CH658244A5 - Neue platinverbindungen und verfahren zu ihrer herstellung sowie verfahren zur herstellung von sie enthaltenden medizinischen zubereitungen zur behandlung von krebs. - Google Patents
Neue platinverbindungen und verfahren zu ihrer herstellung sowie verfahren zur herstellung von sie enthaltenden medizinischen zubereitungen zur behandlung von krebs. Download PDFInfo
- Publication number
- CH658244A5 CH658244A5 CH5718/83A CH571883A CH658244A5 CH 658244 A5 CH658244 A5 CH 658244A5 CH 5718/83 A CH5718/83 A CH 5718/83A CH 571883 A CH571883 A CH 571883A CH 658244 A5 CH658244 A5 CH 658244A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- platinum
- compound
- diamine complex
- corresponds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 38
- 206010028980 Neoplasm Diseases 0.000 title claims description 13
- 201000011510 cancer Diseases 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 229940045985 antineoplastic platinum compound Drugs 0.000 title description 2
- 150000003058 platinum compounds Chemical class 0.000 title description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 49
- 229910052697 platinum Inorganic materials 0.000 claims description 38
- -1 Platinum (II) diamine Chemical class 0.000 claims description 36
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 9
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical group OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical group OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- DDRVFRXYTKAZHH-UHFFFAOYSA-N 2-carboxyoxycarbonylbenzoic acid Chemical group OC(=O)OC(=O)C1=CC=CC=C1C(O)=O DDRVFRXYTKAZHH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 229910001961 silver nitrate Inorganic materials 0.000 claims 2
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical group CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 208000032839 leukemia Diseases 0.000 description 26
- 239000000203 mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 8
- 231100000417 nephrotoxicity Toxicity 0.000 description 8
- 229910021607 Silver chloride Inorganic materials 0.000 description 7
- 210000003734 kidney Anatomy 0.000 description 7
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 6
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 125000003963 dichloro group Chemical group Cl* 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- 101710134784 Agnoprotein Proteins 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 150000003057 platinum Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 201000008228 Ependymoblastoma Diseases 0.000 description 2
- 206010014968 Ependymoma malignant Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- CCQPAEQGAVNNIA-UHFFFAOYSA-N cyclobutane-1,1-dicarboxylic acid Chemical group OC(=O)C1(C(O)=O)CCC1 CCQPAEQGAVNNIA-UHFFFAOYSA-N 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 230000000527 lymphocytic effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 208000029340 primitive neuroectodermal tumor Diseases 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 229910020427 K2PtCl4 Inorganic materials 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical group OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 1
- IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical group CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 150000003891 oxalate salts Chemical group 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BQBCAHILGYZBQP-UHFFFAOYSA-N sodium;platinum(2+) Chemical compound [Na+].[Pt+2] BQBCAHILGYZBQP-UHFFFAOYSA-N 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity 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
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
-
- 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)
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8204067A NL8204067A (nl) | 1982-10-21 | 1982-10-21 | Platina-diaminecomplexen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een geneesmiddel met toepassing van een dergelijk platinadiaminecomplex voor de behandeling van kanker, alsmede aldus verkregen gevormd geneesmiddel. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH658244A5 true CH658244A5 (de) | 1986-10-31 |
Family
ID=19840444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5718/83A CH658244A5 (de) | 1982-10-21 | 1983-10-20 | Neue platinverbindungen und verfahren zu ihrer herstellung sowie verfahren zur herstellung von sie enthaltenden medizinischen zubereitungen zur behandlung von krebs. |
Country Status (28)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4786725A (en) * | 1982-06-28 | 1988-11-22 | Engelhard Corporation | Solubilized platinum (II) complexes |
| US4758588A (en) * | 1983-06-20 | 1988-07-19 | Research Corporation Technologies | Diaminocyclohexane platinum complexes |
| US4661516A (en) * | 1983-06-20 | 1987-04-28 | Research Corporation | Diaminocyclohexane platinum complexes |
| EP0169645A1 (en) * | 1984-06-27 | 1986-01-29 | Johnson Matthey Public Limited Company | Platinum co-ordination compounds |
| DE3432320A1 (de) * | 1984-09-03 | 1986-03-13 | Behringwerke Ag, 3550 Marburg | Cis-platin-komplexe mit einem pentaerythritderivat als liganden, verfahren zu ihrer herstellung und diese verbindungen enthaltendes pharmazeutisches mittel |
| HU193809B (en) * | 1984-09-12 | 1987-12-28 | Chugai Pharmaceutical Co Ltd | Process for producing new platinum complexes |
| US4737589A (en) * | 1985-08-27 | 1988-04-12 | Nippon Kayaku Kabushiki Kaisha | Platinum Complexes |
| US4760157A (en) * | 1986-01-31 | 1988-07-26 | American Cyanamid Company | (2,2,-bis(aminomethyl)-1,3-propanediol-N,N')platinum complexes |
| US4880790A (en) * | 1986-01-31 | 1989-11-14 | American Cyanamid Company | (Gem-heterocyclodimethanamine-N,N')platinum complexes |
| DE3630497A1 (de) * | 1986-09-08 | 1988-03-10 | Behringwerke Ag | Cis-platin-komplexe, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische mittel |
| ATE53217T1 (de) * | 1986-10-03 | 1990-06-15 | Asta Pharma Ag | Diamin-platin (ii)-komplexverbindungen mit einem hydroxylierten 2-phenyl-indolring. |
| JPS63203692A (ja) * | 1987-02-19 | 1988-08-23 | Nippon Kayaku Co Ltd | 新規白金錯体 |
| AT390065B (de) * | 1987-10-08 | 1990-03-12 | Behringwerke Ag | Cis-platin-komplexe, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische mittel |
| NL8802150A (nl) * | 1988-08-31 | 1990-03-16 | Tno | Platina-(ii)-diaminecomplex, werkwijze voor het bereiden van deze verbinding, preparaat met anti-tumor werking, dat deze verbinding bevat, alsmede gevormde preparaten met anti-tumor werking. |
| NL8802149A (nl) * | 1988-08-31 | 1990-03-16 | Tno | Platina-(iv)diaminecomplex, werkwijze voor het bereiden van deze verbinding, preparaat met anti-tumor werking, dat ten minste een platinaverbinding bevat, alsmede gevormde preparaten met anti-tumor werking. |
| CN102924528B (zh) * | 2012-10-29 | 2015-04-15 | 东南大学 | 抗肿瘤二价铂配合物以及该配合物和其配体的制备方法 |
Family Cites Families (6)
| 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 |
| 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 |
| NL189358C (nl) * | 1978-07-06 | 1993-03-16 | Tno | Werkwijze voor het bereiden van een geneesmiddel voor de behandeling van kanker, alsmede een van een 1,3-alkaandiamine afgeleid platina-diamminecomplex. |
| 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. |
| US4322362A (en) * | 1980-07-28 | 1982-03-30 | Bristol-Myers Company | Salts of 2-hydroxymalonate platinum complexes |
| AU538863B2 (en) * | 1980-05-27 | 1984-08-30 | Bristol-Myers Company | Platinum complex salts have anti-tumor property |
-
1982
- 1982-10-21 NL NL8204067A patent/NL8204067A/nl not_active Application Discontinuation
-
1983
- 1983-10-13 DE DE19833337333 patent/DE3337333A1/de not_active Ceased
- 1983-10-18 AU AU20275/83A patent/AU562964B2/en not_active Ceased
- 1983-10-19 IT IT23359/83A patent/IT1169858B/it active
- 1983-10-19 CA CA000439308A patent/CA1229618A/en not_active Expired
- 1983-10-20 PT PT77542A patent/PT77542B/pt unknown
- 1983-10-20 NZ NZ206018A patent/NZ206018A/en unknown
- 1983-10-20 DD DD83255826A patent/DD217522A5/de not_active IP Right Cessation
- 1983-10-20 FI FI833842A patent/FI76351C/fi not_active IP Right Cessation
- 1983-10-20 AT AT0373083A patent/AT390610B/de not_active IP Right Cessation
- 1983-10-20 YU YU2107/83A patent/YU43554B/xx unknown
- 1983-10-20 DK DK483083A patent/DK483083A/da not_active Application Discontinuation
- 1983-10-20 SE SE8305783A patent/SE8305783L/ not_active Application Discontinuation
- 1983-10-20 FR FR8316715A patent/FR2534907B1/fr not_active Expired
- 1983-10-20 IE IE2459/83A patent/IE56124B1/en not_active IP Right Cessation
- 1983-10-20 NO NO833825A patent/NO171276C/no unknown
- 1983-10-20 LU LU85054A patent/LU85054A1/xx unknown
- 1983-10-20 CH CH5718/83A patent/CH658244A5/de not_active IP Right Cessation
- 1983-10-20 GR GR72754A patent/GR79652B/el unknown
- 1983-10-20 HU HU833623A patent/HU188035B/hu not_active IP Right Cessation
- 1983-10-20 GB GB08328084A patent/GB2128615B/en not_active Expired
- 1983-10-21 BE BE0/211755A patent/BE898058A/nl not_active IP Right Cessation
- 1983-10-21 ZA ZA837857A patent/ZA837857B/xx unknown
- 1983-10-21 ES ES526670A patent/ES8406498A1/es not_active Expired
- 1983-10-21 CS CS837752A patent/CS242888B2/cs unknown
- 1983-10-21 KR KR1019830004987A patent/KR910002536B1/ko not_active Expired
- 1983-10-21 JP JP58196286A patent/JPS5993091A/ja active Granted
- 1983-10-21 PH PH29726A patent/PH24077A/en unknown
-
1992
- 1992-06-09 DK DK92755A patent/DK75592D0/da not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |