DK200001556A - Substituerede thiazolidindionderivater - Google Patents

Substituerede thiazolidindionderivater Download PDF

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Publication number
DK200001556A
DK200001556A DK200001556A DKPA200001556A DK200001556A DK 200001556 A DK200001556 A DK 200001556A DK 200001556 A DK200001556 A DK 200001556A DK PA200001556 A DKPA200001556 A DK PA200001556A DK 200001556 A DK200001556 A DK 200001556A
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thiazolidinedione
methyl
ethoxy
amino
group
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DK200001556A
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Hindley Richard Mark
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Beecham Group Plc
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Priority claimed from GB878720825A external-priority patent/GB8720825D0/en
Priority claimed from GB878727987A external-priority patent/GB8727987D0/en
Priority claimed from GB888802454A external-priority patent/GB8802454D0/en
Application filed by Beecham Group Plc filed Critical Beecham Group Plc
Publication of DK200001556A publication Critical patent/DK200001556A/da

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    • 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
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • 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
    • 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
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C07D277/82—Nitrogen atoms
    • 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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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Peptides Or Proteins (AREA)
  • Steroid Compounds (AREA)

Description

PATENTKRAV 1. Forbindelse med formlen (I):
Figure DK200001556AD00031
eller en tautomer form deraf, og/eller et farmaceutisk acceptabelt salt deraf, og/eller et farmaceutisk acceptabelt solvat deraf, kendetegnet ved, at betegner en substitueret eller usubstitueret aromatisk hetero-cyclylgruppe; r! betegner et hydrogenatom, en alkylgruppe, en acylgruppe, en aral-kylgruppe, hvor arylgruppen kan være substitueret eller usubstitueret, eller en substitueret eller usubstitueret arylgruppe; og betegner hver hydrogen, eller R^ og R^ betegner tilsammen en binding; A^ betegner en benzenring med i alt op til 5 substituenter; og n betegner et helt tal i området fra 2 til 6. 1
Forbindelse ifølge krav 1, kendetegnet ved, at A^ betegner en substitueret eller usubstitueret, enkelt- eller kondenseretring aromatisk heterocyclyl-gruppe omfattende op til A heteroatomer i ringen valgt blandt oxygen, svovl og nitrogen, fx betegner A1 en gruppe med formlen (a), (b) eller (c):
Figure DK200001556AD00032
hvor: R4 og R1 hver uafhængigt af hinanden betegner et hydrogenatom, en alkylgruppe eller en substitueret eller usubstitueret arylgruppe, fx en substitueret eller usubstitueret phenylgruppe, eller, når R^ og hver er bundet til et carbonatom, danner R^ og R^ sammen med de carbonatomer, hvortil de er bundet, en benzenring, hvor hvert carbonatom, der er betegnet ved R^ og R^, sammen kan være substitueret eller usubstitueret, fx betegner R^ og R-> sammen en gruppe med formlen (d):
Figure DK200001556AD00041
(d) hvor R® og R^ hver uafhængigt af hinanden betegner hydrogen, halogen, substitueret eller usubstitueret alkyl eller alkoxy, fx betegner R® og R^ begge hydrogen; og i gruppen med formlen (a) betegner X oxygen eller svovl. 3. Forbindelse ifølge krav 1 eller 2, kendetegnet ved, at betegner en gruppe med formlen (e) :
Figure DK200001556AD00042
(e) hvor R® og R^ hver uafhængigt af hinanden betegner hydrogen, halogen, substitueret eller usubstitueret alkyl eller alkoxy, fx en forbindelse, hvor R® og R^ hver betegner hydrogen. 64 4. Forbindelse ifølge krav 1, med formlen (II):
Figure DK200001556AD00051
eller en tautomer form deraf og/eller et farmaceutisk acceptabelt salt deraf og/eller et farmaceutisk acceptabelt solvat deraf, kendetegnet ved, at A*, R*-, R^, R^ og n er som defineret i forbindelse med formlen (I) i krav 1, og R® og er som defineret i forbindelse med formlen (e) i krav 3. 5. Forbindelse ifølge et hvilket som helst af kravene 1 til 4, kendetegnet ved, at n betegner et helt tal 2 eller 3, og/eller at R* betegner en methylgruppe. 