KR100325494B1 - 트라마돌염을함유하는서방성약물제제 - Google Patents
트라마돌염을함유하는서방성약물제제 Download PDFInfo
- Publication number
- KR100325494B1 KR100325494B1 KR1019940021959A KR19940021959A KR100325494B1 KR 100325494 B1 KR100325494 B1 KR 100325494B1 KR 1019940021959 A KR1019940021959 A KR 1019940021959A KR 19940021959 A KR19940021959 A KR 19940021959A KR 100325494 B1 KR100325494 B1 KR 100325494B1
- Authority
- KR
- South Korea
- Prior art keywords
- weight
- drug formulation
- release
- tablet
- group
- 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
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical class COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 title claims abstract description 17
- 239000003814 drug Substances 0.000 title description 12
- 229940079593 drug Drugs 0.000 title description 11
- 238000002360 preparation method Methods 0.000 title description 5
- 238000013268 sustained release Methods 0.000 title description 2
- 239000012730 sustained-release form Substances 0.000 title description 2
- 239000013583 drug formulation Substances 0.000 claims abstract description 24
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 21
- 239000004480 active ingredient Substances 0.000 claims description 29
- 239000000945 filler Substances 0.000 claims description 14
- PPKXEPBICJTCRU-XMZRARIVSA-N (R,R)-tramadol hydrochloride Chemical compound Cl.COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 PPKXEPBICJTCRU-XMZRARIVSA-N 0.000 claims description 9
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 9
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 9
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 9
- 229960003107 tramadol hydrochloride Drugs 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- -1 methyl hydroxypropyl Chemical group 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 5
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 5
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- 239000007888 film coating Substances 0.000 claims 4
- 238000009501 film coating Methods 0.000 claims 4
- 239000007935 oral tablet Substances 0.000 abstract description 2
- 229940096978 oral tablet Drugs 0.000 abstract description 2
- 239000003826 tablet Substances 0.000 description 52
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 20
- 238000000034 method Methods 0.000 description 17
- 238000000338 in vitro Methods 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 235000019359 magnesium stearate Nutrition 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 8
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 8
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 8
- 235000019700 dicalcium phosphate Nutrition 0.000 description 8
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 8
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 8
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 8
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 8
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 8
- 239000008108 microcrystalline cellulose Substances 0.000 description 8
- 229940016286 microcrystalline cellulose Drugs 0.000 description 8
- 229940071676 hydroxypropylcellulose Drugs 0.000 description 6
- 208000002193 Pain Diseases 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 239000013563 matrix tablet Substances 0.000 description 4
- 239000007939 sustained release tablet Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 229920003086 cellulose ether Polymers 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 208000000094 Chronic Pain Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 239000012738 dissolution medium Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007941 film coated tablet Substances 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 210000003097 mucus Anatomy 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000007892 solid unit dosage form Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 229960004380 tramadol Drugs 0.000 description 2
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 2
- 229940038625 tramadol hydrochloride 100 mg Drugs 0.000 description 2
- 229940091845 tramadol hydrochloride 150 mg Drugs 0.000 description 2
- 229940038613 tramadol hydrochloride 200 mg Drugs 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 229920003157 Eudragit® RL 30 D Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/2853—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers, poly(lactide-co-glycolide)
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
- A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4329794.3 | 1993-09-03 | ||
| DE4329794A DE4329794C2 (de) | 1993-09-03 | 1993-09-03 | Tramadolsalz enthaltende Arzneimittel mit verzögerter Wirkstofffreisetzung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR950007841A KR950007841A (ko) | 1995-04-15 |
| KR100325494B1 true KR100325494B1 (ko) | 2002-06-22 |
Family
ID=6496771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019940021959A Expired - Lifetime KR100325494B1 (ko) | 1993-09-03 | 1994-09-01 | 트라마돌염을함유하는서방성약물제제 |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5601842A (enExample) |
| EP (1) | EP0642788B1 (enExample) |
| JP (1) | JP3954117B2 (enExample) |
| KR (1) | KR100325494B1 (enExample) |
| CN (1) | CN1092956C (enExample) |
| AT (1) | ATE166575T1 (enExample) |
| AU (1) | AU671384B2 (enExample) |
| BR (1) | BR9403030A (enExample) |
| CA (1) | CA2131350C (enExample) |
| CO (1) | CO4290295A1 (enExample) |
| CZ (1) | CZ288832B6 (enExample) |
| DE (2) | DE4329794C2 (enExample) |
| DK (1) | DK0642788T3 (enExample) |
| EC (1) | ECSP941148A (enExample) |
| ES (1) | ES2119034T3 (enExample) |
| FI (1) | FI113336B (enExample) |
| HK (1) | HK1010447A1 (enExample) |
| HU (1) | HU215955B (enExample) |
| IL (1) | IL109800A (enExample) |
| LT (1) | LT3664B (enExample) |
| MY (1) | MY111754A (enExample) |
| PE (1) | PE10195A1 (enExample) |
| PL (1) | PL177315B1 (enExample) |
| RU (1) | RU2138253C1 (enExample) |
| SI (1) | SI0642788T1 (enExample) |
| UA (1) | UA26455C2 (enExample) |
| UY (1) | UY23804A1 (enExample) |
| ZA (1) | ZA946775B (enExample) |
Families Citing this family (110)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5266331A (en) * | 1991-11-27 | 1993-11-30 | Euroceltique, S.A. | Controlled release oxycodone compositions |
| US5958459A (en) * | 1991-12-24 | 1999-09-28 | Purdue Pharma L.P. | Opioid formulations having extended controlled released |
| US5478577A (en) * | 1993-11-23 | 1995-12-26 | Euroceltique, S.A. | Method of treating pain by administering 24 hour oral opioid formulations exhibiting rapid rate of initial rise of plasma drug level |
| US5968551A (en) | 1991-12-24 | 1999-10-19 | Purdue Pharma L.P. | Orally administrable opioid formulations having extended duration of effect |
| US20080075781A1 (en) * | 1992-11-25 | 2008-03-27 | Purdue Pharma Lp | Controlled release oxycodone compositions |
| NZ260408A (en) | 1993-05-10 | 1996-05-28 | Euro Celtique Sa | Controlled release preparation comprising tramadol |
| US20070275062A1 (en) * | 1993-06-18 | 2007-11-29 | Benjamin Oshlack | Controlled release oxycodone compositions |
| IL110014A (en) * | 1993-07-01 | 1999-11-30 | Euro Celtique Sa | Solid controlled-release oral dosage forms of opioid analgesics |
| US7740881B1 (en) | 1993-07-01 | 2010-06-22 | Purdue Pharma Lp | Method of treating humans with opioid formulations having extended controlled release |
| US5879705A (en) * | 1993-07-27 | 1999-03-09 | Euro-Celtique S.A. | Sustained release compositions of morphine and a method of preparing pharmaceutical compositions |
| KR100354702B1 (ko) | 1993-11-23 | 2002-12-28 | 유로-셀티크 소시에떼 아노뉨 | 약학조성물의제조방법및서방형조성물 |
| US5891471A (en) | 1993-11-23 | 1999-04-06 | Euro-Celtique, S.A. | Pharmaceutical multiparticulates |
| US5843480A (en) | 1994-03-14 | 1998-12-01 | Euro-Celtique, S.A. | Controlled release diamorphine formulation |
| GB9422154D0 (en) | 1994-11-03 | 1994-12-21 | Euro Celtique Sa | Pharmaceutical compositions and method of producing the same |
| US5965161A (en) | 1994-11-04 | 1999-10-12 | Euro-Celtique, S.A. | Extruded multi-particulates |
| DE19530575A1 (de) * | 1995-08-19 | 1997-02-20 | Gruenenthal Gmbh | Schnell zerfallende Arzneiform von Tramadol oder einem Tramadolsalz |
| GB9519363D0 (en) | 1995-09-22 | 1995-11-22 | Euro Celtique Sa | Pharmaceutical formulation |
| WO1997032573A1 (en) * | 1996-03-08 | 1997-09-12 | Nycomed Danmark A/S | Modified release multiple-units dosage composition |
| DE19630035A1 (de) * | 1996-07-25 | 1998-01-29 | Asta Medica Ag | Tramadol Multiple Unit Formulierungen |
| DE19712398A1 (de) * | 1997-03-25 | 1998-10-01 | Gruenenthal Gmbh | Orale Anwendung von (+)-0-Demethyltramadol als Schmerzmittel |
| ATE322892T1 (de) * | 1997-07-02 | 2006-04-15 | Euro Celtique Sa | Stabilisierte tramadol formulierungen mit verzögerter freisetzung |
| US6156342A (en) * | 1998-05-26 | 2000-12-05 | Andex Pharmaceuticals, Inc. | Controlled release oral dosage form |
| DE29818454U1 (de) * | 1998-10-15 | 1999-01-14 | Euroceltique S.A., Luxemburg/Luxembourg | Opioid-Analgetikum |
| US6806294B2 (en) | 1998-10-15 | 2004-10-19 | Euro-Celtique S.A. | Opioid analgesic |
| AU3469100A (en) * | 1999-01-05 | 2000-07-24 | Copley Pharmaceutical Inc. | Sustained release formulation with reduced moisture sensitivity |
| DE19901686A1 (de) * | 1999-01-18 | 2000-07-20 | Gruenenthal Gmbh | Retardierte Tramadolzubereitungen mit einem lagerstabilen Freisetzungsprofil und Verfahren zu deren Herstellung |
| DE19901692C2 (de) * | 1999-01-18 | 2002-06-20 | Gruenenthal Gmbh | Verfahren zur Herstellung von Pellets mit einem Gehalt von bis zu 90 Gew.% eines pharmazeutischen Wirkstoffes |
| DE19918325A1 (de) | 1999-04-22 | 2000-10-26 | Euro Celtique Sa | Verfahren zur Herstellung von Arzneiformen mit regulierter Wirkstofffreisetzung mittels Extrusion |
| NZ517559A (en) * | 1999-08-31 | 2004-08-27 | Gruenenthal Chemie | Sustained release pharmaceutical composition containing tramadol saccharinate |
| US10179130B2 (en) | 1999-10-29 | 2019-01-15 | Purdue Pharma L.P. | Controlled release hydrocodone formulations |
| EP2295043A1 (en) | 1999-10-29 | 2011-03-16 | Euro-Celtique S.A. | Controlled release hydrocodone formulations |
| SK285128B6 (sk) * | 1999-12-28 | 2006-07-07 | Zentiva, A. S. | Liečivý prípravok s riadeným uvoľňovaním obsahujúci tramadol hydrochlorid a spôsob jeho prípravy |
| RU2165922C1 (ru) * | 2000-07-19 | 2001-04-27 | Государственный научно-исследовательский институт органической химии и технологии | Способ получения трамадола |
| ES2228789T3 (es) * | 2000-09-22 | 2005-04-16 | Smb Technology | Composicion oral de tramadol en forma de granulados para tomar una vez por dia. |
| DK1345595T3 (da) * | 2000-09-29 | 2007-09-10 | Solvay Pharm Bv | Ionstyrke-uafhængig farmaceutisk formulering med depotfrigivelse |
| EP2932964A1 (en) | 2000-10-30 | 2015-10-21 | Euro-Celtique S.A. | Controlled release hydrocodone formulations |
| RU2174836C1 (ru) * | 2000-12-15 | 2001-10-20 | Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин" | Фармацевтическая композиция, обладающая анальгезирующим действием |
| DE10108122A1 (de) | 2001-02-21 | 2002-10-02 | Gruenenthal Gmbh | Arzneimittel auf Basis von Tramadol |
| WO2002074241A2 (en) | 2001-03-16 | 2002-09-26 | Dmi Biosciences Inc. | Method of delaying ejaculation |
| UA81224C2 (uk) | 2001-05-02 | 2007-12-25 | Euro Celtic S A | Дозована форма оксикодону та її застосування |
| US20110104214A1 (en) | 2004-04-15 | 2011-05-05 | Purdue Pharma L.P. | Once-a-day oxycodone formulations |
| PE20030527A1 (es) * | 2001-10-24 | 2003-07-26 | Gruenenthal Chemie | Formulacion farmaceutica con liberacion retardada que contiene 3-(3-dimetilamino-1-etil-2-metil-propil) fenol o una sal farmaceuticamente aceptable del mismo y tabletas para administracion oral que la contienen |
| US8128957B1 (en) * | 2002-02-21 | 2012-03-06 | Valeant International (Barbados) Srl | Modified release compositions of at least one form of tramadol |
| US20060099249A1 (en) * | 2002-02-21 | 2006-05-11 | Pawan Seth | Modified release formulations of at least one form of tramadol |
| ES2399880T3 (es) * | 2002-03-15 | 2013-04-04 | Cypress Bioscience, Inc. | Milnaciprán para el tratamiento del síndrome del intestino irritable |
| IL164077A0 (en) * | 2002-03-22 | 2005-12-18 | Cilag Ag | Sustained release formulation of tramadol |
| US7410965B2 (en) | 2002-05-29 | 2008-08-12 | Gruenenthal Gmbh | Delayed release pharmaceutical composition containing 1-dimethyl-amino-3-(3-methoxyphenyl)-2-methyl-pentan-3-ol |
| DE10224108A1 (de) * | 2002-05-29 | 2004-01-29 | Grünenthal GmbH | 1-Dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol enthaltendes Arzneimiitel mit verzögerter Wirkstofffreisetzung |
| US7776314B2 (en) | 2002-06-17 | 2010-08-17 | Grunenthal Gmbh | Abuse-proofed dosage system |
| CA2498798A1 (en) * | 2002-09-20 | 2004-04-01 | Alpharma, Inc. | Sustained-release opioid formulations and methods of use |
| TWI319713B (en) | 2002-10-25 | 2010-01-21 | Sustained-release tramadol formulations with 24-hour efficacy | |
| US20060003004A1 (en) * | 2002-10-25 | 2006-01-05 | Collegium Pharmaceutical, Inc. | Pulsatile release compositions of milnacipran |
| US20040132826A1 (en) * | 2002-10-25 | 2004-07-08 | Collegium Pharmaceutical, Inc. | Modified release compositions of milnacipran |
| US8487002B2 (en) | 2002-10-25 | 2013-07-16 | Paladin Labs Inc. | Controlled-release compositions |
| WO2004067039A1 (en) * | 2003-01-28 | 2004-08-12 | Collegium Pharmaceutical, Inc. | Multiparticulate compositions of milnacipran for oral administration |
| DE10333835A1 (de) * | 2003-07-24 | 2005-03-10 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexane-1,3-diol enthaltendes Arzneimittel mit verzögerter Wirkstofffreisetzung |
| US8075872B2 (en) | 2003-08-06 | 2011-12-13 | Gruenenthal Gmbh | Abuse-proofed dosage form |
| DE102004020220A1 (de) * | 2004-04-22 | 2005-11-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
| DE102005005446A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
| DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
| DE102004032051A1 (de) * | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
| US20070048228A1 (en) * | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
| DE10361596A1 (de) * | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| PT1842533E (pt) * | 2003-08-06 | 2013-05-17 | Gruenenthal Gmbh | Forma de dosagem protegida contra abuso |
| US20060172006A1 (en) * | 2003-10-10 | 2006-08-03 | Vincent Lenaerts | Sustained-release tramadol formulations with 24-hour clinical efficacy |
| US20050089558A1 (en) * | 2003-10-28 | 2005-04-28 | Alamo Pharmaceuticals, Llc | Compositions and methods for the co-formulation and administration of tramadol and propoxyphene |
| DE102004032103A1 (de) * | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102004032049A1 (de) * | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
| DE102005005449A1 (de) * | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
| ITMI20050391A1 (it) * | 2005-03-11 | 2006-09-12 | Ph & T S P A | Formulazioni a rilascio controllato di alfuzosin |
| AU2006269225B2 (en) * | 2005-07-07 | 2011-10-06 | Farnam Companies, Inc. | Sustained release pharmaceutical compositions for highly water soluble drugs |
| CN101242856A (zh) | 2005-09-09 | 2008-08-13 | 莱博法姆公司 | 持续药物释放的组合物 |
| DK1931346T3 (da) | 2005-09-09 | 2012-10-22 | Angelini Labopharm Llc | Trazodonsammensætning til indgivelse en gang om dagen |
| US20090104266A1 (en) * | 2005-09-15 | 2009-04-23 | Tobias Jung | 3-(2-dimethylaminomethylcy clohexyl)phenol retard formulation |
| US8691272B2 (en) * | 2005-12-30 | 2014-04-08 | Intelgenx Corp. | Multilayer tablet |
| US20070190141A1 (en) * | 2006-02-16 | 2007-08-16 | Aaron Dely | Extended release opiate composition |
| EP2049087A2 (en) * | 2006-07-21 | 2009-04-22 | LAB International SRL | Hydrophilic abuse deterrent delivery system |
| DE102006044694A1 (de) * | 2006-09-22 | 2008-03-27 | Krewel Meuselbach Gmbh | Perorale feste Schmerzmittelzubereitung |
| PL2120570T3 (pl) * | 2007-02-12 | 2012-10-31 | Vyrix Pharmaceuticals Inc | Leczenie współwystępującego przedwczesnego wytrysku i zaburzenia wzwodu prącia |
| DK2114147T3 (da) | 2007-02-12 | 2012-06-25 | Dmi Biosciences Inc | Reduktion af bivirkninger af tramadol |
| DE102007011485A1 (de) * | 2007-03-07 | 2008-09-11 | Grünenthal GmbH | Darreichungsform mit erschwertem Missbrauch |
| RU2469718C2 (ru) * | 2007-10-16 | 2012-12-20 | Лабофарм Инк. | Двухслойная композиция для непрерывного высвобождения ацетаминофена и трамадола |
| JP5651818B2 (ja) | 2007-12-17 | 2015-01-14 | パラディン ラブス インコーポレーテッド | 誤用を防止するための放出制御製剤 |
| AU2009207796B2 (en) | 2008-01-25 | 2014-03-27 | Grunenthal Gmbh | Pharmaceutical dosage form |
| KR101690094B1 (ko) * | 2008-05-09 | 2016-12-27 | 그뤼넨탈 게엠베하 | 분무 응결 단계의 사용하에 중간 분말 제형 및 최종 고체 제형을 제조하는 방법 |
| US20100003322A1 (en) * | 2008-07-03 | 2010-01-07 | Lai Felix S | Enteric coated hydrophobic matrix formulation |
| US8486449B2 (en) * | 2008-12-16 | 2013-07-16 | Paladin Labs Inc. | Misuse preventative, controlled release formulation |
| ES2428938T3 (es) | 2009-07-22 | 2013-11-12 | Grünenthal GmbH | Forma de dosificación resistente a la manipulación y estabilizada frente a la oxidación |
| CA2765971C (en) | 2009-07-22 | 2017-08-22 | Gruenenthal Gmbh | Hot-melt extruded controlled release dosage form |
| US10610528B2 (en) | 2009-12-08 | 2020-04-07 | Intelgenx Corp. | Solid oral film dosage forms and methods for making same |
| US20110136815A1 (en) * | 2009-12-08 | 2011-06-09 | Horst Zerbe | Solid oral film dosage forms and methods for making same |
| WO2011095314A2 (en) * | 2010-02-03 | 2011-08-11 | Grünenthal GmbH | Preparation of a powdery pharmaceutical composition by means of an extruder |
| EP2568968B1 (en) | 2010-05-10 | 2017-07-12 | Euro-Celtique S.A. | Manufacturing of active-free granules and tablets comprising the same |
| BR112013000190A2 (pt) | 2010-07-06 | 2017-11-07 | Gruenenthal Gmbh | formas de dosagem de retenção gástrica compreendendo um análogo de gaba e um opioide |
| RU2604676C2 (ru) | 2010-09-02 | 2016-12-10 | Грюненталь Гмбх | Устойчивая к разрушению лекарственная форма, содержащая неорганическую соль |
| PL2611425T3 (pl) | 2010-09-02 | 2014-09-30 | Gruenenthal Gmbh | Odporna na ingerencję postać dawki zawierająca polimer anionowy |
| EP2635258A1 (en) * | 2010-11-04 | 2013-09-11 | AbbVie Inc. | Drug formulations |
| PL2736495T3 (pl) | 2011-07-29 | 2018-01-31 | Gruenenthal Gmbh | Tabletka odporna na ingerencję, zapewniająca natychmiastowe uwalnianie leku |
| HRP20171458T1 (hr) | 2011-07-29 | 2017-11-17 | Grünenthal GmbH | Tableta otporna na mijenjanje koja pruža neposredno oslobađanje lijeka |
| WO2013127831A1 (en) | 2012-02-28 | 2013-09-06 | Grünenthal GmbH | Tamper-resistant dosage form comprising pharmacologically active compound and anionic polymer |
| LT2838512T (lt) | 2012-04-18 | 2018-11-12 | GrĆ¼nenthal GmbH | Pažeidimui atspari ir dozės atpalaidavimo nuokrypiui atspari farmacinė vaisto forma |
| US10064945B2 (en) | 2012-05-11 | 2018-09-04 | Gruenenthal Gmbh | Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc |
| AR096438A1 (es) | 2013-05-29 | 2015-12-30 | Gruenenthal Gmbh | Forma de dosificación resistente al uso indebido con perfil de liberación bimodal, proceso |
| JP6445537B2 (ja) | 2013-05-29 | 2018-12-26 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | １個または複数の粒子を含有する改変防止（ｔａｍｐｅｒ−ｒｅｓｉｓｔａｎｔ）剤形 |
| US10624862B2 (en) | 2013-07-12 | 2020-04-21 | Grünenthal GmbH | Tamper-resistant dosage form containing ethylene-vinyl acetate polymer |
| JP6480936B2 (ja) | 2013-11-26 | 2019-03-13 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | クライオミリングによる粉末状医薬組成物の調製 |
| JP2017518980A (ja) | 2014-05-12 | 2017-07-13 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | タペンタドールを含む、改変防止即時放出カプセル製剤 |
| CN106456550A (zh) | 2014-05-26 | 2017-02-22 | 格吕伦塔尔有限公司 | 避免乙醇剂量倾泻的多颗粒 |
| KR20170139158A (ko) | 2015-04-24 | 2017-12-18 | 그뤼넨탈 게엠베하 | 즉시 방출되고 용매 추출 방지된 변조 방지된 투여 형태 |
| WO2017042325A1 (en) | 2015-09-10 | 2017-03-16 | Grünenthal GmbH | Protecting oral overdose with abuse deterrent immediate release formulations |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3065143A (en) | 1960-04-19 | 1962-11-20 | Richardson Merrell Inc | Sustained release tablet |
| JPS5492631A (en) * | 1977-12-27 | 1979-07-23 | Kowa Co | Analgestic |
| US4259314A (en) * | 1979-12-10 | 1981-03-31 | Hans Lowey | Method and composition for the preparation of controlled long-acting pharmaceuticals |
| US4389393A (en) * | 1982-03-26 | 1983-06-21 | Forest Laboratories, Inc. | Sustained release therapeutic compositions based on high molecular weight hydroxypropylmethylcellulose |
| EP0147780A3 (en) * | 1984-01-03 | 1987-03-11 | Merck & Co. Inc. | Drug delivery device |
| US4968508A (en) * | 1987-02-27 | 1990-11-06 | Eli Lilly And Company | Sustained release matrix |
| FR2618073B1 (fr) * | 1987-07-16 | 1990-09-07 | Pf Medicament | Comprimes de type a matrice hydrophile a base de salbutamol et leur procede de preparation |
| DE3830353A1 (de) * | 1988-09-07 | 1990-03-15 | Basf Ag | Verfahren zur kontinuierlichen herstellung von festen pharmazeutischen formen |
| US5126145A (en) * | 1989-04-13 | 1992-06-30 | Upsher Smith Laboratories Inc | Controlled release tablet containing water soluble medicament |
| US5268181A (en) * | 1989-04-13 | 1993-12-07 | Upsher-Smith Laboratories, Inc. | Method of using niacin to control nocturnal cholesterol synthesis |
| JPH04217925A (ja) * | 1990-03-27 | 1992-08-07 | Nippon Saafuakutanto Kogyo Kk | 新規な解熱消炎鎮痛剤組成物 |
| NZ260408A (en) * | 1993-05-10 | 1996-05-28 | Euro Celtique Sa | Controlled release preparation comprising tramadol |
| DE4315525B4 (de) * | 1993-05-10 | 2010-04-15 | Euro-Celtique S.A. | Pharmazeutische Zusammensetzung |
-
1993
- 1993-09-03 DE DE4329794A patent/DE4329794C2/de not_active Expired - Fee Related
-
1994
- 1994-05-26 IL IL10980094A patent/IL109800A/xx not_active IP Right Cessation
- 1994-07-11 UY UY23804A patent/UY23804A1/es not_active IP Right Cessation
- 1994-07-19 PE PE1994246995A patent/PE10195A1/es not_active IP Right Cessation
- 1994-07-22 MY MYPI94001903A patent/MY111754A/en unknown
- 1994-08-24 ES ES94113192T patent/ES2119034T3/es not_active Expired - Lifetime
- 1994-08-24 EP EP94113192A patent/EP0642788B1/de not_active Expired - Lifetime
- 1994-08-24 SI SI9430142T patent/SI0642788T1/xx unknown
- 1994-08-24 DK DK94113192T patent/DK0642788T3/da active
- 1994-08-24 DE DE59406075T patent/DE59406075D1/de not_active Expired - Lifetime
- 1994-08-24 AT AT94113192T patent/ATE166575T1/de active
- 1994-08-25 EC EC1994001148A patent/ECSP941148A/es unknown
- 1994-08-29 HU HU9402478A patent/HU215955B/hu unknown
- 1994-09-01 JP JP20895794A patent/JP3954117B2/ja not_active Expired - Lifetime
- 1994-09-01 KR KR1019940021959A patent/KR100325494B1/ko not_active Expired - Lifetime
- 1994-09-01 PL PL94304860A patent/PL177315B1/pl unknown
- 1994-09-01 CA CA002131350A patent/CA2131350C/en not_active Expired - Lifetime
- 1994-09-01 RU RU94032150A patent/RU2138253C1/ru active
- 1994-09-01 BR BR9403030A patent/BR9403030A/pt not_active Application Discontinuation
- 1994-09-02 CO CO94039369A patent/CO4290295A1/es unknown
- 1994-09-02 ZA ZA946775A patent/ZA946775B/xx unknown
- 1994-09-02 FI FI944035A patent/FI113336B/fi not_active IP Right Cessation
- 1994-09-02 CN CN94115648A patent/CN1092956C/zh not_active Expired - Lifetime
- 1994-09-02 LT LTIP2033A patent/LT3664B/lt not_active IP Right Cessation
- 1994-09-02 UA UA94095777A patent/UA26455C2/uk unknown
- 1994-09-02 AU AU72803/94A patent/AU671384B2/en not_active Expired
- 1994-09-05 CZ CZ19942140A patent/CZ288832B6/cs not_active IP Right Cessation
-
1996
- 1996-01-16 US US08/585,741 patent/US5601842A/en not_active Expired - Lifetime
-
1998
- 1998-09-28 HK HK98111000A patent/HK1010447A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100325494B1 (ko) | 트라마돌염을함유하는서방성약물제제 | |
| HK1010447B (en) | Tramadol salt containing medicaments with sustained release of the active ingredient | |
| AU2003260336C1 (en) | Sustained release formulations comprising lamotrigine | |
| AU2002322964B2 (en) | Dosage forms having prolonged active ingredient release | |
| JP2005506367A (ja) | 有効物質を徐放する３−（３−ジメチルアミノ−１−エチル−２−メチル−プロピル）フェノール含有医薬 | |
| HUP0103883A2 (hu) | Új, késleltetett felszabadulású, orális készítmények | |
| HUP0203334A2 (hu) | Közvetlen kompresszióval előállított polimer tabletta magok | |
| AU2002322964A1 (en) | Dosage forms having prolonged active ingredient release | |
| CA2533330A1 (en) | Pharmaceutical preparation containing 6-dimethylaminomethyl-1-(3-methoxyphenyl)-cyclohexane-1,3-diol with delayed active ingredient release | |
| JP2005526739A (ja) | コレステロール濃度を低下させる活性成分を含み、活性成分が遅延放出される薬剤 | |
| US20040127541A1 (en) | Bicifadine formulation | |
| JP5420126B2 (ja) | ｐＨ非依存延長放出性医薬組成物 | |
| TWI883162B (zh) | 一種非布司他片 | |
| EP1512394B1 (en) | Universal controlled-release composition comprising chitosan | |
| WO2009027786A2 (en) | Matrix dosage forms of varenicline | |
| PL200822B1 (pl) | Kompozycja farmaceutyczna zawierająca rywastygminę | |
| US20030190351A1 (en) | Extended release venlafaxine formulations | |
| AU2006291422B2 (en) | 3-(2-dimethylaminomethyl cyclohexyl) phenol retard formulation | |
| CN1172429A (zh) | 使用从高等植物中可得到的粉末状水解胶体树胶的持续释放药物运送体系 | |
| WO2008038106A1 (en) | Venlafaxine extended release formulations | |
| EP1815850A1 (en) | Controlled release formulation of divalproic acid and its derivatives | |
| LI | Universelle Zusammensetzung zur kontrollierten Wirkstoffabgabe enthaltend Chitosan Composition universelle à libération controlée comprenant du chitosane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19940901 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19990818 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19940901 Comment text: Patent Application |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20011127 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20020207 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20020208 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| PR1001 | Payment of annual fee |
Payment date: 20050121 Start annual number: 4 End annual number: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20060126 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20070125 Start annual number: 6 End annual number: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20080122 Start annual number: 7 End annual number: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20090123 Start annual number: 8 End annual number: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 20100204 Start annual number: 9 End annual number: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20101228 Start annual number: 10 End annual number: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 20120202 Start annual number: 11 End annual number: 11 |
|
| FPAY | Annual fee payment |
Payment date: 20130117 Year of fee payment: 12 |
|
| PR1001 | Payment of annual fee |
Payment date: 20130117 Start annual number: 12 End annual number: 12 |
|
| FPAY | Annual fee payment |
Payment date: 20140120 Year of fee payment: 13 |
|
| PR1001 | Payment of annual fee |
Payment date: 20140120 Start annual number: 13 End annual number: 13 |
|
| EXPY | Expiration of term | ||
| PC1801 | Expiration of term |
Termination date: 20150301 Termination category: Expiration of duration |