DE2704329A1 - Therapeutisches mittel - Google Patents
Therapeutisches mittelInfo
- Publication number
- DE2704329A1 DE2704329A1 DE19772704329 DE2704329A DE2704329A1 DE 2704329 A1 DE2704329 A1 DE 2704329A1 DE 19772704329 DE19772704329 DE 19772704329 DE 2704329 A DE2704329 A DE 2704329A DE 2704329 A1 DE2704329 A1 DE 2704329A1
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- molecular weight
- units
- product according
- solution
- 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.)
- Ceased
Links
- 239000003814 drug Substances 0.000 title claims description 5
- 229940124597 therapeutic agent Drugs 0.000 title claims 2
- 229920000642 polymer Polymers 0.000 claims description 92
- -1 carboxy, carbamoyl Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- 239000000178 monomer Substances 0.000 claims description 24
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 23
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 21
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 16
- 238000009826 distribution Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- 230000001225 therapeutic effect Effects 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 13
- ZFRKEVMBGBIBGT-UHFFFAOYSA-N ethenyl benzenesulfonate Chemical group C=COS(=O)(=O)C1=CC=CC=C1 ZFRKEVMBGBIBGT-UHFFFAOYSA-N 0.000 claims description 10
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000002552 dosage form Substances 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 230000037396 body weight Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 229920001567 vinyl ester resin Polymers 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
- 125000005333 aroyloxy group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims 1
- NMDGERMUFYUHJG-UHFFFAOYSA-N ethenyl benzenesulfonate;sodium Chemical group [Na].C=COS(=O)(=O)C1=CC=CC=C1 NMDGERMUFYUHJG-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 103
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- XESUCHPMWXMNRV-UHFFFAOYSA-M sodium;2-ethenylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1C=C XESUCHPMWXMNRV-UHFFFAOYSA-M 0.000 description 47
- 208000025865 Ulcer Diseases 0.000 description 44
- 229920001577 copolymer Polymers 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 32
- 241000700159 Rattus Species 0.000 description 31
- 231100000397 ulcer Toxicity 0.000 description 31
- 239000000047 product Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 241001465754 Metazoa Species 0.000 description 24
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 21
- 241000700198 Cavia Species 0.000 description 19
- 229960001340 histamine Drugs 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000003999 initiator Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 229920001447 polyvinyl benzene Polymers 0.000 description 13
- 210000002784 stomach Anatomy 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 230000036269 ulceration Effects 0.000 description 13
- VMSBGXAJJLPWKV-UHFFFAOYSA-N 2-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=C VMSBGXAJJLPWKV-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 11
- 229910021641 deionized water Inorganic materials 0.000 description 11
- 208000000718 duodenal ulcer Diseases 0.000 description 11
- 238000006277 sulfonation reaction Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 10
- 241000282472 Canis lupus familiaris Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 231100000419 toxicity Toxicity 0.000 description 9
- 230000001988 toxicity Effects 0.000 description 9
- 208000007107 Stomach Ulcer Diseases 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 8
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 8
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000007170 pathology Effects 0.000 description 8
- 150000003431 steroids Chemical class 0.000 description 8
- 241000700199 Cavia porcellus Species 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 210000004379 membrane Anatomy 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 238000000108 ultra-filtration Methods 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- 230000000740 bleeding effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 6
- 102000057297 Pepsin A Human genes 0.000 description 5
- 108090000284 Pepsin A Proteins 0.000 description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 210000001198 duodenum Anatomy 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 229940111202 pepsin Drugs 0.000 description 5
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
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- 229920002223 polystyrene Polymers 0.000 description 4
- 239000012465 retentate Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 4
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 3
- 235000019743 Choline chloride Nutrition 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
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- 229910052786 argon Inorganic materials 0.000 description 3
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- 150000001768 cations Chemical class 0.000 description 3
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- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 3
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- 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
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- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 2
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- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 2
- 231100000956 nontoxicity Toxicity 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
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- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 2
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
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Classifications
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- 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
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- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
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- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- 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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
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-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65520076A | 1976-02-04 | 1976-02-04 | |
| US75269376A | 1976-12-20 | 1976-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2704329A1 true DE2704329A1 (de) | 1977-08-18 |
Family
ID=27096927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772704329 Ceased DE2704329A1 (de) | 1976-02-04 | 1977-02-02 | Therapeutisches mittel |
Country Status (10)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4395392A (en) * | 1980-06-24 | 1983-07-26 | Adria Laboratories Inc. | Method for treating kidney stones |
| US4375461A (en) * | 1980-07-25 | 1983-03-01 | Johnson & Johnson Products, Inc. | Sulfonated vinyl aromatic homopolymers and copolymers as dental plaque barriers |
| US4432967A (en) * | 1982-06-25 | 1984-02-21 | National Starch And Chemical Corp. | Contraceptive composition |
| EP0579153B1 (en) * | 1992-07-13 | 1998-04-08 | Tosoh Corporation | Process for producing tertiary alcohols |
| US6290946B1 (en) | 1999-05-13 | 2001-09-18 | Geltex Pharmaceuticals, Inc. | Anionic polymers as toxin binders and antibacterial agents |
| EP1800686A3 (en) * | 1999-05-13 | 2009-12-30 | Genzyme Corporation | Anionic polymers as toxin binders and antibacterial agents |
| US6270755B1 (en) | 1999-05-13 | 2001-08-07 | Geltex Pharmaceuticals, Inc. | Anionic polymers as toxin binders |
| CA2314494A1 (en) | 2000-05-02 | 2001-11-02 | Geltex Pharmaceuticals, Inc. | Anionic polymers as species specific antibacterial agents |
| EP1508578A4 (en) * | 2002-05-24 | 2006-01-04 | Sony Corp | ION-CONDUCTIVE POLYMER, SOLID POLYELECTROLYT AND CELL THEREOF TO WHICH IT APPLIES |
| CN101319023A (zh) * | 2002-07-22 | 2008-12-10 | 基酶有限公司 | 聚(钾和钠的苯乙烯苯磺酸盐),其制备及其用途 |
| AU2003903547A0 (en) * | 2003-07-10 | 2003-07-24 | Neoferma Australia Pty Ltd | Structures and methods of waterproofing same |
| JP6271378B2 (ja) * | 2014-09-05 | 2018-01-31 | 信越化学工業株式会社 | 導電性ポリマー用高分子化合物及びその製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3310481A (en) * | 1962-09-10 | 1967-03-21 | Dow Chemical Co | Removal of residual monomeric sulfonates from polymerizates thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4936644A (enrdf_load_stackoverflow) * | 1972-08-15 | 1974-04-05 |
-
1977
- 1977-01-20 IE IE111/77A patent/IE44690B1/en unknown
- 1977-01-21 SE SE7700670A patent/SE430070B/xx unknown
- 1977-01-27 GB GB3419/77A patent/GB1576016A/en not_active Expired
- 1977-01-31 JP JP961277A patent/JPS5296748A/ja active Pending
- 1977-02-02 DE DE19772704329 patent/DE2704329A1/de not_active Ceased
- 1977-02-02 DK DK44777A patent/DK44777A/da not_active Application Discontinuation
- 1977-02-03 FR FR7703021A patent/FR2340330A1/fr active Granted
- 1977-02-03 NL NL7701168A patent/NL7701168A/xx not_active Application Discontinuation
- 1977-02-03 CA CA271,038A patent/CA1114997A/en not_active Expired
- 1977-02-03 AU AU21934/77A patent/AU514389B2/en not_active Expired
-
1981
- 1981-10-16 SE SE8106138A patent/SE8106138L/sv not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3310481A (en) * | 1962-09-10 | 1967-03-21 | Dow Chemical Co | Removal of residual monomeric sulfonates from polymerizates thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5296748A (en) | 1977-08-13 |
| AU514389B2 (en) | 1981-02-05 |
| IE44690B1 (en) | 1982-02-24 |
| SE426835B (sv) | 1983-02-14 |
| FR2340330A1 (fr) | 1977-09-02 |
| SE430070B (sv) | 1983-10-17 |
| NL7701168A (nl) | 1977-08-08 |
| IE44690L (en) | 1977-08-04 |
| AU2193477A (en) | 1978-08-10 |
| CA1114997A (en) | 1981-12-22 |
| SE7700670L (sv) | 1977-08-05 |
| SE8106138L (sv) | 1981-10-16 |
| FR2340330B1 (enrdf_load_stackoverflow) | 1981-05-29 |
| DK44777A (da) | 1977-08-05 |
| GB1576016A (en) | 1980-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: MUELLER-BOERNER, R., DIPL.-ING., 1000 BERLIN WEY, |
|
| 8131 | Rejection |