CN104803966A - 反式-2-19烷基-4-羟甲基-1,3-二氧戊环化合物及其制备方法 - Google Patents
反式-2-19烷基-4-羟甲基-1,3-二氧戊环化合物及其制备方法 Download PDFInfo
- Publication number
- CN104803966A CN104803966A CN201410099171.4A CN201410099171A CN104803966A CN 104803966 A CN104803966 A CN 104803966A CN 201410099171 A CN201410099171 A CN 201410099171A CN 104803966 A CN104803966 A CN 104803966A
- Authority
- CN
- China
- Prior art keywords
- compound
- formula
- preparation
- liver
- hydroxymethyl
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 15
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 claims description 12
- 208000019423 liver disease Diseases 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 5
- 238000006359 acetalization reaction Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- JWIPGAFCGUDKEY-UHFFFAOYSA-L O[Cr](Cl)(=O)=O.C1=CC=NC=C1 Chemical compound O[Cr](Cl)(=O)=O.C1=CC=NC=C1 JWIPGAFCGUDKEY-UHFFFAOYSA-L 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000004480 active ingredient Substances 0.000 description 18
- 235000020639 clam Nutrition 0.000 description 13
- 230000000694 effects Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000003814 drug Substances 0.000 description 8
- 210000004185 liver Anatomy 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000013372 meat Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 241000237519 Bivalvia Species 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 241000411851 herbal medicine Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 210000005229 liver cell Anatomy 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- WTPPRJKFRFIQKT-UHFFFAOYSA-N 1,6-dimethyl-8,9-dihydronaphtho[1,2-g][1]benzofuran-10,11-dione;1-methyl-6-methylidene-8,9-dihydro-7h-naphtho[1,2-g][1]benzofuran-10,11-dione Chemical compound O=C1C(=O)C2=C3CCCC(=C)C3=CC=C2C2=C1C(C)=CO2.O=C1C(=O)C2=C3CCC=C(C)C3=CC=C2C2=C1C(C)=CO2 WTPPRJKFRFIQKT-UHFFFAOYSA-N 0.000 description 1
- 241000202726 Bupleurum Species 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 208000004930 Fatty Liver Diseases 0.000 description 1
- 206010019708 Hepatic steatosis Diseases 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 235000003143 Panax notoginseng Nutrition 0.000 description 1
- 241000180649 Panax notoginseng Species 0.000 description 1
- 241000270666 Testudines Species 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical group [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- HPXRASQACBNMFL-DHIUTWEWSA-N [(2R,4R)-2-nonadecyl-1,3-dioxolan-4-yl]methanol Chemical compound C(CCCCCCCCCCCCCCCCCC)[C@@H]1OC[C@H](O1)CO HPXRASQACBNMFL-DHIUTWEWSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 229960001338 colchicine Drugs 0.000 description 1
- 238000010835 comparative analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- WHFKIZXBVFEJGA-UHFFFAOYSA-L dihydroxy(dioxo)chromium;pyridine Chemical compound O[Cr](O)(=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 WHFKIZXBVFEJGA-UHFFFAOYSA-L 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 238000005184 irreversible process Methods 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 244000132619 red sage Species 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/20—Free hydroxyl or mercaptan
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW103102539A TWI553000B (zh) | 2014-01-23 | 2014-01-23 | 反式－２－１９烷基－４－羥甲基－１，３－二氧戊環化合物及其製備方法 |
| TW103102539 | 2014-01-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104803966A true CN104803966A (zh) | 2015-07-29 |
Family
ID=53544198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410099171.4A Pending CN104803966A (zh) | 2014-01-23 | 2014-03-17 | 反式-2-19烷基-4-羟甲基-1,3-二氧戊环化合物及其制备方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20150203466A1 (https=) |
| JP (2) | JP2015137277A (https=) |
| KR (1) | KR101644450B1 (https=) |
| CN (1) | CN104803966A (https=) |
| MY (1) | MY182857A (https=) |
| TW (1) | TWI553000B (https=) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100099894A1 (en) * | 2006-10-09 | 2010-04-22 | Jean-Luc Dubois | Method for the Synthesis of Cyclic Acetals by the Reactive Extraction of a Polyol in a Concentrated Solution |
| TW201114465A (en) * | 2009-10-19 | 2011-05-01 | Univ Nat Kaohsiung Marine | Purification process and substance for clam |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2950894B1 (fr) * | 2009-10-06 | 2011-12-23 | Arkema France | Utilisation d'acetals de glycerol comme agents de coalescence pour laques, peintures ou vernis et compositions les comprenant |
-
2014
- 2014-01-23 TW TW103102539A patent/TWI553000B/zh active
- 2014-03-17 CN CN201410099171.4A patent/CN104803966A/zh active Pending
- 2014-03-28 KR KR1020140036865A patent/KR101644450B1/ko active Active
- 2014-04-17 JP JP2014085186A patent/JP2015137277A/ja active Pending
- 2014-08-11 US US14/456,066 patent/US20150203466A1/en not_active Abandoned
- 2014-08-12 MY MYPI2014702242A patent/MY182857A/en unknown
-
2016
- 2016-05-11 JP JP2016095437A patent/JP6326086B2/ja active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100099894A1 (en) * | 2006-10-09 | 2010-04-22 | Jean-Luc Dubois | Method for the Synthesis of Cyclic Acetals by the Reactive Extraction of a Polyol in a Concentrated Solution |
| TW201114465A (en) * | 2009-10-19 | 2011-05-01 | Univ Nat Kaohsiung Marine | Purification process and substance for clam |
Non-Patent Citations (1)
| Title |
|---|
| VEERESA GUDUDURU, ET AL.: "Identification of Darmstoff analogs as selective agonists and antagonists of lysophosphatidic acid receptors", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MY182857A (en) | 2021-02-05 |
| US20150203466A1 (en) | 2015-07-23 |
| KR101644450B1 (ko) | 2016-08-10 |
| TW201529564A (zh) | 2015-08-01 |
| TWI553000B (zh) | 2016-10-11 |
| JP6326086B2 (ja) | 2018-05-16 |
| JP2015137277A (ja) | 2015-07-30 |
| KR20150088162A (ko) | 2015-07-31 |
| JP2016138150A (ja) | 2016-08-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105106556B (zh) | 长柱重楼抗癌活性部位pfe-pt3的化学成分分离和鉴定方法 | |
| CN102863452B (zh) | 源自山玉兰、紫玉兰、白玉兰的小白菊内酯的制备方法 | |
| CN103012356B (zh) | 一种具有α-糖苷酶抑制活性的化合物及其制备方法和用途 | |
| CN104490894B (zh) | 阔叶丰花草三萜化合物的制备方法及其在制备糖苷酶抑制剂药物中的应用 | |
| TW201335177A (zh) | 甾醇類衍生物及其製備方法與應用 | |
| CN111454317B (zh) | 具有抗炎活性的人参二醇型三萜皂苷、三七叶提取物、药物组合物和化妆品组合物 | |
| CN113999272A (zh) | 香蜂草苷的制备方法及其应用 | |
| CN109879921B (zh) | 从知母中分离的具有抗肿瘤活性的化合物及其制备方法 | |
| CN104803966A (zh) | 反式-2-19烷基-4-羟甲基-1,3-二氧戊环化合物及其制备方法 | |
| CN105837595A (zh) | 阿替洛尔的药物组合物及其在生物医药中的应用 | |
| US11147848B2 (en) | Extracts and isolated compounds from Cakile arabica for treatment of ulcer | |
| CN115073406A (zh) | 一种桉烷型倍半萜内酯类tba衍生物及其用途 | |
| CN119841724B (zh) | 一种松香烷型二萜及其制备方法和应用 | |
| CN106977561B (zh) | Sutherlandin-5-p-hydroxybenzoate的制备及其在制备治疗类风湿关节炎药物中的应用 | |
| CN115353536B (zh) | 白英中分离的萜类化合物及其制备方法和应用 | |
| CN102643317A (zh) | 一种制备芝麻素酚三葡萄糖苷的方法 | |
| US10285972B2 (en) | Trans-2-nonadecyl-4-hydroxymethyl-1,3-dioxolane and producing methodthereof | |
| CN104151375B (zh) | 一种昆仑雪菊酚苷化合物及其制备方法和用途 | |
| CN115385978B (zh) | 一种青葙子化合物及其制备方法和应用 | |
| CN104083347A (zh) | 化合物ent-kaur-16-en-19-oic acid在制备糖苷酶抑制剂药物中的应用 | |
| CN103239459A (zh) | 一种甾醇类衍生物在制备预防和/或治疗和/或辅助治疗癌症的药物中的用途 | |
| CN1760202A (zh) | 抗癌新化合物霞草苷i和制备方法及其在制药中的用途 | |
| CN107674065A (zh) | 具有抗肿瘤活性的番荔枝内酯化合物及其应用 | |
| CN105535098A (zh) | 一种薄荷叶抗氧化活性有效部位及其制备方法和应用 | |
| CN109134294B (zh) | 一种顺式双键酰胺类化合物及其制备方法与应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| EXSB | Decision made by sipo to initiate substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150729 |
|
| RJ01 | Rejection of invention patent application after publication |