CZ282445B6 - Zlepšené lyofilizované ifosfamidové přípravky - Google Patents
Zlepšené lyofilizované ifosfamidové přípravky Download PDFInfo
- Publication number
- CZ282445B6 CZ282445B6 CS923176A CS317692A CZ282445B6 CZ 282445 B6 CZ282445 B6 CZ 282445B6 CS 923176 A CS923176 A CS 923176A CS 317692 A CS317692 A CS 317692A CZ 282445 B6 CZ282445 B6 CZ 282445B6
- Authority
- CZ
- Czechia
- Prior art keywords
- ifosfamide
- urea
- weight
- lyophilized
- formulations
- Prior art date
Links
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 title claims abstract description 88
- 229960001101 ifosfamide Drugs 0.000 title claims abstract description 88
- 238000002360 preparation method Methods 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000004202 carbamide Substances 0.000 claims abstract description 49
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 47
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 27
- 238000003860 storage Methods 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- PYTISYCTLQTCTM-UHFFFAOYSA-N sodium;2-sulfanylethanesulfonic acid Chemical compound [Na].OS(=O)(=O)CCS PYTISYCTLQTCTM-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 6
- 229940006193 2-mercaptoethanesulfonic acid Drugs 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical compound OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 claims description 4
- 239000012931 lyophilized formulation Substances 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 abstract description 53
- 238000009472 formulation Methods 0.000 abstract description 47
- 238000004108 freeze drying Methods 0.000 abstract description 15
- XOGTZOOQQBDUSI-UHFFFAOYSA-M Mesna Chemical compound [Na+].[O-]S(=O)(=O)CCS XOGTZOOQQBDUSI-UHFFFAOYSA-M 0.000 abstract description 5
- 238000012792 lyophilization process Methods 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 27
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 17
- 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 15
- 229930195725 Mannitol Natural products 0.000 description 15
- 239000000594 mannitol Substances 0.000 description 15
- 235000010355 mannitol Nutrition 0.000 description 15
- 239000004471 Glycine Substances 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 8
- ZZVDXRCAGGQFAK-UHFFFAOYSA-N 2h-oxazaphosphinine Chemical class N1OC=CC=P1 ZZVDXRCAGGQFAK-UHFFFAOYSA-N 0.000 description 6
- 239000003708 ampul Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 4
- 229960004397 cyclophosphamide Drugs 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229940045136 urea Drugs 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 210000001635 urinary tract Anatomy 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 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 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
- 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 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000004086 alkylating cytostatic agent Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229940041181 antineoplastic drug Drugs 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
- 201000011510 cancer Diseases 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229960004635 mesna Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000012982 microporous membrane Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GCOUHVNXKDHSAV-UHFFFAOYSA-N n,3-bis(2-chloroethyl)-2-oxidooxazaphosphinan-2-ium-2-amine Chemical compound ClCCN[N+]1([O-])OCCCP1CCCl GCOUHVNXKDHSAV-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- 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
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Materials For Medical Uses (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/781,436 US5227373A (en) | 1991-10-23 | 1991-10-23 | Lyophilized ifosfamide compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ317692A3 CZ317692A3 (en) | 1993-09-15 |
