126690-41-3Relevant academic research and scientific papers
A practical large-scale synthesis of 17α-acetoxy-11β-(4-N,N-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-dione (CDB-2914)
Rao, Pemmaraju N.,Acosta, C. Kirk,Bahr, Martin L.,Burdett, James E.,Cessac, James W.,Morrison, Paul A.,Kim, Hyun K.
, p. 395 - 400 (2000)
A new practical synthesis of 17α-acetoxy-11β-(4-N,N-dimethylaminophenyl)-19-norpregna-4,9-diene-3,20-dione (CDB-2914) is described. The synthesis gives easily isolable solids at all steps and is amenable to large-scale process. Copyright (C) 2000 Elsevier Science Inc.
Preparing acetic acid superior strengthsi Te key intermediate of the new method
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Paragraph 0027; 0028, (2017/06/30)
The invention discloses a novel preparation method of ulipristal acetate key intermediate 3,3,20,20-double (ethylenedioxy group)-5 alpha, 17 alpha- dihydroxyl-11 bata-[4-(N,N- dimethyl amidogen)- phenyl]-19-norprogesterone-9(11)-alkene, namely 3,3- ethylenedioxy group-17 beta-cyangroup female steroid-5(10), 9(11) diene-17 alpha-alcohol is used as a raw material, through the protection of hydroxyl, the addition of Grignard reagent and cyangroup, and the protection of ketal, and the target compound is obtained finally through 1,4 addition of alpha, beta unsaturation epoxide under the catalysis of a system of cuprous halides and dimethyl sulfide. The raw materials used in the method are safe and reliable, reaction is easy to control, reaction yield and stereoselectivity are high, and the method is applicable for industrial production.
Ulipristal acetate impurities and preparation and detection method thereof
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, (2016/10/31)
The invention provides ulipristal acetate impurity compounds and a preparation method thereof, and particularly provides novel compound impurities including A (a compound A), G (a compound G), H (a compound H) and J (a compound J). The invention further provides a detection method of the impurities and application of the impurities on quality analysis of an ulipristal acetate bulk drug and a preparation thereof.
ULIPRISTAL ACETATE PREPARATION METHOD AND INTERMEDIATE THEREOF
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Paragraph 0043, (2014/09/29)
A method as well as new intermediates for preparing Ulipristal acetate (a compound I) and a method for preparing the new intermediates are provided. The intermediate in a constitutional formula IV is conductive to reacting with methyl lithium or methyl Grignard reagent, a protective group is easy to be removed after a reaction, side reactions are few, a mid-term treatment is simple, the reagents used are cheap, costs are low and the yield is high, if a compound in a constitutional formula V is obtained by the reaction of a compound in a constitutional formula III and the intermediate in the constitutional formula IV, the yield of a two-step reaction is 75%, a purity is above 98%. wherein R is defined in the specification.
INDUSTRIAL PROCESS FOR THE SYNTHESIS OF 17α-ACETOXY-11β-[4-(N,N-DIMETHYL-AMINO)- PHENYL]-19-NORPREGNA-4,9-DIENE-3,20-DIONE AND NEW INTERMEDIATES OF THE PROCESS
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Page/Page column 10; 14, (2008/06/13)
The present invention relates to a new industrial process for the synthesis of solvate- free 17α-acetoxy-11β-[4-(N,N-dimethyl-amino)-phenyl]-19-norpregna-4,9-diene-3,20-dione [CDB -2914] of formula (I) which is a strong antiprogestogene and antiglucocorticoid agent. The invention also relates to compounds of formula (VII) and (VIII) used as intermediates in the process. The process according to the invention is the following: i) 3-(ethylene-dioxy)-estra-5(10),9(11)-diene-17-one of formula (X) is reacted with potassium acetilyde formed in situ in dry tetrahydrofuran by known method, ii) the obtained 3-(ethylene-dioxy)-17α-ethynyl-17β-hydroxy-estra-5(10),9(11)-diene of formula (IX) is reacted with phenylsulfenyl chloride in dichloromethane in the presence of triethylamine and acetic acid, iii) the obtained isomeric mixture of 3-(ethylene-dioxy)-21-(phenyl-sulfinyl)-19-norpregna-5(10),9(11),17(20),20-tetraene of formula (VIII) is reacted first with sodium methoxide in methanol, then with trimethyl phosphite, iv) the obtained 3-(ethylene-dioxy)-17α-hydroxy-20-methoxy-19-norpregna-5(10),9(11),20-triene of formula (VII) is reacted with hydrogen chloride in methanol, then v) the obtained 3-(ethylene-dioxy)-17α-hydroxy-19-norpregna-5(10),9(11l)-diene-20- one of formula (VI) is reacted with ethylene glycol hi dichloromethane in the presence of trimethyl orthoformate and p-toluenesulfonic acid by known method, vi) the obtained 3,3,20,20-bis(ethylene-dioxy)-17α-hydroxy-19-norpregna- 5(10),9(11)-diene of formula (V) is reacted with hydrogen peroxide in a mixture of pyridine and dichloromethane in the presence of hexachloroacetone by known method, vii) the obtained 3,3,20,20-bis(ethylene-dioxy)-17α-hydroxy-5,10-epoxy-19-norpregn-9(11)-ene of formula (IV), containing approximately a 1:1 mixture of 5α,10α- and 5β,10β-epoxides, is isolated from the solution and reacted with a Grignard reagent obtained from 4-bromo-N,N-dimethyl-aniline in tetrahydrofuran in the presence of copper(I) chloride catalyst without separation of the isomers by known method, viii) the obtained 3,3,20,20-bis(ethylene-dioxy)-5α,17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl]-19-norpregn-9(11)-ene of formula (III) is reacted with potassium hydrogensulfate in water by known method, ix) the obtained 11β-[4-(N,N-dimethylamino)-phenyl]-17α-hydroxy-19-norpregn-4,9-diene-3,20-dione of formula (II) is acetylated with acetic anhydride in the presence of perchloric acid by known method, finally x) the solvate-free compound of formula (I) is liberated from the obtained solvate containing compound of formula (I) in a 1 : 1 mixture of ethanol and water at 70° C.
11 β-substituted progesterone analogs
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, (2008/06/13)
A 11β-aryl-19-norprogesterone steroid of the formula: STR1 wherein (i) R1 is H, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, OH, OC(O)CH3, or OC(O)R5, wherein R5 is C2-8 alkyl, C2-8 alkenyl, C2-8 alkynyl or aryl, R2 is H, R3 is H, C1-4 alkyl, C2-4 alkenyl or C2-4 alkynyl, R4 is H, CH3, F or Cl, R6 is H, (CH3)2 N, CH3 O, CH3 CO, CH3 S, CH3 SO, CH3 SO2, and X is O or NOCH3 ; or (ii) R1 and R2 taken together are a carbon-carbon bond and R3, R4, R6 and X are as defined above; or (iii) R1 and R3 taken together are --CH2 -- or --N=N--CH2 --, R2 is H and R4, R6 and X are as defined above; or (iv) R2 and R3 taken together are =CH2 and R1, R4, R6 and X are as defined above.
