JP7377981B2 - デクルシン誘導体の新規な合成方法 - Google Patents
デクルシン誘導体の新規な合成方法 Download PDFInfo
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- 238000001308 synthesis method Methods 0.000 title description 4
- 239000000243 solution Substances 0.000 claims description 47
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000002156 mixing Methods 0.000 claims description 18
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 230000002194 synthesizing effect Effects 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 9
- RUROFEVDCUGKHD-UHFFFAOYSA-N 3-bromoprop-1-enylbenzene Chemical compound BrCC=CC1=CC=CC=C1 RUROFEVDCUGKHD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
- 239000012312 sodium hydride Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- KTTIANPTCWGYCN-JLXBBBJOSA-N (3s)-2,2-dimethyl-3-[(e)-3-phenylprop-2-enoxy]-3,4-dihydropyrano[3,2-g]chromen-8-one Chemical compound O([C@H]1CC2=CC=3C=CC(=O)OC=3C=C2OC1(C)C)C\C=C\C1=CC=CC=C1 KTTIANPTCWGYCN-JLXBBBJOSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 208000025500 Hutchinson-Gilford progeria syndrome Diseases 0.000 description 4
- 208000007932 Progeria Diseases 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BGXFQDFSVDZUIW-UHFFFAOYSA-N Decursinol Natural products O1C(=O)C=CC2=C1C=C1OC(C)(C)C(O)CC1=C2 BGXFQDFSVDZUIW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- BGXFQDFSVDZUIW-LBPRGKRZSA-N decursinol Chemical compound O1C(=O)C=CC2=C1C=C1OC(C)(C)[C@@H](O)CC1=C2 BGXFQDFSVDZUIW-LBPRGKRZSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- RUROFEVDCUGKHD-QPJJXVBHSA-N [(e)-3-bromoprop-1-enyl]benzene Chemical compound BrC\C=C\C1=CC=CC=C1 RUROFEVDCUGKHD-QPJJXVBHSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- YCYMCMYLORLIJX-SNVBAGLBSA-N (2r)-2-propyloctanoic acid Chemical compound CCCCCC[C@H](C(O)=O)CCC YCYMCMYLORLIJX-SNVBAGLBSA-N 0.000 description 1
- -1 3-bromo-propenyl Chemical group 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- 208000007446 Hip Dislocation Diseases 0.000 description 1
- 208000026350 Inborn Genetic disease Diseases 0.000 description 1
- 206010023204 Joint dislocation Diseases 0.000 description 1
- 206010023230 Joint stiffness Diseases 0.000 description 1
- 102000008201 Lamin Type A Human genes 0.000 description 1
- 108010021099 Lamin Type A Proteins 0.000 description 1
- 206010063493 Premature ageing Diseases 0.000 description 1
- 208000032038 Premature aging Diseases 0.000 description 1
- 208000037340 Rare genetic disease Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 208000006011 Stroke Diseases 0.000 description 1
- 208000037063 Thinness Diseases 0.000 description 1
- 201000011032 Werner Syndrome Diseases 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 210000004905 finger nail Anatomy 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 208000016361 genetic disease Diseases 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 210000000633 nuclear envelope Anatomy 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000037432 silent mutation Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
- 210000004003 subcutaneous fat Anatomy 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 206010048828 underweight Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Claims (5)
- (I)シンナミルブロミドとN-メチル-2-ピロリドン[NMP]溶媒とを混合して溶液を製造する段階と、
(II)デクルシノールとテトラヒドロフラン(THF)溶媒及び水素化ナトリウム(NaH)とを混合して溶液を製造する段階と、
(III)前記(I)及び(II)段階で製造された溶液を混合して、下記化学式1で表されるデクルシン誘導体を収得する段階と、
を含み、
前記デクルシン誘導体を収得する段階は、
前記(III)段階で製造された混合溶液をpH7以下に調節する段階(第1段階)と、
前記第1段階の溶液から有機層を収得する段階(第2段階)と、
前記第2段階で収得された有機層を減圧濃縮して反応溶液を収得する段階(第3段階)と、
前記第3段階で収得された反応溶液を熱処理及び冷却後、濾過、乾燥させてデクルシン誘導体を収得する段階(第4段階)と、
を含む、デクルシン誘導体の合成方法:
- 前記シンナミルブロミドとNMPは、1:(5~10)の重量比で含まれることを特徴とする、請求項1に記載のデクルシン誘導体の合成方法。
- 前記デクルシノールとTHF及びNaHは、(5~10):(50~100):1の重量比で含まれることを特徴とする、請求項1に記載のデクルシン誘導体の合成方法。
- 前記収得されたデクルシン誘導体を再結晶する段階をさらに含むことを特徴とする、請求項1から請求項3のうち何れか一項に記載のデクルシン誘導体の合成方法。
- 前記再結晶する段階は、
収得されたデクルシン誘導体にアセトンを混合して反応溶液を製造する段階(第1段階)と、
前記第1段階の反応溶液にシードを混合して反応溶液を製造する段階(第2段階)と、
前記第2段階の反応溶液をイソプロピルアルコールと混合して減圧濃縮する段階(第3段階)と、
前記第3段階で減圧濃縮された溶液を濾過、乾燥させてデクルシン誘導体を収得する段階(第4段階)と、
を含むことを特徴とする、請求項4に記載のデクルシン誘導体の合成方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2019-0174080 | 2019-12-24 | ||
KR1020190174080A KR102283391B1 (ko) | 2019-12-24 | 2019-12-24 | 데커신 유도체의 신규 합성방법 |
PCT/KR2020/015492 WO2021132872A1 (ko) | 2019-12-24 | 2020-11-06 | 데커신 유도체의 신규 합성방법 |
Publications (2)
Publication Number | Publication Date |
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JP2023508962A JP2023508962A (ja) | 2023-03-06 |
JP7377981B2 true JP7377981B2 (ja) | 2023-11-10 |
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Application Number | Title | Priority Date | Filing Date |
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JP2022539009A Active JP7377981B2 (ja) | 2019-12-24 | 2020-11-06 | デクルシン誘導体の新規な合成方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20230063754A1 (ja) |
EP (1) | EP4083045B1 (ja) |
JP (1) | JP7377981B2 (ja) |
KR (1) | KR102283391B1 (ja) |
CN (1) | CN114867728A (ja) |
WO (1) | WO2021132872A1 (ja) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016522821A (ja) | 2013-05-08 | 2016-08-04 | フイルメニツヒ ソシエテ アノニムFirmenich Sa | プロ香気化合物 |
WO2018199633A1 (ko) | 2017-04-25 | 2018-11-01 | (주)피알지에스앤텍 | 데커신 유도체를 유효성분으로 함유하는 노화 관련 질환 예방 또는 치료용 약학조성물 |
Family Cites Families (4)
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KR20090037185A (ko) * | 2007-10-11 | 2009-04-15 | 박용진 | (-)-데쿠르신 유도체를 포함하는 아토피성 피부염 질환의치료 및 예방용 조성물 |
KR20100008808A (ko) * | 2008-07-17 | 2010-01-27 | 박용진 | 신규 (+)-데쿠르신-에테르 유도체를 포함하는 아토피성피부염 질환의 치료 및 예방용 조성물 |
US10811150B2 (en) | 2016-08-16 | 2020-10-20 | Ge-Hitachi Nuclear Energy Americas Llc | Remotely operated vehicles, systems, and methods for inspecting core shrouds |
KR102070328B1 (ko) * | 2017-04-25 | 2020-01-28 | (주)피알지에스앤텍 | 데커신 유도체를 유효성분으로 함유하는 노화 관련 질환 예방 또는 치료용 약학조성물 |
-
2019
- 2019-12-24 KR KR1020190174080A patent/KR102283391B1/ko active IP Right Grant
-
2020
- 2020-11-06 JP JP2022539009A patent/JP7377981B2/ja active Active
- 2020-11-06 US US17/787,937 patent/US20230063754A1/en active Pending
- 2020-11-06 EP EP20906725.5A patent/EP4083045B1/en active Active
- 2020-11-06 CN CN202080089277.XA patent/CN114867728A/zh active Pending
- 2020-11-06 WO PCT/KR2020/015492 patent/WO2021132872A1/ko unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016522821A (ja) | 2013-05-08 | 2016-08-04 | フイルメニツヒ ソシエテ アノニムFirmenich Sa | プロ香気化合物 |
WO2018199633A1 (ko) | 2017-04-25 | 2018-11-01 | (주)피알지에스앤텍 | 데커신 유도체를 유효성분으로 함유하는 노화 관련 질환 예방 또는 치료용 약학조성물 |
Non-Patent Citations (1)
Title |
---|
社団法人日本化学会,実験化学ガイドブック,丸善株式会社,1992年,第130-131頁 |
Also Published As
Publication number | Publication date |
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KR102283391B1 (ko) | 2021-07-30 |
CN114867728A (zh) | 2022-08-05 |
KR20210081793A (ko) | 2021-07-02 |
JP2023508962A (ja) | 2023-03-06 |
WO2021132872A1 (ko) | 2021-07-01 |
EP4083045A1 (en) | 2022-11-02 |
EP4083045A4 (en) | 2023-05-24 |
EP4083045B1 (en) | 2023-12-13 |
US20230063754A1 (en) | 2023-03-02 |
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