KR100869752B1 - 레보시멘단의 약학적 액제 - Google Patents
레보시멘단의 약학적 액제 Download PDFInfo
- Publication number
- KR100869752B1 KR100869752B1 KR20027002923A KR20027002923A KR100869752B1 KR 100869752 B1 KR100869752 B1 KR 100869752B1 KR 20027002923 A KR20027002923 A KR 20027002923A KR 20027002923 A KR20027002923 A KR 20027002923A KR 100869752 B1 KR100869752 B1 KR 100869752B1
- Authority
- KR
- South Korea
- Prior art keywords
- solution
- pharmaceutically acceptable
- acid
- liquid formulation
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003186 pharmaceutical solution Substances 0.000 title claims abstract description 4
- WHXMKTBCFHIYNQ-SECBINFHSA-N levosimendan Chemical compound C[C@@H]1CC(=O)NN=C1C1=CC=C(NN=C(C#N)C#N)C=C1 WHXMKTBCFHIYNQ-SECBINFHSA-N 0.000 title abstract description 3
- 229960000692 levosimendan Drugs 0.000 title abstract 2
- 239000000243 solution Substances 0.000 claims abstract description 36
- 238000001990 intravenous administration Methods 0.000 claims abstract description 28
- 238000001802 infusion Methods 0.000 claims abstract description 23
- 239000012141 concentrate Substances 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 150000007524 organic acids Chemical class 0.000 claims abstract description 11
- 239000004480 active ingredient Substances 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 33
- 239000012669 liquid formulation Substances 0.000 claims description 14
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 14
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 14
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000003978 infusion fluid Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 239000008137 solubility enhancer Substances 0.000 abstract description 15
- 239000000126 substance Substances 0.000 abstract description 13
- 238000001556 precipitation Methods 0.000 abstract description 6
- 239000000546 pharmaceutical excipient Substances 0.000 abstract description 5
- 230000007935 neutral effect Effects 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 238000003860 storage Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 206010019280 Heart failures Diseases 0.000 description 6
- 101150044039 PF12 gene Proteins 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000008364 bulk solution Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000010253 intravenous injection Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- -1 polyethylene glycol) Chemical compound 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000644 isotonic solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- WHXMKTBCFHIYNQ-UHFFFAOYSA-N 2-[[4-(4-methyl-6-oxo-4,5-dihydro-1h-pyridazin-3-yl)phenyl]hydrazinylidene]propanedinitrile Chemical compound CC1CC(=O)NN=C1C1=CC=C(NN=C(C#N)C#N)C=C1 WHXMKTBCFHIYNQ-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QKSZUHCKZRHCLW-UHFFFAOYSA-N CC(C1)C(c(cc2)ccc2NN=C(C)C)=NNC1=O Chemical compound CC(C1)C(c(cc2)ccc2NN=C(C)C)=NNC1=O QKSZUHCKZRHCLW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 230000002925 chemical effect Effects 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229940068939 glyceryl monolaurate Drugs 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 125000005638 hydrazono group Chemical group 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229960000502 poloxamer Drugs 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940076133 sodium carbonate monohydrate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI991925A FI109659B (fi) | 1999-09-10 | 1999-09-10 | Levosimendaanin farmaseuttisia liuoksia |
| FI19991925 | 1999-09-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20020048400A KR20020048400A (ko) | 2002-06-22 |
| KR100869752B1 true KR100869752B1 (ko) | 2008-11-21 |
Family
ID=8555263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR20027002923A Expired - Lifetime KR100869752B1 (ko) | 1999-09-10 | 2000-09-08 | 레보시멘단의 약학적 액제 |
Country Status (39)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI109659B (fi) * | 1999-09-10 | 2002-09-30 | Orion Yhtymae Oyj | Levosimendaanin farmaseuttisia liuoksia |
| FI20010233A0 (fi) * | 2001-02-08 | 2001-02-08 | Orion Corp | Menetelmä sydämen vajaatoiminnan hoitoon |
| CN100428937C (zh) * | 2003-10-30 | 2008-10-29 | 北京海合天科技开发有限公司 | 左西孟旦冷冻干燥组合物 |
| CN100367964C (zh) * | 2004-04-29 | 2008-02-13 | 王思清 | 左西孟旦-β环糊精包含物制剂 |
| US20070032557A1 (en) * | 2005-02-18 | 2007-02-08 | Matti Kivikko | Method for administering levosimendan |
| WO2008082871A1 (en) * | 2006-12-28 | 2008-07-10 | Orion Corporation | Formulations of levosimendan for parenteral administration |
| US10046081B2 (en) | 2008-04-11 | 2018-08-14 | The Henry M Jackson Foundation For The Advancement Of Military Medicine, Inc. | Electrospun dextran fibers and devices formed therefrom |
| WO2012093404A2 (en) | 2011-01-03 | 2012-07-12 | Gufic Biosciences Limited | Parenteral formulations of levosimendan |
| US8697118B2 (en) * | 2011-10-18 | 2014-04-15 | St. Teresa Medical, Inc. | Stabilizers for hemostatic products |
| CA2873502C (en) * | 2012-05-18 | 2017-09-12 | Luoda Pharma Pty Ltd | Liquid formulation |
| CN105106113B (zh) * | 2015-09-30 | 2019-07-26 | 济南康和医药科技有限公司 | 一种左西孟旦注射液及其制备方法 |
| ES2782106T3 (es) * | 2015-11-06 | 2020-09-10 | Carinopharm Gmbh | Formulaciones mejoradas de levosimendán para administración intravenosa como infusión o inyección y como concentrado de infusión |
| AU2016351557A1 (en) | 2015-11-12 | 2018-05-31 | St. Teresa Medical, Inc. | A method of sealing a durotomy |
| CN108261398A (zh) * | 2016-12-30 | 2018-07-10 | 齐鲁制药有限公司 | 一种含有左西孟旦的供注射用药物制剂及其制备方法 |
| US10953128B2 (en) | 2017-11-02 | 2021-03-23 | St. Teresa Medical, Inc. | Fibrin sealant products |
| CN111474289A (zh) * | 2019-10-31 | 2020-07-31 | 武汉嘉诺康医药技术有限公司 | 一种利用反相色谱分离分析左西孟旦中右西孟旦的方法 |
| EP4076398A4 (en) | 2019-12-16 | 2024-01-03 | Tenax Therapeutics, Inc. | LEVOSIMENDAN TO TREAT PULMONARY HYPERTENSION ACCOMPANIED BY HEART FAILURE BY MEANS OF PRESERVED EJECTION FRACTION (PH-HF-PEF) |
| CN111514147B (zh) * | 2020-05-12 | 2021-09-17 | 成都欣捷高新技术开发股份有限公司 | 用于急性失代偿心力衰竭症状的左西孟旦钠药用组合物及制备方法 |
| US11760730B2 (en) * | 2021-01-11 | 2023-09-19 | Navinta, Llc | Process for the preparation of high purity Levosimendan |
| WO2023027670A2 (en) * | 2021-08-23 | 2023-03-02 | Tum Ekip Ilac Anonim Sirketi | Lyophilized levosimendan compositions |
| CN115518037A (zh) * | 2022-10-14 | 2022-12-27 | 上药东英（江苏）药业有限公司 | 一种安全质量稳定的左西孟旦注射剂组合物及其制备方法 |
| CN116473930B (zh) * | 2023-05-17 | 2023-12-15 | 山东泰合医药科技有限公司 | 一种注射用左西孟旦及其制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998001111A1 (en) * | 1996-07-05 | 1998-01-15 | Orion-Yhtymä Oy | Transdermal compositions containing levosimendan |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2251615B (en) | 1991-01-03 | 1995-02-08 | Orion Yhtymae Oy | (-)-[[4-(1,4,5,6-tetrahydro-4-methyl-6-oxo-3-pyridazinyl)phenyl]hydrazono]pro panedinitrile |
| GB2266841A (en) | 1992-05-06 | 1993-11-17 | Orion Yhtymae Oy | Compounds for use as anti-ischemic medicaments |
| GB9606474D0 (en) | 1996-03-27 | 1996-06-05 | Orion Yhytmo Oy | Method for obtaining pure enantiomers of a pyridazinone derivative |
| FI980902A7 (fi) * | 1998-04-23 | 1999-10-24 | Orion Yhtymae Oyj | Levosimendaanin stabiileja koostumuksia |
| FI109659B (fi) * | 1999-09-10 | 2002-09-30 | Orion Yhtymae Oyj | Levosimendaanin farmaseuttisia liuoksia |
-
1999
- 1999-09-10 FI FI991925A patent/FI109659B/fi active
-
2000
- 2000-08-09 UA UA2002042873A patent/UA73954C2/uk unknown
- 2000-08-11 MY MYPI20003682A patent/MY125984A/en unknown
- 2000-08-30 TW TW089117581A patent/TWI242434B/zh not_active IP Right Cessation
- 2000-08-30 AR ARP000104525A patent/AR025449A1/es not_active Application Discontinuation
- 2000-09-06 CO CO00067212A patent/CO5180582A1/es active IP Right Grant
- 2000-09-08 BR BRPI0013924A patent/BRPI0013924B8/pt not_active IP Right Cessation
- 2000-09-08 PL PL354028A patent/PL202356B1/pl unknown
- 2000-09-08 HR HR20020298A patent/HRP20020298B1/xx not_active IP Right Cessation
- 2000-09-08 MX MXPA02002423A patent/MXPA02002423A/es active IP Right Grant
- 2000-09-08 CN CNB008126453A patent/CN1203855C/zh not_active Expired - Lifetime
- 2000-09-08 US US10/070,689 patent/US6730673B1/en not_active Expired - Lifetime
- 2000-09-08 PT PT00958562T patent/PT1210085E/pt unknown
- 2000-09-08 HU HU0202749A patent/HU228340B1/hu unknown
- 2000-09-08 WO PCT/FI2000/000761 patent/WO2001019334A2/en not_active Ceased
- 2000-09-08 EA EA200200348A patent/EA005067B1/ru not_active IP Right Cessation
- 2000-09-08 EE EEP200200129A patent/EE05375B1/xx unknown
- 2000-09-08 ES ES00958562T patent/ES2256034T3/es not_active Expired - Lifetime
- 2000-09-08 JP JP2001522969A patent/JP4708648B2/ja not_active Expired - Lifetime
- 2000-09-08 ME MEP-2008-866A patent/ME00523B/me unknown
- 2000-09-08 NZ NZ517605A patent/NZ517605A/en not_active IP Right Cessation
- 2000-09-08 CZ CZ20020788A patent/CZ303095B6/cs not_active IP Right Cessation
- 2000-09-08 HK HK03101189.6A patent/HK1049282B/zh not_active IP Right Cessation
- 2000-09-08 CA CA002382013A patent/CA2382013C/en not_active Expired - Lifetime
- 2000-09-08 IL IL14837900A patent/IL148379A0/xx active IP Right Grant
- 2000-09-08 KR KR20027002923A patent/KR100869752B1/ko not_active Expired - Lifetime
- 2000-09-08 TR TR2002/00620T patent/TR200200620T2/xx unknown
- 2000-09-08 RS YUP-169/02A patent/RS50445B/sr unknown
- 2000-09-08 EP EP00958562A patent/EP1210085B1/en not_active Expired - Lifetime
- 2000-09-08 AT AT00958562T patent/ATE315937T1/de active
- 2000-09-08 SK SK327-2002A patent/SK287154B6/sk not_active IP Right Cessation
- 2000-09-08 SI SI200030801T patent/SI1210085T1/sl unknown
- 2000-09-08 DE DE60025627T patent/DE60025627T2/de not_active Expired - Lifetime
- 2000-09-08 DK DK00958562T patent/DK1210085T3/da active
- 2000-09-08 AU AU70044/00A patent/AU771027B2/en not_active Expired
-
2002
- 2002-02-26 IL IL148379A patent/IL148379A/en unknown
- 2002-03-05 ZA ZA200201828A patent/ZA200201828B/xx unknown
- 2002-03-05 NO NO20021090A patent/NO331989B1/no not_active IP Right Cessation
- 2002-03-06 IS IS6296A patent/IS2244B/is unknown
- 2002-04-05 BG BG106589A patent/BG65827B1/bg unknown
-
2003
- 2003-11-10 US US10/703,565 patent/US6943164B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998001111A1 (en) * | 1996-07-05 | 1998-01-15 | Orion-Yhtymä Oy | Transdermal compositions containing levosimendan |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100869752B1 (ko) | 레보시멘단의 약학적 액제 | |
| US6548079B1 (en) | Moxifloxacin formulation containing common salt | |
| CN1829503B (zh) | 含有氟苯尼考的兽用水性可注射悬浮液 | |
| BG107748A (bg) | Фармацевтичен състав на дронедарон за парентерално приложение | |
| EA033988B1 (ru) | Инъецируемые фармацевтические композиции лефамулина | |
| AU740291B2 (en) | Stabilized pharmaceutical compositions based on quinupristine and on dalfopristine and their preparation | |
| US20060252804A1 (en) | Flupirtin injectable galenic form | |
| US6187746B1 (en) | Pharmaceutical compositions based on dalfopristine and on quinupristine, and preparation thereof | |
| US20230068866A1 (en) | Daptomycin formulation | |
| CA2142445C (en) | Injection solutions of azosemide which are ready for injection | |
| CN1611219A (zh) | 左西孟旦药物组合物及其制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20020305 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20050824 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20060817 Patent event code: PE09021S01D |
|
| AMND | Amendment | ||
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20070822 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20080530 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20070822 Comment text: Notification of reason for refusal Patent event code: PE06011S01I Patent event date: 20060817 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |
|
| J201 | Request for trial against refusal decision | ||
| PJ0201 | Trial against decision of rejection |
Patent event date: 20080630 Comment text: Request for Trial against Decision on Refusal Patent event code: PJ02012R01D Patent event date: 20080530 Comment text: Decision to Refuse Application Patent event code: PJ02011S01I Appeal kind category: Appeal against decision to decline refusal Decision date: 20080811 Appeal identifier: 2008101006352 Request date: 20080630 |
|
| AMND | Amendment | ||
| PB0901 | Examination by re-examination before a trial |
Comment text: Amendment to Specification, etc. Patent event date: 20080729 Patent event code: PB09011R02I Comment text: Request for Trial against Decision on Refusal Patent event date: 20080630 Patent event code: PB09011R01I Comment text: Amendment to Specification, etc. Patent event date: 20070406 Patent event code: PB09011R02I |
|
| B701 | Decision to grant | ||
| PB0701 | Decision of registration after re-examination before a trial |
Patent event date: 20080811 Comment text: Decision to Grant Registration Patent event code: PB07012S01D Patent event date: 20080804 Comment text: Transfer of Trial File for Re-examination before a Trial Patent event code: PB07011S01I |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20081114 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20081117 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| PR1001 | Payment of annual fee |
Payment date: 20111109 Start annual number: 4 End annual number: 4 |
|
| FPAY | Annual fee payment |
Payment date: 20121102 Year of fee payment: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20121102 Start annual number: 5 End annual number: 5 |
|
| FPAY | Annual fee payment |
Payment date: 20131031 Year of fee payment: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20131031 Start annual number: 6 End annual number: 6 |
|
| FPAY | Annual fee payment |
Payment date: 20141107 Year of fee payment: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20141107 Start annual number: 7 End annual number: 7 |
|
| FPAY | Annual fee payment |
Payment date: 20151105 Year of fee payment: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 20151105 Start annual number: 8 End annual number: 8 |
|
| FPAY | Annual fee payment |
Payment date: 20161104 Year of fee payment: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20161104 Start annual number: 9 End annual number: 9 |
|
| FPAY | Annual fee payment |
Payment date: 20171102 Year of fee payment: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 20171102 Start annual number: 10 End annual number: 10 |
|
| FPAY | Annual fee payment |
Payment date: 20181101 Year of fee payment: 11 |
|
| PR1001 | Payment of annual fee |
Payment date: 20181101 Start annual number: 11 End annual number: 11 |
|
| PC1801 | Expiration of term |
Termination date: 20210308 Termination category: Expiration of duration |