JP2004507501A5 - - Google Patents
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- Publication number
- JP2004507501A5 JP2004507501A5 JP2002522888A JP2002522888A JP2004507501A5 JP 2004507501 A5 JP2004507501 A5 JP 2004507501A5 JP 2002522888 A JP2002522888 A JP 2002522888A JP 2002522888 A JP2002522888 A JP 2002522888A JP 2004507501 A5 JP2004507501 A5 JP 2004507501A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- branched
- methylene
- phenylmethoxy
- thioxo
- 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.)
- Pending
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000005975 2-phenylethyloxy group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 101100495911 Arabidopsis thaliana CHR10 gene Proteins 0.000 claims description 3
- MFCHSBDIWCBMFE-LJQANCHMSA-N 2-[4-oxo-5-[[3-phenylmethoxy-4-[(2s)-2-phenylpropoxy]phenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound C([C@@H](C)C=1C=CC=CC=1)OC(C(=C1)OCC=2C=CC=CC=2)=CC=C1C=C1SC(=S)N(CC(O)=O)C1=O MFCHSBDIWCBMFE-LJQANCHMSA-N 0.000 claims description 2
- AOAROSLFYLNGCD-UHFFFAOYSA-N 2-[4-oxo-5-[[4-(2-phenylethoxy)-3-(2,2,2-trifluoro-1-phenylethoxy)phenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OC(C=2C=CC=CC=2)C(F)(F)F)=CC=C1OCCC1=CC=CC=C1 AOAROSLFYLNGCD-UHFFFAOYSA-N 0.000 claims description 2
- STQKCXNXIQARBH-UHFFFAOYSA-N 2-[4-oxo-5-[[4-(2-phenylethoxy)-3-(pyridin-2-ylmethoxy)phenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid hydrochloride Chemical compound Cl.O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2N=CC=CC=2)=CC=C1OCCC1=CC=CC=C1 STQKCXNXIQARBH-UHFFFAOYSA-N 0.000 claims description 2
- RYINIELRRQTSQL-UHFFFAOYSA-N 2-[5-[[4-(2-cyclohexylethoxy)-3-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCCC1CCCCC1 RYINIELRRQTSQL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 19
- -1 phenylmethoxy Chemical group 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- MQCZHTDGFLSFOD-UHFFFAOYSA-N 2-[4-oxo-5-[[4-(2-phenylethoxy)-3-phenylmethoxyphenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCCC1=CC=CC=C1 MQCZHTDGFLSFOD-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- 206010017533 Fungal infection Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000031888 Mycoses Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 229940121375 antifungal agent Drugs 0.000 claims 2
- 239000003429 antifungal agent Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- KOYJKQFGCGIFEU-UHFFFAOYSA-N 2-[4-oxo-5-[[3-(phenoxymethyl)-4-phenylmethoxyphenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1COC=2C=CC=CC=2)=CC=C1OCC1=CC=CC=C1 KOYJKQFGCGIFEU-UHFFFAOYSA-N 0.000 claims 1
- GIHSGMSTRANTBM-UHFFFAOYSA-N 2-[4-oxo-5-[[3-phenylmethoxy-4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCC1=CC=CC(C(F)(F)F)=C1 GIHSGMSTRANTBM-UHFFFAOYSA-N 0.000 claims 1
- QBKDSAYHKBXKQL-UHFFFAOYSA-N 2-[4-oxo-5-[[3-phenylmethoxy-4-[[4-(trifluoromethoxy)phenyl]methoxy]phenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCC1=CC=C(OC(F)(F)F)C=C1 QBKDSAYHKBXKQL-UHFFFAOYSA-N 0.000 claims 1
- KWYBOLDSAURJIK-UHFFFAOYSA-N 2-[4-oxo-5-[[3-phenylmethoxy-4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 KWYBOLDSAURJIK-UHFFFAOYSA-N 0.000 claims 1
- YAHWWUNPHNZBOT-UHFFFAOYSA-N 2-[4-oxo-5-[[4-(2,2,3,3,3-pentafluoropropoxy)-3-phenylmethoxyphenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC1=CC=C(OCC(F)(F)C(F)(F)F)C(OCC=2C=CC=CC=2)=C1 YAHWWUNPHNZBOT-UHFFFAOYSA-N 0.000 claims 1
- XTFYPIJXZLFEAR-UHFFFAOYSA-N 2-[5-[[3,4-bis[(2,4-difluorophenyl)methoxy]phenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C(=CC(F)=CC=2)F)=CC=C1OCC1=CC=C(F)C=C1F XTFYPIJXZLFEAR-UHFFFAOYSA-N 0.000 claims 1
- XGNWOQWQTFJAQN-UHFFFAOYSA-N 2-[5-[[3,4-bis[(4-fluorophenyl)methoxy]phenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC(F)=CC=2)=CC=C1OCC1=CC=C(F)C=C1 XGNWOQWQTFJAQN-UHFFFAOYSA-N 0.000 claims 1
- LIXVFUFBYFQXDV-UHFFFAOYSA-N 2-[5-[[3-(2-hydroxy-1-phenylethoxy)-4-(2-phenylethoxy)phenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound C=1C=CC=CC=1C(CO)OC(C(=CC=1)OCCC=2C=CC=CC=2)=CC=1C=C1SC(=S)N(CC(O)=O)C1=O LIXVFUFBYFQXDV-UHFFFAOYSA-N 0.000 claims 1
- JDVBNGAJBKGNLT-UHFFFAOYSA-N 2-[5-[[3-[(3,4-difluorophenyl)methoxy]-4-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=C(F)C(F)=CC=2)=CC=C1OCC1=CC=CC=C1 JDVBNGAJBKGNLT-UHFFFAOYSA-N 0.000 claims 1
- ZBURNDZUTYZCKH-UHFFFAOYSA-N 2-[5-[[4-[(2,4-difluorophenyl)methoxy]-3-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCC1=CC=C(F)C=C1F ZBURNDZUTYZCKH-UHFFFAOYSA-N 0.000 claims 1
- ICNYEXXENSBATD-UHFFFAOYSA-N 2-[5-[[4-[(3,4-difluorophenyl)methoxy]-3-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCC1=CC=C(F)C(F)=C1 ICNYEXXENSBATD-UHFFFAOYSA-N 0.000 claims 1
- OWSLGYWEPUDVAT-UHFFFAOYSA-N 2-[5-[[4-[(4-chlorophenyl)methoxy]-3-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCC1=CC=C(Cl)C=C1 OWSLGYWEPUDVAT-UHFFFAOYSA-N 0.000 claims 1
- SSKLGZLYOABIDO-UHFFFAOYSA-N 2-[5-[[4-[2-(4-chlorophenyl)ethoxy]-3-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCCC1=CC=C(Cl)C=C1 SSKLGZLYOABIDO-UHFFFAOYSA-N 0.000 claims 1
- FXPLNNDKZYARSZ-UHFFFAOYSA-N 2-[5-[[4-[2-(4-fluorophenyl)ethoxy]-3-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCCC1=CC=C(F)C=C1 FXPLNNDKZYARSZ-UHFFFAOYSA-N 0.000 claims 1
- YNOGAFPQUMNNHQ-UHFFFAOYSA-N 2-[5-[[4-[[3,5-bis(trifluoromethyl)phenyl]methoxy]-3-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YNOGAFPQUMNNHQ-UHFFFAOYSA-N 0.000 claims 1
- FFYJVTLTZYPAAB-UQQQWYQISA-N 5-[[3-(1-phenylethoxy)-4-(2-phenylethoxy)phenyl]methylene]-4-oxo-2-thioxo-3-thiazolidineacetic acid Chemical compound C=1C=CC=CC=1C(C)OC(C(=CC=1)OCCC=2C=CC=CC=2)=CC=1\C=C1/SC(=S)N(CC(O)=O)C1=O FFYJVTLTZYPAAB-UQQQWYQISA-N 0.000 claims 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 1
- 239000005695 Ammonium acetate Substances 0.000 claims 1
- 241000228197 Aspergillus flavus Species 0.000 claims 1
- 241001225321 Aspergillus fumigatus Species 0.000 claims 1
- 241000335423 Blastomyces Species 0.000 claims 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims 1
- 241000223203 Coccidioides Species 0.000 claims 1
- 201000007336 Cryptococcosis Diseases 0.000 claims 1
- 241000221204 Cryptococcus neoformans Species 0.000 claims 1
- 241001480035 Epidermophyton Species 0.000 claims 1
- 241000228402 Histoplasma Species 0.000 claims 1
- 241001480037 Microsporum Species 0.000 claims 1
- 241001537205 Paracoccidioides Species 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 241000223238 Trichophyton Species 0.000 claims 1
- 229940043376 ammonium acetate Drugs 0.000 claims 1
- 235000019257 ammonium acetate Nutrition 0.000 claims 1
- 229940091771 aspergillus fumigatus Drugs 0.000 claims 1
- 150000003935 benzaldehydes Chemical class 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0021421.3A GB0021421D0 (en) | 2000-08-31 | 2000-08-31 | Compounds |
| PCT/GB2001/003862 WO2002017915A1 (en) | 2000-08-31 | 2001-08-30 | Benzylidene thiazolidinediones and their use as antimycotic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004507501A JP2004507501A (ja) | 2004-03-11 |
| JP2004507501A5 true JP2004507501A5 (enExample) | 2005-04-14 |
Family
ID=9898616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002522888A Pending JP2004507501A (ja) | 2000-08-31 | 2001-08-30 | ベンジリデンチアゾリジンジオンおよび抗真菌剤としてのそれらの使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7105554B2 (enExample) |
| EP (1) | EP1313471B1 (enExample) |
| JP (1) | JP2004507501A (enExample) |
| AT (1) | ATE359073T1 (enExample) |
| AU (1) | AU2001284190A1 (enExample) |
| DE (1) | DE60127845T2 (enExample) |
| ES (1) | ES2282283T3 (enExample) |
| GB (1) | GB0021421D0 (enExample) |
| WO (1) | WO2002017915A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0204252D0 (en) * | 2002-02-23 | 2002-04-10 | Oxford Glycosciences Uk Ltd | Novel compounds |
| WO2003070238A1 (en) * | 2002-02-23 | 2003-08-28 | Oxford Glycosciences (Uk) Ltd | Thiazolidine antifungal agents |
| AU2005225632B2 (en) | 2004-03-23 | 2011-08-04 | Pfizer Inc. | Formamide derivatives useful as adrenoceptor |
| EP1954815B1 (en) * | 2005-11-15 | 2015-02-25 | GlycoFi, Inc. | Production of glycoproteins with reduced o-glycosylation |
| WO2007079466A2 (en) * | 2006-01-04 | 2007-07-12 | Nano Mist International, Llc | Air driven delivery system for sprayable media |
| US8637435B2 (en) * | 2007-11-16 | 2014-01-28 | Merck Sharp & Dohme Corp. | Eukaryotic cell display systems |
| WO2009111183A1 (en) * | 2008-03-03 | 2009-09-11 | Glycofi, Inc. | Surface display of recombinant proteins in lower eukaryotes |
| ATE536347T1 (de) * | 2008-05-20 | 2011-12-15 | Merck Sharp & Dohme | Effiziente herstellung heterologer proteine unter verwendung von mannosyltransferaseinhibitoren |
| US8067339B2 (en) | 2008-07-09 | 2011-11-29 | Merck Sharp & Dohme Corp. | Surface display of whole antibodies in eukaryotes |
| JP2011530311A (ja) | 2008-08-12 | 2011-12-22 | グライコフィ， インコーポレイテッド | タンパク質製造のための改良されたベクターおよび酵母株：Ｃａ２＋ＡＴＰアーゼ過剰発現 |
| US8936918B2 (en) | 2011-02-25 | 2015-01-20 | Merck Sharp & Dohme Corp. | Yeast strain for the production of proteins with modified O-glycosylation |
| MX336268B (es) * | 2011-07-29 | 2016-01-13 | Toyama Chemical Co Ltd | Compuesto de amidina o sal del mismo. |
| WO2014024897A1 (ja) * | 2012-08-06 | 2014-02-13 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | チアゾリジンジオンおよびピロリジンジオン誘導体、並びにそれらを有効成分としてなる殺菌剤 |
| US9261497B2 (en) | 2012-10-16 | 2016-02-16 | New York University | Method of treating cancer with modulators of SCFSkp2 |
| WO2015001049A1 (en) | 2013-07-04 | 2015-01-08 | Novartis Ag | O-mannosyltransferase deficient filamentous fungal cells and methods of use thereof |
| CN108064266A (zh) | 2014-07-21 | 2018-05-22 | 格利科斯芬兰公司 | 在丝状真菌中具有哺乳动物样n-聚糖的糖蛋白的制备 |
| JP2019523229A (ja) * | 2016-06-14 | 2019-08-22 | ヴェルシテック リミテッド | 抗微生物化合物及びその使用方法 |
| WO2017223473A1 (en) * | 2016-06-24 | 2017-12-28 | Ohio University | Glucose transport inhibitors and methods of using same |
| RU2662153C1 (ru) * | 2017-04-20 | 2018-07-24 | Общество С Ограниченной Ответственностью "Дермавитал Групп" | Гибридные эфиры на основе производных тиазолидин-2,4-диона и азолов (1н-1,3-имидазола и 1н-1,3,4-триазола) и их применение |
| RU2690161C1 (ru) * | 2018-06-28 | 2019-05-31 | Общество С Ограниченной Ответственностью "Дермавитал Групп" | 3,5-Замещенные производные тиазолидин-2,4-диона, обладающие противомикробной активностью |
| RU2703997C1 (ru) * | 2018-12-13 | 2019-10-23 | Общество с ограниченной ответственностью "Л-Био" | Гибридные амиды на основе триазола и тиазолидина, обладающие антимикробной активностью |
| CN112521382A (zh) * | 2020-12-14 | 2021-03-19 | 西南大学 | 芦荟大黄素噻唑烷二酮类化合物及其制备方法和应用 |
| WO2024258316A1 (ru) * | 2023-06-16 | 2024-12-19 | Общество с ограниченной ответственностью "Л-Био" | Новые потенциальные противогрибковые средства на основе тиазолидин-2,4-диона и триазола |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6156175A (ja) * | 1984-08-24 | 1986-03-20 | Yamanouchi Pharmaceut Co Ltd | ロダニン誘導体およびその製造法 |
| EP0915090A1 (en) * | 1992-09-10 | 1999-05-12 | Eli Lilly And Company | Compounds useful as hypoglycemic agents and for treating Alzheimer's disease |
| DE4318550A1 (de) * | 1993-06-04 | 1994-12-08 | Boehringer Mannheim Gmbh | Aryliden-4-oxo-2-thioxo-3- thiazolidincarbonsäuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| JPH08109174A (ja) * | 1994-10-07 | 1996-04-30 | Torii Yakuhin Kk | チアゾリジン−２−オン誘導体 |
| JPH08109175A (ja) * | 1994-10-07 | 1996-04-30 | Torii Yakuhin Kk | チアゾリジン−２−オンエステル誘導体 |
| AU6331099A (en) * | 1998-09-30 | 2000-04-17 | Roche Diagnostics Gmbh | Thiazolidine derivatives for the treatment and prevention of metabolic bone disorders |
| AU6330799A (en) * | 1998-09-30 | 2000-04-17 | Roche Diagnostics Gmbh | Rhodanine carboxylic acid derivatives for the treatment and prevention of metabolic bone disorders |
| US6506755B2 (en) * | 2000-02-03 | 2003-01-14 | Hoffmann-La Roche Inc. | Thiazolidinecarboxyl acids |
-
2000
- 2000-08-31 GB GBGB0021421.3A patent/GB0021421D0/en not_active Ceased
-
2001
- 2001-08-30 EP EP01963157A patent/EP1313471B1/en not_active Expired - Lifetime
- 2001-08-30 DE DE60127845T patent/DE60127845T2/de not_active Expired - Lifetime
- 2001-08-30 AT AT01963157T patent/ATE359073T1/de not_active IP Right Cessation
- 2001-08-30 WO PCT/GB2001/003862 patent/WO2002017915A1/en not_active Ceased
- 2001-08-30 ES ES01963157T patent/ES2282283T3/es not_active Expired - Lifetime
- 2001-08-30 JP JP2002522888A patent/JP2004507501A/ja active Pending
- 2001-08-30 AU AU2001284190A patent/AU2001284190A1/en not_active Abandoned
-
2003
- 2003-02-21 US US10/371,964 patent/US7105554B2/en not_active Expired - Fee Related
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