IL101167A - Platinum brackets (II), processes for their preparation, and pharmaceutical preparations containing them - Google Patents
Platinum brackets (II), processes for their preparation, and pharmaceutical preparations containing themInfo
- Publication number
- IL101167A IL101167A IL10116792A IL10116792A IL101167A IL 101167 A IL101167 A IL 101167A IL 10116792 A IL10116792 A IL 10116792A IL 10116792 A IL10116792 A IL 10116792A IL 101167 A IL101167 A IL 101167A
- Authority
- IL
- Israel
- Prior art keywords
- bis
- platinum
- dioxolane
- aminomethyl
- formula
- Prior art date
Links
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical class [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 title claims abstract description 209
- 238000000034 method Methods 0.000 title claims abstract description 89
- 230000008569 process Effects 0.000 title claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 65
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- 150000001924 cycloalkanes Chemical group 0.000 claims abstract description 4
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 241001465754 Metazoa Species 0.000 claims abstract description 3
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical group C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims description 235
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 105
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 63
- 239000000243 solution Substances 0.000 claims description 46
- 239000007864 aqueous solution Substances 0.000 claims description 39
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 34
- 229910052697 platinum Inorganic materials 0.000 claims description 30
- VFWRGKJLLYDFBY-UHFFFAOYSA-N silver;hydrate Chemical compound O.[Ag].[Ag] VFWRGKJLLYDFBY-UHFFFAOYSA-N 0.000 claims description 20
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 17
- 239000003957 anion exchange resin Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 9
- UUOFRXDFODYHPC-RNFRBKRXSA-N [(4r,5r)-5-(aminomethyl)-2-propan-2-yl-1,3-dioxolan-4-yl]methanamine Chemical compound CC(C)C1O[C@H](CN)[C@@H](CN)O1 UUOFRXDFODYHPC-RNFRBKRXSA-N 0.000 claims description 8
- 239000012736 aqueous medium Substances 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000002609 medium Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 3
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 230000000259 anti-tumor effect Effects 0.000 abstract description 11
- 230000003389 potentiating effect Effects 0.000 abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001721 carbon Chemical group 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 3
- IVKNYMXGZKPFOJ-UHFFFAOYSA-N [5-(aminomethyl)-1,3-dioxolan-4-yl]methanamine Chemical group NCC1OCOC1CN IVKNYMXGZKPFOJ-UHFFFAOYSA-N 0.000 abstract description 2
- 201000011510 cancer Diseases 0.000 abstract description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 147
- 230000015572 biosynthetic process Effects 0.000 description 130
- 238000003786 synthesis reaction Methods 0.000 description 130
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 74
- 239000000203 mixture Substances 0.000 description 70
- 238000005481 NMR spectroscopy Methods 0.000 description 54
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 53
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 44
- 239000007787 solid Substances 0.000 description 42
- -1 platinum coordination complex Chemical class 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 36
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 35
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 34
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 34
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 30
- 239000000377 silicon dioxide Substances 0.000 description 30
- 239000003921 oil Substances 0.000 description 29
- 238000002953 preparative HPLC Methods 0.000 description 29
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 26
- 238000000746 purification Methods 0.000 description 25
- 231100000331 toxic Toxicity 0.000 description 25
- 230000002588 toxic effect Effects 0.000 description 25
- 229910052700 potassium Inorganic materials 0.000 description 21
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 20
- 239000011591 potassium Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- RNJPWBVOCUGBGY-UHFFFAOYSA-J tetraiodoplatinum Chemical compound [I-].[I-].[I-].[I-].[Pt+4] RNJPWBVOCUGBGY-UHFFFAOYSA-J 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 241000699670 Mus sp. Species 0.000 description 17
- 238000000921 elemental analysis Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 13
- 229920001429 chelating resin Polymers 0.000 description 13
- 229940098779 methanesulfonic acid Drugs 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 239000012452 mother liquor Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- YCPOZVAOBBQLRI-PHDIDXHHSA-N [(2r,3r)-2,3-dihydroxy-4-methylsulfonyloxybutyl] methanesulfonate Chemical compound CS(=O)(=O)OC[C@@H](O)[C@H](O)COS(C)(=O)=O YCPOZVAOBBQLRI-PHDIDXHHSA-N 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 8
- 101150046236 CNR1 gene Proteins 0.000 description 8
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 8
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 8
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- XGMAKKXJDDDGCD-UHFFFAOYSA-L disilver;cyclobutane-1,1-dicarboxylate Chemical compound [Ag+].[Ag+].[O-]C(=O)C1(C([O-])=O)CCC1 XGMAKKXJDDDGCD-UHFFFAOYSA-L 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 101150041968 CDC13 gene Proteins 0.000 description 7
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 7
- 229960004316 cisplatin Drugs 0.000 description 7
- 231100000225 lethality Toxicity 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 6
- 231100000111 LD50 Toxicity 0.000 description 6
- 206010029155 Nephropathy toxic Diseases 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YCPOZVAOBBQLRI-WDSKDSINSA-N Treosulfan Chemical compound CS(=O)(=O)OC[C@H](O)[C@@H](O)COS(C)(=O)=O YCPOZVAOBBQLRI-WDSKDSINSA-N 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 231100000417 nephrotoxicity Toxicity 0.000 description 6
- 230000007694 nephrotoxicity Effects 0.000 description 6
- 229940023144 sodium glycolate Drugs 0.000 description 6
- 239000001540 sodium lactate Substances 0.000 description 6
- 235000011088 sodium lactate Nutrition 0.000 description 6
- 229940005581 sodium lactate Drugs 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 5
- 208000007093 Leukemia L1210 Diseases 0.000 description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
- 241001529936 Murinae Species 0.000 description 5
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 5
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- YSAVZVORKRDODB-WDSKDSINSA-N diethyl tartrate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC YSAVZVORKRDODB-WDSKDSINSA-N 0.000 description 5
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 4
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 4
