KR20150091170A - 프로스타사이클린 유사체의 합성 방법 - Google Patents
프로스타사이클린 유사체의 합성 방법 Download PDFInfo
- Publication number
- KR20150091170A KR20150091170A KR1020157018095A KR20157018095A KR20150091170A KR 20150091170 A KR20150091170 A KR 20150091170A KR 1020157018095 A KR1020157018095 A KR 1020157018095A KR 20157018095 A KR20157018095 A KR 20157018095A KR 20150091170 A KR20150091170 A KR 20150091170A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- produce
- reacting
- organic solvent
- 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.)
- Ceased
Links
- 0 *O[C@@](CC[C@@]([C@@](C1)O)[C@@](Cc2ccc3)[C@@]1Cc2c3OCC(O)=O)O Chemical compound *O[C@@](CC[C@@]([C@@](C1)O)[C@@](Cc2ccc3)[C@@]1Cc2c3OCC(O)=O)O 0.000 description 21
- IPGFEAXZBBFTFN-SECBINFHSA-N [O-][N+](c1cc(C(OC[C@@H]2OC2)=O)cc([N+]([O-])=O)c1)=O Chemical compound [O-][N+](c1cc(C(OC[C@@H]2OC2)=O)cc([N+]([O-])=O)c1)=O IPGFEAXZBBFTFN-SECBINFHSA-N 0.000 description 6
- PAJMKGZZBBTTOY-ZFORQUDYSA-N CCCCC[C@@H](CC[C@@H]([C@@H](C1)O)[C@@H](C2)[C@H]1Cc1c2cccc1OCC(O)=O)O Chemical compound CCCCC[C@@H](CC[C@@H]([C@@H](C1)O)[C@@H](C2)[C@H]1Cc1c2cccc1OCC(O)=O)O PAJMKGZZBBTTOY-ZFORQUDYSA-N 0.000 description 1
- UDNIGKOHVUTSNP-LBPRGKRZSA-N CCc1cccc(OCC(O)=O)c1CCC[C@H](C)OC Chemical compound CCc1cccc(OCC(O)=O)c1CCC[C@H](C)OC UDNIGKOHVUTSNP-LBPRGKRZSA-N 0.000 description 1
- BGPHSDCIYKQODH-MRVPVSSYSA-N CO[C@H](CCC#CC#N)CN=O Chemical compound CO[C@H](CCC#CC#N)CN=O BGPHSDCIYKQODH-MRVPVSSYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/44—Separation; Purification; Stabilisation; Use of additives by treatments giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/235—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/253—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- 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
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C07F7/1852—
-
- C07F7/1856—
-
- C07C2103/14—
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/14—Benz[f]indenes; Hydrogenated benz[f]indenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261734672P | 2012-12-07 | 2012-12-07 | |
| US61/734,672 | 2012-12-07 | ||
| US201361777882P | 2013-03-12 | 2013-03-12 | |
| US61/777,882 | 2013-03-12 | ||
| PCT/US2013/073474 WO2014089385A2 (en) | 2012-12-07 | 2013-12-06 | Methods of synthesizing a prostacyclin analog |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150091170A true KR20150091170A (ko) | 2015-08-07 |
Family
ID=49881039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020157018095A Ceased KR20150091170A (ko) | 2012-12-07 | 2013-12-06 | 프로스타사이클린 유사체의 합성 방법 |
Country Status (20)
| Country | Link |
|---|---|
| US (4) | US20150315114A1 (enExample) |
| EP (2) | EP2928858B1 (enExample) |
| JP (2) | JP6342414B2 (enExample) |
| KR (1) | KR20150091170A (enExample) |
| CN (3) | CN110590547A (enExample) |
| AU (2) | AU2013355130B2 (enExample) |
| BR (1) | BR112015013085A2 (enExample) |
| CA (1) | CA2893604A1 (enExample) |
| CL (1) | CL2015001535A1 (enExample) |
| DK (1) | DK2928858T3 (enExample) |
| EA (1) | EA034309B1 (enExample) |
| ES (1) | ES2664026T3 (enExample) |
| IL (1) | IL239172B (enExample) |
| MX (2) | MX369094B (enExample) |
| NZ (1) | NZ708130A (enExample) |
| PE (1) | PE20160090A1 (enExample) |
| PH (2) | PH12015501258A1 (enExample) |
| SG (2) | SG10201600303WA (enExample) |
| TW (1) | TWI634104B (enExample) |
| WO (1) | WO2014089385A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220030006A (ko) | 2020-09-02 | 2022-03-10 | 바이오플러스 주식회사 | 미용 조성물을 포함하는 마스크 및 그 제조 방법 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20160090A1 (es) * | 2012-12-07 | 2016-02-20 | Cayman Chemical Co Inc | Metodos para sintetizar un analogo de la prostaciclina |
| US9505737B2 (en) | 2013-01-11 | 2016-11-29 | Corsair Pharma, Inc. | Treprostinil derivative compounds and methods of using same |
| US9371264B2 (en) | 2013-01-11 | 2016-06-21 | Corsair Pharma, Inc. | Treprostinil derivative compounds and methods of using same |
| WO2015073314A1 (en) * | 2013-11-13 | 2015-05-21 | Cayman Chemical Company Incorporated | Amine salts of a prostacyclin analog |
| HU231186B1 (hu) | 2014-10-08 | 2021-06-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás treprostinil és sói előállítására |
| US9394227B1 (en) | 2015-06-17 | 2016-07-19 | Corsair Pharma, Inc. | Treprostinil derivatives and compositions and uses thereof |
| US9643911B2 (en) | 2015-06-17 | 2017-05-09 | Corsair Pharma, Inc. | Treprostinil derivatives and compositions and uses thereof |
| EP3515430A1 (en) | 2016-09-26 | 2019-07-31 | United Therapeutics Corporation | Treprostinil prodrugs |
| EP3498283A1 (en) | 2017-12-14 | 2019-06-19 | Ipsol AG | Glycosidic derivatives of treprostinil |
| HU231296B1 (hu) * | 2018-03-09 | 2022-09-28 | Chinoin Zrt | Eljárás treprostinil-dietanol-amin só B polimorf formájának előállítására |
| JP6503508B2 (ja) * | 2018-08-03 | 2019-04-17 | Ｊｘｔｇエネルギー株式会社 | テトラカルボン酸二無水物、ポリイミド前駆体樹脂、ポリイミド、ポリイミド前駆体樹脂溶液、ポリイミド溶液及びポリイミドフィルム |
| JP2022546314A (ja) | 2019-08-23 | 2022-11-04 | ユナイテッド セラピューティクス コーポレイション | トレプロスチニルプロドラッグ |
| US11826327B2 (en) | 2020-04-17 | 2023-11-28 | United Therapeutics Corporation | Treatment for interstitial lung disease |
| KR20250057075A (ko) | 2020-06-09 | 2025-04-28 | 유나이티드 쎄러퓨틱스 코포레이션 | 트레프로스티닐의 푸마릴 디케토피페리딘 프로드러그 |
| JP7826317B2 (ja) | 2020-12-14 | 2026-03-09 | ユナイテッド セラピューティクス コーポレイション | トレプロスチニルプロドラッグで疾患を治療する方法 |
| EP4301372A1 (en) | 2021-03-03 | 2024-01-10 | United Therapeutics Corporation | A dry powder composition of trestinil and its prodrug thereof and further comprising comprising (e)-3,6-bis[4-(n-carbonyl-2-propenyl)amidobutyl]-2,5-diketopiperazine (fdkp) |
| US11884640B2 (en) * | 2021-06-02 | 2024-01-30 | Chirogate International Inc. | Processes and intermediates for the preparations of benzoprostacyclin analogues and benzoprostacyclin analogues prepared therefrom |
| US11884613B2 (en) * | 2022-05-05 | 2024-01-30 | Chirogate International Inc. | Processes and intermediates for the preparation of carbaprostacyclin analogues |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4306075A (en) * | 1980-03-28 | 1981-12-15 | The Upjohn Company | Composition and process |
| CA2039857A1 (en) * | 1990-04-26 | 1991-10-27 | Wilfred Po-Sum Shum | Process for producing epoxyalcohols of high optical purity |
| US6441245B1 (en) | 1997-10-24 | 2002-08-27 | United Therapeutics Corporation | Process for stereoselective synthesis of prostacyclin derivatives |
| US6700025B2 (en) | 2001-01-05 | 2004-03-02 | United Therapeutics Corporation | Process for stereoselective synthesis of prostacyclin derivatives |
| WO2005007081A2 (en) * | 2003-05-22 | 2005-01-27 | United Therapeutics Corporation | Compounds and methods for delivery of prostacyclin analogs |
| US8293715B2 (en) * | 2007-08-06 | 2012-10-23 | Taisho Pharmaceutical Co., Ltd. | 10a-Azalide compound crosslinked at 10a- and 12-positions |
| EP2252570B1 (en) | 2007-12-17 | 2017-04-05 | United Therapeutics Corporation | An improved process to prepare treprostinil, the active ingredient in remodulin ® |
| WO2009158010A1 (en) * | 2008-06-27 | 2009-12-30 | Concert Pharmaceuticals, Inc. | Prostacyclin analogs |
| WO2010039531A1 (en) * | 2008-09-23 | 2010-04-08 | Resolvyx Pharmaceuticals, Inc. | Therapeutic compounds |
| CN101891596B (zh) * | 2009-05-22 | 2013-12-11 | 上海天伟生物制药有限公司 | 一种化合物及其制备方法和用途 |
| EP2576492B1 (en) * | 2010-06-03 | 2017-09-20 | United Therapeutics Corporation | Treprostinil production |
| CA2710726C (en) * | 2010-07-22 | 2016-02-23 | Alphora Research Inc. | Synthesis of treprostinil and intermediates useful therein |
| CN103238070B (zh) | 2010-10-01 | 2016-06-29 | 丹麦国家医院 | 能够调节/保护内皮完整性的用于预防或治疗急性创伤性凝血病和心脏骤停复苏的化合物 |
| US8865898B2 (en) * | 2010-11-30 | 2014-10-21 | Japan Science And Technology Agency | Nucleoside analog or salt thereof, oligonucleotide analog, gene expression inhibitor, and nucleic-acid probe for detecting gene |
| US8524939B2 (en) | 2011-08-24 | 2013-09-03 | Chirogate International Inc. | Intermediates for the synthesis of benzindene prostaglandins and preparations thereof |
| CN102796134B (zh) * | 2012-08-31 | 2015-07-01 | 甘肃皓天化学科技有限公司 | 一种马沙骨化醇中间体的制备方法 |
| PE20160090A1 (es) * | 2012-12-07 | 2016-02-20 | Cayman Chemical Co Inc | Metodos para sintetizar un analogo de la prostaciclina |
| WO2015073314A1 (en) * | 2013-11-13 | 2015-05-21 | Cayman Chemical Company Incorporated | Amine salts of a prostacyclin analog |
-
2013
- 2013-12-06 PE PE2015000742A patent/PE20160090A1/es unknown
- 2013-12-06 CA CA2893604A patent/CA2893604A1/en not_active Abandoned
- 2013-12-06 US US14/650,234 patent/US20150315114A1/en not_active Abandoned
- 2013-12-06 WO PCT/US2013/073474 patent/WO2014089385A2/en not_active Ceased
- 2013-12-06 EP EP13812336.9A patent/EP2928858B1/en active Active
- 2013-12-06 NZ NZ708130A patent/NZ708130A/en not_active IP Right Cessation
- 2013-12-06 DK DK13812336.9T patent/DK2928858T3/en active
- 2013-12-06 SG SG10201600303WA patent/SG10201600303WA/en unknown
- 2013-12-06 EP EP18154039.4A patent/EP3398931B1/en active Active
- 2013-12-06 CN CN201910784017.3A patent/CN110590547A/zh active Pending
- 2013-12-06 CN CN201380064046.3A patent/CN104837806A/zh active Pending
- 2013-12-06 CN CN201710389417.5A patent/CN107098925B/zh not_active Expired - Fee Related
- 2013-12-06 TW TW102144990A patent/TWI634104B/zh not_active IP Right Cessation
- 2013-12-06 MX MX2015006972A patent/MX369094B/es active IP Right Grant
- 2013-12-06 KR KR1020157018095A patent/KR20150091170A/ko not_active Ceased
- 2013-12-06 JP JP2015545860A patent/JP6342414B2/ja not_active Expired - Fee Related
- 2013-12-06 SG SG11201504430TA patent/SG11201504430TA/en unknown
- 2013-12-06 ES ES13812336.9T patent/ES2664026T3/es active Active
- 2013-12-06 EA EA201591093A patent/EA034309B1/ru not_active IP Right Cessation
- 2013-12-06 BR BR112015013085A patent/BR112015013085A2/pt not_active Application Discontinuation
- 2013-12-06 AU AU2013355130A patent/AU2013355130B2/en not_active Ceased
-
2015
- 2015-06-02 MX MX2019009102A patent/MX2019009102A/es unknown
- 2015-06-03 PH PH12015501258A patent/PH12015501258A1/en unknown
- 2015-06-03 IL IL239172A patent/IL239172B/en not_active IP Right Cessation
- 2015-06-05 CL CL2015001535A patent/CL2015001535A1/es unknown
-
2017
- 2017-05-01 US US15/583,457 patent/US9908834B2/en not_active Expired - Fee Related
-
2018
- 2018-01-18 US US15/874,093 patent/US10450257B2/en not_active Expired - Fee Related
- 2018-03-15 PH PH12018500562A patent/PH12018500562A1/en unknown
- 2018-05-16 JP JP2018094605A patent/JP2018162250A/ja not_active Ceased
- 2018-09-21 AU AU2018233009A patent/AU2018233009B2/en not_active Expired - Fee Related
-
2019
- 2019-09-11 US US16/567,471 patent/US20200002261A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220030006A (ko) | 2020-09-02 | 2022-03-10 | 바이오플러스 주식회사 | 미용 조성물을 포함하는 마스크 및 그 제조 방법 |
Also Published As
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| KR20160086837A (ko) | 프로스타사이클린 유사체의 아민 염 | |
| JP5492786B2 (ja) | ゼラレノンマクロライドアナログを作製するための中間体および方法 | |
| HK1212323B (en) | Methods of synthesizing a prostacyclin analog | |
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Legal Events
| Date | Code | Title | Description |
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