CA2443052A1 - Utilisation de derives cationiques du dextrane pour proteger les organes a limitation de dose - Google Patents
Utilisation de derives cationiques du dextrane pour proteger les organes a limitation de dose Download PDFInfo
- Publication number
- CA2443052A1 CA2443052A1 CA002443052A CA2443052A CA2443052A1 CA 2443052 A1 CA2443052 A1 CA 2443052A1 CA 002443052 A CA002443052 A CA 002443052A CA 2443052 A CA2443052 A CA 2443052A CA 2443052 A1 CA2443052 A1 CA 2443052A1
- Authority
- CA
- Canada
- Prior art keywords
- dextran
- mol
- cationic
- substituents
- positively charged
- 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.)
- Abandoned
Links
- 210000000056 organ Anatomy 0.000 title claims abstract description 33
- 239000003814 drug Substances 0.000 claims abstract description 37
- 125000001424 substituent group Chemical group 0.000 claims abstract description 34
- 230000000694 effects Effects 0.000 claims abstract description 20
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 16
- 230000009885 systemic effect Effects 0.000 claims abstract description 11
- 201000011510 cancer Diseases 0.000 claims abstract description 10
- 201000010099 disease Diseases 0.000 claims abstract description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 229920002307 Dextran Polymers 0.000 claims description 56
- 210000003734 kidney Anatomy 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 31
- 229940079593 drug Drugs 0.000 claims description 30
- 125000002091 cationic group Chemical group 0.000 claims description 25
- 239000004472 Lysine Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 17
- 150000001413 amino acids Chemical class 0.000 claims description 16
- 238000009121 systemic therapy Methods 0.000 claims description 15
- 238000006467 substitution reaction Methods 0.000 claims description 12
- 230000002285 radioactive effect Effects 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 10
- 239000004475 Arginine Substances 0.000 claims description 9
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 8
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 8
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 8
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 8
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 8
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 8
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 8
- 229960003104 ornithine Drugs 0.000 claims description 8
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 7
- 239000003018 immunosuppressive agent Substances 0.000 claims description 7
- 229940125721 immunosuppressive agent Drugs 0.000 claims description 7
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000003589 nefrotoxic effect Effects 0.000 claims description 5
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 4
- 239000002254 cytotoxic agent Substances 0.000 claims description 4
- 229940127089 cytotoxic agent Drugs 0.000 claims description 4
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 4
- 239000013061 administrable dose form Substances 0.000 claims description 3
- 239000000824 cytostatic agent Substances 0.000 abstract description 13
- 230000001085 cytostatic effect Effects 0.000 abstract description 11
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 239000003223 protective agent Substances 0.000 abstract description 10
- 230000001607 nephroprotective effect Effects 0.000 abstract description 5
- 238000001802 infusion Methods 0.000 description 8
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 125000000539 amino acid group Chemical group 0.000 description 6
- 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 5
- 229920002521 macromolecule Polymers 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 231100000331 toxic Toxicity 0.000 description 5
- 230000002588 toxic effect Effects 0.000 description 5
- 108050001286 Somatostatin Receptor Proteins 0.000 description 4
- 102000011096 Somatostatin receptor Human genes 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 206010029155 Nephropathy toxic Diseases 0.000 description 3
- 210000001185 bone marrow Anatomy 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 231100000381 nephrotoxic Toxicity 0.000 description 3
- 231100000417 nephrotoxicity Toxicity 0.000 description 3
- 230000007694 nephrotoxicity Effects 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 208000009304 Acute Kidney Injury Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010059024 Gastrointestinal toxicity Diseases 0.000 description 2
- 150000008575 L-amino acids Chemical class 0.000 description 2
- 208000033626 Renal failure acute Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 201000011040 acute kidney failure Diseases 0.000 description 2
- 208000012998 acute renal failure Diseases 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 108010062796 arginyllysine Proteins 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 239000000890 drug combination Substances 0.000 description 2
- 238000001962 electrophoresis Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 231100000414 gastrointestinal toxicity Toxicity 0.000 description 2
- 239000003978 infusion fluid Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 231100000957 no side effect Toxicity 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229940126585 therapeutic drug Drugs 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 102000051366 Glycosyltransferases Human genes 0.000 description 1
- 108700023372 Glycosyltransferases Proteins 0.000 description 1
- 241000192132 Leuconostoc Species 0.000 description 1
- 241001468194 Leuconostoc mesenteroides subsp. dextranicum Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 231100000987 absorbed dose Toxicity 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229960001704 carbimazole Drugs 0.000 description 1
- CFOYWRHIYXMDOT-UHFFFAOYSA-N carbimazole Chemical compound CCOC(=O)N1C=CN(C)C1=S CFOYWRHIYXMDOT-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940039231 contrast media Drugs 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 231100000317 environmental toxin Toxicity 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000009993 protective function Effects 0.000 description 1
- 210000000512 proximal kidney tubule Anatomy 0.000 description 1
- 239000000941 radioactive substance Substances 0.000 description 1
- 150000003384 small molecules Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229960002178 thiamazole Drugs 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 210000002700 urine Anatomy 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/721—Dextrans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0021—Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention concerne l'utilisation de dérivés cationiques du dextrane avec des substituants comprenant des groupes latéraux chargés positivement comme agents de protection destinés aux organes à limitation de dose dans le traitement systémique de maladies telles que le cancer. Ces dérivés cationiques du dextrane sont particulièrement utiles comme agents nephroprotecteurs chez un sujet soumis à un traitement systémique avec des agents pharmaceutiques cytostatiques, des composés renfermant des agents pharmaceutiques cytostatiques, des radionucléides ou des composés renfermant des radionucléides contre les lésions rénales. Ces dérivés cationiques du dextrane ne protègent pas uniquement les organes à limitation de dose, mais sont également mieux tolérés et entraînent moins d'effets secondaires que les agents de protection couramment utilisés.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20010764A FI20010764A0 (fi) | 2001-04-11 | 2001-04-11 | Kationiset dekstraanijohdannaiset käytettäväksi munuaisten suojaamiseen |
| FI20010764 | 2001-04-11 | ||
| PCT/FI2002/000305 WO2002083154A1 (fr) | 2001-04-11 | 2002-04-11 | Utilisation de derives cationiques du dextrane pour proteger les organes a limitation de dose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2443052A1 true CA2443052A1 (fr) | 2002-10-24 |
Family
ID=8560975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002443052A Abandoned CA2443052A1 (fr) | 2001-04-11 | 2002-04-11 | Utilisation de derives cationiques du dextrane pour proteger les organes a limitation de dose |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1383517A1 (fr) |
| JP (1) | JP2004525181A (fr) |
| KR (1) | KR20040018350A (fr) |
| BR (1) | BR0208860A (fr) |
| CA (1) | CA2443052A1 (fr) |
| EE (1) | EE200300502A (fr) |
| FI (1) | FI20010764A0 (fr) |
| HU (1) | HUP0401386A3 (fr) |
| IL (1) | IL158153A0 (fr) |
| NO (1) | NO20034561L (fr) |
| PL (1) | PL363024A1 (fr) |
| RU (1) | RU2003132683A (fr) |
| WO (1) | WO2002083154A1 (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010102066A1 (fr) | 2009-03-05 | 2010-09-10 | Bend Research, Inc. | Poudre de polymère de dextrane destinée à l'administration de produits pharmaceutiques par inhalation |
| EP2411137B1 (fr) | 2009-03-27 | 2016-09-07 | Bend Research, Inc. | Procédé de séchage par pulvérisation |
| PT2611529T (pt) | 2010-09-03 | 2019-05-09 | Bend Res Inc | Método de secagem por pulverização |
| US9084944B2 (en) | 2010-09-03 | 2015-07-21 | Bend Research, Inc. | Spray-drying apparatus and methods of using the same |
| US8815294B2 (en) | 2010-09-03 | 2014-08-26 | Bend Research, Inc. | Pharmaceutical compositions of dextran polymer derivatives and a carrier material |
| WO2012040502A1 (fr) | 2010-09-24 | 2012-03-29 | Bend Research, Inc. | Procédé et appareil de séchage par pulvérisation à température élevée |
| US9084727B2 (en) | 2011-05-10 | 2015-07-21 | Bend Research, Inc. | Methods and compositions for maintaining active agents in intra-articular spaces |
| DE102014016901B4 (de) * | 2014-09-17 | 2021-08-12 | Friedrich-Schiller-Universität Jena | Verfahren zur Herstellung für neue Dextranderivate als Wirkstoffträgersystem und deren Verwendung |
| US20190353565A1 (en) * | 2016-12-01 | 2019-11-21 | Norbert Gretz | Means and methods for visualization of tissue structures |
| IL293883A (en) * | 2019-12-14 | 2022-08-01 | Manu Chaudhary | Formulations of polybasic drugs to reduce multi-organ toxicity |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3414491A1 (de) * | 1984-04-17 | 1985-10-24 | Hans Dr. 8202 Bad Aibling Dietl | L-aminosaeurengemische fuer die parenterale und orale anwendung bei nierenerkrankungen |
| US5290538A (en) * | 1988-12-22 | 1994-03-01 | Skrezek Christian | Nephro protective infusion solutions |
| SE9803482D0 (sv) * | 1998-10-13 | 1998-10-13 | Anders Holmberg | Ion exchange tumor targeting (IETT) |
| CA2379696C (fr) * | 1999-07-16 | 2009-09-15 | Mallinckrodt, Inc. | Inhibition de l'absorption renale de molecules pouvant potentiellement endommager les reins |
-
2001
- 2001-04-11 FI FI20010764A patent/FI20010764A0/fi unknown
-
2002
- 2002-04-11 RU RU2003132683/15A patent/RU2003132683A/ru not_active Application Discontinuation
- 2002-04-11 WO PCT/FI2002/000305 patent/WO2002083154A1/fr not_active Ceased
- 2002-04-11 PL PL02363024A patent/PL363024A1/xx unknown
- 2002-04-11 JP JP2002580956A patent/JP2004525181A/ja not_active Withdrawn
- 2002-04-11 EP EP02714245A patent/EP1383517A1/fr not_active Withdrawn
- 2002-04-11 KR KR10-2003-7013284A patent/KR20040018350A/ko not_active Withdrawn
- 2002-04-11 IL IL15815302A patent/IL158153A0/xx unknown
- 2002-04-11 EE EEP200300502A patent/EE200300502A/xx unknown
- 2002-04-11 BR BR0208860-6A patent/BR0208860A/pt not_active Application Discontinuation
- 2002-04-11 HU HU0401386A patent/HUP0401386A3/hu unknown
- 2002-04-11 CA CA002443052A patent/CA2443052A1/fr not_active Abandoned
-
2003
- 2003-10-10 NO NO20034561A patent/NO20034561L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL363024A1 (en) | 2004-11-15 |
| EP1383517A1 (fr) | 2004-01-28 |
| IL158153A0 (en) | 2004-03-28 |
| KR20040018350A (ko) | 2004-03-03 |
| HUP0401386A3 (en) | 2005-06-28 |
| FI20010764A0 (fi) | 2001-04-11 |
| NO20034561L (no) | 2003-12-09 |
| HUP0401386A2 (hu) | 2004-12-28 |
| JP2004525181A (ja) | 2004-08-19 |
| WO2002083154A1 (fr) | 2002-10-24 |
| RU2003132683A (ru) | 2005-04-10 |
| EE200300502A (et) | 2003-12-15 |
| NO20034561D0 (no) | 2003-10-10 |
| BR0208860A (pt) | 2004-10-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |