KR100905428B1 - 레보도파/카비도파/엔타카폰 약학적 제제 - Google Patents
레보도파/카비도파/엔타카폰 약학적 제제 Download PDFInfo
- Publication number
- KR100905428B1 KR100905428B1 KR1020017015737A KR20017015737A KR100905428B1 KR 100905428 B1 KR100905428 B1 KR 100905428B1 KR 1020017015737 A KR1020017015737 A KR 1020017015737A KR 20017015737 A KR20017015737 A KR 20017015737A KR 100905428 B1 KR100905428 B1 KR 100905428B1
- Authority
- KR
- South Korea
- Prior art keywords
- carbidopa
- entacapone
- levodopa
- pharmaceutically acceptable
- composition
- 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
- JRURYQJSLYLRLN-BJMVGYQFSA-N entacapone Chemical compound CCN(CC)C(=O)C(\C#N)=C\C1=CC(O)=C(O)C([N+]([O-])=O)=C1 JRURYQJSLYLRLN-BJMVGYQFSA-N 0.000 title claims abstract description 127
- 229960003337 entacapone Drugs 0.000 title claims abstract description 122
- IVTMXOXVAHXCHI-YXLMWLKOSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid;(2s)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1.NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 IVTMXOXVAHXCHI-YXLMWLKOSA-N 0.000 title abstract description 50
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 158
- QTAOMKOIBXZKND-PPHPATTJSA-N carbidopa Chemical compound O.NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 QTAOMKOIBXZKND-PPHPATTJSA-N 0.000 claims abstract description 70
- 229960004205 carbidopa Drugs 0.000 claims abstract description 67
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims abstract description 58
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims abstract description 58
- 229960004502 levodopa Drugs 0.000 claims abstract description 58
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 239000008247 solid mixture Substances 0.000 claims abstract description 31
- 150000004677 hydrates Chemical class 0.000 claims abstract description 20
- 239000008187 granular material Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 32
- 208000018737 Parkinson disease Diseases 0.000 claims description 11
- 238000005469 granulation Methods 0.000 claims description 9
- 230000003179 granulation Effects 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 239000007884 disintegrant Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 5
- 238000005550 wet granulation Methods 0.000 claims description 4
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 abstract description 10
- 235000019698 starch Nutrition 0.000 abstract description 10
- 239000008107 starch Substances 0.000 abstract description 10
- 150000005846 sugar alcohols Chemical group 0.000 abstract description 10
- 229920002261 Corn starch Polymers 0.000 abstract description 9
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 abstract description 9
- 229930195725 Mannitol Natural products 0.000 abstract description 9
- 239000008120 corn starch Substances 0.000 abstract description 9
- 239000000594 mannitol Substances 0.000 abstract description 9
- 235000010355 mannitol Nutrition 0.000 abstract description 9
- 239000004480 active ingredient Substances 0.000 description 20
- 238000010521 absorption reaction Methods 0.000 description 15
- 229940005928 entacapone 200 mg Drugs 0.000 description 13
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 11
- 229940001089 sinemet Drugs 0.000 description 11
- 229920002785 Croscarmellose sodium Polymers 0.000 description 9
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 9
- 229940016286 microcrystalline cellulose Drugs 0.000 description 9
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 9
- 239000008108 microcrystalline cellulose Substances 0.000 description 9
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 229940099112 cornstarch Drugs 0.000 description 8
- 229960001681 croscarmellose sodium Drugs 0.000 description 8
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 8
- 229960001855 mannitol Drugs 0.000 description 8
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 8
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 8
- 229940069328 povidone Drugs 0.000 description 8
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 229940032147 starch Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000007906 compression Methods 0.000 description 5
- 230000006835 compression Effects 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000007916 tablet composition Substances 0.000 description 5
- 229940085760 carbidopa 25 mg Drugs 0.000 description 4
- 229940087613 comtan Drugs 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 229940080381 levodopa 100 mg Drugs 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 3
- 229940124531 pharmaceutical excipient Drugs 0.000 description 3
- 229920003109 sodium starch glycolate Polymers 0.000 description 3
- 239000008109 sodium starch glycolate Substances 0.000 description 3
- 229940079832 sodium starch glycolate Drugs 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 102000006378 Catechol O-methyltransferase Human genes 0.000 description 2
- 108020002739 Catechol O-methyltransferase Proteins 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 229920003110 Primojel Polymers 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229940097987 carbidopa 10 mg Drugs 0.000 description 2
- 229940015929 carbidopa 12.5 mg Drugs 0.000 description 2
- 229940031220 carbidopa 37.5 mg Drugs 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 229940031222 levodopa 150 mg Drugs 0.000 description 2
- 229940080394 levodopa 250 mg Drugs 0.000 description 2
- 229940067290 levodopa 50 mg Drugs 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 229950008882 polysorbate Drugs 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000008279 sol Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 229960005168 croscarmellose Drugs 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- -1 for example Chemical compound 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009478 high shear granulation Methods 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000008184 oral solid dosage form Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000449 pharmaceutical disintegrant Substances 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Images
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
- A61K31/185—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
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- 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
- A61K31/275—Nitriles; Isonitriles
-
- 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
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI991485A FI109453B (fi) | 1999-06-30 | 1999-06-30 | Farmaseuttinen koostumus |
| FI991485 | 1999-06-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20020010155A KR20020010155A (ko) | 2002-02-02 |
| KR100905428B1 true KR100905428B1 (ko) | 2009-06-30 |
Family
ID=8554988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020017015737A Expired - Lifetime KR100905428B1 (ko) | 1999-06-30 | 2000-06-29 | 레보도파/카비도파/엔타카폰 약학적 제제 |
Country Status (42)
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI109453B (fi) * | 1999-06-30 | 2002-08-15 | Orion Yhtymae Oyj | Farmaseuttinen koostumus |
| US20030224045A1 (en) * | 2002-05-29 | 2003-12-04 | Chien-Hsuan Han | Combination immediate release sustained release levodopa/carbidopa dosage forms |
| US7094427B2 (en) * | 2002-05-29 | 2006-08-22 | Impax Laboratories, Inc. | Combination immediate release controlled release levodopa/carbidopa dosage forms |
| US20040166159A1 (en) * | 2002-05-29 | 2004-08-26 | Chien-Hsuan Han | Pharmaceutical dosage forms having immediate and controlled release properties that contain an aromatic amino acid decarboxylase inhibitor and levodopa |
| US20050147670A1 (en) * | 2002-05-29 | 2005-07-07 | Impax Laboratories Inc. | Oral disintegrating dosage forms |
| US20060013875A1 (en) * | 2002-05-29 | 2006-01-19 | Impax Laboratories, Inc. | Combination immediate release controlled release levodopa/carbidopa dosage forms |
| US20040006072A1 (en) * | 2002-06-25 | 2004-01-08 | Franz Robert M. | Sustained-release alprazolam composition |
| CA2501345A1 (en) * | 2002-10-11 | 2004-04-22 | Depomed Development, Ltd. | Gastro-retentive levodopa delivery form |
| AR044007A1 (es) | 2003-04-11 | 2005-08-24 | Newron Pharmaceuticals Inc | Metodos para el tratamiento de la enfermedad de parkinson |
| EP1588704A1 (en) | 2004-04-22 | 2005-10-26 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful in the treatment of restless legs syndrome and addictive disorders |
| SE0401842D0 (sv) * | 2004-07-12 | 2004-07-12 | Dizlin Medical Design Ab | Infusion and injection solution of levodopa |
| WO2006037061A2 (en) * | 2004-09-28 | 2006-04-06 | Farouk Karoum | Compositions and methods of using d-dopa to treat parkinson's disease |
| US20060173074A1 (en) | 2004-11-10 | 2006-08-03 | Juha Ellmen | Treatment of restless legs syndrome |
| AU2012216377C1 (en) * | 2005-06-08 | 2013-10-10 | Orion Corporation | Oral dosage form |
| EP2335696A1 (en) * | 2005-06-08 | 2011-06-22 | Orion Corporation | An entacapone-containing oral dosage form |
| EP1901720A2 (en) * | 2005-06-23 | 2008-03-26 | Spherics, Inc. | Improved dosage forms for movement disorder treatment |
| MY148644A (en) | 2005-07-18 | 2013-05-15 | Orion Corp | New pharmaceutical compounds |
| WO2007013830A1 (en) | 2005-07-26 | 2007-02-01 | Portela & Ca. S.A. | Nitrocatechol derivatives as comt inhibitors |
| US8877802B2 (en) * | 2005-07-28 | 2014-11-04 | Duke Univerity | Antiparkinsonian action of phenylisopropylamines |
| US20090012170A1 (en) * | 2005-09-21 | 2009-01-08 | Helena Nissinen | Treatment of symptoms of motor dysfunction |
| WO2007056570A2 (en) * | 2005-11-07 | 2007-05-18 | Teva Pharmaceutical Industries Ltd. | Levodopa compositions |
| US8772346B2 (en) * | 2005-11-09 | 2014-07-08 | Torrent Pharmaceuticals Limited | Pharmaceutical composition |
| GB2429645A (en) * | 2006-03-10 | 2007-03-07 | Sekhsaria Chemicals Ltd | Solid pharmaceutical composition comprising a COMT inhibitor, a starch and a wetting agent |
| CN100384411C (zh) * | 2006-03-17 | 2008-04-30 | 北京科信必成医药科技发展有限公司 | 卡左双多巴口腔崩解片 |
| WO2007113371A1 (en) * | 2006-03-31 | 2007-10-11 | Iprbox Oy | Pharmaceutical composition and preparation method thereof |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| EP1870097A1 (en) * | 2006-06-15 | 2007-12-26 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful in the treatment of cognitive disorders |
| US8106056B2 (en) * | 2006-06-16 | 2012-01-31 | Solvay Pharmaceuticals B.V. | Combination preparations comprising bifeprunox and a dopamine agonist |
| US20080131492A1 (en) * | 2006-06-23 | 2008-06-05 | Spherics, Inc. | Dosage forms for movement disorder treatment |
| EP2104424A4 (en) | 2006-10-30 | 2011-06-15 | Wockhardt Research Center | PHARMACEUTICAL COMPOSITIONS COMPRISING ENTACAPONE, LEVODOPA, AND CARBIDOPA |
| CA2673511A1 (en) * | 2006-12-22 | 2008-07-03 | Combinatorx, Incorporated | Pharmaceutical compositions for treatment of parkinson's disease and related disorders |
| WO2008081268A2 (en) * | 2006-12-27 | 2008-07-10 | Wockhardt Research Centre | Pharmaceutical compositions of entacapone |
| EP1946756A1 (en) * | 2007-01-17 | 2008-07-23 | Revotar Biopharmaceuticals AG | Use of entacapone in cosmetic, dermatological and pharmaceutical compositions |
| DK2481410T3 (en) | 2007-01-31 | 2016-10-24 | Bial - Portela & Ca S A | Nitrocatecholderivater as COMT inhibitors administered in a specific dosage regimen |
| US20110171275A1 (en) * | 2007-08-20 | 2011-07-14 | Team Academy Of Pharmaceutical Science | Gastroretentive drug delivery system, preparation method and use thereof |
| KR101444979B1 (ko) * | 2008-02-06 | 2014-10-07 | 욱크하르트 리미티드 | 생체 이용율이 개선된 엔타카폰, 레보도파 및 카르비도파의 약학 조성물 |
| ATE534382T1 (de) * | 2008-02-06 | 2011-12-15 | Wockhardt Ltd | Pharmazeutische zusammensetzungen von mit zuckeralkoholen zusammen mikronisiertem entacapon |
| BRPI0908731A2 (pt) | 2008-03-17 | 2017-05-16 | Bial - Portela & C A S A | formas cristalinas de 5-[3-(2,5-dicloro-4,6-dimetil-1-óxi-piridina-3-il)[1,2,4]oxadiazol-5-il]-3-nitrobenzeno-1,2-diol |
| US20110229566A1 (en) | 2008-08-22 | 2011-09-22 | Yatendra Kumar Gupta | Single Unit Oral Dose Pharmaceutical Composition Comprising Levodopa, Carbidopa And Entacapone Or Salts Thereof |
| CA2734972C (en) * | 2008-08-22 | 2017-03-28 | Wockhardt Research Centre | An extended release pharmaceutical composition of entacapone or salts thereof |
| TR200806646A2 (tr) * | 2008-09-03 | 2009-06-22 | Dr. F. Fri̇k İlaç San. Ve Ti̇c. A.Ş. | Entakapon, levodopa ve karbidoba içeren farmasötik kombinasyonlar |
| EP2233131A1 (en) | 2009-03-23 | 2010-09-29 | Laboratorios Lesvi, S.L. | Pharmaceutical composition containing levodopa, entacapone and carbidopa |
| CN102448444B (zh) | 2009-04-01 | 2016-05-25 | 巴尔-波特拉及康邦亚股份有限公司 | 包括硝基儿茶酚衍生物的药物制剂及其制备方法 |
| PT3192500T (pt) | 2009-05-19 | 2021-01-05 | Neuroderm Ltd | Composições para a administração contínua de inibidores da dopa decarboxilase |
| JP5718937B2 (ja) | 2009-12-25 | 2015-05-13 | イノファーマックス インコーポレイテッド | パーキンソン病を治療するための医薬組成物及びその調製方法 |
| JP5774610B2 (ja) | 2010-03-04 | 2015-09-09 | オリオン コーポレーション | パーキンソン病の治療方法 |
| DE102010023828A1 (de) * | 2010-06-15 | 2011-12-15 | IIP - Institut für industrielle Pharmazie, Forschungs- und Entwicklungsgesellschaft mbH | Pharmazeutisches Präparat, welches Entacapon, Levodopa und Carbidopa enthält |
| DK2640358T3 (en) * | 2010-11-15 | 2018-04-16 | Neuroderm Ltd | CONTINUOUS ADMINISTRATION OF L-DOPA, DOPA-DECARBOXYLASE INHIBITORS, CATECHOL-O-METHYL TRANSFERASE INHIBITORS AND COMPOSITIONS THEREOF |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| EP2508174A1 (en) | 2011-04-06 | 2012-10-10 | Ljiljana Sovic Brkicic | Pharmaceutical composition |
| WO2012147099A1 (en) * | 2011-04-25 | 2012-11-01 | Suven Nishtaa Pharma Pvt. Ltd. | Pharmaceutical compositions of levodopa, carbidopa and entacapone |
| BR112013027219A2 (pt) * | 2011-04-26 | 2016-12-27 | Innopharmax Inc | composição de entacapone, processo para preparar a composição de entacapone, composição farmacêutica, e, uso da composição de entacapone |
| US9126988B2 (en) | 2011-12-13 | 2015-09-08 | Bial—Portela & Ca, S.A. | Intermediate for preparing a catechol-O-methyltransferase inhibitor |
| TR201204839A2 (tr) | 2012-04-25 | 2012-12-21 | Ali̇ Rai̇f İlaç Sanayi̇ A.Ş. | Uzatılmış salım sağlayan levodopa karbıdopa entakapon içeren tablet formülasyonu. |
| EP2854764B1 (en) | 2012-06-05 | 2018-12-12 | Neuroderm Ltd | Compositions comprising apomorphine and organic acids and uses thereof |
| HUE056006T2 (hu) * | 2013-03-13 | 2022-01-28 | Neuroderm Ltd | Kombináció Parkinson-kór kezelésére |
| EP2799065A1 (en) * | 2013-04-30 | 2014-11-05 | Deva Holding Anonim Sirketi | Levodopa carbidopa entacapone pharmaceutical formulations |
| US10987313B2 (en) | 2013-10-07 | 2021-04-27 | Impax Laboratories, Llc | Muco-adhesive, controlled release formulations of levodopa and/or esters of levodopa and uses thereof |
| CN105658211A (zh) | 2013-10-07 | 2016-06-08 | 怡百克制药公司 | 左旋多巴和/或左旋多巴的酯的粘膜粘附性、控制释放调配物和其用途 |
| PL3777833T3 (pl) | 2014-03-13 | 2024-03-25 | Neuroderm Ltd. | Kompozycje inhibitorów dekarboksylazy dopa |
| US10258585B2 (en) | 2014-03-13 | 2019-04-16 | Neuroderm, Ltd. | DOPA decarboxylase inhibitor compositions |
| PT3782617T (pt) | 2014-09-04 | 2024-02-29 | Lobsor Pharmaceuticals Ab | Composições farmacêuticas de gel compreendendo levodopa, carbidopa e entacapona |
| WO2016083863A1 (en) | 2014-11-28 | 2016-06-02 | Bial - Portela & Ca, S.A. | Medicaments for slowing parkinson's disease |
| WO2016101969A1 (en) | 2014-12-23 | 2016-06-30 | Pharmathen S.A. | Levodopa/carbidopa/entacapone pharmaceutical preparation and method for preparing the same |
| WO2017039525A1 (en) | 2015-09-04 | 2017-03-09 | Lobsor Pharmaceuticals Aktiebolag | Method of treating a dopamine related disorder in a subject by administering levodopa, in combination with a dopamine decarboxylase inhibitor and a catechol-o-methyltransferase inhibitor |
| CN109689036B (zh) * | 2016-07-11 | 2026-06-19 | 康特拉医药股份有限公司 | 用于治疗早晨运动不能的脉冲药物输送系统 |
| ES2895054T3 (es) | 2016-08-18 | 2022-02-17 | Ilko Ilac Sanayi Ve Ticaret Anonim Sirketi | Fórmula de comprimido antiparkinson con perfil de disolución mejorado |
| WO2019145773A1 (en) | 2017-12-15 | 2019-08-01 | Nos Life Sciences Corporation | Liposomal-encapsulated formulations |
| AU2019237857B2 (en) | 2018-03-23 | 2024-11-21 | Lobsor Pharmaceuticals Aktiebolag | Continuous administration of pharmaceutical composition for treatment of neurodegenerative disorders |
| US11844754B2 (en) | 2020-11-17 | 2023-12-19 | Neuroderm, Ltd. | Methods for treatment of Parkinson's disease |
| US11213502B1 (en) | 2020-11-17 | 2022-01-04 | Neuroderm, Ltd. | Method for treatment of parkinson's disease |
| US11331293B1 (en) | 2020-11-17 | 2022-05-17 | Neuroderm, Ltd. | Method for treatment of Parkinson's disease |
| US12194150B2 (en) | 2020-12-22 | 2025-01-14 | Amneal Pharmaceuticals Llc | Levodopa dosing regimen |
| US11986449B2 (en) | 2020-12-22 | 2024-05-21 | Amneal Pharmaceuticals Llc | Levodopa dosing regimen |
| US12161612B2 (en) | 2023-04-14 | 2024-12-10 | Neuroderm, Ltd. | Methods and compositions for reducing symptoms of Parkinson's disease |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998031355A2 (en) * | 1997-01-16 | 1998-07-23 | Britannia Pharmaceuticals Limited | Pharmaceutical composition comprising n-propylnorapomorphine and cathecol-o-methyl-transferase inhibitor for treating parkinson's disease |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4190672A (en) | 1978-09-01 | 1980-02-26 | Stanley Fahn | Method and compositions of treating Parkinsonisms with levodopa and 3',4'-dihydroxy-2-methylisopropiophenone |
| GB8521350D0 (en) * | 1985-08-28 | 1985-10-02 | Euro Celtique Sa | Analgesic composition |
| US5236952A (en) | 1986-03-11 | 1993-08-17 | Hoffmann-La Roche Inc. | Catechol derivatives |
| NZ220599A (en) * | 1986-06-16 | 1990-10-26 | Merck & Co Inc | Controlled release oral dosage formulation of carbidopa and levodopa |
| US5283352A (en) | 1986-11-28 | 1994-02-01 | Orion-Yhtyma Oy | Pharmacologically active compounds, methods for the preparation thereof and compositions containing the same |
| DE4101873C2 (de) * | 1991-01-23 | 1993-12-09 | Isis Pharma Gmbh | Peroral applizierbare Arzneiform zur Behandlung zentraler Dopaminmangelzustände |
| US5888534A (en) | 1995-06-13 | 1999-03-30 | Pentech Pharmaceuticals, Inc. | Controlled release of drugs delivered by sublingual or buccal administration |
| US6599530B2 (en) | 1998-09-14 | 2003-07-29 | Orion Corporation | Oral compacted composition comprising catechol derivatives |
| FI109453B (fi) * | 1999-06-30 | 2002-08-15 | Orion Yhtymae Oyj | Farmaseuttinen koostumus |
-
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998031355A2 (en) * | 1997-01-16 | 1998-07-23 | Britannia Pharmaceuticals Limited | Pharmaceutical composition comprising n-propylnorapomorphine and cathecol-o-methyl-transferase inhibitor for treating parkinson's disease |
Non-Patent Citations (1)
| Title |
|---|
| Clin. Neuropharmacol.(제18권, 제46-57면, 1995년 * |
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