DE2845372C2 - - Google Patents
Info
- Publication number
- DE2845372C2 DE2845372C2 DE2845372A DE2845372A DE2845372C2 DE 2845372 C2 DE2845372 C2 DE 2845372C2 DE 2845372 A DE2845372 A DE 2845372A DE 2845372 A DE2845372 A DE 2845372A DE 2845372 C2 DE2845372 C2 DE 2845372C2
- Authority
- DE
- Germany
- Prior art keywords
- water
- solution
- complex
- platinum
- stirred
- 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 46
- 229910052697 platinum Inorganic materials 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- VAAHIEKGRCIMPM-UHFFFAOYSA-N platinum;propan-2-amine Chemical compound [Pt].CC(C)N.CC(C)N VAAHIEKGRCIMPM-UHFFFAOYSA-N 0.000 description 15
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000011148 porous material Substances 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000009102 absorption Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 2
- 229940089960 chloroacetate Drugs 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 2
- KPFSGNRRZMYZPH-UHFFFAOYSA-M potassium;2-chloroacetate Chemical compound [K+].[O-]C(=O)CCl KPFSGNRRZMYZPH-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- -1 bis (isobutylamine) platinum Chemical compound 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- DOYLBWHHKGKDBV-UHFFFAOYSA-N platinum(2+);propan-2-amine Chemical compound [Pt+2].CC(C)N DOYLBWHHKGKDBV-UHFFFAOYSA-N 0.000 description 1
- AJWDBMRAQLRSCK-UHFFFAOYSA-N platinum;propan-2-amine Chemical compound [Pt].CC(C)N AJWDBMRAQLRSCK-UHFFFAOYSA-N 0.000 description 1
- IZLFUDHPNDYYHS-UHFFFAOYSA-M potassium;2-bromoacetate Chemical compound [K+].[O-]C(=O)CBr IZLFUDHPNDYYHS-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 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)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4349277 | 1977-10-19 | ||
| GB2046178 | 1978-05-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2845372A1 DE2845372A1 (de) | 1979-04-26 |
| DE2845372C2 true DE2845372C2 (pt-PT) | 1990-12-13 |
Family
ID=26254690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782845372 Granted DE2845372A1 (de) | 1977-10-19 | 1978-10-18 | Platin-komplex-verbindung, verfahren zu ihrer herstellung und anwendung der verbindung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4230631A (pt-PT) |
| JP (1) | JPS5470226A (pt-PT) |
| CA (1) | CA1117543A (pt-PT) |
| DE (1) | DE2845372A1 (pt-PT) |
| FR (1) | FR2406441A1 (pt-PT) |
| NL (1) | NL7810434A (pt-PT) |
| SE (1) | SE447385B (pt-PT) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4500465A (en) * | 1982-06-28 | 1985-02-19 | Engelhard Corporation | Solubilized platinum (II) complexes |
| JPS59112995A (ja) * | 1982-12-21 | 1984-06-29 | Shionogi & Co Ltd | 新規グリコ−ル酸白金錯体 |
| IL67789A (en) * | 1983-01-31 | 1986-09-30 | Yissum Res Dev Co | Amino-substituted malonato platinum(ii)complexes and method for their preparation |
| US4533502A (en) * | 1983-02-22 | 1985-08-06 | Rochon Fernande D | Platinum (II) compounds and their preparation |
| IL71804A (en) * | 1983-05-10 | 1989-06-30 | Andrulis Res Corp | Bis-(platinum diamine)complexes and antitumor pharmaceutical compositions containing the same |
| US4565884A (en) * | 1983-05-10 | 1986-01-21 | Andrulis Research Corporation | Bis-platinum complexes as antitumor agents |
| US4720504A (en) * | 1983-05-10 | 1988-01-19 | Andrulis Research Corporation | Use of bis-platinum complexes as antitumor agents |
| JPS59222498A (ja) * | 1983-06-01 | 1984-12-14 | Shionogi & Co Ltd | 新規グリコ−ル酸系白金錯体および抗悪性腫瘍剤 |
| JPS6034982A (ja) * | 1983-08-05 | 1985-02-22 | Yoshinori Kitani | １，２−ジアミノシクロヘキサン白金（２）錯体 |
| GB8416048D0 (en) * | 1984-06-22 | 1984-07-25 | Johnson Matthey Plc | Anti-tumour compounds of platinum |
| JPS6296A (ja) * | 1985-03-06 | 1987-01-06 | Sumitomo Pharmaceut Co Ltd | 脂溶性白金（２）錯体 |
| US4866092A (en) * | 1985-06-26 | 1989-09-12 | American Cyanamid Company | Platinum complexes of amines with novel dibasic acids |
| US4675336A (en) * | 1985-06-26 | 1987-06-23 | American Cyanamid Company | Platinum complexes of amines with dibasic acids |
| US5384127A (en) * | 1985-10-18 | 1995-01-24 | Board Of Regents, The University Of Texas System | Stable liposomal formulations of lipophilic platinum compounds |
| US5041581A (en) * | 1985-10-18 | 1991-08-20 | The University Of Texas System Board Of Regents | Hydrophobic cis-platinum complexes efficiently incorporated into liposomes |
| JPS63501568A (ja) * | 1985-10-18 | 1988-06-16 | ボ−ド・オブ・リ−ジェンツ、ザ・ユニバ−シティ−・オブ・テキサス・システム | リポソ−ムに有効に組み込まれた疎水性シス−プラチナ複合体 |
| US5041578A (en) * | 1988-11-22 | 1991-08-20 | Board Of Regents, The University Of Texas System | Water soluble 1,2-diaminocyclohexane platinum (IV) complexes as antitumor agents |
| US5393909A (en) * | 1988-11-22 | 1995-02-28 | Board Of Regents, The University Of Texas System | Diamine platinum complexes as antitumor agents |
| US5434256A (en) * | 1988-11-22 | 1995-07-18 | Board Of Regents, The University Of Texas System | Diamine platinum complexes as antitumor agents |
| US5038952A (en) * | 1989-12-14 | 1991-08-13 | Coors Brewing Company | Closure assembly for pressurized plastic beverage container |
| US5843475A (en) * | 1996-12-06 | 1998-12-01 | Board Of Regents, The University Of Texas System | Delivery and activation through liposome incorporation of diaminocyclohexane platinum (II) complexes |
| CN102286050A (zh) * | 2011-06-24 | 2011-12-21 | 天津大学 | 用于肿瘤靶向治疗的含葡萄糖铂配合物及其制备方法 |
| CN102276674A (zh) * | 2011-06-24 | 2011-12-14 | 天津大学 | 用于肿瘤靶向治疗的含半乳糖铂配合物及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1432562A (en) * | 1972-04-10 | 1976-04-22 | Rustenburg Platinum Mines Ltd | Platinum co-ordination compounds |
| GB1432563A (en) * | 1972-04-10 | 1976-04-22 | Rustenburg Platinum Mines Ltd | Platinum- co-ordination compounds |
| CH605550A5 (pt-PT) * | 1972-06-08 | 1978-09-29 | Research Corp | |
| US4115418A (en) * | 1976-09-02 | 1978-09-19 | Government Of The United States Of America | 1,2-diaminocyclohexane platinum (ii) complexes having antineoplastic activity |
-
1978
- 1978-10-17 SE SE7810800A patent/SE447385B/sv not_active IP Right Cessation
- 1978-10-17 US US05/952,213 patent/US4230631A/en not_active Expired - Lifetime
- 1978-10-18 NL NL7810434A patent/NL7810434A/xx not_active Application Discontinuation
- 1978-10-18 DE DE19782845372 patent/DE2845372A1/de active Granted
- 1978-10-19 CA CA000313742A patent/CA1117543A/en not_active Expired
- 1978-10-19 FR FR7830418A patent/FR2406441A1/fr active Granted
- 1978-10-19 JP JP12790678A patent/JPS5470226A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS629115B2 (pt-PT) | 1987-02-26 |
| FR2406441B1 (pt-PT) | 1982-12-31 |
| CA1117543A (en) | 1982-02-02 |
| FR2406441A1 (fr) | 1979-05-18 |
| US4230631A (en) | 1980-10-28 |
| NL7810434A (nl) | 1979-04-23 |
| DE2845372A1 (de) | 1979-04-26 |
| SE7810800L (sv) | 1979-04-20 |
| JPS5470226A (en) | 1979-06-05 |
| SE447385B (sv) | 1986-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: JOHNSON MATTHEY PLC, LONDON, GB |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |