CN101279901B - 和厚朴酚系列衍生物及其制备方法和用途 - Google Patents
和厚朴酚系列衍生物及其制备方法和用途 Download PDFInfo
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- CN101279901B CN101279901B CN2008103006254A CN200810300625A CN101279901B CN 101279901 B CN101279901 B CN 101279901B CN 2008103006254 A CN2008103006254 A CN 2008103006254A CN 200810300625 A CN200810300625 A CN 200810300625A CN 101279901 B CN101279901 B CN 101279901B
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- Prior art keywords
- honokiol
- derivative
- dihydroxybiphenyl
- honokiol derivative
- diallyl
- 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.)
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- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- FVYXIJYOAGAUQK-UHFFFAOYSA-N honokiol Chemical class C1=C(CC=C)C(O)=CC=C1C1=CC(CC=C)=CC=C1O FVYXIJYOAGAUQK-UHFFFAOYSA-N 0.000 title claims description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 4
- VVOAZFWZEDHOOU-UHFFFAOYSA-N honokiol Natural products OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- BYTORXDZJWWIKR-UHFFFAOYSA-N Hinokiol Natural products CC(C)c1cc2CCC3C(C)(CO)C(O)CCC3(C)c2cc1O BYTORXDZJWWIKR-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 9
- 230000002411 adverse Effects 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 230000005526 G1 to G0 transition Effects 0.000 claims description 4
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 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 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- UJPKMTDFFUTLGM-UHFFFAOYSA-N 1-aminoethanol Chemical compound CC(N)O UJPKMTDFFUTLGM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940041181 antineoplastic drug Drugs 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 8
- 206010028980 Neoplasm Diseases 0.000 abstract description 7
- 201000011510 cancer Diseases 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 abstract description 7
- 230000000259 anti-tumor effect Effects 0.000 abstract description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 4
- -1 hydroxide alkyl Chemical group 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 abstract 1
- 239000002574 poison Substances 0.000 abstract 1
- 231100000614 poison Toxicity 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 20
- 150000003141 primary amines Chemical class 0.000 description 18
- 239000012153 distilled water Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 239000012071 phase Substances 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000012065 filter cake Substances 0.000 description 7
- 238000000643 oven drying Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- 238000004062 sedimentation Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 0 *Cc1cc(CC=C)cc(-c2cc(CC=C)ccc2O)c1O Chemical compound *Cc1cc(CC=C)cc(-c2cc(CC=C)ccc2O)c1O 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 description 2
- 150000005829 chemical entities Chemical class 0.000 description 2
- 231100000599 cytotoxic agent Toxicity 0.000 description 2
- 239000002619 cytotoxin Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000508 neurotrophic effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000003142 primary aromatic amines Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000005728 strengthening Methods 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- IBKNHHZQPPUDQJ-UHFFFAOYSA-N 2-(4-hydroxy-3-prop-2-enylphenyl)-4-propylphenol Chemical compound CCCC1=CC=C(O)C(C=2C=C(CC=C)C(O)=CC=2)=C1 IBKNHHZQPPUDQJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 101710112752 Cytotoxin Proteins 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241000218378 Magnolia Species 0.000 description 1
- 241001673966 Magnolia officinalis Species 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 210000002821 alveolar epithelial cell Anatomy 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HZQXXYJHLCSUGQ-UHFFFAOYSA-N ethyl acetate hexane methanol hydrate Chemical compound O.OC.CCCCCC.CCOC(C)=O HZQXXYJHLCSUGQ-UHFFFAOYSA-N 0.000 description 1
- 229940094952 green tea extract Drugs 0.000 description 1
- 235000020688 green tea extract Nutrition 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229940065287 selenium compound Drugs 0.000 description 1
- 150000003343 selenium compounds Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
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CN2008103006254A CN101279901B (zh) | 2007-12-25 | 2008-03-19 | 和厚朴酚系列衍生物及其制备方法和用途 |
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CN200710050966 | 2007-12-25 | ||
CN200710050966.6 | 2007-12-25 | ||
CN2008103006254A CN101279901B (zh) | 2007-12-25 | 2008-03-19 | 和厚朴酚系列衍生物及其制备方法和用途 |
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CN200910312570A Division CN101774896A (zh) | 2007-12-25 | 2008-03-19 | 和厚朴酚系列衍生物及其制备方法和用途 |
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CN101279901A CN101279901A (zh) | 2008-10-08 |
CN101279901B true CN101279901B (zh) | 2011-08-17 |
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Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102898284B (zh) * | 2011-07-25 | 2015-08-26 | 成都金瑞基业生物科技有限公司 | 3-烯丙基-[1,1′-联苯]-4-酚及其衍生物以及它们的制备方法和用途 |
CN103965032B (zh) * | 2014-04-02 | 2015-06-03 | 浙江大学 | 联苯新木脂素化合物及其提取方法和用途 |
JP6217999B2 (ja) * | 2014-10-09 | 2017-10-25 | Dic株式会社 | 重合性化合物及び光学異方体 |
KR102614432B1 (ko) | 2015-12-08 | 2023-12-15 | 디아이씨 가부시끼가이샤 | 중합성 화합물 및 광학 이방체 |
WO2019121440A1 (en) * | 2017-12-22 | 2019-06-27 | Unilever N.V. | An antimicrobial composition |
CN110950773B (zh) * | 2018-09-27 | 2021-05-25 | 湖南大学 | 联苯二酚酰胺衍生物及其作为抗癌药物的应用 |
CN110845350B (zh) * | 2019-09-20 | 2021-11-19 | 广东省禾基生物科技有限公司 | 和厚朴酚衍生物及其制备方法与应用 |
CN110615742B (zh) * | 2019-09-20 | 2021-11-19 | 广东省禾基生物科技有限公司 | 厚朴酚衍生物及其制备方法与应用 |
CN112933302B (zh) * | 2021-02-02 | 2022-06-03 | 四川大学华西医院 | 基于中药厚朴的多功能生物医用涂层材料及其制备方法 |
CN115215771B (zh) * | 2022-08-06 | 2024-04-02 | 蚌埠医学院 | 和厚朴酚衍生物及制备方法和在制备抗肿瘤药物中的应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999000346A1 (en) * | 1997-06-26 | 1999-01-07 | Board Of Regents, The University Of Texas System | Synthesis of dihydrohonokiol compositions |
CN1692901A (zh) * | 2004-05-08 | 2005-11-09 | 陈菲 | 和厚朴酚在制备抗肿瘤或预防肿瘤的药物组合物中的应用 |
WO2006107451A2 (en) * | 2005-02-23 | 2006-10-12 | Univ Emory | Honokiol derivatives for the treatment of proliferative disorders |
-
2008
- 2008-03-19 CN CN2008103006254A patent/CN101279901B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999000346A1 (en) * | 1997-06-26 | 1999-01-07 | Board Of Regents, The University Of Texas System | Synthesis of dihydrohonokiol compositions |
CN1692901A (zh) * | 2004-05-08 | 2005-11-09 | 陈菲 | 和厚朴酚在制备抗肿瘤或预防肿瘤的药物组合物中的应用 |
WO2006107451A2 (en) * | 2005-02-23 | 2006-10-12 | Univ Emory | Honokiol derivatives for the treatment of proliferative disorders |
Non-Patent Citations (2)
Title |
---|
左克强等.和厚朴酚及其抗肿瘤作用.岳阳职业技术学院学报22 5.2007,22(5),第81-84页. |
左克强等.和厚朴酚及其抗肿瘤作用.岳阳职业技术学院学报22 5.2007,22(5),第81-84页. * |
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Application publication date: 20081008 Assignee: Sichuan jinruijiye Pharmaceutical Research Co.,Ltd. Assignor: Chengdu Jinrui Jiye Bio-Technology Co.,Ltd. Contract record no.: X2022510000016 Denomination of invention: Magnolol series derivatives and their preparation method and Application Granted publication date: 20110817 License type: Common License Record date: 20220421 |
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