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).Info
- 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
- Authority
- CL
- Chile
- Prior art keywords
- compound
- salt
- solvate
- tapinarof
- converting
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 31
- 239000012453 solvate Substances 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- ZISJNXNHJRQYJO-CMDGGOBGSA-N 5-[(e)-2-phenylethenyl]-2-propan-2-ylbenzene-1,3-diol Chemical class C1=C(O)C(C(C)C)=C(O)C=C1\C=C\C1=CC=CC=C1 ZISJNXNHJRQYJO-CMDGGOBGSA-N 0.000 title 2
- 229940070118 tapinarof Drugs 0.000 title 2
- 150000003839 salts Chemical class 0.000 abstract 7
- 238000004519 manufacturing process Methods 0.000 abstract 5
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 abstract 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
Classifications
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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
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- 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
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- 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
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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
- C07C39/205—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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/24—Quinones containing halogen
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
Landscapes
- 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.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201762584192P | 2017-11-10 | 2017-11-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
CL2023000154A1 true CL2023000154A1 (es) | 2023-07-07 |
Family
ID=66431171
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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). |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CL2020001226A CL2020001226A1 (es) | 2017-11-10 | 2020-05-08 | Proceso para preparar tapinarof. |
Country Status (14)
Country | Link |
---|---|
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)
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 |
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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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