JPS61167615A - Administration of drug - Google Patents
Administration of drugInfo
- Publication number
- JPS61167615A JPS61167615A JP596185A JP596185A JPS61167615A JP S61167615 A JPS61167615 A JP S61167615A JP 596185 A JP596185 A JP 596185A JP 596185 A JP596185 A JP 596185A JP S61167615 A JPS61167615 A JP S61167615A
- Authority
- JP
- Japan
- Prior art keywords
- film
- drug
- soft segment
- segment
- glycol
- 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.)
- Pending
Links
- 229940079593 drug Drugs 0.000 title claims abstract description 54
- 239000003814 drug Substances 0.000 title claims abstract description 54
- 229920000642 polymer Polymers 0.000 claims abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004202 carbamide Substances 0.000 claims abstract description 4
- 229920001281 polyalkylene Polymers 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 16
- -1 ether glycols Chemical class 0.000 claims description 9
- 238000001647 drug administration Methods 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 36
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 9
- 229920000570 polyether Polymers 0.000 abstract description 6
- 229920003226 polyurethane urea Polymers 0.000 abstract description 6
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 5
- 229920001971 elastomer Polymers 0.000 abstract description 4
- 239000000806 elastomer Substances 0.000 abstract description 4
- 150000002148 esters Chemical class 0.000 abstract description 3
- 239000011148 porous material Substances 0.000 abstract description 3
- 238000013329 compounding Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 17
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 9
- 229960001597 nifedipine Drugs 0.000 description 9
- 238000010586 diagram Methods 0.000 description 8
- 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 8
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 229920006264 polyurethane film Polymers 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229960000905 indomethacin Drugs 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000006085 branching agent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- KCOPMCWPGUZUET-UHFFFAOYSA-N 2-aminoacetate;aminoazanium Chemical compound NN.NCC(O)=O KCOPMCWPGUZUET-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- GGZZISOUXJHYOY-UHFFFAOYSA-N 8-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1O GGZZISOUXJHYOY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- IROWCYIEJAOFOW-UHFFFAOYSA-N DL-Isoprenaline hydrochloride Chemical compound Cl.CC(C)NCC(O)C1=CC=C(O)C(O)=C1 IROWCYIEJAOFOW-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WMTLVUCMBWBYSO-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 WMTLVUCMBWBYSO-UHFFFAOYSA-N 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 239000000006 Nitroglycerin Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 230000009876 antimalignant effect Effects 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 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 description 1
- 229960003291 chlorphenamine Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 229960001193 diclofenac sodium Drugs 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 229940066493 expectorants Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 230000002439 hemostatic effect Effects 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 description 1
- 229950009183 ibufenac Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 1
- 229940018448 isoproterenol hydrochloride Drugs 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 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
- 239000012528 membrane Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- 229960005323 phenoxyethanol Drugs 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
- 230000000704 physical effect Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000874 polytetramethylene terephthalate Polymers 0.000 description 1
- 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 1
- 229960005205 prednisolone Drugs 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】 本発明は新規なる薬剤投与方法忙関する。[Detailed description of the invention] The present invention relates to a new method of drug administration.
本発明は殊忙フィルム状部分を通して、薬物を投与する
新規なる方法に関する。The present invention relates to a new method of administering drugs through a special film section.
従来、薬物を投与する方法として一般に多く用いられる
方法は、鋺剤、カプセル剤、ａ剤。Traditionally, the most commonly used methods of administering drugs are syringes, capsules, and a preparations.
液剤の如き形態を経口的に服用する内用薬、血管、筋肉
、皮膚等への注射薬、坐剤、軟膏、パツ１剤、トローチ
剤の如き外用薬等が知られている。又、薬物を容器状物
の中に封入し、−面を連続孔を形成している多孔性皮膜
にする等により薬物透過性を付与せしめ経皮的に薬物を
投与する剤層も最近注目されて来ており、従来の薬物の
１７３は経皮投与となると言う説も唱えられている状況
にある。本発明者はかかる情勢にかんがみ経皮的に投与
する新規なる薬物投与ンステムについて鋭意検討の結果
、多孔質フィルムなどを用いないきわめて安価な高分子
フィルム材料を通して薬物を徐々に放出する方法を見出
し、本発明に到達した。即ち本発明は、フィルムと、該
フィルム中に、１）る、及び／又は、販フィルム忙接す
る薬剤部分とからなり、該フィルムを通して経皮的に薬
剤を投与する方法において、該フィルムを構成する主た
るボリマーが、ソフトセグメントと、ハードセグメント
から成り、該ソフトセグメントはポリフルキレンエーテ
ルグリコールの一種以上を主成分とし、該ハードセグメ
ントは、ウレア結合、反び／又はウレタン結合、又はエ
ステル結合を有す分子間結合力の強いセグメント部分で
ある事を特徴とする薬剤投与方法である。Internal medicines such as liquid preparations that are taken orally, injections into blood vessels, muscles, skin, etc., and external medicines such as suppositories, ointments, patches, and troches are known. In addition, a drug layer for transdermally administering the drug by enclosing the drug in a container-like object and providing drug permeability by forming a porous film with continuous pores on the negative side has recently attracted attention. As a result, there is a theory that conventional drugs 173 will be administered transdermally. In view of this situation, the inventors of the present invention have conducted intensive studies on a new system for transdermally administering drugs, and have discovered a method for gradually releasing drugs through an extremely inexpensive polymeric film material that does not use porous films. We have arrived at the present invention. That is, the present invention provides a method for transdermally administering a drug through the film, which comprises a film and a drug portion contained in the film and/or in contact with the sales film. The main polymer consists of a soft segment and a hard segment, the soft segment mainly containing one or more polyfulkylene ether glycols, and the hard segment having a urea bond, a urethane bond, or an ester bond. This drug administration method is characterized by segment portions having strong intermolecular binding force.
本発明におけるフィルムはポリウレタンウレア、ポリウ
レタン、ポリエステルエラストマーよりなる群からえら
ばれる。本発明においてソフトセグメントはフィルムを
介して薬剤を投与するに際して薬剤の透過を容易ならし
めるのに不可欠である。かかるソフトセグメントが物理
的な孔を有していないにもかかわらず実用に供し得る程
度まで薬剤を透過す為効果を有している事は実に驚くべ
きことである。本発明はかかる事実に基づき、実用忙供
するに適した特定の組成を見出すことにより達成された
。これらのポリマーの製法は末端が活性である脂肪族ポ
リエーテルからえらばれるソフト成分と、芳香族又は脂
肪族ジイソンアネート類、芳香族ジカルボン酸類とを各
々反応させることを基本とする。The film in the present invention is selected from the group consisting of polyurethaneurea, polyurethane, and polyester elastomer. In the present invention, the soft segment is essential to facilitate the permeation of the drug when administering the drug through the film. It is truly surprising that although such soft segments do not have physical pores, they are effective in permeating drugs to a practical extent. The present invention was achieved based on this fact by finding a specific composition suitable for practical use. The method for producing these polymers is based on reacting a soft component selected from an aliphatic polyether with active terminals with an aromatic or aliphatic diisonanate or an aromatic dicarboxylic acid.
これらのポリウレタンウレア、ポリウレタン。These polyurethane urea, polyurethane.
ポリエステルの構成成分の種類９分子量、ハードセグメ
ントとソフトセグメントの量比、鎖伸長剤９分岐剤、末
端停止剤等の各種添加剤の種類や童の選択は目的とする
フィルム物性に応じて任意に実施し得るものである。具
体的な例を挙げれば、ソフト成分としてのポリエーテル
はポリオキラテトラメチレングリコール、ポリオキシプ
シビレングリコーｌし、ポリエチレングリコール、ポリ
ジエチレングリコール、ポリプロピレングリコールとポ
リエチレングリフールのコポリマーなどが代表的な例と
して挙げられる。The molecular weight of the polyester components, the ratio of the hard segment to the soft segment, the chain extender, the branching agent, the terminal stopper, and other additives can be selected depending on the desired physical properties of the film. It is possible to implement it. To give specific examples, typical examples of polyethers used as soft ingredients include polyoxylatetramethylene glycol, polyoxypsibylene glycol, polyethylene glycol, polydiethylene glycol, and copolymers of polypropylene glycol and polyethylene glycol. It is mentioned as.
凸−ドセグメソトを構成するジイソシアネート化合物の
例としてはジフェニルメタンジイソンアネート、ジフェ
ニルエーテルジインシアネート、トルイレンジイソシア
ネート、メタキッリレンジイソシアネート、ンク四へキ
サジイソシアネート、ヘキサメチレンジイソンアネート
などが代表的例として挙げられる。このハードセグメン
ト中には鎖伸長剤としてエチレングリコール、１−ピレ
ングリフール、テトラメチレングリコール、プルピレン
グリコール、テトラメチレングリコール嘗へキサメチレ
ングリコール。Typical examples of the diisocyanate compound constituting the convex dosegmentation compound include diphenylmethane diisonanate, diphenyl ether diisocyanate, tolylene diisocyanate, methachylylene diisocyanate, tetrahexadiisocyanate, hexamethylene diisonanate, and the like. This hard segment contains ethylene glycol, 1-pyrene glycol, tetramethylene glycol, propylene glycol, tetramethylene glycol and hexamethylene glycol as chain extenders.
ビスーＰ−ＬドロキシエトキンビスフェノールＡ、ジエ
チルアミン、ジイソプロピルアミン。Bisu PL droxyethquin bisphenol A, diethylamine, diisopropylamine.
ヒドラジン、グリシンしドラシト、７ラニンヒドラジド
、トリメチー−ルプジパシトリインシアネート、エチレ
ンジ７ミン、プロピレンジアミン、ヘキサメチレンジア
ミンなどを用い得ル。Hydrazine, glycine hydrazine, 7-lanine hydrazide, trimethylpudipacitrinocyanate, ethylenedi7mine, propylene diamine, hexamethylene diamine, etc. can be used.
又、分岐剤として、グリセリン、トリメチロールプロパ
ン、ペソタエリスリトール等カ添加すれ得る。又、末端
停止剤として、ラウリルフルフール、エチレングリコー
ルモノフェニルエーテル、ジエチレングリフ−ルーモノ
−Ｐ−オクチルフェニルエーテル、ジメチルアミン、ジ
エチルアミンなどの単官能活性水素化合物等が用いられ
得る。Further, as a branching agent, glycerin, trimethylolpropane, pesotaerythritol, etc. may be added. Furthermore, monofunctional active hydrogen compounds such as laurylfurfur, ethylene glycol monophenyl ether, diethylene glycol mono-P-octylphenyl ether, dimethylamine, diethylamine, etc. can be used as the terminal capping agent.
一方、ハードセグメントを構成する芳香族ジカルボン酸
の例としてはテレフタル酸が代表的な例として挙げられ
る。この中忙も第三成分としてインフタル酸、フタル酸
、す７タレンジカルボン酸、ジフェニレジカルボン酸、
ジフェニルスルホンジカルボン酸、セパチン酸、アジピ
ン酸、エチレングリコール、プロピレングリコール！テ
カメチレングリコール、ビス−ヒドロキシエトキンビス
フェニルＡ、ビス−β−ヒドロキシエトキンビスフェノ
ールＳ等が用いられ得、！１６又、前述の如き分岐剤や
末端停止剤も用いられる。これらのポリエステルの重合
は通常。On the other hand, terephthalic acid is a typical example of the aromatic dicarboxylic acid constituting the hard segment. The third component of this medium is inphthalic acid, phthalic acid, 7thalene dicarboxylic acid, diphenyledicarboxylic acid,
Diphenylsulfone dicarboxylic acid, sepatic acid, adipic acid, ethylene glycol, propylene glycol! Tecamethylene glycol, bis-hydroxyethquin bisphenyl A, bis-β-hydroxyethquin bisphenol S, etc. can be used! 16 Also, branching agents and terminal capping agents as described above may also be used. Polymerization of these polyesters is normal.
溶融状態で行うのがこのましく、殊に、前述の如き、ポ
リエステルの重合は高真空下で行なうのが通常であり、
従来公知の適当な触媒や安定剤が好ましく用いられる。It is preferable to carry out the polymerization in the molten state, and in particular, as mentioned above, the polymerization of polyester is usually carried out under high vacuum.
Conventionally known suitable catalysts and stabilizers are preferably used.
触媒の例を単げればポリウレタン化の触媒としては第三
級アミンや、ジブチルチンジオキサイドの如き金属化合
物が例として挙げられ、又、ポリエステル化触媒として
はエステル交換触媒としてアルカリ土類金属の＠酸塩、
例えば酢酸カルシウム、酢酸マグネンウムや酢酸マンガ
ン、酢酸鉄、酢酸亜鉛等が、又重合触媒としてチタニウ
ムテトラブトキサイド、ジブチルチンオキサイド、三識
化アンチモン等が好ましく用いられる。Examples of catalysts include tertiary amines and metal compounds such as dibutyltin dioxide as polyurethanization catalysts, and alkaline earth metals as transesterification catalysts as polyesterification catalysts. acid salt,
For example, calcium acetate, magnenium acetate, manganese acetate, iron acetate, zinc acetate, etc. are preferably used, and as a polymerization catalyst, titanium tetrabutoxide, dibutyltin oxide, antimony trichloride, etc. are preferably used.
本発明において、ポリエーテルよりなるソフトセグメン
トとエステル結合、ウレタン結合。In the present invention, a soft segment made of polyether, an ester bond, and a urethane bond.
ウレア結合から成るハードセグメントの重量組成比は、
ソフトセグメント量が全体の３０〜９８重量％を占める
のが適当であシ殊に５０〜９５重量％、更に好ましくは
５５〜８０重量％の範囲が好適である。The weight composition ratio of the hard segment consisting of urea bonds is
The amount of soft segments is suitably 30 to 98% by weight, particularly 50 to 95% by weight, more preferably 55 to 80% by weight.
かかるポリエーテルエステル、ポリウレタンウレア、ポ
リウレタンのフィルム化は従来公知の適当な方法、例え
ば溶融製膜や溶液製膜が好ましく用いられ得る。かかる
工ｓにおいて、その溶融ポリマー中ないし、溶液ポリマ
ー中に適当な薬剤を存在せしめたり、又、薬剤をそのま
ま又は必要忙応じ適当なマトリックス剤と共に溶液とし
、フィルム上にコートしたり、フィルムとフィルムの間
にはさみ込んだり、更にはフィルムを液状薬剤（通常溶
液状になっている）をケースの少なくとも一面をおおっ
て薬剤がこのフィルム層を通して皮膚に達する様にする
ことも本発明の投与方法の一態様に含まれる。For forming a film from such polyether ester, polyurethane urea, or polyurethane, a conventionally known appropriate method, such as melt casting or solution casting, can be preferably used. In such a process, a suitable drug may be present in the molten polymer or solution polymer, or the drug may be coated on a film as it is or as a solution with a suitable matrix agent as required, or the film may be coated with a solution of the drug as it is or may be mixed with a suitable matrix agent as needed. In the administration method of the present invention, a film may be used to cover at least one side of the case with a liquid drug (usually in the form of a solution) so that the drug reaches the skin through this film layer. Included in one embodiment.
本発明の薬剤投与方法に供し得る薬剤は前述のフィルム
を通過し得るものであれば特に制限はないがその好適な
例を挙げれば、ニトログリセリン、硝搬イソソルバイト
、ニフェジピンなどの循環器用薬；アセトアミノフェン
、フエナセチン、アスピリン、７ミノピリン、スルピリ
ン、フェニルブタジン、メフェナム酸、イブフェナック
、イブフロフェン、インドメタシン。The drugs that can be used in the drug administration method of the present invention are not particularly limited as long as they can pass through the above-mentioned film, but suitable examples include cardiovascular drugs such as nitroglycerin, isosorbite, and nifedipine; Acetaminophen, phenacetin, aspirin, 7 minopyrine, sulpirin, phenylbutadine, mefenamic acid, ibufenac, ibuflofen, indomethacin.
ジクロフェナックナトリウム、１ｇペネシドなどの鎮痛
消炎薬；酪酸しドロコルチゾン、プレドニゾロン、デキ
サメタシン、ベタメタシンなどの消炎スブ゛ロイド薬；
塩酸ジフェンＬドラミン、マレイン陵クロルフェニラミ
ンなどの抗ヒスタミン薬；ベソゾカインなどの局所麻陣
薬；リン酸ジＬドシコデイン、塩酸イソプロテレノール
などの鎮咳去たん薬；イ°／ンユリンなどの血糖降下薬
；その他止血薬、血圧降下薬、鎮静薬、抗悪性腫瘍薬な
どが挙げられる。以下実施例を挙げて具体的に本発明を
更に説明するが本発明は実施例のＸ＜限定されるもので
はない。Analgesic anti-inflammatory drugs such as diclofenac sodium, 1g penecid; anti-inflammatory subroid drugs such as drocortisone butyrate, prednisolone, dexamethacin, betamethacin;
Antihistamines such as diphen-L-doramine hydrochloride and malein-lying chlorpheniramine; topical opiates such as besozocaine; antitussive expectorants such as di-L-dosycodeine phosphate and isoproterenol hydrochloride; hypoglycemic drugs such as I°/Nyulin Other drugs include hemostatic drugs, antihypertensive drugs, sedatives, and anti-malignant tumor drugs. The present invention will be further explained in detail with reference to Examples below, but the present invention is not limited to the following Examples.
実施例におけるηＳｐ／ｃはイソクローフェノール９３
５℃忙おいて測定した還元比粘度である。ηSp/c in Examples is isoclorphenol 93
This is the reduced specific viscosity measured at 5°C.
実施例１
ハードセグメントとしてのジフェニルメタンジインシア
ネート、テトラメチレングリコール成分的３２重量係、
ソフトセグメントとしてのポリテトラメチレングリコー
ル（平均分子量約２０００）成分約６８１ｔ％からなる
ポリウレタン（ηＳｐ／ｅ ＝ ２．２６３ ヲジメチ
ルホルムアミドに溶解して２５チ溶液を作り、これを用
いて乾式法により厚み約２０ミクロンのフィルムを作成
した。このフィルムを用いて、第１図の装置を作成した
。第１図のＡＫは薬物溶液３ｄ。Example 1 Diphenylmethane diincyanate as hard segment, tetramethylene glycol component 32% by weight,
A polyurethane (ηSp/e = 2.263) consisting of about 681 t% of polytetramethylene glycol (average molecular weight about 2000) component as a soft segment was dissolved in dimethylformamide to make a 25% solution, and using this, the thickness was determined by a dry method. A film of approximately 20 microns was created. Using this film, the device shown in Figure 1 was created. AK in Figure 1 is drug solution 3d.
ＢＫは生理食塩水３−を入れ、３７℃において振とうを
行ないウレタンフィルムを透過して生埋食塩水側に移行
した薬物量を暗所で経時的に測定した。薬物としては、
１ｗ／ｖｄニフェジピンエチレングリコール溶ｉ［、ｔ
ｗ９／ｄインドメタシンエチレングリコール溶液、１１
ｍ９／−酪酸Ｌドロコルチゾン溶液を使用した。その結
果を第２図に示した。第２図から明らかなように、ポリ
ウレタンフィルムは、薬物な徐々に透過させる特性を有
する。For BK, physiological saline 3- was added, shaken at 37°C, and the amount of drug that had passed through the urethane film and transferred to the saline side was measured over time in the dark. As a drug,
1w/vd nifedipine ethylene glycol solution i[,t
w9/d indomethacin ethylene glycol solution, 11
m9/- L-drocortisone butyrate solution was used. The results are shown in Figure 2. As is clear from FIG. 2, the polyurethane film has the property of gradually permeating drugs.
実施例２
八−ドセグメシトとしてのポリテトラメチレンテレフタ
レート３８重量％とソフトセグメントとしてのポリオキ
ンテトラメチレングリコール（平均分子量約２０００）
６２重量％のブロック共重合体であり、安定剤としてテ
トラキス−〔メチレン−（３，５−ジー−ブチル−４Ｌ
ドロキシハイドロジンナート）〕メタシンチバガイギー
社；イルガノックス１０１ Ｇ ） ０．８重量％な含
有するポリエーテルエステルエラストマー （ｙｓｐ／
ｃ ＝ ２．５４ ）をクロロホルムに溶解して１０チ
溶液を作シ、これを用いて乾式法によす厚＾約２５ミク
ロンのフィルムを作成した。Example 2 38% by weight of polytetramethylene terephthalate as octa-dosegmesite and polyokinetetramethylene glycol as soft segment (average molecular weight approximately 2000)
It is a block copolymer of 62% by weight and contains tetrakis-[methylene-(3,5-di-butyl-4L) as a stabilizer.
Polyether ester elastomer containing 0.8% by weight (ysp/
c = 2.54) was dissolved in chloroform to prepare a 10% solution, which was used to prepare a film with a thickness of about 25 microns by dry method.
このフィルムをポリウレタンフィルムの代りに使用した
以外は実施例１と同様にして３７℃におけるニフェジピ
ン、インドメタシン、ａ！酸ヒト−コルチゾンの透過量
を測定した。その結果を第３図に示した。第３図から明
らかなようにポリエーテルエステルエリストマーフィル
ムは薬物を徐々に透過させる特性を有する。Example 1 was repeated except that this film was used instead of the polyurethane film, and nifedipine, indomethacin, a! The permeation amount of acid human-cortisone was measured. The results are shown in Figure 3. As is clear from FIG. 3, the polyetherester elastomer film has the property of allowing drugs to gradually permeate.
実施例３
ハードセグメントとしてのジフェニルメタンジイソンア
ネート、ノナメチレンジアミン成分約３４重貴嘩、ソフ
トセグメントとしてのポリテトラメチレングリコール（
平均分子量約２０００）成分的６６％からなるポリウレ
タンウレア（ηｓｐ／ｅ ＝ ２．１４ ）をジメチル
ホルムアミドに溶解してｌ〇−溶液を作り、これを用い
て乾式法により厚み約３０ミクーンのフィルムを作成し
た。このフィルムをポリウレタンフィルムの代りに使用
した以外は実施例１と同様にして３７℃におけるニフェ
ジピン、インドメタンン、酪酸しドロフルチゾンの透過
量を測定した。その結果をｔｓ４図に示した。第４図か
ら明らかなようにポリウレタンウレアフィルムは薬物な
徐々忙透過させる特性を有する。Example 3 Diphenylmethane diisonanate as a hard segment, approximately 34% of nonamethylene diamine component, and polytetramethylene glycol (as a soft segment)
A polyurethane urea (ηsp/e = 2.14) consisting of 66% (average molecular weight approximately 2000) was dissolved in dimethylformamide to prepare a l〇-solution, and this was used to form a film with a thickness of approximately 30 microns by a dry method. Created. The amount of permeation of nifedipine, indomethane, and doroflutisone butyrate at 37° C. was measured in the same manner as in Example 1 except that this film was used instead of the polyurethane film. The results are shown in ts4 diagram. As is clear from FIG. 4, the polyurethane urea film has the property of gradually permeating drugs.
実施例４
ポリウレタンフィルムの厚みを１０／Ｊｍ、６０μＭＬ
＋ １００ｐ？ｌＬ ＊ １３０ｐＷＬＫ した以外
は実施例１と同様にして３７℃におけるニフェジピン、
インドメタシン、酪ｆｉｌｅドジコルチゾンの透過量を
測定した。各透過量から透過速度を求め、透過速度とフ
ィルム厚みとの関係を第５図に示した。なおこの図には
実施例ＩＫおけるポリウレタンフィルムを使用した例も
併記されている。Example 4 Thickness of polyurethane film is 10/Jm, 60μML
+100p? Nifedipine at 37° C. in the same manner as in Example 1 except that 1L * 130 pWLK.
The amount of permeation of indomethacin and dodicortisone was measured. The permeation rate was determined from each amount of permeation, and the relationship between the permeation rate and film thickness is shown in FIG. This figure also shows an example in which a polyurethane film was used in Example IK.
第５図より明らかなようにフィルム厚みなりｓｍするこ
と忙よって、薬物の透過速度を容易に制御できる特性を
有する。As is clear from FIG. 5, the film has the characteristic that the permeation rate of the drug can be easily controlled by controlling the thickness of the film.
実施例５
実施例１の２５％ポリウレタン溶液４６．９と８０１１
９／１７のニフェジピンポリエチレングリコール溶液、
インドメタンンポリエチレングリコール溶液、Ｍ酸ヒト
ａフルチゾンポリエチレングリフール溶液、それぞれ４
１を暗所で混合した。この液を用いて乾式法により厚み
３００４りｐンの薬物含有ポリウレタンフィルムを暗所
で作成した。このフィルムをＪＲ１図の装置にはさみ、
ＢＫ生理食塩水３−を入れ温度３７℃における薬物の放
出量を測定した。その結果を第６図忙示す。また、この
フィルムを室温で放置したところ、フィルム中の薬物が
、フィルム表面にしみ出し、１０日後にはフィルム中の
業物が完全にフィルム表ＷＪＫ出てきた。Example 5 25% polyurethane solution of Example 1 46.9 and 8011
9/17 nifedipine polyethylene glycol solution,
Indomethane polyethylene glycol solution, M acid human a flutisone polyethylene glycol solution, 4 each
1 was mixed in the dark. Using this solution, a drug-containing polyurethane film having a thickness of 300 mm was prepared in a dark place by a dry method. Place this film in the device shown in the JR1 diagram,
BK physiological saline 3- was added and the amount of drug released at a temperature of 37°C was measured. The results are shown in Figure 6. When this film was left at room temperature, the drug in the film oozed out onto the surface of the film, and after 10 days, the drug in the film was completely exposed to the surface of the film.
実施例６
薬物の濃度を２０〜／−くし、その溶媒をポリエチレン
グリフール：エチレングリコール（４：１１３：２１２
：３，１：４）混液にした以外は実施例１と同様にして
３７℃における薬物透過量を測定した。各透過量から透
過速度を求め、透過速度と混合溶媒との関係を第７図に
示した。第７図から明らかなように、ポリエチレングリ
フール・エチレングリコール混合溶媒の比を変えること
Ｋより薬物の透過速度を容易に制御できる。Example 6 The concentration of drug was adjusted to 20~/-, and the solvent was polyethylene glycol: ethylene glycol (4:113:212
:3, 1:4) The amount of drug permeation at 37° C. was measured in the same manner as in Example 1 except that a mixed solution was used. The permeation rate was determined from each amount of permeation, and the relationship between the permeation rate and the mixed solvent is shown in FIG. As is clear from FIG. 7, the drug permeation rate can be easily controlled by changing the ratio of the polyethylene glycol/ethylene glycol mixed solvent.
実施例７
フィルムと生理食塩水との間に・＼アレスマウスの摘出
皮膚をはさみこんだ以外は実施例１と同様にして、フィ
ルム及び皮膚を透過したニフェジピン量を測定した。そ
の結果を第８図に示した。＃！８図から明らかなよ５に
、フィルムを透過したニフェジピンは、 ｌｏｇ ｔｉ
ｍｅ 後、直線的に皮膚を透過する。またその透過速度
は実施例１の結果と等しく、フィルムの透過速度を調整
すること罠より、皮膚からの薬物の吸収を制御できるこ
とが示唆された。Example 7 The amount of nifedipine that permeated through the film and skin was measured in the same manner as in Example 1, except that the excised skin of Ares mouse was sandwiched between the film and physiological saline. The results are shown in FIG. #! It is clear from Figure 8 that the nifedipine that permeated through the film is log ti
After me, it penetrates the skin in a straight line. Moreover, the permeation rate was the same as the result of Example 1, suggesting that the absorption of the drug through the skin can be controlled by adjusting the permeation rate of the film.
第１図は、薬物透過性を測定する装置の説明図である。
第２〜４図は、薬物透過量と透過時間との関係を示す図
である。第５図は、膜の厚みと薬物透過速度との関係を
示す図である。第６図は、薬物放出量と透過時間との関
係を示す図である。第７図は、薬物透過速度と混合溶媒
比との関係を示す図である。第８図は、ニフェジピン透
過量と透過時間との関係を示す図である。
１１２ 因
第３図
邊！＠間（酌量）
第６図
透過」埼ＦＩｌｒ１（時間）FIG. 1 is an explanatory diagram of an apparatus for measuring drug permeability. 2 to 4 are diagrams showing the relationship between drug permeation amount and permeation time. FIG. 5 is a diagram showing the relationship between membrane thickness and drug permeation rate. FIG. 6 is a diagram showing the relationship between drug release amount and permeation time. FIG. 7 is a diagram showing the relationship between drug permeation rate and mixed solvent ratio. FIG. 8 is a diagram showing the relationship between nifedipine permeation amount and permeation time. 112 The third figure! @Ma (extenuating amount) Figure 6 Transmission” SaiFIlr1 (hours)
Claims (1)
ルムに接する薬剤部分とからなり、該フィルムを通して
経皮的に薬剤を投与する方法において、該フィルムを構
成する主たるポリマーが、ソフトセグメントと、ハード
セグメントからなり、該ソフトセグメントはポリアルキ
レンエーテルグリコールの一種以上を主成分とし、該ハ
ードセグメントは、ウレア結合、及び／又はウレタン結
合、又はエステル結合を有す分子間結合力の強いセグメ
ント部分である事を特徴とする薬剤投与方法。A method of administering a drug transdermally through the film, comprising a film and a drug portion in the film and/or in contact with the film, wherein the main polymer constituting the film is a soft segment; The soft segment is composed of a hard segment, and the soft segment is mainly composed of one or more polyalkylene ether glycols, and the hard segment is a segment portion with strong intermolecular bonding strength having a urea bond, a urethane bond, or an ester bond. A drug administration method characterized by certain things.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP596185A JPS61167615A (en) | 1985-01-18 | 1985-01-18 | Administration of drug |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP596185A JPS61167615A (en) | 1985-01-18 | 1985-01-18 | Administration of drug |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61167615A true JPS61167615A (en) | 1986-07-29 |
Family
ID=11625479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP596185A Pending JPS61167615A (en) | 1985-01-18 | 1985-01-18 | Administration of drug |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61167615A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2047456A1 (en) * | 1992-07-31 | 1994-02-16 | Postigo Herrando | Cosmetic compsn. - contains retinoic acid, beta-methasone di-propionate, urea and excipient |
| US5861170A (en) * | 1991-12-20 | 1999-01-19 | Lts Lohmann Therapie-Systeme Gmbh & Co. Kg | Acetylsalicyclic acid-containing transdermal application system for antithrombotic therapy |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5632414A (en) * | 1979-08-28 | 1981-04-01 | Suzuki Nihondou:Kk | Preparation of stretchable clear sticking plaster |
| JPS5738713A (en) * | 1980-08-20 | 1982-03-03 | Nitto Electric Ind Co Ltd | Therapeutic material |
-
1985
- 1985-01-18 JP JP596185A patent/JPS61167615A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5632414A (en) * | 1979-08-28 | 1981-04-01 | Suzuki Nihondou:Kk | Preparation of stretchable clear sticking plaster |
| JPS5738713A (en) * | 1980-08-20 | 1982-03-03 | Nitto Electric Ind Co Ltd | Therapeutic material |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5861170A (en) * | 1991-12-20 | 1999-01-19 | Lts Lohmann Therapie-Systeme Gmbh & Co. Kg | Acetylsalicyclic acid-containing transdermal application system for antithrombotic therapy |
| US6264978B1 (en) | 1991-12-20 | 2001-07-24 | Lts Lohmann Therapie-Systeme Gmbh & Co. Kg | Transdermal application system containing acetylsalicylic acid for antithrombotic therapy and cancer prophylaxis |
| ES2047456A1 (en) * | 1992-07-31 | 1994-02-16 | Postigo Herrando | Cosmetic compsn. - contains retinoic acid, beta-methasone di-propionate, urea and excipient |
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