GB1207771A - Anti-virally active quinoline derivatives - Google Patents

Anti-virally active quinoline derivatives

Info

Publication number
GB1207771A
GB1207771A GB1345269A GB1345269A GB1207771A GB 1207771 A GB1207771 A GB 1207771A GB 1345269 A GB1345269 A GB 1345269A GB 1345269 A GB1345269 A GB 1345269A GB 1207771 A GB1207771 A GB 1207771A
Authority
GB
United Kingdom
Prior art keywords
compounds
aryl
alkyl
halogen
signifies
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
GB1345269A
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 GB1207771A publication Critical patent/GB1207771A/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
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • 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
    • C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by 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
    • C07D215/18—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
    • C07D215/20—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
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Abstract

1,207,771. Quinoline derivatives. WARNERLAMBERT PHARMACEUTICAL CO. 14 March, 1969 [18 March, 1968], No. 13452/69. Heading C2C. Novel compounds I wherein R 1 signifies H, halogen, hydroxy, mercapto, alkylthio or alkoxy, R 2 signifies CHO, CN, CO 2 H carbalkoxy, CONHR 5 or CON(R 5 ) 2 (R 5 is alkyl, aryl, aralkyl or aminoalkyl), R 3 signifies one or more H, halogen, OH, alkyl, aryl, alkoxy, mercapto, CN, CO 2 H, alkylene-dioxy or heterocyclic rings, and R 4 is H, alkyl or aryl (the term aryl includes unsubstituted and substituted monohomo- and monohetero-cyclic rings; the compounds ethyl 4,7 - dichloro-, n - propyl 4 - chloro-, n - hexyl 4,7 - dichloro- and ethyl 4 - chloro - 2 - quinoline carboxylates are excluded), are obtained by the interaction of an amine, R 3 .C 6 (H 4 .- NH 2 , and a keto ester, C.H.R 4 (.COR 2 )(.COOR 6 ) wherein R, is alkyl or aryl, under cyclization conditions to give compounds I wherein R 1 is hydroxy; cyclization in the presence of a phosphorus oxyhalide affords compounds I wherein R 1 is halogen and treatment of compounds I wherein R 1 is hydroxy with a phosphorus oxyhalide also affords such compounds; the halogen atom can be replaced by hydrogen, alkoxy or mercapto by standard methods. Pharmaceutical preparations showing antiviral action contain as active ingredient compounds I; administration may be orally or parenterally.
GB1345269A 1968-03-18 1969-03-14 Anti-virally active quinoline derivatives Expired GB1207771A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US71403368A 1968-03-18 1968-03-18

Publications (1)

Publication Number Publication Date
GB1207771A true GB1207771A (en) 1970-10-07

Family

ID=24868523

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1345269A Expired GB1207771A (en) 1968-03-18 1969-03-14 Anti-virally active quinoline derivatives

Country Status (3)

Country Link
DE (1) DE1913466A1 (en)
FR (1) FR2004175A1 (en)
GB (1) GB1207771A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0303387A1 (en) * 1987-08-12 1989-02-15 Merck Sharp & Dohme Ltd. Kynurenic acid derivatives useful in the treatment of neurodegenerative disorders
US4963566A (en) * 1986-03-28 1990-10-16 Otsuka Pharmaceutical Co., Ltd. Benzimidazolyl-sulfinyl-tetrahydroquinolines
WO1992004328A1 (en) * 1990-09-07 1992-03-19 Schering Corporation Antiviral compounds and antihypertensive compounds
US5270309A (en) * 1987-08-12 1993-12-14 Merck Sharp & Dohme Limited Kynurenic acid derivatives useful in the treatment of neurodegenerative disorders
US5565408A (en) * 1990-05-03 1996-10-15 Basf Aktiengesellschaft Cyanoquinoline compounds
WO2009041521A1 (en) * 2007-09-26 2009-04-02 Astellas Pharma Inc. Quinolone derivative
WO2010128345A1 (en) * 2009-05-05 2010-11-11 Szegedi Tudományegyetem Kynurenic acid analogues, pharmaceutical compositions containing same and use of said compounds for the treatment of headache
CN112624970A (en) * 2019-09-24 2021-04-09 南开大学 Application of 8-bit aryl substituted quinoline nitrogen oxide in plant virus resistance and sterilization

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3704322A (en) * 1969-09-24 1972-11-28 Malesci S A S Inst Farmacobiol N-alkyl-n'-(1-naphthoyl) ethylene diamines
GB1334705A (en) * 1970-06-19 1973-10-24 Ici Ltd Pharmaceutical compositions containing kynurenic acid derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB627297A (en) * 1945-06-04 1949-08-05 Charles Coale Price Method for the preparation of heterocyclic compounds
US3046278A (en) * 1960-10-24 1962-07-24 Rohm & Haas Process of cyanation

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4963566A (en) * 1986-03-28 1990-10-16 Otsuka Pharmaceutical Co., Ltd. Benzimidazolyl-sulfinyl-tetrahydroquinolines
EP0303387A1 (en) * 1987-08-12 1989-02-15 Merck Sharp & Dohme Ltd. Kynurenic acid derivatives useful in the treatment of neurodegenerative disorders
US5270309A (en) * 1987-08-12 1993-12-14 Merck Sharp & Dohme Limited Kynurenic acid derivatives useful in the treatment of neurodegenerative disorders
US5565408A (en) * 1990-05-03 1996-10-15 Basf Aktiengesellschaft Cyanoquinoline compounds
WO1992004328A1 (en) * 1990-09-07 1992-03-19 Schering Corporation Antiviral compounds and antihypertensive compounds
US5378694A (en) * 1990-09-07 1995-01-03 Schering Corporation Acyl and alkoxy substituted quinolines
WO2009041521A1 (en) * 2007-09-26 2009-04-02 Astellas Pharma Inc. Quinolone derivative
US8367702B2 (en) 2007-09-26 2013-02-05 Astellas Pharma Inc. Quinolone derivative
JP5564947B2 (en) * 2007-09-26 2014-08-06 アステラス製薬株式会社 Quinolone derivatives
WO2010128345A1 (en) * 2009-05-05 2010-11-11 Szegedi Tudományegyetem Kynurenic acid analogues, pharmaceutical compositions containing same and use of said compounds for the treatment of headache
CN112624970A (en) * 2019-09-24 2021-04-09 南开大学 Application of 8-bit aryl substituted quinoline nitrogen oxide in plant virus resistance and sterilization

Also Published As

Publication number Publication date
FR2004175A1 (en) 1969-11-21
DE1913466A1 (en) 1969-11-06

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees