US20060106221A1 - Process for the preparation of thiazolidinedione derivatives - Google Patents
Process for the preparation of thiazolidinedione derivatives Download PDFInfo
- Publication number
- US20060106221A1 US20060106221A1 US11/326,003 US32600306A US2006106221A1 US 20060106221 A1 US20060106221 A1 US 20060106221A1 US 32600306 A US32600306 A US 32600306A US 2006106221 A1 US2006106221 A1 US 2006106221A1
- Authority
- US
- United States
- Prior art keywords
- process according
- thiazolidinedione
- pharmaceutically acceptable
- pyridyl
- catalyst
- 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.)
- Abandoned
Links
- 0 C.CCC1SC(=O)NC1=O.[1*]N(C)COC Chemical compound C.CCC1SC(=O)NC1=O.[1*]N(C)COC 0.000 description 5
- VEVXPYMQKPSSCN-UHFFFAOYSA-N C.CC([Rb])C1(C)SC(=O)NC1=O.COCN(C)[RaH] Chemical compound C.CC([Rb])C1(C)SC(=O)NC1=O.COCN(C)[RaH] VEVXPYMQKPSSCN-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N CC1=CC=C(C)C=C1 Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Definitions
- This invention relates to a novel process and in particular to a process for preparing certain substituted thiazolidinedione derivatives.
- European Patent Application, Publication Number 0306228 discloses certain thiazolidinedione derivatives of formula (A): or a tautomeric form thereof or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof, wherein: A a represents a substituted or unsubstituted aromatic heterocyclyl group; R a represents a hydrogen atom, an alkyl group, an acyl group, an aralkyl group, wherein the aryl moiety may be substituted or unsubstituted, or a substituted or unsubstituted aryl group; R b and R c each represent hydrogen or R b and R c together represent a bond; A b represents a benzene ring having in total up to five substituents; and n′ represents an integer in the range of from 2 to 6.
- EP 0306228 also discloses a process for reducing the compounds of formula (A) wherein R b and R c together represent a bond (the ‘benzylidene thiazolidine-2,4-diones’) to the corresponding compounds of formula (A) wherein R b and R c each represent hydrogen (the ‘benzylthiazolidine-2,4-diones’).
- the particular reduction methods disclosed in EP 0306228 are dissolving metal methods and catalytic hydrogenation methods.
- the present invention provides a process for preparing a compound of formula (I): or a tautomeric form thereof or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof, wherein: A 1 represents a substituted or unsubstituted aromatic heterocyclyl group; R 1 represents a hydrogen atom, an alkyl group, an acyl group, an aralkyl group, wherein the aryl moiety may be substituted or unsubstituted, or a substituted or unsubstituted aryl group; A 2 represents a benzene ring having in total up to five substituents; and n represents an integer in the range of from 2 to 6, which process comprises catalytically reducing a compound of formula (II): wherein A 1 , R 1 , A 2 and n are as defined in relation to formula (I), characterised in that the reduction reaction is carried out using a hydrogen pressure above 20 psi, and thereafter, if required, forming a pharmaceutically
- the reaction is carried out at a pressure in the range of from 50 to 1500 psi, such as 60 to 1500 psi, 75 to 1500 psi, 200 to 1500 psi, 70 to 1000 psi or 200 to 1000 psi, suitably 70 to 1000 psi.
- reaction pressures include 70, 75, 80, 500 and 1000 psi.
- a suitable hydrogenation catalyst is a noble metal catalyst, suitably a palladium catalyst.
- Favoured catalysts are supported noble metal catalysts, such as a palladium-on-carbon catalyst, typically comprising 5% to 10% of palladium.
- a preferred catalyst is a 10% palladium-on-carbon catalyst.
- Catalyst loadings (expressed as w/w % of catalyst to substrate) in the reaction are typically in the range of from 5 to 100%, usually 10 to 50% and preferably 25 to 50%.
- the reaction may be carried out using any suitable solvent such as acetic acid, or an alkanol, such as methanol or ethanol, preferably admixed with an aqueous mineral acid such as hydrochloric acid; or tetrahydrofuran, preferably admixed with an aqueous mineral acid such as hydrochloric acid.
- acetic acid or an alkanol, such as methanol or ethanol, preferably admixed with an aqueous mineral acid such as hydrochloric acid; or tetrahydrofuran, preferably admixed with an aqueous mineral acid such as hydrochloric acid.
- the solvent is acetic acid or aqueous acetic acid, for example a 1:2 acetic acid:water mixture.
- the reaction is carried out at a temperature which provides a suitable rate of formation of the required product, suitably at an elevated temperature, preferably above 70° C., for example in the range of from 80° C. to 115° C.
- the compounds of formula (I) are isolated from the reaction and subsequently purified by use of conventional isolation and purification methods such as chromatography and crystallization/recrystalliazation.
- a most preferred value of A 1 is a 2-pyridyl group.
- a most preferred value of A 2 is a moiety of formula:
- a most preferred value of R 1 is a methyl group.
- n 2
- a most preferred value of formula (I) is 5- ⁇ 4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl ⁇ -2,4-thiazolidinedione, or a tautomeric form thereof or a salt thereof, or a solvate thereof.
- Crystalline 5- ⁇ 4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzylidene ⁇ -2,4-thiazolidinedione is isolated from the present reaction and as such forms a further aspect of the present invention.
- a suitable crystallization/recrystallization solvent is denatured ethanol, the crystallization is favourably effected from refluxing solvent which is allowed to cool to provide the required compound.
- a most preferred value of formula (II) is 5- ⁇ 4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzylidene ⁇ -2,4-thiazolidinedione or a tautomeric form thereof or a salt thereof, or a solvate thereof.
- Suitable salts are pharmaceutically acceptable salts.
- Suitable pharmaceutically acceptable salts include metal salts, such as for example aluminium, alkali metal salts such as sodium or potassium, alkaline earth metal salts such as calcium or magnesium and ammonium or substituted ammonium salts, for example those with lower alkylamines such as triethylamine, hydroxy alkylamines such as 2-hydroxyethylamine, bis-(2-hydroxyethyl)-amine or tri-(2-hydroxyethyl)-anine, cycloalkylamines such as bicyclohexylamine, or with procaine, dibenzylpiperidine, N-benzyl-b-phenethylamine, dehydroabietylamine, N,N′-bisdehydroabietylamine, glucamine, N-methylglucamine or bases of the pyridine type such as pyridine, collidine or quinoline.
- metal salts such as for example aluminium, alkali metal salts such as sodium or potassium, alkaline earth metal salts
- salts provided by pharmaceutically acceptable acids including mineral acids, including salts provided by mineral acids, such as hydrobromic, hydrochloric and sulphuric acids, and organic acids, such as methanesulphonic, tartaric and maleic acids, especially tartaric and maleic acid.
- a preferred salt is a maleate salt.
- Suitable solvates are pharmaceutically acceptable solvates, such as hydrates.
- reaction time (hours.) 1 (75 psi, 100% catalyst) 15-20 2 1000 psi, 100% catalyst ⁇ 2 3 1000 psi, 50% catalyst 7 4 500 psi, 100% catalyst 4 5 500 psi, 50% catalyst ca. 12
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/326,003 US20060106221A1 (en) | 1997-11-04 | 2006-01-05 | Process for the preparation of thiazolidinedione derivatives |
US11/550,506 US7351832B2 (en) | 1997-11-04 | 2006-10-18 | Process for the preparation of thiazolidinedione derivatives |
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9723295.3A GB9723295D0 (en) | 1997-11-04 | 1997-11-04 | Novel process |
GB9723295.3 | 1997-11-04 | ||
PCT/EP1998/006997 WO1999023095A1 (en) | 1997-11-04 | 1998-10-27 | Process for the preparation of thiazolidinedione derivatives |
US53088800A | 2000-07-10 | 2000-07-10 | |
US10/082,995 US20020120150A1 (en) | 1997-11-04 | 2002-02-26 | Process for the preparation of thiazolidinedione derivatives |
US28807202A | 2002-11-04 | 2002-11-04 | |
US11/326,003 US20060106221A1 (en) | 1997-11-04 | 2006-01-05 | Process for the preparation of thiazolidinedione derivatives |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US28807202A Division | 1997-11-04 | 2002-11-04 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/550,506 Continuation US7351832B2 (en) | 1997-11-04 | 2006-10-18 | Process for the preparation of thiazolidinedione derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
US20060106221A1 true US20060106221A1 (en) | 2006-05-18 |
Family
ID=10821570
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/326,003 Abandoned US20060106221A1 (en) | 1997-11-04 | 2006-01-05 | Process for the preparation of thiazolidinedione derivatives |
US11/550,506 Expired - Fee Related US7351832B2 (en) | 1997-11-04 | 2006-10-18 | Process for the preparation of thiazolidinedione derivatives |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/550,506 Expired - Fee Related US7351832B2 (en) | 1997-11-04 | 2006-10-18 | Process for the preparation of thiazolidinedione derivatives |
Country Status (44)
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7091359B2 (en) | 1997-11-04 | 2006-08-15 | Smithkline Beecham Plc | Process for the preparation of thiazolidinedione derivatives |
GB9723295D0 (en) | 1997-11-04 | 1998-01-07 | Smithkline Beecham Plc | Novel process |
HU225919B1 (en) * | 1999-12-18 | 2007-12-28 | Richter Gedeon Nyrt | Thiazolidine-derivatives, process for their preparation pharmaceutical and intermediates |
GB0023971D0 (en) * | 2000-09-29 | 2000-11-15 | Smithkline Beecham Plc | Novel pharmaceutical |
GB0023970D0 (en) * | 2000-09-29 | 2000-11-15 | Smithkline Beecham Plc | Novel pharmaceutical |
AU2002366812A1 (en) * | 2001-12-20 | 2003-07-09 | Teva Pharmaceutical Industries Ltd. | Hydrogenation of precursors to thiazolidinedione antihyperglycemics |
GB0307259D0 (en) * | 2003-03-28 | 2003-05-07 | Glaxo Group Ltd | Process |
GB2405403A (en) * | 2003-08-29 | 2005-03-02 | Cipla Ltd | Rosiglitazone maleate of particular polymorphic forms and methods of preparing rosiglitazone free base |
AR047541A1 (es) * | 2004-02-13 | 2006-01-25 | Sandoz Ag | Fosfato de 5-[[4-[2-metil-2-piridinil-amino-etoxi]fenil]metil]-2,4 tiazolidinadiona (rosiglitazona) y sus formas polimorficas |
EP1745043A1 (en) * | 2004-05-12 | 2007-01-24 | Medichem S.A. | Process for the preparation of rosiglitazone |
CZ297266B6 (cs) * | 2004-09-10 | 2006-10-11 | Zentiva, A. S. | Zpusob prípravy rosiglitazonu |
CZ297347B6 (cs) * | 2004-09-21 | 2006-11-15 | Zentiva, A. S. | Zpusob prípravy rosiglitazonu |
CZ298424B6 (cs) * | 2005-05-24 | 2007-09-26 | Zentiva, A. S. | Zpusob krystalizace rosiglitazonu a jeho derivátuze smesných rozpouštedel |
CN102727489A (zh) * | 2012-07-18 | 2012-10-17 | 西南大学 | 5-芳(杂环)亚甲基噻唑烷-2,4-二酮在制备ppar激动剂中的应用 |
Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4725610A (en) * | 1984-10-03 | 1988-02-16 | Takeda Chemical Industries, Ltd. | Thiazolidinedione derivatives, their production and use |
US5002953A (en) * | 1987-09-04 | 1991-03-26 | Beecham Group P.L.C. | Novel compounds |
US5194443A (en) * | 1987-09-04 | 1993-03-16 | Beecham Group P.L.C. | Compounds |
US5232925A (en) * | 1987-09-04 | 1993-08-03 | Beecham Group P.L.C. | Compounds |
US5260445A (en) * | 1987-09-04 | 1993-11-09 | Beecham Group P.L.C. | 2,4-thiazolidinediones |
US5521201A (en) * | 1987-09-04 | 1996-05-28 | Beecham Group P.L.C. | Method for treatment of atherosclerosis |
US5726055A (en) * | 1991-11-19 | 1998-03-10 | Smithkline Beecham Plc | Process for the preparation of pharmaceutically active thiazolidine compounds by a yeast reductase |
US5741803A (en) * | 1992-09-05 | 1998-04-21 | Smithkline Beecham Plc | Substituted thiazolidinedionle derivatives |
US5910592A (en) * | 1992-09-05 | 1999-06-08 | Smithkline Beecham Plc | Substituted thiazolidinedione derivatives |
US6288095B1 (en) * | 1987-09-04 | 2001-09-11 | Beecham Group P.L.C. | Compounds |
US20020042519A1 (en) * | 1997-02-18 | 2002-04-11 | Smithkline Beecham P.L.C. | Process for the preparation of substituted thiazolidinedione |
US20020049240A1 (en) * | 1994-12-19 | 2002-04-25 | Beecham Group P.1.C. | Novel compounds |
US20020050563A1 (en) * | 1991-11-19 | 2002-05-02 | Smithkline Beecham P.L.C. | Process for the preparation of pharmaceutically active thiazolidine or oxazolidine compounds by a yeast reductase |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5522636A (en) | 1978-08-04 | 1980-02-18 | Takeda Chem Ind Ltd | Thiazoliding derivative |
US4812570A (en) | 1986-07-24 | 1989-03-14 | Takeda Chemical Industries, Ltd. | Method for producing thiazolidinedione derivatives |
GB9023583D0 (en) * | 1990-10-30 | 1990-12-12 | Beecham Group Plc | Novel compounds |
GB9023585D0 (en) * | 1990-10-30 | 1990-12-12 | Beecham Group Plc | Novel compounds |
US5585495A (en) | 1991-12-20 | 1996-12-17 | The Upjohn Company | Reduction method for substituted 5-methylene-thiazolidinediones |
UY24886A1 (es) | 1997-02-18 | 2001-08-27 | Smithkline Beecham Plc | Tiazolidindiona |
US7091359B2 (en) * | 1997-11-04 | 2006-08-15 | Smithkline Beecham Plc | Process for the preparation of thiazolidinedione derivatives |
GB9723295D0 (en) | 1997-11-04 | 1998-01-07 | Smithkline Beecham Plc | Novel process |
-
1997
- 1997-11-04 GB GBGB9723295.3A patent/GB9723295D0/en not_active Ceased
-
1998
- 1998-10-27 CN CNB98810959XA patent/CN1160351C/zh not_active Expired - Fee Related
- 1998-10-27 HU HU0100144A patent/HU224547B1/hu not_active IP Right Cessation
- 1998-10-27 CA CA002309461A patent/CA2309461A1/en not_active Abandoned
- 1998-10-27 TR TR2000/01239T patent/TR200001239T2/xx unknown
- 1998-10-27 AT AT98959834T patent/ATE238302T1/de active
- 1998-10-27 AU AU15595/99A patent/AU1559599A/en not_active Abandoned
- 1998-10-27 IL IL13589898A patent/IL135898A/xx unknown
- 1998-10-27 UA UA2000042451A patent/UA56269C2/uk unknown
- 1998-10-27 BR BR9814622-0A patent/BR9814622A/pt not_active Application Discontinuation
- 1998-10-27 RS YUP-338/00A patent/RS49793B/sr unknown
- 1998-10-27 SK SK650-2000A patent/SK285233B6/sk not_active IP Right Cessation
- 1998-10-27 DE DE69813869T patent/DE69813869T2/de not_active Expired - Lifetime
- 1998-10-27 AP APAP/P/2000/001808A patent/AP1519A/en active
- 1998-10-27 CZ CZ20001633A patent/CZ297209B6/cs not_active IP Right Cessation
- 1998-10-27 SI SI9830468T patent/SI1028960T1/xx unknown
- 1998-10-27 WO PCT/EP1998/006997 patent/WO1999023095A1/en active IP Right Grant
- 1998-10-27 ES ES98959834T patent/ES2197519T3/es not_active Expired - Lifetime
- 1998-10-27 KR KR1020007004783A patent/KR100602551B1/ko not_active IP Right Cessation
- 1998-10-27 EP EP02075969A patent/EP1219620A1/en not_active Withdrawn
- 1998-10-27 OA OA1200000131A patent/OA11521A/en unknown
- 1998-10-27 JP JP2000518965A patent/JP3723448B2/ja not_active Expired - Fee Related
- 1998-10-27 PT PT98959834T patent/PT1028960E/pt unknown
- 1998-10-27 EA EA200000484A patent/EA002722B1/ru not_active IP Right Cessation
- 1998-10-27 PL PL340366A patent/PL192503B1/pl not_active IP Right Cessation
- 1998-10-27 ID IDW20000822A patent/ID24644A/id unknown
- 1998-10-27 EP EP98959834A patent/EP1028960B1/en not_active Expired - Lifetime
- 1998-10-27 DK DK98959834T patent/DK1028960T3/da active
- 1998-10-28 UY UY25227A patent/UY25227A1/es not_active IP Right Cessation
