CA1047928A - Effervescent enteric coated l-dopa formulation and method of using the same - Google Patents
Effervescent enteric coated l-dopa formulation and method of using the sameInfo
- Publication number
- CA1047928A CA1047928A CA239,591A CA239591A CA1047928A CA 1047928 A CA1047928 A CA 1047928A CA 239591 A CA239591 A CA 239591A CA 1047928 A CA1047928 A CA 1047928A
- Authority
- CA
- Canada
- Prior art keywords
- tablet
- dopa
- pharmaceutically acceptable
- phenylalanine
- 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
Links
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 title claims abstract description 97
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 239000000203 mixture Substances 0.000 title abstract description 13
- 238000009472 formulation Methods 0.000 title abstract description 7
- 238000000034 method Methods 0.000 title description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 13
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 13
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002662 enteric coated tablet Substances 0.000 claims abstract description 7
- 239000002702 enteric coating Substances 0.000 claims abstract description 7
- 238000009505 enteric coating Methods 0.000 claims abstract description 7
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 6
- 239000003701 inert diluent Substances 0.000 claims abstract description 3
- 239000003826 tablet Substances 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 14
- -1 1-methyl-2-acetylvinyl Chemical group 0.000 claims description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 229960005190 phenylalanine Drugs 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 5
- 229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 4
- 229940081734 cellulose acetate phthalate Drugs 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 4
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- WQNHWIYLCRZRLR-UHFFFAOYSA-N 2-(3-hydroxy-2,5-dioxooxolan-3-yl)acetic acid Chemical compound OC(=O)CC1(O)CC(=O)OC1=O WQNHWIYLCRZRLR-UHFFFAOYSA-N 0.000 claims description 2
- QGSHZMFEVDSXGR-KRWDZBQOSA-N benzyl (2s)-2-amino-3-(3,4-diacetyloxyphenyl)propanoate Chemical compound C1=C(OC(C)=O)C(OC(=O)C)=CC=C1C[C@H](N)C(=O)OCC1=CC=CC=C1 QGSHZMFEVDSXGR-KRWDZBQOSA-N 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 13
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- COWCOMKBMUTCGD-JTQLQIEISA-N (2s)-2-amino-3-(3,4-diacetyloxyphenyl)propanoic acid Chemical compound CC(=O)OC1=CC=C(C[C@H](N)C(O)=O)C=C1OC(C)=O COWCOMKBMUTCGD-JTQLQIEISA-N 0.000 claims 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 2
- 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 claims 2
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KZQJKVJONMBQQU-ZDUSSCGKSA-N benzyl (2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoate Chemical compound C([C@H](N)C(=O)OCC=1C=CC=CC=1)C1=CC=C(O)C(O)=C1 KZQJKVJONMBQQU-ZDUSSCGKSA-N 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 abstract description 5
- 241001465754 Metazoa Species 0.000 abstract description 2
- 208000027089 Parkinsonian disease Diseases 0.000 abstract 1
- 206010034010 Parkinsonism Diseases 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 238000001727 in vivo Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 18
- 238000010521 absorption reaction Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 210000000936 intestine Anatomy 0.000 description 6
- 206010047700 Vomiting Diseases 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000007922 dissolution test Methods 0.000 description 5
- 210000002784 stomach Anatomy 0.000 description 5
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- 229960003638 dopamine Drugs 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 210000000813 small intestine Anatomy 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- WMWANNCZUGLKAU-QRPNPIFTSA-N (2s)-2-amino-3-phenylpropanoic acid;potassium Chemical compound [K].OC(=O)[C@@H](N)CC1=CC=CC=C1 WMWANNCZUGLKAU-QRPNPIFTSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- VBWFMAYZSJVLMJ-UHFFFAOYSA-N 1h-indole-2,3,4-triol Chemical compound C1=CC(O)=C2C(O)=C(O)NC2=C1 VBWFMAYZSJVLMJ-UHFFFAOYSA-N 0.000 description 1
- 101710125089 Bindin Proteins 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000004031 Carboxy-Lyases Human genes 0.000 description 1
- 108090000489 Carboxy-Lyases Proteins 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- 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 1
- 206010028813 Nausea Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- UOJBFMJRKHJNNG-PPHPATTJSA-N [(1s)-1-carboxy-2-(3,4-diacetyloxyphenyl)ethyl]azanium;chloride Chemical compound Cl.CC(=O)OC1=CC=C(C[C@H](N)C(O)=O)C=C1OC(C)=O UOJBFMJRKHJNNG-PPHPATTJSA-N 0.000 description 1
- OSWNXJXGUNGKKM-GUTACTQSSA-N [(2s)-3-[3,4-bis(carboxymethyl)phenyl]-1-[[(2s)-3-[3,4-bis(carboxymethyl)phenyl]-1-methoxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]azanium;chloride Chemical compound [Cl-].C([C@@H](C(=O)OC)NC(=O)[C@@H]([NH3+])CC=1C=C(CC(O)=O)C(CC(O)=O)=CC=1)C1=CC=C(CC(O)=O)C(CC(O)=O)=C1 OSWNXJXGUNGKKM-GUTACTQSSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SJFUQIANPBDPDH-UHFFFAOYSA-N benzyl 2-amino-3-(3,4-dihydroxyphenyl)propanoate;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1COC(=O)C([NH3+])CC1=CC=C(O)C(O)=C1 SJFUQIANPBDPDH-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 230000003544 deproteinization Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- WFGNJLMSYIJWII-FJXQXJEOSA-N methyl (2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WFGNJLMSYIJWII-FJXQXJEOSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
-
- 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
- A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
- A61K9/0007—Effervescent
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49131304A JPS5157813A (en) | 1974-11-14 | 1974-11-14 | Ll dooba mataha sonojudotaiseizaino seiho |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1047928A true CA1047928A (en) | 1979-02-06 |
Family
ID=15054818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA239,591A Expired CA1047928A (en) | 1974-11-14 | 1975-11-13 | Effervescent enteric coated l-dopa formulation and method of using the same |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3961041A (enExample) |
| JP (1) | JPS5157813A (enExample) |
| CA (1) | CA1047928A (enExample) |
| DE (1) | DE2551280A1 (enExample) |
| ES (1) | ES442579A1 (enExample) |
| FR (1) | FR2290912A1 (enExample) |
| GB (1) | GB1485676A (enExample) |
| IT (1) | IT1069069B (enExample) |
| NL (1) | NL7513370A (enExample) |
| SE (1) | SE7512740L (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4147768A (en) * | 1976-09-13 | 1979-04-03 | Interx Research Corporation | Enteric coated digoxin and therapeutic use thereof |
| JPS54138128A (en) * | 1978-04-19 | 1979-10-26 | Akiyama Jiyouzai Kk | Double contrast medium for intestine |
| US4289751A (en) * | 1979-06-29 | 1981-09-15 | Merck & Co., Inc. | Effervescent enteric-coated formulation of soluble form of erythromycin and therapeutic use thereof |
| FR2470599A1 (fr) * | 1979-12-07 | 1981-06-12 | Panoz Donald | Perfectionnements apportes aux procedes de preparation de formes galeniques a action retard et a liberation programmee et formes galeniques de medicaments ainsi obtenus |
| GB2130087A (en) * | 1982-09-22 | 1984-05-31 | Dr Joachime Helbig | Pharmaceutical oral dosage forms of an active agent capable of forming or releasing bicarbonate ions |
| US4874614A (en) * | 1985-03-25 | 1989-10-17 | Abbott Laboratories | Pharmaceutical tableting method |
| US4863741A (en) * | 1985-03-25 | 1989-09-05 | Abbott Laboratories | Tablet composition for drug combinations |
| US4663349A (en) * | 1985-12-30 | 1987-05-05 | Merck & Co., Inc. | Rectally absorbable form of L-dopa |
| GB2189698A (en) | 1986-04-30 | 1987-11-04 | Haessle Ab | Coated omeprazole tablets |
| GB2189699A (en) * | 1986-04-30 | 1987-11-04 | Haessle Ab | Coated acid-labile medicaments |
| EP0252290B1 (en) * | 1986-06-10 | 1992-06-03 | CHIESI FARMACEUTICI S.p.A. | Pharmaceutical compositions containing levodopa methyl ester, preparation and therapeutic applications thereof |
| US4983400A (en) * | 1986-06-16 | 1991-01-08 | Merck & Co., Inc. | Controlled release combination of carbidopa/levodopa |
| GB8724763D0 (en) * | 1987-10-22 | 1987-11-25 | Aps Research Ltd | Sustained-release formulations |
| US4942039A (en) * | 1989-05-09 | 1990-07-17 | Miles Inc. | Effervescent analgesic antacid composition having reduced sodium content |
| GB9010039D0 (en) * | 1990-05-03 | 1990-06-27 | Reckitt & Colmann Prod Ltd | Medicament preparation |
| US5607969A (en) * | 1992-12-24 | 1997-03-04 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | L-DOPA ethyl ester to treat Parkinson's disease |
| US5354885A (en) * | 1992-12-24 | 1994-10-11 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Process for preparing ethyl ester of L-DOPA |
| SI9700186B (sl) | 1997-07-14 | 2006-10-31 | Lek, Tovarna Farmacevtskih In Kemicnih Izdelkov, D.D. | Nova farmacevtska oblika z nadzorovanim sproscanjem zdravilnih ucinkovin |
| US20040151768A1 (en) * | 1997-07-23 | 2004-08-05 | Chiesi Farmaceutici S.P.A. | Pharmaceutical compositions containing an effervescent acid-base couple |
| US7060734B1 (en) | 1997-09-09 | 2006-06-13 | Alza Corporation | Pharmaceutical coating composition and method of use |
| JP2001515855A (ja) * | 1997-09-09 | 2001-09-25 | アルザ・コーポレーション | 薬剤コーティング組成物と使用方法 |
| DE69910183T2 (de) * | 1998-03-11 | 2004-06-03 | Grelan Pharmaceutical Co., Ltd., Hamura | Darmlösliche sprudelnde zusammensetzungen |
| US20030091629A1 (en) * | 1998-03-27 | 2003-05-15 | Cima Labs Inc. | Sublingual buccal effervescent |
| US20030118645A1 (en) * | 1998-04-29 | 2003-06-26 | Pather S. Indiran | Pharmaceutical compositions for rectal and vaginal administration |
| US6974590B2 (en) | 1998-03-27 | 2005-12-13 | Cima Labs Inc. | Sublingual buccal effervescent |
| US6576250B1 (en) | 1998-03-27 | 2003-06-10 | Cima Labs Inc. | Pharmaceutical compositions for rectal and vaginal administration |
| US6350470B1 (en) * | 1998-04-29 | 2002-02-26 | Cima Labs Inc. | Effervescent drug delivery system for oral administration |
| DE69942205D1 (de) * | 1998-08-13 | 2010-05-12 | Cima Labs Inc | Microemulsionen als feste dosisformen zur oralen verabreichung |
| NZ512030A (en) | 1998-11-10 | 2003-10-31 | Teva Pharma | Process for manufacture of L-dopa ethyl ester |
| CA2350304A1 (en) | 1998-11-10 | 2000-05-18 | Teva Pharmaceutical Industries, Ltd. | Dispersible compositions containing l-dopa ethyl ester |
| KR100299562B1 (ko) | 1998-12-29 | 2001-11-22 | 우재영 | 안정성을극대화시킨5-피롤릴-2-피리딜메틸설피닐벤즈이미다졸유도체함유미세과립 |
| AU2005202472B2 (en) * | 1999-04-29 | 2008-12-18 | Cima Labs Inc. | Effervescent drug delivery system for oral administration |
| GB0217056D0 (en) * | 2002-07-23 | 2002-08-28 | Ass Octel | Use |
| CA2548915C (en) * | 2003-12-31 | 2012-10-16 | Cima Labs Inc. | Generally linear effervescent oral fentanyl dosage form and methods of administering |
| MXPA06007453A (es) * | 2003-12-31 | 2007-01-31 | Cima Labs Inc | Forma de dosificacion de opiaceo oral efervescente. |
| US7858121B2 (en) | 2003-12-31 | 2010-12-28 | Cima Labs, Inc. | Effervescent oral fentanyl dosage form and methods of administering fentanyl |
| JP2016029034A (ja) * | 2014-07-18 | 2016-03-03 | ナノメガ メディカル コーポレイションＮａｎｏｍｅｇａ Ｍｅｄｉｃａｌ Ｃｏｒｐｏｒａｔｉｏｎ | 医薬組成物 |
| JP2017203031A (ja) * | 2017-07-12 | 2017-11-16 | スティッチング グロニンゲン セントル フォー ドラッグ リサーチ | ｐＨ制御パルス送達システム、その調製法及び使用法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3131123A (en) * | 1959-03-13 | 1964-04-28 | Lab Francais De Therapeutique | Enteric tablets and manufacture thereof |
| FR2116256A1 (en) | 1970-12-02 | 1972-07-13 | Sobio Lab | Enteric - coated l-dopa - for treatment of parkinsonism with reduced gastrointestinal side-effects |
| US3891696A (en) * | 1973-11-02 | 1975-06-24 | Interx Research Corp | Novel, transient pro-drug forms of l-dopa |
-
1974
- 1974-11-14 JP JP49131304A patent/JPS5157813A/ja active Granted
-
1975
- 1975-04-10 US US05/566,745 patent/US3961041A/en not_active Expired - Lifetime
- 1975-11-10 GB GB46402/75A patent/GB1485676A/en not_active Expired
- 1975-11-13 ES ES442579A patent/ES442579A1/es not_active Expired
- 1975-11-13 CA CA239,591A patent/CA1047928A/en not_active Expired
- 1975-11-13 SE SE7512740A patent/SE7512740L/ not_active Application Discontinuation
- 1975-11-14 DE DE19752551280 patent/DE2551280A1/de not_active Withdrawn
- 1975-11-14 NL NL7513370A patent/NL7513370A/xx not_active Application Discontinuation
- 1975-11-14 FR FR7534769A patent/FR2290912A1/fr active Granted
- 1975-11-14 IT IT52218/75A patent/IT1069069B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IT1069069B (it) | 1985-03-25 |
| FR2290912B1 (enExample) | 1978-07-28 |
| JPS5436645B2 (enExample) | 1979-11-10 |
| JPS5157813A (en) | 1976-05-20 |
| DE2551280A1 (de) | 1976-05-20 |
| GB1485676A (en) | 1977-09-14 |
| SE7512740L (sv) | 1976-05-17 |
| US3961041A (en) | 1976-06-01 |
| FR2290912A1 (fr) | 1976-06-11 |
| NL7513370A (nl) | 1976-05-18 |
| ES442579A1 (es) | 1978-01-16 |
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