82789-26-2Relevant academic research and scientific papers
Preparation method of tadalafil intermediate
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Paragraph 0037; 0039; 0042-0044; 0047-0049; 0052-0054; 0057, (2020/05/30)
The invention discloses a preparation method of a tadalafil intermediate, which comprises: S1, carrying out a reaction on piperonyl alcohol, oxygen and a catalyst in an organic solvent, washing with ahydrochloric acid aqueous solution, and removing the aqueous phase by layering to obtain a piperonal solution; s2, adding D-tryptophan and trifluoroacetic acid into the piperonal solution, reacting in an inert gas atmosphere, then washing with an alkaline aqueous solution, and removing an aqueous phase by layering to obtain an intermediate solution; s3, taking the intermediate solution, evaporating to remove the organic solvent, adding an inorganic acid and water, continuously reacting in an inert gas atmosphere, and purifying to obtain the tadalafil intermediate. According to the method, thepiperonyl alcohol is used as a starting material, so that the use of a controlled easily-prepared drug piperonal raw material is avoided; no organic solvent is needed in the configuration conversionprocess, a single-configuration product is directly obtained, reaction conditions of all steps are mild, operation is easy, the method is suitable for industrial production, and the prepared tadalafilintermediate is good in purity and low in isomer content.
Method for synthesizing tadalafil
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Paragraph 0011; 0016, (2019/10/02)
The invention discloses a method for synthesizing tadalafil. Tadalafil is synthesized from D-tryptophan and a compound of formula 1. The method for preparing tadalafil of the invention can effectivelyprepare tadalafil. In addition, the starting material piperonyl dimethyl acetal of the preparation method is easy to obtain as a non-controlled material, the procurement and management are not restricted, the use of the controlled material piperonyl is effectively avoided, the management and procurement are convenient, the process steps are short, the production cost is greatly reduced, and the preparation method is more suitable for large-scale and industrial production of tadalafil.
Impurity reference substance of tadalafil and preparation method of impurity reference substance
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Paragraph 0075; 0076; 0077; 0078; 0079, (2017/04/14)
The invention relates to an impurity reference substance of tadalafil and a preparation method of the impurity reference substance. The invention discloses compounds represented by formulae I and II shown in the description, wherein R1 is selected from halogen or NR2R3; and R2 and R2 are respectively independently selected from H or C1-C4 alkyl. The invention further discloses a preparation method of the compounds. Compounds M2Z1, M2Z2, Z1 and Z2 have high purities and can be used as reference substances for detecting or monitoring the impurity content and the product quality of non-bulk drugs and intermediates of tadalafil, so that the medication safety of tadalafil is guaranteed; furthermore, the preparation method of the impurity reference substance is simple and convenient, the operation and the control are simple, the energy consumption is low, the consumed time is short, the production efficiency is high, the cost is low, and the economic value is obvious; and the impurity reference substance has a very good industrial prospect.
Β-Carboline alkaloid derivative, its preparation process and its medical use
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Paragraph 0107; 0196; 0198; 0199, (2016/10/10)
The invention provides beta-carboline alkaloid derivatives and pharmaceutically acceptable salts thereof, their preparation method, a pharmaceutical composition containing the beta-carboline alkaloid derivatives, and a medical use of the beta-carboline al
Microwave-Assisted Synthesis of Tetrahydro-β-carbolines and β-Carbolines
Eagon, Scott,Anderson, Marc O.
, p. 1653 - 1665 (2015/10/05)
A microwave-mediated Pictet-Spengler procedure utilizing 1,2-dichloroethane (DCE) and trifluoroacetic acid (TFA) was developed to provide tetrahydro-β-carboline salts in high yields. Reactions are complete in 20 minutes or less and the product precipitates from solution in high yields and purity, negating the need for liquid-liquid extraction or column chromatography. This method tolerates a wide range of functionality and can be performed on milligram to gram scales. A subsequent microwave-mediated aromatization of the synthesized tetrahydro-β-carbolines to β-carbolines was also developed utilizing catalytic Pd/C. The aromatization is complete in 60 min or less with most substrates requiring minimal purification. A microwave-assisted Pictet-Spengler procedure was developed to afford tetrahydro-β-carboline salts in high yields with no liquid-liquid extraction or chromatography required. A subsequent microwave-assisted aromatization procedure was also developed to provide β-carbolines in high yields requiring limited purification.
PROCESS FOR THE PREPARATION OF 2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLIN-3-CARBOXYLIC ACID ESTERS"
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Page/Page column 8-9, (2009/10/18)
The present invention relates to the process of preparation of 2,3,4,9-tetrahydro- 1 /-/-β-carbolin-3-carboxylic acid esters substituted in position 1 of the general formula (I). in the preferred diastereoisomeric form through a single step starting from tryptophan in racemic form and/or its enantiomers and from 3,4-(methylenedioxy)benzaldehyde.
Alternative synthesis of tadalafil: PDE5 inhibitor
Anumula, Raghupathi Reddy,Madivada, Lokeswara Rao,Gilla, Goverdhan,Raju, V. V. N. K. Prasad,Kagga, Mukkanti,Reddy, Padi Pratap,Bhattacharya, Apurba,Bandichhor, Rakeshwar
experimental part, p. 4265 - 4271 (2009/04/11)
Two-step alternative synthesis of tadalafil (1) is described. The synthesis features Pictet-Spengeler type reaction and DCC (N,N′- dicyclohexylcarbodiimide)/HOBt (N-hydroxybenzotriazole)-mediated double amidation employing sarcosine ethyl ester hydrochlor
Chemical compounds
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Page/Page column 11; 12, (2008/06/13)
Compounds of the general structural formula and use of the compounds and salts and solvates thereof, as therapeutic agents.
