CL2023000154A1 - Proceso para preparar tapinarof; compuestos intermediarios; solvato de tapinarof; forma cristalina y composición farmacéutica que la comprende (sol. div. 202001226). - Google Patents

Proceso para preparar tapinarof; compuestos intermediarios; solvato de tapinarof; forma cristalina y composición farmacéutica que la comprende (sol. div. 202001226).

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Publication number
CL2023000154A1
CL2023000154A1 CL2023000154A CL2023000154A CL2023000154A1 CL 2023000154 A1 CL2023000154 A1 CL 2023000154A1 CL 2023000154 A CL2023000154 A CL 2023000154A CL 2023000154 A CL2023000154 A CL 2023000154A CL 2023000154 A1 CL2023000154 A1 CL 2023000154A1
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CL
Chile
Prior art keywords
compound
salt
solvate
tapinarof
converting
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CL2023000154A
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English (en)
Inventor
Reddy Sudini Ravinder
Calandra Nicholas
Paul Andrews Ian
Andrew Davis Tyler
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Dermavant Sciences GmbH
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Publication of CL2023000154A1 publication Critical patent/CL2023000154A1/es

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02Compounds 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
    • C07C39/08Dihydroxy benzenes; Alkylated derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/06Preparation 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
    • C07C37/07Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/001Preparation 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
    • C07C37/002Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/205Compounds 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
    • C07C39/21Compounds 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/54Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/63Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation 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
    • C07C45/67Preparation 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
    • C07C45/68Preparation 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
    • C07C45/72Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/213Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C49/217Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/683Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00Quinones
    • C07C50/24Quinones containing halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377Preparation 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
    • C07C51/38Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235Saturated compounds containing more than one carboxyl group
    • C07C59/347Saturated compounds containing more than one carboxyl group containing keto groups
    • C07C59/353Saturated compounds containing more than one carboxyl group containing keto groups containing rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/76Unsaturated compounds containing keto groups
    • C07C59/84Unsaturated compounds containing keto groups containing six membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/03Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/08Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/28Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333Preparation 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
    • C07C67/343Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66Esters 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
    • C07C69/67Esters 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
    • C07C69/716Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/045Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05Phenols
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (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)

Abstract

Proceso para preparar un compuesto de Fórmula (I) o una sal o solvato del mismo que comprende una o más de las etapas de proceso (a), (b) y (c) en donde: (a) (i) reacción de un compuesto de Fórmula (III) para formar un compuesto (II) y (ii) la conversión del compuesto (II) en el compuesto (I) o una sal o solvato del mismo; (b) la conversión de un compuesto (VI) en un compuesto (III) y la conversión del compuesto (III) en un compuesto (I) o una sal o solvato del mismo; y (c) la conversión de un compuesto (IX) en un compuesto (VI) y después la conversión del compuesto (VI) en un compuesto (I) o una sal o solvato del mismo. Proceso para preparar un compuesto (VI) que comprende: a) condensar trans-cinamaldehído con metilisobutilcetona para formar un compuesto (VIII) b) añadir malonato de dietilo al compuesto (VIII) para formar un compuesto (VIIa) c) hidrolizar el compuesto (VIIa) para formar el compuesto (VI). Proceso para preparar un compuesto (V) o una sal del mismo que comprende descarboxilar un compuesto (VI); en presencia de una base, para formar el compuesto (V) o una sal del mismo. Proceso para preparar un compuesto (IVa), que comprende esterificar un compuesto (V) o una sal del mismo, para formar el compuesto (IVa). Proceso para preparar un compuesto 5 (IIa), que comprende halogenar un compuesto (III), para formar el compuesto (IIa). Los compuestos intermediarios de fórmulas (IIa); (IVa); (V) y (VI). Una composición farmacéutica caracterizado porque comprende una cantidad terapéuticamente eficaz del compuesto (I) de forma 1 y un excipiente farmacéuticamente aceptable.
CL2023000154A 2017-11-10 2023-01-16 Proceso para preparar tapinarof; compuestos intermediarios; solvato de tapinarof; forma cristalina y composición farmacéutica que la comprende (sol. div. 202001226). CL2023000154A1 (es)

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US201762584192P 2017-11-10 2017-11-10

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CL2023000154A1 true CL2023000154A1 (es) 2023-07-07

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CL2020001226A CL2020001226A1 (es) 2017-11-10 2020-05-08 Proceso para preparar tapinarof.
CL2023000154A CL2023000154A1 (es) 2017-11-10 2023-01-16 Proceso para preparar tapinarof; compuestos intermediarios; solvato de tapinarof; forma cristalina y composición farmacéutica que la comprende (sol. div. 202001226).

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US (4) US10647649B2 (es)
EP (1) EP3706725A4 (es)
JP (5) JP6912664B2 (es)
KR (1) KR20200087786A (es)
CN (1) CN111511357B (es)
AU (2) AU2018365241B2 (es)
BR (1) BR112020009158A2 (es)
CA (1) CA3082115A1 (es)
CL (2) CL2020001226A1 (es)
CO (1) CO2020007018A2 (es)
IL (2) IL274439B2 (es)
MX (2) MX2020004785A (es)
SG (1) SG11202002576TA (es)
WO (1) WO2019094934A1 (es)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11617724B2 (en) 2015-05-21 2023-04-04 Dermavant Sciences GmbH Topical pharmaceutical compositions
CN114042041B (zh) 2015-05-21 2023-08-22 德玛万科学有限责任公司 局部药物组合物
CA3082115A1 (en) 2017-11-10 2019-05-16 Dermavant Sciences GmbH Process for preparing tapinarof
US11497718B2 (en) 2018-11-13 2022-11-15 Dermavant Sciences GmbH Use of tapinarof for the treatment of atopic dermatitis
CN115884959A (zh) * 2020-04-22 2023-03-31 耶路撒冷希伯来大学伊森姆研究发展有限公司 生物活性的苯酚盐离子络合物
EP4153551A1 (en) 2020-05-19 2023-03-29 Teva Pharmaceuticals International GmbH Solid state forms of tapinarof
JP2023550085A (ja) * 2020-11-23 2023-11-30 ダーマバント、サイエンシーズ、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツング タピナロフのゲル、軟膏、およびフォーム製剤ならびに使用方法
CN115703700A (zh) * 2021-08-03 2023-02-17 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

Family Cites Families (43)

* 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
EP0170105B1 (en) 1984-07-07 1990-10-17 Koichi Prof. Dr. Shudo Benzoic acid derivatives
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
CA2135488A1 (en) 1993-03-10 1994-09-15 Koichi Hashimoto Stilbene derivative and stilbene analog derivative, and use thereof
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
WO1999059561A2 (en) 1998-05-18 1999-11-25 Hensley, Kenneth, L. Resveratrol inhibition of myeloperoxidase
FR2785284B1 (fr) 1998-11-02 2000-12-01 Galderma Res & Dev Analogues de la vitamine d
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
CA2393297C (en) 1999-12-06 2010-10-05 Welichem Biotech Inc. Polyhydroxystilbenes as antipsoriatic agents and protein kinase inhibitors
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
EP1368306B1 (en) * 2001-01-18 2013-01-16 Welichem Biotech Inc. Novel 1,2-diphenylethene derivatives for treatment of immune diseases
WO2003009807A2 (en) 2001-07-23 2003-02-06 Galileo Laboratories, Inc. Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods
JP2006508930A (ja) 2002-10-01 2006-03-16 ウェリケム バイオテック インコーポレーテッド 新規生物活性ジフェニルエテン化合物およびその治療への適用
US9308239B2 (en) 2008-02-26 2016-04-12 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
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
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
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
CN103992212B (zh) * 2014-05-29 2015-07-01 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
ES2829637T3 (es) 2014-12-12 2021-06-01 Dermavant Sciences GmbH 3,5-dihidroxi-4-isopropil-trans-estilbeno para su uso en el tratamiento tópico del acné
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
CN114042041B (zh) 2015-05-21 2023-08-22 德玛万科学有限责任公司 局部药物组合物
US11617724B2 (en) 2015-05-21 2023-04-04 Dermavant Sciences GmbH Topical pharmaceutical compositions
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
CA3082115A1 (en) 2017-11-10 2019-05-16 Dermavant Sciences GmbH Process for preparing tapinarof
EP4153551A1 (en) 2020-05-19 2023-03-29 Teva Pharmaceuticals International GmbH Solid state forms of tapinarof

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