CN103601759A - 一种用于治疗肿瘤的钌(iii)络合物的制备方法 - Google Patents
一种用于治疗肿瘤的钌(iii)络合物的制备方法 Download PDFInfo
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- CN103601759A CN103601759A CN201310490377.5A CN201310490377A CN103601759A CN 103601759 A CN103601759 A CN 103601759A CN 201310490377 A CN201310490377 A CN 201310490377A CN 103601759 A CN103601759 A CN 103601759A
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- Prior art keywords
- indazole
- ruthenium
- iii
- tetrachloro
- trans
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- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- BPEVHDGLPIIAGH-UHFFFAOYSA-N ruthenium(3+) Chemical compound [Ru+3] BPEVHDGLPIIAGH-UHFFFAOYSA-N 0.000 title claims abstract description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 26
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 229960001701 chloroform Drugs 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 12
- WLCLBOVXRZPLIW-UHFFFAOYSA-N hydron;1h-indazole;chloride Chemical compound Cl.C1=CC=C2C=NNC2=C1 WLCLBOVXRZPLIW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012043 crude product Substances 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 3
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 5
- 238000007670 refining Methods 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract description 16
- 229910052707 ruthenium Inorganic materials 0.000 abstract description 16
- 239000000047 product Substances 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 4
- 239000011780 sodium chloride Substances 0.000 abstract 2
- 238000013341 scale-up Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 12
- 239000003814 drug Substances 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 238000010189 synthetic method Methods 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- 238000005342 ion exchange Methods 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000001093 anti-cancer Effects 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- 229960004562 carboplatin Drugs 0.000 description 3
- 190000008236 carboplatin Chemical compound 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000011275 oncology therapy Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CUXQLKLUPGTTKL-UHFFFAOYSA-M microcosmic salt Chemical compound [NH4+].[Na+].OP([O-])([O-])=O CUXQLKLUPGTTKL-UHFFFAOYSA-M 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
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CN201310490377.5A CN103601759B (zh) | 2013-10-18 | 2013-10-18 | 一种用于治疗肿瘤的钌(iii)络合物的制备方法 |
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CN201310490377.5A CN103601759B (zh) | 2013-10-18 | 2013-10-18 | 一种用于治疗肿瘤的钌(iii)络合物的制备方法 |
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CN103601759A true CN103601759A (zh) | 2014-02-26 |
CN103601759B CN103601759B (zh) | 2015-08-19 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108752391A (zh) * | 2018-08-22 | 2018-11-06 | 广西师范学院 | 治疗胃癌的芳基钌配合物及其制备方法和用途 |
CN108752389A (zh) * | 2018-08-22 | 2018-11-06 | 广西师范学院 | 治疗高血压的芳基钌配合物及其制备方法和用途 |
JP2020518676A (ja) * | 2017-05-05 | 2020-06-25 | インテザイン テクノロジーズ, インコーポレイテッド | トランス−[テトラクロロビス(1h−インダゾール)ルテニウム酸(iii)]及びその組成物の製造 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101677572A (zh) * | 2007-06-11 | 2010-03-24 | 尼基制药公司 | 制备钌络合物的方法 |
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2013
- 2013-10-18 CN CN201310490377.5A patent/CN103601759B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101677572A (zh) * | 2007-06-11 | 2010-03-24 | 尼基制药公司 | 制备钌络合物的方法 |
Non-Patent Citations (1)
Title |
---|
WOLFGANG PETI ET AL.: "Synthesis of Tumor-Inhibiting Complex Salts Containing the Anion trans-Tetrachlorobis(indazole)ruthenate(III) and Crystal Structure of the Tetraphenylphosphonium Salt", 《EUR. J. INORG. CHEM.》, no. 9, 12 August 1999 (1999-08-12) * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2020518676A (ja) * | 2017-05-05 | 2020-06-25 | インテザイン テクノロジーズ, インコーポレイテッド | トランス−[テトラクロロビス(1h−インダゾール)ルテニウム酸(iii)]及びその組成物の製造 |
CN111372939A (zh) * | 2017-05-05 | 2020-07-03 | 博德疗法公司 | 反式-[四氯双(1h-吲唑)钌(iii)]及其组合物的制备 |
JP7183253B2 (ja) | 2017-05-05 | 2022-12-05 | インテザイン テクノロジーズ, インコーポレイテッド | トランス-[テトラクロロビス(1h-インダゾール)ルテニウム酸(iii)]及びその組成物の製造 |
US11739111B2 (en) | 2017-05-05 | 2023-08-29 | Bold Therapeutics, Inc. | Manufacture of trans-[tetrachlorobis(1H-indazole)ruthenate (III)] and compositions thereof |
CN111372939B (zh) * | 2017-05-05 | 2023-11-07 | 博德疗法公司 | 反式-[四氯双(1h-吲唑)钌(iii)]及其组合物的制备 |
JP7433402B2 (ja) | 2017-05-05 | 2024-02-19 | インテザイン テクノロジーズ, インコーポレイテッド | トランス-[テトラクロロビス(1h-インダゾール)ルテニウム酸(iii)]及びその組成物の製造 |
CN108752391A (zh) * | 2018-08-22 | 2018-11-06 | 广西师范学院 | 治疗胃癌的芳基钌配合物及其制备方法和用途 |
CN108752389A (zh) * | 2018-08-22 | 2018-11-06 | 广西师范学院 | 治疗高血压的芳基钌配合物及其制备方法和用途 |
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Inventor after: Xie Lili Inventor before: Qin Huali Inventor before: Xiong Feng Inventor before: Zhang Zhi |
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Effective date of registration: 20170927 Address after: 277500, Zaozhuang, Shandong province Tengzhou City 154 Patentee after: Xie Lili Address before: 430075 A7 Exhibition Center, 858, hi tech Avenue, East Lake Development Zone, Wuhan, Hubei, China Patentee before: WUHAN LIBAORUI MEDICINE SCIENCE & TECHNOLOGY CO.,LTD. |
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Effective date of registration: 20180511 Address after: 225300 room 104, Pearl Road, Yongan Town, Yongan, Taizhou, Jiangsu Patentee after: Du Lihong Address before: 102600 3 floor, 2 building, No. 4 Daxing District Garden Road, Beijing, 1 unit 317 Patentee before: BEIJING ZHITOUJIA INTELLECTUAL PROPERTY OPERATION CO.,LTD. Effective date of registration: 20180511 Address after: 102600 3 floor, 2 building, No. 4 Daxing District Garden Road, Beijing, 1 unit 317 Patentee after: BEIJING ZHITOUJIA INTELLECTUAL PROPERTY OPERATION CO.,LTD. Address before: 277500 No. 154, Buzhang village, Chaihu Town, Tengzhou, Zaozhuang, Shandong Patentee before: Xie Lili |
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