NO172585B - Analogifremgangsmaate for fremstilling av farmasoeytisk aktive fosfino-hydrocarbon-gruppe viii-metallkomplekser - Google Patents
Analogifremgangsmaate for fremstilling av farmasoeytisk aktive fosfino-hydrocarbon-gruppe viii-metallkomplekser Download PDFInfo
- Publication number
- NO172585B NO172585B NO864270A NO864270A NO172585B NO 172585 B NO172585 B NO 172585B NO 864270 A NO864270 A NO 864270A NO 864270 A NO864270 A NO 864270A NO 172585 B NO172585 B NO 172585B
- Authority
- NO
- Norway
- Prior art keywords
- bis
- diphenylphosphino
- sub
- preparation
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims description 13
- 229910052751 metal Inorganic materials 0.000 title description 7
- 239000002184 metal Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims abstract description 8
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims description 11
- -1 perchlorate compound Chemical class 0.000 claims description 7
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 6
- NIPPJMSKAOITEK-UHFFFAOYSA-N 2-diphenylarsanylethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CC[As](C=1C=CC=CC=1)C1=CC=CC=C1 NIPPJMSKAOITEK-UHFFFAOYSA-N 0.000 claims description 5
- FAFGMAGIYHHRKN-UHFFFAOYSA-N 2-diphenylphosphanylethyl(diphenyl)phosphane;palladium Chemical compound [Pd].C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 FAFGMAGIYHHRKN-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 3
- 239000004323 potassium nitrate Substances 0.000 claims description 3
- 235000010333 potassium nitrate Nutrition 0.000 claims description 3
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 3
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims description 3
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract description 5
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical group [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 abstract description 2
- 229910002651 NO3 Inorganic materials 0.000 abstract description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract description 2
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical group [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 150000002736 metal compounds Chemical class 0.000 abstract description 2
- 230000004565 tumor cell growth Effects 0.000 abstract description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical group [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052785 arsenic Inorganic materials 0.000 abstract 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 abstract 1
- WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical compound [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 abstract 1
- 210000004881 tumor cell Anatomy 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 230000000259 anti-tumor effect Effects 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 208000032839 leukemia Diseases 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 241001529936 Murinae Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 201000001441 melanoma Diseases 0.000 description 4
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 229960004316 cisplatin Drugs 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000003797 essential amino acid Substances 0.000 description 3
- 235000020776 essential amino acid Nutrition 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 208000001382 Experimental Melanoma Diseases 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- 229930182816 L-glutamine Natural products 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- NCKJIJSEWKIXAT-QURGRASLSA-N [(e)-2-diphenylphosphanylethenyl]-diphenylphosphane Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)/C=C/P(C=1C=CC=CC=1)C1=CC=CC=C1 NCKJIJSEWKIXAT-QURGRASLSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 229940054269 sodium pyruvate Drugs 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- UEFOAOSSGNBDOD-UHFFFAOYSA-N 2-diphenylphosphanylethyl(diphenyl)phosphane nickel(2+) dinitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 UEFOAOSSGNBDOD-UHFFFAOYSA-N 0.000 description 1
- VGZQMZRKQWICJF-UHFFFAOYSA-L 2-diphenylphosphanylethyl(diphenyl)phosphane nickel(2+) diperchlorate Chemical compound [Ni+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 VGZQMZRKQWICJF-UHFFFAOYSA-L 0.000 description 1
- ZAAWXKZFQQMGIX-UHFFFAOYSA-K 2-diphenylphosphanylethyl(diphenyl)phosphane;trichlororhodium Chemical compound Cl[Rh](Cl)Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 ZAAWXKZFQQMGIX-UHFFFAOYSA-K 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- 239000006145 Eagle's minimal essential medium Substances 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
- HCFYRCFGZZIACS-UHFFFAOYSA-N [Cu+].[Cu+].C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Cu+].[Cu+].C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 HCFYRCFGZZIACS-UHFFFAOYSA-N 0.000 description 1
- WLMOAHYOHOSOHO-UHFFFAOYSA-N [Ir+].C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical class [Ir+].C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 WLMOAHYOHOSOHO-UHFFFAOYSA-N 0.000 description 1
- NPYSLKQMBBQALU-UHFFFAOYSA-M [Ir]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Ir]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 NPYSLKQMBBQALU-UHFFFAOYSA-M 0.000 description 1
- YFPUSLTXUGMXLL-UHFFFAOYSA-M [Rh]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [Rh]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 YFPUSLTXUGMXLL-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- RBYGDVHOECIAFC-UHFFFAOYSA-L acetonitrile;palladium(2+);dichloride Chemical compound [Cl-].[Cl-].[Pd+2].CC#N.CC#N RBYGDVHOECIAFC-UHFFFAOYSA-L 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- UMWYYMCOBYVEPY-UHFFFAOYSA-N azanide;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2] UMWYYMCOBYVEPY-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- UIBPVOHCUYIKFM-UHFFFAOYSA-N cobalt(2+) 2-diphenylphosphanylethyl(diphenyl)phosphane Chemical class [Co+2].C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 UIBPVOHCUYIKFM-UHFFFAOYSA-N 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- FYWYMUFSLOEHHJ-UHFFFAOYSA-L dibromocobalt;2-diphenylphosphanylethyl(diphenyl)phosphane Chemical compound Br[Co]Br.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 FYWYMUFSLOEHHJ-UHFFFAOYSA-L 0.000 description 1
- KETAVDRXXNKYKF-UHFFFAOYSA-L dichlorocobalt;2-diphenylphosphanylethyl(diphenyl)phosphane Chemical compound Cl[Co]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 KETAVDRXXNKYKF-UHFFFAOYSA-L 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- ZBKIUFWVEIBQRT-UHFFFAOYSA-N gold(1+) Chemical compound [Au+] ZBKIUFWVEIBQRT-UHFFFAOYSA-N 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical class [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- IXGNPUSUVRTQGW-UHFFFAOYSA-M sodium;perchlorate;hydrate Chemical compound O.[Na+].[O-]Cl(=O)(=O)=O IXGNPUSUVRTQGW-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TYLYVJBCMQFRCB-UHFFFAOYSA-K trichlororhodium;trihydrate Chemical compound O.O.O.[Cl-].[Cl-].[Cl-].[Rh+3] TYLYVJBCMQFRCB-UHFFFAOYSA-K 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
-
- 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
- C07F15/0033—Iridium compounds
- C07F15/004—Iridium compounds without a metal-carbon linkage
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07F15/006—Palladium compounds
- C07F15/0066—Palladium compounds without a metal-carbon linkage
-
- 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
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
-
- 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
-
- 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
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- 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
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
-
- 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
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8502929A NL8502929A (nl) | 1985-10-25 | 1985-10-25 | Groep viii-overgangsmetaal-complexen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een geneesmiddel met toepassing van een dergelijke groep viii-overgangsmetaal-complex voor de behandeling van kanker, alsmede aldus verkregen gevormd geneesmiddel. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO864270D0 NO864270D0 (no) | 1986-10-24 |
| NO864270L NO864270L (no) | 1987-04-27 |
| NO172585B true NO172585B (no) | 1993-05-03 |
Family
ID=19846766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO864270A NO172585B (no) | 1985-10-25 | 1986-10-24 | Analogifremgangsmaate for fremstilling av farmasoeytisk aktive fosfino-hydrocarbon-gruppe viii-metallkomplekser |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4831170A (el) |
| EP (1) | EP0227127B1 (el) |
| JP (1) | JPS62161795A (el) |
| KR (1) | KR870003787A (el) |
| CN (3) | CN86107219A (el) |
| AT (1) | ATE63122T1 (el) |
| AU (1) | AU601954B2 (el) |
| CA (1) | CA1269395A (el) |
| DE (1) | DE3679045D1 (el) |
| DK (1) | DK511786A (el) |
| ES (1) | ES2039199T3 (el) |
| FI (1) | FI85861C (el) |
| GR (1) | GR3001910T3 (el) |
| HU (2) | HU203557B (el) |
| IL (1) | IL80416A0 (el) |
| NL (1) | NL8502929A (el) |
| NO (1) | NO172585B (el) |
| NZ (1) | NZ218072A (el) |
| PT (1) | PT83612B (el) |
| YU (1) | YU45802B (el) |
| ZA (1) | ZA868162B (el) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1378240T3 (da) * | 1997-10-15 | 2008-12-08 | Polarx Biopharmaceuticals Inc | Farmaceutiske præparater omfattende arsentrioxid til behandling af multipelt myelom |
| JP5015451B2 (ja) * | 2005-04-18 | 2012-08-29 | 日本化学工業株式会社 | ホスフィン遷移金属錯体、その製造方法およびそれを含有する抗癌剤 |
| WO2009081366A1 (en) * | 2007-12-20 | 2009-07-02 | Richard John Bowen | Palladium and platinum phosphine complexes and their use as anti-tumour agents |
| WO2009104167A1 (en) * | 2008-02-22 | 2009-08-27 | Mintek | A substance or composition for the treatment of cancer |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3084179A (en) * | 1959-02-27 | 1963-04-02 | Ici Ltd | Phosphorous-containing-ligand stabilized transition metal compounds |
| US3345392A (en) * | 1964-03-24 | 1967-10-03 | American Cyanamid Co | Organophosphorus-copper complex compounds |
| GB1085762A (en) * | 1965-04-30 | 1967-10-04 | Ici Ltd | Complex organic iridium compounds and their use as catalysts |
| FR2116905A5 (fr) * | 1970-12-10 | 1972-07-21 | Inst Francais Du Petrole | Nouveaux coordinats bidentes,leur fabrication et leurs applications |
| US3939188A (en) * | 1972-03-24 | 1976-02-17 | Exxon Research And Engineering Company | Preparation of zerovalent phosphine substituted rhodium compounds and their use in the selective carbonylation of olefins |
| US3954821A (en) * | 1975-06-30 | 1976-05-04 | E. I. Du Pont De Nemours And Company | Carbon dioxide complexes of Rh, Ir, Ni, Pd, and Pt |
| US4268454A (en) * | 1978-12-21 | 1981-05-19 | Allied Chemical Corporation | Anionic group VIII metal hydride catalysts |
| US4302401A (en) * | 1980-01-23 | 1981-11-24 | Exxon Research & Engineering Co. | Tetraalkyl phosphonium substituted phosphine and amine transition metal complexes |
| US4331818A (en) * | 1980-03-19 | 1982-05-25 | The Procter & Gamble Company | Chiral phospine ligand |
| CA1238854A (en) * | 1984-02-01 | 1988-07-05 | David T. Hill | ANTITUMOR PHARMACEUTICAL COMPOSITIONS AND METHODS FOR TREATING TUMORS EMPLOYING ¬.alpha.,W- BIS(DISUBSTITUTEDPHOSPHINO)HYDROCARBON| DIGOLD (I) DIGOLD (III), DISILVER (I) AND DICOPPER (I) DERIVATIVES |
| PH21350A (en) * | 1984-06-04 | 1987-10-13 | Smithkline Beckman Corp | Tumor cell growth imhibiting pharmaceutical compositions containing phosphino-hydrocarbon-gold, silver or copper complexes |
-
1985
- 1985-10-25 NL NL8502929A patent/NL8502929A/nl not_active Application Discontinuation
-
1986
- 1986-10-23 DE DE8686201853T patent/DE3679045D1/de not_active Expired - Fee Related
- 1986-10-23 AT AT86201853T patent/ATE63122T1/de not_active IP Right Cessation
- 1986-10-23 EP EP86201853A patent/EP0227127B1/en not_active Expired - Lifetime
- 1986-10-23 ES ES198686201853T patent/ES2039199T3/es not_active Expired - Lifetime
- 1986-10-24 US US06/922,655 patent/US4831170A/en not_active Expired - Fee Related
- 1986-10-24 IL IL80416A patent/IL80416A0/xx unknown
- 1986-10-24 NO NO864270A patent/NO172585B/no unknown
- 1986-10-24 YU YU181786A patent/YU45802B/sh unknown
- 1986-10-24 PT PT83612A patent/PT83612B/pt not_active IP Right Cessation
- 1986-10-24 HU HU903471A patent/HU203557B/hu not_active IP Right Cessation
- 1986-10-24 CA CA000521403A patent/CA1269395A/en not_active Expired - Fee Related
- 1986-10-24 HU HU864487A patent/HU200609B/hu not_active IP Right Cessation
- 1986-10-24 DK DK511786A patent/DK511786A/da not_active Application Discontinuation
- 1986-10-24 FI FI864327A patent/FI85861C/fi not_active IP Right Cessation
- 1986-10-25 JP JP61252843A patent/JPS62161795A/ja active Pending
- 1986-10-25 CN CN198686107219A patent/CN86107219A/zh active Pending
- 1986-10-25 KR KR1019860008963A patent/KR870003787A/ko not_active Application Discontinuation
- 1986-10-27 AU AU64413/86A patent/AU601954B2/en not_active Ceased
- 1986-10-27 ZA ZA868162A patent/ZA868162B/xx unknown
- 1986-10-28 NZ NZ218072A patent/NZ218072A/en unknown
-
1991
- 1991-03-16 CN CN91101598A patent/CN1057962A/zh active Pending
- 1991-05-03 GR GR91400587T patent/GR3001910T3/el unknown
-
1992
- 1992-05-28 CN CN92104058A patent/CN1067430A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PT83612A (en) | 1986-11-01 |
| AU601954B2 (en) | 1990-09-27 |
| HUT44263A (en) | 1988-02-29 |
| NO864270L (no) | 1987-04-27 |
| YU45802B (sh) | 1992-07-20 |
| IL80416A0 (en) | 1987-01-30 |
| HU203557B (en) | 1991-08-28 |
| CA1269395A (en) | 1990-05-22 |
| GR3001910T3 (en) | 1992-11-23 |
| DK511786A (da) | 1987-04-26 |
| JPS62161795A (ja) | 1987-07-17 |
| NO864270D0 (no) | 1986-10-24 |
| EP0227127A3 (en) | 1988-09-07 |
| CN1067430A (zh) | 1992-12-30 |
| FI864327A0 (fi) | 1986-10-24 |
| EP0227127A2 (en) | 1987-07-01 |
| NZ218072A (en) | 1990-12-21 |
| ATE63122T1 (de) | 1991-05-15 |
| ES2039199T3 (es) | 1993-09-16 |
| FI85861B (fi) | 1992-02-28 |
| FI85861C (fi) | 1992-06-10 |
| NL8502929A (nl) | 1987-05-18 |
| DK511786D0 (da) | 1986-10-24 |
| YU181786A (en) | 1988-02-29 |
| AU6441386A (en) | 1987-05-21 |
| CN1057962A (zh) | 1992-01-22 |
| US4831170A (en) | 1989-05-16 |
| FI864327A (fi) | 1987-04-26 |
| CN86107219A (zh) | 1987-05-27 |
| EP0227127B1 (en) | 1991-05-02 |
| HU903471D0 (en) | 1990-12-28 |
| KR870003787A (ko) | 1987-05-04 |
| HU200609B (en) | 1990-07-28 |
| ZA868162B (en) | 1987-06-24 |
| PT83612B (pt) | 1989-05-31 |
| DE3679045D1 (de) | 1991-06-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4562275A (en) | Antitumor platinum complexes | |
| US4200583A (en) | New platinum complex | |
| US4845124A (en) | Platinum (IV) complexes | |
| US5194645A (en) | Trans-pt (iv) compounds | |
| US5091521A (en) | Cis-platinum complexes, a process for the preparation thereof, and pharmaceuticals containing these compounds | |
| US4902797A (en) | Ammine-alicyclic amine-platinum complexes and antitumor agents | |
| US5318962A (en) | Water soluble 1,2-diaminocyclohexane platinum (IV) complexes as antitumor agents | |
| US4234500A (en) | Ethylenediamine platinum(II) and 1,2-diamino-cyclohexane platinum(II) pyrophosphate complexes | |
| KR910009823B1 (ko) | 백금착물(白金錯物) | |
| Bravo et al. | First heterobimetallic Cu (i)–dppf complexes designed for anticancer applications: synthesis, structural characterization and cytotoxicity | |
| GB2053212A (en) | Cis-platinum(ii)amine lactate complexes | |
| US5132323A (en) | 1,2-diaminocyclohexane-platinum complexes with antitumor activity | |
| EP0115929A1 (en) | Novel organic platinum complex and process for the preparation thereof | |
| NO172585B (no) | Analogifremgangsmaate for fremstilling av farmasoeytisk aktive fosfino-hydrocarbon-gruppe viii-metallkomplekser | |
| US4291027A (en) | Method for treating tumors with ethylenediamine platinum (II) and 1,2-diaminocyclohexane-platinum (II) pyrophosphate complexes | |
| EP0232784B1 (en) | (gem-heterocyclodimethanamine-n,n')platinum complexes | |
| Barbanente et al. | One‐pot synthesis of new organometallic compounds with platinum‐carbon bond | |
| Khokhar et al. | Synthesis and antitumor activity of N-substituted iminodiacetato (1, 1-bis [aminomethyl] cyclohexane) platinum (II) complexes | |
| KR940010297B1 (ko) | 신규한 플라티늄(ii) 착화합물과 그의 제조방법 | |
| Jeragh | Synthetic and kinetic studies of some transition metal complexes of macrocyclic ligands | |
| JPS61148187A (ja) | 新規白金錯体 | |
| JPS6222793A (ja) | 新規な有機白金錯体、その製法並びに該錯体を有効成分とする抗腫瘍剤 |