NZ196658A - Antiphlogistic analgesic pressure-sensitive adhesive containing indomethacin,an acrylate copolymer and an absorption assistant - Google Patents
Antiphlogistic analgesic pressure-sensitive adhesive containing indomethacin,an acrylate copolymer and an absorption assistantInfo
- Publication number
- NZ196658A NZ196658A NZ196658A NZ19665881A NZ196658A NZ 196658 A NZ196658 A NZ 196658A NZ 196658 A NZ196658 A NZ 196658A NZ 19665881 A NZ19665881 A NZ 19665881A NZ 196658 A NZ196658 A NZ 196658A
- Authority
- NZ
- New Zealand
- Prior art keywords
- acrylate
- antiphlogistic analgesic
- adhesive according
- indomethacin
- copolymer
- Prior art date
Links
- 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 title claims description 130
- 229960000905 indomethacin Drugs 0.000 title claims description 65
- 230000001741 anti-phlogistic effect Effects 0.000 title claims description 40
- 239000002260 anti-inflammatory agent Substances 0.000 title claims description 39
- 230000000202 analgesic effect Effects 0.000 title claims description 37
- 238000010521 absorption reaction Methods 0.000 title claims description 33
- 229920001577 copolymer Polymers 0.000 title claims description 28
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims description 22
- 230000001070 adhesive effect Effects 0.000 claims description 66
- 239000000853 adhesive Substances 0.000 claims description 57
- 239000000178 monomer Substances 0.000 claims description 27
- 239000010410 layer Substances 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 14
- -1 2-hydroxypropyl Chemical group 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 239000012790 adhesive layer Substances 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 claims description 2
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 claims description 2
- IUPSARVXBUSQKA-UHFFFAOYSA-N 2-hydroxyhexyl 2-methylprop-2-enoate Chemical compound CCCCC(O)COC(=O)C(C)=C IUPSARVXBUSQKA-UHFFFAOYSA-N 0.000 claims description 2
- FYAWPPXBNNWJRK-UHFFFAOYSA-N 2-hydroxyhexyl prop-2-enoate Chemical compound CCCCC(O)COC(=O)C=C FYAWPPXBNNWJRK-UHFFFAOYSA-N 0.000 claims description 2
- FQLZCZIQXBTZGB-UHFFFAOYSA-N 2-hydroxypentyl prop-2-enoate Chemical compound CCCC(O)COC(=O)C=C FQLZCZIQXBTZGB-UHFFFAOYSA-N 0.000 claims description 2
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 150000001278 adipic acid derivatives Chemical class 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- SCFQUKBBGYTJNC-UHFFFAOYSA-N heptyl prop-2-enoate Chemical compound CCCCCCCOC(=O)C=C SCFQUKBBGYTJNC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002400 hexanoic acid esters Chemical class 0.000 claims description 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 2
- UACSZOWTRIJIFU-UHFFFAOYSA-N hydroxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCO UACSZOWTRIJIFU-UHFFFAOYSA-N 0.000 claims description 2
- GJIDOLBZYSCZRX-UHFFFAOYSA-N hydroxymethyl prop-2-enoate Chemical compound OCOC(=O)C=C GJIDOLBZYSCZRX-UHFFFAOYSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- MDYPDLBFDATSCF-UHFFFAOYSA-N nonyl prop-2-enoate Chemical compound CCCCCCCCCOC(=O)C=C MDYPDLBFDATSCF-UHFFFAOYSA-N 0.000 claims description 2
- 229940065472 octyl acrylate Drugs 0.000 claims description 2
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 2
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 claims description 2
- 150000003329 sebacic acid derivatives Chemical class 0.000 claims description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
- ZWMJUBVSXUPLKD-UHFFFAOYSA-N 2-hydroxypentyl 2-methylprop-2-enoate Chemical compound CCCC(O)COC(=O)C(C)=C ZWMJUBVSXUPLKD-UHFFFAOYSA-N 0.000 claims 1
- 241001125671 Eretmochelys imbricata Species 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- 230000003578 releasing effect Effects 0.000 description 13
- 229920006243 acrylic copolymer Polymers 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 206010030113 Oedema Diseases 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 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 6
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 6
- 239000002674 ointment Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 235000010418 carrageenan Nutrition 0.000 description 5
- 229920001525 carrageenan Polymers 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 230000001629 suppression Effects 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 239000011344 liquid material Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920001342 Bakelite® Polymers 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000004637 bakelite Substances 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 229940031578 diisopropyl adipate Drugs 0.000 description 2
- 229940031569 diisopropyl sebacate Drugs 0.000 description 2
- XFKBBSZEQRFVSL-UHFFFAOYSA-N dipropan-2-yl decanedioate Chemical compound CC(C)OC(=O)CCCCCCCCC(=O)OC(C)C XFKBBSZEQRFVSL-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 101100119767 Caenorhabditis elegans fat-4 gene Proteins 0.000 description 1
- 101100468762 Caenorhabditis elegans ric-3 gene Proteins 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 206010034464 Periarthritis Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 206010041591 Spinal osteoarthritis Diseases 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000037374 absorbed through the skin Effects 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 150000003097 polyterpenes Chemical class 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- XYSQXZCMOLNHOI-UHFFFAOYSA-N s-[2-[[4-(acetylsulfamoyl)phenyl]carbamoyl]phenyl] 5-pyridin-1-ium-1-ylpentanethioate;bromide Chemical compound [Br-].C1=CC(S(=O)(=O)NC(=O)C)=CC=C1NC(=O)C1=CC=CC=C1SC(=O)CCCC[N+]1=CC=CC=C1 XYSQXZCMOLNHOI-UHFFFAOYSA-N 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 208000005801 spondylosis Diseases 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
- A61K9/7061—Polyacrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/58—Adhesives
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Hematology (AREA)
- Materials Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55153407A JPS5843368B2 (ja) | 1980-10-30 | 1980-10-30 | 消炎鎮痛貼付剤 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ196658A true NZ196658A (en) | 1984-07-31 |
Family
ID=15561807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ196658A NZ196658A (en) | 1980-10-30 | 1981-03-27 | Antiphlogistic analgesic pressure-sensitive adhesive containing indomethacin,an acrylate copolymer and an absorption assistant |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4390520A (enExample) |
| JP (1) | JPS5843368B2 (enExample) |
| AT (1) | AT379951B (enExample) |
| AU (1) | AU539237B2 (enExample) |
| BE (1) | BE888156A (enExample) |
| CA (1) | CA1188613A (enExample) |
| CH (1) | CH651213A5 (enExample) |
| DE (1) | DE3111550C2 (enExample) |
| ES (1) | ES8206183A1 (enExample) |
| FR (1) | FR2493144A1 (enExample) |
| GB (1) | GB2086224B (enExample) |
| IT (1) | IT1218260B (enExample) |
| NL (1) | NL184999C (enExample) |
| NZ (1) | NZ196658A (enExample) |
| SE (1) | SE448063B (enExample) |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57140711A (en) * | 1981-02-26 | 1982-08-31 | Teika Seiyaku Kk | Poultice for anti-inflammatory and analgesic use and its preparation |
| GB2105990B (en) * | 1981-08-27 | 1985-06-19 | Nitto Electric Ind Co | Adhesive skin patches |
| DE3205504C2 (de) * | 1982-02-16 | 1983-12-01 | Dolorgiet Gmbh & Co Kg, 5300 Bonn | Äußerlich anwendbares, Ibuprofen enthaltendes Arzneimittel |
| US4608249A (en) * | 1982-11-02 | 1986-08-26 | Nitto Electric Industrial Co., Ltd. | Hydrophilic therapeutic material |
| DE3476550D1 (en) * | 1983-07-21 | 1989-03-09 | Troponwerke Gmbh & Co Kg | Thermoplastics containing antiphlogistics |
| JPS60158561U (ja) * | 1984-03-30 | 1985-10-22 | 株式会社東芝 | 食器乾燥器 |
| JPS60164362U (ja) * | 1984-04-10 | 1985-10-31 | 株式会社東芝 | 食器乾燥器 |
| US5855908A (en) * | 1984-05-01 | 1999-01-05 | University Of Utah Research Foundation | Non-dissolvable drug-containing dosage-forms for use in the transmucosal delivery of a drug to a patient |
| US4863737A (en) * | 1985-05-01 | 1989-09-05 | University Of Utah | Compositions and methods of manufacture of compressed powder medicaments |
| US4725439A (en) * | 1984-06-29 | 1988-02-16 | Alza Corporation | Transdermal drug delivery device |
| US4704282A (en) * | 1984-06-29 | 1987-11-03 | Alza Corporation | Transdermal therapeutic system having improved delivery characteristics |
| US4824676A (en) * | 1984-10-11 | 1989-04-25 | Schering Corporation | Physiological means of enhancing transdermal delivery of drugs |
| US5008111A (en) * | 1984-10-11 | 1991-04-16 | Schering Corporation | Physiological means of enhancing transdermal delivery of drugs |
| AU563054B2 (en) * | 1984-10-24 | 1987-06-25 | Sekisui Kagaku Kogyo Kabushiki Kaisha | Percutaneous tape of isdn |
| ATE77962T1 (de) * | 1985-02-25 | 1992-07-15 | Univ Rutgers | Dosierungssystem fuer transdermale absorption von arzneimittelwirkstoffen. |
| US4751087A (en) * | 1985-04-19 | 1988-06-14 | Riker Laboratories, Inc. | Transdermal nitroglycerin delivery system |
| EP0200508B1 (en) * | 1985-04-27 | 1991-10-02 | Nitto Denko Corporation | Adhesive oral bandages and oral pharmaceutical preparations |
| US4671953A (en) * | 1985-05-01 | 1987-06-09 | University Of Utah Research Foundation | Methods and compositions for noninvasive administration of sedatives, analgesics, and anesthetics |
| US5122127A (en) * | 1985-05-01 | 1992-06-16 | University Of Utah | Apparatus and methods for use in administering medicaments by direct medicament contact to mucosal tissues |
| US5288497A (en) * | 1985-05-01 | 1994-02-22 | The University Of Utah | Compositions of oral dissolvable medicaments |
| US5132114A (en) * | 1985-05-01 | 1992-07-21 | University Of Utah Research Foundation | Compositions and methods of manufacture of compressed powder medicaments |
| US4885173A (en) * | 1985-05-01 | 1989-12-05 | University Of Utah | Methods and compositions for noninvasive dose-to-effect administration of drugs with cardiovascular or renal vascular activities |
| EP0223524B1 (en) * | 1985-11-08 | 1991-10-23 | Nitto Denko Corporation | Use of adhesive dermal bandages and dermal percutaneous preparations |
| US4765974A (en) * | 1985-12-24 | 1988-08-23 | Nitto Electric Industrial Co., Ltd. | Preparation for percutaneous administration |
| US5560922A (en) * | 1986-05-30 | 1996-10-01 | Rutgers, The State University Of New Jersey | Transdermal absorption dosage unit using a polyacrylate adhesive polymer and process |
| US4906475A (en) * | 1988-02-16 | 1990-03-06 | Paco Pharmaceutical Services | Estradiol transdermal delivery system |
| US5223261A (en) * | 1988-02-26 | 1993-06-29 | Riker Laboratories, Inc. | Transdermal estradiol delivery system |
| JP2931002B2 (ja) * | 1988-02-26 | 1999-08-09 | ライカー ラボラトリース インコーポレーテッド | 皮膚透過エストラジオールデリバリーシステム |
| US5474783A (en) | 1988-03-04 | 1995-12-12 | Noven Pharmaceuticals, Inc. | Solubility parameter based drug delivery system and method for altering drug saturation concentration |
| US5656286A (en) | 1988-03-04 | 1997-08-12 | Noven Pharmaceuticals, Inc. | Solubility parameter based drug delivery system and method for altering drug saturation concentration |
| DE3823070A1 (de) * | 1988-07-07 | 1990-02-22 | Kettelhack Riker Pharma Gmbh | Selbstklebendes heftpflaster |
| DE3843557A1 (de) * | 1988-12-23 | 1990-06-28 | Beiersdorf Ag | Transdermales therapeutisches system zur verabreichung von clenbuterol |
| US5061724A (en) * | 1989-07-18 | 1991-10-29 | Sheldon Gertner | Method for treating arthritically inflamed body joints, particularly joints having gouty arthritis |
| US5252334A (en) * | 1989-09-08 | 1993-10-12 | Cygnus Therapeutic Systems | Solid matrix system for transdermal drug delivery |
| CA2065311C (en) * | 1989-09-08 | 2000-01-11 | Chia-Ming Chiang | Solid matrix system for transdermal drug delivery |
| DE69010317T3 (de) * | 1989-12-28 | 2000-10-12 | Nitto Denko Corp., Ibaraki | Acrylgel und seine Herstellung. |
| US5298258A (en) * | 1989-12-28 | 1994-03-29 | Nitto Denko Corporation | Acrylic oily gel bioadhesive material and acrylic oily gel preparation |
| DE4020144A1 (de) * | 1990-06-25 | 1992-01-09 | Lohmann Therapie Syst Lts | Pflaster mit hohem gehalt an weichmachenden inhaltsstoffen |
| JP2507158B2 (ja) * | 1990-08-23 | 1996-06-12 | 積水化学工業株式会社 | 経皮吸収製剤 |
| GB9021674D0 (en) * | 1990-10-05 | 1990-11-21 | Ethical Pharma Ltd | Transdermal device |
| ATE126434T1 (de) * | 1991-06-10 | 1995-09-15 | Sanol Arznei Schwarz Gmbh | Nitroglycerin-pflaster und verfahren zu seiner herstellung. |
| JP2960832B2 (ja) * | 1992-05-08 | 1999-10-12 | ペルマテック テクノロジー アクチェンゲゼルシャフト | エストラジオールの投与システム |
| GB2273044B (en) * | 1992-12-02 | 1997-04-09 | Pacific Chem Co Ltd | Medicinal patches for percutaneous administration |
| JP2569396B2 (ja) * | 1992-12-04 | 1997-01-08 | 株式会社太平洋 | 経皮投与型薬物用貼付剤 |
| DE4416928C1 (de) * | 1994-05-13 | 1995-08-17 | Lohmann Gmbh & Co Kg | Medizinische Haftklebemasse mit hoher Wasserdampfdurchlässigkeit und hoher Klebkraft auf trockener menschlicher Haut sowie bei starker Transpiration, Verfahren zu seiner Herstellung und seine Verwendung |
| DE19738855C2 (de) * | 1997-09-05 | 2001-01-04 | Lohmann Therapie Syst Lts | Transdermales therapeutisches System mit haftklebender Reservoirschicht und unidirektional elastischer Rückschicht |
| DE19830649C2 (de) * | 1998-07-09 | 2003-04-10 | Lohmann Therapie Syst Lts | Topisches Pflaster mit nichtsteroidalen Antirheumatika mit Säuregruppe |
| US20030170195A1 (en) * | 2000-01-10 | 2003-09-11 | Noven Pharmaceuticals, Inc. | Compositions and methods for drug delivery |
| EP1061900B2 (en) * | 1999-01-14 | 2008-07-09 | Noven Pharmaceuticals, Inc. | Dermal compositions |
| WO2000051575A1 (en) * | 1999-03-01 | 2000-09-08 | Amarin Technologies S.A. | Transdermal device comprising non-steroidal anti-inflammatory drugs incorporated in acrylic adhesive polymer matrix |
| JP4841781B2 (ja) * | 1999-11-24 | 2011-12-21 | アジル・セラピューティクス・インコーポレイテッド | 改良された経皮的避妊薬送達系および方法 |
| US7384650B2 (en) | 1999-11-24 | 2008-06-10 | Agile Therapeutics, Inc. | Skin permeation enhancement composition for transdermal hormone delivery system |
| DE10032537A1 (de) * | 2000-07-05 | 2002-01-31 | Labtec Gmbh | Dermales System, enthaltend 2-(3-Benzophenyl)Propionsäure |
| US20050118247A1 (en) * | 2000-07-05 | 2005-06-02 | Gunter Cordes | Method of making ketoprofen patch delivery system |
| GB0019745D0 (en) * | 2000-08-10 | 2000-09-27 | Univ Surrey | Gene expression element |
| UA85674C2 (ru) * | 2003-03-03 | 2009-02-25 | Крисофикс Аг | Устройство для анальгезирующей иммобилизации при переломах грудной клетки или ребер |
| US8852132B2 (en) * | 2003-03-03 | 2014-10-07 | Chrisofix Ag | Device and method for analgesic immobilization of fractured ribs |
| US8784874B2 (en) * | 2003-09-10 | 2014-07-22 | Noven Pharmaceuticals, Inc. | Multi-layer transdermal drug delivery device |
| EP1682061B1 (en) * | 2003-10-28 | 2017-03-15 | Noven Pharmaceuticals, Inc. | Transdermal drug delivery device |
| JP4579920B2 (ja) * | 2004-06-24 | 2010-11-10 | 興和株式会社 | アトルバスタチン外用剤組成物 |
| WO2006044206A2 (en) | 2004-10-08 | 2006-04-27 | Noven Pharmaceuticals, Inc. | Transdermal drug delivery device including an occlusive backing |
| US20060078602A1 (en) | 2004-10-08 | 2006-04-13 | Noven Pharmaceuticals, Inc. | Device for transdermal administration of drugs including acrylic polymers |
| WO2006041907A2 (en) | 2004-10-08 | 2006-04-20 | Noven Pharmaceuticals, Inc. | Transdermal delivery of estradiol |
| WO2006041908A2 (en) * | 2004-10-08 | 2006-04-20 | Noven Pharmaceuticals, Inc. | Transdermal delivery of estradiol |
| JP5025268B2 (ja) * | 2004-11-10 | 2012-09-12 | 久光製薬株式会社 | 外用製剤及び貼付剤 |
| ES2385737T3 (es) * | 2004-11-10 | 2012-07-31 | Hisamitsu Pharmaceutical Co., Inc. | Fármaco para uso externo y parche adhesivo |
| WO2007046315A1 (ja) * | 2005-10-17 | 2007-04-26 | Nisshin Kyorin Pharmaceutical Co., Ltd. | 皮膚外用剤 |
| JP5085062B2 (ja) * | 2006-07-06 | 2012-11-28 | リンテック株式会社 | 経皮吸収貼付剤 |
| MX2009004358A (es) * | 2006-10-27 | 2009-06-17 | Noven Pharma | Suministro transdermico de derivados polares de cetoprofeno. |
| US8231906B2 (en) | 2008-07-10 | 2012-07-31 | Noven Pharmaceuticals, Inc. | Transdermal estrogen device and delivery |
| EP2506838A1 (en) | 2009-12-01 | 2012-10-10 | Noven Pharmaceuticals, INC. | Transdermal testosterone device and delivery |
| WO2012092165A1 (en) | 2010-12-29 | 2012-07-05 | Noven Pharmaceuticals, Inc. | Transdermal drug delivery system comprising levonorgestrel acetate |
| WO2014106009A1 (en) * | 2012-12-28 | 2014-07-03 | Noven Pharmaceuticals, Inc. | Compositions and methods for transdermal delivery of non-steroidal anti-inflammatory agents |
| CA2896055C (en) | 2012-12-28 | 2021-02-16 | Noven Pharmaceuticals, Inc. | Compositions and methods for transdermal delivery of amphetamine and clonidine |
| AR095259A1 (es) | 2013-03-15 | 2015-09-30 | Noven Pharma | Composiciones y métodos para la administración transdérmica de fármacos de amina terciaria |
| WO2015138919A1 (en) | 2014-03-14 | 2015-09-17 | The University Of North Carolina At Chapel Hill | Small molecules for inhibiting male fertility |
| KR20170125939A (ko) | 2015-03-04 | 2017-11-15 | 노벤 파머수티컬즈, 인코퍼레이티드 | 경피 약물 전달 시스템에 사용하기 위한 올리고머/폴리머 실리콘 유체 |
| WO2017004507A1 (en) | 2015-07-02 | 2017-01-05 | Noven Pharmaceuticals, Inc. | Transdermal drug delivery systems for levonorgestrel and ethinyl estradiol |
| JP7531821B2 (ja) | 2015-11-16 | 2024-08-13 | ノーヴェン ファーマシューティカルズ インコーポレイテッド | 経皮薬物送達システムのための伸縮可能なバッキング層 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1017747B (de) * | 1953-06-10 | 1957-10-17 | Bofors Ab | Fluessiges Verbandmaterial |
| IE31985B1 (en) * | 1967-03-29 | 1973-03-07 | Lilly Co Eli | Medicated adhesive tape |
| US3632740A (en) * | 1968-06-13 | 1972-01-04 | Johnson & Johnson | Topical device for the therapeutic management of dermatological lesions with steroids |
| IT953610B (it) * | 1971-04-05 | 1973-08-10 | Salve Sa | Adesivo sensibile a pressione |
| US3731683A (en) * | 1971-06-04 | 1973-05-08 | Alza Corp | Bandage for the controlled metering of topical drugs to the skin |
| AR207805A1 (es) * | 1975-02-06 | 1976-10-29 | Alza Corp | Substrato apropiado para formar apositos para la dispensacion continua de escopolamina base por via transdermica |
| JPS6059210B2 (ja) * | 1975-05-29 | 1985-12-24 | 帝人株式会社 | 真菌症治療貼付剤の製造法 |
| JPS5218812A (en) * | 1975-07-30 | 1977-02-12 | Hifumi Uchimura | Method of preparing antiinflammatory and analgesic plasters |
| JPS552604A (en) * | 1978-06-20 | 1980-01-10 | Sanwa Kagaku Kenkyusho:Kk | Patch agent consisting mainly of nitroglycerin |
| GB2042888B (en) * | 1979-03-05 | 1983-09-28 | Teijin Ltd | Preparation for administration to the mucosa of the oral or nasal cavity |
| JPS55133310A (en) * | 1979-04-03 | 1980-10-17 | Hisamitsu Pharmaceut Co Inc | Novel paste tape and its production |
| GB2045618B (en) * | 1979-04-03 | 1983-05-11 | Hisamitsu Pharmaceutical Co | Adhesive plaster |
-
1980
- 1980-10-30 JP JP55153407A patent/JPS5843368B2/ja not_active Expired
-
1981
- 1981-03-24 DE DE3111550A patent/DE3111550C2/de not_active Expired
- 1981-03-26 IT IT48110/81A patent/IT1218260B/it active
- 1981-03-26 GB GB8109531A patent/GB2086224B/en not_active Expired
- 1981-03-27 AU AU68835/81A patent/AU539237B2/en not_active Ceased
- 1981-03-27 FR FR8106205A patent/FR2493144A1/fr active Granted
- 1981-03-27 ES ES500815A patent/ES8206183A1/es not_active Expired
- 1981-03-27 NZ NZ196658A patent/NZ196658A/en unknown
- 1981-03-27 CA CA000374033A patent/CA1188613A/en not_active Expired
- 1981-03-27 NL NLAANVRAGE8101518,A patent/NL184999C/xx not_active IP Right Cessation
- 1981-03-27 BE BE0/204284A patent/BE888156A/fr not_active IP Right Cessation
- 1981-03-27 SE SE8101992A patent/SE448063B/sv not_active IP Right Cessation
- 1981-03-27 AT AT0142681A patent/AT379951B/de not_active IP Right Cessation
- 1981-03-27 CH CH2103/81A patent/CH651213A5/de not_active IP Right Cessation
- 1981-03-30 US US06/248,912 patent/US4390520A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU6883581A (en) | 1982-05-06 |
| GB2086224A (en) | 1982-05-12 |
| GB2086224B (en) | 1985-01-16 |
| IT8148110A0 (it) | 1981-03-26 |
| FR2493144A1 (fr) | 1982-05-07 |
| BE888156A (fr) | 1981-07-16 |
| NL184999C (nl) | 1990-01-02 |
| ATA142681A (de) | 1985-08-15 |
| SE8101992L (sv) | 1982-05-01 |
| AU539237B2 (en) | 1984-09-20 |
| DE3111550A1 (de) | 1982-05-19 |
| FR2493144B1 (enExample) | 1984-02-10 |
| SE448063B (sv) | 1987-01-19 |
| CH651213A5 (de) | 1985-09-13 |
| IT1218260B (it) | 1990-04-12 |
| JPS5843368B2 (ja) | 1983-09-27 |
| JPS5775918A (en) | 1982-05-12 |
| NL8101518A (nl) | 1982-05-17 |
| ES500815A0 (es) | 1982-08-16 |
| CA1188613A (en) | 1985-06-11 |
| DE3111550C2 (de) | 1986-06-05 |
| ES8206183A1 (es) | 1982-08-16 |
| NL184999B (nl) | 1989-08-01 |
| US4390520A (en) | 1983-06-28 |
| AT379951B (de) | 1986-03-25 |
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