WO2000025750A1 - Compositions de metamizole a liberation prolongee - Google Patents
Compositions de metamizole a liberation prolongee Download PDFInfo
- Publication number
- WO2000025750A1 WO2000025750A1 PCT/EP1999/008120 EP9908120W WO0025750A1 WO 2000025750 A1 WO2000025750 A1 WO 2000025750A1 EP 9908120 W EP9908120 W EP 9908120W WO 0025750 A1 WO0025750 A1 WO 0025750A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- controlled
- metamizole
- release tablets
- fatty
- tablets according
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 238000013270 controlled release Methods 0.000 title claims abstract description 18
- 229940120889 dipyrone Drugs 0.000 title claims description 34
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 title claims description 18
- 238000009472 formulation Methods 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 11
- 239000004480 active ingredient Substances 0.000 claims abstract description 10
- 229920001477 hydrophilic polymer Polymers 0.000 claims abstract description 7
- 238000007909 melt granulation Methods 0.000 claims abstract description 7
- 239000008187 granular material Substances 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 claims description 18
- 229940049654 glyceryl behenate Drugs 0.000 claims description 18
- -1 fatty acid compound Chemical class 0.000 claims description 17
- 239000011734 sodium Substances 0.000 claims description 17
- 229910052708 sodium Inorganic materials 0.000 claims description 17
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 14
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 14
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 5
- 229920002126 Acrylic acid copolymer Polymers 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 229920002125 Sokalan® Polymers 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- 150000002433 hydrophilic molecules Chemical class 0.000 claims description 2
- 150000004668 long chain fatty acids Chemical class 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 239000001993 wax Substances 0.000 claims description 2
- 229920003086 cellulose ether Polymers 0.000 claims 1
- 238000000227 grinding Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 27
- 235000019359 magnesium stearate Nutrition 0.000 description 13
- 239000000454 talc Substances 0.000 description 12
- 229910052623 talc Inorganic materials 0.000 description 12
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000008119 colloidal silica Substances 0.000 description 11
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 11
- 239000008108 microcrystalline cellulose Substances 0.000 description 11
- 229940016286 microcrystalline cellulose Drugs 0.000 description 11
- 238000000338 in vitro Methods 0.000 description 10
- 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 2
- 230000000202 analgesic effect Effects 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 235000019759 Maize starch Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- DWNWZFAKFWMPTI-UHFFFAOYSA-N methanesulfonic acid;sodium Chemical compound [Na].CS(O)(=O)=O DWNWZFAKFWMPTI-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 239000008184 oral solid dosage form Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
-
- 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
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Definitions
- Metamizole or [2 , 3-dihydro-l , 5 -dimethyl -3 -oxo-2- phenyl-lH-pyrazol-4-yl) -methylamino] methane sulfonic acid sodium or magnesium salt is an orally active analgesic .
- Metamizole has been commercially available for a long time in the form of conventional pharmaceutical compositions such as tablets, drops, suppositories and the like, as an analgesic and antipyretic. Controlled- release formulations of metamizole have never been disclosed.
- the present invention provides therefore controlled release tablets comprising: a) metamizole, or its pharmaceutically acceptable salt as the active ingredient, coated by a fatty compound ; b) an hydrophilic water swellable polymer; c) suitable excipients.
- the fatty compound consists of hydrophobic high molecular weight compounds, preferably waxes, triglycerides of long chain fatty acids, vegetable or mineral oils, fatty acids, high molecular weight alcohols or glycols, esters and ethers thereof. It is preferred the use of compounds having a melting point ranging from at least 30 to 150°C. Glyceryl behenate is particularly preferred.
- suitable hydrophilic polymers include polyethylenglycols, alginates, cellulose and its derivatives (ethers, esters, salts) , acrylic acid polymers or co-polymers. Hydroxypropylcellulose is particularly preferred. Conventional excipients, commonly used in the preparation of oral solid dosage forms, can be added to the compositions of the invention.
- excipients include lubricants, diluents, disgregating agents, colouring agents, etc.
- Each tablet will typically contain from 200 to 1500 mg of active ingredient.
- the percentage of the fatty compound in the mixture with metamizole will range from about 2 to about 40% by weight, preferably from about 5 to 15%.
- the percentage of the hydrophilic polymer ranges from 5 to 50% of the weight of the active ingredient, preferably from 10 to 40%.
- the invention also relates to multi-layer tablets, preferably double-layer tablets, in which one of the layers has a controlled release and one of the others has an immediate release.
- compositions of the invention may be prepared by a process comprising: a) subjecting metamizole and the fatty compound to melt granulation; b) mixing the granulate obtained in a) with an hydrophilic compound and suitable excipients; c) tabletting the mixture obtained in b) .
- the melt granulation step is carried out by heating the mixture to the melting point of the fatty compound in a fluid bed, a static oven or a conventional granulating apparatus.
- the tablets may be film-coated in order to provide taste-masking or a further enhancement of the release characteristics .
- the release characteristics of the composition may be changed by adjusting the ratio of the fatty compound to the hydrophilic polymer.
- the in vitro release may range, for instance, from 6-8 up to 24 hours.
- compositions of the invention may be accordingly administered twice or even once a day, according to the desired therapeutic needs.
- compositions of the invention are moreover characterized by a remarkable stability, possibly in view of the protective effect the fatty compound exerts on the water-instable active ingredient.
- each tablet contains:
- a melt granulation process is carried out with a high speed granulator mixing Metamizole and glyceryl behenate.
- the obtained granulate is mixed thereafter with the other excipients and tabletted.
- the in vitro release profile is shown. The test was carried out in water, 1000 ml, stirring speed 50 rpm, 37°C, UV detection at 300 nm.
- each tablet contains:
- each tablet contains :
- each tablet contains: Sodium Metamizole Monohydrate mg 1000. ,0 Cetyl alcohol mg 80. ,0
- each tablet contains:
- each tablet contains:
- each tablet contains:
- Example 8 each tablet contains: Sodium Metamizole Monohydrate mg 1000.0
- each tablet contains:
- Acrylic Acid Co-polymers mg 120.0 The preparation method and the determination of the in vitro release were carried out as in Example 1.
- each tablet contains:
- Microcrystalline Cellulose mg 40 . 0 Colloidal Silica mg 6 , . 5
- each tablet contains:
- each tablet contains:
- Example 11 The preparation method of Example 11 was followed, using a first tabletting step followed by sieving and then by a second tabletting step. The amount of magnesium stearate is portioned into two equal parts. Time (hours) (%) Released
- each tablet contains: Sodium Metamizole Monohydrate mg 1000 . . 0
- Example 14 each tablet contains:
- Titanium bioxide mg 2 .0 The melt granulation process is carried out with a high speed granulator mixing Metamizole and glyceryl behenate. The obtained granulate is mixed thereafter with the other excipients and tabletted.
- the film composition is the one referred to as the coating, the aim being masking the taste without changing the release profile .
- each tablet contains:
- the melt granulation process is carried out with a high speed granulator mixing Metamizole and glyceryl behenate. The obtained granulate is mixed thereafter with the other excipients and tabletted.
- Magnesium stearate mg 2.0 Metamizole is mixed with the other excipients.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Compositions solides à libération prolongée pour administration orale, obtenues en soumettant le principe actif et un composé gras à la granulation par fusion, puis en mélangeant le granulat obtenu avec un polymère hydrophile et des excipients classiques.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU11550/00A AU1155000A (en) | 1998-11-03 | 1999-10-27 | Controlled-release formulations of metamizole |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI98A002365 | 1998-11-03 | ||
| IT1998MI002365A IT1303693B1 (it) | 1998-11-03 | 1998-11-03 | Composizioni a rilascio controllato di metamizolo. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2000025750A1 true WO2000025750A1 (fr) | 2000-05-11 |
Family
ID=11380995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1999/008120 WO2000025750A1 (fr) | 1998-11-03 | 1999-10-27 | Compositions de metamizole a liberation prolongee |
Country Status (6)
| Country | Link |
|---|---|
| AR (1) | AR020998A1 (fr) |
| AU (1) | AU1155000A (fr) |
| CO (1) | CO5160319A1 (fr) |
| IT (1) | IT1303693B1 (fr) |
| PE (1) | PE20001231A1 (fr) |
| WO (1) | WO2000025750A1 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000066088A1 (fr) * | 1999-05-04 | 2000-11-09 | Hexal Ag | Composition pharmaceutique a liberation controlee contenant du metamizol |
| US20110046072A1 (en) * | 2008-05-07 | 2011-02-24 | Bayer Animal Health Gmbh | Solid pharmaceutical formulation with delayed release |
| WO2018087109A1 (fr) | 2016-11-08 | 2018-05-17 | Grünenthal GmbH | Forme galénique multiparticulaire à libération de métamizole contrôlée |
| US10682337B2 (en) * | 2015-03-03 | 2020-06-16 | Kindred Biosciences, Inc. | Compositions and methods for treatment and prevention of pyrexia in horses |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998047534A1 (fr) * | 1997-04-18 | 1998-10-29 | Klinge Pharma Gmbh | Medicaments stabilises renfermant des derives cysteinyle |
-
1998
- 1998-11-03 IT IT1998MI002365A patent/IT1303693B1/it active
-
1999
- 1999-10-27 AU AU11550/00A patent/AU1155000A/en not_active Abandoned
- 1999-10-27 WO PCT/EP1999/008120 patent/WO2000025750A1/fr active Application Filing
- 1999-10-28 AR ARP990105435A patent/AR020998A1/es unknown
- 1999-10-29 CO CO99068639A patent/CO5160319A1/es unknown
- 1999-11-03 PE PE1999001101A patent/PE20001231A1/es not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998047534A1 (fr) * | 1997-04-18 | 1998-10-29 | Klinge Pharma Gmbh | Medicaments stabilises renfermant des derives cysteinyle |
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 91, no. 10, 3 September 1979, Columbus, Ohio, US; abstract no. 78844, XP002110962 * |
| L.V.N.PRISTA ET AL.: "COMPRESSED DIPYRONE TABLETS WITH PROLONGED ACTION", AN. FAC. FARM. UNIV. FED. PERNAMBUCO (BR), vol. 15, 1976, pages 57 - 68 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000066088A1 (fr) * | 1999-05-04 | 2000-11-09 | Hexal Ag | Composition pharmaceutique a liberation controlee contenant du metamizol |
| US20110046072A1 (en) * | 2008-05-07 | 2011-02-24 | Bayer Animal Health Gmbh | Solid pharmaceutical formulation with delayed release |
| US10682337B2 (en) * | 2015-03-03 | 2020-06-16 | Kindred Biosciences, Inc. | Compositions and methods for treatment and prevention of pyrexia in horses |
| WO2018087109A1 (fr) | 2016-11-08 | 2018-05-17 | Grünenthal GmbH | Forme galénique multiparticulaire à libération de métamizole contrôlée |
Also Published As
| Publication number | Publication date |
|---|---|
| AR020998A1 (es) | 2002-06-05 |
| ITMI982365A1 (it) | 2000-05-03 |
| AU1155000A (en) | 2000-05-22 |
| PE20001231A1 (es) | 2000-11-29 |
| CO5160319A1 (es) | 2002-05-30 |
| IT1303693B1 (it) | 2001-02-23 |
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