FR2447914A1 - 2:Phenyl 3:substd. benzothiophene deriv(s). - are hypocholesterolaemic cpds. and hypolipidaemics, prepd. from a 3:thiophenone or thione and a halide - Google Patents

2:Phenyl 3:substd. benzothiophene deriv(s). - are hypocholesterolaemic cpds. and hypolipidaemics, prepd. from a 3:thiophenone or thione and a halide

Info

Publication number
FR2447914A1
FR2447914A1 FR7902897A FR7902897A FR2447914A1 FR 2447914 A1 FR2447914 A1 FR 2447914A1 FR 7902897 A FR7902897 A FR 7902897A FR 7902897 A FR7902897 A FR 7902897A FR 2447914 A1 FR2447914 A1 FR 2447914A1
Authority
FR
France
Prior art keywords
phenyl
benzo
hypolipidaemics
hypocholesterolaemic
thiophenone
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.)
Granted
Application number
FR7902897A
Other languages
French (fr)
Other versions
FR2447914B1 (en
Inventor
Fritz Sauter
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.)
Sanofi SA
Original Assignee
Sanofi SA
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 Sanofi SA filed Critical Sanofi SA
Priority to FR7902897A priority Critical patent/FR2447914A1/en
Publication of FR2447914A1 publication Critical patent/FR2447914A1/en
Application granted granted Critical
Publication of FR2447914B1 publication Critical patent/FR2447914B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/64—Oxygen atoms

Landscapes

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

Abstract

2-Phenyl benzo b thiophenes of formula (I) are new- (where X = O or S; R1 = lower alkyl, aralkyl, alkoxyalkyl, alkanoylalkyl, carboxyalkyl or carbalkoxyalkyl; R2 = H, halogen or alkoxy, R3 = H or NO2). Pref. R1 is phenylalkyl, R3 is Cl or Br and X is O. The toxicity is for (I; R1X = methoxy; R2=R3=H), LD50/24H. = 10.9g/kg. p.o. (mouse) and 1.2g kg. i.p. (mouse). (I) may be given orally, rectallyl or parenterally at a daily dosage of 0.05-1.5g. Specifically claimed are e.g. benzylthio-3-phenyl-2-benzo(b) thiophene and ethoxycarbonylmethoxy-3-phenyl-2-benzo(b)thiophene. In an example of prepn., 10g. (II; X = O, R2=R3=H) was mixed with 10 ml. methanol, 10ml. 33% NaOH and 0.08g. Na dithionate, followed by the dropwise addn. over 20 mins. of 8.4ml. dimethyl sulphate. The mixt. was refluxed for 1 hr., cooled and extracted into ether to give 8.2g. (I; R1X = CH3O; R2=R3=H) m.pt. 52-54 degrees C.
FR7902897A 1979-02-05 1979-02-05 2:Phenyl 3:substd. benzothiophene deriv(s). - are hypocholesterolaemic cpds. and hypolipidaemics, prepd. from a 3:thiophenone or thione and a halide Granted FR2447914A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7902897A FR2447914A1 (en) 1979-02-05 1979-02-05 2:Phenyl 3:substd. benzothiophene deriv(s). - are hypocholesterolaemic cpds. and hypolipidaemics, prepd. from a 3:thiophenone or thione and a halide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7902897A FR2447914A1 (en) 1979-02-05 1979-02-05 2:Phenyl 3:substd. benzothiophene deriv(s). - are hypocholesterolaemic cpds. and hypolipidaemics, prepd. from a 3:thiophenone or thione and a halide

Publications (2)

Publication Number Publication Date
FR2447914A1 true FR2447914A1 (en) 1980-08-29
FR2447914B1 FR2447914B1 (en) 1982-02-05

Family

ID=9221608

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7902897A Granted FR2447914A1 (en) 1979-02-05 1979-02-05 2:Phenyl 3:substd. benzothiophene deriv(s). - are hypocholesterolaemic cpds. and hypolipidaemics, prepd. from a 3:thiophenone or thione and a halide

Country Status (1)

Country Link
FR (1) FR2447914A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0177927A1 (en) * 1984-10-09 1986-04-16 Merck & Co. Inc. 3-Hydroxybenzo[b]thiophene-2-sulfide derivatives as specific-5-lipoxygenase inhibitors
EP0729956A1 (en) * 1995-02-28 1996-09-04 Eli Lilly And Company Benzothiophene compounds, intermediates, compositions, and methods
US8642786B2 (en) 2008-02-29 2014-02-04 Nissan Chemical Industries, Ltd. Process for producing thiophene compound and intermediate thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1182785A (en) * 1956-09-17 1959-06-29 Thiophene dioxide compounds
FR4098M (en) * 1963-12-07 1966-04-18
US3597448A (en) * 1967-05-02 1971-08-03 Pfizer 2-arylbenzo(b) thiophen - 3(2h) - one - 1,1 - dioxides and 2 - arylnaphtho(2,3-b)thiophen-3(2h)-one-1,1-dioxides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1182785A (en) * 1956-09-17 1959-06-29 Thiophene dioxide compounds
FR4098M (en) * 1963-12-07 1966-04-18
US3597448A (en) * 1967-05-02 1971-08-03 Pfizer 2-arylbenzo(b) thiophen - 3(2h) - one - 1,1 - dioxides and 2 - arylnaphtho(2,3-b)thiophen-3(2h)-one-1,1-dioxides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0177927A1 (en) * 1984-10-09 1986-04-16 Merck & Co. Inc. 3-Hydroxybenzo[b]thiophene-2-sulfide derivatives as specific-5-lipoxygenase inhibitors
EP0729956A1 (en) * 1995-02-28 1996-09-04 Eli Lilly And Company Benzothiophene compounds, intermediates, compositions, and methods
EP1113013A1 (en) * 1995-02-28 2001-07-04 Eli Lilly & Company Benzothiophene compounds, intermediates, compositions and methods
US8642786B2 (en) 2008-02-29 2014-02-04 Nissan Chemical Industries, Ltd. Process for producing thiophene compound and intermediate thereof
JP5440490B2 (en) * 2008-02-29 2014-03-12 日産化学工業株式会社 Method for producing thiophene compound and intermediate thereof

Also Published As

Publication number Publication date
FR2447914B1 (en) 1982-02-05

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