6. Forbindelse ifølge krav 1, valgt fra listen bestående af: 5-(4-(2-(N-methyl-N-(2-benzothiazolyl)amino)ethoxy]benzyl)-2,4-thia-zolidindion; 5-(4-[2-(N-methyl-N-(2-benzothiazolyl)amino)ethoxy]benzyliden) -2 ,4-thiazolidindion; 5-(4-[2-(N-methyl-N-(2-benzoxazolyl)amino)ethoxy]benzyl)-2,4-thiazo-lidindion; 5-(4-[2-(N-me thyl - N - ( 2 -benzoxazo ly 1) amino ) e thoxy ] benzyl iden) -2,4-thiazolidindion; 1 (4- [2- (N-methyl-N- (2-pyrimidinyl)amino)ethoxy]benzyl) -2,4-thiazoli-dindion; 5-(4-[2-(N-methyl-N-(2-pyrimidinyl)amino)ethoxy]benzyliden)-2,4- thiazolidindion; 5-(4-(2-(N-methyl-N-[2-(4,5-dimethylthiazolyl)]amino)ethoxy]benzyl) - 2.4- thiazolidindion; 5-(4-[2-(N-methyl-N-[2-(4,5-dimethylthiazolyl)]amino)ethoxy]benzyli-den)-2,4-thiazolidindion; 5-(4-(2-(N-methyl-N-(2-thiazolyl)amino) ethoxy]benzyl)-2,4-thiazolidindion; 5-(4-[2-(N-methyl-N-(2-thiazolyl)amino)ethoxy]benzyliden)-2,4-thiazolidindion; 5-[4-(2-(N-methyl-N-(2-(4-phenylthiazolyl))amino)ethoxy)benzyl]-2,4-thiazolidindion; 5-(4-[2-(N-methyl-N-(2-(4-phenylthiazolyl))amino)ethoxy]benzyliden)- 2.4- thiazolidindion; 5-(4-(2-(N-methyl-N-[2-(4-phenyl-5-methylthiazolyl)]amino)ethoxy]benzyl) -2,4-thiazolidindion; 5-(4-[2-(N-methyl-N-(2-(4-phenyl-5-methylthiazolyl)]amino)ethoxy]ben -zyliden)-2,4-thiazolidindion; 5-(4-[2-(N-methyl-N-[2-(4-methyl-5-phenylthiazolyl)]amino)ethoxy]ben-zyl)-2,4-thiazolidindion; 5- (4-[2-(N-methyl-N-[2-(4-methyl-5-phenylthiazolyl)]amino)ethoxy]ben-zyliden)-2,4-thiazolidindion; 5-(4-[2-(N-methyl-N-[2-(4-methylthiazolyl)]amino)ethoxy]benzyl)-2,4-thiazolidindion; 5-(4-[2-(N-methyl-N-[2-(4-methylthiazolyl)]amino)ethoxy]benzyl iden)- 2.4- thlazol tdlnd-J on : 5-[4-(2-(N-methyl-N-[2-(5-phenyloxazolyl)]amino)ethoxy)benzyl]-2,4- thiazolidlndion; 5-(4-[2-(N-methyl-N-[2-(5-phenyloxazolyl)]amino)ethoxy]benzyliden)- 2.4- thlazolidindlon; 5-(4-[2-(N-methyl-N-[2-(4,5-dimethyloxazolyl)]amino)ethoxy]benzyl)- 2.4- thiazolidindion; 5-(4-[2-(N-methyl-N-[2-(4,5-dimethyloxazolyl)]amino)ethoxy]benzyli-den)-2,4-thiazolidindion; 5-[4-(2-(2-pyrimidinylamino)ethoxy)benzyl]-2,4-thiazolidindion; 5-[4-(2-(2-pyrimidinylamino)ethoxy)benzyliden]-2,4-thiazolidindion; 5-(4-[2-(N-acetyl-N-(2-pyrimidinyl)amino)ethoxy]benzyl)-2,4-thiazolidindion; 5-(4-(2-(N-(2-benzothiazolyl)-N-benzylamino)ethoxy)benzyliden)-2,4-thiazolidindion; 5-(4-(2-(N-(2-benzothiazolyl)-N-benzylamino)ethoxy)benzyl)-2,4-thiazolidindion; 5-(4-[3-(N-methyl-N-(2-benzoxazolyl)amino)propoxy]benzyl)-2,4-thiazolidindion; 5-(4-(3-(N-methyl-N-(2-benzoxazolyl)amino)propoxy]benzyliden)-2,4-thiazolidindion; 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidin-dion; og 5-(4-(2-(N-methyl-N-(2-pyridyl)amino)ethoxyjbenzyliden)-2,4-thiazolidindion; eller en tautomer form deraf, og/eller et farmaceutisk acceptabelt salt deraf, og/eller et farmaceutisk acceptabelt solvat deraf. 7. Fremgangsmåde til fremstilling af en forbindelse med formlen (I), eller en tautomer form deraf, og/eller et farmaceutisk acceptabelt salt deraf, og/eller et farmaceutisk acceptabelt solvat deraf, kendetegnet ved, at enten (a) en forbindelse med formlen (III)
Figure DK200001556AD00081
(III) hvor R^, og er som defineret i forbindelse med formlen (I), og Ra er en gruppe, der kan omdannes til en gruppe med formlen (f):
Figure DK200001556AD00082
(f) hvor R*·, A*· og n er som defineret i forbindelse med formlen (I), omsættes med et egnet reagens, der er i stand til at omdanne Ra til gruppen (f); eller (b) en forbindelse med formlen (VIII):
Figure DK200001556AD00083
(VIII) hvor R^, A^, A^ og n er som defineret i forbindelse med formel (I), omsættes med 2,4-thiazolidindion; og derefter, om nødvendigt, at ét eller flere af følgende eventuelle trin udføres: (i) en forbindelse med formlen (I) omdannes til en anden forbindelse med formlen (I); (ii) et farmaceutisk acceptabelt salt af forbindelsen med formlen (1) og/eller et farmaceutisk acceptabelt solvat deraf fremstilles. 8. Farmaceutisk præparat, kendetegnet ved, at det omfatter en forbindelse med formlen (I) ifølge krav 1, eller en tautomer form deraf, eller et farmaceutisk acceptabelt salt deraf eller farmaceutisk acceptabelt solvat deraf, og en farmaceutisk acceptabel bærer dertil. 9. Forbindelse med formlen (I) ifølge krav 1, eller en tautomer form deraf, og/eller et farmaceutisk acceptabelt salt deraf, og/eller et farmaceutisk acceptabelt solvat deraf, kendetegnet ved, at den anvendes som en aktiv terapeutisk bestanddel, fx til behandling af og/eller profylakse af hyperglykæmi og/eller hyperlipidæini. 10. Anvendelse af en forbindelse med formlen (I) ifølge krav 1, eller en tautomer form deraf, og/eller et farmaceutisk acceptabelt salt deraf, og/eller et farmaceutisk acceptabelt solvat deraf til fremstilling af et medikament til behandling og/eller profylakse af hyperglykæmi og/eller hyperlipidæmi.
DK200001556A 1987-09-04 2000-10-18 Substituerede thiazolidindionderivater DK200001556A (da)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB878720825A GB8720825D0 (en) 1987-09-04 1987-09-04 Compounds
GB878727987A GB8727987D0 (en) 1987-11-30 1987-11-30 Novel compounds
GB888802454A GB8802454D0 (en) 1988-02-04 1988-02-04 Compounds

Publications (1)

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DK200001556A true DK200001556A (da) 2000-10-18

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Family Applications (2)

Application Number Title Priority Date Filing Date
DK198804902A DK175176B1 (da) 1987-09-04 1988-09-02 Forbindelsen 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidindion, et farmaceutisk præparat indeholdende forbindelsen, forbindelsen som en aktiv terapeutisk bestanddel og anvendelsen af forbindelsen til fremstilling af et medikament
DK200001556A DK200001556A (da) 1987-09-04 2000-10-18 Substituerede thiazolidindionderivater

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DK198804902A DK175176B1 (da) 1987-09-04 1988-09-02 Forbindelsen 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)-2,4-thiazolidindion, et farmaceutisk præparat indeholdende forbindelsen, forbindelsen som en aktiv terapeutisk bestanddel og anvendelsen af forbindelsen til fremstilling af et medikament

Country Status (19)

Country Link
US (1) US5002953A (da)
EP (2) EP0842925A1 (da)
JP (6) JP2614497B2 (da)
KR (1) KR0164207B1 (da)
AT (1) ATE186724T1 (da)
AU (1) AU611938B2 (da)
CA (1) CA1328452C (da)
CZ (1) CZ391691A3 (da)
DE (2) DE3856378T2 (da)
DK (2) DK175176B1 (da)
ES (1) ES2137915T3 (da)
GR (1) GR3031873T3 (da)
HK (1) HK1011029A1 (da)
IE (1) IE20000683A1 (da)
LU (1) LU90711I2 (da)
NL (1) NL300034I2 (da)
NZ (1) NZ226027A (da)
PT (1) PT88410B (da)
SG (1) SG59988A1 (da)

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JP2614497B2 (ja) 1997-05-28
US5002953A (en) 1991-03-26
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DE10199003I2 (da) 2003-09-18
KR890005095A (ko) 1989-05-11
JPH10194970A (ja) 1998-07-28
NZ226027A (en) 1992-03-26
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DK490288D0 (da) 1988-09-02
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LU90711I2 (fr) 2001-03-05
ATE186724T1 (de) 1999-12-15
DK175176B1 (da) 2004-06-21
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CZ391691A3 (en) 1993-03-17
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DE3856378T2 (de) 2000-05-11
DK490288A (da) 1989-03-05
NL300034I2 (nl) 2001-05-01
PT88410B (pt) 1992-10-30
JPH09183726A (ja) 1997-07-15
JP2837139B2 (ja) 1998-12-14
AU611938B2 (en) 1991-06-27
JPH09183771A (ja) 1997-07-15
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JPH10194971A (ja) 1998-07-28
DE10199003I1 (de) 2003-06-12
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EP0842925A1 (en) 1998-05-20
AU2173888A (en) 1989-03-09
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CA1328452C (en) 1994-04-12
PT88410A (pt) 1989-07-31

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