NO322789B1 - Farmasoytisk akseptabel smaksmaskerende flytende eksipientbase, farmasoytisk blanding inneholdende den, samt en fremgangsmate for smaksmaskering ved hjelp av eksipientbasen - Google Patents
Farmasoytisk akseptabel smaksmaskerende flytende eksipientbase, farmasoytisk blanding inneholdende den, samt en fremgangsmate for smaksmaskering ved hjelp av eksipientbasen Download PDFInfo
- Publication number
- NO322789B1 NO322789B1 NO19973480A NO973480A NO322789B1 NO 322789 B1 NO322789 B1 NO 322789B1 NO 19973480 A NO19973480 A NO 19973480A NO 973480 A NO973480 A NO 973480A NO 322789 B1 NO322789 B1 NO 322789B1
- Authority
- NO
- Norway
- Prior art keywords
- excipient base
- cellulose
- compound
- per
- polyethylene glycol
- Prior art date
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- 239000000546 pharmaceutical excipient Substances 0.000 title claims abstract description 60
- 239000007788 liquid Substances 0.000 title claims abstract description 32
- 230000000873 masking effect Effects 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 36
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 30
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 23
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 16
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical group CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 15
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 15
- 229920002678 cellulose Polymers 0.000 claims description 15
- 239000001913 cellulose Substances 0.000 claims description 15
- 229960002146 guaifenesin Drugs 0.000 claims description 14
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 12
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 11
- MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 claims description 7
- 229960001985 dextromethorphan Drugs 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 6
- 230000000954 anitussive effect Effects 0.000 claims description 6
- 229940124584 antitussives Drugs 0.000 claims description 6
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003172 expectorant agent Substances 0.000 claims description 6
- 230000003419 expectorant effect Effects 0.000 claims description 6
- 229960001680 ibuprofen Drugs 0.000 claims description 6
- 229960003908 pseudoephedrine Drugs 0.000 claims description 6
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 claims description 6
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 5
- 239000000739 antihistaminic agent Substances 0.000 claims description 5
- 239000000850 decongestant Substances 0.000 claims description 5
- 229960002009 naproxen Drugs 0.000 claims description 5
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 5
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 4
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 4
- 229940125715 antihistaminic agent Drugs 0.000 claims description 4
- 239000003434 antitussive agent Substances 0.000 claims description 4
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 4
- 229940124581 decongestants Drugs 0.000 claims description 4
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 claims description 4
- 229940066493 expectorants Drugs 0.000 claims description 4
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 claims description 4
- 229960000395 phenylpropanolamine Drugs 0.000 claims description 4
- 150000005599 propionic acid derivatives Chemical class 0.000 claims description 4
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 claims description 3
- 229960000725 brompheniramine Drugs 0.000 claims description 3
- ZDIGNSYAACHWNL-UHFFFAOYSA-N brompheniramine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Br)C=C1 ZDIGNSYAACHWNL-UHFFFAOYSA-N 0.000 claims description 3
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 claims description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- UFLGIAIHIAPJJC-UHFFFAOYSA-N Tripelennamine Chemical compound C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CC=C1 UFLGIAIHIAPJJC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229960000383 azatadine Drugs 0.000 claims description 2
- SEBMTIQKRHYNIT-UHFFFAOYSA-N azatadine Chemical compound C1CN(C)CCC1=C1C2=NC=CC=C2CCC2=CC=CC=C21 SEBMTIQKRHYNIT-UHFFFAOYSA-N 0.000 claims description 2
- 229960003166 bromazine Drugs 0.000 claims description 2
- NUNIWXHYABYXKF-UHFFFAOYSA-N bromazine Chemical compound C=1C=C(Br)C=CC=1C(OCCN(C)C)C1=CC=CC=C1 NUNIWXHYABYXKF-UHFFFAOYSA-N 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- -1 cyproheptatine Chemical compound 0.000 claims description 2
- 229960000520 diphenhydramine Drugs 0.000 claims description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 2
- 229960000991 ketoprofen Drugs 0.000 claims description 2
- 229960000582 mepyramine Drugs 0.000 claims description 2
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 235000010981 methylcellulose Nutrition 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 claims description 2
- 229960001802 phenylephrine Drugs 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 claims description 2
- 229960003223 tripelennamine Drugs 0.000 claims description 2
- 229960001128 triprolidine Drugs 0.000 claims description 2
- CBEQULMOCCWAQT-WOJGMQOQSA-N triprolidine Chemical compound C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C/CN1CCCC1 CBEQULMOCCWAQT-WOJGMQOQSA-N 0.000 claims description 2
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims 3
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 claims 1
- BCXHDORHMMZBBZ-DORFAMGDSA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC BCXHDORHMMZBBZ-DORFAMGDSA-N 0.000 claims 1
- ISFHAYSTHMVOJR-UHFFFAOYSA-N Phenindamine Chemical compound C1N(C)CCC(C2=CC=CC=C22)=C1C2C1=CC=CC=C1 ISFHAYSTHMVOJR-UHFFFAOYSA-N 0.000 claims 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims 1
- 230000001387 anti-histamine Effects 0.000 claims 1
- 229960003291 chlorphenamine Drugs 0.000 claims 1
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 claims 1
- 229960004415 codeine phosphate Drugs 0.000 claims 1
- 229960003871 codeine sulfate Drugs 0.000 claims 1
- 229960002691 dexbrompheniramine Drugs 0.000 claims 1
- ZDIGNSYAACHWNL-HNNXBMFYSA-N dexbrompheniramine Chemical compound C1([C@H](CCN(C)C)C=2N=CC=CC=2)=CC=C(Br)C=C1 ZDIGNSYAACHWNL-HNNXBMFYSA-N 0.000 claims 1
- 229960001882 dexchlorpheniramine Drugs 0.000 claims 1
- SOYKEARSMXGVTM-HNNXBMFYSA-N dexchlorpheniramine Chemical compound C1([C@H](CCN(C)C)C=2N=CC=CC=2)=CC=C(Cl)C=C1 SOYKEARSMXGVTM-HNNXBMFYSA-N 0.000 claims 1
- 229960005178 doxylamine Drugs 0.000 claims 1
- HCFDWZZGGLSKEP-UHFFFAOYSA-N doxylamine Chemical compound C=1C=CC=NC=1C(C)(OCCN(C)C)C1=CC=CC=C1 HCFDWZZGGLSKEP-UHFFFAOYSA-N 0.000 claims 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims 1
- 229940124641 pain reliever Drugs 0.000 claims 1
- 229960003534 phenindamine Drugs 0.000 claims 1
- 229960003975 potassium Drugs 0.000 claims 1
- 239000001508 potassium citrate Substances 0.000 claims 1
- 229960002635 potassium citrate Drugs 0.000 claims 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 claims 1
- 235000011082 potassium citrates Nutrition 0.000 claims 1
- 229960004839 potassium iodide Drugs 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 16
- 239000003814 drug Substances 0.000 abstract description 11
- 229940079593 drug Drugs 0.000 abstract description 10
- 238000009472 formulation Methods 0.000 description 33
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000003765 sweetening agent Substances 0.000 description 6
- 235000003599 food sweetener Nutrition 0.000 description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 229940041616 menthol Drugs 0.000 description 3
- 229960005489 paracetamol Drugs 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 3
- 239000004299 sodium benzoate Substances 0.000 description 3
- 235000010234 sodium benzoate Nutrition 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 229920002534 Polyethylene Glycol 1450 Polymers 0.000 description 2
- 229920002253 Tannate Polymers 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 229960003893 phenacetin Drugs 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 1
- MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 description 1
- WFXURHIXPXVPGM-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;2-methyl-9-phenyl-1,3,4,9-tetrahydroindeno[2,1-c]pyridine Chemical compound OC(=O)C(O)C(O)C(O)=O.C1N(C)CCC(C2=CC=CC=C22)=C1C2C1=CC=CC=C1 WFXURHIXPXVPGM-UHFFFAOYSA-N 0.000 description 1
- TYCOFFBAZNSQOJ-UHFFFAOYSA-N 2-[4-(3-fluorophenyl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC(F)=C1 TYCOFFBAZNSQOJ-UHFFFAOYSA-N 0.000 description 1
- XKSAJZSJKURQRX-UHFFFAOYSA-N 2-acetyloxy-5-(4-fluorophenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(OC(=O)C)=CC=C1C1=CC=C(F)C=C1 XKSAJZSJKURQRX-UHFFFAOYSA-N 0.000 description 1
- PYSICVOJSJMFKP-UHFFFAOYSA-N 3,5-dibromo-2-chloropyridine Chemical compound ClC1=NC=C(Br)C=C1Br PYSICVOJSJMFKP-UHFFFAOYSA-N 0.000 description 1
- SRGKFVAASLQVBO-UHFFFAOYSA-N 3-(4-bromophenyl)-n,n-dimethyl-3-pyridin-2-ylpropan-1-amine;but-2-enedioic acid Chemical compound OC(=O)C=CC(O)=O.C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Br)C=C1 SRGKFVAASLQVBO-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- JGKJMBOJWVAMIJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-1-methylcyclohexan-1-ol;hydrate Chemical compound O.CC(C)(O)C1CCC(C)(O)CC1 JGKJMBOJWVAMIJ-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical class C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 description 1
- DBAKFASWICGISY-BTJKTKAUSA-N Chlorpheniramine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 DBAKFASWICGISY-BTJKTKAUSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- DBAKFASWICGISY-DASCVMRKSA-N Dexchlorpheniramine maleate Chemical compound OC(=O)\C=C/C(O)=O.C1([C@H](CCN(C)C)C=2N=CC=CC=2)=CC=C(Cl)C=C1 DBAKFASWICGISY-DASCVMRKSA-N 0.000 description 1
- KBAUFVUYFNWQFM-UHFFFAOYSA-N Doxylamine succinate Chemical compound OC(=O)CCC(O)=O.C=1C=CC=NC=1C(C)(OCCN(C)C)C1=CC=CC=C1 KBAUFVUYFNWQFM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- SRGKFVAASLQVBO-BTJKTKAUSA-N brompheniramine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Br)C=C1 SRGKFVAASLQVBO-BTJKTKAUSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- RBNWAMSGVWEHFP-UHFFFAOYSA-N cis-p-Menthan-1,8-diol Natural products CC(C)(O)C1CCC(C)(O)CC1 RBNWAMSGVWEHFP-UHFFFAOYSA-N 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 1
- 229960000616 diflunisal Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 1
- 229960001395 fenbufen Drugs 0.000 description 1
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 description 1
- 229960001419 fenoprofen Drugs 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229950007979 flufenisal Drugs 0.000 description 1
- 229950001284 fluprofen Drugs 0.000 description 1
- 229960002390 flurbiprofen Drugs 0.000 description 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019534 high fructose corn syrup Nutrition 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 1
- 229960003464 mefenamic acid Drugs 0.000 description 1
- 238000006386 neutralization reaction Methods 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
- 239000000049 pigment Substances 0.000 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229940100474 polyethylene glycol 1450 Drugs 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- UZXRQGSKGNYWCP-UHFFFAOYSA-M potassium 4-hydroxy-3-methoxybenzenesulfonate hydrate Chemical compound O.[K+].COc1cc(ccc1O)S([O-])(=O)=O UZXRQGSKGNYWCP-UHFFFAOYSA-M 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940083542 sodium Drugs 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000001334 starch sodium octenyl succinate Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960000894 sulindac Drugs 0.000 description 1
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
- 229960004492 suprofen Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229960002044 tolmetin sodium Drugs 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 229960003414 zomepirac Drugs 0.000 description 1
- ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/380,540 US5616621A (en) | 1995-01-30 | 1995-01-30 | Taste masking liquids |
| PCT/US1996/000577 WO1996023486A1 (en) | 1995-01-30 | 1996-01-16 | Taste masking liquids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO973480D0 NO973480D0 (no) | 1997-07-29 |
| NO973480L NO973480L (no) | 1997-09-29 |
| NO322789B1 true NO322789B1 (no) | 2006-12-11 |
Family
ID=23501566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19973480A NO322789B1 (no) | 1995-01-30 | 1997-07-29 | Farmasoytisk akseptabel smaksmaskerende flytende eksipientbase, farmasoytisk blanding inneholdende den, samt en fremgangsmate for smaksmaskering ved hjelp av eksipientbasen |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5616621A (ko) |
| EP (1) | EP0806939B1 (ko) |
| KR (1) | KR100439090B1 (ko) |
| CN (1) | CN1136837C (ko) |
| AT (1) | ATE222095T1 (ko) |
| AU (1) | AU698718B2 (ko) |
| BR (1) | BR9606863A (ko) |
| CA (1) | CA2211677C (ko) |
| DE (1) | DE69622991T2 (ko) |
| DK (1) | DK0806939T3 (ko) |
| ES (1) | ES2180735T3 (ko) |
| FI (1) | FI119724B (ko) |
| IS (1) | IS1971B (ko) |
| NO (1) | NO322789B1 (ko) |
| NZ (1) | NZ302009A (ko) |
| PT (1) | PT806939E (ko) |
| UA (1) | UA59336C2 (ko) |
| WO (1) | WO1996023486A1 (ko) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL108366A (en) * | 1993-03-11 | 1999-11-30 | Taro Vit Ind Ltd | Semi-solid pharmaceutical compounds and a device for their use |
| AUPN862596A0 (en) * | 1996-03-12 | 1996-04-04 | F.H. Faulding & Co. Limited | Pharmaceutical compositions |
| US5849267A (en) * | 1997-05-20 | 1998-12-15 | Colgate-Palmolive Company | Stable desensitizing antitartar dentifrice |
| US6287594B1 (en) * | 1998-01-20 | 2001-09-11 | Edward S. Wilson | Oral liquid compositions |
| US6365180B1 (en) * | 1998-01-20 | 2002-04-02 | Glenn A. Meyer | Oral liquid compositions |
| US6071523A (en) * | 1998-06-03 | 2000-06-06 | Taro Pharmaceuticals Industries, Ltd. | Spill resistant pharmaceutical compositions in semi-solid form |
| USH2044H1 (en) * | 1998-11-02 | 2002-09-03 | Mcneil-Ppc, Inc. | Container with retaining member |
| US6846495B2 (en) | 1999-01-11 | 2005-01-25 | The Procter & Gamble Company | Compositions having improved delivery of actives |
| US20020086878A1 (en) * | 1999-01-11 | 2002-07-04 | Douglas Joseph Dobrozsi | Compositions having improved stability |
| US20020082307A1 (en) * | 1999-01-11 | 2002-06-27 | Dobrozsi Douglas Joseph | Compositions having improved stability |
| US6911214B2 (en) * | 2000-09-05 | 2005-06-28 | Abbott Laboratories | Flavoring systems for pharmaceutical compositions and methods of making such compositions |
| AU2002220248A1 (en) * | 2000-11-06 | 2002-05-15 | Andrx Pharmaceuticals, Inc. | Once a day antihistamine and decongestant formulation |
| US6391886B1 (en) | 2000-12-04 | 2002-05-21 | The Procter & Gamble Company | Oral compositions having improved consumer aesthetics |
| US20030235618A1 (en) * | 2001-10-22 | 2003-12-25 | Taro Pharmaceutical Industries Ltd. | Taste masking spill-resistant formulation |
| ATE505183T1 (de) * | 2001-10-22 | 2011-04-15 | Taro Pharma Ind | Den geschmack verdeckende auslaufsichere formulierung |
| US20050143471A1 (en) * | 2001-10-22 | 2005-06-30 | Shen Gao | Taste masking spill-resistant formulation |
| US7101572B2 (en) * | 2001-12-07 | 2006-09-05 | Unilab Pharmatech, Ltd. | Taste masked aqueous liquid pharmaceutical composition |
| EP1558931B1 (en) * | 2002-11-04 | 2007-06-13 | Transform Pharmaceuticals, Inc. | Analysis of pharmaceutical solubility and stability |
| US8092831B2 (en) * | 2002-11-08 | 2012-01-10 | Andrx Pharmaceuticals, Llc | Antihistamine and decongestant system |
| US20050137262A1 (en) * | 2003-12-22 | 2005-06-23 | Hu Patrick C. | Highly concentrated pourable aqueous solutions of potassium ibuprofen, their preparation and their uses |
| US8728449B2 (en) * | 2005-01-22 | 2014-05-20 | Monosol Llc | Water-soluble film article having salt layer, and method of making the same |
| US20070036859A1 (en) * | 2005-08-11 | 2007-02-15 | Perry Ronald L | Sustained release antihistamine and decongestant composition |
| US8940796B2 (en) | 2006-02-21 | 2015-01-27 | Wyeth Llc | Phenylephrine liquid formulations |
| US20080014274A1 (en) * | 2006-07-14 | 2008-01-17 | Wyeth | Enhanced stability phenylephrine liquid compositions |
| PE20081596A1 (es) | 2007-03-28 | 2009-02-05 | Apotex Technologies Inc | Derivados fluorinados de deferiprona |
| CA2925175A1 (en) | 2007-10-12 | 2009-04-16 | Novartis Ag | Compositions comprising sphingosine 1 phosphate (s1p) receptor modulators |
| BRPI0819338A2 (pt) * | 2007-11-21 | 2015-05-19 | Procter & Gamble | Preparações, métodos e kits úteis para o tratamento de tosse |
| US8362083B2 (en) * | 2008-01-15 | 2013-01-29 | C.B. Fleet Company Inc. | Taste-masked docusate compositions |
| CA2722393A1 (en) * | 2008-04-25 | 2009-10-29 | Apotex Technologies Inc. | Liquid formulation for deferiprone with palatable taste |
| EA020976B1 (ru) | 2009-07-03 | 2015-03-31 | Апотекс Текнолоджиз Инк. | Фторированные производные 3-гидроксипиридин-4-онов и способы их использования |
| WO2014149939A1 (en) * | 2013-03-15 | 2014-09-25 | Novartis Consumer Health Inc. | Dye free liquid therapeutic solution |
| SG11201507369WA (en) * | 2013-03-15 | 2015-10-29 | Novartis Consumer Health Inc | Dye free liquid therapeutic solution |
| CA2919892C (en) | 2013-08-12 | 2019-06-18 | Pharmaceutical Manufacturing Research Services, Inc. | Extruded immediate release abuse deterrent pill |
| US9492444B2 (en) | 2013-12-17 | 2016-11-15 | Pharmaceutical Manufacturing Research Services, Inc. | Extruded extended release abuse deterrent pill |
| US10172797B2 (en) | 2013-12-17 | 2019-01-08 | Pharmaceutical Manufacturing Research Services, Inc. | Extruded extended release abuse deterrent pill |
| AU2015290098B2 (en) | 2014-07-17 | 2018-11-01 | Pharmaceutical Manufacturing Research Services, Inc. | Immediate release abuse deterrent liquid fill dosage form |
| AU2015336065A1 (en) | 2014-10-20 | 2017-05-04 | Pharmaceutical Manufacturing Research Services, Inc. | Extended release abuse deterrent liquid fill dosage form |
| US11234897B2 (en) | 2017-03-27 | 2022-02-01 | DXM Pharmaceutical, Inc. | Packaged multi-dose liquid dextromethorphan hydrobromide formulation |
| CN110279695B (zh) * | 2019-08-07 | 2022-04-08 | 北京博智绿洲医药科技有限公司 | 一种治疗流涕、鼻塞等感冒症状的药物组合物及其制备方法和用途 |
| WO2024023785A1 (en) | 2022-07-29 | 2024-02-01 | Berlia Sushma Paul | A stable pharmaceutical oral liquid formulation of an antispasmodic agent |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3449498A (en) * | 1965-11-18 | 1969-06-10 | Ciba Geigy Corp | Analgesic compositions of a 4-aminoal-kylamino-quinazoline and 1-amino-alkoxybenzimidazole |
| US4453979A (en) * | 1983-03-23 | 1984-06-12 | Lever Brothers Company | Dispersion of hydrophilic gums to form non-swelling aqueous alcoholic mixtures |
| US4882159A (en) * | 1985-12-20 | 1989-11-21 | Warner Lambert Co. | Confectionery delivery system for appetite suppressants |
| US4882156A (en) * | 1985-12-20 | 1989-11-21 | Warner Lambert Co. | Confectionery delivery system for expectorants |
| US4778676A (en) * | 1985-12-20 | 1988-10-18 | Warner-Lambert Company | Confectionery delivery system for actives |
| US4882155A (en) * | 1985-12-20 | 1989-11-21 | Warner Lambert Co. | Confectionery delivery system for antiarrhythmics |
| US4882154A (en) * | 1985-12-20 | 1989-11-21 | Warner Lambert Co. | Confectionery delivery system for mineral supplements |
| US4882158A (en) * | 1985-12-20 | 1989-11-21 | Warner Lambert Co. | Confectionery delivery system for decongestants |
| US4879108A (en) * | 1985-12-20 | 1989-11-07 | Warner-Lambert Company | Confectionery delivery system for antipyretics |
| US4882157A (en) * | 1985-12-20 | 1989-11-21 | Yang Robert K | Confectionery delivery system for anti-cholesterolemics |
| US4882152A (en) * | 1985-12-20 | 1989-11-21 | Yang Robert K | Confectionery delivery system for laxatives, vitamins and antacids |
| US4882153A (en) * | 1985-12-20 | 1989-11-21 | Warner Lambert Co. | Confectionery delivery system for antitussives |
| US5194464A (en) * | 1988-09-27 | 1993-03-16 | Takeda Chemical Industries, Ltd. | Enteric film and preparatoin thereof |
| US5260073A (en) * | 1990-05-21 | 1993-11-09 | Norwich Eaton Pharmaceuticals, Inc. | Use of phenylpropanolamine as a mucus secretogogue in the upper airways |
| US5183829A (en) * | 1991-09-27 | 1993-02-02 | Applied Analytical Industries, Inc. | Oral liquid compositions of non-steroidal anti-inflammatory drugs |
| IL108366A (en) * | 1993-03-11 | 1999-11-30 | Taro Vit Ind Ltd | Semi-solid pharmaceutical compounds and a device for their use |
-
1995
- 1995-01-30 US US08/380,540 patent/US5616621A/en not_active Expired - Lifetime
-
1996
- 1996-01-16 NZ NZ302009A patent/NZ302009A/xx not_active IP Right Cessation
- 1996-01-16 DE DE69622991T patent/DE69622991T2/de not_active Expired - Fee Related
- 1996-01-16 EP EP96903512A patent/EP0806939B1/en not_active Expired - Lifetime
- 1996-01-16 CA CA002211677A patent/CA2211677C/en not_active Expired - Fee Related
- 1996-01-16 AU AU47576/96A patent/AU698718B2/en not_active Ceased
- 1996-01-16 CN CNB961926775A patent/CN1136837C/zh not_active Expired - Fee Related
- 1996-01-16 UA UA97084411A patent/UA59336C2/uk unknown
- 1996-01-16 DK DK96903512T patent/DK0806939T3/da active
- 1996-01-16 PT PT96903512T patent/PT806939E/pt unknown
- 1996-01-16 KR KR1019970705168A patent/KR100439090B1/ko not_active IP Right Cessation
- 1996-01-16 BR BR9606863A patent/BR9606863A/pt not_active IP Right Cessation
- 1996-01-16 WO PCT/US1996/000577 patent/WO1996023486A1/en active IP Right Grant
- 1996-01-16 ES ES96903512T patent/ES2180735T3/es not_active Expired - Lifetime
- 1996-01-16 AT AT96903512T patent/ATE222095T1/de not_active IP Right Cessation
-
1997
- 1997-07-29 IS IS4534A patent/IS1971B/is unknown
- 1997-07-29 NO NO19973480A patent/NO322789B1/no not_active IP Right Cessation
- 1997-07-29 FI FI973147A patent/FI119724B/fi active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| FI973147A0 (fi) | 1997-07-29 |
| DK0806939T3 (da) | 2002-12-02 |
| AU4757696A (en) | 1996-08-21 |
| DE69622991T2 (de) | 2003-04-10 |
| CA2211677C (en) | 2008-03-18 |
| CN1136837C (zh) | 2004-02-04 |
| NZ302009A (en) | 1998-12-23 |
| NO973480D0 (no) | 1997-07-29 |
| NO973480L (no) | 1997-09-29 |
| ATE222095T1 (de) | 2002-08-15 |
| EP0806939A1 (en) | 1997-11-19 |
| IS4534A (is) | 1997-07-29 |
| UA59336C2 (uk) | 2003-09-15 |
| CN1179098A (zh) | 1998-04-15 |
| WO1996023486A1 (en) | 1996-08-08 |
| FI119724B (fi) | 2009-02-27 |
| CA2211677A1 (en) | 1996-08-08 |
| PT806939E (pt) | 2002-11-29 |
| BR9606863A (pt) | 1997-12-23 |
| KR19980701772A (ko) | 1998-06-25 |
| AU698718B2 (en) | 1998-11-05 |
| IS1971B (is) | 2004-12-15 |
| EP0806939B1 (en) | 2002-08-14 |
| DE69622991D1 (de) | 2002-09-19 |
| FI973147A (fi) | 1997-09-29 |
| KR100439090B1 (ko) | 2004-09-08 |
| MX9705724A (es) | 1997-11-29 |
| US5616621A (en) | 1997-04-01 |
| ES2180735T3 (es) | 2003-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |