MX2014013759A - (r) -nifuratel, su uso para el tratamiento de infecciones y sintesis de (r) y (s) -nifuratel. - Google Patents
(r) -nifuratel, su uso para el tratamiento de infecciones y sintesis de (r) y (s) -nifuratel.Info
- Publication number
- MX2014013759A MX2014013759A MX2014013759A MX2014013759A MX2014013759A MX 2014013759 A MX2014013759 A MX 2014013759A MX 2014013759 A MX2014013759 A MX 2014013759A MX 2014013759 A MX2014013759 A MX 2014013759A MX 2014013759 A MX2014013759 A MX 2014013759A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- nifuratel
- process according
- organic solvent
- appropriate
- Prior art date
Links
- 229960002136 nifuratel Drugs 0.000 title claims abstract description 60
- 238000011282 treatment Methods 0.000 title claims description 12
- 208000015181 infectious disease Diseases 0.000 title claims description 5
- 238000003786 synthesis reaction Methods 0.000 title abstract description 11
- 230000015572 biosynthetic process Effects 0.000 title abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 55
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 36
- -1 alkaline earth metal thiomethoxide Chemical class 0.000 claims description 18
- 229910001868 water Inorganic materials 0.000 claims description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 229940126214 compound 3 Drugs 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 229940125904 compound 1 Drugs 0.000 claims description 9
- 229940125782 compound 2 Drugs 0.000 claims description 9
- 239000003495 polar organic solvent Substances 0.000 claims description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 4
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QNYBOILAKBSWFG-JTQLQIEISA-N (2r)-2-(phenylmethoxymethyl)oxirane Chemical compound C([C@@H]1OC1)OCC1=CC=CC=C1 QNYBOILAKBSWFG-JTQLQIEISA-N 0.000 claims description 2
- QNYBOILAKBSWFG-SNVBAGLBSA-N (2s)-2-(phenylmethoxymethyl)oxirane Chemical compound C([C@H]1OC1)OCC1=CC=CC=C1 QNYBOILAKBSWFG-SNVBAGLBSA-N 0.000 claims description 2
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 claims description 2
- 241000894006 Bacteria Species 0.000 claims description 2
- 206010048461 Genital infection Diseases 0.000 claims description 2
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 2
- 206010046914 Vaginal infection Diseases 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 2
- 238000007306 functionalization reaction Methods 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 claims description 2
- 208000019206 urinary tract infection Diseases 0.000 claims description 2
- 206010017964 Gastrointestinal infection Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 claims 1
- SRQKTCXJCCHINN-NYYWCZLTSA-N nifuratel Chemical class O=C1OC(CSC)CN1\N=C\C1=CC=C([N+]([O-])=O)O1 SRQKTCXJCCHINN-NYYWCZLTSA-N 0.000 abstract description 15
- 230000000845 anti-microbial effect Effects 0.000 abstract description 4
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 3
- 239000003899 bactericide agent Substances 0.000 abstract description 2
- 239000000022 bacteriostatic agent Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 26
- 235000019441 ethanol Nutrition 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 239000012071 phase Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000003883 ointment base Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- 239000004264 Petrolatum Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 229940066842 petrolatum Drugs 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- RPHQZVFEMORVPW-CYBMUJFWSA-N tert-butyl n-[(5r)-2-oxo-5-(phenylmethoxymethyl)-1,3-oxazolidin-3-yl]carbamate Chemical compound O1C(=O)N(NC(=O)OC(C)(C)C)C[C@@H]1COCC1=CC=CC=C1 RPHQZVFEMORVPW-CYBMUJFWSA-N 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- CHWPAEUIAMQIJF-PGMHMLKASA-N (5r)-3-amino-5-(methylsulfanylmethyl)-1,3-oxazolidin-2-one;hydrochloride Chemical compound Cl.CSC[C@H]1CN(N)C(=O)O1 CHWPAEUIAMQIJF-PGMHMLKASA-N 0.000 description 2
- CHWPAEUIAMQIJF-WCCKRBBISA-N (5s)-3-amino-5-(methylsulfanylmethyl)-1,3-oxazolidin-2-one;hydrochloride Chemical compound Cl.CSC[C@@H]1CN(N)C(=O)O1 CHWPAEUIAMQIJF-WCCKRBBISA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 241000590002 Helicobacter pylori Species 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 229940014259 gelatin Drugs 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229940037467 helicobacter pylori Drugs 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- SGWOOZAJNFMPAB-LURJTMIESA-N tert-butyl n-[(5s)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NN1C[C@@H](CO)OC1=O SGWOOZAJNFMPAB-LURJTMIESA-N 0.000 description 2
- BCPPCLZVDUBWIH-ZETCQYMHSA-N tert-butyl n-[(5s)-5-(methylsulfanylmethyl)-2-oxo-1,3-oxazolidin-3-yl]carbamate Chemical compound CSC[C@@H]1CN(NC(=O)OC(C)(C)C)C(=O)O1 BCPPCLZVDUBWIH-ZETCQYMHSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- OFZXTEHOBJWCAU-OAHLLOKOSA-N (5S)-4,4-ditert-butyl-5-(phenylmethoxymethyl)-1,3-oxazolidin-2-one Chemical compound C(C)(C)(C)C1(NC(O[C@@H]1COCC1=CC=CC=C1)=O)C(C)(C)C OFZXTEHOBJWCAU-OAHLLOKOSA-N 0.000 description 1
- OYDDKCWJEMUOHF-SNVBAGLBSA-N (5r)-3-amino-5-(phenylmethoxymethyl)-1,3-oxazolidin-2-one Chemical compound O1C(=O)N(N)C[C@@H]1COCC1=CC=CC=C1 OYDDKCWJEMUOHF-SNVBAGLBSA-N 0.000 description 1
- OYDDKCWJEMUOHF-JTQLQIEISA-N (5s)-3-amino-5-(phenylmethoxymethyl)-1,3-oxazolidin-2-one Chemical compound O1C(=O)N(N)C[C@H]1COCC1=CC=CC=C1 OYDDKCWJEMUOHF-JTQLQIEISA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241001633064 Atopobium vaginae Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- YASHLWVLAWUAFS-FTYBWHBYSA-N C(C1=CC=CC=C1)OC[C@@H]1OC1.NN1C(O[C@H](C1)COCC1=CC=CC=C1)=O Chemical compound C(C1=CC=CC=C1)OC[C@@H]1OC1.NN1C(O[C@H](C1)COCC1=CC=CC=C1)=O YASHLWVLAWUAFS-FTYBWHBYSA-N 0.000 description 1
- YASHLWVLAWUAFS-QTFBQHTASA-N C(C1=CC=CC=C1)OC[C@H]1OC1.NN1C(O[C@@H](C1)COCC1=CC=CC=C1)=O Chemical compound C(C1=CC=CC=C1)OC[C@H]1OC1.NN1C(O[C@@H](C1)COCC1=CC=CC=C1)=O YASHLWVLAWUAFS-QTFBQHTASA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000606153 Chlamydia trachomatis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 241000207201 Gardnerella vaginalis Species 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
- 241001324870 Lactobacillus iners Species 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
- 239000004166 Lanolin Substances 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000577483 Salmonella enterica subsp. enterica serovar Paratyphi B Species 0.000 description 1
- 241000607760 Shigella sonnei Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 208000027709 Vulvovaginal disease Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 229940031955 anhydrous lanolin Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000305 astragalus gummifer gum Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 229940038705 chlamydia trachomatis Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000005429 filling process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- SGWOOZAJNFMPAB-ZCFIWIBFSA-N tert-butyl n-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NN1C[C@H](CO)OC1=O SGWOOZAJNFMPAB-ZCFIWIBFSA-N 0.000 description 1
- RPHQZVFEMORVPW-ZDUSSCGKSA-N tert-butyl n-[(5s)-2-oxo-5-(phenylmethoxymethyl)-1,3-oxazolidin-3-yl]carbamate Chemical compound O1C(=O)N(NC(=O)OC(C)(C)C)C[C@H]1COCC1=CC=CC=C1 RPHQZVFEMORVPW-ZDUSSCGKSA-N 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000583 toxicological profile Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
-
- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/02—Preparation of hydrazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
-
- 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
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20120167640 EP2662371A1 (en) | 2012-05-11 | 2012-05-11 | (R)-Nifuratel and synthesis of (R) and (S)-Nifuratel |
| PCT/EP2013/055078 WO2013167295A1 (en) | 2012-05-11 | 2013-03-13 | (r) -nifuratel, its use for the treatment of infections and synthesis of (r) and (s) -nifuratel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2014013759A true MX2014013759A (es) | 2015-08-07 |
Family
ID=47846051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2014013759A MX2014013759A (es) | 2012-05-11 | 2013-03-13 | (r) -nifuratel, su uso para el tratamiento de infecciones y sintesis de (r) y (s) -nifuratel. |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US9284306B2 (en:Method) |
| EP (2) | EP2662371A1 (en:Method) |
| JP (1) | JP2015515998A (en:Method) |
| KR (1) | KR20150008871A (en:Method) |
| CN (1) | CN104379580A (en:Method) |
| AU (1) | AU2013258385A1 (en:Method) |
| BR (1) | BR112014027953A2 (en:Method) |
| CA (1) | CA2869827A1 (en:Method) |
| CL (1) | CL2014002951A1 (en:Method) |
| CO (1) | CO7131368A2 (en:Method) |
| CR (1) | CR20140505A (en:Method) |
| DO (1) | DOP2014000252A (en:Method) |
| EA (1) | EA201492081A1 (en:Method) |
| EC (1) | ECSP14026432A (en:Method) |
| GE (2) | GEP201606595B (en:Method) |
| HK (1) | HK1202539A1 (en:Method) |
| IL (1) | IL235429A0 (en:Method) |
| IN (1) | IN2014DN09256A (en:Method) |
| MA (1) | MA20150279A1 (en:Method) |
| MX (1) | MX2014013759A (en:Method) |
| NZ (1) | NZ700752A (en:Method) |
| PE (1) | PE20150167A1 (en:Method) |
| PH (2) | PH12014502500B1 (en:Method) |
| SG (2) | SG10201608485XA (en:Method) |
| TN (1) | TN2014000430A1 (en:Method) |
| WO (1) | WO2013167295A1 (en:Method) |
| ZA (1) | ZA201407596B (en:Method) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108254453A (zh) * | 2016-12-28 | 2018-07-06 | 苏州电器科学研究院股份有限公司 | 一种有效测定塑料制品中邻苯二甲酸酯含量的检测方法 |
| KR20200055065A (ko) | 2017-09-20 | 2020-05-20 | 주식회사 피에이치파마 | 타일란스타틴 유사체 |
| CN108760950B (zh) * | 2018-04-25 | 2022-07-15 | 国检测试控股集团京诚检测有限公司 | 一种测定硝基呋喃代谢物的方法 |
| CN111892557B (zh) * | 2019-05-05 | 2022-11-08 | 河北圣泰材料股份有限公司 | 哌嗪类成膜离子液体的合成方法 |
| CN110672765B (zh) * | 2019-10-11 | 2022-03-18 | 温州海鹤药业有限公司 | 一种定量检测硝呋太尔中顺式异构体杂质的方法 |
| CN112457304B (zh) * | 2020-12-07 | 2022-03-11 | 中国药科大学 | 一种硝呋太尔的制备方法 |
| CN113828243B (zh) * | 2021-09-14 | 2022-06-28 | 南京南大药业有限责任公司 | 一种硝呋太尔制霉菌素栓制造方法及设备 |
| AU2024257248A1 (en) | 2023-04-17 | 2025-11-06 | Peak Bio, Inc. | Antibodies and antibody-drug conjugates and methods of use and synthetic processes and intermediates |
| CN116947838B (zh) * | 2023-07-25 | 2025-08-19 | 北京金城泰尔制药有限公司沧州分公司 | 高纯度硝呋太尔的生产方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL120945C (en:Method) | 1962-08-01 | |||
| CN100516063C (zh) * | 2006-03-16 | 2009-07-22 | 韩志强 | 硝呋太尔的生产方法 |
| CN100506820C (zh) | 2006-03-16 | 2009-07-01 | 韩志强 | (s)-硝呋太尔,其制备方法和应用 |
| CN101434584A (zh) * | 2007-11-15 | 2009-05-20 | 中山大学 | 具有抗菌活性的手性噁唑烷酮类化合物 |
| EP2243482A1 (en) * | 2009-04-20 | 2010-10-27 | Polichem SA | Use of nifuratel to treat infections caused by atopobium species |
-
2012
- 2012-05-11 EP EP20120167640 patent/EP2662371A1/en not_active Withdrawn
-
2013
- 2013-03-13 HK HK15103057.7A patent/HK1202539A1/xx unknown
- 2013-03-13 JP JP2015510685A patent/JP2015515998A/ja active Pending
- 2013-03-13 GE GEAP201313660A patent/GEP201606595B/en unknown
- 2013-03-13 GE GEAP201313967A patent/GEP201706626B/en unknown
- 2013-03-13 CN CN201380022803.0A patent/CN104379580A/zh active Pending
- 2013-03-13 IN IN9256DEN2014 patent/IN2014DN09256A/en unknown
- 2013-03-13 EP EP13708840.7A patent/EP2847189A1/en not_active Withdrawn
- 2013-03-13 KR KR20147031517A patent/KR20150008871A/ko not_active Withdrawn
- 2013-03-13 MA MA37496A patent/MA20150279A1/fr unknown
- 2013-03-13 NZ NZ700752A patent/NZ700752A/en not_active IP Right Cessation
- 2013-03-13 AU AU2013258385A patent/AU2013258385A1/en not_active Abandoned
- 2013-03-13 SG SG10201608485XA patent/SG10201608485XA/en unknown
- 2013-03-13 EA EA201492081A patent/EA201492081A1/ru unknown
- 2013-03-13 US US14/400,071 patent/US9284306B2/en not_active Expired - Fee Related
- 2013-03-13 MX MX2014013759A patent/MX2014013759A/es unknown
- 2013-03-13 BR BR112014027953A patent/BR112014027953A2/pt not_active IP Right Cessation
- 2013-03-13 CA CA 2869827 patent/CA2869827A1/en not_active Abandoned
- 2013-03-13 PE PE2014001944A patent/PE20150167A1/es not_active Application Discontinuation
- 2013-03-13 SG SG11201406447SA patent/SG11201406447SA/en unknown
- 2013-03-13 WO PCT/EP2013/055078 patent/WO2013167295A1/en not_active Ceased
-
2014
- 2014-10-16 TN TN2014000430A patent/TN2014000430A1/fr unknown
- 2014-10-20 ZA ZA2014/07596A patent/ZA201407596B/en unknown
- 2014-10-30 IL IL235429A patent/IL235429A0/en unknown
- 2014-10-30 CL CL2014002951A patent/CL2014002951A1/es unknown
- 2014-11-03 CR CR20140505A patent/CR20140505A/es unknown
- 2014-11-07 DO DO2014000252A patent/DOP2014000252A/es unknown
- 2014-11-10 PH PH12014502500A patent/PH12014502500B1/en unknown
- 2014-11-11 CO CO14248543A patent/CO7131368A2/es unknown
- 2014-11-11 EC ECIEPI201426432A patent/ECSP14026432A/es unknown
-
2015
- 2015-01-28 US US14/607,464 patent/US9067927B2/en not_active Expired - Fee Related
- 2015-09-24 PH PH12015502241A patent/PH12015502241A1/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| MX2014013759A (es) | (r) -nifuratel, su uso para el tratamiento de infecciones y sintesis de (r) y (s) -nifuratel. | |
| ES2609803T3 (es) | Nuevos derivados de triazol antifúngicos | |
| EP0868424B1 (en) | 4-pyrimidinyl- or 4-pyrazinyl-piperazinyl-phenyl-oxazolidinone derivatives, their preparation and their use as anti-bacterial agents | |
| RU2215740C2 (ru) | Оксазолидиноновые производные и фармацевтические композиции на их основе | |
| CN108727406B (zh) | 含氮杂环取代的苯并噁嗪噁唑烷酮类化合物及其制备方法和用途 | |
| EA023350B1 (ru) | Противомикробные соединения, способы их получения и применение | |
| JP2000500489A (ja) | 三環置換基を有するオキサゾリジノン抗菌剤 | |
| JP2016536338A (ja) | 抗微生物化合物ならびにそれの製造方法および使用方法 | |
| EP3164393A1 (fr) | Dérivés de flavaglines | |
| CN105189513A (zh) | 葡萄糖醇，1-脱氧-1-(甲胺基)-,1-(6-氨基-3,5-二氟吡啶-2-基)-8-氯-6-氟-1,4-二氢-7-(3-羟基氮杂环丁烷-l-基)-4-氧-3-喹啉羧酸盐的结晶形态 | |
| CN104364240B (zh) | 一种用于预防或治疗分支杆菌疾病的药物 | |
| CN107205989A (zh) | 治疗、预防或降低皮肤感染风险的方法 | |
| JP2023529011A (ja) | インデン化合物、その医薬組成物、及びそれらの治療応用 | |
| CN116970028A (zh) | 大环拟肽类蛋白酶抑制剂及其用途 | |
| TWI840723B (zh) | 吡咯衍生物及製備方法和用途 | |
| US20170087163A1 (en) | Solid forms of an alpha, omega di-substituted dihydroxy cyclopentyl compound and methods for the preparation and use thereof | |
| CA2772907C (en) | Selective antibacterials for clostridium difficile infections | |
| LU84144A1 (fr) | Analogues de la mitomycine | |
| CN107033095B (zh) | 含哌嗪腙结构的噁唑烷酮类化合物 | |
| US20090062361A1 (en) | Therapeutic hydantoins | |
| WO2024081885A1 (en) | Method for inhibiting clostridioides difficile spore germination | |
| CN119306668A (zh) | 苯并咪唑类化合物及其制备方法和用途 |