CN112533935A - 一种铂类化合物磷酸盐及其制备方法 - Google Patents
一种铂类化合物磷酸盐及其制备方法 Download PDFInfo
- Publication number
- CN112533935A CN112533935A CN201980051809.8A CN201980051809A CN112533935A CN 112533935 A CN112533935 A CN 112533935A CN 201980051809 A CN201980051809 A CN 201980051809A CN 112533935 A CN112533935 A CN 112533935A
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- Prior art keywords
- compound
- cyclohexanediamine
- diethylamino
- platinum
- solvent
- Prior art date
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- Granted
Links
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- 238000002360 preparation method Methods 0.000 title abstract description 24
- 229910019142 PO4 Inorganic materials 0.000 title description 20
- 239000010452 phosphate Substances 0.000 title description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 49
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- 238000006243 chemical reaction Methods 0.000 claims description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
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- 238000000634 powder X-ray diffraction Methods 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- AEAVNKNQJBFMCW-SKSSAGQDSA-L (1r,2r)-cyclohexane-1,2-diamine;diiodoplatinum Chemical compound I[Pt]I.N[C@@H]1CCCC[C@H]1N AEAVNKNQJBFMCW-SKSSAGQDSA-L 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
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- FWZZTLRIXBYOKR-SKSSAGQDSA-N (1R,2R)-cyclohexane-1,2-diamine platinum(2+) dihydrate Chemical compound O.O.[Pt++].N[C@@H]1CCCC[C@H]1N FWZZTLRIXBYOKR-SKSSAGQDSA-N 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 239000012467 final product Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 230000000259 anti-tumor effect Effects 0.000 abstract description 3
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- 239000000047 product Substances 0.000 description 15
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
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- XAWJCWNXIIZHLM-UHFFFAOYSA-N diethyl 2-(4-bromobutyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)CCCCBr XAWJCWNXIIZHLM-UHFFFAOYSA-N 0.000 description 3
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- 239000000126 substance Substances 0.000 description 3
- GENQRBLPJNTJBE-RQDPQJJXSA-N (1R,2R)-cyclohexane-1,2-diamine platinum(2+) dinitrate dihydrate Chemical compound O.O.[Pt+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O.N[C@@H]1CCCC[C@H]1N GENQRBLPJNTJBE-RQDPQJJXSA-N 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
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- 239000000969 carrier Substances 0.000 description 2
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- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
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- LEAHFJQFYSDGGP-UHFFFAOYSA-K trisodium;dihydrogen phosphate;hydrogen phosphate Chemical compound [Na+].[Na+].[Na+].OP(O)([O-])=O.OP([O-])([O-])=O LEAHFJQFYSDGGP-UHFFFAOYSA-K 0.000 description 2
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 1
- MCRZWYDXIGCFKO-UHFFFAOYSA-N 2-butylpropanedioic acid Chemical compound CCCCC(C(O)=O)C(O)=O MCRZWYDXIGCFKO-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- 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
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- 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
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Abstract
提供2‑(4‑二乙胺基)丁基丙二酸‑(1R,2R)‑(‑)‑1,2‑环己二胺合铂(II)磷酸盐，其溶解度高、吸湿性较低、稳定性好，适用于制备成各种抗肿瘤药物制剂。还提供无定型的2‑(4‑二乙胺基)丁基丙二酸‑(1R,2R)‑(‑)‑1,2‑环己二胺合铂(II)磷酸盐的制备方法，其操作简单，便于产业化实现。
Description
PCT国内申请，说明书已公开。
Claims (9)
- PCT国内申请，权利要求书已公开。
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811017816X | 2018-09-01 | ||
| CN201811017816 | 2018-09-01 | ||
| PCT/CN2019/103147 WO2020043144A1 (zh) | 2018-09-01 | 2019-08-28 | 一种铂类化合物磷酸盐及其制备方法 |
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| CN112533935A true CN112533935A (zh) | 2021-03-19 |
| CN112533935B CN112533935B (zh) | 2023-01-13 |
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| US (1) | US11661434B2 (zh) |
| EP (1) | EP3845544B1 (zh) |
| JP (1) | JP7180923B2 (zh) |
| KR (1) | KR102645496B1 (zh) |
| CN (1) | CN112533935B (zh) |
| AU (1) | AU2019326814B2 (zh) |
| CA (1) | CA3110611A1 (zh) |
| WO (1) | WO2020043144A1 (zh) |
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| DE102004005906B3 (de) | 2004-02-05 | 2005-09-29 | W.C. Heraeus Gmbh | Verfahren zur Herstellung von 1,2-Diaminocylohexan-Platin(II)-Komplexen |
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- 2019-08-28 WO PCT/CN2019/103147 patent/WO2020043144A1/zh active Application Filing
- 2019-08-28 JP JP2021511557A patent/JP7180923B2/ja active Active
- 2019-08-28 US US17/271,110 patent/US11661434B2/en active Active
- 2019-08-28 CA CA3110611A patent/CA3110611A1/en active Pending
- 2019-08-28 CN CN201980051809.8A patent/CN112533935B/zh active Active
- 2019-08-28 EP EP19854967.7A patent/EP3845544B1/en active Active
- 2019-08-28 AU AU2019326814A patent/AU2019326814B2/en active Active
- 2019-08-28 KR KR1020217007597A patent/KR102645496B1/ko active IP Right Grant
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| EP3845544B1 (en) | 2023-11-15 |
| EP3845544A4 (en) | 2021-07-07 |
| JP2021535166A (ja) | 2021-12-16 |
| EP3845544C0 (en) | 2023-11-15 |
| US20210253619A1 (en) | 2021-08-19 |
| KR102645496B1 (ko) | 2024-03-07 |
| CA3110611A1 (en) | 2020-03-05 |
| US11661434B2 (en) | 2023-05-30 |
| EP3845544A1 (en) | 2021-07-07 |
| CN112533935B (zh) | 2023-01-13 |
| KR20210044832A (ko) | 2021-04-23 |
| WO2020043144A1 (zh) | 2020-03-05 |
| AU2019326814B2 (en) | 2021-12-02 |
| JP7180923B2 (ja) | 2022-11-30 |
| AU2019326814A1 (en) | 2021-04-08 |
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