- Method for preparing high-purity ribavirin intermediate by one-pot method (by machine translation)
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The invention relates to the technical field of chemical medicine, in particular to a method for preparing a high-purity ribavirin intermediate by a one-pot method. The method comprises the following steps: (1) replacing the compound I with the compound II to obtain the reaction liquid of the compound III. (2) Acrylamide was added to III reaction liquid of the compound, and the reaction liquid of compound IV was obtained under Heck reaction conditions. (3) In the reaction solution of Compound IV, activated carbon is first added for decolorization treatment, and then a poor solvent is added for crystallization to obtain a white compound IV, i.e. a ripe intermediate. The method for preparing the high-purity ribavirin intermediate by one-pot method is scientific, reasonable, simple and feasible, improves product purity and yield, and is suitable for large-scale production. (by machine translation)
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- A METHOD OF PRODUCING HIGHLY PURE RILPIVIRINE AND ITS SALTS
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A method of preparing Rilpivirine of formula I, or a suitable salt thereof, comprising a reaction of a hydrogen halide of the aniline derivative of formula II with chloropyrimidine of formula III in methyl isobutyl ketone and in the presence of a polar additive.
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Page/Page column 4; 5
(2016/08/17)
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- Method for effectively removing isomer of rilpivirine
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The invention belongs to the field of chemical synthesis of medicines, and in particular discloses a method for effectively removing the isomer of rilpivirine. The method comprises the following steps: synthesizing organic acid salts of rilpivirine from rilpivirine and maleic acid, benzene sulfonic acid, p-methylbenzene sulfonic acid, oxalic acid, tartaric acid, succinic acid, citric acid and the like, performing recrystallization on the organic acid salts of the rilpivirine by using mixed solvents of methanol, ethanol, acetonitrile, acetic acid, N,N-dimethyl formamide and the like and water, furthermore freeing recrystallized organic acid salts of the rilpivirine by using alkali such as sodium hydroxide, lithium hydroxide, sodium bicarbonate, sodium carbonate, potassium carbonate, triethylamine, potassium tert-butoxide and sodium ethoxide, thereby reducing the content of Z-isomer of rilpivirine to be 0.1% or below from about 12%. The method is simple and convenient to operate, gentle in reaction conditions, low in production cost, relatively small in loss of products in the purification process, good in reproducibility, stable in process, applicable to industrial amplification and great in practical values, and the content of the Z-isomer of the rilpivirine can be reduced to be 0.1% or below from 12-14% at a time.
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Paragraph 0047; 0048
(2017/01/23)
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- Pharmaceutical compositions comprising a basic drug compound, a surfactant, and a physiologically tolerable water soluble acid
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The invention provides a novel pharmaceutical composition comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base characterized in that the acid respectively base:drug compound ratio is at least 1:1 by weight.
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Page/Page column 73-74
(2015/12/04)
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- RILPIVIRINE HYDROCHLORIDE
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The present invention provides a novel process for the preparation of rilpivirine. The present invention also provides a novel process for the preparation of rilpivirine hydrochloride. The present invention further provides a rilpivirine hydrochloride monohydrate, process for its preparation and pharmaceutical compositions comprising it.
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Paragraph 0091
(2014/12/09)
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- PROCESS FOR RILPIVIRINE USING NOVEL INTERMEDIATE
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The present invention provides a commercially viable process for preparing rilpivirine and its pharmaceutically acceptable acid addition salts thereof in high yields using novel intermediate.
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Page/Page column 10
(2014/02/15)
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- PROCESS FOR RILPIVIRINE
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The present invention provides a novel process for the preparation of 4-(4-hydroxypyrimidin-2-ylamino)benzonitrile. The present invention also provides a novel process for the preparation of 4-iodo-2,6-dimethyl benzenamine. The present invention further provides an improved process for the preparation of rilpivirine. The present invention further provides a tosylate salt of rilpivirine, process for its preparation and pharmaceutical compositions comprising it.
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Paragraph 0088-0089
(2014/08/19)
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- IMPROVED PROCESS FOR PREPARATION OF RILPIVIRINE AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF
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Disclosed is an improved process for the preparation of rilpivirine hydrochloride. The process comprises a) reacting 3-(4-amino-3,5-dimethyl phenyl)-acrylonitrile hydrochloride and 4-[(4-chloropyrimidin-2-yl) amino] benzonitrile in the presence of a phase transfer catalyst followed by saltification with an acid and b) converting the rilpivirine acid addition salt into rilpivirine hydrochloride salt.
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Page/Page column 21; 22
(2014/01/07)
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- RILPIVIRINE HYDROCHLORIDE
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As used herein the term "room temperature" refers to a temperature of about 25°C to about 35°C. According to one aspect of the present invention, there IS provided a novel process for the preparation of rilpivirine, which comprises: a) condensing the (E)-3-( 4-amino-3,5-dimethylphenyl)acrylonitrile hydrochloride with 4-( 4-chloropyrimidin-2-ylamino )benzonitrile m the presence of Nmethylpyrrolidone; b) heating the contents obtained in step (a) at about 75 to 95°C to obtain a solution; c) cooling the solution obtained in step (b) at below 35°C; d) adding water to the reaction mass; and e) isolating rilpivirine. The reaction in step (b) may preferably be heated to 100 to 110°C. Step (c) may preferably be carried out at room temperature. Rilpivirine may be isolated in step (e) by the methods known such as Filtration or centrifugation.
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Page/Page column 10
(2013/03/28)
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- PROCESS FOR RILPIVIRINE
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The present invention provides a novel process for the preparation of 4-(4-hydroxypyrimidin-2-ylamino)benzonitrile. The present invention also provides a novel process for the preparation of 4-iodo-2,6-dimethyl benzenamine. The present invention further provides an improved process for the preparation of rilpivirine. The present invention further provides a tosylate salt of rilpivirine, process for its preparation and pharmaceutical compositions comprising it.
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Page/Page column 11
(2012/11/13)
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- SOLID STATE FORMS OF RILPIVIRINE BASE, AND RILIPIVIRINE SALTS
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The present invention provides solid state forms of Rilpivirine base, salts of Rilpivirine, solid state forms of Rilpivirine salts, and processes for preparing the solid state forms. The invention also provides pharmaceutical compositions thereof.
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Page/Page column 25-26
(2012/10/07)
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- Synthesis of novel diarylpyrimidine analogues and their antiviral activity against human immunodeficiency virus type 1
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This paper reports the synthesis and the antiviral properties of new diarylpyrimidine (DAPY) compounds as nonnucleoside reverse transcriptase inhibitors (NNRTIs). The synthesis program around this new DAPY series was further optimized to produce compounds displaying improved activity against a panel of eight clinically relevant single and double mutant strains of human immunodeficiency virus type 1 (HIV-1).
- Guillemont, Jerome,Pasquier, Elisabeth,Palandjian, Patrice,Vernier, Daniel,Gaurrand, Sandrine,Lewi, Paul J.,Heeres, Jan,De Jonge, Marc R.,Koymans, Lucien M. H.,Daeyaert, Frits F. D.,Vinkers, Maarten H.,Arnold, Eddy,Das, Kalyan,Pauwels, Rudi,Andries, Koen,De Béthune, Marie-Pierre,Bettens, Eva,Hertogs, Kurt,Wigerinck, Piet,Timmerman, Philip,Janssen, Paul A. J.
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p. 2072 - 2079
(2007/10/03)
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- PROCESSES FOR THE PREPARATION OF 4-[[4-[[4-(2-CYANOETHENYL)-2,6-DIMETHYLPHENYL]AMINO]-2-PYRIMIDINYL]AMINO]BENZONITRILE
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Processes for the preparation of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile of formula (I), a N-oxide, a pharmaceutically acceptable acid addition salt, a quaternary amine or a stereochemically isomeric form thereof are provided, said processes comprise a) reacting 4-(2-cyanoethenyl)-2,6-dimethylbenzenamine with an intermediate of formula (III) in the presence of a suitable solvent; b) reacting an intermediate of formula (IV) with acrylonitrile in the presence of a suitable palladium catalyst, a suitable base and a suitable solvent; c) dehydrating the corresponding amide of the compound of formula (I).
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