CN111511357B - 用于制备他品洛夫的方法 - Google Patents

用于制备他品洛夫的方法 Download PDF

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CN111511357B
CN111511357B CN201880071224.8A CN201880071224A CN111511357B CN 111511357 B CN111511357 B CN 111511357B CN 201880071224 A CN201880071224 A CN 201880071224A CN 111511357 B CN111511357 B CN 111511357B
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formula
compound
salt
viii
iva
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CN111511357A (zh
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I.P.安德鲁斯
N.卡兰德拉
T.A.戴维斯
R.R.苏迪尼
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Demavan Science Co ltd
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Demavan Science Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
    • C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
    • C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
    • C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C49/217—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/24—Quinones containing halogen
    • 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
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
    • 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
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/347—Saturated compounds containing more than one carboxyl group containing keto groups
    • C07C59/353—Saturated compounds containing more than one carboxyl group containing keto groups containing rings
    • 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
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • 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
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • 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
    • C07C69/67—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 saturated acids
    • C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Compounds Of Unknown Constitution (AREA)
  • Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CN201880071224.8A 2017-11-10 2018-11-13 用于制备他品洛夫的方法 Active CN111511357B (zh)

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US201762584192P 2017-11-10 2017-11-10
US62/584,192 2017-11-10
PCT/US2018/060749 WO2019094934A1 (en) 2017-11-10 2018-11-13 Process for preparing tapinarof

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CN111511357B true CN111511357B (zh) 2024-04-09

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KR (1) KR102773538B1 (enExample)
CN (1) CN111511357B (enExample)
AU (2) AU2018365241B2 (enExample)
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CL (3) CL2020001226A1 (enExample)
CO (1) CO2020007018A2 (enExample)
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MX (2) MX2020004785A (enExample)
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Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUE059066T2 (hu) 2015-05-21 2022-10-28 Dermavant Sciences GmbH Topikus gyógyszerkészítmények
US11617724B2 (en) 2015-05-21 2023-04-04 Dermavant Sciences GmbH Topical pharmaceutical compositions
EP3706725A4 (en) 2017-11-10 2021-08-25 Dermavant Sciences GmbH PROCESS FOR THE PREPARATION OF TAPINAROF
US11497718B2 (en) 2018-11-13 2022-11-15 Dermavant Sciences GmbH Use of tapinarof for the treatment of atopic dermatitis
WO2021214762A1 (en) * 2020-04-22 2021-10-28 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Bioactive phenolate ionic complexes
EP4153551A1 (en) 2020-05-19 2023-03-29 Teva Pharmaceuticals International GmbH Solid state forms of tapinarof
MX2023005658A (es) * 2020-11-23 2023-09-07 Dermavant Sciences GmbH Formulaciones de gel, ungüento y espuma de tapinarof y metodos de uso.
CN115703700B (zh) * 2021-08-03 2024-08-16 北京颖泰嘉和生物科技股份有限公司 1,3-环己二酮的制备方法
WO2023067606A1 (en) * 2021-10-21 2023-04-27 Sol-Gel Technologies Ltd. Crystalline polymorph of tapinarof
WO2025021674A2 (en) 2023-07-21 2025-01-30 Interquim, S.A. Process for the preparation of tapinarof
WO2025031935A1 (en) 2023-08-04 2025-02-13 Sandoz Ag Crystalline forms of tapinarof
WO2025043084A2 (en) * 2023-08-24 2025-02-27 Taro Pharmaceutical Industries Ltd. Methods of preparing tapinarof and related compounds
IT202300023508A1 (it) 2023-11-08 2025-05-08 Procos Spa Processo per la preparazione della forma polimorfa iii di tapinarof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103172497A (zh) * 2011-12-23 2013-06-26 重庆市科学技术研究院 治疗牛皮癣新药苯烯莫德的工业化生产工艺
CN103992212A (zh) * 2014-05-29 2014-08-20 河北科技大学 顺式苯烯莫德的合成方法及顺式苯烯莫德的应用

Family Cites Families (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1442295A (fr) 1964-10-08 1966-06-17 Smith Kline French Lab Nouveaux dérivés de l'acide beta, beta-diphényl acrylique et leur procédé de préparation
JPS5111748A (en) 1974-07-16 1976-01-30 Taisho Pharmaceutical Co Ltd Suchirubenjudotaino seizoho
JPS5721341A (en) * 1980-07-15 1982-02-04 Nippon Zeon Co Ltd Preparation of substituted acetic ester
JPS58159410A (ja) 1982-03-18 1983-09-21 Mitsubishi Chem Ind Ltd 抗炎症剤
US4515883A (en) 1983-04-14 1985-05-07 Ricoh Company, Ltd. Stilbene derivatives, distyryl derivatives and electrophotographic photoconductor comprising at least one of the derivatives
DE3580134D1 (de) 1984-07-07 1990-11-22 Shudo Koichi Prof Dr Chem Benzoesaeurederivate.
ES2056983T3 (es) 1988-03-21 1994-10-16 Boehringer Ingelheim Pharma Compuestos para inhibir la biosintesis de metabolitos de acido araquidonico derivados de lipoxigenasa.
GB8915104D0 (en) 1989-06-30 1989-08-23 Beecham Group Plc Chemical process
US5268517A (en) 1989-07-14 1993-12-07 Basf Aktiengesellschaft Stereoselective preparation of Z-1,2-diarylallyl chlorides and the conversion thereof into azolylmethyloxiranes, and novel intermediates
GB9106177D0 (en) 1991-03-22 1991-05-08 Aston Molecules Ltd Substituted diphenylethylenes and analogues or derivatives thereof
JPH06135948A (ja) 1992-10-30 1994-05-17 Taiho Yakuhin Kogyo Kk スチレン誘導体又はその塩
DE69418947T2 (de) 1993-03-10 1999-12-23 Morinaga Milk Industry Co. Ltd., Tokio/Tokyo Stilbenderivate und analoga sowie deren anwendung
JPH0753359A (ja) 1993-06-11 1995-02-28 Kao Corp リポキシゲナーゼ阻害剤
WO1996041789A1 (fr) * 1995-06-08 1996-12-27 Firmenich S.A. Procede pour l'obtention de cetones cycloaliphatiques insaturees
JPH1072330A (ja) 1996-09-03 1998-03-17 Kansai Kouso Kk チロシナーゼ活性阻害剤及び化粧料
FR2777183B1 (fr) 1998-04-10 2001-03-02 Oreal Utilisation d'au moins un hydroxystilbene dans une composition destinee a favoriser la desquamation de la peau et composition le comprenant
US6624197B1 (en) 1998-05-08 2003-09-23 Calyx Therapeutics, Inc. Diphenylethylene compounds
AU4084599A (en) 1998-05-18 1999-12-06 Oklahoma Medical Research Foundation Resveratrol inhibition of myeloperoxidase
FR2785284B1 (fr) 1998-11-02 2000-12-01 Galderma Res & Dev Analogues de la vitamine d
CN1319959C (zh) * 1999-12-06 2007-06-06 天济药业（深圳）有限公司 抗发炎、治疗牛皮癣和抑制蛋白质致活酶的羟基芪、芪衍生物及其类似物
US20080255245A1 (en) * 1999-12-06 2008-10-16 Welichem Biotech Inc. Anti-Inflammatory and Psoriasis Treatment and Protein Kinase Inhibition by Hydroxystilbenes and Novel Stilbene Derivatives and Analogues
US7321050B2 (en) 1999-12-06 2008-01-22 Welichem Biotech Inc. Anti-inflammatory and psoriasis treatment and protein kinase inhibition by hydroxy stilbenes and novel stilbene derivatives and analogues
JP2001261585A (ja) 2000-03-15 2001-09-26 Chemiprokasei Kaisha Ltd ハロゲン化ビニル化合物の合成法
US6552085B2 (en) 2000-08-16 2003-04-22 Insmed Incorporated Compositions containing hypoglycemically active stilbenoids
US6410596B1 (en) 2000-08-16 2002-06-25 Insmed Incorporated Compositions containing hypoglycemically active stillbenoids
KR100836207B1 (ko) 2001-01-18 2008-06-09 웰리켐 바이오 테크 인크. 면역 질환 치료용의 신규한 1,2-디페닐에텐 유도체
WO2003009807A2 (en) 2001-07-23 2003-02-06 Galileo Laboratories, Inc. Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods
CA2501663A1 (en) 2002-10-01 2004-04-15 Welichem Biotech Inc. Stilbene derivatives having an immune-modulating activity
WO2009108762A2 (en) 2008-02-26 2009-09-03 The Penn State Research Foundation Methods and compositions for treatment of retinoid-responsive conditions
JP4426633B2 (ja) * 2008-04-11 2010-03-03 花王株式会社 ２−アルキル−２−シクロアルケン−１−オンの製造方法
US8524782B2 (en) 2008-07-23 2013-09-03 Laurus Labs Private Limited Key intermediate for the preparation of Stilbenes, solid forms of Pterostilbene, and methods for making the same
CN101531571B (zh) 2009-04-17 2013-03-20 河北科技大学 六次甲基四胺氧化合成二苯乙烯类化合物的方法
CN101564537B (zh) 2009-06-08 2011-05-25 河北科技大学 3，5-二羟基-4-异丙基二苯乙烯-溴乙酸乙酯-聚乙二醇复合物及其合成方法
CN101648851B (zh) * 2009-09-03 2012-10-10 河北科技大学 (e)-3,5-二羟基-4-异丙基二苯乙烯的清洁制备方法
CN104003848B (zh) * 2013-02-25 2016-02-10 武汉诺安药业有限公司 （e）-3,5-二羟基-4-异丙基二苯乙烯制备方法
EP3229840B1 (en) 2014-12-12 2020-09-09 Dermavant Sciences GmbH 3,5-dihydroxy-4-isopropyl-trans-stilbene for use in the topical treatment of acne
CN105884581A (zh) * 2014-12-30 2016-08-24 上海复星医药产业发展有限公司 苯烯莫德的制备方法
US11617724B2 (en) 2015-05-21 2023-04-04 Dermavant Sciences GmbH Topical pharmaceutical compositions
HUE059066T2 (hu) * 2015-05-21 2022-10-28 Dermavant Sciences GmbH Topikus gyógyszerkészítmények
WO2019063002A1 (zh) 2017-09-30 2019-04-04 北京文丰天济医药科技有限公司 苯烯莫德的晶型及其用途与制备方法
EP3706725A4 (en) 2017-11-10 2021-08-25 Dermavant Sciences GmbH PROCESS FOR THE PREPARATION OF TAPINAROF
EP4153551A1 (en) 2020-05-19 2023-03-29 Teva Pharmaceuticals International GmbH Solid state forms of tapinarof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103172497A (zh) * 2011-12-23 2013-06-26 重庆市科学技术研究院 治疗牛皮癣新药苯烯莫德的工业化生产工艺
CN103992212A (zh) * 2014-05-29 2014-08-20 河北科技大学 顺式苯烯莫德的合成方法及顺式苯烯莫德的应用

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Crystalline Polymorphism of Organic Compounds;Mino R. Caira;《Topics in Current Chemistry,》;19981231;第198卷;163-208 *

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