GB734143A - 3-substituted-4-hydroxycoumarin compounds - Google Patents

3-substituted-4-hydroxycoumarin compounds

Info

Publication number
GB734143A
GB734143A GB6350/53A GB635053A GB734143A GB 734143 A GB734143 A GB 734143A GB 6350/53 A GB6350/53 A GB 6350/53A GB 635053 A GB635053 A GB 635053A GB 734143 A GB734143 A GB 734143A
Authority
GB
United Kingdom
Prior art keywords
hydroxycoumarin
furan
ethyl
general formula
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
GB6350/53A
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.)
WERNER SPIESS
Aurubis AG
Original Assignee
WERNER SPIESS
Norddeutsche Affinerie 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 WERNER SPIESS, Norddeutsche Affinerie AG filed Critical WERNER SPIESS
Publication of GB734143A publication Critical patent/GB734143A/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
    • C07D407/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
    • C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
    • C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring
    • C07D311/48—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring with two such benzopyran radicals linked together by a carbon chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises 3-substituted-4-hydroxycoumarins of the general formula <FORM:0734143/IV (b)/1> and salts of such derivatives, where R is an alkyl group containing not more than 4 carbon atoms or a phenyl group. They are made by reacting 4-hydroxycoumarin with a ketone of the general formula <FORM:0734143/IV (b)/2> suitably by melting together, or refluxing together in an inert diluent, equimolecular proportions of the reactants, preferably in the presence of a salt-forming basic material, as described in Specification 734,142. In examples there are prepared 3-[11-(a -furan)-21-acetyl]-ethyl - 4 - hydroxycoumarin; 3 - [11 - (a - furan)-21 - benzoyl] - ethyl - 4 - hydroxycoumarin and 3 - [11 - (a - furan) - 21 - propionyl] - ethyl - 4 - hydroxycoumarin and their salts.ALSO:A rodenticidal composition comprises an intimate mixture of a 3-substituted-4-hydroxycoumarin of the general formula <FORM:0734143/VI/1> or a salt thereof, in which R is an alkyl group containing not more than 4 carbon atoms or a phenyl group, together with an edible bait or carrier. In an example, 3-(11-[a -furan]-21-acetyl)-ethyl-4-hydroxycoumarin is mixed with talc or chalk to produce a sprinkling powder which adheres to the skin of rodents and is subsequently licked off by them; or this mixture may be incorporated in an edible material such as oatmeal or potatoes. The sodium salt of the compound may also be dissolved in drinking water. The corresponding propionyl and benzoyl compounds are referred to. The compounds of the general formula are incorporated in pharmaceutical compositions effective in retarding the coagulation of the blood of warm-blooded animals.
GB6350/53A 1952-03-08 1953-03-06 3-substituted-4-hydroxycoumarin compounds Expired GB734143A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DES27561A DE947164C (en) 1952-03-08 1952-03-08 Process for the preparation of 4-oxycoumarins substituted in the 3-position

Publications (1)

Publication Number Publication Date
GB734143A true GB734143A (en) 1955-07-27

Family

ID=7479138

Family Applications (2)

Application Number Title Priority Date Filing Date
GB6349/53A Expired GB734142A (en) 1952-03-08 1953-03-06 Process of producing 3-substituted-4-hydroxycoumarins
GB6350/53A Expired GB734143A (en) 1952-03-08 1953-03-06 3-substituted-4-hydroxycoumarin compounds

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB6349/53A Expired GB734142A (en) 1952-03-08 1953-03-06 Process of producing 3-substituted-4-hydroxycoumarins

Country Status (5)

Country Link
CH (1) CH316026A (en)
DE (1) DE947164C (en)
FR (1) FR1070465A (en)
GB (2) GB734142A (en)
NL (1) NL80964C (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2872457A (en) * 1956-04-19 1959-02-03 Wisconsin Alumni Res Found Process for the preparation of 4-hydroxycoumarin derivatives
FR2355499A1 (en) * 1976-06-25 1978-01-20 Rhone Poulenc Ind NEW ISOINDOLINE DERIVATIVE, ITS PREPARATION AND THE COMPOSITIONS CONTAINING IT
IL108459A0 (en) * 1993-02-05 1994-04-12 Opjohn Company 4-Hydroxy-benzopyran-2-ones and 4-hydroxy-cycloalkyl [B] pyran-2-ones useful for treating infections due to hiv and other retroviruses
IL129871A (en) 1994-05-06 2003-11-23 Pharmacia & Upjohn Inc Process for preparing 4-phenyl-substituted octanoyl-oxazolidin-2-one intermediates that are useful for preparing pyran-2-ones useful for treating retroviral infections

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2427578A (en) * 1945-04-02 1947-09-16 Wisconsin Alumni Res Found 3-substituted 4-hydroxycoumarin and process of making it
NL80178C (en) * 1950-01-31

Also Published As

Publication number Publication date
FR1070465A (en) 1954-07-27
NL80964C (en)
DE947164C (en) 1956-08-09
CH316026A (en) 1956-09-15
GB734142A (en) 1955-07-27

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