DE3586759T2 - Antitumor-platin-komplexe. - Google Patents
Antitumor-platin-komplexe.Info
- Publication number
- DE3586759T2 DE3586759T2 DE8888105817T DE3586759T DE3586759T2 DE 3586759 T2 DE3586759 T2 DE 3586759T2 DE 8888105817 T DE8888105817 T DE 8888105817T DE 3586759 T DE3586759 T DE 3586759T DE 3586759 T2 DE3586759 T2 DE 3586759T2
- Authority
- DE
- Germany
- Prior art keywords
- complexes
- complex
- trans
- platinum
- mice
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 239000003446 ligand Substances 0.000 claims description 23
- -1 alkali metal salt Chemical class 0.000 claims description 5
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 claims description 5
- HNUKTDKISXPDPA-UHFFFAOYSA-N 2-oxopropyl Chemical compound [CH2]C(C)=O HNUKTDKISXPDPA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 2
- 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 claims description 2
- 230000000259 anti-tumor effect Effects 0.000 abstract description 18
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical class [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 abstract description 13
- 241000699670 Mus sp. Species 0.000 description 24
- 206010028980 Neoplasm Diseases 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 15
- 229960004316 cisplatin Drugs 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 208000032839 leukemia Diseases 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 125000003963 dichloro group Chemical group Cl* 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000003057 platinum Chemical class 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 201000009030 Carcinoma Diseases 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 5
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 5
- 208000001382 Experimental Melanoma Diseases 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- JDPOGMLCKVQEPW-UHFFFAOYSA-N 1-(aminomethyl)cyclooctan-1-amine Chemical compound NCC1(N)CCCCCCC1 JDPOGMLCKVQEPW-UHFFFAOYSA-N 0.000 description 3
- JIWVNNBIBQCVCD-UHFFFAOYSA-N 2,4-dimethylpentane-1,2-diamine Chemical compound CC(C)CC(C)(N)CN JIWVNNBIBQCVCD-UHFFFAOYSA-N 0.000 description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 3
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000282339 Mustela Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 206010047700 Vomiting Diseases 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- PPLRXDIWGSZQDO-UHFFFAOYSA-L cyclohexane-1,2-diamine;dichloroplatinum(2+) Chemical compound Cl[Pt+2]Cl.NC1CCCCC1N PPLRXDIWGSZQDO-UHFFFAOYSA-L 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000002895 emetic Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229950006191 gluconic acid Drugs 0.000 description 3
- 235000012208 gluconic acid Nutrition 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002513 implantation Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 231100000225 lethality Toxicity 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 150000003058 platinum compounds Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 238000002054 transplantation Methods 0.000 description 3
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 238000011740 C57BL/6 mouse Methods 0.000 description 2
- 238000011765 DBA/2 mouse Methods 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000095 emetic effect Effects 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 229910052740 iodine Chemical group 0.000 description 2
- 201000005296 lung carcinoma Diseases 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 238000011269 treatment regimen Methods 0.000 description 2
- VATRZIAOBDOSNN-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoic acid;sodium Chemical compound [Na].OC(=O)C(F)(F)C(F)(F)C(F)(F)F VATRZIAOBDOSNN-UHFFFAOYSA-N 0.000 description 1
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 101100005765 Arabidopsis thaliana CDF1 gene Proteins 0.000 description 1
- 101100007579 Arabidopsis thaliana CPP1 gene Proteins 0.000 description 1
- 238000011725 BALB/c mouse Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000032974 Gagging Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000282341 Mustela putorius furo Species 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 206010061481 Renal injury Diseases 0.000 description 1
