 - methyl - 4 - aminopentane derivative of the formula <FORM:1113804/C2/2> respectively, with 7-chloro-4-phenoxyquinoline hydrochloride; followed by hydrogenation, in the case of 7-chloro-4-(4-amino-4-methylpentylamino)-quinoline, of the resulting 7-chloro-4-(4-methyl-4-nitropentylamino)-quinoline; followed by optional conversion to a pharmaceutically acceptable acid addition salt of the product. Pharmaceutical compositions, having anti-inflammatory and anti-amebic activity and being useful in the treatment of malarial infections, comprise as active ingredient 7-chloro-4 - (1 - methyl - 2 - piperidinylmethylamino)-quinoline, 7 - chloro - 4 - (1 - methyl - 3 - piperidinylmethylamino) - quinoline, 7 - chloro - 4 - (4-amino - 4 - methylpentylamino) - quinoline, a 4 - substituted - 7 - chloro - quinoline of the first formula above, or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutically acceptable carrier. 2 - Aminomethyl - 1 - methylpiperidine is prepared by treating 2-(acetamidomethyl)-pyridine with iodomethane, converting the resulting 2-(acetamidomethyl) - 1 - methylpyridinium iodide to the corresponding chloride with silver chloride, reducing the chloride to give 2-(acetamidomethyl) - 1 - methylpiperidine and finally hydrolysing. 1 - Amino - 4 - methyl - 4 - nitropentane is prepared by reacting 1-bromo-4-methyl - 4 - nitropentane with potassium phthalimide and treating the resulting 4-methyl-4 - nitro - 1 - phthalimidopentane with hydrazine hydrate. 1 - Amino - 4 - methyl - 4 - aminopentane derivatives of the second formula above are prepared by reacting 2,5-dibromo-2-methylpentane with potassium phthalimide, reacting the 4 - bromo - 4 - methyl - 1 - phthalimidopentane so obtained with a secondary amine of the formula R1R2NH and then treating the resulting phthalimide of the formula <FORM:1113804/C2/3> with hydrazine hydrate.
GB5237867A 1964-06-01 1965-05-21 Improvements in or relating to substituted quinolines and the manufacture thereof Expired GB1113804A (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
GB1113804A true GB1113804A (en) 1968-05-15

Family

ID=23465490

Family Applications (3)

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
GB2165565A Expired GB1113802A (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 Before (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
GB2165565A Expired GB1113802A (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) GB1113803A (en)
IL (1) IL23555A (en)
NL (1) NL6506950A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1179599A3 (en) * 2000-07-13 2003-07-09 Ajinomoto Co., Inc. Method for producing lysine derivative
EP1613322A2 (en) * 2003-04-11 2006-01-11 Taigen Biotechnology Aminoquinoline compounds

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102010048476A1 (en) * 2010-10-14 2012-08-23 Julius-Maximilians-Universität Würzburg Hybrid compounds of 4- and 8-aminoquinolines for the prophylactic and therapeutic treatment of malaria and other parasitic diseases

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1179599A3 (en) * 2000-07-13 2003-07-09 Ajinomoto Co., Inc. Method for producing lysine derivative
US6664412B2 (en) 2000-07-13 2003-12-16 Ajinomoto Co., Inc. Method for producing lysine derivative
EP1613322A2 (en) * 2003-04-11 2006-01-11 Taigen Biotechnology Aminoquinoline compounds
EP1613322A4 (en) * 2003-04-11 2008-08-13 Taigen Biotechnology Co Ltd Aminoquinoline compounds

Also Published As

Publication number Publication date
IL23555A (en) 1969-05-28
NL6506950A (en) 1965-12-02
DE1620229A1 (en) 1970-06-04
GB1113803A (en) 1968-05-15
GB1113802A (en) 1968-05-15
DE1620228A1 (en) 1970-06-04

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