TWI332834B - - Google Patents
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- Publication number
- TWI332834B TWI332834B TW093106868A TW93106868A TWI332834B TW I332834 B TWI332834 B TW I332834B TW 093106868 A TW093106868 A TW 093106868A TW 93106868 A TW93106868 A TW 93106868A TW I332834 B TWI332834 B TW I332834B
- Authority
- TW
- Taiwan
- Prior art keywords
- antitumor agent
- sma
- month
- pirarubicin
- maleic acid
- Prior art date
Links
- 239000000693 micelle Substances 0.000 claims description 44
- 239000002246 antineoplastic agent Substances 0.000 claims description 20
- 229960004316 cisplatin Drugs 0.000 claims description 18
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 13
- 229920000642 polymer Polymers 0.000 claims description 10
- 229940045799 anthracyclines and related substance Drugs 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 150000001718 carbodiimides Chemical class 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
- 230000007935 neutral effect Effects 0.000 claims 1
- 238000000926 separation method Methods 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
- 229960001221 pirarubicin Drugs 0.000 description 36
- 206010028980 Neoplasm Diseases 0.000 description 28
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 25
- KMSKQZKKOZQFFG-YXRRJAAWSA-N (7S,9S)-7-[[(2R,4S,5S,6S)-4-amino-6-methyl-5-[[(2R)-2-oxanyl]oxy]-2-oxanyl]oxy]-6,9,11-trihydroxy-9-(2-hydroxy-1-oxoethyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione Chemical compound O([C@H]1[C@@H](N)C[C@@H](O[C@H]1C)O[C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@@H]1CCCCO1 KMSKQZKKOZQFFG-YXRRJAAWSA-N 0.000 description 24
- 241000699670 Mus sp. Species 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 229960001592 paclitaxel Drugs 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 14
- 229960004679 doxorubicin Drugs 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 11
- 210000001519 tissue Anatomy 0.000 description 10
- 229940079593 drug Drugs 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- 229930012538 Paclitaxel Natural products 0.000 description 8
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 8
- 241000699666 Mus <mouse, genus> Species 0.000 description 7
- 230000000259 anti-tumor effect Effects 0.000 description 7
- 201000011510 cancer Diseases 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 6
- 230000001472 cytotoxic effect Effects 0.000 description 5
- 238000010253 intravenous injection Methods 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 231100000433 cytotoxic Toxicity 0.000 description 4
- 230000003013 cytotoxicity Effects 0.000 description 4
- 231100000135 cytotoxicity Toxicity 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 210000002216 heart Anatomy 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 230000037396 body weight Effects 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 2
- 108010082126 Alanine transaminase Proteins 0.000 description 2
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 2
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- 229940009456 adriamycin Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003817 anthracycline antibiotic agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000000601 blood cell Anatomy 0.000 description 2
- 238000004820 blood count Methods 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 206010001167 Adenocarcinoma of colon Diseases 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 230000002112 DNA intercalation Effects 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 101710183280 Topoisomerase Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- -1 adriamycin compound Chemical class 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 210000002798 bone marrow cell Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000022534 cell killing Effects 0.000 description 1
- 201000010897 colon adenocarcinoma Diseases 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- KOWWOODYPWDWOJ-LVBPXUMQSA-N elatine Chemical compound C([C@]12CN(C3[C@@]45OCO[C@]44[C@H]6[C@@H](OC)[C@@H]([C@H](C4)OC)C[C@H]6[C@@]3([C@@H]1[C@@H]5OC)[C@@H](OC)CC2)CC)OC(=O)C1=CC=CC=C1N1C(=O)CC(C)C1=O KOWWOODYPWDWOJ-LVBPXUMQSA-N 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000001641 gel filtration chromatography Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 231100000226 haematotoxicity Toxicity 0.000 description 1
- 210000002064 heart cell Anatomy 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 238000007490 hematoxylin and eosin (H&E) staining Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000003292 kidney cell Anatomy 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ADAMEOZKZQRNKP-UHFFFAOYSA-N n'-propylmethanediimine Chemical compound CCCN=C=N ADAMEOZKZQRNKP-UHFFFAOYSA-N 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000011800 void material 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/243—Platinum; Compounds 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6905—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion
- A61K47/6907—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a colloid or an emulsion the form being a microemulsion, nanoemulsion or micelle
-
- 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)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nanotechnology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003147852 | 2003-05-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200505414A TW200505414A (en) | 2005-02-16 |
| TWI332834B true TWI332834B (enExample) | 2010-11-11 |
Family
ID=33475378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093106868A TW200505414A (en) | 2003-05-26 | 2004-03-15 | Anti-tumor agent and process for producing the same |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7682630B2 (enExample) |
| EP (1) | EP1627645B1 (enExample) |
| JP (1) | JP4669393B2 (enExample) |
| CN (1) | CN1697663A (enExample) |
| AU (1) | AU2004241830B9 (enExample) |
| CA (1) | CA2489259C (enExample) |
| ES (1) | ES2642179T3 (enExample) |
| HU (1) | HUE035003T2 (enExample) |
| PT (1) | PT1627645T (enExample) |
| TW (1) | TW200505414A (enExample) |
| WO (1) | WO2004103409A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2006238072A1 (en) * | 2005-04-18 | 2006-10-26 | Hiroshi Maeda | Polymeric pharmaceutical agent for treatment of cancer and process for production of the same |
| EP1926492B1 (en) * | 2005-09-12 | 2010-10-13 | BENDALE. N, Yogesh | Novel bio platinum, process for preparation, method of administration for anti-tumour treatment |
| FR2922452B1 (fr) * | 2007-10-19 | 2010-01-22 | Coatex Sas | Formulations de composes organoplatiniques en presence de polymeres associatifs, produits obtenus et leurs utilisations |
| JP2010013411A (ja) * | 2008-07-05 | 2010-01-21 | Hiroshi Maeda | 抗炎症剤 |
| ES2627026T3 (es) | 2011-09-05 | 2017-07-26 | Hiroshi Maeda | Sonda molecular fluorescente de tipo polímero |
| JP6083738B2 (ja) * | 2013-03-06 | 2017-02-22 | 公立大学法人大阪市立大学 | ホウ素中性子捕捉療法用組成物およびその製造方法 |
| WO2015088990A1 (en) | 2013-12-09 | 2015-06-18 | Durect Corporation | Pharmaceutically active agent complexes, polymer complexes, and compositions and methods involving the same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3367921D1 (en) * | 1982-02-27 | 1987-01-15 | Kuraray Co | Neocarzinostatin complexes, a method for producing the same, and an antitumor agent containing said complexes as an active component |
| JPS58149903A (ja) * | 1982-02-27 | 1983-09-06 | Kuraray Co Ltd | ネオカルチノスタチン複合体の製造法 |
| JPS6075499A (ja) * | 1983-08-08 | 1985-04-27 | Kuraray Co Ltd | ネオカルチノスタチン誘導体及びその製造法 |
| JP2556865B2 (ja) * | 1986-09-19 | 1996-11-27 | 山之内製薬株式会社 | ネオカルチノスタチン誘導体の非注射投与用組成物 |
| US5281710A (en) * | 1990-08-01 | 1994-01-25 | The Scripps Research Institute | Dynemicin analogs: synthesis, methods of preparation and use |
| EP0914116B1 (en) * | 1996-05-22 | 2000-10-11 | Protarga Inc. | Compositions comprising conjugates of cis-docosahexaenoic acid and taxotere |
| GB0001481D0 (en) * | 2000-01-21 | 2000-03-15 | Theryte Ltd | System for delivering a medicament |
| KR100446101B1 (ko) | 2000-12-07 | 2004-08-30 | 주식회사 삼양사 | 수난용성 약물의 서방성 제형 조성물 |
-
2004
- 2004-02-02 ES ES04707295.4T patent/ES2642179T3/es not_active Expired - Lifetime
- 2004-02-02 AU AU2004241830A patent/AU2004241830B9/en not_active Expired
- 2004-02-02 CN CNA2004800006708A patent/CN1697663A/zh active Pending
- 2004-02-02 PT PT47072954T patent/PT1627645T/pt unknown
- 2004-02-02 HU HUE04707295A patent/HUE035003T2/en unknown
- 2004-02-02 WO PCT/JP2004/000993 patent/WO2004103409A1/ja not_active Ceased
- 2004-02-02 EP EP04707295.4A patent/EP1627645B1/en not_active Expired - Lifetime
- 2004-02-02 CA CA2489259A patent/CA2489259C/en not_active Expired - Fee Related
- 2004-02-02 US US10/514,892 patent/US7682630B2/en not_active Expired - Fee Related
- 2004-02-02 JP JP2005506303A patent/JP4669393B2/ja not_active Expired - Fee Related
- 2004-03-15 TW TW093106868A patent/TW200505414A/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2489259C (en) | 2011-08-30 |
| JP4669393B2 (ja) | 2011-04-13 |
| CN1697663A (zh) | 2005-11-16 |
| WO2004103409A1 (ja) | 2004-12-02 |
| EP1627645A4 (en) | 2008-12-24 |
| TW200505414A (en) | 2005-02-16 |
| ES2642179T3 (es) | 2017-11-15 |
| AU2004241830B9 (en) | 2010-04-22 |
| JPWO2004103409A1 (ja) | 2006-07-20 |
| US7682630B2 (en) | 2010-03-23 |
| EP1627645B1 (en) | 2017-08-23 |
| AU2004241830B2 (en) | 2010-02-25 |
| HUE035003T2 (en) | 2018-05-02 |
| EP1627645A1 (en) | 2006-02-22 |
| US20050208136A1 (en) | 2005-09-22 |
| PT1627645T (pt) | 2017-11-23 |
| AU2004241830A1 (en) | 2004-12-02 |
| CA2489259A1 (en) | 2004-12-02 |
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