(Z)-7-((1R,2R,3R,5S)-3-(Tert-Butyldimethylsilyloxy)-2-((S,E)-3-(Tert-Butyldimethylsilyloxy)-5-Phenylpent-1-Enyl)-5-Hydroxycyclopentyl)-N-Ethylhept-5-Enamide 反应生成比马前列素 参考文献:Novel Process For The Preparation Of Prostaglandins And Intermediates Thereof 标题:Novel Process For The Preparation Of Prostaglandins And Intermediates Thereof 摘要:本发明涉及一种新型的制备具有式(k)的前列腺素化合物的方法,其中r选自以下组中的一种:C1-C7烷基;C7-C17芳基烷基,其中芳基基团未取代或取代有1至3个取代基,所述取代基选自c1-C6烷基,卤素和cf3;以及(ch2)nor2,其中n为1至3,R2代表未取代或取代有1至3个取代基的c6-C10芳基基团,所述取代基选自c1-C6烷基,卤素和cf3;R1选自or3和nhr3,其中r3为c1-C6烷基,H;虚线表示双键或单键.本发明还公开了新型中间体.
专利号:EP-1721894-A1 优先权日:2005-05-13 标题 :Process for the synthesis of prostaglandin derivatives 发明人:LISI GIUSEPPE 权利人:TECHNOPHARMA SA 摘要:An alternative method for the synthesis of prostaglandin F analogues, in particular, analogues of PGF 2α and specifically for the synthesis of latano-prost, wherein the transformation of the lactone intermediate (5)n ninto the corresponding lactol (7)n nis carried out by treating the lactone intermediate (5) with a silane, preferably polymethylhydrosiloxane (PMHS), in the presence of a titanocene - and preferably titanocene fluoride. n The method enables considerable production economies with respect to the conventional reduction of lactone with diisobutylaluminum hydride (DIBAL-H).
专利号:US-2015031898-A1 优先权日:2012-03-09 标题 :Process for preparation of prostaglandin f2 alpha analogues 发明人:DAMS IWONA; KUTNER ANDRZEJ; CHODYNSKI MICHAL; KRUPA MALGORZATA; PIETRASZEK ANITA; ZEZULA MARTA; CMOCH PIOTR; KOSINSKA MONIKA 权利人:INST FARMACEUTYCZNY 摘要:A convergent synthesis of the prostaglandin F 2α analogues, travoprost and bimatoprost, was developed employing Julia-Lythgoe olefination of the structurally advanced phenylsulfone with an enantiomerically pure aldehyde ω-chain synthon. The novel convergent strategy allows the synthesis of a whole series of prostaglandin analogues of high purity from a common and structurally advanced prostaglandin intermediate.
专利号:US-10100028-B2 优先权日:2013-09-30 标 题:Synthesis routes for prostaglandins and prostaglandin intermediates using metathesis 发明人:YIANNIKOUROS GEORGE PETROS; KALARITIS PANOS; GAMAGE CHAMINDA PRIYAPUSHPA; AREFYEV DENIS VIKTOROVICH 权利人:IRIX PHARMACEUTICALS INC; PATHEON API SERVICES INC 摘要:Methods of synthesizing prostaglandins, prostaglandin analogs and their synthetic intermediates are described. The methods can comprise metal-catalyzed metathesis reactions. Also provided are synthetic intermediates that can be used in the synthesis of the prostaglandins and prostaglandin analogs.
专利号:US-7157590-B2 优先权日:2001-05-31 标题 :Process for the preparation of 17-phenyl-18,19,20-thinor-pgf 2a and its derivatives 发明人:GUTMAN ARIE; NISNEVICH GENNADY; ETINGER MARINA; ZALTZMAN IGOR; YUDOVITCH LEV; PERTSIKOV BORIS 权利人:FINETECH LAB LTD 摘要:The present invention provides a new and effective process for the synthesis of 17-phenyl-18,19,20-trinor-PGF 2α and its derivatives, including the anti-glaucoma drugs Bimatoprost and Latanoprost. The benefit of the present invention rises inter alia from the fact that a major intermediate involved in the synthesis of the above compounds may be isolated from a mixture containing also an undesired isomer, by crystallization. In addition, the undesired isomer may be oxidized to give the starting compound, which is then recycled.
专利号:US-2014046086-A1 优先权日:2012-08-10 标题:Process for the preparation of tafluprost and intermediates thereof 发明人:WEN WEN-HSIEN 权利人:SCINOPHARM CHANGSHU PHARMACEUTICALS LTD 摘要:The present invention provides efficient, economical and environmental friendly methods for synthesis of prostaglandin analogs including tafluprost and intermediates thereof. The invention involves a selective oxidation using in situ boronate ester protection and a unique crystallization method to remove the undesired isomers of fluorinated intermediates.
专利号:US-8476471-B2 优先权日:2009-07-13 标 题 :Synthesis of prostanoids 发明人:YIANNIKOUROS GEORGE PETROS; KALARITIS PANOS; GAMAGE CHAMINDA PRIYAPUSHPA; ABERNATHY STEPHANIE BOSSE 权利人:YIANNIKOUROS GEORGE PETROS; KALARITIS PANOS; GAMAGE CHAMINDA PRIYAPUSHPA; ABERNATHY STEPHANIE BOSSE; IRIX PHARMACEUTICALS INC 摘要:The presently disclosed subject matter provides a method of synthesizing prostaglandins and prostaglandin analogs comprising the ring closing metathesis of compounds of Formula (I). Also provided are novel compounds of Formula (I) and Formula (II). In addition to their use as synthetic intermediates in the presently disclosed methods, compounds of Formula (II) can be used as prostaglandin and/or prostaglandin analog prodrugs.
1: Vagiakis I, Papadopoulou EP, Amaxilati E, Tsiropoulos GN, Konstas AG, Panos GD. Bimatoprost Intracameral Implant (Durysta®): A New Era in Glaucoma Management Through Sustained-Release Innovation. Drug Des Devel Ther. 2025 Jan 31;19:703-714. doi: 10.2147/DDDT.S506520. 2: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Bimatoprost. 2024 Dec 15. 17(5):561. doi: 10.3390/ph17050561. 4: Sirinek PE, Lin MM. Intracameral sustained release bimatoprost implants (Durysta). Semin Ophthalmol. 2022 Apr 3;37(3):385-390. doi: 10.1080/08820538.2021.1985145. Epub 2021 Sep 29. 42(1):73-80. doi: 10.1080/01676830.2021.1955392. Epub 2021 Jul 28.
合成参考文献
参考文献:10.2165/11539460-000000000-00000 摘要:Iskedjian M, Covert DW, Walker JH. Persistence with prostaglandin agonist use with and without adjunctive therapy for glaucoma patients: a Canadian population-based analysis. Patient. 2011;4(2):133–41. doi: 10.2165/11539460-000000000-00000. 参考文献:10.1089/jop.2011.0003 摘要:Altieri M, Ferrari E. Do Prostaglandin Analogs Affect Eyelid Position and Motility Journal of Ocular Pharmacology and Therapeutics. 2011 Oct;27(5):511–7. doi: 10.1089/jop.2011.0003. 参考文献:10.1007/s12325-011-0043-z 摘要:Scherzer M, Liehneova I, Muñoz Negrete FJ, Schnober D. Travoprost 0.004%/timolol 0.5% fixed combination in patients transitioning from fixed or unfixed bimatoprost 0.03%/timolol 0.5%. Advances in Therapy. 2011 Jul 15;28(8):661. doi: 10.1007/s12325-011-0043-z.