KR102029898B1 - α-아사릴알데히드 에스테르, 이의 제조 방법, 및 이의 응용 - Google Patents

α-아사릴알데히드 에스테르, 이의 제조 방법, 및 이의 응용 Download PDF

Info

Publication number
KR102029898B1
KR102029898B1 KR1020177017335A KR20177017335A KR102029898B1 KR 102029898 B1 KR102029898 B1 KR 102029898B1 KR 1020177017335 A KR1020177017335 A KR 1020177017335A KR 20177017335 A KR20177017335 A KR 20177017335A KR 102029898 B1 KR102029898 B1 KR 102029898B1
Authority
KR
South Korea
Prior art keywords
compound
asaronol
formula
asronol
reaction
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
Application number
KR1020177017335A
Other languages
English (en)
Korean (ko)
Other versions
KR20170086636A (ko
Inventor
시아오훼이 쩡
팡강 칭
야쥔 바이
쉬시앙 왕
이 장
시루이 허
페이 리우
Original Assignee
노스웨스트 유니버시티
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by 노스웨스트 유니버시티 filed Critical 노스웨스트 유니버시티
Publication of KR20170086636A publication Critical patent/KR20170086636A/ko
Application granted granted Critical
Publication of KR102029898B1 publication Critical patent/KR102029898B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/78—Benzoic acid esters
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/33—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with hydroxy compounds having more than three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
    • C07C69/614—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety of phenylacetic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2121/00—Preparations for use in therapy

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Anesthesiology (AREA)
  • Emergency Medicine (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines Containing Plant Substances (AREA)
KR1020177017335A 2014-11-26 2015-11-26 α-아사릴알데히드 에스테르, 이의 제조 방법, 및 이의 응용 Active KR102029898B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN201410699506.6 2014-11-26
CN201410699506.6A CN104529775B (zh) 2014-11-26 2014-11-26 α‑细辛醇酯及其制备方法与应用
PCT/CN2015/095686 WO2016082780A1 (zh) 2014-11-26 2015-11-26 α-细辛醇酯及其制备方法与应用

Publications (2)

Publication Number Publication Date
KR20170086636A KR20170086636A (ko) 2017-07-26
KR102029898B1 true KR102029898B1 (ko) 2019-10-08

Family

ID=52845460

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020177017335A Active KR102029898B1 (ko) 2014-11-26 2015-11-26 α-아사릴알데히드 에스테르, 이의 제조 방법, 및 이의 응용

Country Status (18)

Country Link
US (1) US10131619B2 (https=)
EP (1) EP3225616B1 (https=)
JP (1) JP6506841B2 (https=)
KR (1) KR102029898B1 (https=)
CN (1) CN104529775B (https=)
AU (1) AU2015353112B2 (https=)
CA (1) CA2968652C (https=)
CY (1) CY1123193T1 (https=)
DK (1) DK3225616T3 (https=)
HU (1) HUE049249T2 (https=)
IL (1) IL252461B (https=)
MY (1) MY175619A (https=)
NZ (1) NZ732395A (https=)
PL (1) PL3225616T3 (https=)
RU (1) RU2673887C1 (https=)
SG (1) SG11201704239PA (https=)
SI (1) SI3225616T1 (https=)
WO (1) WO2016082780A1 (https=)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104529775B (zh) 2014-11-26 2017-07-14 西北大学 α‑细辛醇酯及其制备方法与应用
MX2019001455A (es) * 2016-08-04 2019-06-20 Takasago Perfumery Co Ltd Compuestos de sensacion de calor.
CN113248380B (zh) * 2020-11-23 2023-01-10 西北大学 一种乙酸α-细辛醇酯与α-细辛醇的合成方法
CN113387804B (zh) * 2021-06-04 2023-05-02 西安石油大学 乙酸α-细辛醇酯与α-细辛醇的合成方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2091366C1 (ru) * 1992-06-16 1997-09-27 Инесса Ивановна Крицкая Натриевая соль бицикло(2.2.2.)октан -2-карбоновой кислоты, проявляющая противосудорожную активность
AU2007225456B2 (en) * 2006-03-16 2013-03-28 Moleac Pte Ltd Combination therapy for treatment of patients with neurological disorders and cerebral infarction
CN101015543B (zh) 2007-02-15 2010-07-07 浙江海正药业股份有限公司 苯丙烯酸苯丙烯酯类化合物抗氧化保肝及保护脑损伤用途
CN101085129B (zh) * 2007-07-11 2010-11-10 石任兵 石菖蒲总酚提取物制备方法
CN101215226B (zh) 2008-01-02 2011-06-01 湖南师范大学 一种合成α-细辛脑的方法
CN101974011B (zh) 2010-10-26 2012-01-04 云南生物谷灯盏花药业有限公司 一种具有药用活性的新化合物灯盏细辛酸甲酯
CN102648937A (zh) 2011-02-24 2012-08-29 中国医学科学院药用植物研究所 远志碱水解产物组合物在制备抗老年性痴呆药物中的应用
CN104529724B (zh) 2014-11-26 2016-11-02 西北大学 α-细辛醇及其制备方法与应用
CN104529775B (zh) 2014-11-26 2017-07-14 西北大学 α‑细辛醇酯及其制备方法与应用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Org. Biomol. Chem. 2011, Vol.9, pp.663-666 (2010.11.26.) 1부.*

Also Published As

Publication number Publication date
KR20170086636A (ko) 2017-07-26
US20170260122A1 (en) 2017-09-14
JP6506841B2 (ja) 2019-04-24
CN104529775A (zh) 2015-04-22
HUE049249T2 (hu) 2020-09-28
IL252461A0 (en) 2017-07-31
AU2015353112A1 (en) 2017-06-22
SG11201704239PA (en) 2017-06-29
IL252461B (en) 2020-07-30
CY1123193T1 (el) 2021-10-29
DK3225616T3 (da) 2020-06-02
SI3225616T1 (sl) 2020-07-31
AU2015353112B2 (en) 2018-07-05
CA2968652C (en) 2020-07-07
WO2016082780A1 (zh) 2016-06-02
CN104529775B (zh) 2017-07-14
EP3225616A4 (en) 2018-07-11
HK1243995A1 (en) 2018-07-27
US10131619B2 (en) 2018-11-20
JP2018503602A (ja) 2018-02-08
NZ732395A (en) 2018-06-29
EP3225616B1 (en) 2020-03-04
RU2673887C1 (ru) 2018-12-03
CA2968652A1 (en) 2016-06-02
PL3225616T3 (pl) 2020-07-27
MY175619A (en) 2020-07-02
EP3225616A1 (en) 2017-10-04

Similar Documents

Publication Publication Date Title
KR102029898B1 (ko) α-아사릴알데히드 에스테르, 이의 제조 방법, 및 이의 응용
CN103113253A (zh) 一种不饱和脂肪酸醇胺衍生物及其制备方法与应用
CN111848565B (zh) 单萜基双香豆素类化合物、药物组合物及其制备方法和用途
CN102134247B (zh) 花椒毒酚衍生物及其合成方法
HK1243995B (en) Alpha-asary-laldehyde ester, preparation method therefor, and application thereof
CN107602518B (zh) 香豆素-二硫代氨基甲酸酯衍生物及其合成方法
WO2007083908A1 (en) A method for preparing decursinol from angelica gigas with high yield
JPH0952899A (ja) ロイコトリエン拮抗剤
CN102702221B (zh) Xyloketal B 类似物及其制备方法和应用
CN116284018A (zh) 一种呋喃并[2,3-b]喹啉衍生物的制备方法及其应用
CN102659639B (zh) 一种益母草碱的制备工艺
EP4043436A1 (en) Magl inhibitor, preparation method therefor and use thereof
CN113754620A (zh) 火麻仁中的木脂素酰胺类化合物及其制备方法和应用
CN104292201A (zh) 3-酯基儿茶素的制备方法
CN104447902A (zh) 一种天麻素衍生物的高收率易纯化的制备方法
JP7737955B2 (ja) ピラノベンゾピランを基本骨格とする化合物
CN104496953B (zh) 一种具有抗炎作用的化合物及其制备方法和用途
CN106699772A (zh) 一种光甘草定脂肪酸酯类衍生物及其制备方法和应用
JP2005068013A (ja) キンポウゲ科クロタネソウ属植物のアルコール抽出物とその用途
JPH0550499B2 (https=)
HK40072310A (en) Magl inhibitor, preparation method therefor and use thereof
CN101851192A (zh) 一种采用环状化合物做溶剂合成尼莫地平的方法
CN120774931A (zh) 一种倍半萜化合物、制备方法及用作乙酰胆碱酯酶抑制剂的用途
CN102924452A (zh) 5,6,7,8-四氢-2H-吡啶并[3,4-c]哒嗪-3-酮的合成方法
CN104557496B (zh) 单羰基类化合物、组合物及在制备药物中的应用

Legal Events

Date Code Title Description
A201 Request for examination
PA0105 International application

Patent event date: 20170623

Patent event code: PA01051R01D

Comment text: International Patent Application

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: 20180802

Patent event code: PE09021S01D

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

Comment text: Notification of reason for refusal

Patent event date: 20190207

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: 20190817

GRNT Written decision to grant
PR0701 Registration of establishment

Comment text: Registration of Establishment

Patent event date: 20191001

Patent event code: PR07011E01D

PR1002 Payment of registration fee

Payment date: 20191002

End annual number: 3

Start annual number: 1

PG1601 Publication of registration
PR1001 Payment of annual fee

Payment date: 20220922

Start annual number: 4

End annual number: 4

PR1001 Payment of annual fee

Payment date: 20230908

Start annual number: 5

End annual number: 5