| CZ282445B6 true CZ282445B6 (cs) | 1997-07-16 |
Family
ID=25122737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS923176A CZ282445B6 (cs) | 1991-10-23 | 1992-10-20 | Zlepšené lyofilizované ifosfamidové přípravky |
Country Status (24)
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995007083A1 (en) * | 1993-09-10 | 1995-03-16 | F.H. Faulding & Co. Limited | Ifosfamide lyophilisate composition |
| US5789000A (en) * | 1994-11-14 | 1998-08-04 | Bionumerik Pharmaceuticals, Inc. | Sterile aqueous parenteral formulations of cis-diammine dichloro platinum |
| DE19529057B4 (de) * | 1995-08-08 | 2007-12-13 | Baxter Healthcare S.A. | Ifosfamid-Lyophilisat-Zubereitungen |
| KR100246757B1 (ko) | 1997-05-09 | 2000-03-15 | 윤종용 | 트랜스컨덕턴스 가변방법 및 회로와 그를 이용한 가변 대역 필터 및 가변 이득 증폭기 |
| DE19733305A1 (de) * | 1997-08-01 | 1999-02-04 | Asta Medica Ag | Pharmazeutische Zusammensetzung enthaltend Ifosfamid und Carnitin |
| ES2277397T3 (es) * | 1997-10-13 | 2007-07-01 | Stada Arzneimittel Ag | Formas liquidas de administracion de productos farmaceuticos que contienen oxazafosforina. |
| US5972912A (en) * | 1998-12-17 | 1999-10-26 | S.P. Pharmaceuticals | Method for lyophilizing ifosfamide |
| CN1126547C (zh) * | 2000-07-19 | 2003-11-05 | 南京振中生物工程有限公司 | 香菇多糖冻干粉针剂及其制备方法 |
| US6613927B1 (en) | 2002-02-08 | 2003-09-02 | American Pharmaceutical Partners, Inc. | Sterile lyophilized ifosfamide and associated methods |
| CN100346784C (zh) * | 2002-02-22 | 2007-11-07 | 先灵公司 | 抗肿瘤剂,特别是替莫唑胺的药物制剂,其制备方法和用途 |
| NZ538584A (en) * | 2002-09-05 | 2007-05-31 | Bharat Serums & Vaccines Ltd | Stable liquid composition of oxazaphosphorine, mesna and etherified beta-cyclodextrin |
| CN100463678C (zh) * | 2002-12-02 | 2009-02-25 | 印度血清及疫苗有限公司 | 用于肠胃外给药的异环磷酰胺组合物及其制备方法 |
| US7199111B2 (en) * | 2002-12-02 | 2007-04-03 | Bharat Serums & Vaccines Ltd. | Aqueous ifosfamide compositions for parenteral administration and a process for their preparations |
| WO2005032515A1 (en) * | 2003-10-01 | 2005-04-14 | Baxter International Inc. | New use, pharmaceutical preparations as well as a process for their production |
| EP1814544A4 (en) * | 2004-11-05 | 2009-12-02 | Cephalon Inc | CANCER TREATMENTS |
| US8436190B2 (en) | 2005-01-14 | 2013-05-07 | Cephalon, Inc. | Bendamustine pharmaceutical compositions |
| WO2007079147A2 (en) | 2005-12-28 | 2007-07-12 | Advanced Bionutrition Corporation | A delivery vehicle for probiotic bacteria comprising a dry matrix of polysaccharides, saccharides and polyols in a glass form and methods of making same |
| US8968721B2 (en) | 2005-12-28 | 2015-03-03 | Advanced Bionutrition Corporation | Delivery vehicle for probiotic bacteria comprising a dry matrix of polysaccharides, saccharides and polyols in a glass form and methods of making same |
| SI2071917T1 (sl) * | 2006-09-29 | 2013-03-29 | Infa S.A. | Pakirni sistem za farmacevtske sestavke in komplet za intravensko aplikacijo |
| US8460726B2 (en) | 2006-12-18 | 2013-06-11 | Advanced Bionutrition Corporation | Dry food product containing live probiotic |
| WO2008140724A1 (en) * | 2007-05-08 | 2008-11-20 | Schering Corporation | Methods of treatment using intravenous formulations comprising temozolomide |
| AR072777A1 (es) | 2008-03-26 | 2010-09-22 | Cephalon Inc | Formas solidas de clorhidrato de bendamustina |
| EP2326306A1 (en) * | 2008-09-25 | 2011-06-01 | Cephalon, Inc. | Liquid formulations of bendamustine |
| CN103554030A (zh) * | 2009-01-15 | 2014-02-05 | 赛福伦公司 | 苯达莫司汀游离碱的新颖形式 |
| EP2410996B1 (en) | 2009-03-27 | 2017-08-02 | Advanced Bionutrition Corp. | Microparticulated vaccines for the oral or nasal vaccination and boostering of animals including fish |
| PL2435554T3 (pl) * | 2009-05-26 | 2018-01-31 | Advanced Bionutrition Corp | Stabilna kompozycja suchego proszku zawierająca biologicznie aktywne mikroorganizmy i/lub materiały bioaktywne i sposoby jej wykonania |
| RU2535869C2 (ru) | 2010-01-28 | 2014-12-20 | Эдванст Бионутришн Корпорейшн | Сухая стекловидная композиция для стабилизации и защиты биологически активного материала и способ ее получения |
| US9504750B2 (en) | 2010-01-28 | 2016-11-29 | Advanced Bionutrition Corporation | Stabilizing composition for biological materials |
| BR112013003244B1 (pt) | 2010-08-13 | 2018-07-17 | Advanced Bionutrition Corp | composição seca estabilizante para material biológico, seu método de preparação, e formulação de carreamento oral |
| WO2015101665A1 (en) * | 2014-01-06 | 2015-07-09 | Auxin Surgery Sa | Lyophilized mesna compositions |
| US10342769B2 (en) | 2014-11-14 | 2019-07-09 | Navinta Iii Inc | Carmustine pharmaceutical composition |
| EP3328215B1 (en) | 2015-07-29 | 2021-07-07 | Advanced BioNutrition Corp. | Stable dry probiotic compositions for special dietary uses |
| JP6706988B2 (ja) * | 2016-07-20 | 2020-06-10 | 日本化薬株式会社 | ボルテゾミブを含有する医薬組成物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3732340A (en) * | 1966-07-11 | 1973-05-08 | Asta Werke Ag Chem Fab | N',o-propylene phosphoric acid ester diamides |
| US4537883A (en) * | 1982-11-12 | 1985-08-27 | Mead Johnson & Company | Lyophilized cyclophosphamide |
| ZA851062B (en) * | 1984-03-01 | 1985-11-27 | Asta Werke Ag Chem Fab | Salts of oxazaphosphorine derivatives and process for their production |
| ES2038623T3 (es) * | 1986-07-11 | 1993-08-01 | Asta Medica Aktiengesellschaft | Procedimiento para preparar soluciones de oxazafosforinas con estabilidad mejorada. |
| NO873860L (no) * | 1986-10-31 | 1988-05-02 | Asta Pharma Ag | Ifosfamid-lyofilisat og fremgangsmaate til deres fremstilling. |
| DE3862595D1 (de) * | 1987-03-06 | 1991-06-06 | Asta Pharma Ag | Verfahren zur herstellung von ifosfamid mit verbesserten eigenschaften. |
| ATE65402T1 (de) * | 1988-03-19 | 1991-08-15 | Asta Pharma Ag | Ifosfamid-mesna-lyophilisat und verfahren zu dessen herstellung. |
| US5036060A (en) * | 1988-07-25 | 1991-07-30 | Fujisawa Usa, Inc. | Cyclophosphamide |
-
1991
- 1991-10-23 US US07/781,436 patent/US5227373A/en not_active Expired - Lifetime
-
1992
- 1992-10-20 MY MYPI92001893A patent/MY109794A/en unknown
- 1992-10-20 SK SK3176-92A patent/SK279869B6/sk not_active IP Right Cessation
- 1992-10-20 NZ NZ244816A patent/NZ244816A/en not_active IP Right Cessation
- 1992-10-20 CZ CS923176A patent/CZ282445B6/cs not_active IP Right Cessation
- 1992-10-20 ZA ZA928104A patent/ZA928104B/xx unknown
- 1992-10-20 KR KR1019920019270A patent/KR100247161B1/ko not_active Expired - Fee Related
- 1992-10-21 CA CA002081061A patent/CA2081061A1/en not_active Abandoned
- 1992-10-21 HU HU9203306A patent/HU221428B/hu not_active IP Right Cessation
- 1992-10-21 AU AU27166/92A patent/AU658011B2/en not_active Ceased
- 1992-10-21 EG EG63992A patent/EG20114A/xx active
- 1992-10-21 IL IL10349692A patent/IL103496A/en not_active IP Right Cessation
- 1992-10-21 CN CN92111646A patent/CN1046202C/zh not_active Expired - Fee Related
- 1992-10-21 TW TW081108396A patent/TW217987B/zh not_active IP Right Cessation
- 1992-10-22 DK DK92118093T patent/DK0538858T3/da active
- 1992-10-22 ES ES92118093T patent/ES2125880T3/es not_active Expired - Lifetime
- 1992-10-22 JP JP32457092A patent/JP3576180B2/ja not_active Expired - Lifetime
- 1992-10-22 EP EP92118093A patent/EP0538858B1/en not_active Expired - Lifetime
- 1992-10-22 AT AT92118093T patent/ATE175354T1/de not_active IP Right Cessation
- 1992-10-22 FI FI924797A patent/FI107701B/fi active
- 1992-10-22 RU RU92004463A patent/RU2106138C1/ru not_active IP Right Cessation
- 1992-10-22 DE DE69228105T patent/DE69228105T2/de not_active Expired - Lifetime
- 1992-10-23 MX MX9206105A patent/MX9206105A/es unknown
-
1995
- 1995-06-20 HU HU95P/P00276P patent/HU211293A9/hu unknown
-
1999
- 1999-03-31 GR GR990400929T patent/GR3029835T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20101020 |