DE60127845T2 - Benzylidenthiazolidindione und ihre verwendung als antimykotische mittel - Google Patents
Benzylidenthiazolidindione und ihre verwendung als antimykotische mittel Download PDFInfo
- Publication number
- DE60127845T2 DE60127845T2 DE60127845T DE60127845T DE60127845T2 DE 60127845 T2 DE60127845 T2 DE 60127845T2 DE 60127845 T DE60127845 T DE 60127845T DE 60127845 T DE60127845 T DE 60127845T DE 60127845 T2 DE60127845 T2 DE 60127845T2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- phenylmethoxy
- methylene
- oxo
- 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
- 239000003429 antifungal agent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 15
- 208000031888 Mycoses Diseases 0.000 claims abstract description 15
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 15
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 101100516572 Caenorhabditis elegans nhr-8 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 129
- -1 3,4-difluorophenyl Chemical group 0.000 claims description 94
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 93
- 125000005975 2-phenylethyloxy group Chemical group 0.000 claims description 44
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- JGRMXPSUZIYDRR-UHFFFAOYSA-N 2-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)acetic acid Chemical compound OC(=O)CN1C(=O)CSC1=S JGRMXPSUZIYDRR-UHFFFAOYSA-N 0.000 claims description 10
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 208000015181 infectious disease Diseases 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 238000011321 prophylaxis Methods 0.000 claims description 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
- 241000228197 Aspergillus flavus Species 0.000 claims description 4
- 241001225321 Aspergillus fumigatus Species 0.000 claims description 4
- 241000335423 Blastomyces 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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 241001480037 Microsporum Species 0.000 claims description 4
- 241001537205 Paracoccidioides Species 0.000 claims description 4
- 241000223238 Trichophyton Species 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
- 229940091771 aspergillus fumigatus Drugs 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 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 description 2
- 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 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
- AOAROSLFYLNGCD-RUZDIDTESA-N 2-[4-oxo-5-[[4-(2-phenylethoxy)-3-[(1r)-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=C1O[C@H](C=2C=CC=CC=2)C(F)(F)F)=CC=C1OCCC1=CC=CC=C1 AOAROSLFYLNGCD-RUZDIDTESA-N 0.000 claims description 2
- AOAROSLFYLNGCD-VWLOTQADSA-N 2-[4-oxo-5-[[4-(2-phenylethoxy)-3-[(1s)-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=C1O[C@@H](C=2C=CC=CC=2)C(F)(F)F)=CC=C1OCCC1=CC=CC=C1 AOAROSLFYLNGCD-VWLOTQADSA-N 0.000 claims description 2
- 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 2
- LHYRKNFTTKMDNQ-DWXRJYCRSA-N 2-[4-oxo-5-[[4-[(2s)-2-phenylpropoxy]-3-[(1s)-2,2,2-trifluoro-1-phenylethoxy]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)O[C@@H](C=2C=CC=CC=2)C(F)(F)F)=CC=C1C=C1SC(=S)N(CC(O)=O)C1=O LHYRKNFTTKMDNQ-DWXRJYCRSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000005865 C2-C10alkynyl 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
- 239000003937 drug carrier Substances 0.000 claims description 2
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- 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 2
- 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 1
- LHYRKNFTTKMDNQ-QYBDOPJKSA-N 2-[4-oxo-5-[[4-[(2r)-2-phenylpropoxy]-3-[(1s)-2,2,2-trifluoro-1-phenylethoxy]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)O[C@@H](C=2C=CC=CC=2)C(F)(F)F)=CC=C1C=C1SC(=S)N(CC(O)=O)C1=O LHYRKNFTTKMDNQ-QYBDOPJKSA-N 0.000 claims 1
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- 238000005259 measurement Methods 0.000 description 1
- AMYIBYTXYMGLMV-QRPNPIFTSA-N methane (2R)-2-phenylpropane-1-sulfonic acid Chemical compound C1(=CC=CC=C1)[C@H](CS(=O)(=O)O)C.C AMYIBYTXYMGLMV-QRPNPIFTSA-N 0.000 description 1
- AMYIBYTXYMGLMV-DDWIOCJRSA-N methane (2S)-2-phenylpropane-1-sulfonic acid Chemical compound C1(=CC=CC=C1)[C@@H](CS(=O)(=O)O)C.C AMYIBYTXYMGLMV-DDWIOCJRSA-N 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
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
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- 239000012452 mother liquor Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 235000010460 mustard Nutrition 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
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- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
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- WWJFFVUVFNBJTN-UHFFFAOYSA-N neopolyoxin C Natural products C=1C=C(O)C=NC=1C(O)C(C)C(N)C(=O)NC(C(O)=O)C(C(C1O)O)OC1N1C=CC(=O)NC1=O WWJFFVUVFNBJTN-UHFFFAOYSA-N 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- WWJFFVUVFNBJTN-VHDFTHOZSA-N nikkomycin Z Chemical compound N1([C@@H]2O[C@@H]([C@H]([C@H]2O)O)[C@H](NC(=O)[C@@H](N)[C@H](C)[C@H](O)C=2N=CC(O)=CC=2)C(O)=O)C=CC(=O)NC1=O WWJFFVUVFNBJTN-VHDFTHOZSA-N 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
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
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- 230000001717 pathogenic effect Effects 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
- 239000011505 plaster Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000036573 scar formation Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003548 thiazolidines Chemical class 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
- 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
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0021421 | 2000-08-31 | ||
| 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 |
|---|---|
| DE60127845D1 DE60127845D1 (de) | 2007-05-24 |
| DE60127845T2 true DE60127845T2 (de) | 2007-12-20 |
Family
ID=9898616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60127845T Expired - Lifetime DE60127845T2 (de) | 2000-08-31 | 2001-08-30 | Benzylidenthiazolidindione und ihre verwendung als antimykotische mittel |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7105554B2 (https=) |
| EP (1) | EP1313471B1 (https=) |
| JP (1) | JP2004507501A (https=) |
| AT (1) | ATE359073T1 (https=) |
| AU (1) | AU2001284190A1 (https=) |
| DE (1) | DE60127845T2 (https=) |
| ES (1) | ES2282283T3 (https=) |
| GB (1) | GB0021421D0 (https=) |
| WO (1) | WO2002017915A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| EP1730103B1 (en) | 2004-03-23 | 2010-05-26 | Pfizer Limited | 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 |
| CA2715212A1 (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 |
| CA2733567A1 (en) | 2008-08-12 | 2010-02-18 | Glycofi, Inc. | Improved vectors and yeast strains for protein production: ca2+ atpase overexpression |
| 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 | 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 |
| 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 |
| SG11201700446XA (en) | 2014-07-21 | 2017-02-27 | Glykos Finland Oy | Production of glycoproteins with mammalian-like n-glycans in filamentous fungi |
| CN109414432B (zh) * | 2016-06-14 | 2022-03-08 | 港大科桥有限公司 | 抗微生物化合物及其使用方法 |
| 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 |
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 |
| 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 |
| JPH08109174A (ja) * | 1994-10-07 | 1996-04-30 | Torii Yakuhin Kk | チアゾリジン−２−オン誘導体 |
| AU6331099A (en) * | 1998-09-30 | 2000-04-17 | Roche Diagnostics Gmbh | Thiazolidine derivatives for the treatment and prevention of metabolic bone disorders |
| EP1117655A1 (en) * | 1998-09-30 | 2001-07-25 | Angelika Esswein | 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 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 |
|---|---|
| ES2282283T3 (es) | 2007-10-16 |
| US20040006112A1 (en) | 2004-01-08 |
| WO2002017915A1 (en) | 2002-03-07 |
| EP1313471A1 (en) | 2003-05-28 |
| 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 |
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| 8364 | No opposition during term of opposition |