NO326350B1 - Pharmaceutical composition containing lornoxicam and a disodium salt of EDTA - Google Patents
Pharmaceutical composition containing lornoxicam and a disodium salt of EDTA Download PDFInfo
- Publication number
- NO326350B1 NO326350B1 NO19990909A NO990909A NO326350B1 NO 326350 B1 NO326350 B1 NO 326350B1 NO 19990909 A NO19990909 A NO 19990909A NO 990909 A NO990909 A NO 990909A NO 326350 B1 NO326350 B1 NO 326350B1
- Authority
- NO
- Norway
- Prior art keywords
- edta
- lornoxicam
- pharmaceutical composition
- disodium salt
- solution
- Prior art date
Links
- OXROWJKCGCOJDO-JLHYYAGUSA-N lornoxicam Chemical compound O=C1C=2SC(Cl)=CC=2S(=O)(=O)N(C)\C1=C(\O)NC1=CC=CC=N1 OXROWJKCGCOJDO-JLHYYAGUSA-N 0.000 title claims abstract description 15
- 229960002202 lornoxicam Drugs 0.000 title claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 8
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 title claims 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 239000000243 solution Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 6
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012669 liquid formulation Substances 0.000 description 3
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- LXAHHHIGZXPRKQ-UHFFFAOYSA-N 5-fluoro-2-methylpyridine Chemical compound CC1=CC=C(F)C=N1 LXAHHHIGZXPRKQ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BHNLEKOHMPGJAH-UHFFFAOYSA-N 5-chloro-3-sulfinothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC(Cl)=CC=1S(O)=O BHNLEKOHMPGJAH-UHFFFAOYSA-N 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000004550 Postoperative Pain Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- VEUACKUBDLVUAC-UHFFFAOYSA-N [Na].[Ca] Chemical compound [Na].[Ca] VEUACKUBDLVUAC-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WLHQHAUOOXYABV-UHFFFAOYSA-N lornoxicam Chemical compound OC=1C=2SC(Cl)=CC=2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 WLHQHAUOOXYABV-UHFFFAOYSA-N 0.000 description 1
- 229910001437 manganese ion Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical group OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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]
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
Abstract
Description
Foreliggende oppfinnelse vedrører en klar farmasøytisk sammensetning til den parenterale eller oftalmiske administrering inneholdende 6-klor-4-hydroksy-2-metyl-N-2-pyridyl-2H-tieno-[2,3-e]-l,2-tiazin-karboksamid-l,l-dioksid (Lornoxicam) eller et farmasøytisk godtagbart salt herav. The present invention relates to a clear pharmaceutical composition for parenteral or ophthalmic administration containing 6-chloro-4-hydroxy-2-methyl-N-2-pyridyl-2H-thieno-[2,3-e]-1,2-thiazine- carboxamide-1,1-dioxide (Lornoxicam) or a pharmaceutically acceptable salt thereof.
Lornoxicam er et ikke-steroidalt antiinflammatorisk virkestoff og kan anvendes til behandlingen av akutte og kroniske tilstander, som opptrer sammen med betennelsesprosesser, f.eks. postoperative smerter, arthritis, reumatisme og lignende. Lornoxicam is a non-steroidal anti-inflammatory agent and can be used for the treatment of acute and chronic conditions, which appear together with inflammatory processes, e.g. post-operative pain, arthritis, rheumatism and the like.
Dcke-steroidale antiinflammatoriske virkestoffer (NSAIDS) er vanligvis tungt oppløselige, tildels nesten uløselige i vann. Denne uløselighet gir tungveiende problemer ved formuleringen av denne type forbindelser i løsninger til den parenterale eller oftalmiske administrering, spesielt til den intravenøse anvendelse. Økningen av løseligheten kan f.eks. foregå ved saltdannelse eller kompleksbinding av virkestoffet. Non-steroidal anti-inflammatory agents (NSAIDS) are usually poorly soluble, sometimes almost insoluble in water. This insolubility causes serious problems in the formulation of this type of compounds in solutions for parenteral or ophthalmic administration, especially for intravenous use. The increase in solubility can e.g. take place by salt formation or complex binding of the active substance.
Lornoxicam er et ytterst tungt oppløselig NSAID, som ytterligere er ustabil i flytende formulering, hvorved der ved oksidasjon og hydrolytisk spaltning dannes tallrike biprodukter. Stabiliteten av den flytende formulering kan økes ved lyofilisering, men den av lyofilisatet oppnådde flytende formulering utviser en ikke-uvesentlig turbiditet. Derved er de således fremstilte parenterale eller oftalmiske formuleringer ikke brukbare. Lornoxicam is an extremely poorly soluble NSAID, which is further unstable in liquid formulation, whereby numerous by-products are formed upon oxidation and hydrolytic cleavage. The stability of the liquid formulation can be increased by lyophilization, but the liquid formulation obtained from the lyophilisate exhibits a non-insignificant turbidity. As a result, the parenteral or ophthalmic formulations produced in this way are not usable.
Anvendelsen av EDTA og dennes salter til stabilisering av løsninger av farmasøytisk egnede forbindelser er velkjent. De blir spesielt anvendt til kompleks binding av metallioner, som kobber-, jem-, manganionet, som utløser oksidasjonen av det farmasøytiske virkestoffet eller øker dets hastighet. The use of EDTA and its salts for stabilizing solutions of pharmaceutically suitable compounds is well known. They are particularly used for the complex binding of metal ions, such as the copper, iron and manganese ions, which trigger the oxidation of the pharmaceutical active substance or increase its rate.
US5362758 beskriver en flytende sammensetning piroxicam, borsyre og natriumborat. Sammensetningen kan videre omfatte natrium EDTA, virkningen av natrium EDTA er ikke nærmere presisert. US5362758 describes a liquid composition of piroxicam, boric acid and sodium borate. The composition may further include sodium EDTA, the effect of sodium EDTA is not specified in more detail.
På overraskende vis ble det nå funnet at tilsetningen av en liten mengde av dinatriumsaltet av EDTA forhindrer tubiditeten av løsningen av lyofilisert lornoxicam. Denne effekt opptrer uten å ha en påvirkning av den kjemiske stabilitet av virkestoffet overfor oksidasjonsreaksjonen, hvilket ble vist ved en sammenlignings-stabilitetsundersøkelse over 3 år på lornoxicam-lyofilisatformuleringer med og uten dinatrium-EDTA. Surprisingly, it was now found that the addition of a small amount of the disodium salt of EDTA prevents the tubidity of the solution of lyophilized lornoxicam. This effect occurs without affecting the chemical stability of the active substance towards the oxidation reaction, which was shown by a comparative stability study over 3 years on lornoxicam lyophilisate formulations with and without disodium EDTA.
I motsetning til dinatriumsaltet av EDTA viser kalsiumnatirumsaltet av EDTA ingen påvirkning av turbiditeten av lornoxicam-formuleringen. In contrast to the disodium salt of EDTA, the calcium sodium salt of EDTA shows no influence on the turbidity of the lornoxicam formulation.
Gjenstand for foreliggende oppfinnelse er derfor farmasøytiske sammensetninger til den parenterale eller oftalmiske administrering omfattende lornoxicam eller et farmasøytisk godtagbart salt derav og et dinatriumsalt av EDTA. The object of the present invention is therefore pharmaceutical compositions for parenteral or ophthalmic administration comprising lornoxicam or a pharmaceutically acceptable salt thereof and a disodium salt of EDTA.
Ifølge foreliggende oppfinnelse blir dinatriumsaltet av EDTA anvendt til å hindre at det opptrer turbiditet i løsningen, av det lyofiliserte lornoxicam. According to the present invention, the disodium salt of EDTA is used to prevent turbidity from occurring in the solution of the lyophilized lornoxicam.
Andre metoder, som f.eks. filtrering av løsningen, tilsetning av askorbinsyre eller natriumbisulfitt eller tilsetning av en kompleksdanner som polyvidon 17 PF kunne ikke forhindre turbiditeten av løsningen. Other methods, such as filtering the solution, adding ascorbic acid or sodium bisulfite or adding a complexing agent such as polyvidon 17 PF could not prevent the turbidity of the solution.
Løsning i et organisk løsemiddel eller blandinger av disse, som f.eks. propylenglykol, polyetylenglykol og lignende reduserer godt nok turbiditeten av løsningen, men kommer på grunn av de ved injeksjonen av slike løsninger opptredende smerter gjennom hyperosmolaritet ikke i betraktning. Solution in an organic solvent or mixtures thereof, such as e.g. propylene glycol, polyethylene glycol and the like reduce the turbidity of the solution well enough, but due to the pain caused by the injection of such solutions due to hyperosmolarity is not taken into account.
Dinatriumsaltet av EDTA blir dessuten kun tilsatt i en særdeles liten mengde, omkring 0,1-5 mg pr. ml løsning, fortrinnsvis 0,25-4 mg pr. 10 ml løsning. The disodium salt of EDTA is also only added in an extremely small amount, around 0.1-5 mg per ml solution, preferably 0.25-4 mg per 10 ml solution.
De således fremstilte løsninger utviser turbiditetsverdier fra 3-12 og kan derfor klassifiseres som klare løsninger etter Ph.Eur. og er egnede til den parenterale og oftalmiske administrering. The solutions prepared in this way show turbidity values from 3-12 and can therefore be classified as clear solutions according to Ph.Eur. and are suitable for parenteral and ophthalmic administration.
Eksempel 1 Example 1
Klarheten av løsningen ble bestemt på følgende måte: The clarity of the solution was determined as follows:
a) Ph.Eur.-fremgangsmåte a) Ph.Eur. procedure
Prøven blir i diffust dagslys sammenlignet med vann eller et annet referansemiddel opp mot en sort bakgrunn. The sample is compared in diffused daylight with water or another reference medium against a black background.
b) Turbiditetsmåling b) Turbidity measurement
Prøven måles med en monokromatisk lysstråle med en bølgelengde på 564 nm, hvor en The sample is measured with a monochromatic light beam with a wavelength of 564 nm, where a
glasskuvette med standardisert turbiditet tjener som referanse. glass cuvette with standardized turbidity serves as a reference.
Standardformuleringen i rekonstituert løsning utviste turbiditetsverdier mellom 140 og 200, mens kun løsninger, som har turbiditetsverdier under 70-100 etter Ph.Eur. kan klassifiseres som klare. The standard formulation in reconstituted solution showed turbidity values between 140 and 200, while only solutions, which have turbidity values below 70-100 according to Ph.Eur. can be classified as clear.
Eksempel 2 Example 2
Løsningene av denne type av lornoxicamlyofilisat-resept utviste turbiditetsverdier på 3-12 i den rekonstituerte løsning. The solutions of this type of lornoxicam lyophilizate prescription exhibited turbidity values of 3-12 in the reconstituted solution.
Eksempel 3 Example 3
Løsningene av denne type av lornoxicamlyofilisat-resept utviste turbiditetsverdier på 160-340 i den rekonstituerte løsning. The solutions of this type of lornoxicam lyophilizate prescription exhibited turbidity values of 160-340 in the reconstituted solution.
Eksempel 4: Example 4:
Sammenlignelige stabilitetsdata etter 36 måneders lagring med lornoxicamlyofilisat-formuleringer fremstilt etter grunnresepten i eksempel 1 (uten EDTA-dinatrium) og eksempel 2 (med EDTA-dinatrium). Comparable stability data after 36 months of storage with lornoxicam lyophilizate formulations prepared according to the basic recipe in Example 1 (without EDTA disodium) and Example 2 (with EDTA disodium).
Forbindelse A: N-(2-aminopyridyl)oksalsyre Compound A: N-(2-aminopyridyl)oxalic acid
Forbindelse B: 5-klor-3-sulfinotiofen-2-karboksylsyre Compound B: 5-chloro-3-sulfinothiophene-2-carboxylic acid
Claims (4)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0156496A ATA156496A (en) | 1996-09-03 | 1996-09-03 | PHARMACEUTICAL COMPOSITION |
| PCT/EP1997/004742 WO1998009654A1 (en) | 1996-09-03 | 1997-09-01 | Pharmaceutical composition containing lornoxicam and a disodic salt of edta |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO990909D0 NO990909D0 (en) | 1999-02-25 |
| NO990909L NO990909L (en) | 1999-02-25 |
| NO326350B1 true NO326350B1 (en) | 2008-11-17 |
Family
ID=3516134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19990909A NO326350B1 (en) | 1996-09-03 | 1999-02-25 | Pharmaceutical composition containing lornoxicam and a disodium salt of EDTA |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0934079B1 (en) |
| JP (1) | JP4122062B2 (en) |
| CN (1) | CN1108822C (en) |
| AT (2) | ATA156496A (en) |
| AU (1) | AU4552597A (en) |
| CA (1) | CA2264626C (en) |
| DE (1) | DE59706450D1 (en) |
| DK (1) | DK0934079T3 (en) |
| ES (1) | ES2172002T3 (en) |
| NO (1) | NO326350B1 (en) |
| PT (1) | PT934079E (en) |
| WO (1) | WO1998009654A1 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001172183A (en) * | 1999-12-21 | 2001-06-26 | Wakamoto Pharmaceut Co Ltd | Ophthalmic pharmaceutical composition |
| DE10030345A1 (en) * | 2000-06-20 | 2002-01-10 | Boehringer Ingelheim Vetmed | Highly concentrated stable meloxicam solutions |
| US20020035107A1 (en) | 2000-06-20 | 2002-03-21 | Stefan Henke | Highly concentrated stable meloxicam solutions |
| DE10161077A1 (en) * | 2001-12-12 | 2003-06-18 | Boehringer Ingelheim Vetmed | Highly concentrated stable meloxicam solutions for needleless injection |
| US8992980B2 (en) | 2002-10-25 | 2015-03-31 | Boehringer Ingelheim Vetmedica Gmbh | Water-soluble meloxicam granules |
| JO2735B1 (en) | 2003-01-30 | 2013-09-15 | هيلسين هيلث كير أس ايه. | Liquid pharmaceutical formulations of palonosetron |
| EP1568369A1 (en) | 2004-02-23 | 2005-08-31 | Boehringer Ingelheim Vetmedica Gmbh | Use of meloxicam for the treatment of respiratory diseases in pigs |
| WO2011046853A1 (en) | 2009-10-12 | 2011-04-21 | Boehringer Ingelheim Vetmedica Gmbh | Containers for compositions comprising meloxicam |
| AU2010347598B2 (en) | 2010-03-03 | 2014-11-27 | Boehringer Ingelheim Vetmedica Gmbh | Use of meloxicam for the long-term treatment of musculoskeletal disorders in cats |
| US9795568B2 (en) | 2010-05-05 | 2017-10-24 | Boehringer Ingelheim Vetmedica Gmbh | Low concentration meloxicam tablets |
| WO2012127496A1 (en) | 2011-03-01 | 2012-09-27 | Cadila Healthcare Limited | Stable pharmaceutical compositions of lornoxicam or salts thereof |
| CN106727364B (en) * | 2016-12-02 | 2020-01-24 | 苏州天马医药集团天吉生物制药有限公司 | Freeze-drying process of lornoxicam for injection |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1203703B (en) * | 1983-05-23 | 1989-02-15 | Bruschettin Srl | Storage stable antiinflammatory eye drops |
| US5362758A (en) * | 1992-09-18 | 1994-11-08 | Pfizer Inc. | Ophthalmic piroxicam solution |
| WO1996041646A2 (en) * | 1995-06-13 | 1996-12-27 | Dyer, Alison, Margaret | Pharmaceutical compositions containing lornoxicam and cyclodextrin |
-
1996
- 1996-09-03 AT AT0156496A patent/ATA156496A/en not_active Application Discontinuation
-
1997
- 1997-09-01 WO PCT/EP1997/004742 patent/WO1998009654A1/en active IP Right Grant
- 1997-09-01 CA CA002264626A patent/CA2264626C/en not_active Expired - Lifetime
- 1997-09-01 PT PT97943820T patent/PT934079E/en unknown
- 1997-09-01 DE DE59706450T patent/DE59706450D1/en not_active Expired - Lifetime
- 1997-09-01 CN CN97197619A patent/CN1108822C/en not_active Expired - Lifetime
- 1997-09-01 JP JP51222198A patent/JP4122062B2/en not_active Expired - Lifetime
- 1997-09-01 AU AU45525/97A patent/AU4552597A/en not_active Abandoned
- 1997-09-01 DK DK97943820T patent/DK0934079T3/en active
- 1997-09-01 ES ES97943820T patent/ES2172002T3/en not_active Expired - Lifetime
- 1997-09-01 AT AT97943820T patent/ATE213420T1/en active
- 1997-09-01 EP EP97943820A patent/EP0934079B1/en not_active Expired - Lifetime
-
1999
- 1999-02-25 NO NO19990909A patent/NO326350B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP4122062B2 (en) | 2008-07-23 |
| ATA156496A (en) | 1997-10-15 |
| ATE213420T1 (en) | 2002-03-15 |
| EP0934079B1 (en) | 2002-02-20 |
| DK0934079T3 (en) | 2002-04-02 |
| NO990909D0 (en) | 1999-02-25 |
| PT934079E (en) | 2002-06-28 |
| NO990909L (en) | 1999-02-25 |
| CA2264626C (en) | 2009-03-24 |
| CN1108822C (en) | 2003-05-21 |
| JP2000517331A (en) | 2000-12-26 |
| CA2264626A1 (en) | 1998-03-12 |
| ES2172002T3 (en) | 2002-09-16 |
| AU4552597A (en) | 1998-03-26 |
| CN1228710A (en) | 1999-09-15 |
| DE59706450D1 (en) | 2002-03-28 |
| WO1998009654A1 (en) | 1998-03-12 |
| EP0934079A1 (en) | 1999-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: TAKEDA PHARMA A/S, DK |
|
| MK1K | Patent expired |