- Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)
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The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.
- Condon, Sylvie,Le Gall, Erwan,Pichon, Christophe,Presset, Marc,Xavier, Tania
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p. 2085 - 2094
(2021/09/02)
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- Synthesis and biological evaluation of [carboxyl-11C]eprosartan
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Essential hypertension occurs in approximately 25% of the adult population and one cause of hypertension is primary aldosteronism. Targeting the angiotensin II AT1 receptor using PET and an appropriate tracer may offer a diagnostic method for a
- Aberg, Ola,Lindhe, Oerjan,Hall, Hakan,Hellman, Per,Kihlberg, Tor,Langstroem, Bengt
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experimental part
p. 295 - 303
(2010/08/06)
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- 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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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
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Page/Page column 13
(2009/08/14)
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- IMPROVED PROCESS FOR EPROSARTAN
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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
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Page/Page column 8
(2008/12/06)
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- Potent Nonpeptide Angiotensin II Receptor Antagonists. 2. (1-Carboxybenzyl)imidazole-5-acrylic Acids
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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.
- Keenan, Richard M.,Weinstock, Joseph,Finkelstein, Joseph A.,Franz, Robert G.,Gaitanopoulos, Dimitri E.,et al.
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p. 1880 - 1892
(2007/10/02)
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- Imidazolyl-alkenoic acids useful as angiotensin II receptor antagonists
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Angiotensin II receptor antagonists having the formula: STR1 which are useful in regulating hypertension and in the treatment of congestive heart failure, renal failure, and glaucoma, pharmaceutical compositions including these antagonists, and methods of using these compounds to produce angiotensin II receptor antagonism in mammals.
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