WO1995007689A1 - Compositions containing swelling pharmaceuticals - Google Patents

Compositions containing swelling pharmaceuticals Download PDF

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Publication number
WO1995007689A1
WO1995007689A1 PCT/DK1994/000338 DK9400338W WO9507689A1 WO 1995007689 A1 WO1995007689 A1 WO 1995007689A1 DK 9400338 W DK9400338 W DK 9400338W WO 9507689 A1 WO9507689 A1 WO 9507689A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
swelling
eur
previous
active compound
Prior art date
Application number
PCT/DK1994/000338
Other languages
French (fr)
Inventor
Bent HØJGAARD
Original Assignee
Ferrosan A/S
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ferrosan A/S filed Critical Ferrosan A/S
Priority to AU76514/94A priority Critical patent/AU7651494A/en
Publication of WO1995007689A1 publication Critical patent/WO1995007689A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • A61K38/16Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/41Porphyrin- or corrin-ring-containing peptides
    • A61K38/42Haemoglobins; Myoglobins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2013Organic compounds, e.g. phospholipids, fats
    • A61K9/2018Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2022Organic macromolecular compounds
    • A61K9/205Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin

Definitions

  • This invention relates to a novel, solid composition in the form of capsules or tablets containing a swelling pharmaceutically active compound and having im ⁇ proved disintegration time and dissolution time.
  • the preparation of a pharmaceutical composition containing a swelling pharma ⁇ ceutical active compound may be difficult in that the swelling of the active com ⁇ pound may result in a too long disintegration time and a too long dissolution time.
  • One way of solving such problems is to add a disintegrant such as sodium carboxymethylcellulose and starches.
  • Another way of solving such problems is to reduce the particle size of the active compound.
  • compositions containing sparingly soluble, non-swelling compounds are prepared by a complex melting procedure using two or more ingredients such as the active compound and the carbohydrate.
  • compositions having a retarded action are known. Such com ⁇ positions are prepared by adding a swelling compound such as hydroxymethyl- cellulose to the composition.
  • Solid pharmaceutical compositions containing a swelling ingredient as well as a polysaccharide such as starch or a disaccharide such as glucose or lactose are known. As far as we know, none af such known compositions are in the form of capsules or tablets.
  • Methylcellulose granules are granules.
  • these known compositions are either to be used locally or they are technical excipients which are not to be absorbed by the patient.
  • haemoglobin compositions as a ferrous supplement to the diet of mammalian animals including man has been known for decades.
  • Some haemo ⁇ globin compositions are solid compositions and other compositions are used in dissolved form.
  • solid haemoglobin compositions When administering a solid haemoglobin composition, it is of the out- most importance to ensure that iron is released from the composition and thus is available for uptake by the patient.
  • the hitherto known, solid haemoglobin compositions do not have a sufficiently short disintegration time and/or short dis ⁇ solution time. Hitherto, no solid haemoglobin compositions fulfilling the requirements concerning disintegration time and dissolution time stated in the Pharmacopoeias have been available.
  • One object of this invention is to make available a composition containing a swelling pharmaceutically active compound and having an improved disin ⁇ tegration time leading to a preparation with an improved dissolution time.
  • Another further object of this invention is to make available a com- position containing a swelling pharmaceutically active compound which com ⁇ position can be prepared by a relatively simple mixing procedure of the ingre ⁇ washers.
  • a swelling pharmaceutical active compound is a pharmaceutical compound which in water makes a highly viscous, gel-like structure acting as barrier to diffusion and wetting of the core of the solid.
  • the swelling pharmaceutical active compound is a macro-molecular compound.
  • the molecular weight of the swelling pharmaceutical active compound could, for example, be above about 200, preferably above about 500, most preferred above about 1000.
  • the swelling pharmaceutical active compounds are highly vis ⁇ cous in water.
  • the swelling com ⁇ pound has a viscosity above about 5, preferably above about 15 cps, when measured in a solution containing 30 % (weight/weight) of the swelling com- pound or, if the swelling compound has a lower solubility, when measured in a saturated solution.
  • the viscosity of a 30 % (weight/weight) haemo ⁇ globin solution is about 24 cps.
  • the swelling pharmaceutically active compound may, for example, be haemo ⁇ globin, Ginko Biloba extracts, a glycosaminglycane or polysaccharides.
  • the content of the swelling pharmaceutically active compound in the composition of this invention is in the range 30 - 90 %, preferably in the range 50 - 75 % (weight/weight).
  • the monosaccharide used is dex ⁇ trose.
  • the monosaccharide alcohol used is sorbitol, mannitol, xylitol, lactitol or maltitol, preferably sorbitol.
  • the disaccharide used is as sucrose, fructose or lactose, preferably sucrose.
  • the oligosaccharide used in the com ⁇ positions of this invention does not contain more than 10 monosaccharide units, more preferred not more than 5 units.
  • the content of the mono-, di- or oligosaccharide or an alcohol thereof in the composition of this invention is in the range 5 - 50 %, preferably in the range 10 - 40 % (weight/weight).
  • compositions of this invention are prepared by simple mixing of the swelling pharmaceutically active compound and the carbohydrate.
  • the swelling pharmaceutically active compound and/or the mono-, di- or oligosaccharide or the alcohol thereof may be present in granulate form.
  • other excipients commonly used in the art may be added to the mixture. Examples of such additional compounds are other actives, buffering agents, stabilizing agents, lubricants, filling agents, diluents, disintegrating agents, humectants or binders.
  • compositions of this invention are prepared analogously with the preparation of similar known compositions.
  • the solid compositions of this invention are capsules or tablets.
  • the solid com ⁇ position may be uncoated, filmcoated or sugarcoated.
  • compositions of this invention are used analogously with the use of similar known compositions.
  • present invention is further illustrated by the following examples which, how ⁇ ever, are not to be interpreted limiting.
  • Haemoglobin was granulated in a high-shear mixer with glycerol without contact with water. The rest of the components and the granulate were mixed in a double cone mixer. Tablets were compressed on a single punch tablet press to a tensile strength of 7 ⁇ 1 kp.
  • the disintegration time was found to be 55 minutes.
  • the disintegration time was found to be 56 minutes.
  • the following ingredients were used: 350 mg of haemoglobin (spray-dried), 35 mg of glycerol (Ph.Eur.), 25 mg of ferrous fumarate, 132 mg of sucrose (Ph.Eur.), 29 mg of sodium carboxymethylcellulose (USP), 5 mg of silicon dioxide, colloidal (Ph.Eur.) and 3 mg of magnesium stearate (Ph.Eur.).
  • the mixing, compression and test procedures were as described in Example 1. The disintegration time was found to be 44 minutes.
  • the disintegration time was found to be 56 minutes.
  • the disintegration time was found to be 44 minutes.
  • the following ingredients were used: 350 mg of bovine haemoglobin (spray- dried), 42 mg of glycerol (Ph.Eur.), 6 mg of silicon dioxide, colloidal (Ph.Eur.), 132 mg of sucrose (Ph.Eur.), 28 mg of sodium carboxymethylcellulose (USP), 25 s mg of ferrous fumarate and 3 mg of magnesium stearate (Ph.Eur.).
  • Haemoglobin was granulated in a high-shear mixer with glycerol without contact with water. Silicon dioxide, colloidal, sucrose and sodium carboxymethylcellulose were mixed with the granulate in the high-shear mixer and sieved. Ferrous fumarate and magnesium stearate were mixed with the granulate in a double o cone mixer. Tablets were compressed on a rotary tablet press to a tensile strength of 7 ⁇ 1 kp.
  • the disintegration time was found to be 37 minutes. s
  • the dissolution time (ferrous) was measure as described in Ph.Eur., 2nd
  • the dissolution profile i.e., the percentage of iron dissolved in relation to the time from the start, is given in Table 1 below.
  • the dissolution 0 profile of the product described in Example 1c is given.
  • composition according to this invention has a substantial better dissolution profile than the composition not covered by the claims (Example 1c).

Abstract

The disintegration time of a solid composition in the form of a capsule or tablet containing a swelling compound is improved by adding a mono-, di- or oligosaccharide or an alcohol thereof.

Description

COMPOSITIONS CONTAINING SWELLING PHARMACEUTICALS
This invention relates to a novel, solid composition in the form of capsules or tablets containing a swelling pharmaceutically active compound and having im¬ proved disintegration time and dissolution time.
BACKGROUND OF THIS INVENTION
When preparing pharmaceutical compositions, it is important to secure that the active ingredient is absorbed by the patient at a desired and convenient rate. For some medical treatments, a rapid rate of absorption is desired and for other treatments, a retarded rate of absorption is desired. Also, medicaments having both a rapid onset of action and a prolonged action are on the market.
The preparation of a pharmaceutical composition containing a swelling pharma¬ ceutical active compound may be difficult in that the swelling of the active com¬ pound may result in a too long disintegration time and a too long dissolution time. One way of solving such problems is to add a disintegrant such as sodium carboxymethylcellulose and starches. Another way of solving such problems is to reduce the particle size of the active compound.
Until now, these known, general methods have proved unsuccessful.
For purposes deviating substantially from the object of this invention, the addition of carbohydrates to pharmaceutical compositions has been suggested. The pharmaceutically active compounds in these known compositions are sparingly soluble, non-swelling chemical compounds. Examples of such com¬ pounds are bendrofluazide Drug Dev.lnd.Pharm. 3 (1977), 439 et sea.), hydro- cortisone and prednisone (J.Pharm.Sci. 67 (1978), 979 et seg.), trimethoprim (Pharm.Acta.Helv. 58 (1983), 62 et seg.), hydrochlorothiazide (Drug Dev.lnd.- Pharm. W (1984), 1709 et seg.), carbamazepine and nitrazepam (Drug Dev.lnd.- Pharm. H (1985), 1957 et seg.).
Pharmaceutical compositions containing sparingly soluble, non-swelling compounds are prepared by a complex melting procedure using two or more ingredients such as the active compound and the carbohydrate.
Pharmaceutical compositions having a retarded action are known. Such com¬ positions are prepared by adding a swelling compound such as hydroxymethyl- cellulose to the composition.
Solid pharmaceutical compositions containing a swelling ingredient as well as a polysaccharide such as starch or a disaccharide such as glucose or lactose are known. As far as we know, none af such known compositions are in the form of capsules or tablets.
In Martindale, The Extra Pharmacopoeia, 26 (1972), such compositions are described. At page 1077, Arabon containing ceratonia and starch is desribed. At page 1084, Metamucil containing Psyllium hydrophilic and dextrose is described. At page 1073, Methylcellulose granules containing methylcellulose and lactose is described. At page 1093, "Compound Tragacanth Powder" con¬ taining tragacanth, starch and sucrose is described. Arabon, Metamucil and "Compound Tragacanth Powder" are powders.
Methylcellulose granules are granules. In addition, these known compositions are either to be used locally or they are technical excipients which are not to be absorbed by the patient.
It is known from J.Pharm.Pharmac. 20 (1968), 228 S et seg., that "the disin- tegration times did not correlate with the dissolution times". In addition, it appears from the last-mentioned paper that the addition of sorbitol resulted in a substantially longer disintegration time. It is mentioned in Drug Dev.lnd.Pharm. 3 (1977), 439 et seg., that "decreasing the solubility of the diluent decreased the disintegration time". Based upon this fact, the skilled art worker will draw the conclusion that increasing the solubility by adding a carbohydrate to a solid pharmaceutical composition will result in a composition having an increased disintegration time.
The use of haemoglobin compositions as a ferrous supplement to the diet of mammalian animals including man has been known for decades. Some haemo¬ globin compositions are solid compositions and other compositions are used in dissolved form.
When administering a solid haemoglobin composition, it is of the out- most importance to ensure that iron is released from the composition and thus is available for uptake by the patient. The hitherto known, solid haemoglobin compositions do not have a sufficiently short disintegration time and/or short dis¬ solution time. Hitherto, no solid haemoglobin compositions fulfilling the requirements concerning disintegration time and dissolution time stated in the Pharmacopoeias have been available.
One object of this invention is to make available a composition containing a swelling pharmaceutically active compound and having an improved disin¬ tegration time leading to a preparation with an improved dissolution time.
Another further object of this invention is to make available a com- position containing a swelling pharmaceutically active compound which com¬ position can be prepared by a relatively simple mixing procedure of the ingre¬ dients.
BRIEF DESCRIPTION OF THIS INVENTION
Surprisingly, it has been found that the presence of certain carbohydrates, i.e., mono-, di- or oligosaccharide or alcohols thereof, in a solid composition con¬ taining a swelling pharmaceutically active compound results in a composition having the desired disintegration time and the desired dissolution time.
As explained above in relation with the background of this invention, mixtures with several sorts of carbohydrates are know. These mixtures are used for various purposes. However, there is nothing in the known art teaching or indication that exactly mono-, di- or oligosaccharide and alcohols thereof have this desired effect. As proved in the examples below, polysaccharides does not have the desired effect.
DETAILED DESCRIPTION OF THIS INVENTION
A swelling pharmaceutical active compound is a pharmaceutical compound which in water makes a highly viscous, gel-like structure acting as barrier to diffusion and wetting of the core of the solid.
In a preferred embodiment of this invention, the swelling pharmaceutical active compound is a macro-molecular compound. The molecular weight of the swelling pharmaceutical active compound could, for example, be above about 200, preferably above about 500, most preferred above about 1000.
As stated above, the swelling pharmaceutical active compounds are highly vis¬ cous in water. In a preferred embodiment of this invention, the swelling com¬ pound has a viscosity above about 5, preferably above about 15 cps, when measured in a solution containing 30 % (weight/weight) of the swelling com- pound or, if the swelling compound has a lower solubility, when measured in a saturated solution. For example, the viscosity of a 30 % (weight/weight) haemo¬ globin solution is about 24 cps.
The swelling pharmaceutically active compound may, for example, be haemo¬ globin, Ginko Biloba extracts, a glycosaminglycane or polysaccharides. Preferably, the content of the swelling pharmaceutically active compound in the composition of this invention is in the range 30 - 90 %, preferably in the range 50 - 75 % (weight/weight).
In a preferred embodiment of this invention, the monosaccharide used is dex¬ trose. In another, preferred embodiment, the monosaccharide alcohol used is sorbitol, mannitol, xylitol, lactitol or maltitol, preferably sorbitol. In a still further embodiment of this invention, the disaccharide used is as sucrose, fructose or lactose, preferably sucrose. Preferably, the oligosaccharide used in the com¬ positions of this invention does not contain more than 10 monosaccharide units, more preferred not more than 5 units. Preferably, the content of the mono-, di- or oligosaccharide or an alcohol thereof in the composition of this invention is in the range 5 - 50 %, preferably in the range 10 - 40 % (weight/weight).
The compositions of this invention are prepared by simple mixing of the swelling pharmaceutically active compound and the carbohydrate. Before the mixing procedure, the swelling pharmaceutically active compound and/or the mono-, di- or oligosaccharide or the alcohol thereof may be present in granulate form. During the mixing process, also other excipients commonly used in the art may be added to the mixture. Examples of such additional compounds are other actives, buffering agents, stabilizing agents, lubricants, filling agents, diluents, disintegrating agents, humectants or binders.
In principle, the compositions of this invention are prepared analogously with the preparation of similar known compositions.
The solid compositions of this invention are capsules or tablets. The solid com¬ position may be uncoated, filmcoated or sugarcoated.
The compositions of this invention are used analogously with the use of similar known compositions. The present invention is further illustrated by the following examples which, how¬ ever, are not to be interpreted limiting.
Example 1
a) The following ingredients were used: 350 mg of haemoglobin (spray- dried), 35 mg of glycerol (Ph.Eur.), 25 mg of ferrous fumarate, 66 mg of sucrose (Ph.Eur.), 5 mg of silicon dioxide, colloidal (Ph.Eur.) and 3 mg of magnesium stearate (Ph.Eur.).
Haemoglobin was granulated in a high-shear mixer with glycerol without contact with water. The rest of the components and the granulate were mixed in a double cone mixer. Tablets were compressed on a single punch tablet press to a tensile strength of 7 ± 1 kp.
Disintegration times were measured as described in Ph.Eur., 2nd Ed., V.5.1.1 (1986) using discs.
The disintegration time was found to be 55 minutes.
b) Using the same ingredients as described in Example 1a, with the pro¬ viso that no sucrose was added, a disintegration time of 105 minutes was ob¬ tained.
c) Using the same ingredients as first described in this example (1a), with the proviso that 66 mg of maize starch was used instead of 66 mg of sucrose, a disintegration time of 150 minutes was obtained.
The above, comparative examples shows the surprising effect of using sucrose (55 minutes) compared with not using sucrose (105 minutes) and substituting sucrose for starch (150 minutes). Example 2
The following ingredients were used: 350 mg of haemoglobin (spray-dried), 35 mg of glycerol (Ph.Eur.), 25 mg of ferrous fumarate, 198 mg of sucrose (Ph.Eur.), 5 mg of silicon dioxide, colloidal (Ph.Eur.) and 3 mg of magnesium stearate (Ph.Eur.). The mixing, compression and test procedures were as de¬ scribed in Example 1.
The disintegration time was found to be 56 minutes.
Example 3
The following ingredients were used: 350 mg of haemoglobin (spray-dried), 35 mg of glycerol (Ph.Eur.), 25 mg of ferrous fumarate, 132 mg of sucrose (Ph.Eur.), 29 mg of sodium carboxymethylcellulose (USP), 5 mg of silicon dioxide, colloidal (Ph.Eur.) and 3 mg of magnesium stearate (Ph.Eur.). The mixing, compression and test procedures were as described in Example 1. The disintegration time was found to be 44 minutes.
Example 4
a) The following ingredients were used: 350 mg of haemoglobin (spray- dried), 35 mg of glycerol (Ph.Eur.), 25 mg of ferrous fumarate, 132 mg of man¬ nitol (Ph.Eur.), 5 mg of silicon dioxide, colloidal (Ph.Eur.) and 3 mg of mag¬ nesium stearate (Ph.Eur.). The mixing, compression and test procedures were as described in Example 1.
The disintegration time was found to be 56 minutes.
b) Using the same ingredients as described in 4a, with the proviso that 132 mg of maize starch were used instead of 132 mg of mannitol, a disintegration time of 130 minutes was obtained.
c) If, additionally, 28 mg of sodium carboxymethylcellulose were added to the ingredients mentioned in Example 4b, also a disintegration time of 130 minutes was obtained.
The above, comparative examples shows the surprising effect of using mannitol (56 minutes) compared with substituting mannitol for starch (130 minutes), with and without the addition of sodium carboxymethylcellulose.
Example 5
The following ingredients were used: 350 mg of haemoglobin (spray-dried), 35 mg of glycerol (Ph.Eur.), 25 mg of ferrous fumarate, 132 mg of sorbitol (Ph.Eur.), 5 mg of silicon dioxide, colloidal (Ph.Eur.) and 3 mg of magnesium stearate (Ph.Eur.). The mixing, compression and test procedures were as described in Example 1.
The disintegration time was found to be 44 minutes.
Example 6
The following ingredients were used: 350 mg of haemoglobin (spray-dried), 35 mg of Glycerol (Ph.Eur.), 25 mg of ferrous fumarate, 132 mg of maltodextrin (Glucidex 19, Roquette), 5 mg of silicon dioxide, colloidal (Ph.Eur.) and 3 mg of magnesium stearate (Ph.Eur.). The mixing, compression and test procedures were as described in Example 1.
The disintegration time was found to be 56 minutes. Example 7
The following ingredients were used: 350 mg of bovine haemoglobin (spray- dried), 42 mg of glycerol (Ph.Eur.), 6 mg of silicon dioxide, colloidal (Ph.Eur.), 132 mg of sucrose (Ph.Eur.), 28 mg of sodium carboxymethylcellulose (USP), 25 s mg of ferrous fumarate and 3 mg of magnesium stearate (Ph.Eur.).
Haemoglobin was granulated in a high-shear mixer with glycerol without contact with water. Silicon dioxide, colloidal, sucrose and sodium carboxymethylcellulose were mixed with the granulate in the high-shear mixer and sieved. Ferrous fumarate and magnesium stearate were mixed with the granulate in a double o cone mixer. Tablets were compressed on a rotary tablet press to a tensile strength of 7 ± 1 kp.
Disintegration times were measured as described in Ph.Eur., 2nd Ed., V.5.1 (1986) using discs.
The disintegration time was found to be 37 minutes. s The dissolution time (ferrous) was measure as described in Ph.Eur., 2nd
Ed., V.5.4 (1991). Test results are given in Figure 1 showing the dissolution pro¬ file.
The dissolution profile, i.e., the percentage of iron dissolved in relation to the time from the start, is given in Table 1 below. In this table, also the dissolution 0 profile of the product described in Example 1c is given.
As appears from this table, the composition according to this invention (Example 7) has a substantial better dissolution profile than the composition not covered by the claims (Example 1c). Percentage iron dissolved
Time, minutes example 1c example 7
0 0 0
10 8.3
20
30 20.3 44.1
45 69.2
60 85.0
80
90 48.5 95.6
120 64.4 98.5
150 78.0
180 87.7
240 94.6

Claims

1. A solid composition in the form of capsules or tablets containing a swelling pharmaceutically active compound, characterized in that it also contains a monosaccharide, disaccharide or oligosaccharide or an alcohol thereof.
2. A composition, according to the previous claim, containing a mono¬ saccharide or disaccharide.
3. A composition, according to any one of the preceding claims, containing a monosaccharide or an alcohol thereof.
4. A composition, according to the previous claim, characterized in that the monosaccharide or an alcohol thereof is sorbitol, mannitol, xylitol, lactitol, maltitol or dextrose, preferably sorbitol.
5. A composition, according to any one of the Claim 1 and 2, containing a disaccharide or an alcohol thereof.
6. A composition, according to the previous claim, characterized in that the disaccharide or an alcohol thereof is sucrose, fructose or lactose, preferably sucrose.
7. A composition, according to any one of the previous claims, character¬ ized in that the swelling pharmaceutically active compound is haemoglobin, Ginko Biloba extracts or a glycosaminglycane, preferably haemoglobin.
8. A composition, according to any one of the previous claims, character¬ ized in that the content of monosaccharide, disaccharide or oligosaccharide is in the range from about 5 % through about 50 %, preferably in the range from about 10 % to about 40 % (weight/weight).
9. A composition, according to any one of the previous claims, character- ized in that the content of swelling pharmaceutically active compound is in the range from about 30 % through about 90 % (weight/weight), preferably in the range from about 50 % to about 75 %.
10. Any novel feature or combination of features described herein.
PCT/DK1994/000338 1993-09-15 1994-09-13 Compositions containing swelling pharmaceuticals WO1995007689A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU76514/94A AU7651494A (en) 1993-09-15 1994-09-13 Compositions containing swelling pharmaceuticals

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DK1033/93 1993-09-15
DK103393A DK103393D0 (en) 1993-09-15 1993-09-15 PREPARATION

Publications (1)

Publication Number Publication Date
WO1995007689A1 true WO1995007689A1 (en) 1995-03-23

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DK (1) DK103393D0 (en)
WO (1) WO1995007689A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2780901A1 (en) * 1998-07-09 2000-01-14 Coletica PARTICLES, ESPECIALLY MICRO OR NANOPARTICLES OF MONOSACCHARIDES AND RETICULATED OLIGOSACCHARIDES, PROCESSES FOR THEIR PREPARATION AND COSMETIC, PHARMACEUTICAL OR FOOD COMPOSITIONS CONTAINING THEM

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4391797A (en) * 1977-01-05 1983-07-05 The Children's Hospital Medical Center Systems for the controlled release of macromolecules
EP0317079A2 (en) * 1987-11-19 1989-05-24 Orlando A. Battista High-fiber, expandable, dry-mixed compositions
EP0477061A1 (en) * 1990-09-07 1992-03-25 Pierre Fabre Medicament Tablet of Isosorbide-5-Mononitrate with sustained release and its process of preparation
WO1994004261A1 (en) * 1992-08-20 1994-03-03 Coletica Utilization of a transacylation reaction between an esterified polysaccharide and a polyaminated or polyhydroxylated substance for fabricating microparticles, microparticles thus obtained, methods and compositions containing them

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4391797A (en) * 1977-01-05 1983-07-05 The Children's Hospital Medical Center Systems for the controlled release of macromolecules
EP0317079A2 (en) * 1987-11-19 1989-05-24 Orlando A. Battista High-fiber, expandable, dry-mixed compositions
EP0477061A1 (en) * 1990-09-07 1992-03-25 Pierre Fabre Medicament Tablet of Isosorbide-5-Mononitrate with sustained release and its process of preparation
WO1994004261A1 (en) * 1992-08-20 1994-03-03 Coletica Utilization of a transacylation reaction between an esterified polysaccharide and a polyaminated or polyhydroxylated substance for fabricating microparticles, microparticles thus obtained, methods and compositions containing them

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2780901A1 (en) * 1998-07-09 2000-01-14 Coletica PARTICLES, ESPECIALLY MICRO OR NANOPARTICLES OF MONOSACCHARIDES AND RETICULATED OLIGOSACCHARIDES, PROCESSES FOR THEIR PREPARATION AND COSMETIC, PHARMACEUTICAL OR FOOD COMPOSITIONS CONTAINING THEM
US6197757B1 (en) 1998-07-09 2001-03-06 Coletica Particles, especially microparticles or nanoparticles, of crosslinked monosaccharides and oligosaccharides, processes for their preparation and cosmetic, pharmaceutical or food compositions in which they are present
ES2155793A1 (en) * 1998-07-09 2001-05-16 Coletica Particles, especially microparticles or nanoparticles, of crosslinked monosaccharides and oligosaccharides, processes for their preparation and cosmetic, pharmaceutical or food compositions in which they are present

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AU7651494A (en) 1995-04-03
DK103393D0 (en) 1993-09-15

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