133040-02-5Relevant articles and documents
Eprosartan intermediate of a kind of improved process for preparing aryl imidazole aldehyde
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Paragraph 0024; 0027-0029; 0032-0034; 0037-0044, (2019/02/02)
The invention discloses an improved process for preparing aryl imidazole aldehyde serving as an eprosartan intermediate. The process comprises the following steps of: performing methyl esterification reaction on parachloro-methylbenzoic acid to obtain parachloro-methyl benzoate; reacting the parachloro-methyl benzoate and imidazole aldehyde under agitation by taking dimethyl formamide (DMF) as a reaction solvent and potassium carbonate as an alkali at the temperature of between 20 and 40 DEG C; after reaction, filtering to remove the potassium carbonate; adding water into filtrate under agitation for crystallizing; and recovering the aryl imidazole aldehyde serving as the eprosartan intermediate. The process has the advantages of high yield, high purity of products, relatively low content of N-heterogeneous impurities, extremely low content of dimeric impurities and the like, can be used in the next process without refining, and is suitable for large-scale industrial production.
IMPROVED PROCESS FOR MANUFACTURING ANHYDROUS (E)-3-[2-BUTYL-1- {(4-CARBOXYPHENYL) METHYL}-1H-IMIDAZOLE-5-YL]-(THIOPHEN-2- YLMETHYL)PROP-2-ENOIC ACID METHANE SULFONATE
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Page/Page column 7; 11, (2009/08/14)
The present invention relates to a simple efficient and cost effective process for commercial manufacture of (E)-3-[2-Butyl-1-{(4-carboxyphenyl) methyl}-1H-imidazole-5-yl]- 2-(thiophen-2-ylmethyl)prop-2-enoic acid and its conversion to substantially pure
IMPROVED PROCESS FOR EPROSARTAN
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Page/Page column 6, (2008/12/06)
The present invention provides an improved and commercially viable process for preparation of eprosartan and its pharmaceutically acceptable acid addition salts thereof in high purity and in high yield. Thus, for example, methyl 4-[[2-butyl-5-formyl-1 H-i
A New Regioselective Synthesis of 1,2,5-Trisubstituted 1H-Imidazoles and Its Application to the Development of Eprosartan
Shilcrat, Susan C.,Mokhallalati, Mohamed K.,Fortunak, Joseph M. D.,Pridgen, Lendon N.
, p. 8449 - 8454 (2007/10/03)
A new method is presented for the preparation of 1,2-disubstitued-1H-imidazole-5-carboxaldehydes by the reaction of N-monosubstituted amidines with 2-halo-3-alkoxy-2-propenals. The reaction is highly regioselective with ratios of 1,2,5:1,2,4-imidazolecarboxaldehydes ranging from 85:15 to 100: 0. This methodology could be extended with similar results to the synthesis of imidazole-5-nitriles by the reaction of 2-bromo-3-methoxy-2-propenenitrile with N-monosubstituted amidines.
SUBSTITUTED-5-METHYLIDENE HYDANTOINS WITH AT1 RECEPTOR ANTAGONIST PROPERTIES
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, (2008/06/13)
Substituted 1-benzylimidazole-5-methylidene hydantoins are disclosed as well as methods of preparing them, pharmaceutical compositions containing them, and method of using them. Intermediates useful in the preparation of the compounds of the invention are also disclosed and synthetic methods for preparing the novel intermediates. The compounds are useful as antagonists of angiotensin II and thus are useful in the control of hypertension, hyperaldosteronism, congestive heart failure, surgically induced vascular smooth muscle proliferation, and glaucoma.
Potent Nonpeptide Angiotensin II Receptor Antagonists. 2. (1-Carboxybenzyl)imidazole-5-acrylic Acids
Keenan, Richard M.,Weinstock, Joseph,Finkelstein, Joseph A.,Franz, Robert G.,Gaitanopoulos, Dimitri E.,et al.
, p. 1880 - 1892 (2007/10/02)
The further evolution of the imidazole-5-acrylic acid series of nonpeptide angiotensin II receptor antagonists is detailed (for Part 1, see: J.Med.Chem. 1992, 35, 3858).Modifications of the N-benzyl ring substitution were undertaken in an effort to mimic the Tyr4 residue of angiotensin II.Introduction of a p-carboxylic acid on the N-benzyl ring resulted in the discovery of compounds with nanomolar affinity for the receptor and good oral activity.SAR studies of these potent antagonists revealed that the thienyl ring, the (E)-acrylic acid, and the imidazole ring in addition to the two acid groups were important for high potency.Also, overlay comparisons of the parent diacid with both angiotensin II and a representative biphenylyltetrazole nonpeptide angiotensin II receptor antagonist are presented.The parent diacid analog, SKF 108566 or (E)-3--2-propenoic acid, is currently in clinical development for the treatment of hypertension.