FI120493B - Parannuksia platinakomplekseihin - Google Patents
Parannuksia platinakomplekseihin Download PDFInfo
- Publication number
- FI120493B FI120493B FI960660A FI960660A FI120493B FI 120493 B FI120493 B FI 120493B FI 960660 A FI960660 A FI 960660A FI 960660 A FI960660 A FI 960660A FI 120493 B FI120493 B FI 120493B
- Authority
- FI
- Finland
- Prior art keywords
- amine
- platinum
- complex according
- group
- carboxylate
- Prior art date
Links
- 150000003057 platinum Chemical class 0.000 title abstract description 8
- -1 carbonate ester Chemical class 0.000 claims abstract description 27
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001412 amines Chemical class 0.000 claims abstract description 15
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 201000011510 cancer Diseases 0.000 claims abstract description 10
- 150000007942 carboxylates Chemical class 0.000 claims abstract description 9
- 108020004414 DNA Proteins 0.000 claims abstract description 7
- 125000004429 atom Chemical group 0.000 claims abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 5
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 3
- 102000053602 DNA Human genes 0.000 claims abstract description 3
- 210000004881 tumor cell Anatomy 0.000 claims abstract description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims abstract 2
- 239000000460 chlorine Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- BNZSQNHMCVRXBB-UHFFFAOYSA-N [Pt].CC1=NC=CC(=C1)C Chemical compound [Pt].CC1=NC=CC(=C1)C BNZSQNHMCVRXBB-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- OKJFNDYGMXIQPF-UHFFFAOYSA-N [Pt+4].CC1=NC=CC(=C1)C Chemical compound [Pt+4].CC1=NC=CC(=C1)C OKJFNDYGMXIQPF-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- IWBFMNLPFLCMBG-UHFFFAOYSA-N 2-methylpyridine;platinum Chemical compound [Pt].CC1=CC=CC=N1 IWBFMNLPFLCMBG-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- QCLRUNIZLOTOPA-UHFFFAOYSA-N [Pt].CC1=NC=CC(Cl)=C1Cl Chemical compound [Pt].CC1=NC=CC(Cl)=C1Cl QCLRUNIZLOTOPA-UHFFFAOYSA-N 0.000 claims 1
- LIPPGHVACMTZIG-UHFFFAOYSA-N [Pt].ClC1=C(C(=NC2=CC=CC=C12)C)Cl Chemical compound [Pt].ClC1=C(C(=NC2=CC=CC=C12)C)Cl LIPPGHVACMTZIG-UHFFFAOYSA-N 0.000 claims 1
- FATQPTDMVDYEQP-UHFFFAOYSA-N [Pt].ClC1=C(C(=NC=C1)C(C)C)Cl Chemical compound [Pt].ClC1=C(C(=NC=C1)C(C)C)Cl FATQPTDMVDYEQP-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 210000004027 cell Anatomy 0.000 abstract description 15
- 125000005843 halogen group Chemical group 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 2
- 230000031018 biological processes and functions Effects 0.000 abstract 1
- XKHCXFBIZREUJD-UHFFFAOYSA-N chloro hydrogen carbonate Chemical compound OC(=O)OCl XKHCXFBIZREUJD-UHFFFAOYSA-N 0.000 abstract 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 20
- 229960004316 cisplatin Drugs 0.000 description 20
- 230000000694 effects Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- HIWBPDCLEFXVKA-UHFFFAOYSA-L [Pt+2].CC1=NC=CC(=C1)C.C1(CCC1)(C(=O)[O-])C(=O)[O-] Chemical compound [Pt+2].CC1=NC=CC(=C1)C.C1(CCC1)(C(=O)[O-])C(=O)[O-] HIWBPDCLEFXVKA-UHFFFAOYSA-L 0.000 description 4
- GGGSPETTXZWRKS-UHFFFAOYSA-N [Pt].ClC=1C(=C(C(=NC1)C)Cl)C Chemical compound [Pt].ClC=1C(=C(C(=NC1)C)Cl)C GGGSPETTXZWRKS-UHFFFAOYSA-N 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- 230000001093 anti-cancer Effects 0.000 description 3
- 101710134784 Agnoprotein Proteins 0.000 description 2
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 2
- 108010082126 Alanine transaminase Proteins 0.000 description 2
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 2
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 190000008236 carboplatin complexes Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 231100000417 nephrotoxicity Toxicity 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- PFYPDUUXDADWKC-UHFFFAOYSA-N 2-propan-2-ylpyridine Chemical compound CC(C)C1=CC=CC=N1 PFYPDUUXDADWKC-UHFFFAOYSA-N 0.000 description 1
- RKTIAZVXWYFNJG-UHFFFAOYSA-N 3,4-dichloro-2-methylpyridine Chemical compound CC1=NC=CC(Cl)=C1Cl RKTIAZVXWYFNJG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000766026 Coregonus nasus Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229910019032 PtCl2 Inorganic materials 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
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- BPRUMWFDSCNJDH-UHFFFAOYSA-N [Pt+2].CC1=NC=CC(Cl)=C1Cl Chemical compound [Pt+2].CC1=NC=CC(Cl)=C1Cl BPRUMWFDSCNJDH-UHFFFAOYSA-N 0.000 description 1
- LBXFXAGRWJNJSX-UHFFFAOYSA-N [Pt+4].ClC=1C(=C(C(=NC1)C)Cl)C Chemical compound [Pt+4].ClC=1C(=C(C(=NC1)C)Cl)C LBXFXAGRWJNJSX-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000007052 brain toxicity Effects 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 231100000976 cerebrotoxicity Toxicity 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- CCQPAEQGAVNNIA-UHFFFAOYSA-L cyclobutane-1,1-dicarboxylate(2-) Chemical compound [O-]C(=O)C1(C([O-])=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-L 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000007682 dermal toxicity Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- YMIIPTKPOXUSSC-UHFFFAOYSA-L dipotassium;cyclobutane-1,1-dicarboxylate Chemical compound [K+].[K+].[O-]C(=O)C1(C([O-])=O)CCC1 YMIIPTKPOXUSSC-UHFFFAOYSA-L 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 231100000414 gastrointestinal toxicity Toxicity 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 208000016691 refractory malignant neoplasm Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 231100000438 skin toxicity Toxicity 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 231100000974 spleenotoxicity Toxicity 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Materials For Photolithography (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Studio Devices (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9502799 | 1995-02-14 | ||
| GBGB9502799.1A GB9502799D0 (en) | 1995-02-14 | 1995-02-14 | Improvements in platinum complexes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI960660A0 FI960660A0 (fi) | 1996-02-14 |
| FI960660A FI960660A (fi) | 1996-08-15 |
| FI120493B true FI120493B (fi) | 2009-11-13 |
Family
ID=10769529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI960660A FI120493B (fi) | 1995-02-14 | 1996-02-14 | Parannuksia platinakomplekseihin |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US5665771A (ja) |
| EP (1) | EP0727430B1 (ja) |
| JP (1) | JP3219235B2 (ja) |
| KR (1) | KR100339866B1 (ja) |
| AT (1) | ATE202111T1 (ja) |
| AU (1) | AU707814B2 (ja) |
| CA (1) | CA2169019C (ja) |
| DE (1) | DE69613254T2 (ja) |
| DK (1) | DK0727430T3 (ja) |
| ES (1) | ES2157399T3 (ja) |
| FI (1) | FI120493B (ja) |
| GB (1) | GB9502799D0 (ja) |
| GR (1) | GR3036513T3 (ja) |
| HK (1) | HK1011997A1 (ja) |
| NO (1) | NO307569B1 (ja) |
| NZ (1) | NZ280946A (ja) |
| PT (1) | PT727430E (ja) |
| TW (1) | TW432068B (ja) |
| ZA (1) | ZA96885B (ja) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6001872A (en) * | 1999-03-05 | 1999-12-14 | Virginia Commonwealth University | Water soluble transplatinum complexes with anti-cancer activity and method of using same |
| WO2000061590A1 (en) * | 1999-04-13 | 2000-10-19 | Anormed, Inc. | Process for preparing amine platinum complexes |
| US6413953B1 (en) * | 1999-04-13 | 2002-07-02 | Anormed Inc. | Pt(IV) antitumor agent |
| CA2385528C (en) | 1999-10-01 | 2013-12-10 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| AUPQ641100A0 (en) * | 2000-03-23 | 2000-04-15 | Australia Nuclear Science & Technology Organisation | Methods of synthesis and use of radiolabelled platinum chemotherapeutic ag ents |
| GB0011903D0 (en) * | 2000-05-18 | 2000-07-05 | Astrazeneca Ab | Combination chemotherapy |
| US6894049B1 (en) * | 2000-10-04 | 2005-05-17 | Anormed, Inc. | Platinum complexes as antitumor agents |
| DE60235375D1 (de) * | 2001-08-23 | 2010-04-01 | Yissum Res Dev Co | Platinkomplexe und deren verwendung in der therapie |
| US8324197B2 (en) * | 2005-08-11 | 2012-12-04 | Virginia Commonwealth University | Transplatinum complexes with N2O2 donor sets as cytotoxic and antitumor agents |
| US8178564B2 (en) * | 2006-11-06 | 2012-05-15 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8168661B2 (en) * | 2006-11-06 | 2012-05-01 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8168662B1 (en) | 2006-11-06 | 2012-05-01 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
| US8173686B2 (en) * | 2006-11-06 | 2012-05-08 | Poniard Pharmaceuticals, Inc. | Use of picoplatin to treat colorectal cancer |
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| US20110033528A1 (en) * | 2009-08-05 | 2011-02-10 | Poniard Pharmaceuticals, Inc. | Stabilized picoplatin oral dosage form |
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| CN101809024A (zh) * | 2007-07-16 | 2010-08-18 | 铂雅制药公司 | 吡铂的口服制剂 |
| US20110053879A1 (en) * | 2008-02-08 | 2011-03-03 | Poniard Pharmaceuticals, Inc. | Picoplatin and amrubicin to treat lung cancer |
| CN101775040B (zh) * | 2009-12-31 | 2012-05-09 | 南京臣功制药有限公司 | 吡铂的制备方法 |
| WO2015009841A2 (en) * | 2013-07-16 | 2015-01-22 | Blend Therapeutics | Platinum compounds having a heterocycle ligand, nanoparticles, and uses thereof |
| CN106943343B (zh) * | 2016-01-06 | 2020-05-12 | 山东新时代药业有限公司 | 一种甲啶铂注射液及其制备方法 |
| US10987353B2 (en) | 2016-05-04 | 2021-04-27 | The Wistar Institute Of Anatomy And Biology | Methods of treating cancers overexpressing CARM1 with EZH2 inhibitors and platinum-based antineoplastic drugs |
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| GB1432562A (en) | 1972-04-10 | 1976-04-22 | Rustenburg Platinum Mines Ltd | Platinum co-ordination compounds |
| KR840007599A (ko) * | 1983-01-21 | 1984-12-08 | 마쓰바라 이찌로오 | 백금 착화합 유기물의 제조방법 |
| US4533502A (en) * | 1983-02-22 | 1985-08-06 | Rochon Fernande D | Platinum (II) compounds and their preparation |
| EP0167310B1 (en) * | 1984-06-27 | 1991-05-29 | Johnson Matthey Public Limited Company | Platinum co-ordination compounds |
| JPS61238795A (ja) * | 1985-04-16 | 1986-10-24 | エンゲルハード・コーポレーシヨン | 白金トリアミン抗腫瘍剤 |
| US4902797A (en) * | 1986-12-18 | 1990-02-20 | Shionogi & Co., Ltd. | Ammine-alicyclic amine-platinum complexes and antitumor agents |
| US4812193A (en) * | 1986-12-22 | 1989-03-14 | Gauron Richard F | Inset panel fastener and method of using |
| EP0328274B1 (en) * | 1988-02-02 | 1994-10-19 | Johnson Matthey, Inc., | Pt (IV) complexes |
| GB8806044D0 (en) * | 1988-03-14 | 1988-04-13 | Johnson Matthey Plc | Platinum coordination compounds |
| GB9105037D0 (en) * | 1991-03-09 | 1991-04-24 | Johnson Matthey Plc | Improvements in chemical compounds |
| US5624919A (en) * | 1993-09-14 | 1997-04-29 | The University Of Vermont And State Agricultural College | Trans platinum (IV) complexes |
| GB9408218D0 (en) * | 1994-04-26 | 1994-06-15 | Johnson Matthey Plc | Improvements in platinum complexes |
| WO2000061590A1 (en) * | 1999-04-13 | 2000-10-19 | Anormed, Inc. | Process for preparing amine platinum complexes |
| DE60235375D1 (de) * | 2001-08-23 | 2010-04-01 | Yissum Res Dev Co | Platinkomplexe und deren verwendung in der therapie |
| WO2006024897A1 (en) * | 2004-09-01 | 2006-03-09 | Platco Technologies (Proprietary) Limited | Preparation of platinum(ii) complexes |
| US8324197B2 (en) * | 2005-08-11 | 2012-12-04 | Virginia Commonwealth University | Transplatinum complexes with N2O2 donor sets as cytotoxic and antitumor agents |
-
1995
- 1995-02-14 GB GBGB9502799.1A patent/GB9502799D0/en active Pending
-
1996
- 1996-01-29 ES ES96300601T patent/ES2157399T3/es not_active Expired - Lifetime
- 1996-01-29 DE DE69613254T patent/DE69613254T2/de not_active Expired - Lifetime
- 1996-01-29 PT PT96300601T patent/PT727430E/pt unknown
- 1996-01-29 DK DK96300601T patent/DK0727430T3/da active
- 1996-01-29 AT AT96300601T patent/ATE202111T1/de active
- 1996-01-29 EP EP96300601A patent/EP0727430B1/en not_active Expired - Lifetime
- 1996-01-31 AU AU42258/96A patent/AU707814B2/en not_active Expired
- 1996-02-05 ZA ZA96885A patent/ZA96885B/xx unknown
- 1996-02-07 NZ NZ280946A patent/NZ280946A/en not_active IP Right Cessation
- 1996-02-07 TW TW085101525A patent/TW432068B/zh not_active IP Right Cessation
- 1996-02-07 CA CA002169019A patent/CA2169019C/en not_active Expired - Lifetime
- 1996-02-07 US US08/597,953 patent/US5665771A/en not_active Ceased
- 1996-02-12 KR KR1019960003292A patent/KR100339866B1/ko not_active IP Right Cessation
- 1996-02-13 NO NO960569A patent/NO307569B1/no not_active IP Right Cessation
- 1996-02-14 FI FI960660A patent/FI120493B/fi not_active IP Right Cessation
- 1996-02-14 JP JP02693596A patent/JP3219235B2/ja not_active Expired - Lifetime
-
1998
- 1998-12-10 HK HK98113066A patent/HK1011997A1/xx not_active IP Right Cessation
-
2001
- 2001-09-04 GR GR20010401373T patent/GR3036513T3/el unknown
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2009
- 2009-05-08 US US12/437,889 patent/USRE41209E1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NZ280946A (en) | 1997-05-26 |
| ATE202111T1 (de) | 2001-06-15 |
| EP0727430A1 (en) | 1996-08-21 |
| JPH08259581A (ja) | 1996-10-08 |
| KR100339866B1 (ko) | 2002-11-07 |
| EP0727430B1 (en) | 2001-06-13 |
| FI960660A0 (fi) | 1996-02-14 |
| DE69613254D1 (de) | 2001-07-19 |
| ZA96885B (en) | 1996-08-14 |
| DE69613254T2 (de) | 2001-09-20 |
| NO307569B1 (no) | 2000-04-25 |
| HK1011997A1 (en) | 1999-07-23 |
| CA2169019A1 (en) | 1996-08-15 |
| AU4225896A (en) | 1996-08-22 |
| DK0727430T3 (da) | 2001-09-03 |
| USRE41209E1 (en) | 2010-04-06 |
| ES2157399T3 (es) | 2001-08-16 |
| NO960569L (no) | 1996-08-15 |
| US5665771A (en) | 1997-09-09 |
| AU707814B2 (en) | 1999-07-22 |
| GB9502799D0 (en) | 1995-04-05 |
| TW432068B (en) | 2001-05-01 |
| FI960660A (fi) | 1996-08-15 |
| GR3036513T3 (en) | 2001-12-31 |
| KR960030940A (ko) | 1996-09-17 |
| PT727430E (pt) | 2001-11-30 |
| NO960569D0 (no) | 1996-02-13 |
| CA2169019C (en) | 2003-02-04 |
| JP3219235B2 (ja) | 2001-10-15 |
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