WO1997016173A1 - Nouvelle technique de granulation humide - Google Patents
Nouvelle technique de granulation humide Download PDFInfo
- Publication number
- WO1997016173A1 WO1997016173A1 PCT/CA1996/000724 CA9600724W WO9716173A1 WO 1997016173 A1 WO1997016173 A1 WO 1997016173A1 CA 9600724 W CA9600724 W CA 9600724W WO 9716173 A1 WO9716173 A1 WO 9716173A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- active ingredient
- solubility
- electrolyte
- compound
- wet granulation
- Prior art date
Links
- 238000005550 wet granulation Methods 0.000 title claims abstract description 8
- 238000005516 engineering process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 238000005054 agglomeration Methods 0.000 claims abstract description 7
- 230000002776 aggregation Effects 0.000 claims abstract description 7
- 239000004480 active ingredient Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 26
- 239000003792 electrolyte Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229960001951 montelukast sodium Drugs 0.000 claims description 8
- LBFBRXGCXUHRJY-HKHDRNBDSA-M montelukast sodium Chemical group [Na+].CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC([O-])=O)CC1 LBFBRXGCXUHRJY-HKHDRNBDSA-M 0.000 claims description 8
- 239000003826 tablet Substances 0.000 claims description 8
- 238000005469 granulation Methods 0.000 claims description 5
- 230000003179 granulation Effects 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 239000007891 compressed tablet Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 4
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 4
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 3
- 239000008108 microcrystalline cellulose Substances 0.000 description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.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 WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 2
- 229920002785 Croscarmellose sodium Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229960005168 croscarmellose Drugs 0.000 description 2
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- KVVDRQDTODKIJD-UHFFFAOYSA-N 2-cyclopropylacetic acid Chemical compound OC(=O)CC1CC1 KVVDRQDTODKIJD-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 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 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000011010 calcium phosphates Nutrition 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
- 229960000913 crospovidone Drugs 0.000 description 1
- -1 dextrates Substances 0.000 description 1
- 229940096516 dextrates Drugs 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 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 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 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
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
- A61K9/2009—Inorganic compounds
-
- 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
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1682—Processes
- A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
Definitions
- This invention is concerned with a novel method of wet granulation in the manufacture of tablets comprising a large dose of a highly soluble compound as active ingredient.
- the novel method comprises the addition of a second compound having the capability of decreasing solubility of the active ingredient prior to agglomeration.
- the invention is particularly concerned with the novel method wherein the active ingredient is a highly soluble ionic compound.
- the novel method of this invention is a wet granulation of an active ingredient which is a highly soluble compound and is to be inco ⁇ orated in a relatively high concentration in compressed tablets which comprises the addition of a second compound to reduce the solubility of the active ingredient prior to the agglomeration step.
- the solubility of the active ingredient is decreased and a signficant increase in the viscosity of the granulation is adequately suppressed.
- This novel method is particularly useful wherein the active ingredient is ionic and has an aqueous solubility of about 10 to about 500 mg/ml, especially about 135 to about 235 mg/ml of water.
- the second compound added during the novel process is ordinarily a soluble ionic compound that can suppress the solubility of the active ingredient especially an electrolyte having an ion in common with that of the active ingredient.
- the tablet compositions prepared by the novel method of this invention are generally art recognized and employ standard excipients based on their compatibility with one another and with the active ingredient .
- excipients are such as: microcrystalline cellulose, dextrates, calcium phosphates, or pregelatinized starch for their compactibility properties, lactose, mannitol, sorbitol, xylitol, sucrose or glucose because of their water solubility which improves the agglomeration process; hydroxypropyl cellulose, hydroxypropyl methylcellulose, polyvinly pyrrolidone as binders or adhesives; Croscarmelose, crospovidone or sodium starch glycolate as disintegrants; and lastly, magnesium or calcium stearate, stearic acid, sodium stearyl fumarate, or polyethylene glycols as lubricants; and a granulating fluid such as water or ethanol: water mixtures.
- the active agent is dry blended with the excipients, and an aqueous solution of the second compound is atomized onto the blend.
- the blend is then granulated by spraying onto it an aqueous solution of the granulating fluid, which may or may not contain the binder. After drying, the granulation is sized, lubricated with magnesium stearate and then compressed to form the tablet cores.
- the active ingredient in the following Example is identified as montelukast sodium. This name is listed in USAN and is used by T.R. Jones, et al in Can. J. Physiol. Pharmacol.. (1995) 73(2), 191-201. It has the name and absolute structural formula as follows:
- Sodium chloride was dissolved in 540 g of water. Hydroxypropyl cellulose was dissolved in 1485 g of water. The microcrystalline cellulose, montelukast sodium, lactose hydrous and Croscarmellose were added together and blended for 5 minutes. The sodium chloride solution was added over 30 seconds and blended for 30 seconds. The hydroxypropylcellulose solution was sprayed onto the mixture over 1.5 minutes and mixed for 30 seconds. After drying, the granulation was sized and then lubricated by addition of the magnesium stearate. The lubricated blend was then compressed to form tablet cores.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Medicinal Preparation (AREA)
Abstract
On facilite la granulation humide d'un composé extrêmement soluble en lui ajoutant un modulateur de solubilité avant l'étape d'agglomération.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9516946A JPH11514382A (ja) | 1995-11-02 | 1996-10-31 | 新規な湿粒法 |
| AU72741/96A AU709301B2 (en) | 1995-11-02 | 1996-10-31 | New technology for wet granulation |
| EP96934274A EP0859600A1 (fr) | 1995-11-02 | 1996-10-31 | Nouvelle technique de granulation humide |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US616195P | 1995-11-02 | 1995-11-02 | |
| US60/006,161 | 1995-11-02 | ||
| GBGB9604277.5A GB9604277D0 (en) | 1996-02-29 | 1996-02-29 | New technology for wet granulation |
| GB9604277.5 | 1996-02-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997016173A1 true WO1997016173A1 (fr) | 1997-05-09 |
Family
ID=26308826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CA1996/000724 WO1997016173A1 (fr) | 1995-11-02 | 1996-10-31 | Nouvelle technique de granulation humide |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0859600A1 (fr) |
| JP (1) | JPH11514382A (fr) |
| AU (1) | AU709301B2 (fr) |
| CA (1) | CA2236175A1 (fr) |
| WO (1) | WO1997016173A1 (fr) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003035036A1 (fr) * | 2001-10-26 | 2003-05-01 | Merck Frosst Canada & Co. | Formulation de granules de montelukast |
| WO2007077135A1 (fr) | 2005-12-30 | 2007-07-12 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Préparation pharmaceutique contenant du montélukast |
| CZ298224B6 (cs) * | 2003-04-29 | 2007-07-25 | Pliva Istrazivanje I Razvoj D.O.O. | Farmaceutická kompozice obsahující jako úcinnou látku ribavirin a zpusob její výroby |
| WO2014012954A1 (fr) | 2012-07-18 | 2014-01-23 | Takeda Gmbh | Traitement de l'asthme sévère partiellement régulé ou non régulé |
| WO2015110394A1 (fr) | 2014-01-22 | 2015-07-30 | Takeda Gmbh | Traitement de l'asthme grave partiellement contrôlé ou non contrôlé avec un inhibiteur de pde4 (et en combinaison avec un modificateur des leucotriènes) |
| EP2949321A1 (fr) | 2014-05-26 | 2015-12-02 | Sanovel Ilac Sanayi ve Ticaret A.S. | Formulations multicouche de fexofénadine et de montélukast |
| WO2017182644A1 (fr) | 2016-04-22 | 2017-10-26 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Formulations de montélukast sodique et de fumarate de rupatadine en comprimés |
| WO2017182641A1 (fr) | 2016-04-22 | 2017-10-26 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Formulations de comprimé bicouche de montélukast et de rupatadine |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101278572B1 (ko) * | 2011-10-18 | 2013-06-25 | 주식회사 네비팜 | 류코트리엔 길항제와 에피나스틴의 복합제제 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994000111A1 (fr) * | 1992-06-26 | 1994-01-06 | Merck & Co., Inc. | Procede de transformation en spheres recourant a des resines chargees |
-
1996
- 1996-10-31 AU AU72741/96A patent/AU709301B2/en not_active Ceased
- 1996-10-31 EP EP96934274A patent/EP0859600A1/fr not_active Ceased
- 1996-10-31 WO PCT/CA1996/000724 patent/WO1997016173A1/fr not_active Application Discontinuation
- 1996-10-31 JP JP9516946A patent/JPH11514382A/ja not_active Withdrawn
- 1996-10-31 CA CA 2236175 patent/CA2236175A1/fr not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994000111A1 (fr) * | 1992-06-26 | 1994-01-06 | Merck & Co., Inc. | Procede de transformation en spheres recourant a des resines chargees |
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 123, no. 23, 4 December 1995, Columbus, Ohio, US; abstract no. 305952, XP002028053 * |
| D.F.SCHOORS ET AL.: "SINGLE DOSE PHARMACOKINETICS,SAFETY AND TOLERABILITY OF MK-0476,A NEW LEUKOTRIENE D4-RECEPTOR ANTAGONIST,IN HEALTHY VOLUNTEERS", BR. J. CLIN. PHARM., vol. 40, no. 3, 1995, pages 277 - 280 * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003035036A1 (fr) * | 2001-10-26 | 2003-05-01 | Merck Frosst Canada & Co. | Formulation de granules de montelukast |
| AU2002333134B2 (en) * | 2001-10-26 | 2007-08-02 | Merck Canada Inc. | Montelukast granule formulation |
| US8007830B2 (en) | 2001-10-26 | 2011-08-30 | Merck Frosst Canada & Co. | Granule formation |
| KR101094084B1 (ko) * | 2001-10-26 | 2011-12-15 | 머크 캐나다 인크. | 몬테루카스트 과립 제형 |
| HRP20040367B1 (en) * | 2001-10-26 | 2012-07-31 | Merck@Frosst@Canada@@@Co | Montelukast granule formulation |
| CZ298224B6 (cs) * | 2003-04-29 | 2007-07-25 | Pliva Istrazivanje I Razvoj D.O.O. | Farmaceutická kompozice obsahující jako úcinnou látku ribavirin a zpusob její výroby |
| WO2007077135A1 (fr) | 2005-12-30 | 2007-07-12 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Préparation pharmaceutique contenant du montélukast |
| WO2014012954A1 (fr) | 2012-07-18 | 2014-01-23 | Takeda Gmbh | Traitement de l'asthme sévère partiellement régulé ou non régulé |
| WO2015110394A1 (fr) | 2014-01-22 | 2015-07-30 | Takeda Gmbh | Traitement de l'asthme grave partiellement contrôlé ou non contrôlé avec un inhibiteur de pde4 (et en combinaison avec un modificateur des leucotriènes) |
| EP2949321A1 (fr) | 2014-05-26 | 2015-12-02 | Sanovel Ilac Sanayi ve Ticaret A.S. | Formulations multicouche de fexofénadine et de montélukast |
| WO2017182644A1 (fr) | 2016-04-22 | 2017-10-26 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Formulations de montélukast sodique et de fumarate de rupatadine en comprimés |
| WO2017182641A1 (fr) | 2016-04-22 | 2017-10-26 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Formulations de comprimé bicouche de montélukast et de rupatadine |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7274196A (en) | 1997-05-22 |
| AU709301B2 (en) | 1999-08-26 |
| EP0859600A1 (fr) | 1998-08-26 |
| JPH11514382A (ja) | 1999-12-07 |
| CA2236175A1 (fr) | 1997-05-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0814782B1 (fr) | Composition pharmaceutique stabilisee a l'aide d'un agent de base | |
| US7220762B1 (en) | Methods for stabilizing benzimidazole compounds | |
| JPH0768125B2 (ja) | 酸不安定化合物の内服用製剤 | |
| CA1273877A (fr) | Formule de comprimes d'agents antibacteriens a base d'acide quinoleine-carboxylique | |
| NZ227032A (en) | Stabilised ace inhibitors, a process for their preparation and stable pharmaceutical compositions therefrom | |
| EP1004305A1 (fr) | Compositions stabilisees contenant des composes du type benzimidazole | |
| CA2083683C (fr) | Formulation stable a base de sel d'analapril; methode de preparation et utilisation | |
| CN113939289A (zh) | 一种含有布鲁顿氏酪氨酸激酶抑制剂的口服固体片剂及其制备方法 | |
| JP4709379B2 (ja) | レボチロキシンナトリウム含有医薬製剤 | |
| JP4127740B2 (ja) | 安定化したベンズイミダゾール系化合物含有組成物 | |
| AU709301B2 (en) | New technology for wet granulation | |
| EP1976522B1 (fr) | Préparation pharmaceutique contenant du montélukast | |
| US20080102120A1 (en) | Solid Pharmaceutical Composition Comprising Valsartan | |
| JP2002520296A (ja) | 薬剤レボチロキシン製剤 | |
| AU621706B2 (en) | Stabilizing system for solid dosage forms | |
| EP0952823B1 (fr) | Compositions pharmaceutiques stabilisees et procede pour leur preparation | |
| ZA200308594B (en) | Granular preparations of a gaboxadol. | |
| JP2001270827A (ja) | ベンズイミダゾール系化合物含有錠剤 | |
| CN112057427A (zh) | 一种含有布鲁顿氏酪氨酸激酶抑制剂的口服固体片剂及其制备方法 | |
| GB2372702A (en) | Stable fosinopril sodium tablet formulation | |
| RU2287328C2 (ru) | Твердый препарат с высоким всасыванием | |
| WO2007029124A2 (fr) | Formulations contenant de l acide libre de pantoprazole et les sels de ce dernier | |
| JPH0820537A (ja) | 抗潰瘍剤含有固形製剤 | |
| JPH09110698A (ja) | 経口用医薬組成物の製造法 | |
| RU2257890C2 (ru) | Способ получения устойчивых фармацевтических композиций в форме таблеток, содержащих омепразол, и фармацевтические композиции, полученные таким способом |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): AL AM AU AZ BA BB BG BR BY CA CN CU CZ EE GE HU IL IS JP KG KR KZ LC LK LR LT LV MD MG MK MN MX NO NZ PL RO RU SG SI SK TJ TM TR TT UA US UZ VN AM AZ BY KG KZ MD RU TJ TM |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG |
|
| DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| WWE | Wipo information: entry into national phase |
Ref document number: 1996934274 Country of ref document: EP |
|
| ENP | Entry into the national phase |
Ref document number: 2236175 Country of ref document: CA Kind code of ref document: A Ref document number: 2236175 Country of ref document: CA |
|
| ENP | Entry into the national phase |
Ref document number: 1997 516946 Country of ref document: JP Kind code of ref document: A |
|
| WWP | Wipo information: published in national office |
Ref document number: 1996934274 Country of ref document: EP |
|
| WWR | Wipo information: refused in national office |
Ref document number: 1996934274 Country of ref document: EP |
|
| WWW | Wipo information: withdrawn in national office |
Ref document number: 1996934274 Country of ref document: EP |