133690-92-3Relevant articles and documents
New technology for preparing azilsartan
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Paragraph 0020; 0021, (2017/11/29)
The invention relates to a preparation method for azilsartan. The method is characterized by comprising the following steps: enabling 2-fluorine-3-bromine nitrobenzene to react with a midbody 3 prepared from suzuki reaction, replacing 2 fluorines and then reducing by nitro group; reacting with tetraethyl orthocarbonate, closing the ring and forming a benzimidazole ring; reacting with hydroxylamine hydrochloride and compounding a phenyl substituted oxadiazole ring under the effect of CDI; forming formic acid with carbon dioxide under the catalysis of n-butyllithium, thereby acquiring the product. The preparation method has the advantages of easily acquired raw materials, simple process, high overall yield, few side products, simplicity in post-processing and suitability for industrial production.
Anti-Inflammation Compounds
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Paragraph 0118; 0128, (2014/06/23)
The present invention refers to: a compound having the general formula (I), wherein n is 0, 1, 2 or; m is 0, 1, 2 or 3; o is 0, 1, 2 or 3; W, X, Y and Z are independently selected from CH, N or N-oxide; A is NR4, C═O, C═S, OP(O)(O), P═O, CH2, or a heteroarly selected from the group consisting of (a), (b), (c), (d), (e), (f), (g); V is C═O, O, S, CH2, or NR5; as well as its use in treating inflammatory diseases such as asthma, COPD, inflammation post infection, arthritis, atherosclerosis, pain and dermatitis.
Sequential one-pot access to molecular diversity through aniline aqueous borylation
Erb, William,Albini, Mathieu,Rouden, Jacques,Blanchet, Jrme
, p. 10568 - 10580 (2015/01/08)
On the basis of our recently reported aniline aqueous borylation, molecular diversity was achieved in a one-pot process by combining other reactions such as esterification, Suzuki-Miyaura coupling, hydrogenolysis, or Petasis borono-Mannich.
Improved methods for the synthesis of irbesartan, an antihypertensive active pharmaceutical ingredient
Rao, Korrapati V. V. Prasada,Dandala, Ramesh,Handa, Vijay K.,Rao, Inti V. Subramanyeswara,Rani, Ananta,Naidu, Andra
, p. 2897 - 2905 (2008/02/13)
New methods for the preparation of irbesartan 1 have been described. The dehydration and tetrazole formation in one step from substituted cyclopentane derivative 7 with tributyltin chloride and sodium azide is described. Selective hydrolysis of nitrile 3 with HCl has also been described in the preparation of N-acylaminocyclopentane-2-carboxylic acid 4, which is the key intermediate for the preparation of irbesartan. The impurity profiling of irbesartan has also been discussed. Copyright Taylor & Francis Group, LLC.
AN IMPROVED PROCESS FOR THE PREPARATION OF IRBESARTAN
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Page/Page column 14-15, (2008/06/13)
The present invention relates to an improved process for the preparation of 2-n-butyl-3-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]-1,3-diazaspiro[4.4]non-1-en-4-one (Irbesartan)
SUBSTITUTED 1,2,4-TRIAZOLES BEARING ACIDIC FUNCTIONAL GROUPS AS ANGIOTENSIN II ANTAGONISTS
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, (2008/06/13)
Novel substituted triazolinone, triazolinethione, and triazolinimine compounds of the formula I are useful as angiotensin II antagonists. STR1
SUBSTITUTED TRIAZOLES AS ANGIOTENSIN II ANTAGONISTS
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, (2008/06/13)
Novel substituted triazoles of the formula (I), which are useful as angiotensin II antagonists, are disclosed. STR1
Nonpeptide angiotensin II antagonists derived from 4H-1,2,4-triazoles and 3H-imidazo[1,2-b][1,2,4]triazoles
Ashton,Cantone,Chang,Hutchins,Strelitz,MacCoss,Chang,Lotti,Faust,Chen,Bunting,Schorn,Kivlighn,Siegl
, p. 591 - 609 (2007/10/02)
By a variety of synthetic routes, we have synthesized a series of 3,4,5- trisubstituted 4H-1,2,4-triazoles and a related series of 3H-imidazo[1,2- b][1,2,4]triazoles and evaluated them in vitro and in vivo as angiotensin II (AII) antagonists. Principal efforts focused on triazoles bearing an n-alkyl substituent at C3 and a 4-[(2-carboxybenzoyl)amino]benzyl, (2'- carboxybiphenyl-4-yl)methyl, or [2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl side chain at N4. Among numerous variations at C5, benzylthio groups gave the best potency. Particularly noteworthy was 3-n-butyl-5-[(2- carboxybenzyl)thio]-4-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-4H-1,2,4- triazole (71, IC50 1.4 nM), which blocked the AII pressor response in conscious rats at 0.3 mg/kg iv with a duration of action of approximately 6 h, similar to that of DuP 753. Although 71 was active orally only at a 10- fold higher dose level, good oral bioavailability was demonstrated for a monoacidic analogue 62. Most potent among the bicyclic derivatives was 2-n- butyl-5,6-dimethyl-3-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-3H- imidazo[1,2-b][1,2,4]triazole (93, IC50 7.8 nM). The effects of hydrophobic, hydrogen-bonding, and ionic interactions with the AT1 receptor are considered.
Triazolinones as Nonpeptide Angiotensin II Antagonists. 1. Synthesis and Evaluation of Potent 2,4,5-Trisubstituted Triazolinones
Chang, Linda L.,Ashton, Wallace T.,Flanagan, Kelly L.,Strelitz, Robert A.,MacCoss, Malcolm,et al.
, p. 2558 - 2568 (2007/10/02)
A series of 2,4-dihydro-2,4,5-trisubstituted-3H-1,2,4-triazol-3-ones was prepared via several synthetic routes and evaluated as AII receptor antagonists in vitro and in vivo.The preferred compounds contained a methyl side chain at N4 and an n-butyl group at C5.A number of these bearing an alkyl or aralkyl substituent at N2 showed in vitro potency in the nanomolar range (rabbit aorta membrane receptor), and several of these, e.g., the 2,2-dimethyl-1-propyl analogue (54, IC50 = 2.1 nM), effectively blocked the AII pressor response in conscious rats with significant duration (2.5 h at 1 mg/kg orally for 54).Among analogues possessing aryl substituents at N2, ortho substitution on the phenyl moiety resulted in several derivatives with in vitro potency in the low nanomolar range.One of these, featuring a 2-(trifluoromethyl)phenyl substituent at N2 (25, IC50 = 1.2 nM), was effective at 1 mg/kg orally in the rat model, with a duration of >6 h.Implications for hydrophobic and hydrogen-bonding interactions with the AT1 receptor are discussed.
