CN109157535A - 苯达莫司汀的制剂 - Google Patents
苯达莫司汀的制剂 Download PDFInfo
- Publication number
- CN109157535A CN109157535A CN201811307257.6A CN201811307257A CN109157535A CN 109157535 A CN109157535 A CN 109157535A CN 201811307257 A CN201811307257 A CN 201811307257A CN 109157535 A CN109157535 A CN 109157535A
- Authority
- CN
- China
- Prior art keywords
- bendamustine
- composition containing
- concentration
- polyethylene glycol
- composition
- 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.)
- Pending
Links
- 229960002707 bendamustine Drugs 0.000 title claims abstract description 152
- 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 abstract description 151
- 238000002360 preparation method Methods 0.000 title claims description 47
- 239000000203 mixture Substances 0.000 claims abstract description 152
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 138
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 137
- 239000012530 fluid Substances 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 22
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 20
- 150000002484 inorganic compounds Chemical class 0.000 claims abstract description 19
- 229910010272 inorganic material Inorganic materials 0.000 claims abstract description 19
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 242
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 129
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical group OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 claims description 34
- 229940035024 thioglycerol Drugs 0.000 claims description 33
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 28
- 239000001632 sodium acetate Substances 0.000 claims description 27
- 235000017281 sodium acetate Nutrition 0.000 claims description 27
- 230000003078 antioxidant effect Effects 0.000 claims description 19
- 235000006708 antioxidants Nutrition 0.000 claims description 19
- -1 nitrogenous compound Chemical class 0.000 claims description 11
- 238000005259 measurement Methods 0.000 claims description 10
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 claims description 3
- 235000019136 lipoic acid Nutrition 0.000 claims description 3
- 229960002663 thioctic acid Drugs 0.000 claims description 3
- IZFHEQBZOYJLPK-SSDOTTSWSA-N (R)-dihydrolipoic acid Chemical compound OC(=O)CCCC[C@@H](S)CCS IZFHEQBZOYJLPK-SSDOTTSWSA-N 0.000 claims description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 235000009508 confectionery Nutrition 0.000 claims description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 2
- 235000018417 cysteine Nutrition 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 229940043237 diethanolamine Drugs 0.000 claims description 2
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims description 2
- 229930182817 methionine Natural products 0.000 claims description 2
- 235000006109 methionine Nutrition 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000000473 propyl gallate Substances 0.000 claims description 2
- 235000010388 propyl gallate Nutrition 0.000 claims description 2
- 229940075579 propyl gallate Drugs 0.000 claims description 2
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003560 cancer drug Substances 0.000 claims 1
- 229960002433 cysteine Drugs 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 229960004452 methionine Drugs 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 36
- 230000007774 longterm Effects 0.000 abstract description 24
- 150000002148 esters Chemical class 0.000 abstract description 22
- 238000004128 high performance liquid chromatography Methods 0.000 abstract description 11
- 239000000523 sample Substances 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 24
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 23
- 235000002639 sodium chloride Nutrition 0.000 description 23
- 239000012535 impurity Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 17
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003814 drug Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- ZHSKUOZOLHMKEA-UHFFFAOYSA-N 4-[5-[bis(2-chloroethyl)amino]-1-methylbenzimidazol-2-yl]butanoic acid;hydron;chloride Chemical compound Cl.ClCCN(CCCl)C1=CC=C2N(C)C(CCCC(O)=O)=NC2=C1 ZHSKUOZOLHMKEA-UHFFFAOYSA-N 0.000 description 9
- 229960001215 bendamustine hydrochloride Drugs 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007857 degradation product Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000013068 control sample Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 5
- 235000011164 potassium chloride Nutrition 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000002253 acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 229950007687 macrogol ester Drugs 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 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 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- UCRNFUVTKPHVJL-UHFFFAOYSA-N O.O.O.[Na].C(C)(=O)O Chemical compound O.O.O.[Na].C(C)(=O)O UCRNFUVTKPHVJL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229960001484 edetic acid Drugs 0.000 description 2
- 239000000413 hydrolysate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- OPGYRRGJRBEUFK-UHFFFAOYSA-L disodium;diacetate Chemical compound [Na+].[Na+].CC([O-])=O.CC([O-])=O OPGYRRGJRBEUFK-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940066958 treanda Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
Classifications
-
- 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
- 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
- A61K47/02—Inorganic compounds
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Inorganic Chemistry (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261598729P | 2012-02-14 | 2012-02-14 | |
| US61/598,729 | 2012-02-14 | ||
| CN201380017489.7A CN104203235B (zh) | 2012-02-14 | 2013-02-14 | 苯达莫司汀的制剂 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380017489.7A Division CN104203235B (zh) | 2012-02-14 | 2013-02-14 | 苯达莫司汀的制剂 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109157535A true CN109157535A (zh) | 2019-01-08 |
Family
ID=48946112
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380017489.7A Expired - Fee Related CN104203235B (zh) | 2012-02-14 | 2013-02-14 | 苯达莫司汀的制剂 |
| CN201811307257.6A Pending CN109157535A (zh) | 2012-02-14 | 2013-02-14 | 苯达莫司汀的制剂 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380017489.7A Expired - Fee Related CN104203235B (zh) | 2012-02-14 | 2013-02-14 | 苯达莫司汀的制剂 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20130210879A1 (enExample) |
| EP (1) | EP2814487A4 (enExample) |
| JP (2) | JP2015506989A (enExample) |
| CN (2) | CN104203235B (enExample) |
| CA (1) | CA2864118A1 (enExample) |
| WO (1) | WO2013123227A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110123747A (zh) * | 2019-04-26 | 2019-08-16 | 嘉兴市爵拓科技有限公司 | 苯达莫司汀的制剂 |
| CN111166722A (zh) * | 2019-12-07 | 2020-05-19 | 四川汇宇制药有限公司 | 一种注射用盐酸苯达莫司汀冻干前药液及其制备方法 |
| CN111557904A (zh) * | 2020-04-09 | 2020-08-21 | 比卡生物科技（广州）有限公司 | 苯达莫司汀组合物及其用途 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS62327B1 (sr) | 2010-01-28 | 2021-10-29 | Eagle Pharmaceuticals Inc | Formulacije bendamustina |
| DK2827862T3 (da) | 2012-03-20 | 2024-02-12 | Eagle Pharmaceuticals Inc | Formuleringer af bendamustin |
| HRP20230276T1 (hr) | 2012-03-20 | 2023-04-28 | Eagle Pharmaceuticals, Inc. | Tekući pripravci bendamustina za uporabu u postupku liječenja stanja koja reagiraju na bendamustin kod pacijenata kojima za primjenu trebaju reducirani volumeni |
| US20230241218A1 (en) * | 2012-07-10 | 2023-08-03 | Eagle Pharmaceuticals, Inc. | Formulations of bendamustine |
| WO2015031198A2 (en) | 2013-08-27 | 2015-03-05 | Voudouris Vasilios | Bendamustine pharmaceutical compositions |
| US9603930B2 (en) | 2014-12-04 | 2017-03-28 | Navinta, Llc | Liquid bendamustine formulation |
| JP2016141734A (ja) * | 2015-02-02 | 2016-08-08 | 三菱瓦斯化学株式会社 | ポリアセタール樹脂組成物及び成形体 |
| CN110772480B (zh) * | 2016-03-25 | 2022-05-17 | 南京百劲企业管理咨询有限公司 | 苯达莫司汀药剂组合物及应用 |
| 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 |
| AR109503A1 (es) * | 2017-04-13 | 2018-12-19 | Onconova Therapeutics Inc | Composición farmacéutica que comprende (e)-2,4,6-trimetoxiestiril-3-[(carboximetil)amino]-4-metoxibencilsulfona, forma de dosificación oral y método de tratamiento |
| 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 |
| US11707450B1 (en) | 2022-03-03 | 2023-07-25 | Slayback Pharma Llc | Stable pharmaceutical compositions of bendamustine |
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| WO2007026771A1 (ja) * | 2005-08-31 | 2007-03-08 | Ono Pharmaceutical Co., Ltd. | 点滴用注射剤 |
| CA2659562A1 (en) * | 2006-08-14 | 2008-02-21 | Eisai R&D Management Co., Ltd. | Stable lyophilized preparation |
| DE102007003184A1 (de) * | 2007-01-22 | 2008-07-24 | Orlowski, Michael, Dr. | Verfahren zur Beladung von strukturierten Oberflächen |
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| CA2760085A1 (en) * | 2009-04-28 | 2010-11-04 | Cephalon, Inc. | Oral formulations of bendamustine |
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- 2013-02-14 WO PCT/US2013/026187 patent/WO2013123227A1/en not_active Ceased
- 2013-02-14 US US13/767,672 patent/US20130210879A1/en not_active Abandoned
- 2013-02-14 JP JP2014556835A patent/JP2015506989A/ja active Pending
- 2013-02-14 CN CN201380017489.7A patent/CN104203235B/zh not_active Expired - Fee Related
- 2013-02-14 EP EP13749829.1A patent/EP2814487A4/en not_active Withdrawn
- 2013-02-14 CA CA2864118A patent/CA2864118A1/en not_active Abandoned
- 2013-02-14 CN CN201811307257.6A patent/CN109157535A/zh active Pending
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- 2018-01-25 JP JP2018010326A patent/JP2018109005A/ja active Pending
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| US20110184036A1 (en) * | 2010-01-28 | 2011-07-28 | Eagle Pharmaceuticals, Inc. | Formulations of bendamustine |
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| WO2012015810A2 (en) * | 2010-07-28 | 2012-02-02 | Eagle Pharmaceuticals, Inc. | Pharmaceutical compositions containing pemetrexed having extended storage stability |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110123747A (zh) * | 2019-04-26 | 2019-08-16 | 嘉兴市爵拓科技有限公司 | 苯达莫司汀的制剂 |
| CN111166722A (zh) * | 2019-12-07 | 2020-05-19 | 四川汇宇制药有限公司 | 一种注射用盐酸苯达莫司汀冻干前药液及其制备方法 |
| CN111557904A (zh) * | 2020-04-09 | 2020-08-21 | 比卡生物科技（广州）有限公司 | 苯达莫司汀组合物及其用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2814487A1 (en) | 2014-12-24 |
| JP2015506989A (ja) | 2015-03-05 |
| CA2864118A1 (en) | 2013-08-22 |
| CN104203235A (zh) | 2014-12-10 |
| EP2814487A4 (en) | 2015-07-15 |
| WO2013123227A1 (en) | 2013-08-22 |
| CN104203235B (zh) | 2018-11-23 |
| JP2018109005A (ja) | 2018-07-12 |
| US20130210879A1 (en) | 2013-08-15 |
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