SK97095A3 - Derivatives of 3-hydroxyanthranilic acid, method and intermediate products for their manufacture, pharmaceutical compositions and their use - Google Patents
Derivatives of 3-hydroxyanthranilic acid, method and intermediate products for their manufacture, pharmaceutical compositions and their use Download PDFInfo
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- SK97095A3 SK97095A3 SK970-95A SK97095A SK97095A3 SK 97095 A3 SK97095 A3 SK 97095A3 SK 97095 A SK97095 A SK 97095A SK 97095 A3 SK97095 A3 SK 97095A3
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- Prior art keywords
- alkyl
- oso
- formula
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- same
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- 238000000034 method Methods 0.000 title claims abstract description 100
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 26
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
- WJXSWCUQABXPFS-UHFFFAOYSA-N 3-hydroxyanthranilic acid Chemical class NC1=C(O)C=CC=C1C(O)=O WJXSWCUQABXPFS-UHFFFAOYSA-N 0.000 title abstract description 11
- 239000013067 intermediate product Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 136
- 150000001875 compounds Chemical class 0.000 claims abstract description 130
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 62
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 58
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 53
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 52
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 51
- 150000002367 halogens Chemical class 0.000 claims abstract description 51
- -1 OSO2CH3 Chemical group 0.000 claims abstract description 50
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 49
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 41
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- 238000002360 preparation method Methods 0.000 claims abstract description 22
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 36
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 claims description 33
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 abstract description 4
- 108010072768 3-hydroxyanthranilate 3,4-dioxygenase Proteins 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 102100029016 3-hydroxyanthranilate 3,4-dioxygenase Human genes 0.000 abstract description 2
- 229910052727 yttrium Inorganic materials 0.000 abstract description 2
- 101710138657 Neurotoxin Proteins 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000002581 neurotoxin Substances 0.000 abstract 1
- 231100000618 neurotoxin Toxicity 0.000 abstract 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 239000000741 silica gel Substances 0.000 description 25
- 229910002027 silica gel Inorganic materials 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000013058 crude material Substances 0.000 description 21
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 16
- 238000003818 flash chromatography Methods 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 108090000417 Oxygenases Proteins 0.000 description 11
- 102000004020 Oxygenases Human genes 0.000 description 11
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- JOKPITBUODAHEN-UHFFFAOYSA-N sulfanylideneplatinum Chemical compound [Pt]=S JOKPITBUODAHEN-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
- YBAJOTZISQLAPO-UHFFFAOYSA-N 2-fluoro-5-hydroxy-4-propylbenzoic acid Chemical compound CCCC1=CC(F)=C(C(O)=O)C=C1O YBAJOTZISQLAPO-UHFFFAOYSA-N 0.000 description 3
- PXJJOILEDFTPJY-UHFFFAOYSA-N 2-fluoro-5-methoxy-4-propylphenol Chemical compound CCCC1=CC(F)=C(O)C=C1OC PXJJOILEDFTPJY-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- WKTGFYBNDVOWML-UHFFFAOYSA-N 4,6-dichloro-3-hydroxy-2-nitrobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=C(Cl)C(O)=C1[N+]([O-])=O WKTGFYBNDVOWML-UHFFFAOYSA-N 0.000 description 3
- IIOUHVMPDSYMFI-UHFFFAOYSA-N 6-fluoro-3-hydroxy-2-nitro-4-propylbenzoic acid Chemical compound CCCC1=CC(F)=C(C(O)=O)C([N+]([O-])=O)=C1O IIOUHVMPDSYMFI-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- 206010012289 Dementia Diseases 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- CYWJACBFQMOKOQ-UHFFFAOYSA-N methyl 2-fluoro-5-methoxy-4-propylbenzoate Chemical compound CCCC1=CC(F)=C(C(=O)OC)C=C1OC CYWJACBFQMOKOQ-UHFFFAOYSA-N 0.000 description 3
- 208000015122 neurodegenerative disease Diseases 0.000 description 3
- 238000010979 pH adjustment Methods 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- GJAWHXHKYYXBSV-RHRFEJLCSA-N (214C)pyridine-2,3-dicarboxylic acid Chemical compound N1=[14C](C(=O)O)C(C(=O)O)=CC=C1 GJAWHXHKYYXBSV-RHRFEJLCSA-N 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
- FWUNKBZDWIVAFY-UHFFFAOYSA-N 1-(4-bromobutyl)-2,4-dimethoxybenzene Chemical compound COC1=CC=C(CCCCBr)C(OC)=C1 FWUNKBZDWIVAFY-UHFFFAOYSA-N 0.000 description 2
- GNSANRGYWYXBGO-UHFFFAOYSA-N 1-chloro-2-methoxy-3-nitro-5-(trifluoromethyl)benzene Chemical compound COC1=C(Cl)C=C(C(F)(F)F)C=C1[N+]([O-])=O GNSANRGYWYXBGO-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- CIQNFXICVCINRP-UHFFFAOYSA-N 2-amino-4-chloro-3-hydroxy-6-(trifluoromethyl)benzoic acid Chemical compound NC1=C(O)C(Cl)=CC(C(F)(F)F)=C1C(O)=O CIQNFXICVCINRP-UHFFFAOYSA-N 0.000 description 2
- NNCCSUBPKRUEEA-UHFFFAOYSA-N 2-amino-4-chloro-3-methoxy-6-(trifluoromethyl)benzoic acid Chemical compound COC1=C(N)C(C(O)=O)=C(C(F)(F)F)C=C1Cl NNCCSUBPKRUEEA-UHFFFAOYSA-N 0.000 description 2
- CZNFABVUVHWEJF-UHFFFAOYSA-N 2-fluoro-5-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1F CZNFABVUVHWEJF-UHFFFAOYSA-N 0.000 description 2
- REDSLTKMNCCQBC-UHFFFAOYSA-N 2-fluoro-5-methoxybenzoic acid Chemical compound COC1=CC=C(F)C(C(O)=O)=C1 REDSLTKMNCCQBC-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- JPFWZXJGJCOUOQ-UHFFFAOYSA-N 3-chloro-2-methoxy-5-(trifluoromethyl)aniline Chemical compound COC1=C(N)C=C(C(F)(F)F)C=C1Cl JPFWZXJGJCOUOQ-UHFFFAOYSA-N 0.000 description 2
- GVPABBXTZOHVHB-UHFFFAOYSA-N 4,6-dibromo-3-hydroxy-2-nitrobenzoic acid Chemical compound OC(=O)C1=C(Br)C=C(Br)C(O)=C1[N+]([O-])=O GVPABBXTZOHVHB-UHFFFAOYSA-N 0.000 description 2
- WBJOIJXNUXOSLB-UHFFFAOYSA-N 4-(2,4-dimethoxyphenyl)butanal Chemical compound COC1=CC=C(CCCC=O)C(OC)=C1 WBJOIJXNUXOSLB-UHFFFAOYSA-N 0.000 description 2
- HRDBLCOYHJLCTE-UHFFFAOYSA-N 4-bromo-3-hydroxy-6-methoxy-2-nitrobenzoic acid Chemical compound COC1=CC(Br)=C(O)C([N+]([O-])=O)=C1C(O)=O HRDBLCOYHJLCTE-UHFFFAOYSA-N 0.000 description 2
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- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 210000003568 synaptosome Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C205/60—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms in ortho-position to the carboxyl group, e.g. nitro-salicylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/64—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Use Of Switch Circuits For Exchanges And Methods Of Control Of Multiplex Exchanges (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9300658A SE9300658D0 (sv) | 1993-02-26 | 1993-02-26 | New compounds |
PCT/SE1994/000153 WO1994019316A1 (en) | 1993-02-26 | 1994-02-24 | New compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
SK97095A3 true SK97095A3 (en) | 1996-10-02 |
Family
ID=20389054
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK970-95A SK97095A3 (en) | 1993-02-26 | 1994-02-24 | Derivatives of 3-hydroxyanthranilic acid, method and intermediate products for their manufacture, pharmaceutical compositions and their use |
Country Status (22)
Country | Link |
---|---|
US (2) | US5523475A (ja) |
EP (1) | EP0686145B1 (ja) |
JP (1) | JPH08509468A (ja) |
CN (1) | CN1121345A (ja) |
AT (1) | ATE189206T1 (ja) |
AU (1) | AU6160094A (ja) |
BR (1) | BR9406091A (ja) |
CZ (1) | CZ216895A3 (ja) |
DE (1) | DE69422800D1 (ja) |
EE (1) | EE9400386A (ja) |
FI (1) | FI954017A (ja) |
HU (1) | HUT72744A (ja) |
IL (1) | IL108753A0 (ja) |
IS (1) | IS4134A (ja) |
LT (1) | LT3211B (ja) |
MX (1) | MX9401456A (ja) |
NO (1) | NO953333L (ja) |
NZ (1) | NZ262219A (ja) |
PL (1) | PL310399A1 (ja) |
SE (1) | SE9300658D0 (ja) |
SK (1) | SK97095A3 (ja) |
WO (1) | WO1994019316A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2788691B1 (fr) | 1999-01-21 | 2002-06-14 | Oreal | Compositions pour la teinture d'oxydation des fibres keratiniques comprenant un coupleur cationique, nouveaux coupleurs cationiques, leur utilisation pour la teinture d'oxydation, et procedes de teinture |
FR2788768B1 (fr) | 1999-01-21 | 2001-02-16 | Oreal | Nouveaux 2-acylaminophenols cationiques, leur utilisation a titre de coupleur pour la teinture d'oxydation, compositions les comprenant, et procedes de teinture |
JP5641582B2 (ja) * | 2009-05-21 | 2014-12-17 | 静岡県公立大学法人 | 芳香族フッ素化合物の製造方法および新規化合物 |
US11867487B1 (en) | 2021-03-03 | 2024-01-09 | Wach Llc | System and method for aeronautical stabilization |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1847518A (en) * | 1930-01-23 | 1932-03-01 | Gen Aniline Works Inc | Omicron-amino-p-cresol-carboxylic-acid and process of making same |
US2652332A (en) * | 1951-07-19 | 1953-09-15 | Harold S Olcott | Stabilization of lipoidal substances |
US2843599A (en) * | 1954-09-28 | 1958-07-15 | Bayer Ag | Process for the production of phthalocyanine dyestuffs |
US2894984A (en) * | 1958-05-15 | 1959-07-14 | Pennsalt Chemicals Corp | 4-trifluoromethyl salicylic acids and their preparation |
US3211610A (en) * | 1961-09-29 | 1965-10-12 | Merck & Co Inc | Benzoic acid ester derivatives for treating coccidiosis and method of using same |
US3657436A (en) * | 1970-02-09 | 1972-04-18 | Hoffmann La Roche | Method of treating col-sk virus infections |
US4119609A (en) * | 1977-03-28 | 1978-10-10 | Shell Oil Company | Curable epoxy-carboxylic acid adducts |
DE2751136A1 (de) * | 1977-11-16 | 1979-05-23 | Bayer Ag | Verfahren zur herstellung aromatischer aminohydroxyverbindungen |
US5514676A (en) * | 1984-03-19 | 1996-05-07 | The Rockefeller University | Amino-benzoic acids and derivatives, and methods of use |
DE3608726A1 (de) * | 1986-03-15 | 1987-09-17 | Hoechst Ag | Verwendung aminosubstituierter benzoesaeuren als heilmittel gegen diarrhoe und arzneimittel auf basis dieser verbindungen |
US5025036A (en) * | 1987-10-01 | 1991-06-18 | Hoffmann-La Roche Inc. | Catechol carboxylic acids |
JP2684276B2 (ja) * | 1991-11-27 | 1997-12-03 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
US5512596A (en) * | 1994-09-02 | 1996-04-30 | Gilead Sciences, Inc. | Aromatic compounds |
-
1993
- 1993-02-26 SE SE9300658A patent/SE9300658D0/xx unknown
-
1994
- 1994-02-21 IS IS4134A patent/IS4134A/is unknown
- 1994-02-23 LT LTIP1882A patent/LT3211B/lt not_active IP Right Cessation
- 1994-02-24 IL IL10875394A patent/IL108753A0/xx unknown
- 1994-02-24 NZ NZ262219A patent/NZ262219A/en unknown
- 1994-02-24 WO PCT/SE1994/000153 patent/WO1994019316A1/en not_active Application Discontinuation
- 1994-02-24 US US08/201,213 patent/US5523475A/en not_active Expired - Lifetime
- 1994-02-24 DE DE69422800T patent/DE69422800D1/de not_active Expired - Lifetime
- 1994-02-24 AU AU61600/94A patent/AU6160094A/en not_active Abandoned
- 1994-02-24 BR BR9406091A patent/BR9406091A/pt not_active Application Discontinuation
- 1994-02-24 CZ CZ952168A patent/CZ216895A3/cs unknown
- 1994-02-24 PL PL94310399A patent/PL310399A1/xx unknown
- 1994-02-24 HU HU9502490A patent/HUT72744A/hu unknown
- 1994-02-24 CN CN94191798A patent/CN1121345A/zh active Pending
- 1994-02-24 SK SK970-95A patent/SK97095A3/sk unknown
- 1994-02-24 JP JP6518901A patent/JPH08509468A/ja active Pending
- 1994-02-24 AT AT94908557T patent/ATE189206T1/de not_active IP Right Cessation
- 1994-02-24 EP EP94908557A patent/EP0686145B1/en not_active Expired - Lifetime
- 1994-02-25 MX MX9401456A patent/MX9401456A/es unknown
- 1994-11-23 EE EE9400386A patent/EE9400386A/xx unknown
-
1995
- 1995-02-24 US US08/433,337 patent/US5883129A/en not_active Expired - Lifetime
- 1995-08-24 NO NO953333A patent/NO953333L/no unknown
- 1995-08-25 FI FI954017A patent/FI954017A/fi unknown
Also Published As
Publication number | Publication date |
---|---|
PL310399A1 (en) | 1995-12-11 |
NO953333D0 (no) | 1995-08-24 |
US5523475A (en) | 1996-06-04 |
AU6160094A (en) | 1994-09-14 |
IL108753A0 (en) | 1994-06-24 |
CZ216895A3 (en) | 1996-04-17 |
LT3211B (en) | 1995-04-25 |
JPH08509468A (ja) | 1996-10-08 |
FI954017A0 (fi) | 1995-08-25 |
HUT72744A (en) | 1996-05-28 |
ATE189206T1 (de) | 2000-02-15 |
DE69422800D1 (de) | 2000-03-02 |
HU9502490D0 (en) | 1995-10-30 |
EP0686145A1 (en) | 1995-12-13 |
FI954017A (fi) | 1995-08-25 |
IS4134A (is) | 1994-08-27 |
MX9401456A (es) | 1994-08-31 |
LTIP1882A (en) | 1994-09-25 |
NZ262219A (en) | 1997-04-24 |
CN1121345A (zh) | 1996-04-24 |
WO1994019316A1 (en) | 1994-09-01 |
BR9406091A (pt) | 1995-12-12 |
EP0686145B1 (en) | 2000-01-26 |
SE9300658D0 (sv) | 1993-02-26 |
NO953333L (no) | 1995-08-24 |
EE9400386A (et) | 1996-06-17 |
US5883129A (en) | 1999-03-16 |
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