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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 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
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 288
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 223
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 180
- 239000000243 solution Substances 0.000 description 78
- 239000000047 product Substances 0.000 description 74
- 238000000034 method Methods 0.000 description 68
- 239000000843 powder Substances 0.000 description 66
- 239000003208 petroleum Substances 0.000 description 63
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 60
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 34
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 229910052938 sodium sulfate Inorganic materials 0.000 description 33
- 235000011152 sodium sulphate Nutrition 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- 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 29
- 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
- 239000000741 silica gel Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- 238000004587 chromatography analysis Methods 0.000 description 20
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- 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 18
- 239000000203 mixture Substances 0.000 description 18
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 15
- 238000010828 elution Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000003921 oil Substances 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
- 235000019198 oils Nutrition 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 241000894007 species Species 0.000 description 9
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 8
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 8
- 101150065749 Churc1 gene Proteins 0.000 description 8
- 102100038239 Protein Churchill Human genes 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 8
- 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 7
- 239000004480 active ingredient Substances 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 229940121375 antifungal agent Drugs 0.000 description 7
- 210000002421 cell wall Anatomy 0.000 description 7
- 230000002538 fungal effect Effects 0.000 description 7
- BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Natural products O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000725 suspension Substances 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
- 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
- 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
- 230000015572 biosynthetic process Effects 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- WHBNKGILKCASDH-UHFFFAOYSA-N 2-(2,4-dioxo-1,3-thiazolidin-3-yl)acetic acid Chemical compound OC(=O)CN1C(=O)CSC1=O WHBNKGILKCASDH-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 5
- 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 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
- 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
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 230000001857 anti-mycotic effect Effects 0.000 description 4
