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ES446538A1 - 77hydroxyybenzo *11* quinolysinee22carboxylic acid and derivative thereof - Google Patents

77hydroxyybenzo *11* quinolysinee22carboxylic acid and derivative thereof

Info

Publication number
ES446538A1
ES446538A1 ES446538A ES446538A ES446538A1 ES 446538 A1 ES446538 A1 ES 446538A1 ES 446538 A ES446538 A ES 446538A ES 446538 A ES446538 A ES 446538A ES 446538 A1 ES446538 A1 ES 446538A1
Authority
ES
Spain
Prior art keywords
ethyl
methyl
formamido
acetamido
nitro
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
ES446538A
Other languages
Spanish (es)
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.)
Riker Laboratories Inc
Original Assignee
Riker Laboratories Inc
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
Priority claimed from US05/567,510 external-priority patent/US3985753A/en
Priority claimed from US05/567,494 external-priority patent/US3976651A/en
Application filed by Riker Laboratories Inc filed Critical Riker Laboratories Inc
Publication of ES446538A1 publication Critical patent/ES446538A1/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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • 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
    • C07D215/18—Halogen atoms or nitro radicals
    • 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
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Quinoline Compounds (AREA)

Abstract

Procedure for preparing substituted benzoquinolizines, of formulas: **(See formula)** wherein R1 is hydrogen, methyl or ethyl; R2 is methyl, ethyl, halogen, hydroxy, nitro, amino, acetamido, or formamido; n is 0, 1 or 2 and, when n is 2, R2 can be methylenedioxy or ethylene dioxy attached to adjacent carbon atoms and, when R is ethyl, methoxy, nitro, amino, acetamido or formamido and n is 2, each R2 must to be different; and its lower alkyl esters or pharmaceutically acceptable salts; characterized in that: 1) an alkoxyquinoline of the formula is reacted: **(See formula)** wherein R2 is methyl, ethyl, methoxy, halogen, hydroxy, nitro, amino, acetamido, or formamido; n is 0, 1 or 2 and, when n is 2, R2 can be methylenedioxy or ethylenedioxy attached to adjacent carbon atoms and, when R2 is ethyl, methoxy, nitro, amino, acetamido or formamido and n is 2, each R must be different, and alq is alkyl with 1 to 4 carbon atoms, with methyl- or ethyl-lithium, under dry conditions in an inert solvent, at a temperature of -30 to 0ºC, followed by acid hydrolytic dissociation of the alkoxy group to form a 4-oxo-1,2, -3,4-tetrahydroquinoline intermediate of formula: **(See formula)** where R is methyl or ethyl. (Machine-translation by Google Translate, not legally binding)
ES446538A 1975-04-14 1976-03-31 77hydroxyybenzo *11* quinolysinee22carboxylic acid and derivative thereof Expired ES446538A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US05/567,510 US3985753A (en) 1975-04-14 1975-04-14 7-Hydroxy-benzo[ij]quinolizine-2-carboxylic acids and derivatives thereof
US05/567,494 US3976651A (en) 1975-04-14 1975-04-14 7-Hydroxy-benzo[ij]quinolizine-2-carboxylic acids, intermediates, and a method for their production

Publications (1)

Publication Number Publication Date
ES446538A1 true ES446538A1 (en) 1977-10-16

Family

ID=27074500

Family Applications (1)

Application Number Title Priority Date Filing Date
ES446538A Expired ES446538A1 (en) 1975-04-14 1976-03-31 77hydroxyybenzo *11* quinolysinee22carboxylic acid and derivative thereof

Country Status (6)

Country Link
JP (1) JPS51127099A (en)
AU (1) AU1295276A (en)
DE (1) DE2616268A1 (en)
ES (1) ES446538A1 (en)
FR (1) FR2307533A1 (en)
IT (1) IT1060213B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4400386A (en) * 1981-11-06 1983-08-23 Riker Laboratories, Inc. Antimicrobial derivatives of 8-amino and 8-aminomethyl benzo(ij)quinolizine
US4472407A (en) * 1983-03-17 1984-09-18 Riker Laboratories, Inc. Antimicrobial 8-alkoxy-6,7-dihydro-5-methyl-9-fluoro-1-oxo-1H,5H-benzo[ij]qu
CA1253154A (en) * 1985-05-24 1989-04-25 Atsushi Takagi Benzo¬ij|quinolizine-2-carboxylic acid derivatives
JPS63130585A (en) * 1986-11-21 1988-06-02 Tokyo Tanabe Co Ltd 4-alkoxyquinoline compound and production thereof

Also Published As

Publication number Publication date
DE2616268A1 (en) 1976-10-28
IT1060213B (en) 1982-07-10
JPS51127099A (en) 1976-11-05
AU1295276A (en) 1977-10-20
FR2307533A1 (en) 1976-11-12

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