ES2282283T3 - Derivados de bencilideno tiazolidinadionas y su uso como agentes antifungicos. - Google Patents

Derivados de bencilideno tiazolidinadionas y su uso como agentes antifungicos. Download PDF

Info

Publication number: ES2282283T3
Authority: ES; Spain
Prior art keywords: phenyl; acid; phenylmethoxy; methylene; thioxo
Prior art date: 2000-08-31
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.): Expired - Lifetime

Application number

ES01963157T

Other languages

English (en)

Spanish (es)

Inventor

Michael Glen Oxford GlycoSci. ORCHARD (UK) Ltd.

Judi Charlotte Oxford GlycoSci. NEUSS (UK) Ltd.

Carl Maurice Swedler Galley

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

UCB SA

Original Assignee

UCB SA

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.)

2000-08-31

Filing date

2001-08-30

Publication date

2007-10-16

2001-08-30 Application filed by UCB SA filed Critical UCB SA

2007-10-16 Application granted granted Critical

2007-10-16 Publication of ES2282283T3 publication Critical patent/ES2282283T3/es

2021-08-30 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

230000001716 anti-fugal effect Effects 0.000 title 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 171
150000001875 compounds Chemical class 0.000 claims abstract description 106
125000000217 alkyl group Chemical group 0.000 claims abstract description 49
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
239000001257 hydrogen Substances 0.000 claims abstract description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
238000011282 treatment Methods 0.000 claims abstract description 17
125000003118 aryl group Chemical group 0.000 claims abstract description 14
239000003814 drug Substances 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 14
125000001424 substituent group Chemical group 0.000 claims abstract description 13
206010017533 Fungal infection Diseases 0.000 claims abstract description 12
208000031888 Mycoses Diseases 0.000 claims abstract description 10
125000002541 furyl group Chemical group 0.000 claims abstract description 10
125000004076 pyridyl group Chemical group 0.000 claims abstract description 10
125000001544 thienyl group Chemical group 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
238000011321 prophylaxis Methods 0.000 claims abstract description 6
125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 5
238000004519 manufacturing process Methods 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
125000005865 C2-C10alkynyl group Chemical group 0.000 claims abstract description 3
101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims description 160
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 137
-1 phenylmethoxy Chemical group 0.000 claims description 119
125000005975 2-phenylethyloxy group Chemical group 0.000 claims description 56
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
239000008194 pharmaceutical composition Substances 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
208000015181 infectious disease Diseases 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 12
241000222120 Candida <Saccharomycetales> Species 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
239000003981 vehicle Substances 0.000 claims description 7
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
125000005976 1-phenylethyloxy group Chemical group 0.000 claims description 4
241000228197 Aspergillus flavus Species 0.000 claims description 4
241001225321 Aspergillus fumigatus Species 0.000 claims description 4
241000223203 Coccidioides Species 0.000 claims description 4
201000007336 Cryptococcosis Diseases 0.000 claims description 4
241000221204 Cryptococcus neoformans Species 0.000 claims description 4
241001480035 Epidermophyton Species 0.000 claims description 4
241000228402 Histoplasma Species 0.000 claims description 4
241001537205 Paracoccidioides Species 0.000 claims description 4
241000223238 Trichophyton Species 0.000 claims description 4
229940091771 aspergillus fumigatus Drugs 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
SVNWHWFUTFGAIW-UHFFFAOYSA-N 2-[4-oxo-5-[[4-(2-phenylethoxy)-3-phenylmethoxyphenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetamide Chemical compound O=C1N(CC(=O)N)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCCC1=CC=CC=C1 SVNWHWFUTFGAIW-UHFFFAOYSA-N 0.000 claims description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 3
241000335423 Blastomyces Species 0.000 claims description 3
241001480037 Microsporum Species 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
101100495911 Arabidopsis thaliana CHR10 gene Proteins 0.000 claims description 2
101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
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 description 2
239000003085 diluting agent Substances 0.000 claims description 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
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 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
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
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
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
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 246
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 218
239000000047 product Substances 0.000 description 76
239000000243 solution Substances 0.000 description 70
238000000034 method Methods 0.000 description 69
239000000843 powder Substances 0.000 description 65
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 64
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 59
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 59
239000003208 petroleum Substances 0.000 description 57
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
235000011152 sodium sulphate Nutrition 0.000 description 32
QEBZGDYGMMSNRY-UHFFFAOYSA-N 2-phenoxy-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N)OC1=CC=CC=C1 QEBZGDYGMMSNRY-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
239000000203 mixture Substances 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 28
229910052938 sodium sulfate Inorganic materials 0.000 description 28
239000012267 brine Substances 0.000 description 26
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
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238000010828 elution Methods 0.000 description 17
229940121375 antifungal agent Drugs 0.000 description 13
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
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238000004090 dissolution Methods 0.000 description 9
IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 8
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
OAOJBMHAQUUUTE-UHFFFAOYSA-N 3-hydroxy-4-(2-phenylethoxy)benzaldehyde Chemical compound OC1=CC(C=O)=CC=C1OCCC1=CC=CC=C1 OAOJBMHAQUUUTE-UHFFFAOYSA-N 0.000 description 6
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 6
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WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
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ABUKMOCUMIPDHV-UHFFFAOYSA-N 2-phenoxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OC1=CC=CC=C1 ABUKMOCUMIPDHV-UHFFFAOYSA-N 0.000 description 5
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238000012360 testing method Methods 0.000 description 5
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 5
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PCYGLFXKCBFGPC-UHFFFAOYSA-N 3,4-Dihydroxy hydroxymethyl benzene Natural products OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-UHFFFAOYSA-N 0.000 description 4
CWMRCRFALIQFHU-UHFFFAOYSA-N 4-hydroxy-3-phenylmethoxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 CWMRCRFALIQFHU-UHFFFAOYSA-N 0.000 description 4
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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229920002498 Beta-glucan Polymers 0.000 description 3
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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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Thiazole And Isothizaole Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

ES01963157T 2000-08-31 2001-08-30 Derivados de bencilideno tiazolidinadionas y su uso como agentes antifungicos. Expired - Lifetime ES2282283T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB0021421		2000-08-31
GBGB0021421.3A GB0021421D0 (en)	2000-08-31	2000-08-31	Compounds

Publications (1)

Publication Number	Publication Date
ES2282283T3 true ES2282283T3 (es)	2007-10-16

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ES01963157T Expired - Lifetime ES2282283T3 (es)	2000-08-31	2001-08-30	Derivados de bencilideno tiazolidinadionas y su uso como agentes antifungicos.

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US (1)	US7105554B2 (2)
EP (1)	EP1313471B1 (2)
JP (1)	JP2004507501A (2)
AT (1)	ATE359073T1 (2)
AU (1)	AU2001284190A1 (2)
DE (1)	DE60127845T2 (2)
ES (1)	ES2282283T3 (2)
GB (1)	GB0021421D0 (2)
WO (1)	WO2002017915A1 (2)

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ATE536347T1 (de)	2008-05-20	2011-12-15	Merck Sharp & Dohme	Effiziente herstellung heterologer proteine unter verwendung von mannosyltransferaseinhibitoren
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KR20140114278A (ko)	2011-02-25	2014-09-26	머크 샤프 앤드 돔 코포레이션	변형된 ｏ-글리코실화를 갖는 단백질의 생산을 위한 효모 균주
CN103797000B (zh) *	2011-07-29	2016-07-06	大正制药株式会社	脒化合物或其盐
WO2014024897A1 (ja) *	2012-08-06	2014-02-13	ＭｅｉｊｉＳｅｉｋａ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
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ES2739280T3 (es)	2013-07-04	2020-01-30	Glykos Finland Oy	Células fúngicas filamentosas deficientes en O-manosiltransferasa y métodos de uso de las mismas
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US10647654B2 (en)	2016-06-24	2020-05-12	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

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2000
- 2000-08-31 GB GBGB0021421.3A patent/GB0021421D0/en not_active Ceased
2001
- 2001-08-30 AU AU2001284190A patent/AU2001284190A1/en not_active Abandoned
- 2001-08-30 ES ES01963157T patent/ES2282283T3/es not_active Expired - Lifetime
- 2001-08-30 WO PCT/GB2001/003862 patent/WO2002017915A1/en not_active Ceased
- 2001-08-30 AT AT01963157T patent/ATE359073T1/de not_active IP Right Cessation
- 2001-08-30 EP EP01963157A patent/EP1313471B1/en not_active Expired - Lifetime
- 2001-08-30 JP JP2002522888A patent/JP2004507501A/ja active Pending
- 2001-08-30 DE DE60127845T patent/DE60127845T2/de not_active Expired - Lifetime
2003
- 2003-02-21 US US10/371,964 patent/US7105554B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US20040006112A1 (en)	2004-01-08
WO2002017915A1 (en)	2002-03-07
EP1313471A1 (en)	2003-05-28
DE60127845T2 (de)	2007-12-20
US7105554B2 (en)	2006-09-12
GB0021421D0 (en)	2000-10-18
AU2001284190A1 (en)	2002-03-13
EP1313471B1 (en)	2007-04-11
DE60127845D1 (de)	2007-05-24
ATE359073T1 (de)	2007-05-15
JP2004507501A (ja)	2004-03-11

Publication	Publication Date	Title
ES2282283T3 (es)	2007-10-16	Derivados de bencilideno tiazolidinadionas y su uso como agentes antifungicos.
ES2320320T3 (es)	2009-05-21	Nuevos compuestos de isoxazol y tiazol y uso de los mismos como farmacos.
ES2267873T3 (es)	2007-03-16	Derivados de 4-aminotiazol, su preparacion y uso como inhibidores de kinasas dependientes de ciclina.
ES2315566T3 (es)	2009-04-01	Tiazolidin-4-onas para inhibir proteinas hyak3.
US9447058B2 (en)	2016-09-20	Substituted 1,3-thiazoles as heat shock transcription factor 1 activators
TWI352084B (en)	2011-11-11	Gsk-3 inhibitors
US12221406B2 (en)	2025-02-11	Compounds as NLRP3 inflammasome inhibitors and compositions and uses thereof
ES2324922T3 (es)	2009-08-19	Derivados de tiazol que tienen actividad inhibidora de vap-1.
BR112012007828B1 (pt)	2021-01-12	compostos inibidores da xantina oxidase, processo para preparar os compostos, e, composição farmacêutica para a inibição da xantina oxidase
ES2353685T3 (es)	2011-03-04	Derivados de tiazolidina y su uso como agente antifúngico.
WO2004092123A2 (en)	2004-10-28	Inhibitors of fungal invasion
US9845319B2 (en)	2017-12-19	Amide substituted thiazoles as modulators of RORyt
TWI592407B (zh)	2017-07-21	飢餓素ｏ－醯基轉移酶抑制劑
US20180312482A1 (en)	2018-11-01	Heterocyclicalkyl derivative compounds as selective histone deacetylase inhibitors and pharmaceutical compositions comprising the same
IL205029A (en)	2014-09-30	Annotated (r) - 4 - (heteroaryl) phenylpropionic and medicinal preparations containing them
CA3030232A1 (en)	2018-01-18	Pyrimidinone derivatives and uses thereof to neutralize the biological activity of chemokines
SK159995A3 (en)	1996-06-05	Novel (1-phenyl-1-heterocyclyl)alkane derivatives and their use as neuroprotective agents
ES2876285T3 (es)	2021-11-12	Derivados de acetamida de 2-(1,2,4-triazol-3-ilsulfanil)-N-1,3,4-tiadiazol-2-ilo que son útiles para el tratamiento de la diabetes
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JP2020513408A (ja)	2020-05-14	老化関連障害を治療するための化合物
JP2001505880A (ja)	2001-05-08	抗微生物活性を有する環状ヘキサペプチド
JP2010520236A (ja)	2010-06-10	リソフィリンアナログとその使用法
EP3423448B1 (en)	2024-12-04	Cannabinoid receptor mediating compounds
US11155521B2 (en)	2021-10-26	Cannabinoid receptor mediating compounds
TW200815324A (en)	2008-04-01	Straight chain amine compound