DE3613061A1 - 1-hydroxy-2-pyridone, verfahren zu ihrer herstellung und arzneimittel, die sie enthalten - Google Patents
1-hydroxy-2-pyridone, verfahren zu ihrer herstellung und arzneimittel, die sie enthaltenInfo
- Publication number
- DE3613061A1 DE3613061A1 DE19863613061 DE3613061A DE3613061A1 DE 3613061 A1 DE3613061 A1 DE 3613061A1 DE 19863613061 DE19863613061 DE 19863613061 DE 3613061 A DE3613061 A DE 3613061A DE 3613061 A1 DE3613061 A1 DE 3613061A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- methyl
- formula
- pyridone
- compound
- 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.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- SNUSZUYTMHKCPM-UHFFFAOYSA-N 1-hydroxypyridin-2-one Chemical class ON1C=CC=CC1=O SNUSZUYTMHKCPM-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims abstract description 7
- 239000003814 drug Substances 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 7
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical class OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000000843 anti-fungal effect Effects 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- CMJRXUFGEJJSCZ-UHFFFAOYSA-N 1-hydroxy-4-methyl-6-[[4-[4-(trifluoromethyl)phenoxy]phenoxy]methyl]pyridin-2-one Chemical compound ON1C(=O)C=C(C)C=C1COC(C=C1)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 CMJRXUFGEJJSCZ-UHFFFAOYSA-N 0.000 claims description 2
- UDYUIWXQUBNDHC-UHFFFAOYSA-N 6-[[4-(4-chlorophenoxy)phenoxy]methyl]-1-hydroxy-4-methylpyridin-2-one Chemical compound ON1C(=O)C=C(C)C=C1COC(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 UDYUIWXQUBNDHC-UHFFFAOYSA-N 0.000 claims description 2
- 229940121375 antifungal agent Drugs 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 210000004400 mucous membrane Anatomy 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000001717 pathogenic effect Effects 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- -1 phenyloxymethyl Chemical group 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241000233866 Fungi Species 0.000 description 5
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XQMRZWSYBUCVAX-UHFFFAOYSA-N 4-(4-chlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C=C1 XQMRZWSYBUCVAX-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 4
- 229960004022 clotrimazole Drugs 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- LUIDLGSVCGOJGK-UHFFFAOYSA-N 6-(chloromethyl)-4-methylpyran-2-one Chemical compound CC=1C=C(CCl)OC(=O)C=1 LUIDLGSVCGOJGK-UHFFFAOYSA-N 0.000 description 3
- MJQVWFQOPJBTIP-UHFFFAOYSA-N 6-[[4-[(2,4-dichlorophenyl)methyl]phenoxy]methyl]-1-hydroxy-3,4-dimethylpyridin-2-one Chemical compound ON1C(=O)C(C)=C(C)C=C1COC(C=C1)=CC=C1CC1=CC=C(Cl)C=C1Cl MJQVWFQOPJBTIP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XMWGTKZEDLCVIG-UHFFFAOYSA-N 1-(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1 XMWGTKZEDLCVIG-UHFFFAOYSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- QCOBRTWWFHKJFN-UHFFFAOYSA-N 1-hydroxy-4-methyl-6-[[3-(naphthalen-1-ylmethoxy)phenyl]sulfanylmethyl]pyridin-2-one Chemical compound ON1C(=O)C=C(C)C=C1CSC1=CC=CC(OCC=2C3=CC=CC=C3C=CC=2)=C1 QCOBRTWWFHKJFN-UHFFFAOYSA-N 0.000 description 2
- QOIROKIBJHTPPE-UHFFFAOYSA-N 1-hydroxy-4-methyl-6-[[4-(naphthalen-1-ylmethoxy)phenoxy]methyl]pyridin-2-one Chemical compound ON1C(=O)C=C(C)C=C1COC(C=C1)=CC=C1OCC1=CC=CC2=CC=CC=C12 QOIROKIBJHTPPE-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- LIYGCLJYTHRBQV-UHFFFAOYSA-N 3,5-dichloro-4-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(C=O)C=C1Cl LIYGCLJYTHRBQV-UHFFFAOYSA-N 0.000 description 2
- QXRPZAARCBAZKD-UHFFFAOYSA-N 3-(naphthalen-1-ylmethylsulfanyl)phenol Chemical compound OC1=CC=CC(SCC=2C3=CC=CC=C3C=CC=2)=C1 QXRPZAARCBAZKD-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- MCHNMSOCAOCXLL-UHFFFAOYSA-N 6-[[2,6-dichloro-4-(chloromethyl)phenoxy]methyl]-4-methylpyran-2-one Chemical compound O1C(=O)C=C(C)C=C1COC1=C(Cl)C=C(CCl)C=C1Cl MCHNMSOCAOCXLL-UHFFFAOYSA-N 0.000 description 2
- HUXNFDXZBIBKQD-UHFFFAOYSA-N 6-[[2,6-dichloro-4-(naphthalen-2-ylsulfanylmethyl)phenoxy]methyl]-1-hydroxy-4-methylpyridin-2-one Chemical compound ON1C(=O)C=C(C)C=C1COC(C(=C1)Cl)=C(Cl)C=C1CSC1=CC=C(C=CC=C2)C2=C1 HUXNFDXZBIBKQD-UHFFFAOYSA-N 0.000 description 2
- XBVBQNAVZFUVNY-UHFFFAOYSA-N 6-[[4-(4-chlorophenoxy)phenoxy]methyl]-1-hydroxypyridin-2-one Chemical compound C1=CC(=O)N(O)C(COC=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)=C1 XBVBQNAVZFUVNY-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- MXZNUGFCDVAXLG-CHWSQXEVSA-N [(2S)-1-[(2R)-3-methyl-2-(pyridine-4-carbonylamino)butanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@@H](NC(=O)c1ccncc1)C(=O)N1CCC[C@@H]1B(O)O MXZNUGFCDVAXLG-CHWSQXEVSA-N 0.000 description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229940126208 compound 22 Drugs 0.000 description 2
- 125000004970 halomethyl group Chemical group 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000003491 skin Anatomy 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
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- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- 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
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863613061 DE3613061A1 (de) | 1986-04-18 | 1986-04-18 | 1-hydroxy-2-pyridone, verfahren zu ihrer herstellung und arzneimittel, die sie enthalten |
| EP87105537A EP0241918B1 (de) | 1986-04-18 | 1987-04-14 | 1-Hydroxy-2-pyridone, Verfahren zu ihrer Herstellung und Arzneimittel, die sie enthalten, sowie bei der Herstellung der 1-Hydroxy-2-pyridone gebildete Zwischenprodukte |
| AT87105537T ATE76638T1 (de) | 1986-04-18 | 1987-04-14 | 1-hydroxy-2-pyridone, verfahren zu ihrer herstellung und arzneimittel, die sie enthalten, sowie bei der herstellung der 1-hydroxy-2- pyridone gebildete zwischenprodukte. |
| ES198787105537T ES2041656T3 (es) | 1986-04-18 | 1987-04-14 | Procedimiento para preparar 1-hidroxi-2-piridonas. |
| DE8787105537T DE3779352D1 (de) | 1986-04-18 | 1987-04-14 | 1-hydroxy-2-pyridone, verfahren zu ihrer herstellung und arzneimittel, die sie enthalten, sowie bei der herstellung der 1-hydroxy-2-pyridone gebildete zwischenprodukte. |
| AR87307291A AR242187A1 (es) | 1986-04-18 | 1987-04-14 | Procedimiento para la preparacion de 1-hidroxi-2-piridonas, obtencion de medicamentos que las contienen, e intermediarios utiles en dicho procedimiento. |
| MX609387A MX6093A (es) | 1986-04-18 | 1987-04-15 | Procedimiento para preparar 1-hydroxi-2-piridonas. |
| DK198387A DK167494B1 (da) | 1986-04-18 | 1987-04-15 | 1-hydroxy-2-pyridoner eller fysiologisk acceptable salte deraf med baser, deres fremstilling samt laegemiddel indeholdende dem |
| NO871602A NO170540C (no) | 1986-04-18 | 1987-04-15 | En analogifremgangsmaate for fremstilling av 1-hydroksy-2-pyridoner |
| IE100987A IE59965B1 (en) | 1986-04-18 | 1987-04-16 | 1-hydroxy-2-pyridones, a process for their preparation, an medicaments which contain them, and intermediates formed I the preparation of the 1-hydroxy-2-pyridones |
| ZA872745A ZA872745B (en) | 1986-04-18 | 1987-04-16 | 1-hydroxy-2-pyridones,a process for their preparation,and medicaments which contain them,and intermediates formed in the preparation of the 1-hydroxy-2-pyridones |
| HU871683A HU198020B (en) | 1986-04-18 | 1987-04-16 | Process for producing 1-hydroxy-2-pyridon derivatives and pharmaceutical compositions containing them |
| CA000535001A CA1302415C (en) | 1986-04-18 | 1987-04-16 | 1-hydroxy-2-pyridones, a process for their preparation, and medicaments which contain them, and intermediates formed in the preparation of the 1-hydroxy-2-pyridones |
| PT84702A PT84702B (pt) | 1986-04-18 | 1987-04-16 | Processo para a preparacao de 1-hidroxi-2-piridonas, de composicoes farmaceuticas que as contem e dos produtos intermediarios para a sua preparacao |
| IL82231A IL82231A (en) | 1986-04-18 | 1987-04-16 | 1-hydroxy-2-pyridones,process for their preparation and pharmaceutical compositions which contain them |
| US07/038,903 US4797409A (en) | 1986-04-18 | 1987-04-16 | 1-hydroxy-2-pyridones, a process for their preparation, and medicaments which contain them, and intermediates formed in the preparation of the 1-hydroxy-2-pyridones |
| FI871699A FI86635C (fi) | 1986-04-18 | 1987-04-16 | Foerfarande foer framstaellning av terapeutiskt aktiva 1-hydroxi-2-pyridonderivat och vid framstaellning av 1-hydroxi-2-pyridoner bildade mellanprodukter. |
| NZ220020A NZ220020A (en) | 1986-04-18 | 1987-04-16 | 1-hydroxy-2-pyridones and pharmaceutical composition |
| AU71717/87A AU602684B2 (en) | 1986-04-18 | 1987-04-16 | 1-hydroxy-2-pyridones, a process for their preparation, and medicaments which contain them, and intermediates formed in the preparation of the 1-hydroxy-2-pyridones |
| KR1019870003684A KR950007754B1 (ko) | 1986-04-18 | 1987-04-17 | 1-하이드록시-2-피리돈의 제조방법 |
| JP62093445A JPS62249974A (ja) | 1986-04-18 | 1987-04-17 | １−ヒドロキシ−２−ピリドン類 |
| PH35156A PH24106A (en) | 1986-04-18 | 1987-04-20 | 1-hydroxy-2-pyridones,medicaments which contain them and method of use thereof |
| AT0258387A AT388551B (de) | 1986-04-18 | 1987-10-08 | 1-hydroxy-2-pyridone, verfahren zu ihrer herstellung und arzneimittel, die sie enthalten, sowie bei der herstellung der 1-hydroxy-2-pyridone gebildete zwischenprodukte |
| GR920401787T GR3005465T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-04-18 | 1992-08-20 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863613061 DE3613061A1 (de) | 1986-04-18 | 1986-04-18 | 1-hydroxy-2-pyridone, verfahren zu ihrer herstellung und arzneimittel, die sie enthalten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3613061A1 true DE3613061A1 (de) | 1987-10-22 |
Family
ID=6298947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863613061 Withdrawn DE3613061A1 (de) | 1986-04-18 | 1986-04-18 | 1-hydroxy-2-pyridone, verfahren zu ihrer herstellung und arzneimittel, die sie enthalten |
Country Status (4)
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2540218A (en) * | 1947-08-25 | 1951-02-06 | Squibb & Sons Inc | 2-hydroxy-pyridine-n-oxide and process for preparing same |
| US3269904A (en) * | 1963-05-06 | 1966-08-30 | Squibb & Sons Inc | Hydroxy-pyridine oxides in an antifungal method |
| BE738288A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-08-31 | 1970-03-02 | ||
| DE2214608B2 (de) * | 1972-03-25 | 1977-03-31 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von 1- hydroxy-2-pyridonen |
-
1986
- 1986-04-18 DE DE19863613061 patent/DE3613061A1/de not_active Withdrawn
-
1987
- 1987-04-15 MX MX609387A patent/MX6093A/es unknown
- 1987-04-16 ZA ZA872745A patent/ZA872745B/xx unknown
- 1987-04-17 JP JP62093445A patent/JPS62249974A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2540218A (en) * | 1947-08-25 | 1951-02-06 | Squibb & Sons Inc | 2-hydroxy-pyridine-n-oxide and process for preparing same |
| US3269904A (en) * | 1963-05-06 | 1966-08-30 | Squibb & Sons Inc | Hydroxy-pyridine oxides in an antifungal method |
| BE738288A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-08-31 | 1970-03-02 | ||
| DE2214608B2 (de) * | 1972-03-25 | 1977-03-31 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von 1- hydroxy-2-pyridonen |
Non-Patent Citations (1)
| Title |
|---|
| DE-Z: Arzneim.-Forsch.31,(II), 8a, S.1311-16 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA872745B (en) | 1987-12-30 |
| JPH03864B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-01-09 |
| JPS62249974A (ja) | 1987-10-30 |
| MX6093A (es) | 1994-02-28 |
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