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 4
- 229940109239 creatinine Drugs 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229910021612 Silver iodide Inorganic materials 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229940045105 silver iodide Drugs 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- MBNMGGKBGCIEGF-UHFFFAOYSA-N 1,1-diethoxypropane Chemical compound CCOC(CC)OCC MBNMGGKBGCIEGF-UHFFFAOYSA-N 0.000 description 2
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- KQGQLRAYJUXGOW-WDSKDSINSA-N [(4s,5s)-5-(aminomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanamine Chemical compound CC1(C)O[C@@H](CN)[C@H](CN)O1 KQGQLRAYJUXGOW-WDSKDSINSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229960001270 d- tartaric acid Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ONDVNRNSHFNJHG-HTQZYQBOSA-N (4r,5r)-4,5-bis(azidomethyl)-2,2-diethyl-1,3-dioxolane Chemical compound CCC1(CC)O[C@H](CN=[N+]=[N-])[C@@H](CN=[N+]=[N-])O1 ONDVNRNSHFNJHG-HTQZYQBOSA-N 0.000 description 1
- INJUNLDNDNSXHM-HTQZYQBOSA-N (4r,5r)-4,5-bis(azidomethyl)-2-(2-methylpropyl)-1,3-dioxolane Chemical compound CC(C)CC1O[C@H](CN=[N+]=[N-])[C@@H](CN=[N+]=[N-])O1 INJUNLDNDNSXHM-HTQZYQBOSA-N 0.000 description 1
- ZYYGSQZNHAQJRG-RNFRBKRXSA-N (4r,5r)-4,5-bis(azidomethyl)-2-ethyl-2-methyl-1,3-dioxolane Chemical compound CCC1(C)O[C@H](CN=[N+]=[N-])[C@@H](CN=[N+]=[N-])O1 ZYYGSQZNHAQJRG-RNFRBKRXSA-N 0.000 description 1
- KEYOLTKQGFTWEB-RNFRBKRXSA-N (4r,5r)-4,5-bis(azidomethyl)-2-tert-butyl-1,3-dioxolane Chemical compound CC(C)(C)C1O[C@H](CN=[N+]=[N-])[C@@H](CN=[N+]=[N-])O1 KEYOLTKQGFTWEB-RNFRBKRXSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000011765 DBA/2 mouse Methods 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- UNXHWFMMPAWVPI-IMJSIDKUSA-N L-threitol Chemical compound OC[C@H](O)[C@@H](O)CO UNXHWFMMPAWVPI-IMJSIDKUSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
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- IVKNYMXGZKPFOJ-RFZPGFLSSA-N [(4r,5r)-5-(aminomethyl)-1,3-dioxolan-4-yl]methanamine Chemical compound NC[C@H]1OCO[C@@H]1CN IVKNYMXGZKPFOJ-RFZPGFLSSA-N 0.000 description 1
- UASWARWHYQUFNB-HTQZYQBOSA-N [(4r,5r)-5-(aminomethyl)-2,2-diethyl-1,3-dioxolan-4-yl]methanamine Chemical compound CCC1(CC)O[C@H](CN)[C@@H](CN)O1 UASWARWHYQUFNB-HTQZYQBOSA-N 0.000 description 1
- KQGQLRAYJUXGOW-PHDIDXHHSA-N [(4r,5r)-5-(aminomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methanamine Chemical compound CC1(C)O[C@H](CN)[C@@H](CN)O1 KQGQLRAYJUXGOW-PHDIDXHHSA-N 0.000 description 1
- YWUQXOIKJVOHMA-HTQZYQBOSA-N [(4r,5r)-5-(aminomethyl)-2-(2-methylpropyl)-1,3-dioxolan-4-yl]methanamine Chemical compound CC(C)CC1O[C@H](CN)[C@@H](CN)O1 YWUQXOIKJVOHMA-HTQZYQBOSA-N 0.000 description 1
- UNWDNTKHFWDFDQ-RNFRBKRXSA-N [(4r,5r)-5-(aminomethyl)-2-ethyl-2-methyl-1,3-dioxolan-4-yl]methanamine Chemical compound CCC1(C)O[C@H](CN)[C@@H](CN)O1 UNWDNTKHFWDFDQ-RNFRBKRXSA-N 0.000 description 1
- VYOOYBJLWWTBDP-PHDIDXHHSA-N [(4r,5r)-5-(aminomethyl)-2-methyl-1,3-dioxolan-4-yl]methanamine Chemical compound CC1O[C@H](CN)[C@@H](CN)O1 VYOOYBJLWWTBDP-PHDIDXHHSA-N 0.000 description 1
- XLGDUOJUMJAUCP-RNFRBKRXSA-N [(4r,5r)-5-(aminomethyl)-2-propyl-1,3-dioxolan-4-yl]methanamine Chemical compound CCCC1O[C@H](CN)[C@@H](CN)O1 XLGDUOJUMJAUCP-RNFRBKRXSA-N 0.000 description 1
- PRCKYMCPESFIPF-WDSKDSINSA-N [(4s,5s)-5-(aminomethyl)-2-ethyl-1,3-dioxolan-4-yl]methanamine Chemical compound CCC1O[C@@H](CN)[C@H](CN)O1 PRCKYMCPESFIPF-WDSKDSINSA-N 0.000 description 1
- VYOOYBJLWWTBDP-WDSKDSINSA-N [(4s,5s)-5-(aminomethyl)-2-methyl-1,3-dioxolan-4-yl]methanamine Chemical compound CC1O[C@@H](CN)[C@H](CN)O1 VYOOYBJLWWTBDP-WDSKDSINSA-N 0.000 description 1
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- BSJGASKRWFKGMV-UHFFFAOYSA-L ammonia dichloroplatinum(2+) Chemical compound N.N.Cl[Pt+2]Cl BSJGASKRWFKGMV-UHFFFAOYSA-L 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 201000011263 bladder neck cancer Diseases 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 231100000371 dose-limiting toxicity Toxicity 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 201000010536 head and neck cancer Diseases 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- 230000035777 life prolongation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000262 ototoxicity Toxicity 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FGCSIJPPCNCQJB-FAOVPRGRSA-M sodium;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;chloride Chemical compound [Na+].[Cl-].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O FGCSIJPPCNCQJB-FAOVPRGRSA-M 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000002381 testicular Effects 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YCPOZVAOBBQLRI-UHFFFAOYSA-N treosulfan Chemical compound CS(=O)(=O)OCC(O)C(O)COS(C)(=O)=O YCPOZVAOBBQLRI-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 230000003442 weekly effect Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR910004627 | 1991-03-23 | ||
| KR910007207 | 1991-05-03 | ||
| KR910013205 | 1991-07-31 | ||
| KR1019910019969A KR940010296B1 (ko) | 1991-05-03 | 1991-11-11 | 신규한 플라티늄(ⅱ) 착화합물과 그의 제조방법 |
| KR1019910024632A KR940010298B1 (ko) | 1991-07-31 | 1991-12-27 | 신규한 플라티늄(ii) 착화합물과 그의 제조방법 |
| KR1019910024631A KR940010297B1 (ko) | 1991-03-23 | 1991-12-27 | 신규한 플라티늄(ii) 착화합물과 그의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL101167A0 IL101167A0 (en) | 1992-11-15 |
| IL101167A true IL101167A (en) | 1996-08-04 |
Family
ID=27555050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10116792A IL101167A (en) | 1991-03-23 | 1992-03-06 | Platinum brackets (II), processes for their preparation, and pharmaceutical preparations containing them |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5395947A (fr) |
| EP (1) | EP0586378B1 (fr) |
| JP (1) | JP2801965B2 (fr) |
| CN (2) | CN1038590C (fr) |
| AT (1) | ATE171455T1 (fr) |
| AU (2) | AU654990B2 (fr) |
| BR (1) | BR9107299A (fr) |
| CA (1) | CA2106679C (fr) |
| CZ (1) | CZ285904B6 (fr) |
| DE (1) | DE69130261T2 (fr) |
| ES (1) | ES2124251T3 (fr) |
| FI (1) | FI934150A (fr) |
| HU (3) | HUT65220A (fr) |
| IE (1) | IE920687A1 (fr) |
| IL (1) | IL101167A (fr) |
| NO (1) | NO304652B1 (fr) |
| NZ (1) | NZ241824A (fr) |
| PH (1) | PH30926A (fr) |
| PT (1) | PT100272B (fr) |
| RU (1) | RU2067099C1 (fr) |
| WO (1) | WO1992016539A1 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1068002C (zh) * | 1997-04-30 | 2001-07-04 | 中国科学院大连化学物理研究所 | 铂抗癌药物及合成 |
| WO2001024763A2 (fr) | 1999-10-01 | 2001-04-12 | Immunogen, Inc. | Compositions et methodes de traitement du cancer utilisant des immunoconjugues et des agents chimiotherapeutiques |
| CN100497359C (zh) * | 2006-01-06 | 2009-06-10 | 昆明贵研药业有限公司 | 抗癌药舒铂的一种新合成工艺 |
| RU2457838C1 (ru) * | 2011-04-13 | 2012-08-10 | Федеральное Государственное Бюджетное Учреждение Науки Институт Химии И Химической Технологии Сибирского Отделения Российской Академии Наук (Иххт Со Ран) | Способ получения транс-1,2-диаминциклогексантетрахлороплатины (iv) |
| CN103242509B (zh) * | 2013-04-18 | 2015-06-10 | 艾达索高新材料无锡有限公司 | 可降解环缩醛、环缩酮二胺类环氧树脂固化剂及其应用 |
| DK3280408T3 (da) * | 2015-04-10 | 2020-02-03 | Syn Nat Products Entpr Llc | Fremgangsmåde til fremstilling af dicycloplatin |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4657927A (en) * | 1978-05-04 | 1987-04-14 | Research Corporation | Malonato platinum compounds |
| NZ197104A (en) * | 1980-05-27 | 1984-05-31 | Bristol Myers Co | Soluble ammonium and sodium salts of 2-hydroxymalonato platinum ii derivatives |
| DE3432320A1 (de) * | 1984-09-03 | 1986-03-13 | Behringwerke Ag, 3550 Marburg | Cis-platin-komplexe mit einem pentaerythritderivat als liganden, verfahren zu ihrer herstellung und diese verbindungen enthaltendes pharmazeutisches mittel |
| US4665210A (en) * | 1984-12-17 | 1987-05-12 | American Cyanamid Company | Platinum complexes of aliphatic tricarboxylic acids |
| GB8525689D0 (en) * | 1985-10-18 | 1985-11-20 | Johnson Mathey Plc | Platinum coordination compounds |
| US4882447A (en) * | 1987-02-20 | 1989-11-21 | Tanabe Seiyaku Co., Ltd. | Novel organic platinum complex and process for the preparation thereof |
| IL85595A0 (en) * | 1987-03-06 | 1988-08-31 | Tanabe Seiyaku Co | Organic platinum complex and its preparation |
| JPS63267794A (ja) * | 1987-04-23 | 1988-11-04 | Sanwa Kagaku Kenkyusho Co Ltd | 有機白金錯体及びこれを有効成分とする抗腫瘍剤 |
| US4808730A (en) * | 1987-06-23 | 1989-02-28 | American Cyanamid Company | Synthesis of cisplatin analogs |
| US4870070A (en) * | 1987-08-10 | 1989-09-26 | American Cyanamid Company | Water soluble platinum complexes of novel malonate derivatives |
| 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 |
-
1991
- 1991-12-30 HU HU9302461A patent/HUT65220A/hu unknown
- 1991-12-30 ES ES92902293T patent/ES2124251T3/es not_active Expired - Lifetime
- 1991-12-30 DE DE69130261T patent/DE69130261T2/de not_active Expired - Fee Related
- 1991-12-30 JP JP4502604A patent/JP2801965B2/ja not_active Expired - Fee Related
- 1991-12-30 WO PCT/KR1991/000036 patent/WO1992016539A1/fr active IP Right Grant
- 1991-12-30 CA CA002106679A patent/CA2106679C/fr not_active Expired - Fee Related
- 1991-12-30 AU AU91247/91A patent/AU654990B2/en not_active Ceased
- 1991-12-30 EP EP92902293A patent/EP0586378B1/fr not_active Expired - Lifetime
- 1991-12-30 BR BR9107299A patent/BR9107299A/pt not_active Application Discontinuation
- 1991-12-30 AT AT92902293T patent/ATE171455T1/de not_active IP Right Cessation
- 1991-12-30 RU RU9193057869A patent/RU2067099C1/ru not_active IP Right Cessation
- 1991-12-30 HU HU9302461A patent/HU220869B1/hu not_active IP Right Cessation
- 1991-12-30 HU HU9502323A patent/HUT72890A/hu unknown
-
1992
- 1992-03-04 NZ NZ241824A patent/NZ241824A/xx unknown
- 1992-03-04 IE IE068792A patent/IE920687A1/en not_active Application Discontinuation
- 1992-03-06 IL IL10116792A patent/IL101167A/en not_active IP Right Cessation
- 1992-03-20 PT PT100272A patent/PT100272B/pt not_active IP Right Cessation
- 1992-03-23 PH PH44095A patent/PH30926A/en unknown
- 1992-03-23 CN CN92102045A patent/CN1038590C/zh not_active Expired - Fee Related
- 1992-03-23 CZ CS92873A patent/CZ285904B6/cs not_active IP Right Cessation
-
1993
- 1993-09-14 US US08/117,096 patent/US5395947A/en not_active Expired - Fee Related
- 1993-09-22 FI FI934150A patent/FI934150A/fi unknown
- 1993-09-22 NO NO932824A patent/NO304652B1/no unknown
-
1994
- 1994-10-05 AU AU74439/94A patent/AU7443994A/en not_active Abandoned
-
1997
- 1997-10-31 CN CN97120205A patent/CN1063753C/zh not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |