HRP20210915T1 - Formulacije bendamustina - Google Patents
Formulacije bendamustina Download PDFInfo
- Publication number
- HRP20210915T1 HRP20210915T1 HRP20210915TT HRP20210915T HRP20210915T1 HR P20210915 T1 HRP20210915 T1 HR P20210915T1 HR P20210915T T HRP20210915T T HR P20210915TT HR P20210915 T HRP20210915 T HR P20210915T HR P20210915 T1 HRP20210915 T1 HR P20210915T1
- Authority
- HR
- Croatia
- Prior art keywords
- bendamustine
- term storage
- preparation containing
- during long
- stable during
- Prior art date
Links
- YTKUWDBFDASYHO-UHFFFAOYSA-N bendamustine Chemical compound ClCCN(CCCl)C1=CC=C2N(C)C(CCCC(O)=O)=NC2=C1 YTKUWDBFDASYHO-UHFFFAOYSA-N 0.000 title claims 23
- 229960002707 bendamustine Drugs 0.000 title claims 23
- 239000000203 mixture Substances 0.000 title claims 4
- 238000009472 formulation Methods 0.000 title 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 15
- 230000007774 longterm Effects 0.000 claims 14
- 238000004128 high performance liquid chromatography Methods 0.000 claims 8
- 239000002202 Polyethylene glycol Substances 0.000 claims 5
- 239000012530 fluid Substances 0.000 claims 5
- 229920001223 polyethylene glycol Polymers 0.000 claims 5
- 239000003963 antioxidant agent Substances 0.000 claims 4
- 235000006708 antioxidants Nutrition 0.000 claims 4
- 239000012535 impurity Substances 0.000 claims 4
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 claims 4
- 230000000087 stabilizing effect Effects 0.000 claims 4
- 230000003078 antioxidant effect Effects 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229940035024 thioglycerol Drugs 0.000 claims 3
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims 2
- IZFHEQBZOYJLPK-SSDOTTSWSA-N (R)-dihydrolipoic acid Chemical compound OC(=O)CCCC[C@@H](S)CCS IZFHEQBZOYJLPK-SSDOTTSWSA-N 0.000 claims 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 150000007824 aliphatic compounds Chemical class 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- 229960002433 cysteine Drugs 0.000 claims 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims 1
- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 claims 1
- 235000019136 lipoic acid Nutrition 0.000 claims 1
- 229930182817 methionine Natural products 0.000 claims 1
- 229960004452 methionine Drugs 0.000 claims 1
- 235000006109 methionine Nutrition 0.000 claims 1
- 239000000473 propyl gallate Substances 0.000 claims 1
- 229940075579 propyl gallate Drugs 0.000 claims 1
- 235000010388 propyl gallate Nutrition 0.000 claims 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 claims 1
- 229960002663 thioctic acid Drugs 0.000 claims 1
Classifications
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- 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
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K47/06—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
- 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
- A61K47/186—Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide
-
- 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
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
-
- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- 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
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Materials For Medical Uses (AREA)
Claims (13)
1. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju, naznačen time, da obuhvaća:
a) bendamustin ili njegovu farmaceutski prihvatljivu sol; i
b) farmaceutski prihvatljiv fluid koji sadrži
i) polietilen glikol i propilen glikol; i
ii) stabilizacijsku količinu antioksidansa;
pri čemu navedeni pripravak koji sadrži bendamustin posjeduje manje od 5% ukupnih nečistoća, na temelju normaliziranog područja vršnog odziva („PAR“- prema engl. „peak area response“), što se određuje putem tekućinske kromatografije visoke djelotvornosti („HPLC“ prema engl. „high performance liquid chromatography“) s valnom duljinom od 223 nm, nakon najmanje 15 mjeseci skladištenja na temperaturi od 5 °C do 25 °C.
2. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema patentnom zahtjevu 1, naznačen time, da koncentracija bendamustina iznosi od 20 mg/mL do 60 mg/mL.
3. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema patentnom zahtjevu 2, naznačen time, da koncentracija bendamustina iznosi od 25 mg/mL do 50 mg/mL.
4. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema patentnom zahtjevu 1, naznačen time, da farmaceutski prihvatljiv fluid sadrži oko 90% polietilen glikola i oko 10% propilen glikola.
5. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema patentnom zahtjevu 4, naznačen time, da farmaceutski prihvatljiv fluid sadrži oko 85% polietilen glikola i oko 15% propilen glikola.
6. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time, da se antioksidans bira iz skupine koja se sastoji od tioglicerola, monotioglicerola, lipoične kiseline, propil galata, metionina, cisteina, metabisulfita, natrijevog formaldehid sulfoksilata, aromatskih i alifatskih spojeva koji sadrže fenol te dihidrolipoične kiseline.
7. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time, da stabilizacijska količina antioksidansa iznosi od 2,5 mg/mL do 35 mg/mL.
8. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema patentnom zahtjevu 7, naznačen time, da stabilizacijska količina antioksidansa iznosi od 5 mg/mL do 20 mg/mL.
9. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time, da je spomenuto dugotrajno skladištenje najmanje dvije godine.
10. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time, da spomenuti pripravak koji sadrži bendamustin posjeduje manje od 3% ukupnih nečistoća, PAR se određuje putem HPLC s valnom duljinom od 223 nm, nakon najmanje dvije godine skladištenja na temperaturi od 5 °C do 25 °C.
11. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema patentnom zahtjevu 1, naznačen time, da obuhvaća:
a) bendamustin ili njegovu farmaceutski prihvatljivu sol; i
b) farmaceutski prihvatljiv fluid koji sadrži
i) polietilen glikol i propilen glikol; i
ii) stabilizacijsku količinu tioglicerola;
pri čemu navedeni pripravak koji sadrži bendamustin posjeduje manje od 5% ukupnih nečistoća, na temelju normaliziranog područja vršnog odziva („PAR“), što se određuje putem tekućinske kromatografije visoke djelotvornosti („HPLC“) s valnom duljinom od 223 nm, nakon najmanje 15 mjeseci skladištenja na temperaturi od 5 °C do 25 °C.
12. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema patentnom zahtjevu 1, naznačen time, da obuhvaća:
a) bendamustin ili njegovu farmaceutski prihvatljivu sol pri koncentraciji od oko 50 mg/mL; i
b) farmaceutski prihvatljiv fluid koji sadrži:
i) 90% polietilen glikola i 10% propilen glikola; i
ii) tioglicerol pri koncentraciji od oko 2,5 mg/mL;
pri čemu navedeni pripravak koji sadrži bendamustin posjeduje manje od 5% ukupnih nečistoća, na temelju normaliziranog područja vršnog odziva („PAR“), što se određuje putem tekućinske kromatografije visoke djelotvornosti („HPLC“) s valnom duljinom od 223 nm, nakon najmanje 15 mjeseci skladištenja na temperaturi od 5 °C do 25 °C.
13. Pripravak koji sadrži bendamustin stabilan pri dugotrajnom skladištenju prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time, da je za uporabu u liječenju raka kod sisavaca.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29910010P | 2010-01-28 | 2010-01-28 | |
| EP16020363.4A EP3158991B1 (en) | 2010-01-28 | 2011-01-28 | Formulations of bendamustine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20210915T1 true HRP20210915T1 (hr) | 2021-10-01 |
Family
ID=44309429
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20161771TT HRP20161771T4 (hr) | 2010-01-28 | 2016-12-22 | Formulacije bendamustina |
| HRP20210915TT HRP20210915T1 (hr) | 2010-01-28 | 2021-06-09 | Formulacije bendamustina |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20161771TT HRP20161771T4 (hr) | 2010-01-28 | 2016-12-22 | Formulacije bendamustina |
Country Status (16)
| Country | Link |
|---|---|
| US (14) | US8609707B2 (hr) |
| EP (3) | EP3158991B1 (hr) |
| JP (2) | JP5795600B2 (hr) |
| CA (1) | CA2787568C (hr) |
| CY (2) | CY1118769T1 (hr) |
| DK (2) | DK3158991T3 (hr) |
| ES (2) | ES2875374T3 (hr) |
| HR (2) | HRP20161771T4 (hr) |
| HU (2) | HUE054836T2 (hr) |
| LT (2) | LT2528602T (hr) |
| PL (2) | PL3158991T3 (hr) |
| PT (2) | PT3158991T (hr) |
| RS (2) | RS55491B2 (hr) |
| SI (2) | SI2528602T2 (hr) |
| SM (1) | SMT201700043B (hr) |
| WO (1) | WO2011094565A1 (hr) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3158991B1 (en) | 2010-01-28 | 2021-03-17 | Eagle Pharmaceuticals, Inc. | Formulations of bendamustine |
| US20120237492A1 (en) | 2011-02-18 | 2012-09-20 | Kythera Biopharmaceuticals, Inc. | Treatment of submental fat |
| WO2013112762A1 (en) * | 2012-01-24 | 2013-08-01 | Innopharma, Inc. | Bendamustine compositions and methods therefore |
| US20130210879A1 (en) * | 2012-02-14 | 2013-08-15 | Eagle Pharmaceuticals, Inc. | Formulations of bendamustine |
| WO2013142358A1 (en) * | 2012-03-20 | 2013-09-26 | Eagle Pharmaceuticals, Inc. | Formulations of bendamustine |
| RS58744B1 (sr) * | 2012-03-20 | 2019-06-28 | Eagle Pharmaceuticals Inc | Tečna kompozicija za upotrebu u postupku lečenja stanja koja reaguju na bendamustin kod pacijenata kojima su potrebne smanjene zapremine za davanje |
| CN105491886B (zh) | 2013-08-27 | 2019-01-29 | V·沃道里斯 | 苯达莫司汀医药组合物 |
| EA201690621A1 (ru) * | 2013-09-20 | 2016-07-29 | Сантен Фармасьютикал Ко., Лтд. | Полиэтиленгликольсодержащие композиции |
| WO2015054550A1 (en) * | 2013-10-11 | 2015-04-16 | Luitpold Pharmaceuticals, Inc. | Bendamustine pharmaceutical compositions |
| CA2941632C (en) | 2014-03-13 | 2023-10-24 | Vasilios VOUDOURIS | Bendamustine solid dispersions and continuous infusion |
| WO2016005995A2 (en) * | 2014-07-10 | 2016-01-14 | Leiutis Pharmaceuticals Pvt. Ltd. | Glycol free stable liquid compositions of bendamustine |
| US9603930B2 (en) | 2014-12-04 | 2017-03-28 | Navinta, Llc | Liquid bendamustine formulation |
| KR20180100309A (ko) * | 2015-11-04 | 2018-09-10 | 키쎄라 바이오파마슈티컬즈 인코포레이티드 | 데옥시콜산 및 이의 염을 사용한 축적된 지방의 치료 방법 |
| US11826466B2 (en) | 2016-08-31 | 2023-11-28 | Navinta, Llc | Bendamustine solution formulations |
| US10905677B2 (en) * | 2016-08-31 | 2021-02-02 | Navinta, Llc | Bendamustine solution formulations |
| ES2928931T3 (es) | 2018-03-29 | 2022-11-23 | Project Pharmaceutics Gmbh | Formulación farmacéutica líquida |
| WO2020035806A1 (en) | 2018-08-17 | 2020-02-20 | Hospira Australia Pty Ltd | Liquid bendamustine pharmaceutical compositions |
| US11730815B2 (en) | 2018-11-26 | 2023-08-22 | Good Health, Llc | Stable liquid pharmaceutical compositions comprising bendamustine |
| JP2020090481A (ja) * | 2018-11-27 | 2020-06-11 | 日本化薬株式会社 | ベンダムスチンを含有する溶液製剤 |
| JP7235288B2 (ja) * | 2019-01-07 | 2023-03-08 | コーアイセイ株式会社 | ベンダムスチンの液体製剤 |
| WO2020170104A1 (en) * | 2019-02-18 | 2020-08-27 | Shilpa Medicare Limited | Liquid bendamustine parenteral compositions |
| WO2021161876A1 (ja) * | 2020-02-10 | 2021-08-19 | 富士フイルム株式会社 | ベンダムスチン液剤 |
| EP4419147A1 (en) | 2021-10-22 | 2024-08-28 | Project Pharmaceutics GmbH | Liquid pharmaceutical formulation |
| GB202118175D0 (en) | 2021-12-15 | 2022-01-26 | Arecor Ltd | Novel composition |
| US11707450B1 (en) | 2022-03-03 | 2023-07-25 | Slayback Pharma Llc | Stable pharmaceutical compositions of bendamustine |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE159289C (hr) * | 1903-10-08 | 1905-03-16 | ||
| DE80967C (hr) | ||||
| US4071620A (en) | 1977-01-10 | 1978-01-31 | American Home Products Corporation | Stabilization of oxygen sensitive dose forms |
| DD152989A1 (de) | 1980-09-11 | 1981-12-16 | Klaus Kunze | Anordnung zur korrektur von soll-und istwerten |
| DD159289A1 (de) * | 1981-06-01 | 1983-03-02 | Uwe Olthoff | Verfahren zur herstellung stabiler injektionsloesungen von n-lostverbindungen |
| DE3446873A1 (de) * | 1984-12-21 | 1986-07-10 | Merckle Gmbh | Fluessige diclofenac-zubereitungen |
| US5204335A (en) | 1986-10-31 | 1993-04-20 | Asta Pharma Aktiengesellschaft | Ifosfamide lyophilisate and process for its preparation |
| US4879286A (en) | 1987-01-28 | 1989-11-07 | Lyphomed, Inc. | Cyclophosphamide |
| US5223515A (en) | 1988-08-18 | 1993-06-29 | Takeda Chemical Industries, Ltd. | Injectable solution containing a pyridyl methylsulfinylbenzimidazole |
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| CZ210496A3 (en) * | 1994-01-24 | 1996-12-11 | Procter & Gamble | Method improving solution process of difficult-to dissolve pharmaceutically active compounds |
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