GB1055726A - Basic ethers of 3,4-diarylcoumarins - Google Patents

Basic ethers of 3,4-diarylcoumarins

Info

Publication number
GB1055726A
GB1055726A GB14757/64A GB1475764A GB1055726A GB 1055726 A GB1055726 A GB 1055726A GB 14757/64 A GB14757/64 A GB 14757/64A GB 1475764 A GB1475764 A GB 1475764A GB 1055726 A GB1055726 A GB 1055726A
Authority
GB
United Kingdom
Prior art keywords
phenyl
agents
coumarin
methoxyphenyl
compounds
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
GB14757/64A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB1055726A publication Critical patent/GB1055726A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • 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
    • C07D407/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)

Abstract

The invention comprises compounds of formula <FORM:1055726/C2/1> where R1, R2 and R3 each represents C1- 8 alkyl, C2- 8 alkenyl, CF3, C1- 8 alkoxy, C2- 8 alkenyloxy, C1- 8 alkylenedioxy, halogen, C1- 8 alkylmercapto or <FORM:1055726/C2/2> where A is C2- 6 alkylene, R4 and R5 each represents C1- 8 alkyl or together with the N1 atom complete a 5- to 7-membered saturated heterocyclic ring which may contain a further N or O atom, and x, y and z are each integers from 0 to 4, at least one of R1, R2 and R3 being <FORM:1055726/C2/3> and pharmacologically acceptable acid addition and quaternary ammonium salts. They are prepared by reacting corresponding compounds in which <FORM:1055726/C2/4> is replaced by OH with <FORM:1055726/C2/5> in the presence of an inert solvent and a base, and forming salts as desired. 7 - Acetoxy - 3,4 - diphenylcoumarin, 3-(pmethyloxyphenyl) - 4 - (p - acetoxyphenyl) coumarin, 3 - phenyl - 4 - (p - acetoxyphenyl) coumarin and 7 - acetoxy - 3 - (p - methoxyphenyl) -4-phenyl-coumarin are prepared by reacting an appropriate dihydroxy- or diacetoxy-benzophenone with sodium phenyl acetate or an appropriately substituted derivative in the presence of acetic anhydride, and then hydrolysed to give 3,4-diphenyl-7-hydroxy-, 3-(p-methoxyphenyl) - 4 - (p - hydroxyphenyl)-, 3-phenyl - 4 - (p - hydroxyphenyl)- and 3 - (p - methoxyphenyl) - 4 - phenyl - 7 - hydroxy - coumarin respectively. The compounds of the above formula may be administered orally or parenterally as tablets, powders, capsules, solutions or suspensions as anti-infertility agents, anti-oestrogenic agents, gonadotrophin-inhibiting agents, agents for lowering blood lipid and cholesterol levels, and as anti-inflammatory agents.
GB14757/64A 1963-05-23 1964-04-09 Basic ethers of 3,4-diarylcoumarins Expired GB1055726A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US282568A US3275658A (en) 1963-05-23 1963-05-23 Tertiary-aminoalkoxy-substituted 3, 4-diphenylcoumarins

Publications (1)

Publication Number Publication Date
GB1055726A true GB1055726A (en) 1967-01-18

Family

ID=23082095

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14757/64A Expired GB1055726A (en) 1963-05-23 1964-04-09 Basic ethers of 3,4-diarylcoumarins

Country Status (4)

Country Link
US (1) US3275658A (en)
DE (1) DE1518399A1 (en)
FR (1) FR1561912A (en)
GB (1) GB1055726A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2901336A1 (en) * 1979-01-15 1980-07-24 Boehringer Mannheim Gmbh NEW ARYLETHERS, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS
JPH07110853B2 (en) * 1990-09-07 1995-11-29 シェリング・コーポレーション Antiviral and antihypertensive compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1934361A (en) * 1933-05-02 1933-11-07 Selected Chemicals Inc 7 ethoxy 4 methyl coumarin
DE1102694B (en) * 1960-02-22 1961-03-23 Bayer Ag Optical brighteners

Also Published As

Publication number Publication date
FR1561912A (en) 1969-04-04
US3275658A (en) 1966-09-27
DE1518399A1 (en) 1969-08-07

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