ES2353685T3 - Derivados de tiazolidina y su uso como agente antifúngico. - Google Patents
Derivados de tiazolidina y su uso como agente antifúngico. Download PDFInfo
- Publication number
- ES2353685T3 ES2353685T3 ES01963155T ES01963155T ES2353685T3 ES 2353685 T3 ES2353685 T3 ES 2353685T3 ES 01963155 T ES01963155 T ES 01963155T ES 01963155 T ES01963155 T ES 01963155T ES 2353685 T3 ES2353685 T3 ES 2353685T3
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- methylene
- alkyl
- 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
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical class C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 238000000034 method Methods 0.000 claims abstract description 54
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 12
- 208000031888 Mycoses Diseases 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- 238000011321 prophylaxis Methods 0.000 claims abstract description 4
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims abstract description 3
- -1 morpholino, piperidinyl Chemical group 0.000 claims description 93
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 229940121375 antifungal agent Drugs 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 208000015181 infectious disease Diseases 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
- 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 8
- 239000003429 antifungal agent Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000005975 2-phenylethyloxy group Chemical group 0.000 claims description 7
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
- JGQGIKPAXRUGEO-UHFFFAOYSA-N 2-[5-[[3-[(dibenzylamino)methyl]-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=C1CN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC=C1OCC1=CC=CC=C1 JGQGIKPAXRUGEO-UHFFFAOYSA-N 0.000 claims description 3
- HAQCAFHUWZJBFB-UHFFFAOYSA-N 2-[5-[[3-[(dipentylamino)methyl]-4-phenylmethoxyphenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(CN(CCCCC)CCCCC)=CC=1C=C1SC(=S)N(CC(O)=O)C1=O HAQCAFHUWZJBFB-UHFFFAOYSA-N 0.000 claims description 3
- 241000228197 Aspergillus flavus Species 0.000 claims description 3
- 241000335423 Blastomyces Species 0.000 claims description 3
- 241000223203 Coccidioides Species 0.000 claims description 3
- 201000007336 Cryptococcosis Diseases 0.000 claims description 3
- 241000221204 Cryptococcus neoformans Species 0.000 claims description 3
- 241001480035 Epidermophyton Species 0.000 claims description 3
- 241000228402 Histoplasma Species 0.000 claims description 3
- 241001480037 Microsporum Species 0.000 claims description 3
- 241001537205 Paracoccidioides Species 0.000 claims description 3
- 241000223238 Trichophyton Species 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004360 trifluorophenyl group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 241001225321 Aspergillus fumigatus Species 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229940091771 aspergillus fumigatus Drugs 0.000 claims description 2
- 238000005815 base catalysis Methods 0.000 claims description 2
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 15
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 139
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 92
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 58
- 238000005160 1H NMR spectroscopy Methods 0.000 description 55
- 239000000243 solution Substances 0.000 description 53
- 239000000843 powder Substances 0.000 description 42
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 239000003208 petroleum Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000000047 product Substances 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 25
- 239000000203 mixture Substances 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
- 229910052938 sodium sulfate Inorganic materials 0.000 description 21
- 235000011152 sodium sulphate Nutrition 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000012267 brine Substances 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 11
- 230000008014 freezing Effects 0.000 description 10
- 238000007710 freezing Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 241000222122 Candida albicans Species 0.000 description 8
- 229940095731 candida albicans Drugs 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 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 8
- 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 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 210000002421 cell wall Anatomy 0.000 description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 230000002538 fungal effect Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 5
- FTTVXHXKTPOQDV-UHFFFAOYSA-N 5-formyl-2-phenylmethoxybenzoic acid Chemical compound OC(=O)C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 FTTVXHXKTPOQDV-UHFFFAOYSA-N 0.000 description 5
- UTCFOFWMEPQCSR-UHFFFAOYSA-N 5-formylsalicylic acid Chemical compound OC(=O)C1=CC(C=O)=CC=C1O UTCFOFWMEPQCSR-UHFFFAOYSA-N 0.000 description 5
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 5
- 230000000843 anti-fungal effect Effects 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XSOMVWJDTCGXDN-UHFFFAOYSA-N 5-formyl-2-methoxy-n,n-dipentylbenzamide Chemical compound CCCCCN(CCCCC)C(=O)C1=CC(C=O)=CC=C1OC XSOMVWJDTCGXDN-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 229920001503 Glucan Polymers 0.000 description 4
- 102100024023 Histone PARylation factor 1 Human genes 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 239000000284 extract 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 3
- BLLLLFAEDGYKLT-UHFFFAOYSA-N 2-(2-sulfanylidene-1,3-thiazolidin-3-yl)acetic acid Chemical compound OC(=O)CN1CCSC1=S BLLLLFAEDGYKLT-UHFFFAOYSA-N 0.000 description 3
- QNWCLECYLVYBEA-UHFFFAOYSA-N 2-[(2,4-difluorophenyl)methoxy]-5-formylbenzoic acid Chemical compound OC(=O)C1=CC(C=O)=CC=C1OCC1=CC=C(F)C=C1F QNWCLECYLVYBEA-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- DIRFWUKIGJBMOT-UHFFFAOYSA-N 3-[[benzyl(2-phenylethyl)amino]methyl]-4-phenylmethoxybenzaldehyde Chemical compound C=1C=CC=CC=1CCN(CC=1C=CC=CC=1)CC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 DIRFWUKIGJBMOT-UHFFFAOYSA-N 0.000 description 3
- DISMAEDMDMLJOE-UHFFFAOYSA-N 5-formyl-2-[[4-(trifluoromethyl)phenyl]methoxy]benzoic acid Chemical compound OC(=O)C1=CC(C=O)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 DISMAEDMDMLJOE-UHFFFAOYSA-N 0.000 description 3
- DKADRYUNTXYTHX-UHFFFAOYSA-N 5-formyl-2-hydroxy-n,n-dipentylbenzamide Chemical compound CCCCCN(CCCCC)C(=O)C1=CC(C=O)=CC=C1O DKADRYUNTXYTHX-UHFFFAOYSA-N 0.000 description 3
- NRYRFMSMFKLTRE-UHFFFAOYSA-N 5-formyl-n-methyl-n-phenyl-2-phenylmethoxybenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 NRYRFMSMFKLTRE-UHFFFAOYSA-N 0.000 description 3
- 229920002101 Chitin Polymers 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 102000006722 Mannosyltransferases Human genes 0.000 description 3
- 108010087568 Mannosyltransferases Proteins 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 101001123538 Nicotiana tabacum Putrescine N-methyltransferase 1 Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- OCJAGRYUKAWYQD-UHFFFAOYSA-N benzyl 5-formyl-2-phenylmethoxybenzoate Chemical compound C=1C=CC=CC=1COC(=O)C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 OCJAGRYUKAWYQD-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
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- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- IOKSKWANKJZYNW-UHFFFAOYSA-N n,n-dibenzyl-4-formyl-2-phenylmethoxybenzamide Chemical compound C=1C=CC=CC=1COC1=CC(C=O)=CC=C1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 IOKSKWANKJZYNW-UHFFFAOYSA-N 0.000 description 3
- LIKOXWIAUBMKIH-UHFFFAOYSA-N n,n-dibenzyl-5-formyl-2-phenylmethoxybenzamide Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)C(=O)C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 LIKOXWIAUBMKIH-UHFFFAOYSA-N 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000011200 topical administration Methods 0.000 description 3
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- GLBCCKHCYJSNGE-UHFFFAOYSA-N (2,4-difluorophenyl)methyl 2-[(2,4-difluorophenyl)methoxy]-5-formylbenzoate Chemical compound FC1=CC(F)=CC=C1COC(=O)C1=CC(C=O)=CC=C1OCC1=CC=C(F)C=C1F GLBCCKHCYJSNGE-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- YIXGWSOWVTWUDG-UHFFFAOYSA-N 2-[(2,4-difluorophenyl)methoxy]-5-formyl-n,n-dipentylbenzamide Chemical compound CCCCCN(CCCCC)C(=O)C1=CC(C=O)=CC=C1OCC1=CC=C(F)C=C1F YIXGWSOWVTWUDG-UHFFFAOYSA-N 0.000 description 2
- VOEYVGKGBOROGN-UHFFFAOYSA-N 2-phenylethyl 5-formyl-2-(2-phenylethoxy)benzoate Chemical compound C=1C=CC=CC=1CCOC(=O)C1=CC(C=O)=CC=C1OCCC1=CC=CC=C1 VOEYVGKGBOROGN-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
- HVISLGBCHHWICI-UHFFFAOYSA-N 3-[(4-benzylpiperidin-1-yl)methyl]-4-phenylmethoxybenzaldehyde Chemical compound C1CC(CC=2C=CC=CC=2)CCN1CC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 HVISLGBCHHWICI-UHFFFAOYSA-N 0.000 description 2
- UHLSHWZWBNYCGK-UHFFFAOYSA-N 3-[(dipentylamino)methyl]-4-phenylmethoxybenzaldehyde Chemical compound CCCCCN(CCCCC)CC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 UHLSHWZWBNYCGK-UHFFFAOYSA-N 0.000 description 2
- XANPKPXROBKQNH-UHFFFAOYSA-N 3-phenylmethoxy-4-(trifluoromethylsulfonyl)benzaldehyde Chemical compound FC(F)(F)S(=O)(=O)C1=CC=C(C=O)C=C1OCC1=CC=CC=C1 XANPKPXROBKQNH-UHFFFAOYSA-N 0.000 description 2
- NZHPWTXZGYNJBD-UHFFFAOYSA-N 4-formyl-2-phenylmethoxybenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1OCC1=CC=CC=C1 NZHPWTXZGYNJBD-UHFFFAOYSA-N 0.000 description 2
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 208000030159 metabolic disease Diseases 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
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000020166 milkshake Nutrition 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
- 239000002324 mouth wash Substances 0.000 description 1
- FEKRFYZGYUTGRY-UHFFFAOYSA-N n'-ethylmethanediimine Chemical compound CCN=C=N FEKRFYZGYUTGRY-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 230000037125 natural defense Effects 0.000 description 1
- 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
- 239000003883 ointment base Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 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
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000009467 reduction Effects 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
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 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
- 238000010998 test method Methods 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 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
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0021419.7A GB0021419D0 (en) | 2000-08-31 | 2000-08-31 | Compounds |
| GB0021419 | 2000-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2353685T3 true ES2353685T3 (es) | 2011-03-04 |
Family
ID=9898614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES01963155T Expired - Lifetime ES2353685T3 (es) | 2000-08-31 | 2001-08-30 | Derivados de tiazolidina y su uso como agente antifúngico. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6740670B2 (Direct) |
| EP (1) | EP1313731B1 (Direct) |
| JP (1) | JP2004509121A (Direct) |
| AT (1) | ATE482954T1 (Direct) |
| AU (1) | AU2001284188A1 (Direct) |
| DE (1) | DE60143165D1 (Direct) |
| ES (1) | ES2353685T3 (Direct) |
| GB (1) | GB0021419D0 (Direct) |
| WO (1) | WO2002022612A1 (Direct) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1656361T3 (da) * | 2003-08-11 | 2008-05-05 | Hoffmann La Roche | Piperazin med OR-substitueret phenylgruppe og anvendelse deraf som GLYT1-inhibitorer |
| CN1950342B (zh) | 2004-03-15 | 2012-09-26 | 詹森药业有限公司 | 作为阿片受体调节剂的新化合物 |
| DE602005014274D1 (de) | 2004-12-09 | 2009-06-10 | Hoffmann La Roche | Phenylpiperazin-methanon-derivate |
| MX2007006896A (es) | 2004-12-15 | 2007-06-26 | Hoffmann La Roche | Fenil-metanonas bi- y triciclicas sustituidas como inhibidores del transportador 1 de glicina (glyt-1) para el tratamiento de la enfermedad de alzheimer. |
| US7485637B2 (en) | 2005-01-04 | 2009-02-03 | Hoffmann-La Roche Inc. | Benzoyl-tetrahydropiperidine derivatives |
| WO2006072436A1 (en) | 2005-01-07 | 2006-07-13 | F. Hoffmann-La Roche Ag | [4-(heteroaryl) piperazin-1-yl]-(2,5-substituted -phenyl)methanone derivatives as glycine transporter 1 (glyt-1) inhibitors for the treatment of neurological and neuropsychiatric disorders |
| JP2008527016A (ja) | 2005-01-18 | 2008-07-24 | エフ．ホフマン−ラ ロシュ アーゲー | 神経及び神経精神病の疾患の治療のためのグリシントランスポーター１（ＧｌｙＴ−１）阻害剤としての２，５−二置換フェニルメタノン誘導体 |
| KR100915472B1 (ko) | 2005-01-26 | 2009-09-03 | 에프. 호프만-라 로슈 아게 | 페닐 메탄온 유도체 및 그의 글라이신 트랜스포터 1억제제로서의 용도 |
| ATE449761T1 (de) | 2005-02-07 | 2009-12-15 | Hoffmann La Roche | Heterocyclsche substituierte phenylmethanone als inhibitoren des glycintransporters 1 |
| CA2721459A1 (en) * | 2008-05-20 | 2009-11-26 | Merck Sharp & Dohme Corp. | Efficient production of heterologous proteins using mannosyl transferase inhibitors |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| RU2662153C1 (ru) * | 2017-04-20 | 2018-07-24 | Общество С Ограниченной Ответственностью "Дермавитал Групп" | Гибридные эфиры на основе производных тиазолидин-2,4-диона и азолов (1н-1,3-имидазола и 1н-1,3,4-триазола) и их применение |
| RU2690161C1 (ru) * | 2018-06-28 | 2019-05-31 | Общество С Ограниченной Ответственностью "Дермавитал Групп" | 3,5-Замещенные производные тиазолидин-2,4-диона, обладающие противомикробной активностью |
| RU2703997C1 (ru) * | 2018-12-13 | 2019-10-23 | Общество с ограниченной ответственностью "Л-Био" | Гибридные амиды на основе триазола и тиазолидина, обладающие антимикробной активностью |
| US11292776B2 (en) | 2019-12-12 | 2022-04-05 | University Of Sharjah | Small molecule inhibitors of fungal hyphae and biofilm formation |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US47109A (en) * | 1865-04-04 | Improvement in governors | ||
| FR1604530A (Direct) * | 1967-06-06 | 1971-11-29 | ||
| JPS5740478A (en) * | 1980-08-22 | 1982-03-06 | Ono Pharmaceut Co Ltd | Rhodanine derivative, its preparation and aldose reductase inhibitor containing rhodanine derivative |
| 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 |
| DE19835316A1 (de) * | 1998-08-05 | 2000-02-10 | Bosch Gmbh Robert | Gesteuerte Gleichrichterbrücke mit Überspannungsschutz |
| AU6330799A (en) * | 1998-09-30 | 2000-04-17 | Roche Diagnostics Gmbh | Rhodanine carboxylic acid derivatives for the treatment and prevention of metabolic bone disorders |
-
2000
- 2000-08-31 GB GBGB0021419.7A patent/GB0021419D0/en not_active Ceased
-
2001
- 2001-08-30 WO PCT/GB2001/003860 patent/WO2002022612A1/en not_active Ceased
- 2001-08-30 JP JP2002526865A patent/JP2004509121A/ja active Pending
- 2001-08-30 DE DE60143165T patent/DE60143165D1/de not_active Expired - Lifetime
- 2001-08-30 ES ES01963155T patent/ES2353685T3/es not_active Expired - Lifetime
- 2001-08-30 EP EP01963155A patent/EP1313731B1/en not_active Expired - Lifetime
- 2001-08-30 AU AU2001284188A patent/AU2001284188A1/en not_active Abandoned
- 2001-08-30 AT AT01963155T patent/ATE482954T1/de active
-
2003
- 2003-02-21 US US10/371,979 patent/US6740670B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6740670B2 (en) | 2004-05-25 |
| JP2004509121A (ja) | 2004-03-25 |
| WO2002022612A1 (en) | 2002-03-21 |
| ATE482954T1 (de) | 2010-10-15 |
| GB0021419D0 (en) | 2000-10-18 |
| WO2002022612A8 (en) | 2002-05-23 |
| EP1313731A1 (en) | 2003-05-28 |
| DE60143165D1 (de) | 2010-11-11 |
| AU2001284188A1 (en) | 2002-03-26 |
| US20030216453A1 (en) | 2003-11-20 |
| EP1313731B1 (en) | 2010-09-29 |
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