JP2007512318A - 白金（ｉｉ）錯体並びに該錯体の製法及び使用 - Google Patents
白金（ｉｉ）錯体並びに該錯体の製法及び使用 Download PDFInfo
- Publication number
- JP2007512318A JP2007512318A JP2006540664A JP2006540664A JP2007512318A JP 2007512318 A JP2007512318 A JP 2007512318A JP 2006540664 A JP2006540664 A JP 2006540664A JP 2006540664 A JP2006540664 A JP 2006540664A JP 2007512318 A JP2007512318 A JP 2007512318A
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- Prior art keywords
- platinum
- ligand
- compound
- oxalato
- complex
- 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
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- 238000000034 method Methods 0.000 title claims abstract description 88
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 239000003446 ligand Substances 0.000 claims abstract description 104
- 230000007935 neutral effect Effects 0.000 claims abstract description 47
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims abstract description 42
- 229960001756 oxaliplatin Drugs 0.000 claims abstract description 42
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- YXPVLVLKENHRSA-UHFFFAOYSA-N OC(=O)[Pt]C(O)=O Chemical compound OC(=O)[Pt]C(O)=O YXPVLVLKENHRSA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000001953 recrystallisation Methods 0.000 claims abstract description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- -1 heterocyclic amine Chemical class 0.000 claims description 47
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 30
- 239000012153 distilled water Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 19
- 238000001914 filtration Methods 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 17
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 150000003891 oxalate salts Chemical class 0.000 claims description 12
- 229910052711 selenium Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- LEJIGMDUKXBYCT-UHFFFAOYSA-N 2-(3-methylsulfanylbutan-2-yl)-1h-imidazole Chemical compound CSC(C)C(C)C1=NC=CN1 LEJIGMDUKXBYCT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052709 silver Inorganic materials 0.000 claims description 5
- 239000004332 silver Substances 0.000 claims description 5
- UJTDKNZVLGVLFT-UHFFFAOYSA-N 1,2-Bis(methylthio)ethane Chemical compound CSCCSC UJTDKNZVLGVLFT-UHFFFAOYSA-N 0.000 claims description 3
- NSOFFVNRVHFMCQ-UHFFFAOYSA-N 1-butyl-2-(methylsulfanylmethyl)imidazole Chemical compound CCCCN1C=CN=C1CSC NSOFFVNRVHFMCQ-UHFFFAOYSA-N 0.000 claims description 3
- ALKUAOHBBKTMKP-UHFFFAOYSA-N 1-methyl-2-(methylsulfanylmethyl)imidazole Chemical compound CSCC1=NC=CN1C ALKUAOHBBKTMKP-UHFFFAOYSA-N 0.000 claims description 3
- KKCQHAHBQUOKBU-UHFFFAOYSA-N 2-(1-methylsulfanylhexan-2-yl)-1h-imidazole Chemical compound CCCCC(CSC)C1=NC=CN1 KKCQHAHBQUOKBU-UHFFFAOYSA-N 0.000 claims description 3
- LJIZKCPUNGRRTP-UHFFFAOYSA-N 2-(1-methylsulfanylpropan-2-yl)-1h-imidazole Chemical compound CSCC(C)C1=NC=CN1 LJIZKCPUNGRRTP-UHFFFAOYSA-N 0.000 claims description 3
- JNGRYGVAABZSGA-UHFFFAOYSA-N 2-(2-methylsulfanylethyl)pyridine Chemical compound CSCCC1=CC=CC=N1 JNGRYGVAABZSGA-UHFFFAOYSA-N 0.000 claims description 3
- JAQGXZDFUNFLTD-UHFFFAOYSA-N 2-(2-methylsulfanylpropyl)pyridine Chemical compound CSC(C)CC1=CC=CC=N1 JAQGXZDFUNFLTD-UHFFFAOYSA-N 0.000 claims description 3
- KWXDPVBKJYKQIM-UHFFFAOYSA-N 2-(methylsulfanylmethyl)pyridine Chemical compound CSCC1=CC=CC=N1 KWXDPVBKJYKQIM-UHFFFAOYSA-N 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- CDTNFQWQDFAFSQ-UHFFFAOYSA-N 2-(1-methylsulfanylhexan-2-yl)-1H-imidazole platinum Chemical compound [Pt].C(CCC)C(CSC)C=1NC=CN1 CDTNFQWQDFAFSQ-UHFFFAOYSA-N 0.000 claims description 2
- LTCHTUOWTVGFGK-UHFFFAOYSA-N 2-(methylsulfanylmethyl)pyridine platinum Chemical compound [Pt].CSCc1ccccn1 LTCHTUOWTVGFGK-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- ATUUPSIOKNJNGB-UHFFFAOYSA-N [Pt].CC(C(C)SC)C=1NC=CN1 Chemical compound [Pt].CC(C(C)SC)C=1NC=CN1 ATUUPSIOKNJNGB-UHFFFAOYSA-N 0.000 claims description 2
- RVAWYMDSKYZYDP-UHFFFAOYSA-N [Pt].CC(CSC)C=1NC=CN1 Chemical compound [Pt].CC(CSC)C=1NC=CN1 RVAWYMDSKYZYDP-UHFFFAOYSA-N 0.000 claims description 2
- 239000013626 chemical specie Substances 0.000 claims description 2
- FPKPFCVTLLZLME-UHFFFAOYSA-N [Pt].CCCCn1ccnc1CSC Chemical compound [Pt].CCCCn1ccnc1CSC FPKPFCVTLLZLME-UHFFFAOYSA-N 0.000 claims 1
- YMHRZORRQZHHCV-UHFFFAOYSA-N [Pt].CSCc1nccn1C Chemical compound [Pt].CSCc1nccn1C YMHRZORRQZHHCV-UHFFFAOYSA-N 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 9
- 239000000243 solution Substances 0.000 description 41
- 239000000047 product Substances 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 239000002244 precipitate Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 241000894007 species Species 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000035484 reaction time Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 229940100890 silver compound Drugs 0.000 description 6
- 150000003379 silver compounds Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 230000001093 anti-cancer Effects 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 3
- 229960004316 cisplatin Drugs 0.000 description 3
- 239000008139 complexing agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 150000003058 platinum compounds Chemical group 0.000 description 3
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- SATAHIXXNMYTNF-UHFFFAOYSA-N [Pt+2].CC(C(C)SC)C=1NC=CN1 Chemical compound [Pt+2].CC(C(C)SC)C=1NC=CN1 SATAHIXXNMYTNF-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- QAWTYRYXDYHQNU-UHFFFAOYSA-N diazathiane Chemical compound NSN QAWTYRYXDYHQNU-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HNKLPNDFOVJIFG-UHFFFAOYSA-N oxalic acid;platinum Chemical compound [Pt].OC(=O)C(O)=O HNKLPNDFOVJIFG-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- NDBYXKQCPYUOMI-UHFFFAOYSA-N platinum(4+) Chemical compound [Pt+4] NDBYXKQCPYUOMI-UHFFFAOYSA-N 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- IJJMOFGFPMFIBN-UHFFFAOYSA-N 1-butyl-2-(methylsulfanylmethyl)imidazole platinum(2+) Chemical compound [Pt+2].C(CCC)N1C(=NC=C1)CSC IJJMOFGFPMFIBN-UHFFFAOYSA-N 0.000 description 1
- AJKNWAJLFKRVJN-UHFFFAOYSA-L 1-butyl-2-(methylsulfanylmethyl)imidazole;oxalate;platinum(2+) Chemical compound [Pt+2].[O-]C(=O)C([O-])=O.CCCCN1C=CN=C1CSC AJKNWAJLFKRVJN-UHFFFAOYSA-L 0.000 description 1
- HYZFYZRFTGGOEI-UHFFFAOYSA-N 2-(2-methylsulfanylpropyl)pyridine platinum Chemical compound [Pt].CSC(C)Cc1ccccn1 HYZFYZRFTGGOEI-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 240000007019 Oxalis corniculata Species 0.000 description 1
- 235000016499 Oxalis corniculata Nutrition 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
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- JPYNSHNIQUEPAB-UHFFFAOYSA-N [Pt+2].CSCC1=NC=CC=C1 Chemical compound [Pt+2].CSCC1=NC=CC=C1 JPYNSHNIQUEPAB-UHFFFAOYSA-N 0.000 description 1
- JLSCYFRQDZARHB-UHFFFAOYSA-N [Pt+2].CSCCC1=NC=CC=C1 Chemical compound [Pt+2].CSCCC1=NC=CC=C1 JLSCYFRQDZARHB-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- MUTQTHUBSRXFQO-UHFFFAOYSA-L oxalate;platinum(2+) Chemical compound [Pt+2].[O-]C(=O)C([O-])=O MUTQTHUBSRXFQO-UHFFFAOYSA-L 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52472703P | 2003-11-25 | 2003-11-25 | |
| PCT/IB2004/003855 WO2005051966A1 (en) | 2003-11-25 | 2004-11-24 | Platinum(ii) complexes, preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007512318A true JP2007512318A (ja) | 2007-05-17 |
| JP2007512318A5 JP2007512318A5 (https=) | 2007-12-20 |
Family
ID=34632925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006540664A Pending JP2007512318A (ja) | 2003-11-25 | 2004-11-24 | 白金（ｉｉ）錯体並びに該錯体の製法及び使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7576126B2 (https=) |
| EP (2) | EP1704156A1 (https=) |
| JP (1) | JP2007512318A (https=) |
| CA (1) | CA2547275A1 (https=) |
| WO (1) | WO2005051966A1 (https=) |
| ZA (1) | ZA200604529B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016500664A (ja) * | 2012-10-05 | 2016-01-14 | ヘレーウス プレシャス メタルズ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディートゲゼルシャフトＨｅｒａｅｕｓ Ｐｒｅｃｉｏｕｓ Ｍｅｔａｌｓ ＧｍｂＨ ＆ Ｃｏ． ＫＧ | 貴金属オキサラート錯体の製造方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1704156A1 (en) | 2003-11-25 | 2006-09-27 | Platco Technologies (Proprietary) Limited | Platinum(ii) complexes, preparation and use |
| NZ553044A (en) | 2004-09-01 | 2010-09-30 | Placto Technologies Proprietar | Preparations of platinum(II) complexes |
| WO2007021852A2 (en) * | 2005-08-11 | 2007-02-22 | Virginia Commonwealth University | Transplatinum complexes with n2o2 donor sets as cytotoxic and antitumor agents |
| RU2008135369A (ru) | 2006-01-30 | 2010-03-10 | Платко Текнолоджис (Проприэтэри) Лимитед (Za) | Получение комплексов платины(ii) |
| CN105218589A (zh) * | 2015-10-10 | 2016-01-06 | 山东铂源药业有限公司 | 一种奥沙利铂的合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5331648A (en) * | 1976-09-06 | 1978-03-25 | Yoshinori Yoshitani | Cissplatinum complex of 1*22diaminocyclohexane isomer |
| JPS59139360A (ja) * | 1983-01-21 | 1984-08-10 | Tanabe Seiyaku Co Ltd | 新規有機白金錯体及びその製法 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5896024A (ja) * | 1981-10-16 | 1983-06-07 | リチヤ−ド・エフ・ストツケル | 白金毒解毒剤 |
| KR840007599A (ko) * | 1983-01-21 | 1984-12-08 | 마쓰바라 이찌로오 | 백금 착화합 유기물의 제조방법 |
| GB2210039B (en) | 1987-09-24 | 1992-03-25 | Hanessian Dr Stephen | Cis-platinum derivatives |
| WO1989004318A1 (fr) | 1987-11-11 | 1989-05-18 | Toray Industries, Inc. | Complexe de platine et agent therapeutique contre les tumeurs malignes |
| US5281447A (en) * | 1991-10-25 | 1994-01-25 | International Business Machines Corporation | Patterned deposition of metals via photochemical decomposition of metal-oxalate complexes |
| JPH0776230B2 (ja) | 1992-01-13 | 1995-08-16 | 田中貴金属工業株式会社 | 白金化合物の製造方法 |
| JPH06287021A (ja) | 1992-04-22 | 1994-10-11 | Tanaka Kikinzoku Kogyo Kk | 光学活性な白金錯化合物の光学的分割方法 |
| JP2673331B2 (ja) * | 1993-01-12 | 1997-11-05 | 田中貴金属工業 株式会社 | 光学的に高純度なシス―オキザラート（トランス―１―１，２―シクロヘキサンジアミン）白金（▲ｉｉ▼） |
| JPH05301884A (ja) | 1992-04-22 | 1993-11-16 | Tanaka Kikinzoku Kogyo Kk | 白金錯化合物の製造方法 |
| US5402319A (en) * | 1993-04-22 | 1995-03-28 | Rockwell International Corporation | Avionics line replaceable unit with frameless spring ramp circuit card retainer |
| JP3025602B2 (ja) | 1993-05-21 | 2000-03-27 | デビオファーム エス．アー． | 光学的に高純度なシス−オキザラート（トランス−ｌ−１，２−シクロヘキサンジアミン）白金（ＩＩ）錯体の製造方法 |
| IL114852A (en) | 1994-08-08 | 2000-02-29 | Debiopharm Sa | Pharmaceutically stable preparation of oxaliplatinum |
| ES2206478T3 (es) | 1994-11-11 | 2004-05-16 | Debiopharm S.A. | Composiciones carcinostaticas que contienen cis-oxaliplatino y otra u otras sustancias carcinostaticas compatibles. |
| JPH09278785A (ja) | 1996-04-10 | 1997-10-28 | Tanaka Kikinzoku Kogyo Kk | 白金化合物の製造方法 |
| JP3154399B2 (ja) | 1996-07-04 | 2001-04-09 | デビオファーム エス．アー． | 白金化合物の製造方法 |
| DK0801070T3 (da) | 1996-04-10 | 2003-05-19 | Debiopharm Sa | Fremgangsmåde til fremstilling af platinforbindelse |
| GB9804013D0 (en) | 1998-02-25 | 1998-04-22 | Sanofi Sa | Formulations |
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- 2004-11-24 US US10/580,425 patent/US7576126B2/en not_active Expired - Fee Related
- 2004-11-24 CA CA002547275A patent/CA2547275A1/en not_active Abandoned
- 2004-11-24 ZA ZA200604529A patent/ZA200604529B/xx unknown
- 2004-11-24 JP JP2006540664A patent/JP2007512318A/ja active Pending
- 2004-11-24 EP EP10177033A patent/EP2330110A1/en not_active Withdrawn
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016500664A (ja) * | 2012-10-05 | 2016-01-14 | ヘレーウス プレシャス メタルズ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディートゲゼルシャフトＨｅｒａｅｕｓ Ｐｒｅｃｉｏｕｓ Ｍｅｔａｌｓ ＧｍｂＨ ＆ Ｃｏ． ＫＧ | 貴金属オキサラート錯体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20090312417A1 (en) | 2009-12-17 |
| EP1704156A1 (en) | 2006-09-27 |
| WO2005051966A1 (en) | 2005-06-09 |
| US7576126B2 (en) | 2009-08-18 |
| ZA200604529B (en) | 2007-12-27 |
| EP2330110A1 (en) | 2011-06-08 |
| US20070167643A1 (en) | 2007-07-19 |
| US7888390B2 (en) | 2011-02-15 |
| CA2547275A1 (en) | 2005-06-09 |
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