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GB1087539A - 3,6-disubstituted flavan derivatives and their preparation - Google Patents

3,6-disubstituted flavan derivatives and their preparation

Info

Publication number
GB1087539A
GB1087539A GB43600/66A GB4360066A GB1087539A GB 1087539 A GB1087539 A GB 1087539A GB 43600/66 A GB43600/66 A GB 43600/66A GB 4360066 A GB4360066 A GB 4360066A GB 1087539 A GB1087539 A GB 1087539A
Authority
GB
United Kingdom
Prior art keywords
formula
disubstituted
flavan
general formula
derivative
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
GB43600/66A
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.)
Merck KGaA
Original Assignee
E Merck AG
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 E Merck AG filed Critical E Merck AG
Publication of GB1087539A publication Critical patent/GB1087539A/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
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
    • C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
    • 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
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Novel 3,6-disubstituted flavan derivatives of the formula <FORM:1087539/C2/1> wherein R1 is an alkyl or alkoxy group containing 1 to 6 carbon atoms, R2 is hydrogen, an alkyl group containing 1 to 6 carbon atoms or a -(CH2)n-NR1R11 group, R1 and R11 are methyl or ethyl groups or which, together with the nitrogen atom to which they are joined, constitute a pyrrolidino, piperidino or morpholino group, and n is 2 or 3, the esters of the above compounds wherein R2 is hydrogen and the acid addition salts and quaternary ammonium derivatives of the nitrogen-containing compounds are prepared (a) by reduction of a flavene, flavone, flavanone, flavanol or flavylium salt of the formula <FORM:1087539/C2/2> wherein Y is <FORM:1087539/C2/3> wherein X- is an anion of a strong acid, Z is OH or = O and a protected phenolic hydroxy group may also be present; (b) by cyclising a 2,4-disubstituted phenol of the formula <FORM:1087539/C2/4> wherein W is -CR1 = CH- or -CHR1 = CHX1-, X1 is OH, Cl, Br or I and a protected phenolic hydroxy group may also be present; (c) by cyclising a 4-substituted phenol ether of the formula <FORM:1087539/C2/5> followed in all the said methods by optional saponification of an esterified hydroxy group in a flavan derivative of the first general formula, by optional alkylation or acylation to another flavan derivative of the first general formula or by optional conversion to an acid addition salt or quaternary ammonium compound thereof. The 2,4-disubstituted phenols of the third general formula above are prepared by condensation of a hydroquinone derivative, optionally esterified or etherified, with a compound of the formula X1-CH2-W-C6H6, by reaction of benzaldehyde with a Grignard reagent of the formula <FORM:1087539/C2/6> wherein Hal is chlorine, bromine or iodine, or by reduction of a chalcone of the formula <FORM:1087539/C2/7> Pharmaceutical compositions comprise a flavan derivative of the first general formula above or a physiologically compatible acid addition salt or quaternary ammonium compound thereof as active ingredient in admixture with a pharmaceutical carrier and may be administered enterally, parenterally or topically.
GB43600/66A 1965-10-20 1966-09-29 3,6-disubstituted flavan derivatives and their preparation Expired GB1087539A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEM0067001 1965-10-20

Publications (1)

Publication Number Publication Date
GB1087539A true GB1087539A (en) 1967-10-18

Family

ID=7312020

Family Applications (1)

Application Number Title Priority Date Filing Date
GB43600/66A Expired GB1087539A (en) 1965-10-20 1966-09-29 3,6-disubstituted flavan derivatives and their preparation

Country Status (11)

Country Link
US (1) US3555047A (en)
BE (1) BE688588A (en)
CH (1) CH487141A (en)
DE (1) DE1518038C3 (en)
DK (1) DK116739B (en)
ES (1) ES332458A1 (en)
FR (1) FR7297M (en)
GB (1) GB1087539A (en)
IL (1) IL26629A (en)
NL (1) NL6614645A (en)
SE (1) SE353536B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025599A1 (en) * 1979-09-13 1981-03-25 The Wellcome Foundation Limited Benzopyran compounds, useful as chemotherapeutic agents
EP0652006A1 (en) * 1993-11-05 1995-05-10 Eli Lilly And Company Use of 2-phenyl-3-aryl-dihychobenzopyrans for lowering serum cholesterol

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4148909A (en) * 1974-07-30 1979-04-10 Beecham Group Limited Chromans to treat depression and reduce appetite
WO2003074044A1 (en) * 2002-03-01 2003-09-12 Eli Lilly And Company Substituted benzopyrans as selective estrogen receptor-beta agonists

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025599A1 (en) * 1979-09-13 1981-03-25 The Wellcome Foundation Limited Benzopyran compounds, useful as chemotherapeutic agents
EP0652006A1 (en) * 1993-11-05 1995-05-10 Eli Lilly And Company Use of 2-phenyl-3-aryl-dihychobenzopyrans for lowering serum cholesterol

Also Published As

Publication number Publication date
DE1518038C3 (en) 1975-01-23
BE688588A (en) 1967-04-20
DK116739B (en) 1970-02-09
ES332458A1 (en) 1967-11-01
CH487141A (en) 1970-03-15
FR7297M (en) 1969-11-12
DE1518038A1 (en) 1969-06-26
DE1518038B2 (en) 1974-06-06
IL26629A (en) 1970-08-19
NL6614645A (en) 1967-04-21
US3555047A (en) 1971-01-12
SE353536B (en) 1973-02-05

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