GB970949A - New 6-aminoquinoline derivatives - Google Patents

New 6-aminoquinoline derivatives

Info

Publication number
GB970949A
GB970949A GB5353/62A GB535362A GB970949A GB 970949 A GB970949 A GB 970949A GB 5353/62 A GB5353/62 A GB 5353/62A GB 535362 A GB535362 A GB 535362A GB 970949 A GB970949 A GB 970949A
Authority
GB
United Kingdom
Prior art keywords
amino
quinoline
group
prepared
specifications
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
GB5353/62A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of GB970949A publication Critical patent/GB970949A/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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • 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
    • C07D215/20—Oxygen 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
    • C07D215/36—Sulfur 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
    • C07D215/42—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
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Quinoline Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises 6-(aminoalkylamino)-quinoline derivatives which are substituted in the 5- and 8-positions by alkoxy, alkenyloxy, aralkyl or aryl ether groups, with or without a further alkyl group in a position other than the 5- or 8-position, and their pharmaceutically acceptable non-toxic neutral salts thereof with inorganic and organic acids. The compounds may be prepared by (a) reacting an appropriate 6-amino quinoline with a reactive ester of an aminoalcohol or condensing the aminoalcohol themselves with the 6-aminoquinoline; (b) by exchanging a group in the 6-position of an appropriate quinoline for an amino alkylamino radical by reaction of the group (e.g. hydroxyl) with an amino alkylamine; (c) by reacting 8-hydroxyquinoline compounds and their derivatives which also carry an exchangeable substituent in the 6-position, and which also carry in the 5-position a substituent promoting the exchangeability of the adjacent 6-position with an aminoalkylamine and converting the substituents in the 5- and 8-positions to ether groups as defined above; (d) introducing a 5-hydroxyl group or its ether into the 5-position of an 8-hydroxy -6- aminoalkylamino quinoline by preparing the 5-azo-or-5-nitrocompound reducing this to the 5-amino derivative and converting the amino group to an etherified hydroxyl group, (e) forming a Schiffs base between a 6-aminoquinoline and a basic carbonyl compound and reducing the base so formed; (f) by a ring closure, quinoline, synthesis, or (g) by a stepioise procedure to build up the amino alkyl chain in the 6-aminoalkylamino residue. 6-Amino-5, 8-dimethoxy-, -5, 8-diethoxy-, -5- phenoxy -8- methoxy-, and -5, 8-dimethoxy -2- methyl-quinolines are prepared by reduction of the corresponding nitro compounds. 6-Hydroxy-5, 8-dimethoxy-quinoline is prepared from the 6-amino compound by diazotistation. Specifications 267,169 and 433,625 and German Specifications 602,049 and 642,378 are referred to.ALSO:A red dyestuff, 6-(5-diethylamino-pentyl-2-amino) - 5 - phenylazo - 8 - methoxyquinoline, is prepared from diazotized aniline and 6-(5-diethylaminopentyl - 2 - amino) - 8 - methoxyquinoline. Specifications 267,169 and 433,625 and German Specifications 602,049 and 642,378 are referred to.
GB5353/62A 1961-02-24 1962-02-12 New 6-aminoquinoline derivatives Expired GB970949A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DESCH29286A DE1186861B (en) 1961-02-24 1961-02-24 Process for the preparation of 6- (5'-diaethylaminopentyl-2'-amino) -5,8-dimethoxyquinolines or quinaldines useful as malaria remedies

Publications (1)

Publication Number Publication Date
GB970949A true GB970949A (en) 1964-09-23

Family

ID=7431378

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5353/62A Expired GB970949A (en) 1961-02-24 1962-02-12 New 6-aminoquinoline derivatives

Country Status (4)

Country Link
BE (1) BE614245A (en)
CH (1) CH422788A (en)
DE (1) DE1186861B (en)
GB (1) GB970949A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3614756A1 (en) * 1986-04-30 1987-11-05 Ruetgerswerke Ag METHOD FOR THE PRODUCTION OF 5-ALKYLCHINOLIN ACIDS AND AGENT FOR IMPLEMENTING THE METHOD

Also Published As

Publication number Publication date
BE614245A (en) 1962-08-22
CH422788A (en) 1966-10-31
DE1186861B (en) 1965-02-11

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