GB1046380A - New hypocholesteremic compositions - Google Patents

New hypocholesteremic compositions

Info

Publication number
GB1046380A
GB1046380A GB22620/65A GB2262065A GB1046380A GB 1046380 A GB1046380 A GB 1046380A GB 22620/65 A GB22620/65 A GB 22620/65A GB 2262065 A GB2262065 A GB 2262065A GB 1046380 A GB1046380 A GB 1046380A
Authority
GB
United Kingdom
Prior art keywords
treating
resulting
bis
prepared
compound
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
GB22620/65A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid 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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB1046380A publication Critical patent/GB1046380A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Novel 3,4 - bis - (31,41 - dimethoxyphenyl) -hex-3-ene is prepared by treating propioveratrone in a benzene-ethanol mixture with aluminium foil and mercuric chloride, treating the resulting pinacol with glucial acetic acid and concentrated sulphuric acid, reducing the resulting pinacolone with sodium borohydride and treating the resulting product with glucial acetic acid and concentrated sulphuric acid. Novel 3,4 - bis - (31,41 -methylenedioxyphenyl)-hex-3-ene is prepared by a similar method from 3,4-methylenedioxypropiophene. Novel 3,4 - bis - (31,41,51 - trimethoxy -phenyl)-n-hexane is prepared by reacting 3,4,5-trimethoxybenzoyl chloride and dimethylamine, treating the resulting N,N-dimethyl-3,4,5-trimethoxybenzamide with ethyl lithium, treating the resulting 3,4,5-trimethoxypropiophenone with hydrazine hydrate, hydrogenating the resulting 3,4,5-trimethoxypropiophenone azine to form 3,31; 4,41; 5,51 - hexamethoxy - a -azopropylbenzene, and heating this compound under nitrogen. 3,31; 4,41 - Tetramethoxy - stilbene is prepared by treating 3,4-dimethoxyphenylacetonitrile with sodium methoxide and ethyl nitrate to form the sodium salt of a -nitro-(3,4-dimethoxyphenyl)-acetonitrile and treating this compound with aqueous sodium hydroxide. 3,4 - bis - (31 - methoxy - 41 -hydroxyphenyl)-n-hexane is prepared by reacting isoeugenol with benzyl chloride in the presence of potassium hydroxide to form isoeugenol benzyl ether, treating this compound with hydrobromic acid and then iron powder to form 3,4-bis-(31-methoxy - 41 benzyloxy - phenyl) - n - hexane and hydrogenating this compound.ALSO:Hypocholesteremic compositions comprise a compound <FORM:1046380/A5-A6/1> wherein C1 - C2 represents -CH2. CH2-, <FORM:1046380/A5-A6/2> are H, OH, or methoxy, R2 is OH, methoxy, or benzyloxy, or R1 and R2 together form a C1-4 alkylenedioxy radical, and a pharmaceutical carrier. The compositions may be administered orally or parenterally.
GB22620/65A 1964-07-06 1965-05-27 New hypocholesteremic compositions Expired GB1046380A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US38065064A 1964-07-06 1964-07-06

Publications (1)

Publication Number Publication Date
GB1046380A true GB1046380A (en) 1966-10-26

Family

ID=23501983

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22620/65A Expired GB1046380A (en) 1964-07-06 1965-05-27 New hypocholesteremic compositions

Country Status (4)

Country Link
BE (1) BE666387A (en)
FR (1) FR4684M (en)
GB (1) GB1046380A (en)
NL (1) NL6507692A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0028305A1 (en) * 1979-09-13 1981-05-13 The Wellcome Foundation Limited Diaryl compounds and pharmaceutical formulations containing them
US4996237A (en) * 1987-01-06 1991-02-26 Arizona Board Of Regents Combretastatin A-4
US5211953A (en) * 1989-07-21 1993-05-18 Suntory, Limited Liver function improver
US5409953A (en) * 1987-01-06 1995-04-25 Arizona Board Of Regents Acting On Behalf Of Arizona State University Isolation, structural elucidation and synthesis of novel antineoplastic substances denominated "combretastatins"
US5589506A (en) * 1993-03-10 1996-12-31 Morinaga Milk Industry Co., Ltd. Stilbene derivative and stilbene analog derivative, and use thereof
US5827898A (en) * 1996-10-07 1998-10-27 Shaman Pharmaceuticals, Inc. Use of bisphenolic compounds to treat type II diabetes

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0028305A1 (en) * 1979-09-13 1981-05-13 The Wellcome Foundation Limited Diaryl compounds and pharmaceutical formulations containing them
US4996237A (en) * 1987-01-06 1991-02-26 Arizona Board Of Regents Combretastatin A-4
US5409953A (en) * 1987-01-06 1995-04-25 Arizona Board Of Regents Acting On Behalf Of Arizona State University Isolation, structural elucidation and synthesis of novel antineoplastic substances denominated "combretastatins"
US5569786A (en) * 1987-01-06 1996-10-29 Arizona Board Of Regents Acting On Behalf Of Arizona State University Isolation, structural elucidation and synthesis of novel antineoplastic substances denominated "combretastatins"
US5211953A (en) * 1989-07-21 1993-05-18 Suntory, Limited Liver function improver
US5589506A (en) * 1993-03-10 1996-12-31 Morinaga Milk Industry Co., Ltd. Stilbene derivative and stilbene analog derivative, and use thereof
US5827898A (en) * 1996-10-07 1998-10-27 Shaman Pharmaceuticals, Inc. Use of bisphenolic compounds to treat type II diabetes

Also Published As

Publication number Publication date
BE666387A (en) 1966-01-05
FR4684M (en) 1966-12-19
NL6507692A (en) 1966-01-07

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