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GB1296753A - - Google Patents

Info

Publication number
GB1296753A
GB1296753A GB1296753DA GB1296753A GB 1296753 A GB1296753 A GB 1296753A GB 1296753D A GB1296753D A GB 1296753DA GB 1296753 A GB1296753 A GB 1296753A
Authority
GB
United Kingdom
Prior art keywords
methylenedioxy
vinyl
compounds
group
oxocinnoline
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
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 filed Critical
Publication of GB1296753A publication Critical patent/GB1296753A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
    • C07D317/66—Nitrogen atoms not forming part of a nitro radical

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1296753 6,7 - Methylenedioxy - oxocinnoline- 3-carboxylic acids ELI LILLY & CO 2 Feb 1970 [4,Feb 1969 29 Dec 1969] 4817/70 Heading C2C Novel 6,7 - methylenedioxy - oxocinnoline-3- carboxylic acids having the structure: where R is methyl, ethyl, n-propyl, isopropyl, n-butyl, vinyl or allyl and the cationic salts thereof formed with an alkali metal, an alkaline earth metal, ammonia or amines having a pKa greater than 7À5 may be prepared by a six or seven step synthesis from 21-nitro-4<SP>1</SP>,5<SP>1</SP>-methylenedioxyacetophenone in which (1) the nitro group is reduced to amino, (2) the amino group is diazotized and cyclized to yield 6,7-methylenedioxy cinnoline-4-ol, (3) substitution of bromine at the 3 position, (4) conversion of bromo to cyano, (5) alkylating at the 1 position to yield II in which R is as above excepting vinyl, but in addition is #-hydroxy ethyl followed by, (6) hydrolysis of the cyano group to give I and optionally when R is vinyl, (7) dehydration of the #-hydroxyethyl group substituted in step 5 above. The novel compounds II are the subject of Divisional Application 17320/72. Pharmaceutical compositions of the compounds I with the usual excipients show microbial activity when administered orally or parenterally. The compounds may also be used as the active ingredient for antimicrobial activity in agricultural formulations.
GB1296753D 1969-02-04 1970-02-02 Expired GB1296753A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US79654669A 1969-02-04 1969-02-04
US88888069A 1969-12-29 1969-12-29
DE19702005104 DE2005104C2 (en) 1969-02-04 1970-02-04 1-Alkyl-6,7-methylenedioxy-4 (1H) -oxocinnoline-3-carboxylic acids and process for their preparation

Publications (1)

Publication Number Publication Date
GB1296753A true GB1296753A (en) 1972-11-15

Family

ID=27182389

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1296754D Expired GB1296754A (en) 1969-02-04 1970-02-02
GB1296753D Expired GB1296753A (en) 1969-02-04 1970-02-02

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB1296754D Expired GB1296754A (en) 1969-02-04 1970-02-02

Country Status (10)

Country Link
AT (2) AT301541B (en)
BE (1) BE745383A (en)
CA (1) CA968354A (en)
CH (1) CH536854A (en)
CY (2) CY779A (en)
DE (2) DE2065719C2 (en)
DK (1) DK154084C (en)
FR (1) FR2034519B1 (en)
GB (2) GB1296754A (en)
NL (1) NL147145B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1203952B (en) * 1987-04-23 1989-02-23 Ind Chimica Profarmaco Spa PROCESS FOR THE PREPARATION OF 1-ALCHIL-3-CABOSSI-4-CINNOLONI
GB9813776D0 (en) * 1998-06-25 1998-08-26 Smithkline Beecham Plc Novel compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1076828A (en) * 1963-12-12 1967-07-26 Warner Lambert Pharmaceutical Methylenedioxy quinoline derivatives

Also Published As

Publication number Publication date
DK154084C (en) 1989-02-27
NL147145B (en) 1975-09-15
DE2005104A1 (en) 1970-08-06
DE2005104C2 (en) 1984-09-06
AT301541B (en) 1972-09-11
CA968354A (en) 1975-05-27
DK154084B (en) 1988-10-10
CY778A (en) 1975-03-01
CH536854A (en) 1973-05-15
DE2065719A1 (en) 1975-03-20
AT308747B (en) 1973-07-25
BE745383A (en) 1970-08-03
GB1296754A (en) 1972-11-15
CY779A (en) 1975-03-01
FR2034519A1 (en) 1970-12-11
NL7001317A (en) 1970-08-06
DE2065719C2 (en) 1986-04-24
FR2034519B1 (en) 1974-03-22

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PE20 Patent expired after termination of 20 years