JPS637194B2 - - Google Patents
Info
- Publication number
- JPS637194B2 JPS637194B2 JP56009463A JP946381A JPS637194B2 JP S637194 B2 JPS637194 B2 JP S637194B2 JP 56009463 A JP56009463 A JP 56009463A JP 946381 A JP946381 A JP 946381A JP S637194 B2 JPS637194 B2 JP S637194B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- water
- platinum
- oco
- formula
- 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.)
- Expired
Links
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 58
- 229910052697 platinum Inorganic materials 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 239000003814 drug Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 229940079593 drug Drugs 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 229940125904 compound 1 Drugs 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 230000004083 survival effect Effects 0.000 description 8
- 206010028980 Neoplasm Diseases 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 231100000111 LD50 Toxicity 0.000 description 6
- 230000000259 anti-tumor effect Effects 0.000 description 6
- 239000012155 injection solvent Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- -1 alkali metal salt Chemical class 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 210000002700 urine Anatomy 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 4
- 229960004316 cisplatin Drugs 0.000 description 4
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 206010003445 Ascites Diseases 0.000 description 3
- 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 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229940090044 injection Drugs 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 208000001382 Experimental Melanoma Diseases 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 206010029155 Nephropathy toxic Diseases 0.000 description 2
- 208000006268 Sarcoma 180 Diseases 0.000 description 2
- WNFHGZLVUQBPMA-JSCKKFHOSA-M Sodium glucuronate Chemical compound [Na+].O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C([O-])=O WNFHGZLVUQBPMA-JSCKKFHOSA-M 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- UOHYCYGTFKYJSP-UHFFFAOYSA-N azane;platinum(2+);dinitrate Chemical compound N.N.[Pt+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UOHYCYGTFKYJSP-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 229940109239 creatinine Drugs 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 230000007694 nephrotoxicity Effects 0.000 description 2
- 231100000417 nephrotoxicity Toxicity 0.000 description 2
- 150000003057 platinum Chemical class 0.000 description 2
- 150000003058 platinum compounds Chemical class 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000176 sodium gluconate Substances 0.000 description 2
- 235000012207 sodium gluconate Nutrition 0.000 description 2
- 229940005574 sodium gluconate Drugs 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- 239000011345 viscous material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000725101 Clea Species 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 description 1
- 208000007093 Leukemia L1210 Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZSWVADAIGMSQBB-UHFFFAOYSA-L cyclobutane-1,1-dicarboxylate;platinum(2+) Chemical compound [Pt+2].[O-]C(=O)C1(C([O-])=O)CCC1 ZSWVADAIGMSQBB-UHFFFAOYSA-L 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- POQBJIOLWPDPJE-UHFFFAOYSA-N cyclohexane-1,2-diamine;platinum Chemical compound [Pt].NC1CCCCC1N POQBJIOLWPDPJE-UHFFFAOYSA-N 0.000 description 1
- FHPKJGBPTSBFEW-UHFFFAOYSA-L cyclohexane-1,2-diamine;platinum(2+);sulfate Chemical compound [Pt+2].[O-]S([O-])(=O)=O.NC1CCCCC1N FHPKJGBPTSBFEW-UHFFFAOYSA-L 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- RGEUJMSAPBESFR-UHFFFAOYSA-L disodium hydrogen phosphate tetrahydrate Chemical compound O.O.O.O.[Na+].[Na+].OP([O-])([O-])=O RGEUJMSAPBESFR-UHFFFAOYSA-L 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229940093181 glucose injection Drugs 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000008816 organ damage Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QMYDVDBERNLWKB-UHFFFAOYSA-N propane-1,2-diol;hydrate Chemical compound O.CC(O)CO QMYDVDBERNLWKB-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940048084 pyrophosphate Drugs 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229940023144 sodium glycolate Drugs 0.000 description 1
- SQMCFUSVGSBKFK-UHFFFAOYSA-M sodium;5-(cyclohexen-1-yl)-1,5-dimethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].O=C1N(C)C(=O)[N-]C(=O)C1(C)C1=CCCCC1 SQMCFUSVGSBKFK-UHFFFAOYSA-M 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56009463A JPS57123198A (en) | 1981-01-23 | 1981-01-23 | Novel platinum complex |
| EP82200020A EP0057023B1 (en) | 1981-01-23 | 1982-01-07 | Novel platinum complexes |
| DE8282200020T DE3260164D1 (en) | 1981-01-23 | 1982-01-07 | Novel platinum complexes |
| CA000394370A CA1180009A (en) | 1981-01-23 | 1982-01-18 | Platinum complexes |
| GB8201616A GB2091731B (en) | 1981-01-23 | 1982-01-20 | Platinum complexes |
| AU79765/82A AU557336B2 (en) | 1981-01-23 | 1982-01-22 | Diammine platinum complexes with sugars and polyhydroxy- carboxylic acids |
| US06/485,584 US4575550A (en) | 1981-01-23 | 1983-04-14 | Platinum complexes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56009463A JPS57123198A (en) | 1981-01-23 | 1981-01-23 | Novel platinum complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57123198A JPS57123198A (en) | 1982-07-31 |
| JPS637194B2 true JPS637194B2 (US20080094685A1-20080424-C00004.png) | 1988-02-15 |
Family
ID=11720966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56009463A Granted JPS57123198A (en) | 1981-01-23 | 1981-01-23 | Novel platinum complex |
Country Status (7)
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5921697A (ja) * | 1982-06-24 | 1984-02-03 | Yoshinori Kitani | 新規な白金錯体 |
| JPS59222498A (ja) * | 1983-06-01 | 1984-12-14 | Shionogi & Co Ltd | 新規グリコ−ル酸系白金錯体および抗悪性腫瘍剤 |
| US4562275A (en) * | 1984-03-23 | 1985-12-31 | Bristol-Myers Co. | Antitumor platinum complexes |
| JPS617283A (ja) * | 1984-06-20 | 1986-01-13 | Shionogi & Co Ltd | 新規白金錯体および抗悪性腫瘍剤 |
| IL76889A0 (en) * | 1984-11-02 | 1986-02-28 | Johnson Matthey Plc | Solubilised platinum compound,method for the production thereof and pharmaceutical compositions containing the same |
| NZ214504A (en) * | 1984-12-17 | 1988-07-28 | American Cyanamid Co | Platinum/saccharide complexes and pharmaceutical compositions |
| JPS6296A (ja) * | 1985-03-06 | 1987-01-06 | Sumitomo Pharmaceut Co Ltd | 脂溶性白金（２）錯体 |
| JPH0665648B2 (ja) * | 1985-09-25 | 1994-08-24 | 塩野義製薬株式会社 | 白金系抗癌物質の安定な凍結真空乾燥製剤 |
| EP0270682A4 (en) * | 1986-05-21 | 1989-04-12 | Kuraray Co | NEW COMPLEXES, PROCESS FOR THEIR PREPARATION, AND THEIR MEDICINAL USE. |
| US5011959A (en) * | 1986-11-17 | 1991-04-30 | The Board Of Regents, The University Of Texas System | 1,2-diaminocyclohexane-platinum complexes with antitumor activity |
| ATE73814T1 (de) * | 1986-12-18 | 1992-04-15 | Shionogi & Co | Ammine-n-heterocyclische platinkomplexe und antitumormittel. |
| US4895935A (en) * | 1987-07-17 | 1990-01-23 | Georgetown University | Platinum pharmaceuticals |
| US4895936A (en) * | 1987-07-17 | 1990-01-23 | Georgetown University | Platinum pharmaceuticals |
| US4956459A (en) * | 1987-07-17 | 1990-09-11 | Georgetown University | Platinum compounds suitable for use as pharmaceuticals |
| DE3879709T2 (de) * | 1987-07-17 | 1993-10-07 | Georgetown University Washingt | Platin-arzneimittel. |
| JPH01294683A (ja) * | 1988-02-04 | 1989-11-28 | Kanebo Ltd | 新規白金錯体および該化合物を有効成分とする抗腫瘍剤並びに該化合物製造用中間体 |
| WO1990003402A1 (en) * | 1988-09-27 | 1990-04-05 | Kuraray Co., Ltd. | Novel composite, process for its preparation and medicinal use thereof |
| US5393909A (en) * | 1988-11-22 | 1995-02-28 | Board Of Regents, The University Of Texas System | Diamine platinum complexes as antitumor agents |
| US4946954A (en) * | 1989-01-17 | 1990-08-07 | Georgetown University | Platinum pharmaceutical agents |
| US5130450A (en) * | 1990-04-25 | 1992-07-14 | Nippon Kayaku Kabushiki Kaisha | Platinum complexes |
| EP2266607A3 (en) | 1999-10-01 | 2011-04-20 | Immunogen, Inc. | Immunoconjugates for treating cancer |
| US20100034874A1 (en) * | 2006-12-08 | 2010-02-11 | Katayama Chemical Industries Co., Ltd. | Liposome encapsulating ammine-platinum complex at high concentration, and method for production of the liposome |
| CN100500682C (zh) * | 2007-02-14 | 2009-06-17 | 江苏奥赛康药业有限公司 | 一种奈达铂的提纯方法 |
| CN101402655B (zh) * | 2008-11-07 | 2011-06-15 | 江苏奥赛康药业有限公司 | 一种米铂的制备方法 |
| CN102417522B (zh) * | 2011-10-20 | 2014-11-26 | 南京工业大学 | 一种奈达铂的制备方法 |
| CN105399777A (zh) * | 2015-11-23 | 2016-03-16 | 南京先声东元制药有限公司 | 一种奈达铂类似物及其制备方法 |
| CN105622673B (zh) * | 2016-01-25 | 2018-11-06 | 南开大学 | 具有抗癌活性的糖基化四价铂类化合物、制备方法及应用 |
| CN112225757B (zh) * | 2020-09-17 | 2023-07-21 | 昆明贵研药业有限公司 | 一种洛铂三水合物的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4115418A (en) * | 1976-09-02 | 1978-09-19 | Government Of The United States Of America | 1,2-diaminocyclohexane platinum (ii) complexes having antineoplastic activity |
| US4140707A (en) * | 1972-06-08 | 1979-02-20 | Research Corporation | Malonato platinum anti-tumor compounds |
| JPS55120594A (en) * | 1979-03-07 | 1980-09-17 | Engelhard Min & Chem | Ethylene diamine platinum*ii* and 1*22diaminoocyclohexane platinum*ii* pyrophosphate complex |
| JPS55160787A (en) * | 1979-03-07 | 1980-12-13 | Engelhard Min & Chem | Cissdiammineplatinum*ii*orthophosphate complex |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS5829957B2 (ja) * | 1977-09-12 | 1983-06-25 | 喜徳 喜谷 | 新規な白金錯体 |
| SE447902B (sv) * | 1977-10-19 | 1986-12-22 | Johnson Matthey Co Ltd | Cis-koordinationsforening av platina och komposition innehallande foreningen |
| DE2845371A1 (de) * | 1977-10-19 | 1979-04-26 | Johnson Matthey Co Ltd | Platinkomplexverbindung, pharmazeutische stoffzusammensetzung mit einer solchen verbindung und deren anwendung |
| US4291023A (en) * | 1979-03-07 | 1981-09-22 | Engelhard Minerals & Chemicals Corp. | Method for treating tumors using cis-diammineplatinum (II) organophosphate complexes |
| US4234499A (en) * | 1979-03-07 | 1980-11-18 | Engelhard Minerals & Chemicals Corporation | Cis-diammireplatinum(II) organophosphate complexes |
| US4271085A (en) * | 1979-06-20 | 1981-06-02 | Engelhard Minerals & Chemicals Corporation | Cis-platinum (II) amine lactate complexes |
| US4322362A (en) * | 1980-07-28 | 1982-03-30 | Bristol-Myers Company | Salts of 2-hydroxymalonate platinum complexes |
-
1981
- 1981-01-23 JP JP56009463A patent/JPS57123198A/ja active Granted
-
1982
- 1982-01-07 EP EP82200020A patent/EP0057023B1/en not_active Expired
- 1982-01-07 DE DE8282200020T patent/DE3260164D1/de not_active Expired
- 1982-01-18 CA CA000394370A patent/CA1180009A/en not_active Expired
- 1982-01-20 GB GB8201616A patent/GB2091731B/en not_active Expired
- 1982-01-22 AU AU79765/82A patent/AU557336B2/en not_active Expired
-
1983
- 1983-04-14 US US06/485,584 patent/US4575550A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4140707A (en) * | 1972-06-08 | 1979-02-20 | Research Corporation | Malonato platinum anti-tumor compounds |
| US4140707B1 (US20080094685A1-20080424-C00004.png) * | 1972-06-08 | 1989-12-19 | ||
| US4115418A (en) * | 1976-09-02 | 1978-09-19 | Government Of The United States Of America | 1,2-diaminocyclohexane platinum (ii) complexes having antineoplastic activity |
| JPS55120594A (en) * | 1979-03-07 | 1980-09-17 | Engelhard Min & Chem | Ethylene diamine platinum*ii* and 1*22diaminoocyclohexane platinum*ii* pyrophosphate complex |
| JPS55160787A (en) * | 1979-03-07 | 1980-12-13 | Engelhard Min & Chem | Cissdiammineplatinum*ii*orthophosphate complex |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1180009A (en) | 1984-12-27 |
| DE3260164D1 (en) | 1984-06-28 |
| JPS57123198A (en) | 1982-07-31 |
| EP0057023B1 (en) | 1984-05-23 |
| US4575550A (en) | 1986-03-11 |
| AU557336B2 (en) | 1986-12-18 |
| AU7976582A (en) | 1982-07-29 |
| GB2091731A (en) | 1982-08-04 |
| GB2091731B (en) | 1985-01-30 |
| EP0057023A1 (en) | 1982-08-04 |
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