FI120493B - Förbättringar i platinakomplexer - Google Patents
Förbättringar i platinakomplexer 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
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- 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)
Claims (16)
1. Cis-platinakomplex med den allmänna formeln la eller lb, 5 B X A X\ I /A NSsp^/,/,, la Pt ® Z^ Να Ζ^Ί A B kännetecknat av att var och en grupp A är en avlägsnande grupp, som kan vara en lika eller olik grupp, eller grupperna A bil-10 dar tillsammans tvätandat karboxylat eller sulfat, var och en grupp B, som kan vara en lika eller olik grupp, är halogen, hydroxi, karboxylat, karbamat eller karbonatester, Z är substituerat amin, väri substituenten för-15 hindrar steriskt Pt-atomens ätkomst till en tumörcells DNA-sträng, varvid Z är ett omättat cykliskt amin, som är förenat med Pt via aminets kväveatom, vilket cykliskt amin kan innehälla en eller flera andra heteroatomer och varvid nämnda Z har en substituent i en atom, som är intill ami-20 nets kväveatom, och X är NH3.
2. Komplex enligt patentkrav 1, kännetecknat av att Z är ett 5- eller 6-ledat monocykliskt eller 8 - 10-ledat polycykliskt amin.
3. Komplex enligt patentkrav 1, kännetecknat av att Z är ett bicykliskt amin med ett fusionerat ringsys-tem.
4. Komplex enligt patentkrav 1, kännetecknat av att Z är ett cykliskt amin, som är ett fusionerat ring-30 system, väri i den fusionerade ringen är en aromatisk ring 16 i det cykliska aininets ställningar 2 och 3.
5. Komplex enligt patentkrav 1, kännetecknat av att Z är en pyridinring.
6. Komplex enligt nagot av patentkraven 1-5, 5 varvid nämnda substituent är en akrylgrupp med 1-4 kolatomer, en alkoxigrupp med 1-4 kolatomer, en aryl-grupp eller en halogen.
7. Komplex enligt patentkrav 5, kännetecknat av att Z är pyridin, som är substituerat i 2-ställning med 10 1-4 kolatomers nedre alkyl- eller alkoxigrupp.
8. Komplex enligt nagot av de föregäende patentkraven, kännetecknat av att var och en grupp A är halogen, hydroxi eller karboxylat eller grupperna A bildar tillsammans ett tvätandat karboxylat eller sulfat.
9. Komplex enligt patentkrav 8, kännetecknat av att varje A är klor eller bäda A:na tillsammans bildar ett tvätandat karboxylat.
10. Komplex enligt patentkrav 1, kännetecknat av att den har valts bland följande: (SP—4—3)-ammindikloro(2- 20 metylpyridin)platina(II); (SP-4-3)-ammindikloro(2-etylpyri- din)platina(II); (SP-4-3) -ammindikloro(2-metylkinolin)platina (II) ; (SP-4-3)-ammindikloro(2,4-dimetylpyridin)platina(II); (SP-4-3)-ammindikloro (2-isopropylpyridin) platina (II) ; (SP-4- 3) -ammindikloro(2,6-dimetylpyridin)platina (II); (OC-6-43)- 25 ammindiklorodihydroxo(2,4-dimetylpyridin)platina (IV); (OC-6- 43) -amminbisbutyratodikloro(2,4-dimetylpyridin)platina (IV) och ämmin(cyklobutan-1,1-dikarboxylato(2,4-dimetylpyri-din)platina(II).
11. Komplex enligt patentkrav 10, kännetecknat 30 av att det är (SP-4-3)-ammindikloro (2-metylpyridin) platina (11) .
12. Farmaceutisk komposition, kännetecknad av att den omfattar som aktiv beständsdel ett komplex enligt nägot av de föregäende patentkraven som en blandning 35 med en farmaceutiskt godtagbar diluent eller bärare och eventuellt ett eller flera andra terapeutiska ämnen. 17
13. Komposition enligt patent krav 12, känne-tecknad av att den är i engängsdosform.
14. Komposition enligt patentkrav 12 eller 13, kännetecknad av att den är avsedd för oral admini- 5 strering.
15. Komplex enligt nägot av patentkraven 1 - 11 för att användas inom medicinen.
16. Användning av ett komplex enligt nägot av pa tentkraven 1-11 vid framställning av ett läkemedel avio sett för behandling av cancer.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9502799.1A GB9502799D0 (en) | 1995-02-14 | 1995-02-14 | Improvements in platinum complexes |
| GB9502799 | 1995-02-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI960660A0 FI960660A0 (sv) | 1996-02-14 |
| FI960660A FI960660A (sv) | 1996-08-15 |
| FI120493B true FI120493B (sv) | 2009-11-13 |
Family
ID=10769529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI960660A FI120493B (sv) | 1995-02-14 | 1996-02-14 | Förbättringar i platinakomplexer |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US5665771A (sv) |
| EP (1) | EP0727430B1 (sv) |
| JP (1) | JP3219235B2 (sv) |
| KR (1) | KR100339866B1 (sv) |
| AT (1) | ATE202111T1 (sv) |
| AU (1) | AU707814B2 (sv) |
| CA (1) | CA2169019C (sv) |
| DE (1) | DE69613254T2 (sv) |
| DK (1) | DK0727430T3 (sv) |
| ES (1) | ES2157399T3 (sv) |
| FI (1) | FI120493B (sv) |
| GB (1) | GB9502799D0 (sv) |
| GR (1) | GR3036513T3 (sv) |
| HK (1) | HK1011997A1 (sv) |
| NO (1) | NO307569B1 (sv) |
| NZ (1) | NZ280946A (sv) |
| PT (1) | PT727430E (sv) |
| TW (1) | TW432068B (sv) |
| ZA (1) | ZA96885B (sv) |
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 |
| US6413953B1 (en) * | 1999-04-13 | 2002-07-02 | Anormed Inc. | Pt(IV) antitumor agent |
| CN1916009B (zh) * | 1999-04-13 | 2010-12-15 | 阿诺麦德股份有限公司 | 制备胺铂配合物的方法 |
| WO2001024763A2 (en) | 1999-10-01 | 2001-04-12 | 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 |
| US7122668B2 (en) | 2001-08-23 | 2006-10-17 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Platinum complexes and their use in therapy |
| WO2007021852A2 (en) * | 2005-08-11 | 2007-02-22 | Virginia Commonwealth University | Transplatinum complexes with n2o2 donor sets as cytotoxic and antitumor agents |
| US8173686B2 (en) * | 2006-11-06 | 2012-05-08 | 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 |
| 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 |
| AU2008214202A1 (en) * | 2007-02-09 | 2008-08-14 | Genzyme Corporation | Stabilized picoplatin oral dosage form |
| EP2109451A4 (en) * | 2007-02-09 | 2012-12-19 | Poniard Pharmaceuticals Inc | PICOPLATINE ENCAPSULATED |
| US20110033528A1 (en) * | 2009-08-05 | 2011-02-10 | Poniard Pharmaceuticals, Inc. | Stabilized picoplatin oral dosage form |
| US20100260832A1 (en) * | 2007-06-27 | 2010-10-14 | Poniard Pharmaceuticals, Inc. | Combination therapy for ovarian cancer |
| TW200916094A (en) * | 2007-06-27 | 2009-04-16 | Poniard Pharmaceuticals Inc | Stabilized picoplatin dosage form |
| TW200920347A (en) * | 2007-07-16 | 2009-05-16 | Poniard Pharmaceuticals Inc | Oral formulations for picoplatin |
| EP2249644A4 (en) * | 2008-02-08 | 2012-05-30 | Poniard Pharmaceuticals Inc | PICOPLATIN AND AMRUBICIN USEFUL IN THE TREATMENT OF 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 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| ATE63919T1 (de) * | 1984-06-27 | 1991-06-15 | Johnson Matthey Plc | Platinkoordinationsverbindungen. |
| 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 |
| EP0273315B1 (en) * | 1986-12-18 | 1992-03-18 | SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. | Ammine-n-heterocyclic-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 |
| CN1916009B (zh) * | 1999-04-13 | 2010-12-15 | 阿诺麦德股份有限公司 | 制备胺铂配合物的方法 |
| US7122668B2 (en) * | 2001-08-23 | 2006-10-17 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Platinum complexes and their use in therapy |
| PT1789427E (pt) * | 2004-09-01 | 2009-07-31 | Platco Technologies Proprietar | Preparação de complexos de platina (ii) |
| WO2007021852A2 (en) * | 2005-08-11 | 2007-02-22 | 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 AT AT96300601T patent/ATE202111T1/de active
- 1996-01-29 DK DK96300601T patent/DK0727430T3/da active
- 1996-01-29 DE DE69613254T patent/DE69613254T2/de not_active Expired - Lifetime
- 1996-01-29 EP EP96300601A patent/EP0727430B1/en not_active Expired - Lifetime
- 1996-01-29 PT PT96300601T patent/PT727430E/pt unknown
- 1996-01-29 ES ES96300601T patent/ES2157399T3/es 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 CA CA002169019A patent/CA2169019C/en not_active Expired - Lifetime
- 1996-02-07 US US08/597,953 patent/US5665771A/en not_active Ceased
- 1996-02-07 TW TW085101525A patent/TW432068B/zh not_active IP Right Cessation
- 1996-02-07 NZ NZ280946A patent/NZ280946A/en not_active IP Right Cessation
- 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 JP JP02693596A patent/JP3219235B2/ja not_active Expired - Lifetime
- 1996-02-14 FI FI960660A patent/FI120493B/sv not_active IP Right Cessation
-
1998
- 1998-12-10 HK HK98113066A patent/HK1011997A1/xx not_active IP Right Cessation
-
2001
- 2001-09-04 GR GR20010401373T patent/GR3036513T3/el unknown
-
2009
- 2009-05-08 US US12/437,889 patent/USRE41209E1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO960569D0 (no) | 1996-02-13 |
| TW432068B (en) | 2001-05-01 |
| FI960660A (sv) | 1996-08-15 |
| US5665771A (en) | 1997-09-09 |
| GB9502799D0 (en) | 1995-04-05 |
| DE69613254T2 (de) | 2001-09-20 |
| AU4225896A (en) | 1996-08-22 |
| ES2157399T3 (es) | 2001-08-16 |
| CA2169019A1 (en) | 1996-08-15 |
| KR100339866B1 (ko) | 2002-11-07 |
| HK1011997A1 (en) | 1999-07-23 |
| AU707814B2 (en) | 1999-07-22 |
| EP0727430B1 (en) | 2001-06-13 |
| FI960660A0 (sv) | 1996-02-14 |
| NO307569B1 (no) | 2000-04-25 |
| EP0727430A1 (en) | 1996-08-21 |
| ZA96885B (en) | 1996-08-14 |
| NO960569L (no) | 1996-08-15 |
| KR960030940A (ko) | 1996-09-17 |
| ATE202111T1 (de) | 2001-06-15 |
| JPH08259581A (ja) | 1996-10-08 |
| CA2169019C (en) | 2003-02-04 |
| NZ280946A (en) | 1997-05-26 |
| USRE41209E1 (en) | 2010-04-06 |
| JP3219235B2 (ja) | 2001-10-15 |
| PT727430E (pt) | 2001-11-30 |
| DK0727430T3 (da) | 2001-09-03 |
| GR3036513T3 (en) | 2001-12-31 |
| DE69613254D1 (de) | 2001-07-19 |
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