NO301889B1 - Polymerer og oligomerer av gallesyrederivater, fremgangsmåte for fremstilling derav, deres anvendelse og preparater som inneholder slike - Google Patents
Polymerer og oligomerer av gallesyrederivater, fremgangsmåte for fremstilling derav, deres anvendelse og preparater som inneholder slike Download PDFInfo
- Publication number
- NO301889B1 NO301889B1 NO924922A NO924922A NO301889B1 NO 301889 B1 NO301889 B1 NO 301889B1 NO 924922 A NO924922 A NO 924922A NO 924922 A NO924922 A NO 924922A NO 301889 B1 NO301889 B1 NO 301889B1
- Authority
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- Norway
- Prior art keywords
- alkyl
- group
- bile acids
- polymers
- formula
- Prior art date
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- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical class C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 17
- 229920000642 polymer Polymers 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000003613 bile acid Substances 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 15
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 13
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 12
- 238000007334 copolymerization reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical class C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims description 2
- 235000013373 food additive Nutrition 0.000 claims description 2
- 239000002778 food additive Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 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
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 229920001567 vinyl ester resin Polymers 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- -1 aryl mercaptans Chemical class 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 13
- 235000019400 benzoyl peroxide Nutrition 0.000 description 13
- 238000003756 stirring Methods 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 210000000941 bile Anatomy 0.000 description 8
- 239000000047 product Substances 0.000 description 8
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- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
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- 239000000700 radioactive tracer Substances 0.000 description 6
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- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 230000000968 intestinal effect Effects 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- WBWWGRHZICKQGZ-HZAMXZRMSA-N taurocholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 WBWWGRHZICKQGZ-HZAMXZRMSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 230000009103 reabsorption Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920001268 Cholestyramine Polymers 0.000 description 3
- 229920002911 Colestipol Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
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- GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 description 3
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 208000037887 cell injury Diseases 0.000 description 1
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- 239000007795 chemical reaction product Substances 0.000 description 1
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 1
- 229960001091 chenodeoxycholic acid Drugs 0.000 description 1
- 229940099352 cholate Drugs 0.000 description 1
- 201000001883 cholelithiasis Diseases 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
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- 230000008602 contraction Effects 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 230000001278 effect on cholesterol Effects 0.000 description 1
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- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
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- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 210000001758 mesenteric vein Anatomy 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
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- 230000009057 passive transport Effects 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
- 229960003912 probucol Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000002271 resection Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical class CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical class CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
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- 239000003643 water by type Substances 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
-
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
- C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/26—Nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Polymers & Plastics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Gastroenterology & Hepatology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicinal Preparation (AREA)
- Detergent Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Lubricants (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4142379 | 1991-12-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO924922D0 NO924922D0 (no) | 1992-12-18 |
| NO924922L NO924922L (no) | 1993-06-21 |
| NO301889B1 true NO301889B1 (no) | 1997-12-22 |
Family
ID=6447759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO924922A NO301889B1 (no) | 1991-12-20 | 1992-12-18 | Polymerer og oligomerer av gallesyrederivater, fremgangsmåte for fremstilling derav, deres anvendelse og preparater som inneholder slike |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5430116A (hu) |
| EP (1) | EP0549967B1 (hu) |
| JP (1) | JP3292318B2 (hu) |
| AT (1) | ATE135380T1 (hu) |
| AU (1) | AU653658B2 (hu) |
| CA (1) | CA2085831C (hu) |
| DE (1) | DE59205695D1 (hu) |
| DK (1) | DK0549967T3 (hu) |
| ES (1) | ES2087422T3 (hu) |
| FI (1) | FI108451B (hu) |
| GR (1) | GR3019564T3 (hu) |
| HU (1) | HUT63434A (hu) |
| IL (1) | IL104166A (hu) |
| NO (1) | NO301889B1 (hu) |
| NZ (1) | NZ245503A (hu) |
| TW (1) | TW255898B (hu) |
| ZA (1) | ZA929827B (hu) |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ245504A (en) * | 1991-12-20 | 1995-08-28 | Hoechst Ag | Bile acid derivatives containing an ethylenically unsaturated grouping |
| ATE156911T1 (de) * | 1994-03-04 | 1997-08-15 | Waters Investments Ltd | Verfahren zum nachweis von polymeren in einer lösung, detektorsystem und eine ein solches detektorsystem beinhaltende chromatographievorrichtung |
| US5994391A (en) * | 1994-09-13 | 1999-11-30 | G.D. Searle And Company | Benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
| US6262277B1 (en) | 1994-09-13 | 2001-07-17 | G.D. Searle And Company | Intermediates and processes for the preparation of benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
| US6642268B2 (en) | 1994-09-13 | 2003-11-04 | G.D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothipines and HMG Co-A reductase inhibitors |
| US6268392B1 (en) | 1994-09-13 | 2001-07-31 | G. D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors |
| US6107494A (en) * | 1994-09-13 | 2000-08-22 | G.D. Searle And Company | Substituted 5-aryl-benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake |
| DE19633268A1 (de) * | 1996-08-19 | 1998-02-26 | Hoechst Ag | Polymere Gallensäure-Resorptionsinhibitoren mit gleichzeitiger Gallensäure-Adsorberwirkung |
| KR100313150B1 (ko) * | 1997-12-31 | 2001-12-28 | 박종섭 | 리소콜릴에시딜(메타)아크릴레이트 단량체와 그를 도입한 공중합체 수지 및 이 수지를 이용한 포토레지스트 |
| US6221897B1 (en) * | 1998-06-10 | 2001-04-24 | Aventis Pharma Deutschland Gmbh | Benzothiepine 1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use |
| IL143944A0 (en) * | 1998-12-23 | 2002-04-21 | Searle Llc | Combinations for cardiovascular indications |
| AU2157400A (en) | 1998-12-23 | 2000-07-31 | G.D. Searle & Co. | Combinations of cholesteryl ester transfer protein inhibitors and hmg coa reductase inhibitors for cardiovascular indications |
| EP1342475A1 (en) | 1998-12-23 | 2003-09-10 | G.D. Searle LLC. | Combinations of ileal bile acid transport inhibitors and cholesteryl ester transfer protein inhibitors for cardiovascular indications |
| PL348580A1 (en) | 1998-12-23 | 2002-06-03 | Searle Llc | Combinations of ileal bile acid transport inhibitors and fibric acid derivatives for cardiovascular indications |
| CN1338944A (zh) * | 1998-12-23 | 2002-03-06 | G.D.瑟尔有限公司 | 用于心血管适应症的胆固醇酯转移蛋白抑制剂和苯氧异丁酸类衍生物的联合形式 |
| ES2189529T3 (es) | 1998-12-23 | 2003-07-01 | Searle Llc | Combinaciones de inhiidores para el transporte de acidos biliares en el ileon y agentes complejantes para indicaciones cardiovasculares. |
| PT1140184E (pt) * | 1998-12-23 | 2003-10-31 | Searle Llc | Combinacoes de inibidores de proteina de transferencia de ester de colesterilo com derivados de acido nicotinico para indicacoes cardiovasculares |
| WO2000038723A1 (en) | 1998-12-23 | 2000-07-06 | G.D. Searle Llc | Combinations of cholesteryl ester transfer protein inhibitors and bile acid sequestering agents for cardiovascular indications |
| US6794544B2 (en) | 2000-03-10 | 2004-09-21 | Pharmacia Corporation | Method for the preparation of tetrahydrobenzothiepines |
| US20020061888A1 (en) * | 2000-03-10 | 2002-05-23 | Keller Bradley T. | Combination therapy for the prophylaxis and treatment of hyperlipidemic conditions and disorders |
| SE0003766D0 (sv) * | 2000-10-18 | 2000-10-18 | Astrazeneca Ab | Novel formulation |
| US20040077625A1 (en) * | 2001-07-25 | 2004-04-22 | Tremont Samuel J. | Novel 1,4-benzothiazepine and 1,5-benzothiazepine compounds as inhibitors of apical sodium codependent bile acid transport abd taurocholate uptake |
| JP2005518347A (ja) | 2001-11-02 | 2005-06-23 | ジー．ディー． サール エルエルシー | 頂端ナトリウム共依存性胆汁酸輸送（ａｓｂｔ）およびタウロコール酸塩取り込みの阻害剤としての新規一および二フッ化ベンゾチエピン化合物 |
| MXPA04006255A (es) | 2002-01-17 | 2004-09-27 | Pharmacia Corp | Compuestos novedosos de alquil/aril hidroxi o ceto tiepina como inhibidores del transporte del acido biliar codependiente del sodio apical y la captacion de taurocolato. |
| GB0307918D0 (en) | 2003-04-05 | 2003-05-14 | Astrazeneca Ab | Therapeutic use |
| EP2575821B1 (en) | 2010-05-26 | 2015-08-12 | Satiogen Pharmaceuticals, Inc. | Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions |
| CA2815698C (en) | 2010-11-08 | 2019-04-30 | Albireo Ab | A pharmaceutical combination comprising an ibat inhibitor and a bile acid binder |
| RS57778B1 (sr) | 2010-11-08 | 2018-12-31 | Albireo Ab | Inhibitori crevnog transportera žučne kiseline (ibat) za lečenje bolesti jetre |
| KR20190135545A (ko) | 2011-10-28 | 2019-12-06 | 루메나 파마수티컬즈, 인코포레이티드 | 고담혈증 및 담즙 정체성 간 질환 치료용 담즙산 재순환 억제제 |
| MX369466B (es) | 2011-10-28 | 2019-11-08 | Lumena Pharmaceuticals Inc | Inhibidores de la recirculación de ácidos biliares para el tratamiento de enfermedades hepáticas colestásicas pediátricas. |
| MX2015013196A (es) | 2013-03-15 | 2016-04-15 | Lumena Pharmaceuticals Inc | Inhibidores de reciclaje de acidos biliares para el tratamiento de la enfermedad de reflujo gastroesofagico y esofago de barrett. |
| JP2016514684A (ja) | 2013-03-15 | 2016-05-23 | ルメナ ファーマシューティカルズ エルエルシー | 原発性硬化性胆管炎および炎症性腸疾患の処置のための胆汁酸再循環阻害剤 |
| JO3301B1 (ar) | 2013-04-26 | 2018-09-16 | Albireo Ab | تعديلات بلورية على إيلوبيكسيبات |
| KR102560954B1 (ko) | 2014-06-25 | 2023-07-31 | 이에이 파마 가부시키가이샤 | 고형 제제 및 그의 착색 방지 또는 착색 감소 방법 |
| WO2016045642A1 (en) * | 2014-09-28 | 2016-03-31 | National Institute Of Biological Sciences, Beijing | Polymeric bile acid derivatives inhibit hepatitis b and d virus and ntcp transport |
| EP3012252A1 (en) | 2014-10-24 | 2016-04-27 | Ferring BV | Crystal modifications of elobixibat |
| US10786529B2 (en) | 2016-02-09 | 2020-09-29 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US10441605B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US10441604B2 (en) | 2016-02-09 | 2019-10-15 | Albireo Ab | Cholestyramine pellets and methods for preparation thereof |
| ES2874669T3 (es) | 2016-02-09 | 2021-11-05 | Albireo Ab | Formulación oral de colestiramina y uso de la misma |
| CN108601745B (zh) | 2016-02-09 | 2021-12-07 | 阿尔比里奥公司 | 口服考来烯胺制剂及其用途 |
| EP3664782A1 (en) | 2017-08-09 | 2020-06-17 | Albireo AB | Cholestyramine pellets, oral cholestyramine formulations and use thereof |
| JP2020530448A (ja) | 2017-08-09 | 2020-10-22 | アルビレオ・アクチボラグ | コレスチラミン顆粒、経口コレスチラミン製剤、及びそれらの使用 |
| US10793534B2 (en) | 2018-06-05 | 2020-10-06 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| TW202015699A (zh) | 2018-06-05 | 2020-05-01 | 瑞典商艾爾比瑞歐公司 | 苯并噻(二)氮呯(benzothia(di)azepine)化合物及其作為膽汁酸調節劑之用途 |
| WO2019245449A1 (en) | 2018-06-20 | 2019-12-26 | Albireo Ab | Pharmaceutical formulation of odevixibat |
| US11801226B2 (en) | 2018-06-20 | 2023-10-31 | Albireo Ab | Pharmaceutical formulation of odevixibat |
| US10722457B2 (en) | 2018-08-09 | 2020-07-28 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US11007142B2 (en) | 2018-08-09 | 2021-05-18 | Albireo Ab | Oral cholestyramine formulation and use thereof |
| US11549878B2 (en) | 2018-08-09 | 2023-01-10 | Albireo Ab | In vitro method for determining the adsorbing capacity of an insoluble adsorbant |
| US10941127B2 (en) | 2019-02-06 | 2021-03-09 | Albireo Ab | Benzothiadiazepine compounds and their use as bile acid modulators |
| EP3921027B1 (en) | 2019-02-06 | 2023-07-19 | Albireo AB | Benzothiazepine compounds and their use as bile acid modulators |
| US10975045B2 (en) | 2019-02-06 | 2021-04-13 | Aibireo AB | Benzothiazepine compounds and their use as bile acid modulators |
| FI3921028T3 (fi) | 2019-02-06 | 2023-01-31 | Bentsotiadiatsepiinin yhdisteet ja niiden käyttö sappihapon modulaattoreina | |
| KR20210137046A (ko) | 2019-02-12 | 2021-11-17 | 미룸 파마슈티컬스, 인크. | 담즙정체의 치료 방법 |
| AR120682A1 (es) | 2019-12-04 | 2022-03-09 | Albireo Ab | Compuestos de benzotiadiazepina y su uso como moduladores del ácido biliar |
| TW202134220A (zh) | 2019-12-04 | 2021-09-16 | 瑞典商艾爾比瑞歐公司 | 苯并噻(二)氮呯(benzothia(di)azepine)化合物及其作為膽酸調節劑之用途 |
| TW202134223A (zh) | 2019-12-04 | 2021-09-16 | 瑞典商艾爾比瑞歐公司 | 苯并噻(二)氮呯(benzothia(di)azepine)化合物及其作為膽酸調節劑之用途 |
| EP4069247A1 (en) | 2019-12-04 | 2022-10-12 | Albireo AB | Benzothiadiazepine compounds and their use as bile acid modulators |
| AR120683A1 (es) | 2019-12-04 | 2022-03-09 | Albireo Ab | Compuestos de benzoti(di)azepina y su uso como ácido biliar |
| CR20220315A (es) | 2019-12-04 | 2022-10-26 | Albireo Ab | Compuestos de benzoti(di)azepina y su uso como moduladores del ácido biliar |
| EP4069359B1 (en) | 2019-12-04 | 2024-01-03 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| ES2973355T3 (es) | 2019-12-04 | 2024-06-19 | Albireo Ab | Compuestos de benzotia(di)azepina y su uso como moduladores del ácido biliar |
| WO2021110887A1 (en) | 2019-12-04 | 2021-06-10 | Albireo Ab | Benzothiazepine compounds and their use as bile acid modulators |
| US11014898B1 (en) | 2020-12-04 | 2021-05-25 | Albireo Ab | Benzothiazepine compounds and their use as bile acid modulators |
| WO2022029101A1 (en) | 2020-08-03 | 2022-02-10 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| EP4188541A1 (en) | 2020-08-03 | 2023-06-07 | Albireo AB | Benzothia(di)azepine compounds and their use as bile acid modulators |
| KR20230106651A (ko) | 2020-11-12 | 2023-07-13 | 알비레오 에이비 | 진행성 가족성 간내 담즙정체증(pfic)을 치료하기 위한 오데빅시바트 |
| AU2021390172A1 (en) | 2020-12-04 | 2023-06-22 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| TW202313579A (zh) | 2021-06-03 | 2023-04-01 | 瑞典商艾爾比瑞歐公司 | 苯并噻(二)氮呯(benzothia(di)azepine)化合物及其作為膽酸調節劑之用途 |
| US20230398125A1 (en) | 2022-06-09 | 2023-12-14 | Albireo Ab | Treating hepatitis |
| US20240067617A1 (en) | 2022-07-05 | 2024-02-29 | Albireo Ab | Benzothia(di)azepine compounds and their use as bile acid modulators |
| US20240207286A1 (en) | 2022-12-09 | 2024-06-27 | Albireo Ab | Asbt inhibitors in the treatment of renal diseases |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3383281A (en) * | 1961-09-22 | 1968-05-14 | Merck & Co Inc | Method for binding bile acids in vivo |
| US3709867A (en) * | 1971-11-22 | 1973-01-09 | Owens Illinois Inc | Process for lubricating vinyl polymers with sitosterol compounds and stabilized product thereof |
| SU525709A1 (ru) * | 1975-03-10 | 1976-08-25 | Московский Ордена Ленина И Ордена Трудового Красного Знамени Государственный Университет Имени М.В.Ломоносова | Способ получени полимеров |
| US4104285A (en) * | 1977-04-22 | 1978-08-01 | Hoffmann-La Roche Inc. | Taurine and glycine derivatives |
| DE3930696A1 (de) * | 1989-09-14 | 1991-03-28 | Hoechst Ag | Gallensaeurederivate, verfahren zu ihrer herstellung, verwendung als arzneimittel |
| US5250524A (en) * | 1990-12-06 | 1993-10-05 | Hoechst Aktiengesellschaft | Bile acid derivatives, process for their preparation and use of these compounds as pharmaceuticals |
-
1992
- 1992-12-17 DE DE59205695T patent/DE59205695D1/de not_active Expired - Lifetime
- 1992-12-17 AU AU30209/92A patent/AU653658B2/en not_active Ceased
- 1992-12-17 ES ES92121459T patent/ES2087422T3/es not_active Expired - Lifetime
- 1992-12-17 AT AT92121459T patent/ATE135380T1/de not_active IP Right Cessation
- 1992-12-17 NZ NZ245503A patent/NZ245503A/en unknown
- 1992-12-17 DK DK92121459.9T patent/DK0549967T3/da active
- 1992-12-17 US US07/992,411 patent/US5430116A/en not_active Expired - Lifetime
- 1992-12-17 FI FI925735A patent/FI108451B/fi active
- 1992-12-17 EP EP92121459A patent/EP0549967B1/de not_active Expired - Lifetime
- 1992-12-18 IL IL10416692A patent/IL104166A/en not_active IP Right Cessation
- 1992-12-18 NO NO924922A patent/NO301889B1/no not_active IP Right Cessation
- 1992-12-18 JP JP35485792A patent/JP3292318B2/ja not_active Expired - Lifetime
- 1992-12-18 CA CA002085831A patent/CA2085831C/en not_active Expired - Lifetime
- 1992-12-18 HU HU9204020A patent/HUT63434A/hu unknown
- 1992-12-18 ZA ZA929827A patent/ZA929827B/xx unknown
- 1992-12-29 TW TW081110422A patent/TW255898B/zh active
-
1996
- 1996-04-05 GR GR960400949T patent/GR3019564T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW255898B (hu) | 1995-09-01 |
| FI108451B (fi) | 2002-01-31 |
| AU3020992A (en) | 1993-06-24 |
| ZA929827B (en) | 1993-06-23 |
| FI925735A0 (fi) | 1992-12-17 |
| AU653658B2 (en) | 1994-10-06 |
| NZ245503A (en) | 1995-11-27 |
| DK0549967T3 (da) | 1996-07-22 |
| JPH0625354A (ja) | 1994-02-01 |
| NO924922D0 (no) | 1992-12-18 |
| NO924922L (no) | 1993-06-21 |
| EP0549967B1 (de) | 1996-03-13 |
| HUT63434A (en) | 1993-08-30 |
| GR3019564T3 (en) | 1996-07-31 |
| FI925735A (fi) | 1993-06-21 |
| DE59205695D1 (de) | 1996-04-18 |
| IL104166A (en) | 1999-04-11 |
| ATE135380T1 (de) | 1996-03-15 |
| IL104166A0 (en) | 1993-05-13 |
| CA2085831A1 (en) | 1993-06-21 |
| US5430116A (en) | 1995-07-04 |
| HU9204020D0 (en) | 1993-04-28 |
| CA2085831C (en) | 2006-05-30 |
| ES2087422T3 (es) | 1996-07-16 |
| JP3292318B2 (ja) | 2002-06-17 |
| EP0549967A1 (de) | 1993-07-07 |
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