CA1261864A - Liposoluble platinum (ii) complex and preparation thereof - Google Patents
Liposoluble platinum (ii) complex and preparation thereofInfo
- Publication number
- CA1261864A CA1261864A CA000503485A CA503485A CA1261864A CA 1261864 A CA1261864 A CA 1261864A CA 000503485 A CA000503485 A CA 000503485A CA 503485 A CA503485 A CA 503485A CA 1261864 A CA1261864 A CA 1261864A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- complex
- platinum
- group
- substituted
- 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
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 238000002360 preparation method Methods 0.000 title description 4
- 238000010668 complexation reaction Methods 0.000 title 1
- 239000002872 contrast media Substances 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 230000001546 nitrifying effect Effects 0.000 claims abstract description 8
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- -1 alkali metal salt Chemical class 0.000 claims abstract description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 26
- 201000011510 cancer Diseases 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 7
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 5
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical group C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 7
- 125000005313 fatty acid group Chemical group 0.000 claims 2
- 125000005654 1,2-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([*:2])C([H])([*:1])C1([H])[H] 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000000813 microbial effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000005471 saturated fatty acid group Chemical group 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 9
- 229930195729 fatty acid Natural products 0.000 abstract description 9
- 239000000194 fatty acid Substances 0.000 abstract description 9
- 239000002246 antineoplastic agent Substances 0.000 abstract description 8
- 150000004665 fatty acids Chemical class 0.000 abstract description 8
- 125000000962 organic group Chemical group 0.000 abstract description 7
- 239000004599 antimicrobial Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 14
- 241000699670 Mus sp. Species 0.000 description 12
- 239000003814 drug Substances 0.000 description 11
- 229910052697 platinum Inorganic materials 0.000 description 10
- BSJGASKRWFKGMV-UHFFFAOYSA-L ammonia dichloroplatinum(2+) Chemical compound N.N.Cl[Pt+2]Cl BSJGASKRWFKGMV-UHFFFAOYSA-L 0.000 description 9
- 238000002560 therapeutic procedure Methods 0.000 description 9
- 231100000331 toxic Toxicity 0.000 description 9
- 230000002588 toxic effect Effects 0.000 description 9
- 230000001093 anti-cancer Effects 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000002512 chemotherapy Methods 0.000 description 7
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 7
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000002459 sustained effect Effects 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000001959 radiotherapy Methods 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- 206010029155 Nephropathy toxic Diseases 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
- 208000032839 leukemia Diseases 0.000 description 4
- 230000007694 nephrotoxicity Effects 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
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- 206010025323 Lymphomas Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229960004316 cisplatin Drugs 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229940045845 sodium myristate Drugs 0.000 description 3
- 229940045870 sodium palmitate Drugs 0.000 description 3
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 3
- JUQGWKYSEXPRGL-UHFFFAOYSA-M sodium;tetradecanoate Chemical compound [Na+].CCCCCCCCCCCCCC([O-])=O JUQGWKYSEXPRGL-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000009897 systematic effect Effects 0.000 description 3
- 201000009030 Carcinoma Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 2
- KMLCRELJHYKIIL-UHFFFAOYSA-N [1-(azanidylmethyl)cyclohexyl]methylazanide;platinum(2+);sulfuric acid Chemical compound [Pt+2].OS(O)(=O)=O.[NH-]CC1(C[NH-])CCCCC1 KMLCRELJHYKIIL-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000002622 anti-tumorigenesis Effects 0.000 description 2
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960004562 carboplatin Drugs 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- FUSJRKGHMSFNTB-UHFFFAOYSA-L platinum(2+);tetradecanoate Chemical compound [Pt+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O FUSJRKGHMSFNTB-UHFFFAOYSA-L 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- CVYDEWKUJFCYJO-UHFFFAOYSA-M sodium;docosanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCCCC([O-])=O CVYDEWKUJFCYJO-UHFFFAOYSA-M 0.000 description 2
- 229950004330 spiroplatin Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical group CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- JABQIAUSEPNPCN-CVBJKYQLSA-L (z)-octadec-9-enoate;platinum(2+) Chemical compound [Pt+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O JABQIAUSEPNPCN-CVBJKYQLSA-L 0.000 description 1
- LQRDJCBZCLUBRY-UHFFFAOYSA-N 1,1-dichlorocyclohexane Chemical compound ClC1(Cl)CCCCC1 LQRDJCBZCLUBRY-UHFFFAOYSA-N 0.000 description 1
- 102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
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- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000008753 Papaver somniferum Nutrition 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 235000003441 saturated fatty acids Nutrition 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
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- 229940080350 sodium stearate Drugs 0.000 description 1
- FIWQZURFGYXCEO-UHFFFAOYSA-M sodium;decanoate Chemical compound [Na+].CCCCCCCCCC([O-])=O FIWQZURFGYXCEO-UHFFFAOYSA-M 0.000 description 1
- MRQYKJNZWPCFNB-UHFFFAOYSA-M sodium;icosanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCC([O-])=O MRQYKJNZWPCFNB-UHFFFAOYSA-M 0.000 description 1
- ROYMYVICTPBXGZ-UHFFFAOYSA-M sodium;tetracosanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCCCCCC([O-])=O ROYMYVICTPBXGZ-UHFFFAOYSA-M 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 208000010570 urinary bladder carcinoma Diseases 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP43869/1985 | 1985-03-06 | ||
| JP4386985 | 1985-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1261864A true CA1261864A (en) | 1989-09-26 |
Family
ID=12675703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000503485A Expired CA1261864A (en) | 1985-03-06 | 1986-03-06 | Liposoluble platinum (ii) complex and preparation thereof |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6613799B1 (enExample) |
| EP (1) | EP0193936B1 (enExample) |
| JP (1) | JPS6296A (enExample) |
| AT (1) | ATE43605T1 (enExample) |
| AU (1) | AU587235B2 (enExample) |
| CA (1) | CA1261864A (enExample) |
| DE (1) | DE3663667D1 (enExample) |
| ES (1) | ES8704505A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5384127A (en) * | 1985-10-18 | 1995-01-24 | Board Of Regents, The University Of Texas System | Stable liposomal formulations of lipophilic platinum compounds |
| US5041581A (en) * | 1985-10-18 | 1991-08-20 | The University Of Texas System Board Of Regents | Hydrophobic cis-platinum complexes efficiently incorporated into liposomes |
| US5117022A (en) * | 1985-10-18 | 1992-05-26 | The Board Of Regents, The University Of Texas System | Hydrophobic cis-platinum complexes efficiently incorporated into liposomes |
| GB8620917D0 (en) * | 1986-08-29 | 1986-10-08 | Davidson B C | Platinum derivatives & cancer treatments |
| 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 |
| US4880832A (en) * | 1987-03-06 | 1989-11-14 | Sumitomo Pharmaceuticals Company, Ltd. | Liposoluble platinum (II) complex and preparation thereof |
| AU592927B2 (en) * | 1988-02-18 | 1990-01-25 | Sumitomo Pharmaceuticals Company, Limited | Liposoluble platinum (ii) complex and preparation thereof |
| CA1339034C (en) * | 1988-08-22 | 1997-04-01 | Paul A. Tremblay | Platinum complexes of single isomer neoalkyl acids |
| US5393909A (en) * | 1988-11-22 | 1995-02-28 | Board Of Regents, The University Of Texas System | Diamine platinum complexes as antitumor agents |
| US5041578A (en) * | 1988-11-22 | 1991-08-20 | Board Of Regents, The University Of Texas System | Water soluble 1,2-diaminocyclohexane platinum (IV) complexes as antitumor agents |
| US5434256A (en) * | 1988-11-22 | 1995-07-18 | Board Of Regents, The University Of Texas System | Diamine platinum complexes as antitumor agents |
| ES2097085B1 (es) * | 1994-06-30 | 1997-11-16 | Univ Salamanca | Nuevos complejos de coordinacion de metales de transicion con actividad citostatica. |
| US5843475A (en) * | 1996-12-06 | 1998-12-01 | Board Of Regents, The University Of Texas System | Delivery and activation through liposome incorporation of diaminocyclohexane platinum (II) complexes |
| US6426367B1 (en) * | 1999-09-09 | 2002-07-30 | Efa Sciences Llc | Methods for selectively occluding blood supplies to neoplasias |
| JP5096657B2 (ja) | 2000-08-11 | 2012-12-12 | 大日本住友製薬株式会社 | シスプラチン耐性癌治療剤 |
| AUPR644301A0 (en) * | 2001-07-17 | 2001-08-09 | Unisearch Limited | Method and composition for treatment of cancer |
| WO2005023824A2 (en) * | 2003-08-13 | 2005-03-17 | University Of South Florida | Methods for inhibiting tumor cell proliferation |
| ITMI20052449A1 (it) * | 2005-12-22 | 2007-06-23 | Cell Therapeutics Europe Srl | Nuovi bis-platino complessi ad attivita' antitumorale |
| 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 |
| CN101830933B (zh) * | 2010-05-28 | 2012-07-25 | 昆明贵研药业有限公司 | 一种合成抗肿瘤药物米铂的方法 |
| CN101899067A (zh) * | 2010-08-10 | 2010-12-01 | 东南大学 | 米铂的制备方法 |
| CN102516311B (zh) * | 2011-11-03 | 2014-05-28 | 南京优科生物医药有限公司 | 一种米铂的制备方法 |
| CN103570766B (zh) * | 2012-08-09 | 2016-04-13 | 浙江海昶生物医药技术有限公司 | 一种新型铂类脂质体制剂及其制备方法 |
| JP2016531112A (ja) * | 2013-07-25 | 2016-10-06 | ネムコア メディカル イノベーションズ インコーポレイテッド | 疎水性白金誘導体のナノエマルジョン |
| CN103910762A (zh) * | 2014-04-16 | 2014-07-09 | 北京美迪康信医药科技有限公司 | 一种米铂的制备方法 |
| WO2015166498A1 (en) * | 2014-05-02 | 2015-11-05 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd | Pt (iv) derivatives and nanocarriers comprising them |
| CN104211734A (zh) * | 2014-08-10 | 2014-12-17 | 昆明贵研药业有限公司 | 一种合成抗肿瘤药物庚铂的新方法 |
| CN105153238B (zh) * | 2015-09-12 | 2017-08-15 | 山东罗欣药业集团股份有限公司 | 一种米铂的制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR898614A (fr) | 1942-10-15 | 1945-04-27 | Auergesellschaft Ag | Verre à lunettes contenant du néodyme |
| US4206226A (en) * | 1977-08-29 | 1980-06-03 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Use of 4-carboxy-phthalato-(1,2-diaminocyclohexane)-platinum(II) and alkali metal salts thereof in alleviating L1210 murine leukemia |
| SE447385B (sv) * | 1977-10-19 | 1986-11-10 | Johnson Matthey Co Ltd | Cis-koordinationsforeningar av platina |
| SE447902B (sv) * | 1977-10-19 | 1986-12-22 | Johnson Matthey Co Ltd | Cis-koordinationsforening av platina och komposition innehallande foreningen |
| US4203912A (en) * | 1977-10-19 | 1980-05-20 | Johnson, Matthey & Co., Limited | Compositions containing platinum |
| US4284579A (en) * | 1979-07-17 | 1981-08-18 | The United States Of America As Represented By The Of The Department Of Health & Human Services | (N-Phosphonacetyl-L-aspartato)(1,2-diaminocyclchexane)platinum(II) or alkali metal salt |
| JPS56154493A (en) * | 1980-04-30 | 1981-11-30 | Shionogi & Co Ltd | Novel platinum complex |
| JPS5716895A (en) * | 1980-07-05 | 1982-01-28 | Otsuka Chem Co Ltd | Platinum 2 complex and antitumor agent containing the same as active principle |
| JPS57123198A (en) * | 1981-01-23 | 1982-07-31 | Shionogi & Co Ltd | Novel platinum complex |
| EP0113508A1 (en) | 1982-11-04 | 1984-07-18 | Inco Research & Development Center, Inc. | Hydrophobic platinum compounds and their preparation |
| EP0130482B1 (en) * | 1983-06-20 | 1988-12-28 | Research Corporation | Diaminocyclohexane platinum complexes, process for preparing same and pharmaceutical compositions containing same |
| EP0136012B1 (en) | 1983-08-05 | 1989-04-19 | Yoshinori Kidani | Cytostatic platinum complexes |
| US5041581A (en) | 1985-10-18 | 1991-08-20 | The University Of Texas System Board Of Regents | Hydrophobic cis-platinum complexes efficiently incorporated into liposomes |
-
1986
- 1986-02-28 JP JP61044903A patent/JPS6296A/ja active Granted
- 1986-03-05 AT AT86102860T patent/ATE43605T1/de not_active IP Right Cessation
- 1986-03-05 EP EP86102860A patent/EP0193936B1/en not_active Expired
- 1986-03-05 DE DE8686102860T patent/DE3663667D1/de not_active Expired
- 1986-03-05 US US06/836,524 patent/US6613799B1/en not_active Expired - Lifetime
- 1986-03-06 ES ES552722A patent/ES8704505A1/es not_active Expired
- 1986-03-06 AU AU54358/86A patent/AU587235B2/en not_active Ceased
- 1986-03-06 CA CA000503485A patent/CA1261864A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US6613799B1 (en) | 2003-09-02 |
| AU587235B2 (en) | 1989-08-10 |
| EP0193936A1 (en) | 1986-09-10 |
| JPS6296A (ja) | 1987-01-06 |
| ATE43605T1 (de) | 1989-06-15 |
| ES8704505A1 (es) | 1987-04-01 |
| EP0193936B1 (en) | 1989-05-31 |
| AU5435886A (en) | 1986-09-11 |
| ES552722A0 (es) | 1987-04-01 |
| JPH0576954B2 (enExample) | 1993-10-25 |
| DE3663667D1 (en) | 1989-07-06 |
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| MKEX | Expiry |