- 1998-11-02 AR ARP980105505A patent/AR016660A1/es active IP Right Grant
- 1998-11-02 MY MYPI98004975A patent/MY118605A/en unknown
- 1998-11-02 MA MA25328A patent/MA26560A1/fr unknown
- 1998-11-03 ZA ZA9810033A patent/ZA9810033B/xx unknown
- 1998-11-03 TW TW087118222A patent/TW538037B/zh not_active IP Right Cessation
- 1998-11-03 IN IN3258DE1998 patent/IN192870B/en unknown
- 1998-11-03 PE PE1998001038A patent/PE129399A1/es not_active Application Discontinuation
- 1998-11-03 CO CO98064433A patent/CO5011075A1/es unknown
- 1998-11-03 DZ DZ980247A patent/DZ2637A1/xx active
- 1998-11-25 SA SA98190820A patent/SA98190820B1/ar unknown
-
2000
- 2000-04-27 NO NO20002174A patent/NO315557B1/no not_active IP Right Cessation
- 2000-05-04 HR HR20000263A patent/HRP20000263B1/xx not_active IP Right Cessation
- 2000-06-05 BG BG104505A patent/BG64559B1/bg unknown
-
2001
- 2001-02-02 HK HK02108713.7A patent/HK1048804A1/zh unknown
- 2001-02-02 HK HK01100772A patent/HK1032046A1/xx not_active IP Right Cessation
-
2002
- 2002-07-09 AU AU2002300593A patent/AU2002300593B8/en not_active Ceased
-
2004
- 2004-08-04 JP JP2004228226A patent/JP2004339235A/ja active Pending
-
2006
- 2006-01-05 US US11/326,003 patent/US20060106221A1/en not_active Abandoned
- 2006-10-18 US US11/550,506 patent/US7351832B2/en not_active Expired - Fee Related
-
2008
- 2008-07-08 EC EC2008002712A patent/ECSP082712A/es unknown
Patent Citations (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4725610A (en) * | 1984-10-03 | 1988-02-16 | Takeda Chemical Industries, Ltd. | Thiazolidinedione derivatives, their production and use |
US5646169A (en) * | 1987-09-04 | 1997-07-08 | Beecham Group P.L.C. | Compounds for treating eating disorders in which blood glucose levels are raised |
US5194443A (en) * | 1987-09-04 | 1993-03-16 | Beecham Group P.L.C. | Compounds |
US5232925A (en) * | 1987-09-04 | 1993-08-03 | Beecham Group P.L.C. | Compounds |
US5260445A (en) * | 1987-09-04 | 1993-11-09 | Beecham Group P.L.C. | 2,4-thiazolidinediones |
US5521201A (en) * | 1987-09-04 | 1996-05-28 | Beecham Group P.L.C. | Method for treatment of atherosclerosis |
US5002953A (en) * | 1987-09-04 | 1991-03-26 | Beecham Group P.L.C. | Novel compounds |
US5756525A (en) * | 1987-09-04 | 1998-05-26 | Beecham Group Plc | Compounds for treating eating disorders |
US6288095B1 (en) * | 1987-09-04 | 2001-09-11 | Beecham Group P.L.C. | Compounds |
US6686475B2 (en) * | 1988-08-30 | 2004-02-03 | Beecham Group P.L.C. | Compounds |
US20020050563A1 (en) * | 1991-11-19 | 2002-05-02 | Smithkline Beecham P.L.C. | Process for the preparation of pharmaceutically active thiazolidine or oxazolidine compounds by a yeast reductase |
US5726055A (en) * | 1991-11-19 | 1998-03-10 | Smithkline Beecham Plc | Process for the preparation of pharmaceutically active thiazolidine compounds by a yeast reductase |
US20020106762A1 (en) * | 1991-11-19 | 2002-08-08 | Smith Kline Beecham Plc | Process for the preparation of pharmaceutically active thiazolidine or oxazolidine compounds by a yeast reductase |
US5741803A (en) * | 1992-09-05 | 1998-04-21 | Smithkline Beecham Plc | Substituted thiazolidinedionle derivatives |
US5910592A (en) * | 1992-09-05 | 1999-06-08 | Smithkline Beecham Plc | Substituted thiazolidinedione derivatives |
US20020049240A1 (en) * | 1994-12-19 | 2002-04-25 | Beecham Group P.1.C. | Novel compounds |
US20020042519A1 (en) * | 1997-02-18 | 2002-04-11 | Smithkline Beecham P.L.C. | Process for the preparation of substituted thiazolidinedione |
US6632947B2 (en) * | 1997-02-18 | 2003-10-14 | Smithkline Beecham Plc | Process for the preparation of substituted thiazolidinedione |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |