DE19814083C2 - Verfahren zur Herstellung von transdermalen therapeutischen Systemen unter Verwendung von basischen Alkalimetallsalzen zur Umwandlung von Wirkstoffsalzen in die freien Basen - Google Patents
Verfahren zur Herstellung von transdermalen therapeutischen Systemen unter Verwendung von basischen Alkalimetallsalzen zur Umwandlung von Wirkstoffsalzen in die freien BasenInfo
- Publication number
- DE19814083C2 DE19814083C2 DE19814083A DE19814083A DE19814083C2 DE 19814083 C2 DE19814083 C2 DE 19814083C2 DE 19814083 A DE19814083 A DE 19814083A DE 19814083 A DE19814083 A DE 19814083A DE 19814083 C2 DE19814083 C2 DE 19814083C2
- Authority
- DE
- Germany
- Prior art keywords
- active ingredient
- production
- transdermal
- transdermal systems
- salts
- 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 - Fee Related
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 18
- 239000013543 active substance Substances 0.000 title claims abstract description 9
- 239000002585 base Substances 0.000 title claims description 23
- 229910052783 alkali metal Inorganic materials 0.000 title claims description 7
- -1 alkali metal salts Chemical class 0.000 title claims description 6
- 230000001225 therapeutic effect Effects 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000004480 active ingredient Substances 0.000 claims description 41
- 239000011159 matrix material Substances 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000004760 silicates Chemical class 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 239000000853 adhesive Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 230000001070 adhesive effect Effects 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 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 claims description 5
- 239000012528 membrane Substances 0.000 claims description 5
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000004115 Sodium Silicate Substances 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910052911 sodium silicate Inorganic materials 0.000 claims description 3
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 claims description 2
- 229940100640 transdermal system Drugs 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- KFQYTPMOWPVWEJ-UHFFFAOYSA-N 6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol Chemical compound C1CC2=C(O)C=CC=C2CC1N(CCC)CCC1=CC=CS1 KFQYTPMOWPVWEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000004111 Potassium silicate Substances 0.000 claims 1
- 239000012790 adhesive layer Substances 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 230000003266 anti-allergic effect Effects 0.000 claims 1
- 230000001088 anti-asthma Effects 0.000 claims 1
- 229940035678 anti-parkinson drug Drugs 0.000 claims 1
- 239000000924 antiasthmatic agent Substances 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 229940030600 antihypertensive agent Drugs 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 claims 1
- 239000000939 antiparkinson agent Substances 0.000 claims 1
- 238000009792 diffusion process Methods 0.000 claims 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 claims 1
- 229910052913 potassium silicate Inorganic materials 0.000 claims 1
- 235000019353 potassium silicate Nutrition 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000012458 free base Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 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 3
- 239000011505 plaster Substances 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003292 glue Substances 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
- 230000002427 irreversible effect Effects 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- 235000019795 sodium metasilicate Nutrition 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 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
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
- 229920003148 Eudragit® E polymer Polymers 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 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
- 150000001412 amines Chemical class 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 230000004888 barrier function 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
- 150000005323 carbonate salts Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009434 installation Methods 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
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 239000012466 permeate Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229920000058 polyacrylate Polymers 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
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000009938 salting 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
- 210000004927 skin cell Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 210000002105 tongue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (12)
| 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 |
| JP2000540810A 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 |
| CA002326660A CA2326660C (en) | 1998-03-30 | 1999-03-20 | Method for producing transdermal therapeutic systems by using basic alkali metal salts for converting active agent salts into free bases |
| AU35974/99A AU758291B2 (en) | 1998-03-30 | 1999-03-20 | Method for producing transdermal therapeutic systems by using basic alkali metal salts for converting active agent salts into free bases |
| KR1020007010751A KR100550887B1 (ko) | 1998-03-30 | 1999-03-20 | 활성 물질염을 유리 염기로 변환하기 위하여 염기성 알칼리 금속염을 사용하는 경피 흡수 치료 시스템의 제조방법 |
| 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 |
| ES99917831T ES2201705T3 (es) | 1998-03-30 | 1999-03-20 | Procedimiento para la fabricacion de sistemas terapeuticos de administracion transdermica mediante la utilizacion de sales basicas de metales alcalinos para transformar las sales de principio activo en sus bases libres. |
| EP99917831A EP1067916B1 (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 |
| US09/647,688 US6620429B1 (en) | 1998-03-30 | 1999-03-20 | Use of basic alkali metal salts for manufacturing transdermal therapeutic system |
| DE59905750T DE59905750D1 (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 |
| AT99917831T ATE241343T1 (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 |
| NO20004926A NO329144B1 (no) | 1998-03-30 | 2000-09-29 | Fremgangsmate for fremstilling av transdermale terapeutiske systemer |
Applications Claiming Priority (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE19814083A1 DE19814083A1 (de) | 1999-10-14 |
| DE19814083C2 true DE19814083C2 (de) | 2002-02-07 |
Family
ID=7862903
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19814083A Expired - Fee Related 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 |
| DE59905750T Expired - Lifetime DE59905750D1 (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 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59905750T Expired - Lifetime DE59905750D1 (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 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6620429B1 (enExample) |
| EP (1) | EP1067916B1 (enExample) |
| JP (1) | JP4240813B2 (enExample) |
| KR (1) | KR100550887B1 (enExample) |
| AT (1) | ATE241343T1 (enExample) |
| AU (1) | AU758291B2 (enExample) |
| CA (1) | CA2326660C (enExample) |
| DE (2) | DE19814083C2 (enExample) |
| ES (1) | ES2201705T3 (enExample) |
| NO (1) | NO329144B1 (enExample) |
| WO (1) | WO1999049844A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8617591B2 (en) | 2002-07-30 | 2013-12-31 | Ucb Pharma Gmbh | Transdermal delivery system for the administration of rotigotine |
| US9186335B2 (en) | 2002-07-30 | 2015-11-17 | Ucb Pharma Gmbh | Hot melt TTS for administering rotigotine |
Families Citing this family (39)
| 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 |
| US6562369B2 (en) | 1999-12-16 | 2003-05-13 | Dermatrends, Inc. | Transdermal administration of androgenic drugs hydroxide-releasing agents as permeation enhancers |
| US6586000B2 (en) | 1999-12-16 | 2003-07-01 | Dermatrends, Inc. | Hydroxide-releasing agents as skin permeation enhancers |
| US6582724B2 (en) | 1999-12-16 | 2003-06-24 | Dermatrends, Inc. | Dual enhancer composition for topical and transdermal drug delivery |
| US6558695B2 (en) | 1999-12-16 | 2003-05-06 | Dermatrends, Inc. | Topical and transdermal administration of peptidyl drugs using hydroxide releasing agents as permeation enhancers |
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| 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 |
| US20220160697A1 (en) * | 2019-03-19 | 2022-05-26 | Nobelpharma Co., Ltd. | Pharmaceutical composition having excellent drug absorption into the living body and excellent chemical stability |
| DE102020207642A1 (de) * | 2020-06-19 | 2021-12-23 | Lts Lohmann Therapie-Systeme Ag | Verfahren zur herstellung von asenapin in form seiner freien base |
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| US4837027A (en) * | 1987-11-09 | 1989-06-06 | Alza Corporation | Transdermal drug delivery device |
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| 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 |
| 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 CA CA002326660A patent/CA2326660C/en not_active Expired - Lifetime
- 1999-03-20 AT AT99917831T patent/ATE241343T1/de not_active IP Right Cessation
- 1999-03-20 ES ES99917831T patent/ES2201705T3/es not_active Expired - Lifetime
- 1999-03-20 EP EP99917831A patent/EP1067916B1/de not_active Expired - Lifetime
- 1999-03-20 US US09/647,688 patent/US6620429B1/en not_active Expired - Lifetime
- 1999-03-20 KR KR1020007010751A patent/KR100550887B1/ko not_active Expired - Lifetime
- 1999-03-20 JP JP2000540810A patent/JP4240813B2/ja not_active Expired - Lifetime
- 1999-03-20 WO PCT/EP1999/001876 patent/WO1999049844A2/de not_active Ceased
- 1999-03-20 AU AU35974/99A patent/AU758291B2/en not_active Expired
- 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
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| 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 |
| DE3905051C2 (enExample) * | 1989-02-18 | 1991-08-08 | Lts Lohmann Therapie-Systeme Gmbh & Co. Kg, 5450 Neuwied, De | |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8617591B2 (en) | 2002-07-30 | 2013-12-31 | Ucb Pharma Gmbh | Transdermal delivery system for the administration of rotigotine |
| US9186335B2 (en) | 2002-07-30 | 2015-11-17 | Ucb Pharma Gmbh | Hot melt TTS for administering rotigotine |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010072561A (ko) | 2001-07-31 |
| AU758291B2 (en) | 2003-03-20 |
| NO20004926L (no) | 2000-11-22 |
| NO329144B1 (no) | 2010-08-30 |
| DE19814083A1 (de) | 1999-10-14 |
| ES2201705T3 (es) | 2004-03-16 |
| EP1067916A2 (de) | 2001-01-17 |
| KR100550887B1 (ko) | 2006-02-10 |
| CA2326660C (en) | 2005-11-29 |
| WO1999049844A3 (de) | 1999-11-25 |
| ATE241343T1 (de) | 2003-06-15 |
| CA2326660A1 (en) | 1999-10-07 |
| US6620429B1 (en) | 2003-09-16 |
| JP4240813B2 (ja) | 2009-03-18 |
| DE59905750D1 (de) | 2003-07-03 |
| JP2002509874A (ja) | 2002-04-02 |
| AU3597499A (en) | 1999-10-18 |
| WO1999049844A2 (de) | 1999-10-07 |
| EP1067916B1 (de) | 2003-05-28 |
| NO20004926D0 (no) | 2000-09-29 |
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| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8127 | New person/name/address of the applicant |
Owner name: LTS LOHMANN THERAPIE-SYSTEME AG, 56626 ANDERNACH, |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |