CA2252609C - Polyol composition - Google Patents
Polyol composition Download PDFInfo
- Publication number
- CA2252609C CA2252609C CA002252609A CA2252609A CA2252609C CA 2252609 C CA2252609 C CA 2252609C CA 002252609 A CA002252609 A CA 002252609A CA 2252609 A CA2252609 A CA 2252609A CA 2252609 C CA2252609 C CA 2252609C
- Authority
- CA
- Canada
- Prior art keywords
- mannitol
- polyols
- composition according
- sorbitol
- lactitol
- 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
- 229920005862 polyol Polymers 0.000 title claims abstract description 96
- 150000003077 polyols Chemical class 0.000 title claims abstract description 96
- 239000000203 mixture Substances 0.000 title claims abstract description 78
- 238000001694 spray drying Methods 0.000 claims abstract description 17
- 239000011230 binding agent Substances 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000000594 mannitol Substances 0.000 claims description 75
- 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 claims description 72
- 229930195725 Mannitol Natural products 0.000 claims description 72
- 235000010355 mannitol Nutrition 0.000 claims description 72
- 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 claims description 46
- 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 claims description 46
- 239000000600 sorbitol Substances 0.000 claims description 46
- 235000010356 sorbitol Nutrition 0.000 claims description 46
- 239000000832 lactitol Substances 0.000 claims description 29
- 235000010448 lactitol Nutrition 0.000 claims description 29
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 claims description 29
- 229960003451 lactitol Drugs 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000005507 spraying Methods 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 6
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 6
- 238000003260 vortexing Methods 0.000 claims description 6
- 239000000811 xylitol Substances 0.000 claims description 6
- 235000010447 xylitol Nutrition 0.000 claims description 6
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 6
- 229960002675 xylitol Drugs 0.000 claims description 6
- 238000005469 granulation Methods 0.000 claims description 5
- 230000003179 granulation Effects 0.000 claims description 5
- SERLAGPUMNYUCK-YJOKQAJESA-N 6-O-alpha-D-glucopyranosyl-D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SERLAGPUMNYUCK-YJOKQAJESA-N 0.000 claims description 4
- 239000004386 Erythritol Substances 0.000 claims description 3
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 3
- 235000019414 erythritol Nutrition 0.000 claims description 3
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 3
- 229940009714 erythritol Drugs 0.000 claims description 3
- 238000009477 fluid bed granulation Methods 0.000 abstract 1
- 235000019589 hardness Nutrition 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 238000007906 compression Methods 0.000 description 9
- 230000006835 compression Effects 0.000 description 9
- 239000000470 constituent Substances 0.000 description 7
- 238000001665 trituration Methods 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000012916 structural analysis Methods 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000005846 sugar alcohols Chemical class 0.000 description 3
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- 239000005041 Mylar™ Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 229920005903 polyol mixture Polymers 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000004376 Sucralose Substances 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 235000010358 acesulfame potassium Nutrition 0.000 description 1
