ES2282283T3 - Derivados de bencilideno tiazolidinadionas y su uso como agentes antifungicos. - Google Patents
Derivados de bencilideno tiazolidinadionas y su uso como agentes antifungicos. Download PDFInfo
- Publication number
- ES2282283T3 ES2282283T3 ES01963157T ES01963157T ES2282283T3 ES 2282283 T3 ES2282283 T3 ES 2282283T3 ES 01963157 T ES01963157 T ES 01963157T ES 01963157 T ES01963157 T ES 01963157T ES 2282283 T3 ES2282283 T3 ES 2282283T3
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- acid
- phenylmethoxy
- methylene
- 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.)
- Expired - Lifetime
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
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- 235000019198 oils Nutrition 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 18
- 229910000024 caesium carbonate Inorganic materials 0.000 description 17
- 238000010828 elution Methods 0.000 description 17
- 229940121375 antifungal agent Drugs 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 241000222122 Candida albicans Species 0.000 description 10
- 229940095731 candida albicans Drugs 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
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- 239000000377 silicon dioxide Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 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
- 239000003429 antifungal agent Substances 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 230000002538 fungal effect Effects 0.000 description 8
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- 239000000725 suspension Substances 0.000 description 8
- 238000007792 addition Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 210000002421 cell wall Anatomy 0.000 description 7
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- 239000006071 cream Substances 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 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
- 239000005695 Ammonium acetate Substances 0.000 description 6
- 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
- 239000004480 active ingredient Substances 0.000 description 6
- 229940043376 ammonium acetate Drugs 0.000 description 6
- 235000019257 ammonium acetate Nutrition 0.000 description 6
- 230000000843 anti-fungal effect Effects 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 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
- 238000004587 chromatography analysis Methods 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
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 4
- 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
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 102100024023 Histone PARylation factor 1 Human genes 0.000 description 4
- 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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- 239000011734 sodium Substances 0.000 description 4
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- 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 3
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- DVFRQYJNNUBERX-UHFFFAOYSA-N 3-(phenoxymethyl)-4-phenylmethoxybenzaldehyde Chemical compound C=1C=CC=CC=1OCC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 DVFRQYJNNUBERX-UHFFFAOYSA-N 0.000 description 3
- GJEDLJSDEZYRQT-UHFFFAOYSA-N 3-hydroxy-4-[(4-methoxyphenyl)methoxy]benzaldehyde Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(C=O)C=C1O GJEDLJSDEZYRQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 229920002498 Beta-glucan Polymers 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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- 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
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- 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
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- 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
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (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)
Applications Claiming Priority (2)
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| GBGB0021421.3A GB0021421D0 (en) | 2000-08-31 | 2000-08-31 | Compounds |
| GB0021421 | 2000-08-31 |
Publications (1)
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|---|---|
| ES2282283T3 true ES2282283T3 (es) | 2007-10-16 |
Family
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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 (OSRAM) |
| EP (1) | EP1313471B1 (OSRAM) |
| JP (1) | JP2004507501A (OSRAM) |
| AT (1) | ATE359073T1 (OSRAM) |
| AU (1) | AU2001284190A1 (OSRAM) |
| DE (1) | DE60127845T2 (OSRAM) |
| ES (1) | ES2282283T3 (OSRAM) |
| GB (1) | GB0021421D0 (OSRAM) |
| WO (1) | WO2002017915A1 (OSRAM) |
Families Citing this family (23)
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| AU2003205907A1 (en) * | 2002-02-23 | 2003-09-09 | Oxford Glycosciences (Uk) Ltd | Thiazolidine antifungal agents |
| GB0204252D0 (en) * | 2002-02-23 | 2002-04-10 | Oxford Glycosciences Uk Ltd | Novel compounds |
| BRPI0507877A (pt) | 2004-03-23 | 2007-07-24 | Pfizer | derivados de formamida, composição farmacêutica, uso dos mesmos e combinação |
| AU2006316838B2 (en) * | 2005-11-15 | 2012-04-12 | Glycofi, Inc | Production of glycoproteins with reduced O-glycosylation |
| US7731106B2 (en) * | 2006-01-04 | 2010-06-08 | 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 |
| EP2263089B1 (en) * | 2008-03-03 | 2015-01-28 | GlycoFi, Inc. | Surface display of recombinant proteins in lower eukaryotes |
| CA2721459A1 (en) | 2008-05-20 | 2009-11-26 | Merck Sharp & Dohme Corp. | Efficient production of heterologous proteins using mannosyl transferase inhibitors |
| 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 |
| CN103764837A (zh) | 2011-02-25 | 2014-04-30 | 默沙东公司 | 用于生产具有修饰的o-糖基化的蛋白的酵母菌株 |
| CA2843383A1 (en) * | 2011-07-29 | 2013-02-07 | Taisho Pharmaceutical Co., Ltd. | Amidine compound or salt thereof |
| 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 |
| HRP20191069T1 (hr) | 2013-07-04 | 2019-11-01 | Glykos Finland Oy | Stanice filamentoznih gljiva s deficijencijom o-manozil transferaze i postupci njihove uporabe |
| 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 |
| US20190307729A1 (en) * | 2016-06-14 | 2019-10-10 | Versitech Limited | Antimicrobial compounds and methods for use thereof |
| CN109476656A (zh) * | 2016-06-24 | 2019-03-15 | 俄亥俄州大学 | 葡萄糖转运抑制剂及使用其的方法 |
| 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 |
| WO2000018746A1 (en) * | 1998-09-30 | 2000-04-06 | Roche Diagnostics Gmbh | Thiazolidine derivatives for the treatment and prevention of metabolic bone disorders |
| WO2000018747A1 (en) * | 1998-09-30 | 2000-04-06 | 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
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2001
- 2001-08-30 JP JP2002522888A patent/JP2004507501A/ja active Pending
- 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 EP EP01963157A patent/EP1313471B1/en not_active Expired - Lifetime
- 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
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2003
- 2003-02-21 US US10/371,964 patent/US7105554B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001284190A1 (en) | 2002-03-13 |
| GB0021421D0 (en) | 2000-10-18 |
| DE60127845D1 (de) | 2007-05-24 |
| US7105554B2 (en) | 2006-09-12 |
| ATE359073T1 (de) | 2007-05-15 |
| US20040006112A1 (en) | 2004-01-08 |
| JP2004507501A (ja) | 2004-03-11 |
| EP1313471A1 (en) | 2003-05-28 |
| WO2002017915A1 (en) | 2002-03-07 |
| EP1313471B1 (en) | 2007-04-11 |
| DE60127845T2 (de) | 2007-12-20 |
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