JP2004509121A - チアゾリジン誘導体および抗真菌剤としてのその使用 - Google Patents
チアゾリジン誘導体および抗真菌剤としてのその使用 Download PDFInfo
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- JP2004509121A JP2004509121A JP2002526865A JP2002526865A JP2004509121A JP 2004509121 A JP2004509121 A JP 2004509121A JP 2002526865 A JP2002526865 A JP 2002526865A JP 2002526865 A JP2002526865 A JP 2002526865A JP 2004509121 A JP2004509121 A JP 2004509121A
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- Prior art keywords
- phenyl
- oxo
- methylene
- thioxo
- branched
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- 239000003429 antifungal agent Substances 0.000 title claims description 8
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- 206010017533 Fungal infection Diseases 0.000 claims abstract description 12
- 208000031888 Mycoses Diseases 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 84
- -1 N-methyl-N-phenylamino Chemical group 0.000 claims description 83
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 71
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- 238000000034 method Methods 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
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- 125000003118 aryl group Chemical group 0.000 claims description 9
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- HAQCAFHUWZJBFB-UHFFFAOYSA-N 2-[5-[[3-[(dipentylamino)methyl]-4-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(CN(CCCCC)CCCCC)=CC=1C=C1SC(=S)N(CC(O)=O)C1=O HAQCAFHUWZJBFB-UHFFFAOYSA-N 0.000 claims description 4
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
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- 239000003085 diluting agent Substances 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 150000005671 trienes Chemical class 0.000 claims 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 139
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 90
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 58
- 238000005160 1H NMR spectroscopy Methods 0.000 description 57
- 239000000243 solution Substances 0.000 description 48
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 21
- 235000011152 sodium sulphate Nutrition 0.000 description 21
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- 239000000203 mixture Substances 0.000 description 17
- 239000012267 brine Substances 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
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- 239000003480 eluent Substances 0.000 description 11
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- HZQDBFJELNYTKE-UHFFFAOYSA-N (5-formyl-2-phenylmethoxyphenyl)methyl methanesulfonate Chemical compound CS(=O)(=O)OCC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 HZQDBFJELNYTKE-UHFFFAOYSA-N 0.000 description 8
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- FTTVXHXKTPOQDV-UHFFFAOYSA-N 5-formyl-2-phenylmethoxybenzoic acid Chemical compound OC(=O)C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 FTTVXHXKTPOQDV-UHFFFAOYSA-N 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
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- 125000000311 mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GVEOLVGLJIFQIT-UHFFFAOYSA-N n,n-dibenzyl-2-(5-formyl-2-phenylmethoxyphenyl)benzamide Chemical compound C=1C=CC=C(C(=O)N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=1C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 GVEOLVGLJIFQIT-UHFFFAOYSA-N 0.000 description 1
- XXFIJEIPRAYRGO-UHFFFAOYSA-N n,n-dibutyl-5-formyl-2-phenylmethoxybenzamide Chemical compound CCCCN(CCCC)C(=O)C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 XXFIJEIPRAYRGO-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 230000037125 natural defense Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000036573 scar formation Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003239 susceptibility assay Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0021419.7A GB0021419D0 (en) | 2000-08-31 | 2000-08-31 | Compounds |
| PCT/GB2001/003860 WO2002022612A1 (en) | 2000-08-31 | 2001-08-30 | Thiazolidine derivatives and its use as antifungal agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004509121A true JP2004509121A (ja) | 2004-03-25 |
| JP2004509121A5 JP2004509121A5 (OSRAM) | 2005-03-03 |
Family
ID=9898614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002526865A Pending JP2004509121A (ja) | 2000-08-31 | 2001-08-30 | チアゾリジン誘導体および抗真菌剤としてのその使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6740670B2 (OSRAM) |
| EP (1) | EP1313731B1 (OSRAM) |
| JP (1) | JP2004509121A (OSRAM) |
| AT (1) | ATE482954T1 (OSRAM) |
| AU (1) | AU2001284188A1 (OSRAM) |
| DE (1) | DE60143165D1 (OSRAM) |
| ES (1) | ES2353685T3 (OSRAM) |
| GB (1) | GB0021419D0 (OSRAM) |