- 239000000619 acesulfame-K Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 229940124827 caffeine tablet Drugs 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 238000003181 co-melting Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940109275 cyclamate Drugs 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940034008 mannitol / sorbitol Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- ITVGXXMINPYUHD-CUVHLRMHSA-N neohesperidin dihydrochalcone Chemical compound C1=C(O)C(OC)=CC=C1CCC(=O)C(C(=C1)O)=C(O)C=C1O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 ITVGXXMINPYUHD-CUVHLRMHSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2/00—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic
- B01J2/16—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic by suspending the powder material in a gas, e.g. in fluidised beds or as a falling curtain
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/26—Hexahydroxylic alcohols
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Pulleys (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19615418A DE19615418A1 (de) | 1996-04-22 | 1996-04-22 | Polyol-Zusammensetzung |
| DE19615418.9 | 1996-04-22 | ||
| PCT/EP1997/001787 WO1997039739A2 (de) | 1996-04-22 | 1997-04-10 | Polyol-zusammensetzung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2252609A1 CA2252609A1 (en) | 1997-10-30 |
| CA2252609C true CA2252609C (en) | 2007-01-30 |
Family
ID=7791693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002252609A Expired - Lifetime CA2252609C (en) | 1996-04-22 | 1997-04-10 | Polyol composition |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6165511A (enExample) |
| EP (1) | EP0896528B1 (enExample) |
| JP (1) | JP4343272B2 (enExample) |
| CN (1) | CN1147290C (enExample) |
| AT (1) | ATE210971T1 (enExample) |
| CA (1) | CA2252609C (enExample) |
| CZ (1) | CZ291589B6 (enExample) |
| DE (2) | DE19615418A1 (enExample) |
| DK (1) | DK0896528T3 (enExample) |
| ES (1) | ES2169385T3 (enExample) |
| ID (1) | ID17384A (enExample) |
| MY (1) | MY116890A (enExample) |
| PT (1) | PT896528E (enExample) |
| RU (1) | RU2184535C2 (enExample) |
| TW (1) | TWI237567B (enExample) |
| WO (1) | WO1997039739A2 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2271839A1 (en) * | 1996-11-15 | 1998-05-28 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Process for the production of shaped or unshaped polyol materials |
| US20030203036A1 (en) | 2000-03-17 | 2003-10-30 | Gordon Marc S. | Systems and processes for spray drying hydrophobic drugs with hydrophilic excipients |
| GB9716432D0 (en) | 1997-08-05 | 1997-10-08 | Cerestar Holding Bv | Tableting of erythritol |
| FI107732B (fi) | 1998-03-18 | 2001-09-28 | Xyrofin Oy | Laktitolin kiteyttäminen, kiteinen laktitolituote ja sen käyttö |
| DE19943491B4 (de) | 1999-09-10 | 2010-04-01 | Südzucker AG Mannheim/Ochsenfurt | Verbesserte Komprimate |
| US6872414B1 (en) | 1999-09-20 | 2005-03-29 | Xyrofin Oy | Anhydrous lactitol crystals, a product containing the same and a process for the preparation thereof as well as use thereof |
| US7575761B2 (en) | 2000-06-30 | 2009-08-18 | Novartis Pharma Ag | Spray drying process control of drying kinetics |
| US20030188679A1 (en) * | 2000-08-25 | 2003-10-09 | Eugen Schwarz | Powdered mannitol and mannitol-containing compositions |
| AU2001294250A1 (en) * | 2000-10-16 | 2002-04-29 | Daiichi Pharmaceutical Co., Ltd. | Medicinal compositions quickly disintegrating in the oral cavity and process forproducing the same |
| CA2464656C (en) * | 2001-11-01 | 2013-07-16 | Nektar Therapeutics | Spray drying methods and compositions thereof |
| CA2363528A1 (en) * | 2001-11-19 | 2003-05-19 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Immediate release tablet containing naproxen sodium |
| AU2002217982A1 (en) * | 2001-11-29 | 2003-06-17 | Penwest Pharmaceutical Company | Process for co-spray drying liquid herbal extracts with dry silicified mcc |
| DE10161402A1 (de) † | 2001-12-13 | 2003-06-18 | Merck Patent Gmbh | Verfahren zur Herstellung von direkt tablettierbarem beta-Mannit |
| US7118765B2 (en) * | 2001-12-17 | 2006-10-10 | Spi Pharma, Inc. | Co-processed carbohydrate system as a quick-dissolve matrix for solid dosage forms |
| FI20021312L (fi) | 2002-07-03 | 2004-01-04 | Danisco Sweeteners Oy | Polyolikoostumusten kiteyttäminen, kiteinen polyolikoostumustuote ja sen käyttö |
| DE10240778A1 (de) * | 2002-08-30 | 2004-03-11 | Merck Patent Gmbh | Verfahren zur Herstellung von direkt tablettierbarem a-Mannit |
| AU2003298762A1 (en) * | 2002-11-26 | 2004-06-18 | Hercules Incorporated | Soluble, associative carboxymethylcellulose, method of making, and uses thereof |
| JP2004285052A (ja) * | 2003-03-06 | 2004-10-14 | Lion Corp | 化粧料組成物 |
| WO2004095942A2 (de) * | 2003-04-30 | 2004-11-11 | Ipc Prozess Center Gmbh & Co. | Coffein enthaltende tablette |
| KR20060015316A (ko) * | 2003-05-28 | 2006-02-16 | 넥타르 테라퓨틱스 | 아미노산 및/또는 인지질로 부분 또는 완전 코팅된수불용성 활성제 미립자의 제조를 위한 알코올성 수용액의분무 건조법 |
| US20090208576A1 (en) * | 2006-03-31 | 2009-08-20 | Gandhi Anilkumar S | Orally Disintegrating Tablets |
| WO2008079342A2 (en) * | 2006-12-21 | 2008-07-03 | Mallinckrodt Inc. | Composition of and method for preparing orally disintegrating tablets |
| DE102008014237A1 (de) * | 2008-03-14 | 2009-09-17 | J. Rettenmaier & Söhne Gmbh + Co. Kg | Direktverpressbares Tablettierhilfsmittel |
| ES2720626T3 (es) * | 2008-06-20 | 2019-07-23 | Merck Patent Gmbh | Combinación de poliol compresible directamente |
| EP2299982B1 (de) | 2008-06-20 | 2018-04-04 | Merck Patent GmbH | Direkt verpressbare und schnell zerfallende tablettenmatirx |
| AU2010223105B2 (en) * | 2009-03-09 | 2016-05-12 | Spi Pharma, Inc. | Highly compactable and durable direct compression excipients and excipient systems |
| DK2228175T3 (da) | 2009-03-12 | 2013-09-08 | Ferton Holding Sa | Anvendelse af pulver eller pulverblanding til fremstilling af et middel til pulverstrålerengøring af tandoverflader |
| PT2238974E (pt) * | 2009-04-09 | 2013-07-09 | E Pharma Trento Spa | Granulado para a formulação de comprimidos orodispersíveis |
| US20120114717A1 (en) * | 2009-07-10 | 2012-05-10 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Tableting agent having a low water content, and method for the production thereof |
| PT2451446E (pt) * | 2009-07-10 | 2014-05-12 | Merck Patent Gmbh | Composição para a produção de comprimidos e processo para a sua produção |
| US20110027445A1 (en) * | 2009-07-28 | 2011-02-03 | Heartland Sweeteners, LLC | No-calorie sweetener compositions |
| US20110027444A1 (en) * | 2009-07-28 | 2011-02-03 | Heartland Sweeteners, LLC | No-calorie sweetener compositions |
| US20110027446A1 (en) * | 2009-07-28 | 2011-02-03 | Heartland Sweeteners, LLC | No-calorie sweetener compositions |
| US20120149784A1 (en) | 2009-08-18 | 2012-06-14 | Cargill ,Incorporated | Tabletting of erythritol and isomalt |
| EP2384742A1 (en) | 2010-05-03 | 2011-11-09 | The Jordanian Pharmaceutical Manufacturing Co. | Pharmaceutical excipient, method for its preparation and use thereof |
| US20130177668A1 (en) | 2010-09-07 | 2013-07-11 | Cargill ,Incorporated | Solidified sugar alcohol mixture |
| WO2012079671A2 (de) * | 2010-12-17 | 2012-06-21 | Merck Patent Gmbh | VERFAHREN ZUR HERSTELLUNG VON DIREKT TABLETTIERBAREM δ-MANNIT |
| EP2683365A1 (de) * | 2011-03-09 | 2014-01-15 | Basf Se | Pharmazeutische formulierung für die herstellung von schnell zerfallenden tabletten |
| CN104095184B (zh) * | 2014-07-15 | 2016-03-30 | 浙江华康药业股份有限公司 | 一种粒状复合糖醇及其制备方法 |
| EP3206671B1 (en) | 2014-10-16 | 2024-06-12 | Cargill, Incorporated | Process for preparing a directly compressible erythritol and uses thereof |
| CN104447898B (zh) * | 2014-11-06 | 2017-03-29 | 山东绿健生物技术有限公司 | 一种固体乳糖醇及其制备方法与应用 |
| EP4183389A1 (en) | 2021-11-18 | 2023-05-24 | KRKA, d.d., Novo mesto | Pharmaceutical composition comprising apremilast |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3245170A1 (de) * | 1982-12-07 | 1984-06-07 | Merck Patent Gmbh, 6100 Darmstadt | Verbesserter sorbit, verfahren zur herstellung und verwendung |
| DE69022861T2 (de) * | 1989-01-24 | 1996-04-04 | Spi Polyols Inc | Kryoschützende kristalline Sorbitolkügelchen. |
| FR2670398B1 (fr) * | 1990-12-14 | 1995-02-17 | Roquette Freres | Composition pulverulente directement compressible et procede d'obtention. |
| US5158789A (en) * | 1991-08-09 | 1992-10-27 | Ici Americas Inc. | Melt cocrystallized sorbitol/xylitol compositions |
| US5876754A (en) * | 1992-01-17 | 1999-03-02 | Alfatec-Pharma Gmbh | Solid bodies containing active substances and a structure consisting of hydrophilic macromolecules, plus a method of producing such bodies |
| FR2710637B1 (fr) * | 1993-09-28 | 1995-12-08 | Roquette Freres | Mannitol pulvérulent de friabilité modérée et son procédé de préparation. |
-
1996
- 1996-04-22 DE DE19615418A patent/DE19615418A1/de not_active Withdrawn
-
1997
- 1997-04-10 JP JP53767397A patent/JP4343272B2/ja not_active Expired - Lifetime
- 1997-04-10 DK DK97920646T patent/DK0896528T3/da active
- 1997-04-10 US US09/171,536 patent/US6165511A/en not_active Expired - Lifetime
- 1997-04-10 RU RU98121204/14A patent/RU2184535C2/ru active
- 1997-04-10 EP EP97920646A patent/EP0896528B1/de not_active Revoked
- 1997-04-10 DE DE59705894T patent/DE59705894D1/de not_active Revoked
- 1997-04-10 CA CA002252609A patent/CA2252609C/en not_active Expired - Lifetime
- 1997-04-10 CN CNB97194024XA patent/CN1147290C/zh not_active Expired - Lifetime
- 1997-04-10 WO PCT/EP1997/001787 patent/WO1997039739A2/de not_active Ceased
- 1997-04-10 CZ CZ19983385A patent/CZ291589B6/cs not_active IP Right Cessation
- 1997-04-10 AT AT97920646T patent/ATE210971T1/de not_active IP Right Cessation
- 1997-04-10 ES ES97920646T patent/ES2169385T3/es not_active Expired - Lifetime
- 1997-04-10 PT PT97920646T patent/PT896528E/pt unknown
- 1997-04-10 ID IDP971194A patent/ID17384A/id unknown
- 1997-04-17 MY MYPI97001672A patent/MY116890A/en unknown
- 1997-04-18 TW TW086105071A patent/TWI237567B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TWI237567B (en) | 2005-08-11 |
| US6165511A (en) | 2000-12-26 |
| CN1147290C (zh) | 2004-04-28 |
| EP0896528B1 (de) | 2001-12-19 |
| WO1997039739A2 (de) | 1997-10-30 |
| RU2184535C2 (ru) | 2002-07-10 |
| HK1019202A1 (en) | 2000-01-28 |
| WO1997039739A3 (de) | 1997-11-27 |
| ES2169385T3 (es) | 2002-07-01 |
| DE19615418A1 (de) | 1997-10-23 |
| PT896528E (pt) | 2002-06-28 |
| JP2000508668A (ja) | 2000-07-11 |
| CA2252609A1 (en) | 1997-10-30 |
| CN1216466A (zh) | 1999-05-12 |
| CZ291589B6 (cs) | 2003-04-16 |
| JP4343272B2 (ja) | 2009-10-14 |
| DK0896528T3 (da) | 2002-04-08 |
| EP0896528A2 (de) | 1999-02-17 |
| ID17384A (id) | 1997-12-24 |
| DE59705894D1 (de) | 2002-01-31 |
| ATE210971T1 (de) | 2002-01-15 |
| MY116890A (en) | 2004-04-30 |
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