GB1461777A - 2-phenyl-4-oxo-4h-1-benzopyran derivatives - Google Patents

2-phenyl-4-oxo-4h-1-benzopyran derivatives

Info

Publication number
GB1461777A
GB1461777A GB2737973A GB2737973A GB1461777A GB 1461777 A GB1461777 A GB 1461777A GB 2737973 A GB2737973 A GB 2737973A GB 2737973 A GB2737973 A GB 2737973A GB 1461777 A GB1461777 A GB 1461777A
Authority
GB
United Kingdom
Prior art keywords
formula
compound
group
defined above
prepared
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
GB2737973A
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 GB2737973A priority Critical patent/GB1461777A/en
Priority to ZA00743438A priority patent/ZA743438B/en
Priority to IL44960A priority patent/IL44960A0/en
Priority to DK300874A priority patent/DK300874A/da
Priority to BE145060A priority patent/BE815896A/en
Priority to AU69772/74A priority patent/AU6977274A/en
Priority to FI1757/74A priority patent/FI175774A/fi
Priority to ES427083A priority patent/ES427083A1/en
Priority to NO742077A priority patent/NO742077L/no
Priority to DE19742427597 priority patent/DE2427597A1/en
Priority to FR7419668A priority patent/FR2232310B1/fr
Priority to NL7407648A priority patent/NL7407648A/xx
Priority to SE7407545A priority patent/SE7407545L/xx
Priority to JP49064605A priority patent/JPS5052070A/ja
Publication of GB1461777A publication Critical patent/GB1461777A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
    • C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/43—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/58—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/61—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/20—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
    • 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
    • C07C45/64—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 functional groups containing oxygen only in singly bound form
    • 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D309/22—Radicals substituted by oxygen atoms

Abstract

1461777 2 - Phenyl - 4 - oxo - 4H - 1 benzopyran derivatives FISONS Ltd 28 May 1974 [8 June 1973] 27379/73 Heading C2C Novel compounds of the Formula I in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 which may be the same or different each represent hydrogen, alkyl, alkoxy, halogen, alkenyl, amino, hydroxy, -CF 3 , -CN, alkylamino, alkoxyalkoxy, hydroxyalkoxy, -NO 2 or R 6 and R 7 together form a -(CH 2 ) 4 - or -(CH 2 ) 3 O- chain, and E is a carboxylic acid group, a 1H-tetrazol-5-yl group, a N-(1H- tetrazol-5-yl) carboxamide group, a group -CH 2 COOH, a group -CONHOH, or a group -CO-CHR 2 CO-R 1 , R 1 represents alkyl C 1-6 , alkoxy C 1-6 , phenyl, amino, or mono- or dialkyl C 1-6 amino, R 2 represents hydrogen or -CORx, and Rx represents alkyl C 1-6 , alkoxy C 1-6 , amino or mono- or di-alkyl C 1-6 amino, or R 1 and R 2 together form a 3- or 4-membered alkylene chain which is optionally interrupted by an -NH- group, and which chain is optionally substituted by one or more alkyl C 1-6 groups and/or, on the carbon atom a to the methine proton, by a carbonyl oxygen atom, and pharmaceutically acceptable salts, esters and amides of the group E thereof where E is capable of priming such a derivative, provided that (i) when E is a -COOH group, or a pharmaceutically acceptable salt, ester or amide thereof, and R 3 , R 8 , R 9 , R 10 , R 11 and R 12 are all hydrogen then (A) R 5 is not hydrogen or alkoxy, or (B) R 6 is not hydrogen, hydroxy, alkyl or alkoxy, or (C) R 7 is not hydrogen or alkoxy, or (ii) when E is a -COOH group, or a pharmaceutically acceptable salt, ester or amide thereof, E is not in the 2<SP>1</SP>-position, may be prepared by (a) cyclizing a compound of Formula II in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , E and the provisos are as defined above, with the further proviso that E and either of the groups on adjacent carbon atoms do not form a cyclizable pair of groups, Z is a reactive halogen atom or a group -OM, and M is hydrogen or an alkali metal cation, (b) producing a compound of Formula Ia in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and the provisos are as defined above, by hydrolysing a compound of Formula III in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and the provisos are as defined above, and Ry represents a group which is hydrolysable to a -COOH group, (c) producing a compound of Formula Id in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are as defined above, by reacting a compound of Formula VI in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are as defined above, with an azide in a solvent which is inert under the reaction conditions, (d) producing a compound of Formula Ie in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are as defined above, by reacting an anhydride, ester or acid halide of a compound of Formula Ia, with hydroxylamine, (e) producing a compound of Formula I in which E is a group by (1) reacting an acid halide or a mixed anhydride of a compound of Formula Ia, with a compound of formula CH 2 R 2 COR 1 , or an enamine thereof, and if an enamine is used, hydrolysing the resulting compound, or (ii) hydrolysing a compound of Formula VII in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are as defined above, and Ra and Rb, which may be the same or different, each represent an alkyl C 1-6 group, or together with the nitrogen atom form a 5, 6 or 7 membered heterocyclio ring which optionally contains an oxygen atom, (f) producing a compound of Formula Ih in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are as defined above, by treating a compound of Formula VIII in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are as defined above, with water, (g) producing a compound of Formula I in which R 3 is a halogen atom by selective halogenation of a corresponding compound of Formula I in which R 3 is a hydrogen atom, (h) producing a compound of Formula I in which R 3 is an -OH group by oxidative cyclization of a compound of Formula X in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 ,R 12 , E and M are as defined above, (i) producing a compound of Formula I in which one or more of R 3 to R 12 is an alkoxy group or a hydroxyalkoxy group, subject to the provisos defined above, by reacting a corresponding compound of Formula I in which one or more of R 3 to R 12 is an -OH group, subject to proviso (i) (B) only, with an alkylating agent, or with an alkylene oxide respectively, (j) selectively dehydrogenating a corresponding flavanone compound of Formula XV in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , E and the provisos are as defined above, (k) producing a compound of Formula I in which at least one of R 3 to R 12 is an amino group, by selective reduction of a corresponding compound of Formula I in which at least one of R 3 to R 12 is a -NO 2 group, (1) producing a compound of Formula Il in which R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are as defined above, by reacting an anhydride, ester or acid halide of a compound of Formula Ia, with 5-aminotetrazole, or (m) producing a compound of Formula I in which R 3 to R 12 and the provisos are as defined above, save that one of R 3 to R 12 is an -OH group, by dealkylation of a corresponding compound of Formula I in which R 3 to R 12 are as defined above (but the provisos do not apply except as regards R 6 ), save that one of R 3 to R 12 except R 6 is an alkoxy group and where desired or necessary converting the compound of Formula I to a pharmaceutically acceptable salt, ester or amide of the group E thereof or vice versa. Intermediates of the Formula II are prepared by rearrangement under basic conditions of the corresponding 2 - (E - substituted benzoyloxy)- acetophenone which in turn is produced by acylation of a 2-hydroxy acetophenone, using an E-substituted benzoic acid derivative. Under certain conditions the diketo II is formed directly from the esterification process. Also compounds of the Formula I may be prepared directly from the acetophenone above without isolation of the compound II. Intermediates of the Formula III in which Ry is cyano are prepared (1) from a compound of the Formula II in which E is nitro by cyclization to produce a compound I in which E is nitro followed by reduction of the nitro group to amino followed by diazotization and reaction with copper cyanide or (2) cyclization of a compound of the Formula II in which E is acetamido followed by hydrolysis of this grouping to amino and then diazotization and reaction with copper cyanide. In both preparations the compound of the Formula II is prepared from the corresponding 2-hydroxy acetophenone and an E-substituted benzoic acid derivative as described in the previous paragraph. Intermediates of the Formula VIII are prepared by reacting a compound of the Formula I in which E is -COCl with diazomethane. Intermediates of the Formula X are prepared by reacting 2-hydroxy acetophenone with an E-substituted benzaldehyde. 2-Chloro-6-hydroxyacetophenone is prepared by diazotization of 2-amino-6-chloroacetophenone. 2 - Bromo - 6 - hydroxyaoetophenone is prepared by forming the acid chloride from 2- bromo-6-nitrobenzoic acid followed by reaction of the acid chloride with diethylmalonate/Mg to yield diethyl 2 - bromo - 6 - nitrobenzoylmalonate which is decarboxylated to yield 2-bromo-6- nitroacetophenone which is reduced to 2-amino-6- bromoacetophenone which is diazotized to yield the required compound. 3,4 - Dichloro - 2 - hydroacetophenone and 3,6- dichloro-2-hydroacetophenone are prepared by reacting the appropriate dichlorophenol with dimethyl acetylene-dicarboxylate to yield a dichlorophenoxyfumaric acid (and also the maleic acid) which is cyclized to yield a dichloro-4-oxo- 4H-1-benzopyran-2-carboxylic acid which on hydrolysis yields the required compounds. 4 - Carbomethoxy - 3 - nitrobenzoyl chloride is prepared by partial hydrolysis of dimethyl nitroterephthalate to yield 4-carbomethoxy-3- nitrobenzoic acid followed by formation of the acid chloride. Chloroterephthalic acid is formed as a byproduct from the reaction of 3-chloro-2- hydroxy-acetophenone and 3-chloro-4-carbomethoxy benzoic acid. Pharmaceutical compositions of the compounds I with the usual excipients show bronchodilatory activity and are useful in treatment of other diseases caused by antigen-antibody reactionswhen administered orally or by inhalation.
GB2737973A 1973-06-08 1973-06-08 2-phenyl-4-oxo-4h-1-benzopyran derivatives Expired GB1461777A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
GB2737973A GB1461777A (en) 1973-06-08 1973-06-08 2-phenyl-4-oxo-4h-1-benzopyran derivatives
ZA00743438A ZA743438B (en) 1973-06-08 1974-05-28 Substituted flavones, processes for their preparation and compositions containinh them
IL44960A IL44960A0 (en) 1973-06-08 1974-06-03 Novel benzopyrane derivatives,their preparation and pharmaceutical compositions containing them
DK300874A DK300874A (en) 1973-06-08 1974-06-04
BE145060A BE815896A (en) 1973-06-08 1974-06-04 COMPOUNDS WITH BRONCHODILATOR AND ANTIALLERGIC EFFECT
AU69772/74A AU6977274A (en) 1973-06-08 1974-06-04 Compounds
FI1757/74A FI175774A (en) 1973-06-08 1974-06-07
ES427083A ES427083A1 (en) 1973-06-08 1974-06-07 2-phenyl-4-oxo-4h-1-benzopyran derivatives
NO742077A NO742077L (en) 1973-06-08 1974-06-07
DE19742427597 DE2427597A1 (en) 1973-06-08 1974-06-07 BENZOPYRANE DERIVATIVES, PROCESS FOR THEIR MANUFACTURING AND PHARMACEUTICAL PREPARATIONS CONTAINING THESE
FR7419668A FR2232310B1 (en) 1973-06-08 1974-06-07
NL7407648A NL7407648A (en) 1973-06-08 1974-06-07
SE7407545A SE7407545L (en) 1973-06-08 1974-06-07
JP49064605A JPS5052070A (en) 1973-06-08 1974-06-08

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2737973A GB1461777A (en) 1973-06-08 1973-06-08 2-phenyl-4-oxo-4h-1-benzopyran derivatives

Publications (1)

Publication Number Publication Date
GB1461777A true GB1461777A (en) 1977-01-19

Family

ID=10258654

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2737973A Expired GB1461777A (en) 1973-06-08 1973-06-08 2-phenyl-4-oxo-4h-1-benzopyran derivatives

Country Status (14)

Country Link
JP (1) JPS5052070A (en)
AU (1) AU6977274A (en)
BE (1) BE815896A (en)
DE (1) DE2427597A1 (en)
DK (1) DK300874A (en)
ES (1) ES427083A1 (en)
FI (1) FI175774A (en)
FR (1) FR2232310B1 (en)
GB (1) GB1461777A (en)
IL (1) IL44960A0 (en)
NL (1) NL7407648A (en)
NO (1) NO742077L (en)
SE (1) SE7407545L (en)
ZA (1) ZA743438B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4352792A (en) * 1979-04-10 1982-10-05 Hoffmann-La Roche Inc. 3-Alkoxyflavone antiviral agents
US4831052A (en) * 1986-03-18 1989-05-16 Shionogi & Co., Ltd. Flavone carboxylic acid derivatives
US5539112A (en) * 1992-02-14 1996-07-23 Kyowa Hakko Kogyo Co., Ltd. 5-aminoflavone derivatives
CN102391258A (en) * 2011-09-13 2012-03-28 中山大学 Amino-substituted flavone compound and preparation and use thereof
EP1856085B1 (en) * 2005-03-11 2015-07-08 Howard Florey Institute Pty Ltd Flavonoid compounds and uses thereof
CN111592465A (en) * 2019-02-20 2020-08-28 武汉珈汇精化科技有限公司 Method for preparing 2-amino-4-aminomethyl methyl benzoate and hydrochloride thereof

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4018798A (en) * 1975-11-20 1977-04-19 Warner-Lambert Company Substituted (4-oxo-4H-1-benzopyran-2-yl)cyclopropane carboxylic acids and esters
JPS55147272A (en) * 1979-04-10 1980-11-17 Hoffmann La Roche Novel flavone derivative
FR2543140B1 (en) * 1983-03-24 1985-06-21 Cortial NOVEL FLAVONE-CARBOXYLIC ACIDS-4 ', THEIR PREPARATION METHOD AND THEIR APPLICATION IN THERAPEUTICS
FR2593066B1 (en) * 1986-01-17 1989-06-30 Pasteur Institut THERAPEUTIC COMPOSITIONS BASED ON 3-ALKOXYFLAVON DERIVATIVES AND NEW 3-ALKOXYFLAVON DERIVATIVES.

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4352792A (en) * 1979-04-10 1982-10-05 Hoffmann-La Roche Inc. 3-Alkoxyflavone antiviral agents
US4831052A (en) * 1986-03-18 1989-05-16 Shionogi & Co., Ltd. Flavone carboxylic acid derivatives
US4925979A (en) * 1986-03-18 1990-05-15 Shionogi & Co., Ltd. Flavone carboxylic acid derivatives
US5539112A (en) * 1992-02-14 1996-07-23 Kyowa Hakko Kogyo Co., Ltd. 5-aminoflavone derivatives
EP1856085B1 (en) * 2005-03-11 2015-07-08 Howard Florey Institute Pty Ltd Flavonoid compounds and uses thereof
CN102391258A (en) * 2011-09-13 2012-03-28 中山大学 Amino-substituted flavone compound and preparation and use thereof
CN102391258B (en) * 2011-09-13 2014-09-24 中山大学 Amino-substituted flavone compound and preparation and use thereof
CN111592465A (en) * 2019-02-20 2020-08-28 武汉珈汇精化科技有限公司 Method for preparing 2-amino-4-aminomethyl methyl benzoate and hydrochloride thereof

Also Published As

Publication number Publication date
FR2232310A1 (en) 1975-01-03
JPS5052070A (en) 1975-05-09
FR2232310B1 (en) 1978-07-28
ES427083A1 (en) 1976-09-01
DK300874A (en) 1975-02-03
NO742077L (en) 1975-01-06
DE2427597A1 (en) 1975-04-30
SE7407545L (en) 1974-12-09
BE815896A (en) 1974-12-04
ZA743438B (en) 1975-07-30
IL44960A0 (en) 1974-09-10
FI175774A (en) 1974-12-09
AU6977274A (en) 1975-12-04
NL7407648A (en) 1974-12-10

Similar Documents

Publication Publication Date Title
JP2512751B2 (en) Pharmacologically active 1,5-diaryl-3-substituted-pyrazols and process for their preparation
US4191775A (en) Amide derivatives
CA2467261C (en) Novel benzophenone derivatives or salts thereof
SE7407545L (en)
EA002427B1 (en) Process for making dirylpyridines useful as cox-2 inhibitors
JPS5929185B2 (en) Method for producing phenol derivatives
US2398418A (en) Introduction of organic radicals into quinones
AU574129B2 (en) Arylacetic acid derivatives
US3697552A (en) Anthracyclidine-acetic acid derivatives
Snider et al. Preparation of epoxides by oxidative decarboxylation of. beta.-hydroxy acids. Stereo-and regiochemistry of oxidative elimination of secondary radicals with cupric acetate
US3502660A (en) 2-((5&#39;-(3&#39; and/or 4&#39;-substituted)isoxazoyl) methylidene)-3,4,10-trioxo-1,2,3,4,4a,9,9a,10-octahydroanthracenes
JPS6037099B2 (en) New pyrazole derivatives and their production method
US3699117A (en) 2-((5&#39;-(3&#39;-and/or 4&#39;-substituted) isoxazolyl) aminoethyl) - 3,4,10 - trioxo-1,2,3,4,4,9,9,10-octahydroanthracenes and related compounds
Morrison et al. Conversion of. beta.-hydroxyglutarohydroxamates to carbapenem precursors
AU2003294861B2 (en) Indenoncarboxylic acids derivatives and their use for the treatment of and preventing diabetes and dyslipidaemia
US4260763A (en) Isoquinoline aldehydes
GB1562943A (en) Pyrazole derivatives and their manufacture and use
GB1481161A (en) 5-(substituted-benzoyloxy)pyrazoles and a process for their conversion to 4-benzoyl-pyrazole derivatives
Kende et al. Total synthesis of tetracyclines. IV. Synthesis of an anhydrotetracycline derivative
US4537906A (en) Substituted phenylalkenoic acids and esters
Davis et al. Synthesis and Microbiological Properties of 3-Amino-3, 4-dihydro-1-hydroxycarbostyril1
GB1389227A (en) Chromone-2-carboxylic acid derivatives methods for their preparation and compositions containing them
GB1511169A (en) Trycyclic acetic acid derivatives
US4453005A (en) Process for preparing substituted phenylalkenoic acids
CH634071A5 (en) Therapeutically active pyranoquinolones

Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee