WO1999045924A1 - Composition - Google Patents
Composition Download PDFInfo
- Publication number
- WO1999045924A1 WO1999045924A1 PCT/EP1999/001557 EP9901557W WO9945924A1 WO 1999045924 A1 WO1999045924 A1 WO 1999045924A1 EP 9901557 W EP9901557 W EP 9901557W WO 9945924 A1 WO9945924 A1 WO 9945924A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dosage form
- aqueous dispersion
- plasticizer
- form according
- tablet
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 44
- 239000002552 dosage form Substances 0.000 claims abstract description 26
- 238000013270 controlled release Methods 0.000 claims abstract description 14
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 11
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 238000011321 prophylaxis Methods 0.000 claims abstract description 7
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 claims abstract description 6
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 claims abstract description 6
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 claims abstract description 6
- 206010012289 Dementia Diseases 0.000 claims abstract description 6
- 241000124008 Mammalia Species 0.000 claims abstract description 6
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 claims abstract description 6
- 230000007450 amyloidogenic pathway Effects 0.000 claims abstract description 6
- 230000002708 enhancing effect Effects 0.000 claims abstract description 6
- 230000020978 protein processing Effects 0.000 claims abstract description 6
- 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 54
- 239000006185 dispersion Substances 0.000 claims description 52
- 239000004014 plasticizer Substances 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000001856 Ethyl cellulose Substances 0.000 claims description 31
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 31
- 229920001249 ethyl cellulose Polymers 0.000 claims description 31
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 30
- 239000011248 coating agent Substances 0.000 claims description 30
- 238000000576 coating method Methods 0.000 claims description 30
- 239000008213 purified water Substances 0.000 claims description 28
- 229920000642 polymer Polymers 0.000 claims description 24
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 22
- 230000004584 weight gain Effects 0.000 claims description 22
- 235000019786 weight gain Nutrition 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 20
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 18
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 18
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 18
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 18
- 239000005642 Oleic acid Substances 0.000 claims description 18
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000000908 ammonium hydroxide Substances 0.000 claims description 18
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 18
- 235000019359 magnesium stearate Nutrition 0.000 claims description 18
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 18
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 15
- 239000002202 Polyethylene glycol Substances 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 15
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 15
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 15
- HWPKGOGLCKPRLZ-UHFFFAOYSA-M monosodium citrate Chemical compound [Na+].OC(=O)CC(O)(C([O-])=O)CC(O)=O HWPKGOGLCKPRLZ-UHFFFAOYSA-M 0.000 claims description 15
- 235000018342 monosodium citrate Nutrition 0.000 claims description 15
- 239000002524 monosodium citrate Substances 0.000 claims description 15
- 239000002245 particle Substances 0.000 claims description 15
- 229920001223 polyethylene glycol Polymers 0.000 claims description 15
- 239000002775 capsule Substances 0.000 claims description 14
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 14
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 14
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 14
- 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 description 14
- 229940079593 drug Drugs 0.000 claims description 12
- 239000006186 oral dosage form Substances 0.000 claims description 12
- 239000004615 ingredient Substances 0.000 claims description 11
- XAAHAAMILDNBPS-UHFFFAOYSA-L calcium hydrogenphosphate dihydrate Chemical compound O.O.[Ca+2].OP([O-])([O-])=O XAAHAAMILDNBPS-UHFFFAOYSA-L 0.000 claims description 10
- 150000005690 diesters Chemical class 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 9
- 230000002209 hydrophobic effect Effects 0.000 claims description 9
- 239000011159 matrix material Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 150000003626 triacylglycerols Chemical class 0.000 claims description 8
- 229920003063 hydroxymethyl cellulose Polymers 0.000 claims description 7
- 229940031574 hydroxymethyl cellulose Drugs 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 235000019864 coconut oil Nutrition 0.000 claims description 5
- 239000003240 coconut oil Substances 0.000 claims description 5
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims description 5
- 239000007903 gelatin capsule Substances 0.000 claims description 5
- 239000000017 hydrogel Substances 0.000 claims description 5
- 229920003084 Avicel® PH-102 Polymers 0.000 claims description 4
- 229920003102 Methocel™ E4M Polymers 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 235000010980 cellulose Nutrition 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920000609 methyl cellulose Polymers 0.000 claims description 3
- 239000001923 methylcellulose Substances 0.000 claims description 3
- 238000007906 compression Methods 0.000 claims description 2
- 230000006835 compression Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 241000756042 Polygonatum Species 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 11
- 230000006870 function Effects 0.000 description 8
- 239000001993 wax Substances 0.000 description 8
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 7
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 235000021314 Palmitic acid Nutrition 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- 235000021360 Myristic acid Nutrition 0.000 description 4
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 3
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229960002446 octanoic acid Drugs 0.000 description 3
- 239000000473 propyl gallate Substances 0.000 description 3
- 229940075579 propyl gallate Drugs 0.000 description 3
- 235000010388 propyl gallate Nutrition 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000007908 dry granulation Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000009478 high shear granulation Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 101150018711 AASS gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical group CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- BXYUSUYKLCALQI-UHFFFAOYSA-N azanium (Z)-octadec-9-enoate hydrate Chemical compound [OH-].[NH4+].C(CCCCCCCC=C/CCCCCCCC)(=O)O BXYUSUYKLCALQI-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 230000004793 poor memory Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 150000005691 triesters Chemical class 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- 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
- A61K9/2009—Inorganic compounds
-
- 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
- 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
- A61K9/2886—Dragees; Coated pills or tablets, e.g. with film or compression coating having two or more different drug-free coatings; Tablets of the type inert core-drug layer-inactive layer
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61K9/28—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
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IL13819299A IL138192A0 (en) | 1998-03-11 | 1999-03-05 | Controlled release oral dosage forms |
BR9908374-4A BR9908374A (en) | 1998-03-11 | 1999-03-05 | Composition |
CA002323177A CA2323177A1 (en) | 1998-03-11 | 1999-03-05 | Composition |
JP2000535339A JP2002506031A (en) | 1998-03-11 | 1999-03-05 | Composition |
EP99911765A EP1061918A1 (en) | 1998-03-11 | 1999-03-05 | Controlled release composition of (1-azabicyclo(2.2.2)oct-3-yl)acetonitrile monohydrochloride |
KR1020007010054A KR20010034588A (en) | 1998-03-11 | 1999-03-05 | Composition |
NZ505807A NZ505807A (en) | 1998-03-11 | 1999-03-05 | Controlled release oral dosage form containing [R-(Z)]-alpha-(methoxyimino)-alpha-(1-azabicyclo [2.2.2]oct-3-yl)acetonitrile monohydrochloride; useful for the treatment or prophylaxis of dementia |
AU30332/99A AU748396C (en) | 1998-03-11 | 1999-03-05 | Composition |
US09/623,213 US6451343B1 (en) | 1998-03-11 | 1999-03-05 | Composition for treating dementia and Alzheimer's disease |
HU0101043A HUP0101043A3 (en) | 1998-03-11 | 1999-03-05 | Controlled release oral dosage form containing [r-(z)]-alpha-(methoxyimino)-alpha-(1-azabicyclo[2.2.2]oct-3-yl]acetonitrile monohydrochlorid and process for its preparation |
NO20004491A NO20004491L (en) | 1998-03-11 | 2000-09-08 | Mixture |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7752798P | 1998-03-11 | 1998-03-11 | |
US7748098P | 1998-03-11 | 1998-03-11 | |
GBGB9805192.3A GB9805192D0 (en) | 1998-03-11 | 1998-03-11 | Composition |
GB9805192.3 | 1998-03-11 | ||
US60/077,480 | 1998-03-11 | ||
US60/077,527 | 1998-03-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999045924A1 true WO1999045924A1 (en) | 1999-09-16 |
Family
ID=27269240
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1999/001557 WO1999045924A1 (en) | 1998-03-11 | 1999-03-05 | Composition |
Country Status (16)
Country | Link |
---|---|
US (1) | US6451343B1 (en) |
EP (1) | EP1061918A1 (en) |
JP (1) | JP2002506031A (en) |
KR (1) | KR20010034588A (en) |
CN (1) | CN1292696A (en) |
AR (1) | AR018147A1 (en) |
AU (1) | AU748396C (en) |
CA (1) | CA2323177A1 (en) |
CO (1) | CO5080740A1 (en) |
HU (1) | HUP0101043A3 (en) |
IL (1) | IL138192A0 (en) |
NO (1) | NO20004491L (en) |
NZ (1) | NZ505807A (en) |
PL (1) | PL342600A1 (en) |
TR (1) | TR200002626T2 (en) |
WO (1) | WO1999045924A1 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2813651A1 (en) | 2000-09-05 | 2002-03-08 | Valeo | HYDROKINETIC COUPLING APPARATUS, PARTICULARLY FOR MOTOR VEHICLE |
WO2003053402A1 (en) * | 2001-12-20 | 2003-07-03 | Pharmacia Corporation | Zero-order sustained released dosage forms and method of making the same |
WO2004011002A1 (en) * | 2002-07-25 | 2004-02-05 | Pharmacia Corporation | Sustained-release tablet composition comprising a dopamine receptor agonist |
WO2004010997A1 (en) * | 2002-07-25 | 2004-02-05 | Pharmacia Corporation | Sustained-release tablet composition of pramipexole |
WO2004010998A1 (en) * | 2002-07-25 | 2004-02-05 | Pharmacia Corporation | Sustained-release tablet comprising reboxetine |
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WO2004010998A1 (en) * | 2002-07-25 | 2004-02-05 | Pharmacia Corporation | Sustained-release tablet comprising reboxetine |
WO2004010999A1 (en) * | 2002-07-25 | 2004-02-05 | Pharmacia Corporation | Pramipexole once-daily dosage form |
WO2004011002A1 (en) * | 2002-07-25 | 2004-02-05 | Pharmacia Corporation | Sustained-release tablet composition comprising a dopamine receptor agonist |
AU2003261241B2 (en) * | 2002-07-25 | 2009-06-18 | Boehringer Ingelheim International Gmbh | Sustained-release tablet composition of pramipexole |
EP2289514A1 (en) * | 2002-07-25 | 2011-03-02 | Pharmacia Corporation | Pramipexole once daily dosage form |
EA017595B1 (en) * | 2002-07-25 | 2013-01-30 | Фармация Корпорейшн | Pramipexole once-daily dosage form |
US8399016B2 (en) | 2002-07-25 | 2013-03-19 | Boehringer Ingelheim International Gmbh | Sustained-release tablet composition of pramipexole |
HRP20041235B1 (en) * | 2002-07-25 | 2013-07-31 | Boehringer Ingelheim International Gmbh | Sustained-release tablet composition of pramipexole |
HRP20041234B1 (en) * | 2002-07-25 | 2013-07-31 | Pharmacia Corporation | Pramipexole once-daily dosage form |
US8679533B2 (en) | 2002-07-25 | 2014-03-25 | Pharmacia Corporation | Pramipexole once-daily dosage form |
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Also Published As
Publication number | Publication date |
---|---|
NO20004491D0 (en) | 2000-09-08 |
AU748396B2 (en) | 2002-06-06 |
IL138192A0 (en) | 2001-11-25 |
AU3033299A (en) | 1999-09-27 |
TR200002626T2 (en) | 2001-03-21 |
HUP0101043A3 (en) | 2002-02-28 |
NO20004491L (en) | 2000-09-08 |
AU748396C (en) | 2003-01-23 |
HUP0101043A2 (en) | 2001-12-28 |
CA2323177A1 (en) | 1999-09-16 |
JP2002506031A (en) | 2002-02-26 |
AR018147A1 (en) | 2001-10-31 |
PL342600A1 (en) | 2001-06-18 |
KR20010034588A (en) | 2001-04-25 |
US6451343B1 (en) | 2002-09-17 |
CN1292696A (en) | 2001-04-25 |
CO5080740A1 (en) | 2001-09-25 |
EP1061918A1 (en) | 2000-12-27 |
NZ505807A (en) | 2003-01-31 |
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