JPH0523276B2 - - Google Patents
Info
- Publication number
- JPH0523276B2 JPH0523276B2 JP61152635A JP15263586A JPH0523276B2 JP H0523276 B2 JPH0523276 B2 JP H0523276B2 JP 61152635 A JP61152635 A JP 61152635A JP 15263586 A JP15263586 A JP 15263586A JP H0523276 B2 JPH0523276 B2 JP H0523276B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- present
- cisplatin
- water
- drug
- 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 - Lifetime
Links
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 32
- 229910052697 platinum Inorganic materials 0.000 claims description 13
- 150000004985 diamines Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 21
- 229960004316 cisplatin Drugs 0.000 description 21
- 229940079593 drug Drugs 0.000 description 18
- 239000003814 drug Substances 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 15
- 210000004881 tumor cell Anatomy 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 230000000259 anti-tumor effect Effects 0.000 description 12
- 231100000417 nephrotoxicity Toxicity 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 241000699666 Mus <mouse, genus> Species 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- 230000004083 survival effect Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000010998 test method Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 150000003057 platinum Chemical class 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- 239000002246 antineoplastic agent Substances 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical class OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 description 5
- 239000002895 emetic Substances 0.000 description 5
- 239000002504 physiological saline solution Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 231100000111 LD50 Toxicity 0.000 description 4
- 208000007093 Leukemia L1210 Diseases 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 4
- GGQJPAQXCYUEKB-RXMQYKEDSA-N (2r)-2-methylbutane-1,4-diamine Chemical compound NC[C@H](C)CCN GGQJPAQXCYUEKB-RXMQYKEDSA-N 0.000 description 3
- GGQJPAQXCYUEKB-UHFFFAOYSA-N 2-methylbutane-1,4-diamine Chemical compound NCC(C)CCN GGQJPAQXCYUEKB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- -1 silver halide Chemical class 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001647 drug administration Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000009422 growth inhibiting effect Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 description 1
- SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- GAYWCADKXYCKCG-UHFFFAOYSA-N 5-pyridin-3-yl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1NC(=S)N=C1C1=CC=CN=C1 GAYWCADKXYCKCG-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 238000011740 C57BL/6 mouse Methods 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- 208000008342 Leukemia P388 Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 description 1
- FHWFDHSUVNIGGR-UHFFFAOYSA-L [Pt](I)I.[K] Chemical compound [Pt](I)I.[K] FHWFDHSUVNIGGR-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- SYEOWUNSTUDKGM-UHFFFAOYSA-N beta-methyladipic acid Natural products OC(=O)CC(C)CCC(O)=O SYEOWUNSTUDKGM-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003560 cancer drug Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- BNJBUDJCJPWKRQ-UHFFFAOYSA-H dipotassium;hexaiodoplatinum(2-) Chemical compound [K+].[K+].[I-].[I-].[I-].[I-].[I-].[I-].[Pt+4] BNJBUDJCJPWKRQ-UHFFFAOYSA-H 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 231100000226 haematotoxicity Toxicity 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000711 polarimetry Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/893,108 US4737589A (en) | 1985-08-27 | 1986-08-04 | Platinum Complexes |
| DE8686306162T DE3667468D1 (de) | 1985-08-27 | 1986-08-08 | Platinkomplexe. |
| CA000515594A CA1258865A (en) | 1985-08-27 | 1986-08-08 | Platinum complexes |
| EP86306162A EP0219936B1 (en) | 1985-08-27 | 1986-08-08 | Novel platinum complexes |
| IL79819A IL79819A0 (en) | 1985-08-27 | 1986-08-24 | Novel platinum complexes |
| AU61801/86A AU595827B2 (en) | 1985-08-27 | 1986-08-25 | Novel platinum complexes |
| DK405986A DK405986A (da) | 1985-08-27 | 1986-08-26 | Platinkomplekser |
| ES8601351A ES2001586A6 (es) | 1985-08-27 | 1986-08-26 | Un procedimiento para producir un complejo de diamina platino (ii) |
| HU863688A HU198302B (en) | 1985-08-27 | 1986-08-26 | Process for producing new platine-komplexes and citostatice pharmaceuticalcompositions containing them as active components |
| IE228186A IE59225B1 (en) | 1985-08-27 | 1986-08-26 | Novel platinum complexes |
| CN 86105441 CN1010314B (zh) | 1985-08-27 | 1986-08-26 | 新型的铂配合物生产方法 |
| KR1019860007083A KR910009822B1 (ko) | 1985-08-27 | 1986-08-26 | 백금 착화합물의 제조방법 |
| CS622986A CS273618B2 (en) | 1985-08-27 | 1986-08-27 | Method of diamino-platinous complex preparation |
| US07/087,045 US4864043A (en) | 1985-08-27 | 1987-08-19 | Platinum complexes |
| US07/372,248 US4921984A (en) | 1985-08-27 | 1989-06-27 | Novel platinum complexes |
| US07/464,671 US5068376A (en) | 1985-08-27 | 1990-01-10 | Novel platinum complexes |
| JP4291914A JPH05345792A (ja) | 1986-07-01 | 1992-10-07 | 新規白金錯体 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60-187710 | 1985-08-27 | ||
| JP18771085 | 1985-08-27 | ||
| JP61-26800 | 1986-02-12 | ||
| JP61-26799 | 1986-02-12 | ||
| JP61-94626 | 1986-04-25 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4291914A Division JPH05345792A (ja) | 1986-07-01 | 1992-10-07 | 新規白金錯体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6345290A JPS6345290A (ja) | 1988-02-26 |
| JPH0523276B2 true JPH0523276B2 (hu) | 1993-04-02 |
Family
ID=16210812
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61152635A Granted JPS6345290A (ja) | 1985-08-27 | 1986-07-01 | 新規白金錯体 |
| JP19813986A Pending JPS6345291A (ja) | 1985-08-27 | 1986-08-26 | ジアミン白金錯体の製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19813986A Pending JPS6345291A (ja) | 1985-08-27 | 1986-08-26 | ジアミン白金錯体の製造方法 |
Country Status (2)
| Country | Link |
|---|---|
| JP (2) | JPS6345290A (hu) |
| ZA (1) | ZA866376B (hu) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008001851A1 (en) * | 2006-06-28 | 2008-01-03 | Ihi Corporation | Drug, drug induction device, magnetic detector and method of designing drug |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5716895A (en) * | 1980-07-05 | 1982-01-28 | Otsuka Chem Co Ltd | Platinum 2 complex and antitumor agent containing the same as active principle |
| US4410544A (en) * | 1978-07-06 | 1983-10-18 | Nederlandse Centrale Organisatie voor Toegespastnatuurwetenschappeliukond erzoek | Platinum-diamine complexes, a method for the preparation of a medicine using such a platinum-diamine complex for the treatment of malignant tumor in mice |
-
1986
- 1986-07-01 JP JP61152635A patent/JPS6345290A/ja active Granted
- 1986-08-22 ZA ZA866376A patent/ZA866376B/xx unknown
- 1986-08-26 JP JP19813986A patent/JPS6345291A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4410544A (en) * | 1978-07-06 | 1983-10-18 | Nederlandse Centrale Organisatie voor Toegespastnatuurwetenschappeliukond erzoek | Platinum-diamine complexes, a method for the preparation of a medicine using such a platinum-diamine complex for the treatment of malignant tumor in mice |
| JPS5716895A (en) * | 1980-07-05 | 1982-01-28 | Otsuka Chem Co Ltd | Platinum 2 complex and antitumor agent containing the same as active principle |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008001851A1 (en) * | 2006-06-28 | 2008-01-03 | Ihi Corporation | Drug, drug induction device, magnetic detector and method of designing drug |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6345291A (ja) | 1988-02-26 |
| ZA866376B (en) | 1987-04-29 |
| JPS6345290A (ja) | 1988-02-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0219936B1 (en) | Novel platinum complexes | |
| US4452812A (en) | Organic complex of platinum, its preparation and its use for treating malignant tumors | |
| CA1292749C (en) | Platinum complexes | |
| JPH036156B2 (hu) | ||
| EP0471709A1 (en) | RUTHENIUM (III) COMPLEXES AS ANTINEOPLASTIC AGENTS. | |
| KR890004350B1 (ko) | 글리콜산 백금 착체의 제조방법 | |
| EP0163316B1 (en) | Platinum-intercalative complexes for the treatment of cancer | |
| US4748254A (en) | Mixed carboxylato platinum (II) complexes | |
| CA2046313C (en) | Platinum (ii) complex and agent for treating malignant tumor | |
| JPH0523276B2 (hu) | ||
| EP0518645B1 (en) | Platinum (II) complex and antitumor agent | |
| JPWO2009090903A1 (ja) | 白金錯体化合物およびその利用 | |
| KR910009822B1 (ko) | 백금 착화합물의 제조방법 | |
| JPS61249993A (ja) | 新規有機白金錯体及びその製法 | |
| US5498780A (en) | Platinum complex and malignant tumor treating drug containing the same | |
| EP0310260A2 (en) | Platinum complexes and their use as anti-tumor agents | |
| EP0174114A1 (en) | Platinum complexes of ascorbic acid and ascorbic acid analogs | |
| JPH05345792A (ja) | 新規白金錯体 | |
| JPH02212497A (ja) | 新規白金錯体及びその製法 | |
| JPS63112591A (ja) | 新規白金錯体 | |
| JPS63284190A (ja) | 新規白金錯体 | |
| JPS6230792A (ja) | 新規白金錯体 | |
| JPS61286396A (ja) | 新規白金錯体およびその用途 | |
| JPH049393A (ja) | 新規白金錯体およびそれを有効成分とする腫瘍治療剤 | |
| JPH0469393A (ja) | 新規白金錯体およびそれを有効成分とする腫瘍治療剤 |