GB1374981A - Process for the production of bis-chromone-2-carboxylic acids and intermediates therefor - Google Patents

Process for the production of bis-chromone-2-carboxylic acids and intermediates therefor

Info

Publication number
GB1374981A
GB1374981A GB292571A GB292571A GB1374981A GB 1374981 A GB1374981 A GB 1374981A GB 292571 A GB292571 A GB 292571A GB 292571 A GB292571 A GB 292571A GB 1374981 A GB1374981 A GB 1374981A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
groups
chromone
carboxylic acids
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
GB292571A
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.)
Fisons Ltd
Original Assignee
Fisons Ltd
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 Fisons Ltd filed Critical Fisons Ltd
Priority to GB292571A priority Critical patent/GB1374981A/en
Priority to CA132,514A priority patent/CA994787A/en
Priority to NL7200727A priority patent/NL7200727A/xx
Priority to SE69672A priority patent/SE383744B/en
Priority to CH94872A priority patent/CH540248A/en
Priority to JP770372A priority patent/JPS5710108B1/ja
Publication of GB1374981A publication Critical patent/GB1374981A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 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 in position 2

Landscapes

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

Abstract

1374981 Chromone-2-carboxylic acids and intermediates FISONS Ltd 3 Jan 1972 [22 Jan 1971 31 March 1971] 2925/71 and 8767/71 Heading C2C Bis-chromone-2-carboxylic acids of Formula I in which R<SP>1</SP> to R<SP>6</SP> are the same or different and each is a hydrogen or halogen atom or an alkyl, hydroxy, alkoxy or substituted alkyl or alkoxy group, and X is a saturated or unsaturated, substituted or unsubstituted hydrocarbon chain which may be interrupted by a carbocyclic or heterocyclic ring, or by one or more oxygen atoms or carbonyl groups, and pharmaceutically acceptable derivatives thereof, are obtained by cyclising a compound of Formula II in which each pair of groups A<SP>1</SP>, A<SP>2</SP> denotes a pair of groups -OH and -COCH 2 COCOOH, or the chain -O-C(COOH)=CH-CO- or a derivative (e.g. ester), thereof, provided that at least one of the pairs of groups A<SP>1</SP>, A<SP>2</SP> represents the pair of groups -OH and and where necessary or desired converting the resulting compound of Formula I to a pharmaceutically acceptable derivative or vice versa. The cyclization may be effected by heating, preferably in the presence of an acid, e.g. HCl, and in an inert solvent, at temperatures from 20‹ to 150‹ C. Compounds (I) are useful in the treatment of allergic asthma. Novel compounds of Formula II may be obtained by reacting together the compounds (III), (IV) and compound (V), A-X<SP>1</SP>-B and reacting the product with diethyl oxalate in manner known per se to form the diethyl ester of (I), and carefully treating this compound, or its hydrolysis product of Formula (I), with dilute NaOH at approximately ambient temperature (A and B in (V) being groups capable of reacting with -OH to form an ether linkage, and X<SP>1</SP> being such that with the residues of A and B it forms an X group). Compound (II) may also be obtained by treating a compound of formula (VIII) in which R is an alkyl group, with alkali under controlled conditions, e.g. by extracting a chloroform solution with aqueous alkali.
GB292571A 1971-01-22 1971-01-22 Process for the production of bis-chromone-2-carboxylic acids and intermediates therefor Expired GB1374981A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB292571A GB1374981A (en) 1971-01-22 1971-01-22 Process for the production of bis-chromone-2-carboxylic acids and intermediates therefor
CA132,514A CA994787A (en) 1971-01-22 1972-01-17 Production of chromone-2-carboxylic acids
NL7200727A NL7200727A (en) 1971-01-22 1972-01-19
SE69672A SE383744B (en) 1971-01-22 1972-01-21 PROCEDURE FOR THE PRODUCTION OF CHROMON-2-CARBONIC ACIDS
CH94872A CH540248A (en) 1971-01-22 1972-01-21 Process for the preparation of substituted chromone-2-carboxylic acids
JP770372A JPS5710108B1 (en) 1971-01-22 1972-01-21

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB292571A GB1374981A (en) 1971-01-22 1971-01-22 Process for the production of bis-chromone-2-carboxylic acids and intermediates therefor
GB876771 1971-03-31

Publications (1)

Publication Number Publication Date
GB1374981A true GB1374981A (en) 1974-11-20

Family

ID=26237854

Family Applications (1)

Application Number Title Priority Date Filing Date
GB292571A Expired GB1374981A (en) 1971-01-22 1971-01-22 Process for the production of bis-chromone-2-carboxylic acids and intermediates therefor

Country Status (6)

Country Link
JP (1) JPS5710108B1 (en)
CA (1) CA994787A (en)
CH (1) CH540248A (en)
GB (1) GB1374981A (en)
NL (1) NL7200727A (en)
SE (1) SE383744B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005063732A1 (en) * 2003-12-23 2005-07-14 Microbia, Inc. Compounds and methods for the treatment of asthma

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59159004U (en) * 1983-04-11 1984-10-25 デイエツクスアンテナ株式会社 antenna element

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4826014A (en) * 1971-08-05 1973-04-05

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005063732A1 (en) * 2003-12-23 2005-07-14 Microbia, Inc. Compounds and methods for the treatment of asthma
US8088935B2 (en) 2003-12-23 2012-01-03 Ironwood Pharmaceuticals, Inc. Compounds and methods for the treatment of asthma

Also Published As

Publication number Publication date
CH540248A (en) 1973-08-15
NL7200727A (en) 1972-07-25
SE383744B (en) 1976-03-29
CA994787A (en) 1976-08-10
JPS5710108B1 (en) 1982-02-24

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Legal Events

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