GB1237059A - Anti-virally effective quinoline derivatives - Google Patents

Anti-virally effective quinoline derivatives

Info

Publication number
GB1237059A
GB1237059A GB2481870A GB2481870A GB1237059A GB 1237059 A GB1237059 A GB 1237059A GB 2481870 A GB2481870 A GB 2481870A GB 2481870 A GB2481870 A GB 2481870A GB 1237059 A GB1237059 A GB 1237059A
Authority
GB
United Kingdom
Prior art keywords
compounds
formula
derivatives
alkoxycarbonyl
salts
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
GB2481870A
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.)
Warner Lambert Co LLC
Original Assignee
Warner Lambert Pharmaceutical 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 Warner Lambert Pharmaceutical Co filed Critical Warner Lambert Pharmaceutical Co
Publication of GB1237059A publication Critical patent/GB1237059A/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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Landscapes

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

Abstract

1,237,059. Quinoline derivatives. WARNER LAMBERT PHARMACEUTICAL CO. 26 Feb., 1969 [29 Feb., 1968; 30 Dec., 1968], No. 24818/70. Heading C2C. Novel quinoline derivatives of the formula wherein R 1 is H, halogen, OH, SH or alkylthio, R 2 is a free or esterified carboxyl group and R 3 is C 1-4 alkylenedioxy, and addition salts thereof with non-toxic pharmaceutically acceptable inorganic and organic acids, as well as the salts thereof with bases when R 2 is COOH, are prepared by cyclizing at an elevated temperature compounds of the Formula III above, and, if desired, converting the 3-alkoxycarbonyl-4- hydroxyquinoline derivatives into other compounds of Formula I by hydrolysis reaction with phosphorus oxyhalide, and esterification. Hydrohalides of compounds of Formula I above in which R 1 is halogen and R 2 is alkoxycarbonyl may also be obtained by refluxing compounds of Formula III above with a phosphorus halide or oxyhalide in an inert solvent, and the 3-alkoxycarbonyl-4-haloquinoline derivatives thus obtained, if desired, hydrolysed to the corresponding 3-carboxy-4-hydroxyquinoline derivatives, or reacted with potassium salts of alkyl mercaptans or sodium sulphide monohydrate to give compounds of Formula I above in which R 2 is alkoxyoarbonyl and R 1 is alkylthio and R 2 is COOH and R 1 is SH respectively. Diethyl 2 - (anilinomethylene)malonates of Formula III above in which R 3 is 3,4-ethylenedioxy, 2,3-methylenedioxy and 3,4-methylenedioxy are obtained by reacting the appropriately substituted anilines with diethyl ethoxymethylenemalonate. Pharmaceutical compositions, having antiviral activity and suitable for oral or parenteral administration, contain the above novel compounds or non-toxic salts thereof, in admixture with solid or sterile liquid pharmaceutically acceptable excipients.
GB2481870A 1968-02-29 1969-02-26 Anti-virally effective quinoline derivatives Expired GB1237059A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US70918068A 1968-02-29 1968-02-29
US78810168A 1968-12-30 1968-12-30

Publications (1)

Publication Number Publication Date
GB1237059A true GB1237059A (en) 1971-06-30

Family

ID=27108212

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2481870A Expired GB1237059A (en) 1968-02-29 1969-02-26 Anti-virally effective quinoline derivatives

Country Status (3)

Country Link
DE (1) DE1908548A1 (en)
FR (1) FR2002888A1 (en)
GB (1) GB1237059A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6069170A (en) * 1997-08-05 2000-05-30 Roche Vitamins Inc. Light screening compounds and compositions

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE795265A (en) * 1972-02-09 1973-08-09 Philips Nv NEW DERIVATIVES OF QUINOLEINE WITH PHARMACOLOGICAL ACTIVITY
FR2509728A1 (en) * 1981-07-17 1983-01-21 Roussel Uclaf NOVEL QUINOLINE DERIVATIVES, THEIR SALTS, PREPARATION METHOD, MEDICAMENT APPLICATION AND COMPOSITIONS COMPRISING THE SAME
EP0927164A1 (en) 1996-09-10 1999-07-07 PHARMACIA & UPJOHN COMPANY 8-hydroxy-7-substituted quinolines as anti-viral agents
ATE303993T1 (en) * 1997-12-22 2005-09-15 Pharmacia & Upjohn Co Llc 4-HYDROXYCHINOLINE-3-CARBOXAMIDE AND HYDRAZIDE AS ANTIVIRAL ACTIVES
US20100074949A1 (en) 2008-08-13 2010-03-25 William Rowe Pharmaceutical composition and administration thereof
PL1773816T3 (en) 2004-06-24 2015-06-30 Vertex Pharma Modulators of ATP-binding cassette transporters
HUE049976T2 (en) 2005-12-28 2020-11-30 Vertex Pharma Pharmaceutical compositions of the amorphous form of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
KR101852173B1 (en) 2009-03-20 2018-04-27 버텍스 파마슈티칼스 인코포레이티드 Process for making modulators of cystic fibrosis transmembrane conductance regulator
BR112014021090B1 (en) 2012-02-27 2023-01-24 Vertex Pharmaceuticals Incorporated PHARMACEUTICAL COMPOSITION AND USE OF N-[2,4-BIS(1,1-DIMETHYLethyl)-5-HYDROXYPHENYL]-1,4-DIHYDRO-4-OXOQUINOLINE3-CARBOXAMIDE IN THE PREPARATION OF THE SAME
KR20170063954A (en) 2014-10-07 2017-06-08 버텍스 파마슈티칼스 인코포레이티드 Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator
KR102135116B1 (en) * 2018-12-11 2020-07-17 재단법인 경기도경제과학진흥원 Antiviral Composition for Middle East Respiratory Syndrome Coronavirus Using Chloroxine or Analogues Thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1070223A (en) * 1965-03-09 1967-06-01 Ici Ltd Quinoline derivatives
GB1122323A (en) * 1966-08-04 1968-08-07 Ici Ltd Quinoline derivatives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6069170A (en) * 1997-08-05 2000-05-30 Roche Vitamins Inc. Light screening compounds and compositions

Also Published As

Publication number Publication date
DE1908548A1 (en) 1970-11-05
FR2002888A1 (en) 1969-10-31

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