CN104262409A - 一种用于治疗肝癌的有机化合物及其制备方法和用途 - Google Patents
一种用于治疗肝癌的有机化合物及其制备方法和用途 Download PDFInfo
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- CN104262409A CN104262409A CN201410513109.5A CN201410513109A CN104262409A CN 104262409 A CN104262409 A CN 104262409A CN 201410513109 A CN201410513109 A CN 201410513109A CN 104262409 A CN104262409 A CN 104262409A
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- CN
- China
- Prior art keywords
- organic compound
- treatment
- liver cancer
- weight parts
- thiophene
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Links
- 208000014018 liver neoplasm Diseases 0.000 title claims abstract description 32
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 201000007270 liver cancer Diseases 0.000 claims abstract description 29
- 239000000126 substance Substances 0.000 claims abstract description 13
- 208000005718 Stomach Neoplasms Diseases 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 21
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 claims description 21
- YKFLAYDHMOASIY-UHFFFAOYSA-N γ-terpinene Chemical compound CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 claims description 18
- 229910052707 ruthenium Inorganic materials 0.000 claims description 16
- 238000001556 precipitation Methods 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 14
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 14
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 claims description 11
- 239000012467 final product Substances 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 201000000498 stomach carcinoma Diseases 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 abstract description 5
- 239000002775 capsule Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000000839 emulsion Substances 0.000 abstract description 2
- 238000002347 injection Methods 0.000 abstract description 2
- 239000007924 injection Substances 0.000 abstract description 2
- 239000006187 pill Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000000375 suspending agent Substances 0.000 abstract description 2
- 239000003826 tablet Substances 0.000 abstract description 2
- 206010017758 gastric cancer Diseases 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 201000011549 stomach cancer Diseases 0.000 abstract 1
- -1 aryl ruthenium Chemical compound 0.000 description 10
- OXACXUIQRLDCKR-UHFFFAOYSA-N CC1=CC=C(C=C1)C(C)C.C1(=CC=CC=C1)NC(NN)=S Chemical compound CC1=CC=C(C=C1)C(C)C.C1(=CC=CC=C1)NC(NN)=S OXACXUIQRLDCKR-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 7
- HFPZCAJZSCWRBC-UHFFFAOYSA-N CC(C)c1ccc(C)cc1 Chemical compound CC(C)c1ccc(C)cc1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000002223 garnet Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 0 PNC(*N=Cc1ccc[s]1)=S Chemical compound PNC(*N=Cc1ccc[s]1)=S 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
- 238000002474 experimental method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KKIGUVBJOHCXSP-UHFFFAOYSA-N 4-phenylthiosemicarbazide Chemical compound NNC(=S)NC1=CC=CC=C1 KKIGUVBJOHCXSP-UHFFFAOYSA-N 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- YAYRGNWWLMLWJE-UHFFFAOYSA-L carboplatin Chemical compound O=C1O[Pt](N)(N)OC(=O)C11CCC1 YAYRGNWWLMLWJE-UHFFFAOYSA-L 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 1
- 229960001756 oxaliplatin Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001225 therapeutic effect 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
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
细胞株 | SGC-7901 | BEL-7404 |
IC50(umol/mL) | 16.5±5.8 | 36.2±5.9 |
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410513109.5A CN104262409B (zh) | 2014-09-29 | 2014-09-29 | 一种用于治疗肝癌的有机化合物及其制备方法和用途 |
Applications Claiming Priority (1)
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---|---|---|---|
CN201410513109.5A CN104262409B (zh) | 2014-09-29 | 2014-09-29 | 一种用于治疗肝癌的有机化合物及其制备方法和用途 |
Publications (2)
Publication Number | Publication Date |
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CN104262409A true CN104262409A (zh) | 2015-01-07 |
CN104262409B CN104262409B (zh) | 2017-02-01 |
Family
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Family Applications (1)
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CN201410513109.5A Active CN104262409B (zh) | 2014-09-29 | 2014-09-29 | 一种用于治疗肝癌的有机化合物及其制备方法和用途 |
Country Status (1)
Country | Link |
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CN (1) | CN104262409B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105239068A (zh) * | 2015-11-17 | 2016-01-13 | 广西中医药大学 | 钌配合物修饰的不锈钢材料及其制备方法与用途 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060009445A1 (en) * | 2002-12-23 | 2006-01-12 | Faustus Forschungs Cie. Translational Cancer Research Gmbh | Tumor-inhibiting anellated azepinone derivatives |
CN102503987A (zh) * | 2011-11-21 | 2012-06-20 | 广西师范学院 | 一种具有抗肿瘤活性的配合物及其制备方法和用途 |
CN103288881A (zh) * | 2013-07-02 | 2013-09-11 | 广西师范学院 | 一种具有抗肿瘤活性的双核金属钌配合物 |
-
2014
- 2014-09-29 CN CN201410513109.5A patent/CN104262409B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060009445A1 (en) * | 2002-12-23 | 2006-01-12 | Faustus Forschungs Cie. Translational Cancer Research Gmbh | Tumor-inhibiting anellated azepinone derivatives |
CN102503987A (zh) * | 2011-11-21 | 2012-06-20 | 广西师范学院 | 一种具有抗肿瘤活性的配合物及其制备方法和用途 |
CN103288881A (zh) * | 2013-07-02 | 2013-09-11 | 广西师范学院 | 一种具有抗肿瘤活性的双核金属钌配合物 |
Non-Patent Citations (2)
Title |
---|
WEI SU等,: "Synthesis, crystal and electronic structure, anticancer activity of ruthenium(II) arene complexes with thiosemicarbazones", 《APPL. ORGANOMETAL. CHEM.》 * |
周泉等,: "2-甲酰噻吩缩氨基硫脲及其芳基钌配合物的合成、结构与抗癌活性研究", 《有机化学》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105239068A (zh) * | 2015-11-17 | 2016-01-13 | 广西中医药大学 | 钌配合物修饰的不锈钢材料及其制备方法与用途 |
CN105239068B (zh) * | 2015-11-17 | 2017-11-03 | 广西中医药大学 | 钌配合物修饰的不锈钢材料及其制备方法与用途 |
Also Published As
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CN104262409B (zh) | 2017-02-01 |
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Effective date of registration: 20210121 Address after: 710000 Shaanxi Xi'an economic and Technological Development Zone, Fengcheng four road, Ming Guang road, southeast corner of the new business building 1808 Patentee after: SHAANXI ZHUANYI INTELLECTUAL PROPERTY OPERATION Co.,Ltd. Address before: 530213 No. 13 Wuhe Avenue, Qingxiu District, Nanning City, Guangxi Zhuang Autonomous Region Patentee before: Guangxi University of Chinese Medicine |
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Effective date of registration: 20220401 Address after: 016100 No. 069, Albas sumuhu and tolgaigacha, otok banner, Ordos City, Inner Mongolia Autonomous Region Patentee after: Anan Yutaka Address before: 710000 Shaanxi Xi'an economic and Technological Development Zone, Fengcheng four road, Ming Guang road, southeast corner of the new business building 1808 Patentee before: SHAANXI ZHUANYI INTELLECTUAL PROPERTY OPERATION CO.,LTD. |