- 206010038776 Retching Diseases 0.000 description 1
- 101100218590 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) BDF2 gene Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 108010046334 Urease Proteins 0.000 description 1
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical class OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- SGLJYTWMWIAGEU-UHFFFAOYSA-N cyclohexane-1,2-diamine;platinum(2+) Chemical class [Pt+2].NC1CCCCC1N SGLJYTWMWIAGEU-UHFFFAOYSA-N 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000013101 initial test Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229940028435 intralipid Drugs 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 108700039855 mouse a Proteins 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
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 description 1
- XEEVLJKYYUVTRC-UHFFFAOYSA-N oxomalonic acid Chemical compound OC(=O)C(=O)C(O)=O XEEVLJKYYUVTRC-UHFFFAOYSA-N 0.000 description 1
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- NFOHLBHARAZXFQ-UHFFFAOYSA-L platinum(2+);dihydroxide Chemical compound O[Pt]O NFOHLBHARAZXFQ-UHFFFAOYSA-L 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
- 230000008673 vomiting 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/592,987 US4562275A (en) | 1984-03-23 | 1984-03-23 | Antitumor platinum complexes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3586759D1 DE3586759D1 (de) | 1992-11-19 |
| DE3586759T2 true DE3586759T2 (de) | 1993-03-04 |
Family
ID=24372887
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8888105817T Expired - Fee Related DE3586759T2 (de) | 1984-03-23 | 1985-03-22 | Antitumor-platin-komplexe. |
| DE8989100585T Expired - Fee Related DE3586059D1 (de) | 1984-03-23 | 1985-03-22 | Antitumor-platin-komplexe. |
| DE8585103438T Expired - Fee Related DE3574702D1 (de) | 1984-03-23 | 1985-03-22 | Antitumor-platin-komplexe. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8989100585T Expired - Fee Related DE3586059D1 (de) | 1984-03-23 | 1985-03-22 | Antitumor-platin-komplexe. |
| DE8585103438T Expired - Fee Related DE3574702D1 (de) | 1984-03-23 | 1985-03-22 | Antitumor-platin-komplexe. |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US4562275A (enExample) |
| EP (3) | EP0306605B1 (enExample) |
| JP (3) | JPS60209595A (enExample) |
| AT (3) | ATE81506T1 (enExample) |
| DE (3) | DE3586759T2 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4739087A (en) * | 1985-01-10 | 1988-04-19 | Bristol-Myers Company | Antineoplastic platinum complexes |
| NO860509L (no) * | 1985-02-23 | 1986-08-25 | Asta Werke Ag Chem Fab | Tumorhemmende (1,2-difenyl-etylendiamin)-platin(ii)-komplekser. |
| ZA86704B (en) * | 1985-02-23 | 1986-10-29 | Asta Werke Ag Chem Fab | Tumor retarding(1-benzyl-ethylenediamine9-platin(ii)-complexes |
| US4737589A (en) * | 1985-08-27 | 1988-04-12 | Nippon Kayaku Kabushiki Kaisha | Platinum Complexes |
| JPS6310725A (ja) * | 1986-03-11 | 1988-01-18 | Chugai Pharmaceut Co Ltd | 新規白金錯体化合物を有効成分として含有する制癌剤 |
| JPS6310724A (ja) * | 1986-03-11 | 1988-01-18 | Chugai Pharmaceut Co Ltd | 新規白金錯体を有効成分として含有する制癌剤 |
| US5011959A (en) * | 1986-11-17 | 1991-04-30 | The Board Of Regents, The University Of Texas System | 1,2-diaminocyclohexane-platinum complexes with antitumor activity |
| JPS63203692A (ja) * | 1987-02-19 | 1988-08-23 | Nippon Kayaku Co Ltd | 新規白金錯体 |
| US5256653A (en) * | 1987-02-19 | 1993-10-26 | Henkel Kommanditgesellschaft Auf Aktien | Pharmaceutical preparations containing platinum complexes/phosphonic acid liquid and processes for their use |
| DE3889327D1 (de) | 1987-02-19 | 1994-06-01 | Asta Medica Ag | Platinkomplexe enthaltende arzneimittel. |
| EP0290169A3 (en) * | 1987-05-04 | 1990-08-01 | Engelhard Corporation | Diamineplatinum complexes with phosphonocarboxylate and substituted phosphonocarboxylate ligands as antitumor agents |
| US4870070A (en) * | 1987-08-10 | 1989-09-26 | American Cyanamid Company | Water soluble platinum complexes of novel malonate derivatives |
| US4904809A (en) * | 1987-09-25 | 1990-02-27 | Ss Pharmaceutical Co., Ltd. | Platinum complex |
| EP0386243A4 (en) * | 1987-11-06 | 1990-10-10 | Sagami Chemical Research Center | Platinum (ii) complexes |
| JPH0762023B2 (ja) * | 1987-11-06 | 1995-07-05 | 財団法人相模中央化学研究所 | 白金配位化合物 |
| JPH01165593A (ja) * | 1987-12-21 | 1989-06-29 | Toray Ind Inc | 新規白金（２）錯体および悪性腫瘍治療剤 |
| SU1685944A1 (ru) * | 1988-06-06 | 1991-10-23 | Институт Физической Химии Им.Л.В.Писаржевского | Способ получени комплексного соединени платины (II) с высокомолекул рной н-ДНК из селезенки крупного рогатого скота марки А, обладающего противоопухолевой активностью |
| US5187193A (en) * | 1988-09-12 | 1993-02-16 | University Of Rochester | Method for stimulating transplanted bone marrow cells |
| US5035878A (en) * | 1988-09-12 | 1991-07-30 | University Of Rochester | Use of dithiocarbamates to counteract myelosuppression |
| US5294430A (en) * | 1988-09-12 | 1994-03-15 | University Of Rochester | Use of dithiocarbamates to treat myelosuppression |
| US5393909A (en) * | 1988-11-22 | 1995-02-28 | Board Of Regents, The University Of Texas System | Diamine platinum complexes as antitumor agents |
| US5225207A (en) * | 1989-03-17 | 1993-07-06 | Laboratoire Roger Bellon | Complexes derived from platinum, their preparation and the pharmaceutical compositions which contain them |
| FR2644458B1 (fr) * | 1989-03-17 | 1991-07-05 | Bellon Labor Sa Roger | Nouveaux complexes derives du platine, leur preparation et les compositions pharmaceutiques qui les contiennent |
| US4994591A (en) * | 1989-06-02 | 1991-02-19 | The Research Foundation Of State University Of Ny | Platinum complexes derived from b-silyamines |
| US5302587A (en) * | 1989-12-12 | 1994-04-12 | Toray Industries, Inc. | Platinum (II) complex and agent for treating malignant tumor |
| IT1238078B (it) * | 1990-01-31 | 1993-07-05 | Silvano Spinelli | Cis-platino complessi con ammine e sulfinilcarbossilati chelanti |
| US5216352A (en) * | 1990-11-29 | 1993-06-01 | Square D Company | Solid state current controlled interruption system |
| FR2683529B1 (fr) * | 1991-11-12 | 1994-02-04 | Bretagne Occidentale Universite | Composes pharmaceutiques gem-diphosphonates analogues du cis-platine. |
| FR2691151A1 (fr) * | 1992-05-14 | 1993-11-19 | Bellon Labor Sa Roger | Nouveaux dérivés du platine (IV), leur préparation et les compositions pharmaceutiques qui les contiennent. |
| CN1039588C (zh) * | 1995-03-29 | 1998-08-26 | 邹娟 | 新的抗肿瘤铂络合物 |
| EP0768315A4 (en) * | 1995-04-25 | 1998-12-30 | Toray Industries | METHOD FOR PRODUCING PLATIN (II) COMPLEXES |
| WO2008109417A1 (en) * | 2007-03-02 | 2008-09-12 | Case Western Reserve University | Mgmt inhibitor combinations for the treatment of neoplastic disorders |
| 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 |
| AUPQ641100A0 (en) * | 2000-03-23 | 2000-04-15 | Australia Nuclear Science & Technology Organisation | Methods of synthesis and use of radiolabelled platinum chemotherapeutic ag ents |
| JP5096657B2 (ja) * | 2000-08-11 | 2012-12-12 | 大日本住友製薬株式会社 | シスプラチン耐性癌治療剤 |
| WO2002028802A2 (en) | 2000-10-06 | 2002-04-11 | 3M Innovative Properties Company | Ceramic aggregate particles |
| DE60141700D1 (de) | 2000-10-16 | 2010-05-12 | 3M Innovative Properties Co | Atteilchen |
| CN1315972C (zh) | 2000-10-16 | 2007-05-16 | 3M创新有限公司 | 制造团聚颗粒的方法 |
| US6645624B2 (en) | 2000-11-10 | 2003-11-11 | 3M Innovative Properties Company | Composite abrasive particles and method of manufacture |
| US7858230B2 (en) | 2005-10-26 | 2010-12-28 | The Gillette Company | Battery cathodes |
| WO2014028653A1 (en) | 2012-08-14 | 2014-02-20 | Northwestern University | Arsenoplatin anti-cancer agents |
| US9499574B2 (en) | 2012-08-14 | 2016-11-22 | Northwestern University | Arsenoplatin anti-cancer agents |
| EP4220769A4 (en) | 2020-09-25 | 2025-05-21 | Tohoku University | Lithium-ion secondary battery negative electrode mixture and lithium-ion secondary battery |
Family Cites Families (19)
| 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 |
| JPS6041077B2 (ja) * | 1976-09-06 | 1985-09-13 | 喜徳 喜谷 | １，２‐ジアミノシクロヘキサン異性体のシス白金（２）錯体 |
| US4206226A (en) * | 1977-08-29 | 1980-06-03 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Use of 4-carboxy-phthalato-(1,2-diaminocyclohexane)-platinum(II) and alkali metal salts thereof in alleviating L1210 murine leukemia |
| US4137248A (en) * | 1977-08-29 | 1979-01-30 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Compound, 4-carboxyphthalato(1,2-diaminocyclohexane)-platinum(II) and alkali metal salts thereof |
| JPS5829957B2 (ja) * | 1977-09-12 | 1983-06-25 | 喜徳 喜谷 | 新規な白金錯体 |
| US4203912A (en) * | 1977-10-19 | 1980-05-20 | Johnson, Matthey & Co., Limited | Compositions containing platinum |
| SE7903361L (sv) * | 1978-04-20 | 1979-10-21 | Johnson Matthey Co Ltd | Kompositioner innehallande platina |
| NL7807334A (nl) * | 1978-07-06 | 1980-01-08 | Tno | Platina-diaminecomplexen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een genees- middel met toepassing van een dergelijk platina-dia- minecomplex voor de behandeling van kanker, alsmede al- dus verkregen gevormd geneesmiddel. |
| JPS6034958B2 (ja) * | 1978-09-02 | 1985-08-12 | 喜徳 喜谷 | 新規白金錯体 |
| US4234500A (en) * | 1979-03-07 | 1980-11-18 | Engelhard Minerals & Chemicals Corporation | Ethylenediamine platinum(II) and 1,2-diamino-cyclohexane platinum(II) pyrophosphate complexes |
| US4271085A (en) * | 1979-06-20 | 1981-06-02 | Engelhard Minerals & Chemicals Corporation | Cis-platinum (II) amine lactate complexes |
| 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 |
| GR75598B (enExample) * | 1980-04-29 | 1984-08-01 | Sanofi Sa | |
| JPS56154493A (en) * | 1980-04-30 | 1981-11-30 | Shionogi & Co Ltd | Novel platinum complex |
| JPS5716895A (en) * | 1980-07-05 | 1982-01-28 | Otsuka Chem Co Ltd | Platinum 2 complex and antitumor agent containing the same as active principle |
| JPS57123198A (en) * | 1981-01-23 | 1982-07-31 | Shionogi & Co Ltd | Novel platinum complex |
| NL8101026A (nl) * | 1981-03-03 | 1982-10-01 | Tno | Platinadiamine-complexen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een geneesmiddel met toepassing van een dergelijk platinadiamine-complex voor de behandeling van kanker alsmede aldus verkregen gevormd geneesmiddel. |
| JPS5879994A (ja) * | 1981-11-06 | 1983-05-13 | Shionogi & Co Ltd | 新規アダマンタン白金錯体 |
| JPS58124797A (ja) * | 1982-01-20 | 1983-07-25 | Shionogi & Co Ltd | 新規１，２−シクロヘキサンジアミン白金錯体 |
-
1984
- 1984-03-23 US US06/592,987 patent/US4562275A/en not_active Expired - Fee Related
-
1985
- 1985-03-22 DE DE8888105817T patent/DE3586759T2/de not_active Expired - Fee Related
- 1985-03-22 EP EP88105817A patent/EP0306605B1/en not_active Expired - Lifetime
- 1985-03-22 AT AT88105817T patent/ATE81506T1/de not_active IP Right Cessation
- 1985-03-22 JP JP60057687A patent/JPS60209595A/ja active Granted
- 1985-03-22 EP EP85103438A patent/EP0155705B1/en not_active Expired
- 1985-03-22 AT AT85103438T patent/ATE48605T1/de not_active IP Right Cessation
- 1985-03-22 DE DE8989100585T patent/DE3586059D1/de not_active Expired - Fee Related
- 1985-03-22 EP EP89100585A patent/EP0318464B1/en not_active Expired - Lifetime
- 1985-03-22 AT AT89100585T patent/ATE76078T1/de not_active IP Right Cessation
- 1985-03-22 DE DE8585103438T patent/DE3574702D1/de not_active Expired - Fee Related
- 1985-09-30 US US06/781,629 patent/US4594418A/en not_active Expired - Fee Related
- 1985-12-02 JP JP60271276A patent/JPS61171494A/ja active Granted
- 1985-12-02 JP JP60271275A patent/JPS61171493A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0318464B1 (en) | 1992-05-13 |
| EP0155705A2 (en) | 1985-09-25 |
| ATE48605T1 (de) | 1989-12-15 |
| ATE81506T1 (de) | 1992-10-15 |
| DE3586759D1 (de) | 1992-11-19 |
| US4562275A (en) | 1985-12-31 |
| EP0155705B1 (en) | 1989-12-13 |
| JPS61171493A (ja) | 1986-08-02 |
| DE3574702D1 (de) | 1990-01-18 |
| EP0318464A2 (en) | 1989-05-31 |
| EP0306605B1 (en) | 1992-10-14 |
| US4594418A (en) | 1986-06-10 |
| JPH0244838B2 (enExample) | 1990-10-05 |
| ATE76078T1 (de) | 1992-05-15 |
| JPS60209595A (ja) | 1985-10-22 |
| EP0318464A3 (en) | 1989-11-15 |
| EP0306605A1 (en) | 1989-03-15 |
| JPH0244836B2 (enExample) | 1990-10-05 |
| JPH0244837B2 (enExample) | 1990-10-05 |
| EP0155705A3 (en) | 1986-04-02 |
| DE3586059D1 (de) | 1992-06-17 |
| JPS61171494A (ja) | 1986-08-02 |
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |