FR2377384A1 - NEW COMPOUND 2-AMINO-AA-DICYANOACETOPHENONE AND 2-AMINO 3-CYANO-4 HYDROXYQUINOLEINE, THEIR PREPARATION AND THEIR APPLICATION TO THE PREPARATION OF 2-AMINO-4-HYDROXYQUINOLEINS - Google Patents

NEW COMPOUND 2-AMINO-AA-DICYANOACETOPHENONE AND 2-AMINO 3-CYANO-4 HYDROXYQUINOLEINE, THEIR PREPARATION AND THEIR APPLICATION TO THE PREPARATION OF 2-AMINO-4-HYDROXYQUINOLEINS

Info

Publication number
FR2377384A1
FR2377384A1 FR7800960A FR7800960A FR2377384A1 FR 2377384 A1 FR2377384 A1 FR 2377384A1 FR 7800960 A FR7800960 A FR 7800960A FR 7800960 A FR7800960 A FR 7800960A FR 2377384 A1 FR2377384 A1 FR 2377384A1
Authority
FR
France
Prior art keywords
amino
preparation
hydroxyquinolines
cyano
hydroxyquinoleins
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.)
Granted
Application number
FR7800960A
Other languages
French (fr)
Other versions
FR2377384B1 (en
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.)
Pfizer Inc
Original Assignee
Pfizer 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
Application filed by Pfizer Inc filed Critical Pfizer Inc
Publication of FR2377384A1 publication Critical patent/FR2377384A1/en
Application granted granted Critical
Publication of FR2377384B1 publication Critical patent/FR2377384B1/fr
Granted 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles
    • 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
    • C07D215/48Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56Carbon 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Quinoline Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne la préparation de 2-amino-4-hydroxyquinoléines. Le procédé consiste à faire réagir des anhydrides isatoïques avec le malononitrile dans un solvant inerte en présence d'une base pour produire des 2-amino-3-cyano-4-hydroxyquinoléines et des 2-amino- alpha , alpha -dicyanoacétophénones qui sont ensuite hydrolysées et décarboxylées dans des conditions acides ou basiques pour produire des 2-amino-4-hydroxyquinoléines. Les 2-amino-4-hydroxyquinoléines obtenues par le procédé de l'invention sont des composés intermédiaires pour la préparation d'acides 1-oxo- 1H-6-alkoxypyrimidoØl,2-alquinoleine-2- carboxyliques et de leurs esters, qui sont doués de propriétés anti-allergiques.The invention relates to the preparation of 2-amino-4-hydroxyquinolines. The process involves reacting isatoid anhydrides with malononitrile in an inert solvent in the presence of a base to produce 2-amino-3-cyano-4-hydroxyquinolines and 2-amino-alpha, alpha-dicyanoacetophenones which are then hydrolyzed and decarboxylated under acidic or basic conditions to produce 2-amino-4-hydroxyquinolines. The 2-amino-4-hydroxyquinolines obtained by the process of the invention are intermediate compounds for the preparation of 1-oxo-1H-6-alkoxypyrimidoØl, 2-alquinoleine-2-carboxylic acids and their esters, which are endowed with anti-allergic properties.

FR7800960A 1977-01-14 1978-01-13 NEW COMPOUND 2-AMINO-AA-DICYANOACETOPHENONE AND 2-AMINO 3-CYANO-4 HYDROXYQUINOLEINE, THEIR PREPARATION AND THEIR APPLICATION TO THE PREPARATION OF 2-AMINO-4-HYDROXYQUINOLEINS Granted FR2377384A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US75929577A 1977-01-14 1977-01-14

Publications (2)

Publication Number Publication Date
FR2377384A1 true FR2377384A1 (en) 1978-08-11
FR2377384B1 FR2377384B1 (en) 1982-08-06

Family

ID=25055125

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7800960A Granted FR2377384A1 (en) 1977-01-14 1978-01-13 NEW COMPOUND 2-AMINO-AA-DICYANOACETOPHENONE AND 2-AMINO 3-CYANO-4 HYDROXYQUINOLEINE, THEIR PREPARATION AND THEIR APPLICATION TO THE PREPARATION OF 2-AMINO-4-HYDROXYQUINOLEINS

Country Status (10)

Country Link
JP (1) JPS5390271A (en)
BE (1) BE862883A (en)
DE (1) DE2801248C3 (en)
DK (1) DK15478A (en)
FR (1) FR2377384A1 (en)
GB (1) GB1567875A (en)
IE (1) IE46298B1 (en)
IT (1) IT1091846B (en)
LU (1) LU78866A1 (en)
NL (1) NL7800433A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2018301681B2 (en) * 2017-07-14 2022-07-14 Innate Tumor Immunity, Inc. NLRP3 modulators

Also Published As

Publication number Publication date
JPS5625231B2 (en) 1981-06-11
JPS5390271A (en) 1978-08-08
DE2801248B2 (en) 1979-03-15
LU78866A1 (en) 1979-09-06
IE46298B1 (en) 1983-04-20
IT1091846B (en) 1985-07-06
IT7819261A0 (en) 1978-01-13
NL7800433A (en) 1978-07-18
GB1567875A (en) 1980-05-21
DK15478A (en) 1978-07-15
BE862883A (en) 1978-07-13
DE2801248A1 (en) 1978-07-20
IE780071L (en) 1978-07-14
FR2377384B1 (en) 1982-08-06
DE2801248C3 (en) 1979-10-31

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