IL93090A - Platinum compounds and pharmaceutical preparations containing them - Google Patents

Platinum compounds and pharmaceutical preparations containing them

Info

Publication number: IL93090A
Authority: IL; Israel
Prior art keywords: compound; platinum; cis; water; cancer
Prior art date: 1989-01-17

Application number

IL9309090A

Other languages

English (en)

Hebrew (he)

Other versions

IL93090A0 (en

Original Assignee

Univ Georgetown

Priority date (The priority date 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 date listed.)

1989-01-17

Filing date

1990-01-17

Publication date

1995-10-31

1990-01-17 Application filed by Univ Georgetown filed Critical Univ Georgetown

1990-11-05 Publication of IL93090A0 publication Critical patent/IL93090A0/xx

1995-10-31 Publication of IL93090A publication Critical patent/IL93090A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 8
229940045985 antineoplastic platinum compound Drugs 0.000 title description 2
150000003058 platinum compounds Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 86
229910052757 nitrogen Inorganic materials 0.000 claims description 27
HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 16
150000002016 disaccharides Chemical class 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000001483 monosaccharide substituent group Chemical group 0.000 claims description 8
150000002772 monosaccharides Chemical class 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
206010033128 Ovarian cancer Diseases 0.000 claims description 5
206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
201000010536 head and neck cancer Diseases 0.000 claims description 5
208000014829 head and neck neoplasm Diseases 0.000 claims description 5
125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
208000024313 Testicular Neoplasms Diseases 0.000 claims description 4
206010057644 Testis cancer Diseases 0.000 claims description 4
125000002619 bicyclic group Chemical group 0.000 claims description 4
208000029742 colonic neoplasm Diseases 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
201000003120 testicular cancer Diseases 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
239000000203 mixture Substances 0.000 description 50
239000000243 solution Substances 0.000 description 31
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 26
229940093499 ethyl acetate Drugs 0.000 description 24
235000019439 ethyl acetate Nutrition 0.000 description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 21
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
239000002552 dosage form Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
239000000706 filtrate Substances 0.000 description 17
-1 N-acetylamino Chemical group 0.000 description 13
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 13
229910001863 barium hydroxide Inorganic materials 0.000 description 13
150000002540 isothiocyanates Chemical class 0.000 description 13
229910052697 platinum Inorganic materials 0.000 description 13
239000000047 product Substances 0.000 description 13
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 12
238000001704 evaporation Methods 0.000 description 12
230000008020 evaporation Effects 0.000 description 12
238000007912 intraperitoneal administration Methods 0.000 description 12
238000001990 intravenous administration Methods 0.000 description 12
238000004809 thin layer chromatography Methods 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 11
230000008034 disappearance Effects 0.000 description 11
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
229960004316 cisplatin Drugs 0.000 description 10
229940035423 ethyl ether Drugs 0.000 description 10
239000000644 isotonic solution Substances 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 10
239000002253 acid Substances 0.000 description 9
230000004083 survival effect Effects 0.000 description 9
241000699670 Mus sp. Species 0.000 description 8
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 8
208000032839 leukemia Diseases 0.000 description 8
238000007918 intramuscular administration Methods 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
241001529936 Murinae Species 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
206010028980 Neoplasm Diseases 0.000 description 4
239000002246 antineoplastic agent Substances 0.000 description 4
150000001720 carbohydrates Chemical class 0.000 description 4
DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 4
239000008103 glucose Substances 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 3
229910052788 barium Inorganic materials 0.000 description 3
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 3
210000001185 bone marrow Anatomy 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
239000000969 carrier Substances 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
229930182830 galactose Natural products 0.000 description 3
239000001863 hydroxypropyl cellulose Substances 0.000 description 3
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
210000003734 kidney Anatomy 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000008223 sterile water Substances 0.000 description 3
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
201000009030 Carcinoma Diseases 0.000 description 2
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
238000011765 DBA/2 mouse Methods 0.000 description 2
239000001856 Ethyl cellulose Substances 0.000 description 2
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000001093 anti-cancer Effects 0.000 description 2
230000000719 anti-leukaemic effect Effects 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
229940109239 creatinine Drugs 0.000 description 2
150000008266 deoxy sugars Chemical class 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000019325 ethyl cellulose Nutrition 0.000 description 2
229920001249 ethyl cellulose Polymers 0.000 description 2
239000000945 filler Substances 0.000 description 2
229960002442 glucosamine Drugs 0.000 description 2
229930182470 glycoside Chemical group 0.000 description 2
150000002338 glycosides Chemical group 0.000 description 2
238000002513 implantation Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
210000000265 leukocyte Anatomy 0.000 description 2
239000002502 liposome Substances 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
125000003132 pyranosyl group Chemical group 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
229910000367 silver sulfate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
150000005846 sugar alcohols Chemical class 0.000 description 2
239000003826 tablet Substances 0.000 description 2
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125000004178 (C1-C4) alkyl group Chemical group 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
DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 1
WCOXQTXVACYMLM-UHFFFAOYSA-N 2,3-bis(12-hydroxyoctadecanoyloxy)propyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC(O)CCCCCC)COC(=O)CCCCCCCCCCC(O)CCCCCC WCOXQTXVACYMLM-UHFFFAOYSA-N 0.000 description 1
CLOSFPUIYFHGPR-UHFFFAOYSA-L 2-acetamidopropanedioate;barium(2+) Chemical compound [Ba+2].CC(=O)NC(C([O-])=O)C([O-])=O CLOSFPUIYFHGPR-UHFFFAOYSA-L 0.000 description 1
MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 1
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WLEHEWWMHHJASO-UHFFFAOYSA-N 4-aminocyclohexane-1,1-dicarboxylic acid Chemical compound NC1CCC(C(O)=O)(C(O)=O)CC1 WLEHEWWMHHJASO-UHFFFAOYSA-N 0.000 description 1
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
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GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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SGLJYTWMWIAGEU-UHFFFAOYSA-N cyclohexane-1,2-diamine;platinum(2+) Chemical compound [Pt+2].NC1CCCCC1N SGLJYTWMWIAGEU-UHFFFAOYSA-N 0.000 description 1
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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230000001419 dependent effect Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
ISOLMABRZPQKOV-UHFFFAOYSA-N diethyl 2-acetamidopropanedioate Chemical compound CCOC(=O)C(NC(C)=O)C(=O)OCC ISOLMABRZPQKOV-UHFFFAOYSA-N 0.000 description 1
125000000600 disaccharide group Chemical group 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000037406 food intake Effects 0.000 description 1
125000003843 furanosyl group Chemical group 0.000 description 1
229950006191 gluconic acid Drugs 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
229940060367 inert ingredients Drugs 0.000 description 1
239000006204 intramuscular dosage form Substances 0.000 description 1
239000006206 intraperitoneal dosage form Substances 0.000 description 1
239000006207 intravenous dosage form Substances 0.000 description 1
DLRVVLDZNNYCBX-RTPHMHGBSA-N isomaltose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 DLRVVLDZNNYCBX-RTPHMHGBSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000003446 ligand Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
ZVYNEIVHNNYCSE-UHFFFAOYSA-N piperidine-4,4-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCNCC1 ZVYNEIVHNNYCSE-UHFFFAOYSA-N 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
102200044872 rs387906892 Human genes 0.000 description 1
102220036716 rs587780004 Human genes 0.000 description 1
HSNZZMHEPUFJNZ-SHUUEZRQSA-N sedoheptulose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO HSNZZMHEPUFJNZ-SHUUEZRQSA-N 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 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
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
229960005137 succinic acid Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002381 testicular Effects 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000464 thioxo group Chemical group S=* 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
201000005112 urinary bladder cancer Diseases 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biotechnology (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Saccharide Compounds (AREA)

IL9309090A 1989-01-17 1990-01-17 Platinum compounds and pharmaceutical preparations containing them IL93090A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US29736889A	1989-01-17	1989-01-17
US07/301,773 US4946954A (en)	1989-01-17	1989-01-26	Platinum pharmaceutical agents

Publications (2)

Publication Number	Publication Date
IL93090A0 IL93090A0 (en)	1990-11-05
IL93090A true IL93090A (en)	1995-10-31

Family

ID=26970120

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9309090A IL93090A (en)	1989-01-17	1990-01-17	Platinum compounds and pharmaceutical preparations containing them

Country Status (13)

Country	Link
US (1)	US4946954A (de)
EP (1)	EP0462980A4 (de)
JP (1)	JP2771326B2 (de)
AU (2)	AU5039490A (de)
CA (1)	CA2045120A1 (de)
HU (1)	HUT59690A (de)
IL (1)	IL93090A (de)
NO (1)	NO180588C (de)
NZ (1)	NZ232134A (de)
PH (1)	PH26424A (de)
RU (1)	RU2074861C1 (de)
WO (1)	WO1990008157A1 (de)
ZA (1)	ZA90336B (de)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5041581A (en) *	1985-10-18	1991-08-20	The University Of Texas System Board Of Regents	Hydrophobic cis-platinum complexes efficiently incorporated into liposomes
US5384127A (en) *	1985-10-18	1995-01-24	Board Of Regents, The University Of Texas System	Stable liposomal formulations of lipophilic platinum compounds
AU614901B2 (en) *	1989-04-04	1991-09-12	Daikin Industries, Ltd.	New fluorocarbon platinum complexes
US5871710A (en) *	1992-09-04	1999-02-16	The General Hospital Corporation	Graft co-polymer adducts of platinum (II) compounds
WO1996000079A1 (en) *	1994-06-27	1996-01-04	The General Hospital Corporation	Graft co-polymer adducts of platinum (ii) compounds
NZ307633A (en) *	1995-05-09	2000-01-28	Kreatech Biotechnology Bv	Methods for the production of platinum-based linkers between labels and bio-organic molecules, for labelling bio-organic molecules, for detecting
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
US6235776B1 (en)	1998-11-12	2001-05-22	Cell Pathways, Inc.	Method for treating a patient with neoplasia by treatment with a paclitaxel derivative
US6235782B1 (en)	1998-11-12	2001-05-22	Rifat Pamukcu	Method for treating a patient with neoplasia by treatment with a platinum coordination complex
JP4776843B2 (ja)	1999-10-01	2011-09-21	イムノゲンインコーポレーティッド	免疫複合体及び化学療法剤を用いる癌治療用組成物及び方法
AU2006222657B2 (en) *	2000-01-04	2009-01-15	Access Pharmaceuticals, Inc.	N,O-amidomalonate platinum complexes
US7166733B2 (en) *	2000-01-04	2007-01-23	Access Pharmaceuticals, Inc.	O,O'-Amidomalonate and N,O-Amidomalonate platinum complexes
CA2396702C (en) *	2000-01-04	2010-03-23	Access Pharmaceuticals, Inc.	N,o-amidomalonate platinum complexes
RU2219183C2 (ru) *	2000-03-03	2003-12-20	Зукин ЯН	Производное комплекса удвоенная дикарбоновая кислота-диаминоплатина, способ его получения, противоопухолевая фармацевтическая композиция и использование этого производного
KR20040074857A (ko) *	2003-02-19	2004-08-26	학교법인 이화학당	Ｎ-치환 아미노디카복실산의 백금(ⅱ) 착물 및 그 제조방법
JP2006521300A (ja) *	2003-03-31	2006-09-21	プリヴァ−ラケマ，エー．エス．	活性物質として白金錯体を含有する医薬組成物およびその製造方法
KR100499340B1 (ko) *	2003-04-29	2005-07-04	학교법인 이화학당	암 조직 선택성과 생분해성을 갖는폴리포스파젠-백금(ⅱ)착물 복합체 항암제 및 그 제조방법
WO2006091790A1 (en) *	2005-02-23	2006-08-31	Xenoport, Inc.	Platinum-containing compounds exhibiting cytostatic activity, synthesis and methods of use
RU2319491C1 (ru)	2006-07-12	2008-03-20	Бадулин Николай Александрович	Противоопухолевая, антибактериальная и антивирусная фармацевтическая композиция (ее варианты)
US8389506B2 (en) *	2007-12-07	2013-03-05	Prana Biotechnology Ltd.	Compounds for therapy and diagnosis
ES2704303T3 (es)	2010-08-24	2019-03-15	Dana Farber Cancer Inst Inc	Procedimientos para la predicción de una respuesta contra el cáncer
ES2768344T3 (es)	2011-06-17	2020-06-22	Myriad Genetics Inc	Métodos y materiales para evaluar el desequilibrio alélico
CN102863474A (zh)	2011-07-09	2013-01-09	陈小平	一类治疗细胞增殖性疾病的铂化合物、其制备方法和应用
CN102993239A (zh)	2011-09-19	2013-03-27	陈小平	离去基团含氨基或烷胺基的丁二酸衍生物的铂类化合物
CN103703011B (zh) *	2011-12-07	2016-06-22	北京市丰硕维康技术开发有限责任公司	一类离去基团是含氨基或烷氨基的羟基酸衍生物的铂类化合物及其制备方法和应用
JP6325453B2 (ja)	2011-12-21	2018-05-16	ミリアド・ジェネティックス・インコーポレイテッド	ヘテロ接合性の消失（ｌｏｓｓｏｆｈｅｔｅｒｏｚｙｇｏｓｉｔｙ）を評価するための方法および材料
ES2687024T3 (es)	2012-02-23	2018-10-23	Children's Medical Center Corporation	Procedimientos para predecir la respuesta contra el cáncer
CA2867434C (en)	2012-06-07	2021-10-12	Institut Curie	Methods for detecting inactivation of the homologous recombination pathway (brca1/2) in human tumors
US10308986B2 (en)	2013-03-14	2019-06-04	Children's Medical Center Corporation	Cancer diagnosis, treatment selection and treatment
BR112015031278B1 (pt)	2013-06-14	2022-05-17	Akamara Therapeutics, Inc	Compostos e nanopartículas de platina com base em lipídio, seus processos de preparação, composições farmacêuticas compreendendo os mesmos e seus usos no tratamento de câncer
WO2014203691A1 (ja) *	2013-06-18	2014-12-24	株式会社ヤクルト本社	白金錯体を含有する新規医薬
CA2931181C (en)	2013-12-09	2023-01-24	Institut Curie	Methods for detecting inactivation of the homologous recombination pathway (brca1/2) in human tumors
DK3686288T3 (da)	2014-08-15	2023-05-22	Myriad Genetics Inc	Fremgangsmåder og materialer til analyse af homolog rekombinationsdeficiens
EP3297681B1 (de)	2015-05-19	2022-03-16	Akamara Therapeutics, Inc.	Verfahren zur herstellung supramolekularer platinbasierter verbindungen
US20210137874A1 (en) *	2017-03-22	2021-05-13	The Regents Of The University Of California	Modified platinum compounds and therapeutic uses thereof

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4115418A (en) *	1976-09-02	1978-09-19	Government Of The United States Of America	1,2-diaminocyclohexane platinum (ii) complexes having antineoplastic activity
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
JPS57123198A (en) *	1981-01-23	1982-07-31	Shionogi & Co Ltd	Novel platinum complex
JPS5921697A (ja) *	1982-06-24	1984-02-03	Yoshinori Kitani	新規な白金錯体
US4673754A (en) *	1983-10-14	1987-06-16	Inco Alloys International, Inc.	Platinum and palladium complexes
IL73337A (en) *	1984-10-28	1988-09-30	Yissum Res Dev Co	Antitumor steroid-platinum complexes and method for the preparation thereof
US4587331A (en) *	1984-12-17	1986-05-06	American Cyanamid Company	Platinum complexes of polyhydroxylated alkylamines and 2-polyhydroxylated alkyl-1,2-diaminoethanes
EP0284197A1 (de) *	1987-02-20	1988-09-28	Tanabe Seiyaku Co., Ltd.	Organische Platinkomplexe und Verfahren zu deren Herstellung
JP2749092B2 (ja) *	1987-07-17	1998-05-13	ジョージタウン・ユニバーシティー	白金系医薬品

1989
- 1989-01-26 US US07/301,773 patent/US4946954A/en not_active Expired - Fee Related
1990
- 1990-01-16 PH PH39898A patent/PH26424A/en unknown
- 1990-01-17 EP EP19900902930 patent/EP0462980A4/en not_active Withdrawn
- 1990-01-17 JP JP2503681A patent/JP2771326B2/ja not_active Expired - Lifetime
- 1990-01-17 ZA ZA90336A patent/ZA90336B/xx unknown
- 1990-01-17 WO PCT/US1990/000171 patent/WO1990008157A1/en not_active Ceased
- 1990-01-17 IL IL9309090A patent/IL93090A/en not_active IP Right Cessation
- 1990-01-17 HU HU901456A patent/HUT59690A/hu unknown
- 1990-01-17 CA CA002045120A patent/CA2045120A1/en not_active Abandoned
- 1990-01-17 RU SU905001256A patent/RU2074861C1/ru active
- 1990-01-17 NZ NZ232134A patent/NZ232134A/en unknown
- 1990-01-17 AU AU50394/90A patent/AU5039490A/en not_active Abandoned
1991
- 1991-07-11 NO NO912732A patent/NO180588C/no unknown
1994
- 1994-01-31 AU AU54792/94A patent/AU674185B2/en not_active Ceased

Also Published As

Publication number	Publication date
JPH04502767A (ja)	1992-05-21
PH26424A (en)	1992-07-15
NO180588B (no)	1997-02-03
HUT59690A (en)	1992-06-29
NZ232134A (en)	1992-09-25
AU5479294A (en)	1994-03-31
WO1990008157A1 (en)	1990-07-26
EP0462980A1 (de)	1992-01-02
CA2045120A1 (en)	1990-07-18
IL93090A0 (en)	1990-11-05
AU5039490A (en)	1990-08-13
NO912732L (no)	1991-07-11
RU2074861C1 (ru)	1997-03-10
AU674185B2 (en)	1996-12-12
NO912732D0 (no)	1991-07-11
US4946954A (en)	1990-08-07
JP2771326B2 (ja)	1998-07-02
ZA90336B (en)	1990-10-31
EP0462980A4 (en)	1992-03-11
NO180588C (no)	1997-05-14

Legal Events

Date	Code	Title
1996-03-31	FF	Patent granted
1996-08-04	KB	Patent renewed
2000-11-21	KB	Patent renewed
2004-03-28	KB	Patent renewed
2008-02-10	KB	Patent renewed
2010-12-30	EXP	Patent expired

Publication	Publication Date	Title
US4946954A (en)	1990-08-07	Platinum pharmaceutical agents
JP2710654B2 (ja)	1998-02-10	１、２−ビス（アミノメチル）シクロブタン−白金錯化合物、その製造方法、該化合物を含有する抗腫瘍作用を有する薬剤およびその製造方法
US5434256A (en)	1995-07-18	Diamine platinum complexes as antitumor agents
EP0376518A1 (de)	1990-07-04	Phospholipide Nucleoside
US4617189A (en)	1986-10-14	Use of selenium-containing compounds for negating the toxic effects of platinum compounds used in chemotherapy, and a novel selenium-containing platinum compound and use thereof as an anti-cancer medicine
US4895936A (en)	1990-01-23	Platinum pharmaceuticals
US4956459A (en)	1990-09-11	Platinum compounds suitable for use as pharmaceuticals
CN101456881B (zh)	2012-10-17	木犀草素及其衍生物的铂类配合物、制备方法及其应用
US4895935A (en)	1990-01-23	Platinum pharmaceuticals
EP0376959B1 (de)	1993-03-24	Platin-arzneimittel
EP1968991B9 (de)	2012-08-08	Bisplatinkomplexe mit antitumorwirkung
CN1197798A (zh)	1998-11-04	新铂抗癌药物及合成
EP0214862B1 (de)	1991-03-13	Antitumor-Platinkomplexe, deren Herstellung und Verwendung
EP0310260A2 (de)	1989-04-05	Platin-Komplex und dessen Verwendung als Anti-Tumor-Agenzien
CA1274529A (en)	1990-09-25	Platinum(ii) complexes of 1,1-cyclobutane- dicarboxylate and process for their production
DE4041353A1 (de)	1992-06-25	Antineoplastisch wirkende platinkomplexe mit kronenethercarbonsaeure-verbindungen und diese enthaltende arzneimittel
JPS63307890A (ja)	1988-12-15	新規白金（２）錯体および悪性腫瘍治療剤
JPH04224596A (ja)	1992-08-13	白金錯体および抗腫瘍剤