FI92198B - Förfarande för framställning av farmakologiskt värdefulla 2-(RS)-substituerade 2,3-dihydro-5-oxi-4,6,7-trimetylbensofuraner - Google Patents

Förfarande för framställning av farmakologiskt värdefulla 2-(RS)-substituerade 2,3-dihydro-5-oxi-4,6,7-trimetylbensofuraner Download PDF

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Publication number
FI92198B
FI92198B FI903994A FI903994A FI92198B FI 92198 B FI92198 B FI 92198B FI 903994 A FI903994 A FI 903994A FI 903994 A FI903994 A FI 903994A FI 92198 B FI92198 B FI 92198B
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FI
Finland
Prior art keywords
dihydro
preparation
formula
oxy
trimethylbenzofurans
Prior art date
Application number
FI903994A
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English (en)
Finnish (fi)
Other versions
FI903994A0 (sv
FI92198C (sv
Inventor
Mario Brufani
Stefano Ceccarelli
Vellis Patrizia De
Patrizia Giannetti
Agnese Paesano
Romolo Scuri
Sergio Zanarella
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Foscama Biomed Chim Farma
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Application filed by Foscama Biomed Chim Farma filed Critical Foscama Biomed Chim Farma
Publication of FI903994A0 publication Critical patent/FI903994A0/sv
Application granted granted Critical
Publication of FI92198B publication Critical patent/FI92198B/sv
Publication of FI92198C publication Critical patent/FI92198C/sv

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/10—Expectorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/12—Mucolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Toxicology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Biochemistry (AREA)
  • Urology & Nephrology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Fats And Perfumes (AREA)

Claims (2)

1. Förfarande för framställning av farmakologiskt värdefulia 2-(RS)-substituerade 2,3-dihydro-5-oxi-4,6,7-trimetyl- 5 bensofuraner med formeln ch3 RO _
10 JL (I) H3C ^ 0 ^CHjCH^ ch3 varvid i formeln R är 15 - väte eller en hemisuckinoylgrupp R-^ är en sulfhydrylgrupp eller acyltiogrupp, SCOR3, där R3 är lägre alkyl, särskilt metyl, kännetecknat därav, att ett derivat av 2-(RS)- 2,3-dihydro-5-hydroxi-4,6,7-trimetylbensofuranyl) ättiksyra 20 reduceras med nägot känt redudktionsmedel av en karboxyl-funktion, särskilt litium- och aluminiumhydrid, i en lös-ning med ett eterlösningsmedel, säsom tetrahydrofuran, den sä erhällna föreningen behandlas med trifenylfosfin, dialkylazodikarboxylat, och en lämplig tiosyra, R3COSH, i 25 lösning med ett inert lösningsmedel, säsom tetrahydrofuran, : och den sä erhällna föreningen eventuellt: - acyleras med ett aktiverat derivat av en lämplig karbo-xylsyra eller - hydrolyseras genom behandling av tioesterderivatet med en 30 vattenlösning av en lämplig svag bas, säsom utspädd ammo- niak, tili vilken satts ett organiskt lösningsmedel, säsom aceton, i en inert atmosfär. 1 Förfarande enligt patentkravet 1 för framställning av 5- 35 (2,3-dihydro-2-(R,S)-(2-acetyltioetyl)-4,6,7-trimetylbenso furanyl -monoester, kännetecknat därav, att lämpliga utgängsämnen används.
FI903994A 1989-08-18 1990-08-13 Förfarande för framställning av farmakologiskt värdefulla 2-(RS)-substituerade 2,3-dihydro-5-oxi-4,6,7-trimetylbensofuraner FI92198C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2153289 1989-08-18
IT8921532A IT1231341B (it) 1989-08-18 1989-08-18 2,3 diidro 5 ossi 4,6,7 trimetilbenzofurani 2 (rs) sostituiti, utili come farmaci antiossidanti con proprieta' mucoregolatrici e antiischemiche.

Publications (3)

Publication Number Publication Date
FI903994A0 FI903994A0 (sv) 1990-08-13
FI92198B true FI92198B (sv) 1994-06-30
FI92198C FI92198C (sv) 1994-10-10

Family

ID=11183207

Family Applications (1)

Application Number Title Priority Date Filing Date
FI903994A FI92198C (sv) 1989-08-18 1990-08-13 Förfarande för framställning av farmakologiskt värdefulla 2-(RS)-substituerade 2,3-dihydro-5-oxi-4,6,7-trimetylbensofuraner

Country Status (21)

Country Link
US (1) US5114966A (sv)
EP (1) EP0413668B1 (sv)
JP (1) JP2931056B2 (sv)
KR (1) KR0167553B1 (sv)
CN (1) CN1032135C (sv)
AT (1) ATE131164T1 (sv)
AU (1) AU634570B2 (sv)
CA (1) CA2023522A1 (sv)
CS (1) CS277503B6 (sv)
DE (1) DE69023980T2 (sv)
DK (1) DK0413668T3 (sv)
ES (1) ES2080821T3 (sv)
FI (1) FI92198C (sv)
GR (1) GR3019030T3 (sv)
HU (1) HU207059B (sv)
IT (1) IT1231341B (sv)
NO (1) NO175819C (sv)
NZ (1) NZ234934A (sv)
PT (1) PT95037B (sv)
RU (1) RU2068845C1 (sv)
ZA (1) ZA906266B (sv)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0550292A1 (en) * 1992-01-02 1993-07-07 Merrell Dow Pharmaceuticals Inc. Tissue protective tocopherol analogs
EP0560568A3 (en) * 1992-03-13 1994-06-29 Takeda Chemical Industries Ltd Hydroquinone derivatives and intermediates for production thereof
US5721233A (en) * 1992-04-06 1998-02-24 Merrell Pharmaceuticals Inc. Derivatives of 2,3-dihydro benzofuranols
DE69314022T2 (de) * 1992-04-06 1998-02-12 Merrell Pharma Inc Derivate von 2,3-dihydro-2,2,4,6,7-pentaalkyl-5-benzofuranen
US5510373A (en) * 1992-04-06 1996-04-23 Merrell Pharmaceuticals Inc. Cardioprotective agents
US5545660A (en) * 1992-04-07 1996-08-13 Merrell Pharmaceuticals Inc. Hydrazide derivatives of 3,4-dihydro-2H-1-benzopyrans
IT1256264B (it) * 1992-12-31 1995-11-29 Lifegroup Spa N-acilderivati di idrossiammine dotati di attivita' scavenger ed utilizzabili nelle patologie acute e croniche correlate a fenomeni di perossidazione ed infiammazione
WO1995029906A1 (fr) * 1994-04-28 1995-11-09 Meiji Milk Products Co., Ltd. Derive de benzofurane et son utilisation
FR2720395B1 (fr) * 1994-05-31 1996-06-28 Oreal Nouveaux composés de la famille des benzohétérocycles.
US6150402A (en) * 1994-08-15 2000-11-21 Loma Linda University Medical Center Natriuretic compounds
US5798356A (en) * 1995-08-07 1998-08-25 Alcon Laboratories, Inc. Angiostatic compounds
US6048891A (en) 1998-12-17 2000-04-11 Loma Linda University Medical Center Use of γ-tocopherol and its oxidative metabolite LLU-α in the treatment of natriuretic disease
US6653346B1 (en) 2002-02-07 2003-11-25 Galileo Pharmaceuticals, Inc. Cytoprotective benzofuran derivatives
US7078541B2 (en) * 2002-02-07 2006-07-18 Galileo Pharmaceuticals, Inc. Benzofuran derivatives
CN107056707B (zh) * 2017-01-23 2019-08-23 温州医科大学 一种3,4,5-三甲氧基苯类化合物及其在制备抗氧化药物中的应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1281325C (en) * 1984-06-20 1991-03-12 Patrice C. Belanger Benzofuran derivatives
JPS6388173A (ja) * 1986-09-30 1988-04-19 Kuraray Co Ltd ２，３−ジヒドロベンゾフラン誘導体
JP2855341B2 (ja) * 1988-06-10 1999-02-10 武田薬品工業株式会社 新規２―置換クマラン誘導体
JP2855340B2 (ja) * 1988-06-10 1999-02-10 武田薬品工業株式会社 ２―置換クマラン誘導体
IT1229482B (it) * 1988-08-01 1991-09-03 Foscama Biomed Chim Farma Acidi (rs) 2 (2,3 diidro 5 idrossi 4,6,7 trimetilbenzofuranil) acetico e 2 (2,3 diidro 5 acilossi 4,6,7 trimetilbenzofuranil) acetici e loro esteri, utili come farmaci mucoregolatori ed antiischemici.

Also Published As

Publication number Publication date
PT95037A (pt) 1991-04-18
NO175819C (no) 1994-12-14
DK0413668T3 (da) 1996-04-22
DE69023980T2 (de) 1996-08-01
EP0413668A3 (en) 1991-09-11
NO175819B (no) 1994-09-05
CA2023522A1 (en) 1991-02-19
CS277503B6 (en) 1993-03-17
FI903994A0 (sv) 1990-08-13
ZA906266B (en) 1991-05-29
FI92198C (sv) 1994-10-10
RU2068845C1 (ru) 1996-11-10
ATE131164T1 (de) 1995-12-15
AU6128090A (en) 1991-02-21
NO903640D0 (no) 1990-08-17
CS402390A3 (en) 1992-01-15
HU905062D0 (en) 1991-01-28
DE69023980D1 (de) 1996-01-18
US5114966A (en) 1992-05-19
KR910004588A (ko) 1991-03-29
JPH03236383A (ja) 1991-10-22
IT1231341B (it) 1991-11-28
HUT54669A (en) 1991-03-28
HU207059B (en) 1993-03-01
EP0413668A2 (en) 1991-02-20
KR0167553B1 (ko) 1999-01-15
CN1049499A (zh) 1991-02-27
JP2931056B2 (ja) 1999-08-09
NO903640L (no) 1991-02-19
EP0413668B1 (en) 1995-12-06
AU634570B2 (en) 1993-02-25
CN1032135C (zh) 1996-06-26
GR3019030T3 (en) 1996-05-31
NZ234934A (en) 1992-02-25
IT8921532A0 (it) 1989-08-18
ES2080821T3 (es) 1996-02-16
PT95037B (pt) 1997-10-31

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Owner name: BIOMEDICA FOSCAMA INDUSTRIA

BB Publication of examined application
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Owner name: BIOMEDICA FOSCAMA INDUSTRIA