JPS5052070A - - Google Patents

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JPS5052070A
JPS5052070A JP49064605A JP6460574A JPS5052070A JP S5052070 A JPS5052070 A JP S5052070A JP 49064605 A JP49064605 A JP 49064605A JP 6460574 A JP6460574 A JP 6460574A JP S5052070 A JPS5052070 A JP S5052070A
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    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

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.
JP49064605A 1973-06-08 1974-06-08 Pending JPS5052070A (en)

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
JPS5052070A true JPS5052070A (en) 1975-05-09

Family

ID=10258654

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Application Number Title Priority Date Filing Date
JP49064605A Pending JPS5052070A (en) 1973-06-08 1974-06-08

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 (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55147272A (en) * 1979-04-10 1980-11-17 Hoffmann La Roche Novel flavone derivative
JPS62215581A (en) * 1986-03-18 1987-09-22 Koichi Shiyudo Flavone carboxylic acid derivative

Families Citing this family (8)

* 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
NZ193316A (en) * 1979-04-10 1984-07-31 Hoffmann La Roche 3-alkoxyflavone derivatives and pharmaceutical compositions
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.
US5539112A (en) * 1992-02-14 1996-07-23 Kyowa Hakko Kogyo Co., Ltd. 5-aminoflavone derivatives
CA2601028C (en) * 2005-03-11 2014-05-27 Howard Florey Institute Of Experimental Physiology And Medecine Flavonoid compounds and uses 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

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55147272A (en) * 1979-04-10 1980-11-17 Hoffmann La Roche Novel flavone derivative
JPH0118049B2 (en) * 1979-04-10 1989-04-03 Efu Hofuman Ra Roshu Unto Co Ag
JPS62215581A (en) * 1986-03-18 1987-09-22 Koichi Shiyudo Flavone carboxylic acid derivative
JPH0255430B2 (en) * 1986-03-18 1990-11-27 Koichi Shudo

Also Published As

Publication number Publication date
ZA743438B (en) 1975-07-30
NL7407648A (en) 1974-12-10
FR2232310B1 (en) 1978-07-28
FR2232310A1 (en) 1975-01-03
AU6977274A (en) 1975-12-04
GB1461777A (en) 1977-01-19
DK300874A (en) 1975-02-03
NO742077L (en) 1975-01-06
SE7407545L (en) 1974-12-09
DE2427597A1 (en) 1975-04-30
IL44960A0 (en) 1974-09-10
BE815896A (en) 1974-12-04
FI175774A (en) 1974-12-09
ES427083A1 (en) 1976-09-01

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