US20030031708A1 - Synergistic filler composition - Google Patents
Synergistic filler composition Download PDFInfo
- Publication number
- US20030031708A1 US20030031708A1 US09/915,057 US91505701A US2003031708A1 US 20030031708 A1 US20030031708 A1 US 20030031708A1 US 91505701 A US91505701 A US 91505701A US 2003031708 A1 US2003031708 A1 US 2003031708A1
- Authority
- US
- United States
- Prior art keywords
- tablet
- composition
- microcrystalline cellulose
- copolymer
- pvp
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 239000000945 filler Substances 0.000 title claims abstract description 15
- 230000002195 synergetic effect Effects 0.000 title claims abstract description 13
- 229920001577 copolymer Polymers 0.000 claims abstract description 19
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims abstract description 15
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims abstract description 15
- 239000008108 microcrystalline cellulose Substances 0.000 claims abstract description 11
- 229940016286 microcrystalline cellulose Drugs 0.000 claims abstract description 11
- 238000007906 compression Methods 0.000 claims abstract description 7
- 230000006835 compression Effects 0.000 claims abstract description 7
- 229940079593 drug Drugs 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 19
- GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 claims description 7
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 229910052681 coesite Inorganic materials 0.000 description 3
- 229910052906 cristobalite Inorganic materials 0.000 description 3
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 3
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910052682 stishovite Inorganic materials 0.000 description 3
- 229910052905 tridymite Inorganic materials 0.000 description 3
- 208000029618 autoimmune pulmonary alveolar proteinosis Diseases 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229960004166 diltiazem Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229960005489 paracetamol Drugs 0.000 description 2
- 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
- 235000019739 Dicalciumphosphate Nutrition 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
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
Images
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
- A61K9/2022—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
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
Definitions
- This invention relates to pharmaceutical tableting, and, more particularly, to a synergistic filler composition which provides increased tablet hardness and low friability at low compression forces without increasing the size of the tablet.
- FIG. 1 is a plot of tablet hardness (KP) vs. concentration (wt. %) of PVP-VA copolymer in a composition with silicified microcrystalline cellulose (silicified MCC/ProSolv®) at a given compression force.
- FIG. 2 is a similar plot for mixtures of copolymer and microcrystalline cellulose (MCC 102 ).
- FIG. 3 is a similar plot for a drug tablet of 67 wt. % acetaminophen (APAP) and silicified microcrystalline cellulose, with and without PVP/VA copolymer.
- APAP 67 wt. % acetaminophen
- silicified microcrystalline cellulose with and without PVP/VA copolymer.
- FIG. 4 is a similar plot as FIG. 3 for a composition containing microcrystalline cellulose.
- FIG. 5 is a similar plot of 60% aspirin and silicified microcellulose with and without PVP/VA copolymer.
- FIG. 6 is a similar plot of a drug tablet with 60 wt. % aspirin and a mix of microcrystalline cellulose (MCC 102) with and without PVP/VA copolymer.
- FIG. 7 is a similar plot as FIG. 6 of a drug tablet with 67 wt. % diltiazem HCl as the model drug.
- synergistic filler composition for making pharmaceutical tablets of increased tablet hardness and low friability without substantially increasing the size of the tablet, comprising (a) a PVP-VA copolymer and (b) microcrystalline cellulose.
- compositions are those wherein (b) is a silicified microcrystalline cellulose; and (a) is present in an amount of about 5-30%; most preferably 10-20%.
- compositions are those wherein (a) comprises, by weight, 80-60% PVP and 20-40% VA.
- synergistic filler compositions of (a) vinyl pyrrolidone-vinyl acetate copolymers, and (b) microcrystalline cellulose, preferably silicified microcrystalline cellulose, which provide a synergistic increase in hardness, and a synergistic decrease in friability, for tableted drugs containing such fillers.
- FIGS. 1 and 2 shows a plot of tablet hardness (KP) vs. concentration (wt. %) of PVP-VA copolymer in a composition with microcrystalline cellulose at a given compression force of 2000, 4000 and 6000 lbs.
- the composition of the invention provides a synergistic increase in tablet compressibility (hardness) with an increase in the concentration of PVP-VA copolymer in the composition up to about 30 wt. % of PVP/VA copolymer, as evidenced by the convex shape of the curve.
- the maximum synergistic effect is obtained at about 20 wt. % PVP-VA copolymer. Further increases in copolymer produces only marginal improvement in tablet hardness.
- microcrystalline cellulose component of the composition is available commercially as ProSolv® (silicified microcrystalline cellulose) and as MCC 102 (microcrystalline cellulose).
- composition of the invention were obtained similarly for drugs which are difficult to compress into small tablets without using an excessive amount of filler/binder. Such large amounts of filler/binder would preclude formulation of the drug into tablets of high dosage.
- FIGS. 3 and 4 there is shown the manufacture of drug-containing tablets with the composition of the invention using acetaminophen as a model drug.
- FIGS. 5-6 60 Aspirin 37 Copolymer (27 + 10) 2 PVPP (XL) 0.5 SiO 2 0.5 Mg stearate 100
- FIG. 7 65 Diltiazem HCI 32 Copolymer (22 + 10) 2 PVPP (XL) 0.5 SiO 2 0.5 Mg stearate 100
- the invention composition herein provides a synergistic action in drug tableting formulations of even difficult to compress drugs.
- the observed hardness is sufficient to prevent damage to the tablet upon further processing of the tablet, including coating and packaging.
- the tablet hardness obtained herein is preferably at least 3 KP, and its friability is ⁇ 0.7%, usually ⁇ 0.5%. Both properties are indicative of a new and improved composition in the field of drug tableting.
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- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
A synergistic filler composition for making pharmaceutical tablets of sufficient tablet hardness at low compression force, and low friability, to preclude damage to the tablet upon further processing, and without requiring a substantial increase in the size of the tablet, comprising (a) a PVP-VA copolymer and (b) a microcrystalline cellulose.
Description
- 1. Field of the Invention
- This invention relates to pharmaceutical tableting, and, more particularly, to a synergistic filler composition which provides increased tablet hardness and low friability at low compression forces without increasing the size of the tablet.
- 2. Description of the Prior Art
- Many commercial filler materials are used including microcrystalline cellulose and silicified microcrystalline cellulose inn the manufacture of pharmaceutical tablets. Such materials are described in the paper by Tobyn, M. J. in Int. J. of Pharmaceutics, 169, 183-194 (1998). However drugs which are difficult to compress require tableting machines which can operate at high compression forces in order to provide suitable hardness and low friability properties. Also, large amounts of the filler may be necessary to achieve these results, which, disadvantageously, increases the size of the tablet.
- Accordingly, it is an object of this invention to provide a drug tableting filler composition of two components which act synergistically with respect to increasing hardness and decreasing friability for pharmaceutical tablets at a given compression force, and without increasing the size of the tablet.
- This and other objects and features of the invention will be made apparent from the following description of the invention
- FIG. 1 is a plot of tablet hardness (KP) vs. concentration (wt. %) of PVP-VA copolymer in a composition with silicified microcrystalline cellulose (silicified MCC/ProSolv®) at a given compression force.
- FIG. 2 is a similar plot for mixtures of copolymer and microcrystalline cellulose (MCC 102).
- FIG. 3 is a similar plot for a drug tablet of 67 wt. % acetaminophen (APAP) and silicified microcrystalline cellulose, with and without PVP/VA copolymer.
- FIG. 4 is a similar plot as FIG. 3 for a composition containing microcrystalline cellulose.
- FIG. 5 is a similar plot of 60% aspirin and silicified microcellulose with and without PVP/VA copolymer.
- FIG. 6 is a similar plot of a drug tablet with 60 wt. % aspirin and a mix of microcrystalline cellulose (MCC 102) with and without PVP/VA copolymer.
- FIG. 7 is a similar plot as FIG. 6 of a drug tablet with 67 wt. % diltiazem HCl as the model drug.
- What is described herein is a synergistic filler composition for making pharmaceutical tablets of increased tablet hardness and low friability without substantially increasing the size of the tablet, comprising (a) a PVP-VA copolymer and (b) microcrystalline cellulose.
- Preferred compositions are those wherein (b) is a silicified microcrystalline cellulose; and (a) is present in an amount of about 5-30%; most preferably 10-20%.
- Other preferred compositions are those wherein (a) comprises, by weight, 80-60% PVP and 20-40% VA.
- In this invention, there is provided synergistic filler compositions of (a) vinyl pyrrolidone-vinyl acetate copolymers, and (b) microcrystalline cellulose, preferably silicified microcrystalline cellulose, which provide a synergistic increase in hardness, and a synergistic decrease in friability, for tableted drugs containing such fillers. These results are achieved herein with only a minimum amount of the filler composition, and without increasing the size of the tablet.
- The invention will be further described by reference to the experimental results illustrated in the drawings.
- Accordingly, FIGS. 1 and 2 shows a plot of tablet hardness (KP) vs. concentration (wt. %) of PVP-VA copolymer in a composition with microcrystalline cellulose at a given compression force of 2000, 4000 and 6000 lbs. As shown in FIGS. 1 and 2, the composition of the invention provides a synergistic increase in tablet compressibility (hardness) with an increase in the concentration of PVP-VA copolymer in the composition up to about 30 wt. % of PVP/VA copolymer, as evidenced by the convex shape of the curve. The maximum synergistic effect is obtained at about 20 wt. % PVP-VA copolymer. Further increases in copolymer produces only marginal improvement in tablet hardness.
- These results contrast with the individual components alone, or PVP-VA copolymer with other known fillers, such as lactose or dicalcium phosphate, where the hardness increase is observed to be only linear with increasing copolymer concentration.
- The microcrystalline cellulose component of the composition is available commercially as ProSolv® (silicified microcrystalline cellulose) and as MCC 102 (microcrystalline cellulose).
- The advantageous results demonstrated herein for the composition of the invention were obtained similarly for drugs which are difficult to compress into small tablets without using an excessive amount of filler/binder. Such large amounts of filler/binder would preclude formulation of the drug into tablets of high dosage.
- Referring now to FIGS. 3 and 4, there is shown the manufacture of drug-containing tablets with the composition of the invention using acetaminophen as a model drug.
COMPOSITIONS OF DRUG TABLETS (WT. %) FIGS. 3-4 67 APAP 30 Copolymer (25 cellulose + 5 PVP/VA) 2 PVPP (XL) 0.5 SiO2 (colloid) 0.5 Mg stearate 100 FIGS. 5-6 60 Aspirin 37 Copolymer (27 + 10) 2 PVPP (XL) 0.5 SiO2 0.5 Mg stearate 100 FIG. 7 65 Diltiazem HCI 32 Copolymer (22 + 10) 2 PVPP (XL) 0.5 SiO2 0.5 Mg stearate 100 - Similar synergistic effects were obtained for aspirin tablets containing (FIGS. 5 and 6) and for diltiazem HCl (FIG. 7) as model drugs.
- In summary, the invention composition herein provides a synergistic action in drug tableting formulations of even difficult to compress drugs. The observed hardness is sufficient to prevent damage to the tablet upon further processing of the tablet, including coating and packaging. The tablet hardness obtained herein is preferably at least 3 KP, and its friability is <0.7%, usually <0.5%. Both properties are indicative of a new and improved composition in the field of drug tableting.
- While the invention has been described with particular reference to certain embodiments thereof, it will be understood that changes and modifications may be made which are within the skill of the art. Accordingly, it is intended to be bound only by the following claims, in which:
Claims (8)
1. A synergistic filler composition for making pharmaceutical tablets of sufficient tablet hardness at low compression force, and low friability, to preclude damage to the tablet upon further processing, and without requiring a substantial increase in the size of the tablet, comprising (a) a PVP-VA copolymer and (b) a microcrystalline cellulose.
2. A composition according to claim 1 wherein (a) is present in an amount of about 5-30% by wt. of the composition.
3. A composition according to claim 2 wherein (a) is present in an amount of about 10-20% by wt.
4. A composition according to claim 1 wherein (a) comprises, by weight, 80−60% PVP and 20-40% VA.
5. A composition according to claim 1 wherein (b) is a silicified microcrystalline cellulose.
6. A pharmaceutical tablet including the synergistic filler composition of claim 1 and a drug.
7. A pharmaceutical tablet according to claim 6 wherein said drug is ordinarily a difficult to compress drug.
8. A pharmaceutical tablet according to claim 6 in which said tablet hardness is at least 3 KP, and its friability is <0.7.
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/915,057 US6524617B1 (en) | 2001-07-25 | 2001-07-25 | Synergistic filler composition |
| MXPA04000666A MXPA04000666A (en) | 2001-07-25 | 2002-05-10 | Synergistic filler composition. |
| DE60211916T DE60211916T2 (en) | 2001-07-25 | 2002-05-10 | SYNERGISTIC FILLING COMPOSITION |
| CA2454449A CA2454449C (en) | 2001-07-25 | 2002-05-10 | Synergistic filler composition of pvp-va and silicified mycrocrystalline cellulose for tablet dosage form |
| PCT/US2002/014586 WO2003011253A1 (en) | 2001-07-25 | 2002-05-10 | Synergistic filler composition |
| JP2003516485A JP4805537B2 (en) | 2001-07-25 | 2002-05-10 | Synergistic excipient composition |
| EP02734286A EP1416918B1 (en) | 2001-07-25 | 2002-05-10 | Synergistic filler composition |
| BRPI0211439-9A BRPI0211439B1 (en) | 2001-07-25 | 2002-05-10 | COMPOSITION OF SYNERGISTIC CHARGE AND PHARMACEUTICAL TABLET |
| RU2004105268/15A RU2304981C2 (en) | 2001-07-25 | 2002-05-10 | Synergetic filling agent composition |
| ES02734286T ES2266502T3 (en) | 2001-07-25 | 2002-05-10 | SYNTHETIC FILLING COMPOSITION. |
| AT02734286T ATE327738T1 (en) | 2001-07-25 | 2002-05-10 | SYNERGISTIC FILLING COMPOSITION |
| CNB028185161A CN1268320C (en) | 2001-07-25 | 2002-05-10 | Synergistic filler composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/915,057 US6524617B1 (en) | 2001-07-25 | 2001-07-25 | Synergistic filler composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| US20030031708A1 true US20030031708A1 (en) | 2003-02-13 |
| US6524617B1 US6524617B1 (en) | 2003-02-25 |
Family
ID=25435143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/915,057 Expired - Lifetime US6524617B1 (en) | 2001-07-25 | 2001-07-25 | Synergistic filler composition |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6524617B1 (en) |
| EP (1) | EP1416918B1 (en) |
| JP (1) | JP4805537B2 (en) |
| CN (1) | CN1268320C (en) |
| AT (1) | ATE327738T1 (en) |
| BR (1) | BRPI0211439B1 (en) |
| CA (1) | CA2454449C (en) |
| DE (1) | DE60211916T2 (en) |
| ES (1) | ES2266502T3 (en) |
| MX (1) | MXPA04000666A (en) |
| RU (1) | RU2304981C2 (en) |
| WO (1) | WO2003011253A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070036859A1 (en) * | 2005-08-11 | 2007-02-15 | Perry Ronald L | Sustained release antihistamine and decongestant composition |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6620900B2 (en) * | 2002-02-07 | 2003-09-16 | Isp Investments Inc. | Proliferous copolymer of vinyl pyrrolidone and vinyl acetate |
| EP1585502B9 (en) * | 2002-11-12 | 2012-05-09 | Elan Pharma International Limited | Fast-disintegrating solid dosage forms being not friable and comprising pullulan |
| US7704528B2 (en) * | 2003-05-05 | 2010-04-27 | Isp Investments Inc. | Binder composition and method for processing poorly compressible drugs into tablets of predetermined hardness and friability |
| US8168219B2 (en) * | 2005-11-30 | 2012-05-01 | Isp Investments Inc. | Synergistic binder composition, method for making same, and tablets of an active and said binder having advantageous hardness and friability |
| ES2738659T3 (en) * | 2013-03-12 | 2020-01-24 | Hercules Llc | Composition of polymer coated with co-processed silica |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU183408B (en) * | 1981-04-28 | 1984-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing oral ratard pharmaceutical compositions |
| US5326570A (en) * | 1991-07-23 | 1994-07-05 | Pharmavene, Inc. | Advanced drug delivery system and method of treating psychiatric, neurological and other disorders with carbamazepine |
| AU6824996A (en) * | 1995-08-17 | 1997-03-12 | Dyer, Alison Margaret | Controlled release products |
| AT413647B (en) * | 1998-11-26 | 2006-04-15 | Sandoz Ag | USE OF A COPOLYMERISATE OF 1-VINYL-2-PYRROLIDONE AND VINYL ACETATE FOR THE PREPARATION OF CEFUROXIMAXETIL-SUBJECTED TABLETS |
-
2001
- 2001-07-25 US US09/915,057 patent/US6524617B1/en not_active Expired - Lifetime
-
2002
- 2002-05-10 WO PCT/US2002/014586 patent/WO2003011253A1/en active IP Right Grant
- 2002-05-10 CN CNB028185161A patent/CN1268320C/en not_active Expired - Lifetime
- 2002-05-10 JP JP2003516485A patent/JP4805537B2/en not_active Expired - Lifetime
- 2002-05-10 AT AT02734286T patent/ATE327738T1/en not_active IP Right Cessation
- 2002-05-10 ES ES02734286T patent/ES2266502T3/en not_active Expired - Lifetime
- 2002-05-10 CA CA2454449A patent/CA2454449C/en not_active Expired - Lifetime
- 2002-05-10 MX MXPA04000666A patent/MXPA04000666A/en active IP Right Grant
- 2002-05-10 BR BRPI0211439-9A patent/BRPI0211439B1/en not_active IP Right Cessation
- 2002-05-10 RU RU2004105268/15A patent/RU2304981C2/en active
- 2002-05-10 DE DE60211916T patent/DE60211916T2/en not_active Expired - Lifetime
- 2002-05-10 EP EP02734286A patent/EP1416918B1/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070036859A1 (en) * | 2005-08-11 | 2007-02-15 | Perry Ronald L | Sustained release antihistamine and decongestant composition |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003011253A1 (en) | 2003-02-13 |
| CN1268320C (en) | 2006-08-09 |
| MXPA04000666A (en) | 2004-04-05 |
| ES2266502T3 (en) | 2007-03-01 |
| US6524617B1 (en) | 2003-02-25 |
| EP1416918B1 (en) | 2006-05-31 |
| CA2454449A1 (en) | 2003-02-13 |
| CN1556695A (en) | 2004-12-22 |
| DE60211916T2 (en) | 2007-01-04 |
| BRPI0211439B1 (en) | 2017-09-19 |
| EP1416918A1 (en) | 2004-05-12 |
| CA2454449C (en) | 2010-10-26 |
| RU2304981C2 (en) | 2007-08-27 |
| DE60211916D1 (en) | 2006-07-06 |
| JP4805537B2 (en) | 2011-11-02 |
| BR0211439A (en) | 2004-07-20 |
| ATE327738T1 (en) | 2006-06-15 |
| JP2005501049A (en) | 2005-01-13 |
| BRPI0211439B8 (en) | 2021-05-25 |
| RU2004105268A (en) | 2005-03-10 |
| EP1416918A4 (en) | 2004-08-18 |
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