JP4240813B2 - 塩基性アルカリ金属塩を用いて活性物質塩を遊離塩基に変換する経皮治療システムの製造方法 - Google Patents
塩基性アルカリ金属塩を用いて活性物質塩を遊離塩基に変換する経皮治療システムの製造方法 Download PDFInfo
- Publication number
- JP4240813B2 JP4240813B2 JP2000540810A JP2000540810A JP4240813B2 JP 4240813 B2 JP4240813 B2 JP 4240813B2 JP 2000540810 A JP2000540810 A JP 2000540810A JP 2000540810 A JP2000540810 A JP 2000540810A JP 4240813 B2 JP4240813 B2 JP 4240813B2
- Authority
- JP
- Japan
- Prior art keywords
- active substance
- transdermal system
- producing
- salt
- transdermal
- 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.)
- Expired - Lifetime
Links
- 239000013543 active substance Substances 0.000 title claims abstract description 66
- 150000003839 salts Chemical class 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 32
- 229910052783 alkali metal Inorganic materials 0.000 title claims description 11
- -1 alkali metal salt Chemical class 0.000 title claims description 11
- 239000012458 free base Substances 0.000 title description 11
- 230000001225 therapeutic effect Effects 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000002585 base Substances 0.000 claims description 23
- 239000011159 matrix material Substances 0.000 claims description 23
- 229940100640 transdermal system Drugs 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000010408 film Substances 0.000 claims description 15
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical group [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000000853 adhesive Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 230000001070 adhesive effect Effects 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- 239000010409 thin film Substances 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000004115 Sodium Silicate Substances 0.000 claims description 4
- 239000000556 agonist Substances 0.000 claims description 4
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052911 sodium silicate Inorganic materials 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- KFQYTPMOWPVWEJ-UHFFFAOYSA-N 6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol Chemical group C1CC2=C(O)C=CC=C2CC1N(CCC)CCC1=CC=CS1 KFQYTPMOWPVWEJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000000202 analgesic effect Effects 0.000 claims description 2
- 239000000730 antalgic agent Substances 0.000 claims description 2
- 230000001088 anti-asthma Effects 0.000 claims description 2
- 230000001430 anti-depressive effect Effects 0.000 claims description 2
- 230000003474 anti-emetic effect Effects 0.000 claims description 2
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 2
- 230000000648 anti-parkinson Effects 0.000 claims description 2
- 239000000043 antiallergic agent Substances 0.000 claims description 2
- 239000000924 antiasthmatic agent Substances 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims description 2
- 239000002111 antiemetic agent Substances 0.000 claims description 2
- 239000002220 antihypertensive agent Substances 0.000 claims description 2
- 239000000939 antiparkinson agent Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 235000019353 potassium silicate Nutrition 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- 239000004111 Potassium silicate Substances 0.000 claims 1
- 229910052913 potassium silicate Inorganic materials 0.000 claims 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 150000004760 silicates Chemical class 0.000 description 8
- 235000012239 silicon dioxide Nutrition 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- 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 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 235000019795 sodium metasilicate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000011505 plaster Substances 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- CVDZPEDRUWPNGB-UHFFFAOYSA-N [K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] Chemical compound [K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CVDZPEDRUWPNGB-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002313 adhesive film Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- CEXBONHIOKGWNU-NTISSMGPSA-N hydron;(6s)-6-[propyl(2-thiophen-2-ylethyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol;chloride Chemical compound [Cl-].CCC[NH+]([C@@H]1CC2=CC=CC(O)=C2CC1)CCC1=CC=CS1 CEXBONHIOKGWNU-NTISSMGPSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920003149 Eudragit® E 100 Polymers 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229920013822 aminosilicone Polymers 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- NEDGUIRITORSKL-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;2-(dimethylamino)ethyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCCCOC(=O)C(C)=C.CN(C)CCOC(=O)C(C)=C NEDGUIRITORSKL-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000012241 calcium silicate Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- ZJQPLBFKBQYYIO-UHFFFAOYSA-N dodecasodium;trisilicate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] ZJQPLBFKBQYYIO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 230000037368 penetrate the skin Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960004499 scopolamine hydrobromide Drugs 0.000 description 1
- WTGQALLALWYDJH-MOUKNHLCSA-N scopolamine hydrobromide (anhydrous) Chemical compound Br.C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 WTGQALLALWYDJH-MOUKNHLCSA-N 0.000 description 1
- 239000013464 silicone adhesive Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 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
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- 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
- A61K9/7069—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
Landscapes
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19814083A DE19814083C2 (de) | 1998-03-30 | 1998-03-30 | Verfahren zur Herstellung von transdermalen therapeutischen Systemen unter Verwendung von basischen Alkalimetallsalzen zur Umwandlung von Wirkstoffsalzen in die freien Basen |
| DE19814083.5 | 1998-03-30 | ||
| PCT/EP1999/001876 WO1999049844A2 (de) | 1998-03-30 | 1999-03-20 | Verfahren zur herstellung von transdermalen therapeutischen systemen unter verwendung von basischen alkalimetallsalzen zur umwandlung von wirkstoffsalzen in die freien basen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002509874A JP2002509874A (ja) | 2002-04-02 |
| JP2002509874A5 JP2002509874A5 (https=) | 2005-12-22 |
| JP4240813B2 true JP4240813B2 (ja) | 2009-03-18 |
Family
ID=7862903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000540810A Expired - Lifetime JP4240813B2 (ja) | 1998-03-30 | 1999-03-20 | 塩基性アルカリ金属塩を用いて活性物質塩を遊離塩基に変換する経皮治療システムの製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6620429B1 (https=) |
| EP (1) | EP1067916B1 (https=) |
| JP (1) | JP4240813B2 (https=) |
| KR (1) | KR100550887B1 (https=) |
| AT (1) | ATE241343T1 (https=) |
| AU (1) | AU758291B2 (https=) |
| CA (1) | CA2326660C (https=) |
| DE (2) | DE19814083C2 (https=) |
| ES (1) | ES2201705T3 (https=) |
| NO (1) | NO329144B1 (https=) |
| WO (1) | WO1999049844A2 (https=) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19814084B4 (de) * | 1998-03-30 | 2005-12-22 | Lts Lohmann Therapie-Systeme Ag | D2-Agonist enthaltendes transdermales therapeutisches System zur Behandlung des Parkinson-Syndroms und Verfahren zu seiner Herstellung |
| US6673363B2 (en) | 1999-12-16 | 2004-01-06 | Dermatrends, Inc. | Transdermal and topical administration of local anesthetic agents using basic enhancers |
| US6562369B2 (en) | 1999-12-16 | 2003-05-13 | Dermatrends, Inc. | Transdermal administration of androgenic drugs hydroxide-releasing agents as permeation enhancers |
| US6582724B2 (en) | 1999-12-16 | 2003-06-24 | Dermatrends, Inc. | Dual enhancer composition for topical and transdermal drug delivery |
| US6645520B2 (en) | 1999-12-16 | 2003-11-11 | Dermatrends, Inc. | Transdermal administration of nonsteroidal anti-inflammatory drugs using hydroxide-releasing agents as permeation enhancers |
| US6586000B2 (en) | 1999-12-16 | 2003-07-01 | Dermatrends, Inc. | Hydroxide-releasing agents as skin permeation enhancers |
| US6562368B2 (en) | 1999-12-16 | 2003-05-13 | Dermatrends, Inc. | Transdermal administration of oxybutynin using hydroxide-releasing agents as permeation enhancers |
| US6562370B2 (en) | 1999-12-16 | 2003-05-13 | Dermatrends, Inc. | Transdermal administration of steroid drugs using hydroxide-releasing agents as permeation enhancers |
| US6565879B1 (en) | 1999-12-16 | 2003-05-20 | Dermatrends, Inc. | Topical and transdermal administration of peptidyl drugs with hydroxide-releasing agents as skin permeation enhancers |
| US6558695B2 (en) | 1999-12-16 | 2003-05-06 | Dermatrends, Inc. | Topical and transdermal administration of peptidyl drugs using hydroxide releasing agents as permeation enhancers |
| DE10041479A1 (de) * | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung zur Verabreichung von N-0923 |
| DE10041478A1 (de) | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
| DE10043321B4 (de) * | 2000-08-24 | 2005-07-28 | Neurobiotec Gmbh | Verwendung eines transdermalen therapeutischen Systems zur Behandlung der Parkinsonschen Krankheit, zur Behandlung und Prävention des prämenstruellen Syndroms und zur Lactationshemmung |
| DE10053397A1 (de) * | 2000-10-20 | 2002-05-02 | Schering Ag | Verwendung eines dopaminergen Wirkstoffes zur Behandlung von dopaminerg behandelbaren Erkrankungen |
| DE10064453A1 (de) * | 2000-12-16 | 2002-07-04 | Schering Ag | Verwendung eines dopaminergen Wirkstoffes zur Behandlung von dopaminerg behandelbaren Erkrankungen |
| DE10103860B4 (de) * | 2001-01-30 | 2004-12-23 | Lts Lohmann Therapie-Systeme Ag | Transdermales therapeutisches System für die Verabreichung carboxylgruppenhaltiger, nichtsteroidaler Antiphlogistika, sowie Verfahren zu seiner Herstellung |
| DE10234673B4 (de) | 2002-07-30 | 2007-08-16 | Schwarz Pharma Ag | Heißschmelz-TTS zur Verabreichung von Rotigotin und Verfahren zu seiner Herstellung sowie Verwendung von Rotigotin bei der Herstellung eines TTS im Heißschmelzverfahren |
| EP1386604A1 (en) * | 2002-07-30 | 2004-02-04 | Schwarz Pharma Ag | Improved transdermal delivery system |
| US8246980B2 (en) | 2002-07-30 | 2012-08-21 | Ucb Pharma Gmbh | Transdermal delivery system |
| EP1386605A1 (en) * | 2002-07-30 | 2004-02-04 | Schwarz Pharma Ag | Improved transdermal delivery system for the administration of rotigotine |
| US8246979B2 (en) | 2002-07-30 | 2012-08-21 | Ucb Pharma Gmbh | Transdermal delivery system for the administration of rotigotine |
| US8211462B2 (en) * | 2002-07-30 | 2012-07-03 | Ucb Pharma Gmbh | Hot-melt TTS for administering rotigotine |
| ATE295726T1 (de) * | 2002-12-02 | 2005-06-15 | Sanol Arznei Schwarz Gmbh | Verabreichung von rotigotine zur behandlung der parkinson'schen krankheit durch iontophorese |
| DE10261696A1 (de) | 2002-12-30 | 2004-07-15 | Schwarz Pharma Ag | Vorrichtung zur transdermalen Verabreichung von Rotigotin-Base |
| US20040214215A1 (en) * | 2003-03-07 | 2004-10-28 | Yu Ruey J. | Bioavailability and improved delivery of alkaline pharmaceutical drugs |
| US20050196418A1 (en) * | 2004-03-04 | 2005-09-08 | Yu Ruey J. | Bioavailability and improved delivery of alkaline pharmaceutical drugs |
| SI2215072T1 (sl) | 2007-11-28 | 2015-10-30 | Ucb Pharma Gmbh | Polimorfna oblika rotigotina |
| EP2258369B1 (en) * | 2008-02-27 | 2015-04-08 | Hisamitsu Pharmaceutical Co., Inc. | Medicated patch |
| JP5546013B2 (ja) * | 2008-02-27 | 2014-07-09 | 久光製薬株式会社 | 貼付剤及び包装体 |
| DE102008013701A1 (de) | 2008-03-11 | 2009-09-17 | Lts Lohmann Therapie-Systeme Ag | Transdermales Therapeutisches System mit stabilisierter Membran |
| US8815261B2 (en) | 2009-06-19 | 2014-08-26 | Medrx Co., Ltd. | Composition for external application comprising aripiprazole and organic acid as active ingredients |
| DE102010024105A1 (de) * | 2010-06-17 | 2011-12-22 | Grünenthal GmbH | Transdermale Verabreichung von Memantin |
| KR102013477B1 (ko) | 2012-07-26 | 2019-08-22 | 히사미쓰 세이야꾸 가부시키가이샤 | 첩부제 |
| US11123305B2 (en) | 2012-07-26 | 2021-09-21 | Hisamitsu Pharmaceutical Co., Inc. | Patch |
| WO2018115010A1 (en) | 2016-12-20 | 2018-06-28 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine and polysiloxane or polyisobutylene |
| ES2769286T3 (es) | 2016-12-20 | 2020-06-25 | Lts Lohmann Therapie Systeme Ag | Sistema terapéutico transdérmico que contiene asenapina |
| ES2881783T3 (es) | 2017-06-26 | 2021-11-30 | Lts Lohmann Therapie Systeme Ag | Sistema terapéutico transdérmico que contiene asenapina y polímero de acrílico y silicona |
| CA3101420A1 (en) | 2018-06-20 | 2019-12-26 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
| CN112533593A (zh) | 2018-06-20 | 2021-03-19 | 罗曼治疗系统股份公司 | 含有阿塞那平的透皮治疗系统 |
| CN113677343B (zh) * | 2019-03-19 | 2023-11-24 | 耐贝医药株式会社 | 生物体对药物的吸收性优异且化学稳定性也优异的医药组合物 |
| DE102020207642A1 (de) * | 2020-06-19 | 2021-12-23 | Lts Lohmann Therapie-Systeme Ag | Verfahren zur herstellung von asenapin in form seiner freien base |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3643987A1 (de) | 1986-12-22 | 1988-06-23 | Lohmann Therapie Syst Lts | Basische, wirkstoffdurchlaessige haftklebende polymermasse, insbesondere zum einsatz mit basischen wirkstoffen, verfahren zu ihrer herstellung und ihre verwendung |
| US4781924A (en) * | 1987-11-09 | 1988-11-01 | Alza Corporation | Transdermal drug delivery device |
| US4837027A (en) * | 1987-11-09 | 1989-06-06 | Alza Corporation | Transdermal drug delivery device |
| DE3905051A1 (de) * | 1989-02-18 | 1990-08-30 | Lohmann Therapie Syst Lts | Therapeutisches system zur verzoegerten und gesteuerten transdermalen oder transmucosalen verabreichung von wirkstoffen (i) |
| DE3905050A1 (de) * | 1989-02-18 | 1990-08-30 | Lohmann Therapie Syst Lts | Therapeutisches system zur verzoegerten und gesteuerten transdermalen oder transmucosalen verabreichung von wirkstoffen (ii) |
| EP0593807A1 (en) | 1992-10-22 | 1994-04-27 | LTS Lohmann Therapie-Systeme GmbH & Co. KG | Patch for transdermal administration of volatile pharmaceutically active ingredients of chemically basic nature and a process for preparation |
-
1998
- 1998-03-30 DE DE19814083A patent/DE19814083C2/de not_active Expired - Fee Related
-
1999
- 1999-03-20 WO PCT/EP1999/001876 patent/WO1999049844A2/de not_active Ceased
- 1999-03-20 US US09/647,688 patent/US6620429B1/en not_active Expired - Lifetime
- 1999-03-20 AU AU35974/99A patent/AU758291B2/en not_active Expired
- 1999-03-20 AT AT99917831T patent/ATE241343T1/de not_active IP Right Cessation
- 1999-03-20 CA CA002326660A patent/CA2326660C/en not_active Expired - Lifetime
- 1999-03-20 KR KR1020007010751A patent/KR100550887B1/ko not_active Expired - Lifetime
- 1999-03-20 ES ES99917831T patent/ES2201705T3/es not_active Expired - Lifetime
- 1999-03-20 JP JP2000540810A patent/JP4240813B2/ja not_active Expired - Lifetime
- 1999-03-20 EP EP99917831A patent/EP1067916B1/de not_active Expired - Lifetime
- 1999-03-20 DE DE59905750T patent/DE59905750D1/de not_active Expired - Lifetime
-
2000
- 2000-09-29 NO NO20004926A patent/NO329144B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002509874A (ja) | 2002-04-02 |
| NO20004926D0 (no) | 2000-09-29 |
| WO1999049844A3 (de) | 1999-11-25 |
| CA2326660C (en) | 2005-11-29 |
| KR100550887B1 (ko) | 2006-02-10 |
| ES2201705T3 (es) | 2004-03-16 |
| AU3597499A (en) | 1999-10-18 |
| DE19814083A1 (de) | 1999-10-14 |
| KR20010072561A (ko) | 2001-07-31 |
| ATE241343T1 (de) | 2003-06-15 |
| DE59905750D1 (de) | 2003-07-03 |
| AU758291B2 (en) | 2003-03-20 |
| NO20004926L (no) | 2000-11-22 |
| NO329144B1 (no) | 2010-08-30 |
| CA2326660A1 (en) | 1999-10-07 |
| DE19814083C2 (de) | 2002-02-07 |
| WO1999049844A2 (de) | 1999-10-07 |
| US6620429B1 (en) | 2003-09-16 |
| EP1067916A2 (de) | 2001-01-17 |
| EP1067916B1 (de) | 2003-05-28 |
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