- 239000002543 antimycotic Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 108010005335 mannoproteins Proteins 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- 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 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
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 3
- 229920002498 Beta-glucan Polymers 0.000 description 3
- 229920002101 Chitin Polymers 0.000 description 3
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 3
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 206010065764 Mucosal infection Diseases 0.000 description 3
- 208000007027 Oral Candidiasis Diseases 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 201000007096 Vulvovaginal Candidiasis Diseases 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 238000011200 topical administration Methods 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- FYGDTMLNYKFZSV-URKRLVJHSA-N (2s,3r,4s,5s,6r)-2-[(2r,4r,5r,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2r,4r,5r,6s)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1[C@@H](CO)O[C@@H](OC2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-URKRLVJHSA-N 0.000 description 2
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
- 125000005976 1-phenylethyloxy group Chemical group 0.000 description 2
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 2
- CCIQRGLWXGAUEB-UHFFFAOYSA-N 3-(1-phenylethoxy)-4-(2-phenylethoxy)benzaldehyde Chemical compound C=1C=CC=CC=1C(C)OC1=CC(C=O)=CC=C1OCCC1=CC=CC=C1 CCIQRGLWXGAUEB-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- FYNGPYHJLQRZEH-UHFFFAOYSA-N 3-(hydroxymethyl)-4-(2-phenylethoxy)benzaldehyde Chemical compound OCC1=CC(C=O)=CC=C1OCCC1=CC=CC=C1 FYNGPYHJLQRZEH-UHFFFAOYSA-N 0.000 description 2
- WPEUHXUMNIBPKH-UHFFFAOYSA-N 3-(phenoxymethyl)-4-(2-phenylethoxy)benzaldehyde Chemical compound C=1C=CC=CC=1OCC1=CC(C=O)=CC=C1OCCC1=CC=CC=C1 WPEUHXUMNIBPKH-UHFFFAOYSA-N 0.000 description 2
- HUNGEAFDVLSPAM-UHFFFAOYSA-N 3-hydroxy-4-phenylmethoxybenzaldehyde Chemical compound OC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 HUNGEAFDVLSPAM-UHFFFAOYSA-N 0.000 description 2
- QEICZEGWCSHJNS-UHFFFAOYSA-N 3-phenylmethoxy-4-[[4-(trifluoromethyl)phenyl]methoxy]benzaldehyde Chemical compound C1=CC(C(F)(F)F)=CC=C1COC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 QEICZEGWCSHJNS-UHFFFAOYSA-N 0.000 description 2
- OKFUIDSZUWWIGG-UHFFFAOYSA-N 4-(2,2,3,3,3-pentafluoropropoxy)-3-phenylmethoxybenzaldehyde Chemical compound FC(F)(F)C(F)(F)COC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 OKFUIDSZUWWIGG-UHFFFAOYSA-N 0.000 description 2
- HYIMLCBUZXLKNR-UHFFFAOYSA-N 4-(2-phenylethoxy)-3-(2,2,2-trifluoro-1-phenylethoxy)benzaldehyde Chemical compound C=1C=CC=CC=1C(C(F)(F)F)OC1=CC(C=O)=CC=C1OCCC1=CC=CC=C1 HYIMLCBUZXLKNR-UHFFFAOYSA-N 0.000 description 2
- NXKDHOLJDMFZSJ-UHFFFAOYSA-N 4-(2-phenylethoxy)-3-(pyridin-2-ylmethoxy)benzaldehyde Chemical compound C=1C=CC=NC=1COC1=CC(C=O)=CC=C1OCCC1=CC=CC=C1 NXKDHOLJDMFZSJ-UHFFFAOYSA-N 0.000 description 2
- AYWMXTFLDCNODY-QFIPXVFZSA-N 4-[(4-methoxyphenyl)methoxy]-3-[(1s)-2,2,2-trifluoro-1-phenylethoxy]benzaldehyde Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(C=O)C=C1O[C@H](C(F)(F)F)C1=CC=CC=C1 AYWMXTFLDCNODY-QFIPXVFZSA-N 0.000 description 2
- IOTRGNBQFDQYQI-UHFFFAOYSA-N 4-[(4-methoxyphenyl)methoxy]-3-phenylmethoxybenzaldehyde Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 IOTRGNBQFDQYQI-UHFFFAOYSA-N 0.000 description 2
- XZJOBMNLRNUGDE-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)ethoxy]-3-phenylmethoxybenzaldehyde Chemical compound C1=CC(Cl)=CC=C1CCOC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 XZJOBMNLRNUGDE-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- AAHYBQDGJJEWKD-AWEZNQCLSA-N 4-hydroxy-3-[(1s)-2,2,2-trifluoro-1-phenylethoxy]benzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O[C@H](C(F)(F)F)C1=CC=CC=C1 AAHYBQDGJJEWKD-AWEZNQCLSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 108010049047 Echinocandins Proteins 0.000 description 2
- 241000400611 Eucalyptus deanei Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 102000006722 Mannosyltransferases Human genes 0.000 description 2
- 108010087568 Mannosyltransferases Proteins 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 101001123538 Nicotiana tabacum Putrescine N-methyltransferase 1 Proteins 0.000 description 2
- 0 OC(CN(C(C(S1)=C[C@]2C=C(*Cc3ccccc3)C(OCc(cc3)ccc3OC(F)(F)F)=CC2)=O)C1=S)=O Chemical compound OC(CN(C(C(S1)=C[C@]2C=C(*Cc3ccccc3)C(OCc(cc3)ccc3OC(F)(F)F)=CC2)=O)C1=S)=O 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 2
- 239000004473 Threonine Substances 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- IIMJORKPQQXZHC-UHFFFAOYSA-N [5-formyl-2-(2-phenylethoxy)phenyl]methyl methanesulfonate Chemical compound CS(=O)(=O)OCC1=CC(C=O)=CC=C1OCCC1=CC=CC=C1 IIMJORKPQQXZHC-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- 150000003935 benzaldehydes Chemical class 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000005621 mannosylation reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- NHFBYYMNJUMVOT-UHFFFAOYSA-N methyl 2-bromo-2-phenylacetate Chemical compound COC(=O)C(Br)C1=CC=CC=C1 NHFBYYMNJUMVOT-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 101150092906 pmt1 gene Proteins 0.000 description 2
- 150000004291 polyenes Chemical class 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 210000003491 skin Anatomy 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- GQHFCGULTKNUQX-UHFFFAOYSA-N (2,2,2-trifluoro-1-phenylethyl) trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC(C(F)(F)F)C1=CC=CC=C1 GQHFCGULTKNUQX-UHFFFAOYSA-N 0.000 description 1
- NPZZVZUWMKFFPF-UHFFFAOYSA-N (2-bromo-2-phenylethyl) acetate Chemical compound CC(=O)OCC(Br)C1=CC=CC=C1 NPZZVZUWMKFFPF-UHFFFAOYSA-N 0.000 description 1
- LDDMACCNBZAMSG-BDVNFPICSA-N (2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal Chemical compound CN[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO LDDMACCNBZAMSG-BDVNFPICSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- IKSNDOVDVVPSMA-UHFFFAOYSA-N 1-(bromomethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(CBr)C=C1 IKSNDOVDVVPSMA-UHFFFAOYSA-N 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 description 1
- PSQZJKGXDGNDFP-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)(F)F PSQZJKGXDGNDFP-UHFFFAOYSA-N 0.000 description 1
- KPWPXZKNQFZFMF-UHFFFAOYSA-N 2-(4,5-dioxo-2-sulfanylidene-1,3-thiazolidin-3-yl)acetic acid Chemical compound OC(=O)CN1C(=S)SC(=O)C1=O KPWPXZKNQFZFMF-UHFFFAOYSA-N 0.000 description 1