| WO (1) | WO2002022612A1 (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ544820A (en) * | 2003-08-11 | 2009-02-28 | Hoffmann La Roche | Piperazine with or-substituted phenyl group and their use as GlyT1 inhibitors |
| RS54199B1 (sr) | 2004-03-15 | 2015-12-31 | Janssen Pharmaceutica Nv | Postupak za dobijanje intermedijera jedinjenja korisnih kao modulatori opioidnih receptora |
| ATE430142T1 (de) | 2004-12-09 | 2009-05-15 | Hoffmann La Roche | Phenylpiperazin-methanon-derivate |
| ES2338139T3 (es) | 2004-12-15 | 2010-05-04 | F. Hoffmann-La Roche Ag | Fenil-metanonas bi- y triciclicas sustituidas como inhibidores del transportador de la glicina i (glyt-1) para el tratamiento de la enfermedad de alzheimer. |
| US7485637B2 (en) | 2005-01-04 | 2009-02-03 | Hoffmann-La Roche Inc. | Benzoyl-tetrahydropiperidine derivatives |
| CA2593463C (en) | 2005-01-07 | 2013-10-08 | F. Hoffmann-La Roche Ag | [4-(heteroaryl) piperazin-1-yl]-(2,5-substituted -phenyl)methanone derivatives as glycine transporter 1 (glyt-1) inhibitors for the treatment of neurological and neuropsychiatric disorders |
| DE602006007682D1 (de) | 2005-01-18 | 2009-08-20 | Hoffmann La Roche | 2,5-disubstituierte phenylmethanonderivative als glycintransporter-1-inhibitoren (glyt-1) zur behandlung von neurologischen und neuropsychiatrischen störungen |
| RU2007126951A (ru) | 2005-01-26 | 2009-03-10 | Ф.Хоффманн-Ля Рош Аг (Ch) | Производные фенилметанона и их применение в качестве ингибиторов переносчика глицина 1 |
| DK1848694T3 (da) | 2005-02-07 | 2010-01-25 | Hoffmann La Roche | Heterocykliske substituerede phenylmethanoner som inhibitorer af glycintransporter |
| CA2721459A1 (en) | 2008-05-20 | 2009-11-26 | Merck Sharp & Dohme Corp. | Efficient production of heterologous proteins using mannosyl transferase inhibitors |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| 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 |
| US11292776B2 (en) | 2019-12-12 | 2022-04-05 | University Of Sharjah | Small molecule inhibitors of fungal hyphae and biofilm formation |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5740478A (en) * | 1980-08-22 | 1982-03-06 | Ono Pharmaceut Co Ltd | Rhodanine derivative, its preparation and aldose reductase inhibitor containing rhodanine derivative |
| WO1994029287A1 (de) * | 1993-06-04 | 1994-12-22 | Boehringer Mannheim Gmbh | Aryliden-4-oxo-2-thioxo-3-thiazolidincarbonsäuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| WO2000008747A1 (de) * | 1998-08-05 | 2000-02-17 | Robert Bosch Gmbh | Gesteuerte gleichrichterbrücke mit überspannungsschutz |
| WO2000018747A1 (en) * | 1998-09-30 | 2000-04-06 | Roche Diagnostics Gmbh | Rhodanine carboxylic acid derivatives for the treatment and prevention of metabolic bone disorders |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US47109A (en) * | 1865-04-04 | Improvement in governors | ||
| FR1548312A (OSRAM) * | 1967-06-06 | 1968-12-06 |
-
2000
- 2000-08-31 GB GBGB0021419.7A patent/GB0021419D0/en not_active Ceased
-
2001
- 2001-08-30 JP JP2002526865A patent/JP2004509121A/ja active Pending
- 2001-08-30 WO PCT/GB2001/003860 patent/WO2002022612A1/en not_active Ceased
- 2001-08-30 AU AU2001284188A patent/AU2001284188A1/en not_active Abandoned
- 2001-08-30 AT AT01963155T patent/ATE482954T1/de active
- 2001-08-30 DE DE60143165T patent/DE60143165D1/de not_active Expired - Lifetime
- 2001-08-30 EP EP01963155A patent/EP1313731B1/en not_active Expired - Lifetime
- 2001-08-30 ES ES01963155T patent/ES2353685T3/es not_active Expired - Lifetime
-
2003
- 2003-02-21 US US10/371,979 patent/US6740670B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5740478A (en) * | 1980-08-22 | 1982-03-06 | Ono Pharmaceut Co Ltd | Rhodanine derivative, its preparation and aldose reductase inhibitor containing rhodanine derivative |
| WO1994029287A1 (de) * | 1993-06-04 | 1994-12-22 | Boehringer Mannheim Gmbh | Aryliden-4-oxo-2-thioxo-3-thiazolidincarbonsäuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| WO2000008747A1 (de) * | 1998-08-05 | 2000-02-17 | Robert Bosch Gmbh | Gesteuerte gleichrichterbrücke mit überspannungsschutz |
| WO2000018747A1 (en) * | 1998-09-30 | 2000-04-06 | Roche Diagnostics Gmbh | Rhodanine carboxylic acid derivatives for the treatment and prevention of metabolic bone disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001284188A1 (en) | 2002-03-26 |
| WO2002022612A1 (en) | 2002-03-21 |
| ATE482954T1 (de) | 2010-10-15 |
| ES2353685T3 (es) | 2011-03-04 |
| US20030216453A1 (en) | 2003-11-20 |
| DE60143165D1 (de) | 2010-11-11 |
| WO2002022612A8 (en) | 2002-05-23 |
| EP1313731A1 (en) | 2003-05-28 |
| EP1313731B1 (en) | 2010-09-29 |
| GB0021419D0 (en) | 2000-10-18 |
| US6740670B2 (en) | 2004-05-25 |
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