GB1093673A - Novel chromone carboxylic acids - Google Patents

Novel chromone carboxylic acids

Info

Publication number
GB1093673A
GB1093673A GB38068/63A GB3806863A GB1093673A GB 1093673 A GB1093673 A GB 1093673A GB 38068/63 A GB38068/63 A GB 38068/63A GB 3806863 A GB3806863 A GB 3806863A GB 1093673 A GB1093673 A GB 1093673A
Authority
GB
United Kingdom
Prior art keywords
formula
alkyl group
acid
group
substituted
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
GB38068/63A
Inventor
Colin Fitzmaurice
Hugh Cairns
Richard Hazard
John King
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.)
BENGER LAB Ltd
Original Assignee
BENGER LAB 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 BENGER LAB Ltd filed Critical BENGER LAB Ltd
Priority to GB38068/63A priority Critical patent/GB1093673A/en
Priority to DE19641493675 priority patent/DE1493675A1/en
Priority to CH1250064A priority patent/CH453383A/en
Priority to CH313967A priority patent/CH457497A/en
Priority to SE1153564A priority patent/SE335861B/xx
Priority to NL646411222A priority patent/NL140730B/en
Priority to CH313867A priority patent/CH457496A/en
Priority to CH314067A priority patent/CH444882A/en
Priority to BE653617A priority patent/BE653617A/xx
Priority to FR989491A priority patent/FR1462180A/en
Priority to FR989490A priority patent/FR3996M/fr
Priority to IT2073464A priority patent/IT1056701B/en
Priority to US610212A priority patent/US3427324A/en
Publication of GB1093673A publication Critical patent/GB1093673A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Novel compounds of Formula I <FORM:1093673/C2/1> and salts, esters and amides thereof, i.e. the salts, esters and amides of any carboxylic acid function present, and the esters of any hydroxylic function present, in which R is an alkyl group substituted by one or more hydroxyl groups or a carboxyl group, an alkyl group interrupted by one or more oxygen atoms which group may be substituted by one or more hydroxyl groups, an aralkyl group wherein the alkyl group is interrupted by one or more oxygen atoms and may be substituted by one or more hydroxyl groups, an aryloxyalkyl group wherein the alkyl group may be interrupted by one or more oxygen atoms and/or substituted by one or more hydroxyl groups, a heterocyclic ring containing carbon and oxygen which ring may be substituted by one or more hydroxyl groups or by one or more alkyl groups, or an alkyl group substituted by a heterocyclic ring containing carbon and oxygen which ring may be substituted by one or more alkyl groups; R1, R2 and R3 are the same or different and each is a hydrogen or halogen atom, a C1- 12 alkyl group, an alkoxy group, or a group -OR, or R1 and R2 together with the adjacent carbon atoms form a saturated or unsaturated oxygen containing heterocyclic ring; and R5 is a hydrogen atom or an alkyl group, are prepared (1) by cyclizing by heating an a ,g -diketo ester of Formula II <FORM:1093673/C2/2> in which R' is a lower alkyl group, and R" is a hydrogen atom or lower alkyl group, and, if desired, hydrolysing the ester, if formed, to the free acid, (2) by reacting a substituted acetophenone of Formula III <FORM:1093673/C2/3> (a) with an equimolar amount of an ester of formula R1-O-C(X)2-COOR1, where R1 is a lower alkyl group and X is halogen, in the presence of a finely divided metal catalyst of the platinum group of metals, or (b) with an ester of formula X-CO-COOR1 at an elevated temperature and in the presence of an acid binding agent, (3) by dehydrogenating the corresponding chromanone-2-carboxylic acid, (4) by reacting acetylene dicarboxylic acid with a phenol of Formula IV <FORM:1093673/C2/4> (a) in which M is hydrogen, in the presence of an excess of polyphosphoric acid, or (b) in which M is an alkali metal and cyclizing the product formed, or (5) by reacting a 5-hydroxychromone of Formula I in which R represents a hydrogen atom with a compound of formula RX in which R is as defined above and X is a halogen atom, in an inert solvent in the presence of an acid binding agent, or with a compound of Formula <FORM:1093673/C2/5> in which R4 together with the adjacent carbon atoms and the resultant hydroxy group on the carbon atom adjacent to R4 has one of the meanings defined for R in which R contains one or more hydroxyl groups. The chromone-2-carboxylic acids may also be prepared by oxidation of the corresponding 2-aldehydo, 2-methyl, 2-halomethyl, 2-hydroxymethyl or 2-styryl chromones or by hydrolysis of the corresponding 2-cyano-chromones. Sodium 4 - (2 - ethoxyethoxy) - 9 - methoxy - 5 - oxo - 5H - furo - [3,2 - g][l]benzopyran - 7 - carboxylate is obtained by reacting 4-hydroxy-9-methoxy - 7 - methyl - 5 - oxo - 5H - furo-[3,2-g][l]benzopyran with 2-ethoxyethyl bromide, treating the 4-(2-ethoxyethoxy)-9-methoxy - 7 - methyl - 5 - oxo - 5H - furo[3,2-g][l]-benzopyran obtained with potassium carbonate and acetic acid, and reacting the 5-acetyl-4-(2-ethoxyethoxy) - 6 - hydroxy - 7 - methoxybenzo[b]-furan thus formed with diethyl oxalate to give the free acid which may be converted to the ethyl ester and/or the sodium salt. a ,g -Diketo esters of Formula II are prepared by condensing a dialkyl oxalate with an acetophenone in the presence of a condensation catalyst, or by condensing a pyruvate ester of formula R5CH2-CO-COOR1 with a benzoic acid ester of Formula VI. <FORM:1093673/C2/6> Acetophenones of Formula III may be prepared by etherification of compounds in which R is hydrogen. 3,5 - Dichloro - 2,6 - dihydroxy - 4-methylacetophenone is made by treating 2,6-dihydroxy - 4 - methylacetophenone with sulphuryl chloride. 2,6-Dihydroxypropiophenone is obtained by esterifying 4-methyl-7-hydroxycoumarin with propionyl chloride, treating the 4-methyl-7-propionoxycoumarin obtained with aluminium chloride, and treating the 4-methyl-7-hydroxy-8-propionylcoumarin with sodium hydroxide. 2 - Acetyl - 3 - hydroxyphenoxyacetic acid is prepared by treating 2,6-dihydroxyacetophenone with chloracetic acid. Therapeutic compositions, which have activity as inhibitors of the antigen-antibody reaction, and which may be administered orally, topically or parenterally, contain as active ingredient a compound of Formula I above.
GB38068/63A 1963-09-27 1963-09-27 Novel chromone carboxylic acids Expired GB1093673A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
GB38068/63A GB1093673A (en) 1963-09-27 1963-09-27 Novel chromone carboxylic acids
DE19641493675 DE1493675A1 (en) 1963-09-27 1964-09-22 Process for the production of new chromone derivatives
CH1250064A CH453383A (en) 1963-09-27 1964-09-25 Process for the preparation of new chromone derivatives
CH313967A CH457497A (en) 1963-09-27 1964-09-25 Process for the preparation of new chromone derivatives
SE1153564A SE335861B (en) 1963-09-27 1964-09-25
NL646411222A NL140730B (en) 1963-09-27 1964-09-25 PROCESS FOR THE PREPARATION OF SUBSTITUTED CHROMONCABONIC ACID-2-DERIVATIVES WITH AN ANAPHYLACTIC REACTION INHIBITION.
CH313867A CH457496A (en) 1963-09-27 1964-09-25 Process for the preparation of new chromone derivatives
CH314067A CH444882A (en) 1963-09-27 1964-09-25 Process for the preparation of new chromone derivatives
BE653617A BE653617A (en) 1963-09-27 1964-09-25
FR989491A FR1462180A (en) 1963-09-27 1964-09-26 Process for the preparation of new chromone derivatives
FR989490A FR3996M (en) 1963-09-27 1964-09-26
IT2073464A IT1056701B (en) 1963-09-27 1964-09-26 PROCEDURE FOR PREPARING OROMON 2 CARBOXYLIC ACIDS AND THEIR DERIVATIVES
US610212A US3427324A (en) 1963-09-27 1967-01-16 Derivatives of chromone-2-carboxylic acid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB38068/63A GB1093673A (en) 1963-09-27 1963-09-27 Novel chromone carboxylic acids
GB2519264 1964-06-18

Publications (1)

Publication Number Publication Date
GB1093673A true GB1093673A (en) 1967-12-06

Family

ID=26257554

Family Applications (1)

Application Number Title Priority Date Filing Date
GB38068/63A Expired GB1093673A (en) 1963-09-27 1963-09-27 Novel chromone carboxylic acids

Country Status (7)

Country Link
BE (1) BE653617A (en)
CH (4) CH457497A (en)
DE (1) DE1493675A1 (en)
FR (1) FR3996M (en)
GB (1) GB1093673A (en)
IT (1) IT1056701B (en)
SE (1) SE335861B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0017578A1 (en) * 1979-04-06 1980-10-15 Sanofi S.A. 5-(2-Hydroxy-3-thiopropoxy)-chromon-2-carboxylic acids, their salts and esters, process for their preparation and medicines

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4474788A (en) * 1981-11-12 1984-10-02 Fisons Plc Anti-SRSA quinoline carboxylic acid derivatives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0017578A1 (en) * 1979-04-06 1980-10-15 Sanofi S.A. 5-(2-Hydroxy-3-thiopropoxy)-chromon-2-carboxylic acids, their salts and esters, process for their preparation and medicines
FR2453170A1 (en) * 1979-04-06 1980-10-31 Clin Midy 5- (2-HYDROXY-3-THIOPROPOXY) CHROMONE-2-CARBOXYLIC ACIDS AND THEIR APPLICATIONS AS MEDICAMENTS HAVING ANTIANAPHYLACTIC AND ANTIALLERGIC PROPERTIES IN PARTICULAR
US4282247A (en) * 1979-04-06 1981-08-04 Cm Industries 5-(2-Hydroxy-3-thiopropoxy) chromone-2-carboxylic acids chemical process and pharmaceutical compositions

Also Published As

Publication number Publication date
IT1056701B (en) 1982-02-20
BE653617A (en) 1965-03-25
DE1493675A1 (en) 1969-10-23
CH457497A (en) 1968-06-15
CH444882A (en) 1967-10-15
SE335861B (en) 1971-06-14
CH457496A (en) 1968-06-15
CH453383A (en) 1968-06-14
FR3996M (en) 1966-03-14

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