- OWHCTMNLMFBZHN-UHFFFAOYSA-N 2-(5-methylidene-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)acetic acid Chemical compound OC(=O)CN1C(=S)SC(=C)C1=O OWHCTMNLMFBZHN-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- DGGBSOBIYGYECX-UHFFFAOYSA-N 2-[4-oxo-2-sulfanylidene-5-[[3,4,5-tris(phenylmethoxy)phenyl]methylidene]-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(OCC=2C=CC=CC=2)=C1OCC1=CC=CC=C1 DGGBSOBIYGYECX-UHFFFAOYSA-N 0.000 description 1
- UOUYKRHRZOBMCO-UHFFFAOYSA-N 2-[4-oxo-5-[(4-pentoxy-3-phenylmethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound C1=C(OCC=2C=CC=CC=2)C(OCCCCC)=CC=C1C=C1SC(=S)N(CC(O)=O)C1=O UOUYKRHRZOBMCO-UHFFFAOYSA-N 0.000 description 1
- DQEAQMVSHGBDMM-UHFFFAOYSA-N 2-[4-oxo-5-[[3-phenylmethoxy-4-(pyridin-2-ylmethoxy)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=N1 DQEAQMVSHGBDMM-UHFFFAOYSA-N 0.000 description 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 description 1
- XPEVTLJZABKDHG-UHFFFAOYSA-N 2-[5-[(4-methoxy-3-phenylmethoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound C1=C(OCC=2C=CC=CC=2)C(OC)=CC=C1C=C1SC(=S)N(CC(O)=O)C1=O XPEVTLJZABKDHG-UHFFFAOYSA-N 0.000 description 1
- UNLOPKZKGWMHGD-UHFFFAOYSA-N 2-[5-[1-(3-methoxy-4-phenylmethoxyphenyl)ethylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound COC1=CC(C(C)=C2C(N(CC(O)=O)C(=S)S2)=O)=CC=C1OCC1=CC=CC=C1 UNLOPKZKGWMHGD-UHFFFAOYSA-N 0.000 description 1
- YWTZXQOVHMLSGN-UHFFFAOYSA-N 2-[5-[[3,4-bis(phenylmethoxy)phenyl]methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=O)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCC1=CC=CC=C1 YWTZXQOVHMLSGN-UHFFFAOYSA-N 0.000 description 1
- RAYQPKALIZGABL-UHFFFAOYSA-N 2-[5-[[3,4-bis(phenylmethoxy)phenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid Chemical compound S=C1SC(=CC=2C=C(OCC=3C=CC=CC=3)C(OCC=3C=CC=CC=3)=CC=2)C(=O)N1C(C(=O)O)CC1=CC=CC=C1 RAYQPKALIZGABL-UHFFFAOYSA-N 0.000 description 1
- OOENNZREZDKUHB-UHFFFAOYSA-N 2-[5-[[3,4-bis(phenylmethoxy)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=CC=2)=CC=C1OCC1=CC=CC=C1 OOENNZREZDKUHB-UHFFFAOYSA-N 0.000 description 1
- XNDIXYSEEBIMKC-UHFFFAOYSA-N 2-[5-[[3,4-bis(phenylmethoxy)phenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid Chemical compound O=C1N(C(C)C(O)=O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCC1=CC=CC=C1 XNDIXYSEEBIMKC-UHFFFAOYSA-N 0.000 description 1
- BHVBBVSEXONYKM-UHFFFAOYSA-N 2-[5-[[3,4-bis[(4-methoxyphenyl)methoxy]phenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1COC(C(=C1)OCC=2C=CC(OC)=CC=2)=CC=C1C=C1C(=O)N(CC(O)=O)C(=S)S1 BHVBBVSEXONYKM-UHFFFAOYSA-N 0.000 description 1
- HNTNFSGQGSEFGM-UHFFFAOYSA-N 2-[5-[[3-[(4-methylsulfonylphenyl)methoxy]-4-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1COC1=CC(C=C2C(N(CC(O)=O)C(=S)S2)=O)=CC=C1OCC1=CC=CC=C1 HNTNFSGQGSEFGM-UHFFFAOYSA-N 0.000 description 1
- RYINIELRRQTSQL-UHFFFAOYSA-N 2-[5-[[4-(2-cyclohexylethoxy)-3-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCCC1CCCCC1 RYINIELRRQTSQL-UHFFFAOYSA-N 0.000 description 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 description 1
- ICNYEXXENSBATD-UHFFFAOYSA-N 2-[5-[[4-[(3,4-difluorophenyl)methoxy]-3-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCC1=CC=C(F)C(F)=C1 ICNYEXXENSBATD-UHFFFAOYSA-N 0.000 description 1
- KXXVXDYWAYXDTO-UHFFFAOYSA-N 2-[5-[[4-[(4-methylsulfonylphenyl)methoxy]-3-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)C)=CC=C1COC(C(=C1)OCC=2C=CC=CC=2)=CC=C1C=C1C(=O)N(CC(O)=O)C(=S)S1 KXXVXDYWAYXDTO-UHFFFAOYSA-N 0.000 description 1
- SSKLGZLYOABIDO-UHFFFAOYSA-N 2-[5-[[4-[2-(4-chlorophenyl)ethoxy]-3-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1=CC(C=C1OCC=2C=CC=CC=2)=CC=C1OCCC1=CC=C(Cl)C=C1 SSKLGZLYOABIDO-UHFFFAOYSA-N 0.000 description 1
- QEZYNSXJLFISBS-UHFFFAOYSA-N 2-methoxy-3-phenylmethoxybenzaldehyde Chemical compound C1=CC=C(C=O)C(OC)=C1OCC1=CC=CC=C1 QEZYNSXJLFISBS-UHFFFAOYSA-N 0.000 description 1
- FTZQGKNKPLTWCJ-UHFFFAOYSA-N 2-methoxy-4-(4-methylsulfonylphenyl)-3-phenylmethoxybenzaldehyde Chemical compound COc1c(C=O)ccc(c1OCc1ccccc1)-c1ccc(cc1)S(C)(=O)=O FTZQGKNKPLTWCJ-UHFFFAOYSA-N 0.000 description 1
- ABEPSQZVZNRXCY-UHFFFAOYSA-N 3,4,5-tris(phenylmethoxy)benzaldehyde Chemical compound C=1C=CC=CC=1COC=1C(OCC=2C=CC=CC=2)=CC(C=O)=CC=1OCC1=CC=CC=C1 ABEPSQZVZNRXCY-UHFFFAOYSA-N 0.000 description 1
- XDDLXZHBWVFPRG-UHFFFAOYSA-N 3,4-bis(phenylmethoxy)benzaldehyde Chemical compound C=1C=CC=CC=1COC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 XDDLXZHBWVFPRG-UHFFFAOYSA-N 0.000 description 1
- ZBRJSNLMWMYQBE-UHFFFAOYSA-N 3,4-bis[(2,4-difluorophenyl)methoxy]benzaldehyde Chemical compound FC1=CC(F)=CC=C1COC1=CC=C(C=O)C=C1OCC1=CC=C(F)C=C1F ZBRJSNLMWMYQBE-UHFFFAOYSA-N 0.000 description 1
- KBKYQZRICFCNQZ-UHFFFAOYSA-N 3,4-bis[(3-methoxyphenyl)methoxy]benzaldehyde Chemical compound COC1=CC=CC(COC=2C(=CC(C=O)=CC=2)OCC=2C=C(OC)C=CC=2)=C1 KBKYQZRICFCNQZ-UHFFFAOYSA-N 0.000 description 1
- SXMNWKBBBYQNGR-UHFFFAOYSA-N 3,4-bis[(4-fluorophenyl)methoxy]benzaldehyde Chemical compound C1=CC(F)=CC=C1COC1=CC=C(C=O)C=C1OCC1=CC=C(F)C=C1 SXMNWKBBBYQNGR-UHFFFAOYSA-N 0.000 description 1
- DXDYEQZZACUTLH-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-2-methoxy-4-phenylmethoxybenzaldehyde Chemical compound COc1c(C=O)ccc(OCc2ccccc2)c1-c1ccc(F)c(F)c1 DXDYEQZZACUTLH-UHFFFAOYSA-N 0.000 description 1
- OYTAYRZFBZUFGJ-UHFFFAOYSA-N 3-(hydroxymethyl)-4-phenylmethoxybenzaldehyde Chemical compound OCC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 OYTAYRZFBZUFGJ-UHFFFAOYSA-N 0.000 description 1
- QCLOBUFKSPFPBH-UHFFFAOYSA-N 3-[(4-methylsulfonylphenyl)methoxy]-4-phenylmethoxybenzaldehyde Chemical compound C1=CC(S(=O)(=O)C)=CC=C1COC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 QCLOBUFKSPFPBH-UHFFFAOYSA-N 0.000 description 1
- CUQKDYHGMOYBRE-UHFFFAOYSA-N 3-hydroxy-4-pentoxybenzaldehyde Chemical compound CCCCCOC1=CC=C(C=O)C=C1O CUQKDYHGMOYBRE-UHFFFAOYSA-N 0.000 description 1
- MXZSPCLJEUPSHP-UHFFFAOYSA-N 3-phenylmethoxy-4-(pyridin-2-ylmethoxy)benzaldehyde Chemical compound C=1C=CC=CC=1COC1=CC(C=O)=CC=C1OCC1=CC=CC=N1 MXZSPCLJEUPSHP-UHFFFAOYSA-N 0.000 description 1
- VLWDESUHXBSPDI-GOSISDBHSA-N 3-phenylmethoxy-4-[(2s)-2-phenylpropoxy]benzaldehyde Chemical compound C([C@@H](C)C=1C=CC=CC=1)OC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 VLWDESUHXBSPDI-GOSISDBHSA-N 0.000 description 1
- KAXYYFIFTLUGSH-UHFFFAOYSA-N 3-phenylmethoxy-4-[[3-(trifluoromethyl)phenyl]methoxy]benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(COC=2C(=CC(C=O)=CC=2)OCC=2C=CC=CC=2)=C1 KAXYYFIFTLUGSH-UHFFFAOYSA-N 0.000 description 1
- FKDUDJQJJLXANY-UHFFFAOYSA-N 3-phenylmethoxy-4-[[4-(trifluoromethoxy)phenyl]methoxy]benzaldehyde Chemical compound C1=CC(OC(F)(F)F)=CC=C1COC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 FKDUDJQJJLXANY-UHFFFAOYSA-N 0.000 description 1
- UJCPKOIVAVYZMS-UHFFFAOYSA-N 4-(2,4-difluorophenyl)-2-methoxy-3-phenylmethoxybenzaldehyde Chemical compound COc1c(C=O)ccc(c1OCc1ccccc1)-c1ccc(F)cc1F UJCPKOIVAVYZMS-UHFFFAOYSA-N 0.000 description 1
- LTBMVIUURINDRI-UHFFFAOYSA-N 4-(2-cyclohexylethoxy)-3-phenylmethoxybenzaldehyde Chemical compound C=1C=CC=CC=1COC1=CC(C=O)=CC=C1OCCC1CCCCC1 LTBMVIUURINDRI-UHFFFAOYSA-N 0.000 description 1
- HYIMLCBUZXLKNR-JOCHJYFZSA-N 4-(2-phenylethoxy)-3-[(1r)-2,2,2-trifluoro-1-phenylethoxy]benzaldehyde Chemical compound O([C@@H](C(F)(F)F)C=1C=CC=CC=1)C1=CC(C=O)=CC=C1OCCC1=CC=CC=C1 HYIMLCBUZXLKNR-JOCHJYFZSA-N 0.000 description 1
- HYIMLCBUZXLKNR-QFIPXVFZSA-N 4-(2-phenylethoxy)-3-[(1s)-2,2,2-trifluoro-1-phenylethoxy]benzaldehyde Chemical compound O([C@H](C(F)(F)F)C=1C=CC=CC=1)C1=CC(C=O)=CC=C1OCCC1=CC=CC=C1 HYIMLCBUZXLKNR-QFIPXVFZSA-N 0.000 description 1
- GOUIRIFORVFVOM-UHFFFAOYSA-N 4-(2-phenylethoxy)-3-phenylmethoxybenzaldehyde Chemical compound C=1C=CC=CC=1COC1=CC(C=O)=CC=C1OCCC1=CC=CC=C1 GOUIRIFORVFVOM-UHFFFAOYSA-N 0.000 description 1
- UJEQNYBFMWNLMX-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-2-methoxy-3-phenylmethoxybenzaldehyde Chemical compound COc1c(C=O)ccc(c1OCc1ccccc1)-c1ccc(F)c(F)c1 UJEQNYBFMWNLMX-UHFFFAOYSA-N 0.000 description 1
- QYAQPWFKNCNYAC-HXOBKFHXSA-N 4-[(2s)-2-phenylpropoxy]-3-[(1s)-2,2,2-trifluoro-1-phenylethoxy]benzaldehyde Chemical compound C1([C@H](OC2=CC(C=O)=CC=C2OC[C@@H](C)C=2C=CC=CC=2)C(F)(F)F)=CC=CC=C1 QYAQPWFKNCNYAC-HXOBKFHXSA-N 0.000 description 1
- PPFIKTPBIVSEHJ-UHFFFAOYSA-N 4-[(4-chlorophenyl)methoxy]-3-phenylmethoxybenzaldehyde Chemical compound C1=CC(Cl)=CC=C1COC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 PPFIKTPBIVSEHJ-UHFFFAOYSA-N 0.000 description 1
- LHGZGZHGOPGTBK-UHFFFAOYSA-N 4-[(4-methylphenyl)methoxy]-3-phenylmethoxybenzaldehyde Chemical compound C1=CC(C)=CC=C1COC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 LHGZGZHGOPGTBK-UHFFFAOYSA-N 0.000 description 1
- KREKFFLJMWUKSD-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)ethoxy]-3-phenylmethoxybenzaldehyde Chemical compound C1=CC(F)=CC=C1CCOC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 KREKFFLJMWUKSD-UHFFFAOYSA-N 0.000 description 1
- OSBMYRWPLSONHG-GMUIIQOCSA-N 4-[2-(4-fluorophenyl)ethoxy]-3-phenylmethoxybenzaldehyde;3-phenylmethoxy-4-[(2s)-2-phenylpropoxy]benzaldehyde Chemical compound C([C@@H](C)C=1C=CC=CC=1)OC1=CC=C(C=O)C=C1OCC1=CC=CC=C1.C1=CC(F)=CC=C1CCOC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 OSBMYRWPLSONHG-GMUIIQOCSA-N 0.000 description 1
- 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 description 1
- SCXZNYRQOPBUTM-UHFFFAOYSA-N 4-hydroxy-3-(hydroxymethyl)benzaldehyde Chemical compound OCC1=CC(C=O)=CC=C1O SCXZNYRQOPBUTM-UHFFFAOYSA-N 0.000 description 1
- VQVQZFHUXRSRBZ-UHFFFAOYSA-N 4-methoxy-3-phenylmethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 VQVQZFHUXRSRBZ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- BIYJKFUIXZMNQV-UHFFFAOYSA-N 4-pentoxy-3-phenylmethoxybenzaldehyde Chemical compound CCCCCOC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 BIYJKFUIXZMNQV-UHFFFAOYSA-N 0.000 description 1
- XNQNPLQYHSGQDQ-UHFFFAOYSA-N 4-phenylmethoxy-3-(pyridin-2-ylmethoxy)benzaldehyde Chemical compound C=1C=CC=NC=1COC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 XNQNPLQYHSGQDQ-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 101100495911 Arabidopsis thaliana CHR10 gene Proteins 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- ODEFVJRJSWGVCY-ZXVVBBHZSA-N CCCN(CCC)C(C(c1ccccc1)OC(C1)C(OCc2ccccc2)=CC=C1/C=C(\CC(N1CC(N=O)=O)=O)/C1=O)=O Chemical compound CCCN(CCC)C(C(c1ccccc1)OC(C1)C(OCc2ccccc2)=CC=C1/C=C(\CC(N1CC(N=O)=O)=O)/C1=O)=O ODEFVJRJSWGVCY-ZXVVBBHZSA-N 0.000 description 1
- XPEVTLJZABKDHG-YVLHZVERSA-N COc(ccc(/C=C(/C(N1CC(O)=O)=O)\SC1=S)c1)c1OCc1ccccc1 Chemical compound COc(ccc(/C=C(/C(N1CC(O)=O)=O)\SC1=S)c1)c1OCc1ccccc1 XPEVTLJZABKDHG-YVLHZVERSA-N 0.000 description 1
- 101001123543 Caenorhabditis elegans Phosphoethanolamine N-methyltransferase 1 Proteins 0.000 description 1
- 101100408676 Caenorhabditis elegans pmt-1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KSRYSBSIVHFTPO-UHFFFAOYSA-N Cc1ccc(CCOc2ccc(C=O)cc2OCc2ccccc2)cc1 Chemical compound Cc1ccc(CCOc2ccc(C=O)cc2OCc2ccccc2)cc1 KSRYSBSIVHFTPO-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 229920001503 Glucan Polymers 0.000 description 1
- 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 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 108010028921 Lipopeptides Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 108010052285 Membrane Proteins Proteins 0.000 description 1
- 102000018697 Membrane Proteins Human genes 0.000 description 1
- 208000029725 Metabolic bone disease Diseases 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 101100046790 Mus musculus Trappc2 gene Proteins 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- DQXXUAYZVQKFLQ-UHFFFAOYSA-N OC(C(c1ccccc1)Oc1cc(C=O)ccc1OCc1ccccc1)=O Chemical compound OC(C(c1ccccc1)Oc1cc(C=O)ccc1OCc1ccccc1)=O DQXXUAYZVQKFLQ-UHFFFAOYSA-N 0.000 description 1
- XTFYPIJXZLFEAR-NYAPKIOYSA-N OC(CN(C(/C(/S1)=C/c(cc2OCc(c(F)c3)ccc3F)ccc2OCc(ccc(F)c2)c2F)=O)C1=S)=O Chemical compound OC(CN(C(/C(/S1)=C/c(cc2OCc(c(F)c3)ccc3F)ccc2OCc(ccc(F)c2)c2F)=O)C1=S)=O XTFYPIJXZLFEAR-NYAPKIOYSA-N 0.000 description 1
- ZBURNDZUTYZCKH-KSEXSDGBSA-N OC(CN(C(/C(/S1)=C/c(cc2OCc3ccccc3)ccc2OCc(ccc(F)c2)c2F)=O)C1=S)=O Chemical compound OC(CN(C(/C(/S1)=C/c(cc2OCc3ccccc3)ccc2OCc(ccc(F)c2)c2F)=O)C1=S)=O ZBURNDZUTYZCKH-KSEXSDGBSA-N 0.000 description 1
- 208000001388 Opportunistic Infections Diseases 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- 101100241858 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) OAC1 gene Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- GQHFCGULTKNUQX-SSDOTTSWSA-N [(1r)-2,2,2-trifluoro-1-phenylethyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)O[C@@H](C(F)(F)F)C1=CC=CC=C1 GQHFCGULTKNUQX-SSDOTTSWSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 125000000613 asparagine group Chemical group N[C@@H](CC(N)=O)C(=O)* 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 239000008309 hydrophilic cream Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 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
- 238000002156 mixing Methods 0.000 description 1
- 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
- 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
- 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
- 239000002245 particle Substances 0.000 description 1
- 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
- 230000003442 weekly effect Effects 0.000 description 1
- 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)
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0021421.3A GB0021421D0 (en) | 2000-08-31 | 2000-08-31 | Compounds |
| GB0021421 | 2000-08-31 | ||
| 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 (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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
-
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
-
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 |
| ES2282283T3 (es) | 2007-10-16 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60127845T2 (de) | Benzylidenthiazolidindione und ihre verwendung als antimykotische mittel | |
| DE69835241T2 (de) | 4-Aminothiazol Derivate, deren Herstellung und deren Verwendung als Inhibitoren Cyclin-abhängiger Kinasen | |
| DE60002193T2 (de) | Metalloprotease inhibitoren | |
| EP0229623A2 (de) | Diarylalkyl-substituierte Alkylamine, Verfahren zu ihrer Herstellung, ihre Verwendung sowie sie enthaltende Arzneimittel | |
| DE19728996A1 (de) | Triazolverbindungen und deren Verwendung | |
| DD233374A5 (de) | Verfahren zur herstellung von 2-(n-subst.-guanidino)-4-heteroarylthiazole | |
| DE69222459T2 (de) | Thiazolidindionderivate, ihre Herstellung und Anwendung | |
| DE2914491A1 (de) | 4-(chinolinylaminophenyl)sulfonylpiperazine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE1965264A1 (de) | Pyrazinoylsulfamide und Verfahren zu ihrer Herstellung | |
| JP2004509121A (ja) | チアゾリジン誘導体および抗真菌剤としてのその使用 | |
| DE102005028845A1 (de) | Substituierte Heterocyclen, ihre Verwendung als Medikament sowie enthaltende pharmazeutische Zubereitungen | |
| DE69614407T2 (de) | Pharmazeutische zusammensetzungen | |
| DE69105859T2 (de) | Thioharnstoffderivate und sie enthaltendes antimikrobielles Mittel und sie enthaltendes Mittel gegen Magengeschwüre. | |
| JPS6330308B2 (OSRAM) | ||
| DE69406853T2 (de) | Alpha Aminosäurederivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE3923675A1 (de) | Amonoalkylsubstituierte 2-aminothiazole und diese enthaltende therapeutische mittel | |
| DE1900974B2 (de) | 2,6-Diphenyl-3-methyl-23-dihydroimidazo [2,1-b] thiazol, dessen Herstellung und dieses enthaltende pharmazeutische Zusammensetzungen | |
| DE60004165T2 (de) | Fungizide azol derivate mit einer fluorinierten vinyl gruppe und ein verfahren zu deren herstellung | |
| DE3629929A1 (de) | Neue sulfonamido-aethylverbindungen, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung | |
| DE2926771A1 (de) | Thiazolidinderivate und verfahren zu ihrer herstellung | |
| CH645368A5 (de) | 2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)benzoesaeure-derivate sowie verfahren zu deren herstellung. | |
| DE1917432C2 (de) | 4-Hydroxythiazoline, deren Herstellung und Verwendung | |
| DE69107874T2 (de) | Imidazolderivate und diese Imidazolderivate als Wirkstoffe enthaltende Antiepileptika. | |
| DE69320420T2 (de) | Benzyl- und Benzhydryl Alkohole | |
| DE68911944T2 (de) | Cardiotonische Alkanoyl- und Aroyloxazole. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |