FI116450B - Menetelmä valmistaa metoprololin 24 tunnin valmistetta - Google Patents

Menetelmä valmistaa metoprololin 24 tunnin valmistetta Download PDF

Info

Publication number: FI116450B
Authority: FI; Finland
Prior art keywords: metoprolol; gum; sustained release; tablets; excipient
Prior art date: 1993-11-12

Application number

FI961996A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI961996L (fi

FI961996A0 (fi

Inventor

Anand R Baichwal

John N Staniforth

Original Assignee

Penwest Pharmaceuticals Co

Priority date (The priority date 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 date listed.)

1993-11-12

Filing date

1996-05-10

Publication date

2005-11-30

1996-05-10 Application filed by Penwest Pharmaceuticals Co filed Critical Penwest Pharmaceuticals Co

1996-05-10 Publication of FI961996A0 publication Critical patent/FI961996A0/fi

1996-05-29 Publication of FI961996L publication Critical patent/FI961996L/fi

2005-11-30 Application granted granted Critical

2005-11-30 Publication of FI116450B publication Critical patent/FI116450B/fi

Links

239000000203 mixture Substances 0.000 title claims abstract description 57
IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 title claims abstract description 54
229960002237 metoprolol Drugs 0.000 title claims abstract description 53
238000009472 formulation Methods 0.000 title abstract description 24
238000004519 manufacturing process Methods 0.000 title description 10
238000013268 sustained release Methods 0.000 claims abstract description 59
239000012730 sustained-release form Substances 0.000 claims abstract description 59
239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 47
230000002209 hydrophobic effect Effects 0.000 claims abstract description 17
239000003431 cross linking reagent Substances 0.000 claims abstract description 13
125000002091 cationic group Chemical group 0.000 claims abstract description 12
239000008024 pharmaceutical diluent Substances 0.000 claims abstract description 5
239000003814 drug Substances 0.000 claims description 37
229940079593 drug Drugs 0.000 claims description 34
238000000034 method Methods 0.000 claims description 26
238000002360 preparation method Methods 0.000 claims description 22
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 18
239000012530 fluid Substances 0.000 claims description 18
239000003795 chemical substances by application Substances 0.000 claims description 15
230000008569 process Effects 0.000 claims description 14
239000000230 xanthan gum Substances 0.000 claims description 14
229920001285 xanthan gum Polymers 0.000 claims description 14
235000010493 xanthan gum Nutrition 0.000 claims description 14
229940082509 xanthan gum Drugs 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 12
229920000869 Homopolysaccharide Polymers 0.000 claims description 10
239000001856 Ethyl cellulose Substances 0.000 claims description 9
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 claims description 9
235000019325 ethyl cellulose Nutrition 0.000 claims description 9
229920001249 ethyl cellulose Polymers 0.000 claims description 9
230000036571 hydration Effects 0.000 claims description 7
238000006703 hydration reaction Methods 0.000 claims description 7
230000007613 environmental effect Effects 0.000 claims description 6
238000004132 cross linking Methods 0.000 claims description 5
239000002552 dosage form Substances 0.000 claims description 5
229920000161 Locust bean gum Polymers 0.000 claims description 3
238000010348 incorporation Methods 0.000 claims description 3
235000010420 locust bean gum Nutrition 0.000 claims description 3
239000000711 locust bean gum Substances 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
229920013820 alkyl cellulose Polymers 0.000 claims description 2
229920001577 copolymer Polymers 0.000 claims description 2
230000000979 retarding effect Effects 0.000 claims description 2
229920001600 hydrophobic polymer Polymers 0.000 claims 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
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238000004090 dissolution Methods 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
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MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical group CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 4
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OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
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 3
239000011159 matrix material Substances 0.000 description 3
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GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
244000303965 Cyamopsis psoralioides Species 0.000 description 2
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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RGHAZVBIOOEVQX-UHFFFAOYSA-N Metoprolol succinate Chemical compound OC(=O)CCC(O)=O.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 RGHAZVBIOOEVQX-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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239000011230 binding agent Substances 0.000 description 2
229910001424 calcium ion Inorganic materials 0.000 description 2
239000001175 calcium sulphate Substances 0.000 description 2
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KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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229920006254 polymer film Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
235000010408 potassium alginate Nutrition 0.000 description 1
239000000737 potassium alginate Substances 0.000 description 1
MZYRDLHIWXQJCQ-YZOKENDUSA-L potassium alginate Chemical compound [K+].[K+].O1[C@@H](C([O-])=O)[C@@H](OC)[C@H](O)[C@H](O)[C@@H]1O[C@@H]1[C@@H](C([O-])=O)O[C@@H](O)[C@@H](O)[C@H]1O MZYRDLHIWXQJCQ-YZOKENDUSA-L 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
238000010079 rubber tapping Methods 0.000 description 1
238000004626 scanning electron microscopy Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
238000007921 solubility assay Methods 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
150000005846 sugar alcohols Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000011885 synergistic combination Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
WUBVEMGCQRSBBT-UHFFFAOYSA-N tert-butyl 4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(=O)(=O)C(F)(F)F)=CC1 WUBVEMGCQRSBBT-UHFFFAOYSA-N 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000001585 thymus vulgaris Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000000811 xylitol Substances 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
229960002675 xylitol Drugs 0.000 description 1
235000010447 xylitol 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
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
- 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
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
- 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
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Biophysics (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Cardiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

FI961996A 1993-11-12 1996-05-10 Menetelmä valmistaa metoprololin 24 tunnin valmistetta FI116450B (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US15127293		1993-11-12
US08/151,272 US5399358A (en)	1993-11-12	1993-11-12	Sustained release formulations for 24 hour release of metroprolol
PCT/US1994/012139 WO1995013055A1 (en)	1993-11-12	1994-10-19	Sustained release formulations for 24 hour release of metoprolol
US9412139		1994-10-19

Publications (3)

Publication Number	Publication Date
FI961996A0 FI961996A0 (fi)	1996-05-10
FI961996L FI961996L (fi)	1996-05-29
FI116450B true FI116450B (fi)	2005-11-30

Family

ID=22538025

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI961996A FI116450B (fi)	1993-11-12	1996-05-10	Menetelmä valmistaa metoprololin 24 tunnin valmistetta

Country Status (16)

Country	Link
US (1)	US5399358A (zh)
EP (1)	EP0730444B1 (zh)
JP (1)	JP2832248B2 (zh)
KR (1)	KR100197841B1 (zh)
CN (1)	CN1198596C (zh)
AT (1)	ATE230980T1 (zh)
AU (1)	AU675370B2 (zh)
CA (1)	CA2171844C (zh)
DE (1)	DE69432025T2 (zh)
DK (1)	DK0730444T3 (zh)
ES (1)	ES2191034T3 (zh)
FI (1)	FI116450B (zh)
HU (1)	HU223612B1 (zh)
IL (1)	IL111400A (zh)
TW (1)	TW314469B (zh)
WO (1)	WO1995013055A1 (zh)

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1993
- 1993-11-12 US US08/151,272 patent/US5399358A/en not_active Expired - Lifetime
1994
- 1994-10-19 EP EP94931991A patent/EP0730444B1/en not_active Expired - Lifetime
- 1994-10-19 JP JP7513847A patent/JP2832248B2/ja not_active Expired - Fee Related
- 1994-10-19 KR KR1019960702479A patent/KR100197841B1/ko not_active Expired - Fee Related
- 1994-10-19 HU HU9601008A patent/HU223612B1/hu not_active IP Right Cessation
- 1994-10-19 WO PCT/US1994/012139 patent/WO1995013055A1/en active IP Right Grant
- 1994-10-19 AT AT94931991T patent/ATE230980T1/de not_active IP Right Cessation
- 1994-10-19 DE DE69432025T patent/DE69432025T2/de not_active Expired - Lifetime
- 1994-10-19 CA CA002171844A patent/CA2171844C/en not_active Expired - Fee Related
- 1994-10-19 ES ES94931991T patent/ES2191034T3/es not_active Expired - Lifetime
- 1994-10-19 AU AU80875/94A patent/AU675370B2/en not_active Ceased
- 1994-10-19 DK DK94931991T patent/DK0730444T3/da active
- 1994-10-25 IL IL11140094A patent/IL111400A/en not_active IP Right Cessation
- 1994-11-12 CN CNB941200892A patent/CN1198596C/zh not_active Expired - Fee Related
- 1994-11-15 TW TW083110556A patent/TW314469B/zh active
1996
- 1996-05-10 FI FI961996A patent/FI116450B/fi active IP Right Grant

Also Published As

Publication number	Publication date
AU675370B2 (en)	1997-01-30
TW314469B (zh)	1997-09-01
KR100197841B1 (ko)	1999-06-15
EP0730444B1 (en)	2003-01-15
HU9601008D0 (en)	1996-06-28
DE69432025T2 (de)	2003-10-16
CN1109328A (zh)	1995-10-04
CA2171844A1 (en)	1995-05-18
JP2832248B2 (ja)	1998-12-09
IL111400A (en)	1999-03-12
HU223612B1 (hu)	2004-10-28
FI961996L (fi)	1996-05-29
ES2191034T3 (es)	2003-09-01
FI961996A0 (fi)	1996-05-10
WO1995013055A1 (en)	1995-05-18
CN1198596C (zh)	2005-04-27
DK0730444T3 (da)	2003-04-14
AU8087594A (en)	1995-05-29
CA2171844C (en)	2000-05-30
IL111400A0 (en)	1994-12-29
EP0730444A4 (en)	1996-11-06
EP0730444A1 (en)	1996-09-11
HUT75881A (en)	1997-05-28
US5399358A (en)	1995-03-21
JPH08511807A (ja)	1996-12-10
ATE230980T1 (de)	2003-02-15
DE69432025D1 (de)	2003-02-20

Publication	Publication Date	Title
FI116450B (fi)	2005-11-30	Menetelmä valmistaa metoprololin 24 tunnin valmistetta
US5399362A (en)	1995-03-21	Once-a-day metoprolol oral dosage form
KR100321489B1 (ko)	2002-10-09	고용량의불용성약물용서방성매트릭스
FI113337B (fi)	2004-04-15	Menetelmä pitkitetysti vapauttavan oksibutyniiniä sisältävän valmisteen valmistamiseksi
JP4077886B2 (ja)	2008-04-23	不溶性薬剤の持効性ヘテロ分散ヒドロゲル系
JPH08512061A (ja)	1996-12-17	持続放出性賦形剤
MXPA94008792A (en)	1999-04-06	Sustained release formulations for 24 hours of metopro release
MXPA96000024A (en)	1999-01-15	Form of oral dosing of metoprolol one time
MXPA95001193A (es)	1998-11-09	Formulaciones de oxibutinina de liberacioncontrolada

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