FI81097B - Foerfarande foer framstaellning av nya terapeutiskt verksamma tiazolidindionderivat. - Google Patents

Foerfarande foer framstaellning av nya terapeutiskt verksamma tiazolidindionderivat. Download PDF

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Publication number
FI81097B
FI81097B FI853796A FI853796A FI81097B FI 81097 B FI81097 B FI 81097B FI 853796 A FI853796 A FI 853796A FI 853796 A FI853796 A FI 853796A FI 81097 B FI81097 B FI 81097B
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FI
Finland
Prior art keywords
compound
methyl
general formula
oxazolyl
phenyl
Prior art date
Application number
FI853796A
Other languages
English (en)
Finnish (fi)
Other versions
FI81097C (sv
FI853796A0 (fi
FI853796L (fi
Inventor
Kanji Meguro
Takeshi Fujita
Original Assignee
Takeda Chemical Industries Ltd
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
Priority claimed from PCT/JP1984/000466 external-priority patent/WO1986002073A1/ja
Priority claimed from PCT/JP1985/000179 external-priority patent/WO1986006069A1/ja
Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Publication of FI853796A0 publication Critical patent/FI853796A0/fi
Publication of FI853796L publication Critical patent/FI853796L/fi
Application granted granted Critical
Publication of FI81097B publication Critical patent/FI81097B/fi
Publication of FI81097C publication Critical patent/FI81097C/sv

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D277/34—Oxygen atoms
    • 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
    • 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
    • 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
    • C07D417/14—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 three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Liquid Developers In Electrophotography (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Saccharide Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (4)

1. Förfarande för framställning av en terapeutiskt verksam förening, vars allmänna formel är: QL 1 -CH-C-C - O Il II s. .NH (!) R' X^R* g där R1 är väte eller Ci-C^-alkyl eller fenyl, som valbart kan vara substituerad med en eller tvä Ci-C^-alkoxigrupper, en Ci-C^-alkyl-, halogen-, Ci-C4-alkyltio-, hydroxyl- eller tri-fluormetylgrupp; eller R1 är en cyklohexyl- eller cyklohexen-ylgrupp, som kan vara substituerad i 1-position med en metyl-grupp; eller Rl kan vara bensyl, pyridyl, furyl eller tienyl; R2 är väte eller en Ci-C^-alkylgrupp, som kan vara substituerad med en hydroxylgrupp; X är en syre- eller svavelatom; Z är hydroxylerad metylen eller en karbonylgrupp; m är 0 eller 1; n är 1, 2 eller 3; L och M betecknar oberoende en väteatom eller L och M kan förenas med varandra för att bilda en bindning, eller salter av dylika föreningar, kännetecknat därav, att a) en förening med den allmänna formeln (II) där Y är halogen och de övriga symbolerna betecknar samma som ovan, bringas att reagera med en förening med den allmänna formeln (III) /=\ i* ? Ηθ-d ^-CH-C-C-0 s. .Äh l (III) 60 81 097 där L och M betecknar samma som ovan, eller ett sait av en dylik förening, varefter om sä önskas reaktionsprodukten redu-ceras; eller b) en förening med den allmänna formeln (1-2) ΛQ L I -CH-C-C-0 I I Il sv ,nh K' X^R* C (1-2) O där alla symbolerna betecknar samma som ovan, eller ett sait av en dylik förening reduceras; eller c) en förening med den allmänna formeln (1-3) °H /=\ i Ϊ N . /t H-(CH,).-0-^)>-CH-C-C - O ,iX vNH <*-» R1 X/XR* V där alla symbolerna betecknar samma som ovan, eller ett sait av en dylik förening oxideras; eller d) en förening med den allmänna formeln (IV) N_-C - O li k F'-'W jr <1V> NH där alla symbolerna betecknar samma som ovan, eller ett sait av en dylik förening hydrolyseras; eller e) en förening med den allmänna formeln (V) ii 61 81097 liHi/<z,"~<CH’,’'0~<^~CHO <v> r,Ax/\ri där alia symbolerna betecknar samma som ovan, bringas att reagera med en förening med den allmänna formeln (VI) CHj—C - 0 s A" (vi) V· & eller ett salt av en dylik förening; eller f) en förening med den allmänna formeln (1-5) N_/(Z).-(CH*).-0-(v^ Vc«=C-C - O fl A A» R^W I «ϊ-5» där alia symbolerna betecknar samma som ovan, reduceras.
2. Förfarande enligt patentkravet 1, kännetecknat därav, att man framställer föreningen 5-(4-(2-(5-metyl-2-fen-yl-4-oxazolyl)etoxi]bensyliden}-2, 4-tiazolidindion eller dess salt.
3. Förfarande enligt patentkravet 1, kännetecknat därav, att man framställer föreningen 5-{4-[2-(5-metyl-2-fen-yl-4-oxazolyl)-2-hydroxietoxi Jbensyl)-2, 4-tiazolidindion eller dess salt.
4. Förfarande enligt patentkravet 1, kännetecknat därav, att man framställer föreningen 5-{4-[2-(5-metyl-2-fenyl-4-oxazolyl)etoxiJbensyl}-2, 4-tiazolidindion eller dess salt.
FI853796A 1984-10-03 1985-10-01 Förfarande för framställning av nya terapeutiskt verksamma tiazolidind ionderivat FI81097C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP8400466 1984-10-03
PCT/JP1984/000466 WO1986002073A1 (en) 1984-10-03 1984-10-03 Thiazolidinedione derivatives, process for their preparation, and pharmaceutical composition containing same
PCT/JP1985/000179 WO1986006069A1 (en) 1985-04-09 1985-04-09 Thiazolidinedione derivatives, process for their preparation and medicinal composition containing same
JP8500179 1985-04-09

Publications (4)

Publication Number Publication Date
FI853796A0 FI853796A0 (fi) 1985-10-01
FI853796L FI853796L (fi) 1986-04-04
FI81097B true FI81097B (fi) 1990-05-31
FI81097C FI81097C (sv) 1990-09-10

Family

ID=26425066

Family Applications (1)

Application Number Title Priority Date Filing Date
FI853796A FI81097C (sv) 1984-10-03 1985-10-01 Förfarande för framställning av nya terapeutiskt verksamma tiazolidind ionderivat

Country Status (15)

Country Link
US (1) US4725610A (sv)
EP (1) EP0177353B1 (sv)
JP (1) JPS6185372A (sv)
KR (1) KR920002131B1 (sv)
CN (1) CN1003445B (sv)
AT (1) ATE51869T1 (sv)
AU (1) AU583537B2 (sv)
CA (1) CA1263655A (sv)
DE (1) DE3577092D1 (sv)
DK (1) DK444685A (sv)
ES (2) ES8706150A1 (sv)
FI (1) FI81097C (sv)
GR (1) GR852389B (sv)
NO (1) NO157896C (sv)
PT (1) PT81235B (sv)

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KR920002131B1 (ko) 1992-03-12
AU4817685A (en) 1986-04-10
NO853902L (no) 1986-04-04
EP0177353A2 (en) 1986-04-09
NO157896C (no) 1988-06-08
EP0177353B1 (en) 1990-04-11
DE3577092D1 (de) 1990-05-17
ATE51869T1 (de) 1990-04-15
FI81097C (sv) 1990-09-10
US4725610A (en) 1988-02-16
CA1263655A (en) 1989-12-05
JPH0570626B2 (sv) 1993-10-05
EP0177353A3 (en) 1986-12-30
JPS6185372A (ja) 1986-04-30
ES547507A0 (es) 1987-06-01
CN1003445B (zh) 1989-03-01
ES8801256A1 (es) 1987-12-16
KR860003243A (ko) 1986-05-21
DK444685D0 (da) 1985-10-01
NO157896B (no) 1988-02-29
PT81235A (en) 1985-11-01
ES554559A0 (es) 1987-12-16
FI853796A0 (fi) 1985-10-01
ES8706150A1 (es) 1987-06-01
PT81235B (pt) 1987-11-30
FI853796L (fi) 1986-04-04
AU583537B2 (en) 1989-05-04
CN85107870A (zh) 1986-07-16
DK444685A (da) 1986-04-04

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