GB2175307A - Crosslinked dextran grain polymers and therapeutical compositions - Google Patents
Crosslinked dextran grain polymers and therapeutical compositions Download PDFInfo
- Publication number
- GB2175307A GB2175307A GB08612257A GB8612257A GB2175307A GB 2175307 A GB2175307 A GB 2175307A GB 08612257 A GB08612257 A GB 08612257A GB 8612257 A GB8612257 A GB 8612257A GB 2175307 A GB2175307 A GB 2175307A
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- United Kingdom
- Prior art keywords
- water
- polymer
- grain
- grains
- classifying
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- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 title claims abstract description 15
- 229920002307 Dextran Polymers 0.000 title claims abstract description 14
- 230000001225 therapeutic effect Effects 0.000 title description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 206010052428 Wound Diseases 0.000 claims abstract description 18
- 239000002245 particle Substances 0.000 claims abstract description 9
- 239000000843 powder Substances 0.000 claims abstract description 7
- 230000008961 swelling Effects 0.000 claims abstract description 7
- 230000002378 acidificating effect Effects 0.000 claims abstract description 5
- 230000001954 sterilising effect Effects 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 5
- 238000004659 sterilization and disinfection Methods 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 238000001035 drying Methods 0.000 claims abstract 2
- 208000027418 Wounds and injury Diseases 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000010410 dusting Methods 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000006228 supernatant Substances 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 229920002689 polyvinyl acetate Polymers 0.000 description 5
- 239000011118 polyvinyl acetate Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 230000035876 healing Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000282898 Sus scrofa Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-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
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 235000003805 Musa ABB Group Nutrition 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000015266 Plantago major Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000005030 aluminium foil Substances 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 231100000732 tissue residue Toxicity 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0021—Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0023—Polysaccharides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Materials For Medical Uses (AREA)
- Prostheses (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
A process for preparing therapeutically useful, crosslinked dextran grain polymers and the compositions containing them comprises swelling the crosslinked grain polymer in water at a pH of 1.0 to 5.5, suitably at a pH value of 4.0, while stirring, removing the acidic water and dehydrating by using a water-miscible organic solvent, preferably ethanol, removing the supernatant while stirring, swelling the dehydrated grain polymer in ion-free water, washing it until acid-free, dehydrating and/or drying it, classifying it according to the particle size and formulating it in the form of e.g. a powder, plug or paste, optionally after a sterilization with gamma irradiation. The product is useful for treating, by covering, open wounds.
Description
SPECIFICATION
A process for the preparation of therapeutically useful, crosslinked dextran grain polymers and therapeutical compositions containing them
The invention relates two an improved process for preparing therapeutically useful dextran grain polymers and the therapeutical compositions containing them.
According to the process of the invention, the crosslinked grain polymer is swollen in water at a pH of I .5to 5.5, suitably at a pH of 4.0 and after removing the acidic water, it is treated with a water-miscible organic solvent, suitably with ethanol.
After removing the aqueous ethanolic phase, the thus dehydrated grain polymer is again swollen in ion-free water, washed until free from acid, dried and formulated suitably after sterilizing by irradiation with gamma-rays into a therapeutically useful form.
It is known that water-absorbing methods (use of halved tomato, or plantain leavesforcovering wounds) have been used in the popular medicinefor healing succulent, infected, purulentwounds.
Althoug h these therapeutica I methods were based on experience, their success could be attributed to that the open wounds were purified from the tissue fluids and nectrotized tissue residues, thereby the possibility offixation and propagation of microorganisms on the wound surfaces was decreased and, on the other hand, the wounds were protected from the harmful effect of the metabolic products and toxins of the microorganisms; further on, the airsupplyofthewoundswas improved and an appropriate water-absorbing effect was achieved by covering the wounds with the above-mentioned materials of natural origin.When this water-absorbing effect has also been extended to the edematic parts of the wounds, than a better blood supply could be provided in the environment of the wounds, whereby the restoration of the tissues was also made possible.
The compositon according to the UK-PS No.
1,454,055 of Pharmacia AB, a Swedish company (known as DebrisanR in the commerce), completely satisfies the physical and chemical conditions of an optimum wound-healing. In this patent specification, the authors referto processes reported in their previous patent specifications for preparing the dextran gel representing the active ingredient ofthe composition (UK-PS Nos. 845,715,936,039,974,054 and 1,013,585).
It has been observed in the course of our experiments that the dextran grain polymer (prepared as described in Example 1 of the U K-PS No.
974,054), when crosslinked with epichlorohydrin in an alkaline solution by using polyvinyl acetate as a suspension stabilizing agent, did not possess in animal experiments the therapeutic effect indicated in the UK-PS No. 1,454,055, though its water regain (water-absorbing capacity) and particle size corresopnded to the data given in the last-mentioned patent specification.The pharmacologicai properties of the grain polymers prepared according to the
Examples 2,3,4 and 5 ofthe UK-PS No. 974,054were also investigated by the result expected could not be achieved even by these preparations (As compared to
Example 1, said Examples are only different concerning the suspension medium: toluene is used in Example 1, 0-dichlorobenzene in Example 2, dichloromethane in Example 3, dibromomoethane in
Example 4 and 1 ,2-dichloroethane in Example 5.) During animal experiments, KAHIB (a Hungarian breed) swines of both sexes with a body-weight of 8 to 12 kg. were used.Burns of 20 mm. in dimeterwere evoked on both sides ofthe animals by using the end of a copper rod heated to 170 to 180"C, under anaesthesia induced by 35 mg./kg. Evipan [sodium 5-(1-cyclohexen-1 -yl)-1 5-dimethylbarbiturate] administered intravenously [according to the method of S. Jacobson et al.: Scand. J. Plast. Reconstr. Surg.
10,97-101(1976).
Six animals each were used in both the experimental and control groups. The observation period lasted 14 days.
After injuring the animals, the infected wounds were treated beginning from the 3rd day with the grain polymer prepared as described in Example 1 of the UK-PS No.974,054 (which was reproduced as described in Example 1 ofthis invention) orwith the commercially available DebrisanR.Thewound in one side of the swines was treated with DebrisanR, whereas the wound in the other side was treated with the grain polymer prepared as described in the UK-PS No. 974,054. Thetreatmentwas carried out once a day.
ltcould be stated in the course of these experiments that, although the tissue fluids were absorbed and the bacteria aswell astissuedebris were removed and thus the wound was cleansed by the grain polymer prepared as described in Example 1 of the UK-PS No. 974,054, however, an undesired side-effect appeared which became very obvious on studying the histological samples: the wound and its environment became intensely edematic. Thus, although the wound was cleansed, the blood and oxygen supply were decreased as a consequence of the edema formation, whereby the healing was inhibited.
The use of the DebrisanR composition resulted in the expected effect: the wounds healed and the formation of an edema was not observed.
On the basis of our above investigations it was concluded that the grain polymer prepared as described in Example 1 ofthe UK-PS 974,054 may contain materials which have been occluded by the grains in the course ofthe manufacturing process whereby, after diffusion of these materials from the grains on the wound surface, an edema development by irritation occurred and the healing was retarded.
This hypothesiswassupported by microscopic investigation: the particles of the grain polymer prepared according to Example 1 ofthe UK-PS No.
974,054 were opalescent and opaque.
Surprisingly, itwas observed that the contaminating material could be removed from the grains by washing ata pH value of 1 to 5.5 and a following treatment with ethanol. After thins treatment, the grains were swollen in water, stirred with water until free from acid, made free from water
by using ethanol and dried to give clear, transparent
grains (prepared as described in ExampleS of thins invention) which gave the same advantageous
results in the animal experiments carried out as
reported above, as DebrisanR used as control.
The purification product can be formulated e.g. as wound powder in spreading boxes; as wound plug
closed in a filter; or in the form of a paste.
The process ofthe invention is illustrated in detail by the following non-limiting Examples.
Example I
Reproduction of Example 1 ofthe UK-PS No.974,054
Dextran with an average molecularweightof 40,000 was moistened with 20% ofwaterand 6N
aqueous sodium hydroxide solution was added to this mixture in order to adjust a final concentration of
40% ofthe solution. The thus-obtained dextran
solution weighing 600 g. was poured into a cylindrical
reaction bottle which had been fitted with a
thermometer and stirrer.The solution of polyvinyl
acetate with an average molecularweightof430,000
in 500 ml. oftolunewas portionwise added as a suspension-stabilizing agent,the stirring was started
and continued at such a rate thatthe aqueous phase was dispersed in the toluene phase in the form of littie droplets. then 50 g. of epichlorohydrin were
portionwise added while keeping thetemperature at 50"C. A gel was formed within 1 hour. After completion ofthe reaction, the gel grains were filtered out,thesuspension-stabilizing agentwas washed out bytoluene, then the toluene was
removed by washing with ethanol.Finally, the
product was washed with water until neutral and dried at 11000. The thus-obtained grains had a particle size of 30 to 100 ffi and a water regain of 3.0 g./g. of dry substance.
Example 2
100 g. of dry dextran grain polymer, crosslinked with epichlorohydrin, obtained as described in
Example 1,were swollen for4 hours in 100 ml. of water, the pH value of which had been adjusted to 4.
During the swelling the mixture was continuously and mildly stirred and the pH value was controlled.
Thereafter, the acidic liquid was discarded and the swelling was repeated by using 500 ml. ofwater adjusted to a pH value of 4 by adding hydrochloric acid while the mixture was mildly and continuously stirred for 1 hour. After discarding the acidic water, the swollen grains were stirred with 500 ml. of ethanol for 1 hour, the supernatant was discarded and the treatment with ethanol was repeated in the above manner. The dehydrated grains were swollen by using ion-free water, washed until reaching a pH value of 5.5 and after making the grains water4ree with 500 ml. of ethanol, the grain polymer was dried at80 C. The grain size and water regain ofthe thus-obtained grainswerethe same as described in
Example 1.
Example 3
100 g. of dry dextran grain polymer crosslinked with epichlorohydrin, obtained as described in
Example 1,were swollen for4 hours in 100 ml. of
water, then the pH was adjusted to 1 by adding
hydrochloric acid under continuous and mild stirring, whereafterthe Example 1 was followed.The water
regain and size of the thus-obtained grains were
identical to those described in Example 1.
Example 4 100 9. of dry dextran 9 rain polymer crosslinked
with epichlorohydrin, obtained as described in
Example 1, were swollen for4 hours in 2000 ml. of
water adjusted to pH 4 by adding hydrochloric acid.
During this swelling,the mixture was continuously
stirred and the pH value was controlled. Thereafter, the Example 1 was followed. The water regain and
size ofthe thus-obtained grains were identical to those described in Example 1.
Example 5
32 g. of polyvinyl acetate with an average molecular weig ht of 430,000 were dissolved in 380 ml. to toluene weight of 430,000 were dissolved in 380
ml. oftoluenewhilestirring at SO to 550C, then cooled to 20 "C. 100 g. of dextran powder with an average molecularweight of 40,000 were dissolved in 100 ml.
ofwaterand the solution of 24 g. of sodium hydroxide
in 27 ml. of water was added. The thus-obtained
mixture was stirred, then 42 ml. of epichlorohydrin and the above-prepared toluene solution ofthe
polyvinyl acetate were added and the reaction
mixture was stirred at 50 to 55 Cfor additional 16 hours. Thethus-formed grain polymerwaswashed with toluene until it became free from polyvinyl acetate, then washed with ethanol and water.
Thereafter, the grains were stirred for 1 hour in 500 mi, of wateradjusted to a pH value of 4 by adding hydrochloric acid. The washing with acid was repeated andthenthe processof Example 1 was followed. The thus-obtained grains had a particle size of 40to 100 wand awaterregain of 2.8g./g.ofdry substance.
Example 6
The final product obtained as described in Example 1 was classified according to the particle size. 60 g.
doses of the grains having a diameter of 100 to 350 A were filled into boxes and sterilized in unit packages while keeping a value of 20 keg./0.1 m3, by using a Co60 irradiation with a dose of 25 kGy.
Example 7
The final product obtained as described in Example 1 was classified according to the particle size. The grains having a diameter of 40 to 100 y were divided to amounts of 1 g. each between two layers of physiologically indifferent filter papers and the paper layers were welded together. The sterilization was carried out as described in Example 6.
Example 8
The final product obtained as described in Example 1 was classified according to the particle size. 6800 g.
of the grains having a diameter of 40 to 100 teach were suspended in a mixture of 2900 g. of polyoxethen-200 and 300 g. of sorboxethen monooleatefor30 minutes, then 10 g. doses ofthe thus-obtained paste each were placed into chartulas prepared from aluminium foil laminated with polyethylene, whereupon the charts lays were closed by welding. The sterilization was carried outas described in Example 5.
Claims (9)
1. Aprocessforthe preparation ofa therapeutically useful crosslinked dextran grain polymer and the composition containing it, which comprises swelling the crosslinked grain polymer in water at a pH value of 1 .Oto 5.5, suitably at a pH value of4.Owhile sti rri ng, removing the acidic water and dehydrating by using a water-miscible organic solvent, preferably ethanol, removing the supernatantwhile stirring, swelling the dehydrated grain polymer in ion-free water, washing it until acid-free, dehydrating and/or drying it, classifying it according to the particle size and formulating it in the form e.g. of a powder, plug or paste, optionallyaftera sterilization with gamma irradiation.
2. A process as claimed in claim 1,which comprises carrying outthewashingwith acid by using acidicwater in a 5to 20-fold volume calculated fortheweightofthegrain polymer.
3. A process as claimed in claim 1, which comprises formulating the grains having a diamter of 100to350 > obtained by classifying the dried grain polymer in a form of a dusting powder.
4. A process as claimed in claim 1 ,which comprises formulating the grains having a diamter of 40to 100 obtained byclassifyingthe dried grain polymerintheform of a plug closed between two physiologically indifferent filter papers.
5. A process as claimed in clam 1, which comprises formulating the grains having a diameter of 40 to 100 obtained by classifying the dried grain polymer in the form ofa paste suspended in a mixture of polyoxethene and sorboxethene monooleate.
6. A process as claimed in claim 1, substantially as hereinbefore described in any one of Examples 2 to 5.
7. Cross-linked dextran powder obtained by a process as claimed in any one of claims 1,2 and 6.
8. Atherapeutical composition or material for treating wounds comprising cross-linked dextran powders claimed in claim 7 optionallytogetherwith a pharmaceutically acceptable carrier.
9. Acomposition as claimed in claim 8, substantially as hereinbefore described in any one of
Examples 6to 8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MYPI87000439A MY101723A (en) | 1985-05-21 | 1987-04-04 | A process for the preparation of therapeutically useful, crosslinked dextran grain polymers and therapeutical compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU851913A HU193372B (en) | 1985-05-21 | 1985-05-21 | Process for the purification of a dextrane bead polymer of stereoscopic mesh structure suitable for pharmaceutical purposes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8612257D0 GB8612257D0 (en) | 1986-06-25 |
| GB2175307A true GB2175307A (en) | 1986-11-26 |
| GB2175307B GB2175307B (en) | 1988-10-12 |
Family
ID=10956825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08612257A Expired GB2175307B (en) | 1985-05-21 | 1986-05-20 | A process for the preparation of therapeutically useful, crosslinked dextran grain polymers and therapeutical compositions containing them |
Country Status (10)
| Country | Link |
|---|---|
| CN (1) | CN1017338B (en) |
| ES (1) | ES8707112A1 (en) |
| FI (1) | FI80052C (en) |
| GB (1) | GB2175307B (en) |
| GR (1) | GR861310B (en) |
| HU (1) | HU193372B (en) |
| IN (1) | IN166870B (en) |
| MY (1) | MY101723A (en) |
| SG (1) | SG71389G (en) |
| SU (1) | SU1496627A3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1025868A1 (en) * | 1999-02-08 | 2000-08-09 | HemArrest, Inc. | Topically applied clotting material |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1079374C (en) * | 1998-02-24 | 2002-02-20 | 广州市华昌科技开发有限公司 | Preparation of titanic-schorl type titanium white by hydrochloric -acid process |
| CN113304305A (en) * | 2021-04-27 | 2021-08-27 | 宁波绿糖生物科技有限公司 | Glucan microsphere and preparation method and application thereof |
-
1985
- 1985-05-21 HU HU851913A patent/HU193372B/en not_active IP Right Cessation
-
1986
- 1986-05-14 CN CN86103288.8A patent/CN1017338B/en not_active Expired
- 1986-05-20 GB GB08612257A patent/GB2175307B/en not_active Expired
- 1986-05-20 GR GR861310A patent/GR861310B/en unknown
- 1986-05-20 IN IN386/MAS/86A patent/IN166870B/en unknown
- 1986-05-20 FI FI862105A patent/FI80052C/en not_active IP Right Cessation
- 1986-05-21 SU SU864027554A patent/SU1496627A3/en active
- 1986-05-21 ES ES555189A patent/ES8707112A1/en not_active Expired
-
1987
- 1987-04-04 MY MYPI87000439A patent/MY101723A/en unknown
-
1989
- 1989-10-25 SG SG713/89A patent/SG71389G/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1025868A1 (en) * | 1999-02-08 | 2000-08-09 | HemArrest, Inc. | Topically applied clotting material |
Also Published As
| Publication number | Publication date |
|---|---|
| FI80052B (en) | 1989-12-29 |
| GB8612257D0 (en) | 1986-06-25 |
| CN86103288A (en) | 1986-12-17 |
| IN166870B (en) | 1990-07-28 |
| GR861310B (en) | 1986-09-16 |
| CN1017338B (en) | 1992-07-08 |
| SU1496627A3 (en) | 1989-07-23 |
| ES555189A0 (en) | 1987-07-16 |
| HUT40148A (en) | 1986-11-28 |
| SG71389G (en) | 1990-03-02 |
| GB2175307B (en) | 1988-10-12 |
| ES8707112A1 (en) | 1987-07-16 |
| FI80052C (en) | 1990-04-10 |
| FI862105A0 (en) | 1986-05-20 |
| FI862105A (en) | 1986-11-22 |
| MY101723A (en) | 1992-01-17 |
| HU193372B (en) | 1987-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930520 |