KR101644450B1 - 트랜스-2-노나데실-4-히드록시메틸-1,3-다이옥살란 화합물 및 그 제조방법 - Google Patents
트랜스-2-노나데실-4-히드록시메틸-1,3-다이옥살란 화합물 및 그 제조방법 Download PDFInfo
- Publication number
- KR101644450B1 KR101644450B1 KR1020140036865A KR20140036865A KR101644450B1 KR 101644450 B1 KR101644450 B1 KR 101644450B1 KR 1020140036865 A KR1020140036865 A KR 1020140036865A KR 20140036865 A KR20140036865 A KR 20140036865A KR 101644450 B1 KR101644450 B1 KR 101644450B1
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- nonadecyl
- hydroxymethyl
- present
- 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.)
- Active
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006640 acetylation reaction Methods 0.000 claims abstract description 4
- 238000007254 oxidation reaction Methods 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
- 230000021736 acetylation Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000004480 active ingredient Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 208000019425 cirrhosis of liver Diseases 0.000 description 9
- 208000019423 liver disease Diseases 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 206010019668 Hepatic fibrosis Diseases 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000011149 active material Substances 0.000 description 3
- 229910052602 gypsum Inorganic materials 0.000 description 3
- 239000010440 gypsum Substances 0.000 description 3
- 241000411851 herbal medicine Species 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 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 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000002354 daily effect Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000015872 dietary supplement Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000003494 hepatocyte Anatomy 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- 241000193882 Corbicula Species 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
- 206010016654 Fibrosis 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
- 235000002789 Panax ginseng Nutrition 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical class [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000003510 anti-fibrotic effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 231100000012 chronic liver injury Toxicity 0.000 description 1
- 229960001338 colchicine Drugs 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000002443 hepatoprotective effect Effects 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
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 (2)
| Publication Number | Publication Date |
|---|---|
| KR20150088162A KR20150088162A (ko) | 2015-07-31 |
| KR101644450B1 true KR101644450B1 (ko) | 2016-08-10 |
Family
ID=53544198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020140036865A Active KR101644450B1 (ko) | 2014-01-23 | 2014-03-28 | 트랜스-2-노나데실-4-히드록시메틸-1,3-다이옥살란 화합물 및 그 제조방법 |
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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201114465A (en) * | 2009-10-19 | 2011-05-01 | Univ Nat Kaohsiung Marine | Purification process and substance for clam |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2906807A1 (fr) * | 2006-10-09 | 2008-04-11 | Arkema France | Procede de synthese d'acetals cycliques par extraction reactive d'un polyol en solution concentree |
| 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201114465A (en) * | 2009-10-19 | 2011-05-01 | Univ Nat Kaohsiung Marine | Purification process and substance for clam |
Non-Patent Citations (1)
| Title |
|---|
| Bioorganic & Medicinal Chemistry Letters, 16, 451-456, 2006* |
Also Published As
| Publication number | Publication date |
|---|---|
| MY182857A (en) | 2021-02-05 |
| US20150203466A1 (en) | 2015-07-23 |
| TW201529564A (zh) | 2015-08-01 |
| CN104803966A (zh) | 2015-07-29 |
| 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 |
|---|---|---|
| CN102863452B (zh) | 源自山玉兰、紫玉兰、白玉兰的小白菊内酯的制备方法 | |
| Jiang et al. | Glucose-lowering activity of novel tetrasaccharide glyceroglycolipids from the fruits of Cucurbita moschata | |
| CN105732381B (zh) | 牛樟芝提取物及其制备方法和应用 | |
| US9884884B2 (en) | Compound extracted from husk and fruit stem of xanthoceras sobifolia and its extracting method and use thereof | |
| CN102241684A (zh) | 小白菊内酯的制备方法 | |
| CN104606184B (zh) | 葫芦七中6‑羟基‑艾里莫芬‑7(11)‑烯‑12,8‑内酯的抗炎应用及其提取方法 | |
| KR101644450B1 (ko) | 트랜스-2-노나데실-4-히드록시메틸-1,3-다이옥살란 화합물 및 그 제조방법 | |
| Lu et al. | Cembranoids from the soft corals Sinularia granosa and Sinularia querciformis | |
| CN113999272A (zh) | 香蜂草苷的制备方法及其应用 | |
| JP2005179339A (ja) | 新規化合物および医薬組成物 | |
| KR19980044054A (ko) | 신규한 트리테르펜 글리코사이드 화합물, 그의 제조방법 및 그를 함유하는 항암제 조성물 | |
| Singh et al. | A new pentacyclic triterpene acid from Lantana indica | |
| Priya et al. | Bioactive constituents from Tinospora cordifolia (willd.): Isolation, synthesis and their immunomodulatory activity | |
| Lu et al. | Anti-inflammatory cembranoids from the Formosan soft coral Sinularia discrepans | |
| US11147848B2 (en) | Extracts and isolated compounds from Cakile arabica for treatment of ulcer | |
| Maia et al. | New ceramides from Acnistus arborescens | |
| CN102643317A (zh) | 一种制备芝麻素酚三葡萄糖苷的方法 | |
| CN104151375B (zh) | 一种昆仑雪菊酚苷化合物及其制备方法和用途 | |
| CN119841724B (zh) | 一种松香烷型二萜及其制备方法和应用 | |
| Cha et al. | Two new amino acid-sesquiterpene lactone conjugates from Ixeris dentata | |
| US10285972B2 (en) | Trans-2-nonadecyl-4-hydroxymethyl-1,3-dioxolane and producing methodthereof | |
| CN107674065A (zh) | 具有抗肿瘤活性的番荔枝内酯化合物及其应用 | |
| Rasool et al. | A new cycloartane-type triterpene from Pentatropis spiralis | |
| JPS5910600A (ja) | β−エクジソンの製造法 | |
| CN1563026A (zh) | 从苦玄参中提取的苯乙醇苷类化合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 20140328 |
|
| PA0201 | Request for examination | ||
| PG1501 | Laying open of application | ||
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20151110 Patent event code: PE09021S01D |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20160607 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20160726 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20160727 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| FPAY | Annual fee payment |
Payment date: 20190725 Year of fee payment: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20190725 Start annual number: 4 End annual number: 4 |
|
| PR1001 | Payment of annual fee |
Payment date: 20200423 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 20210330 Start annual number: 6 End annual number: 6 |
|
| PR1001 | Payment of annual fee |
Payment date: 20220524 Start annual number: 7 End annual number: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 20240429 Start annual number: 9 End annual number: 9 |