- Iodine as a chemoselective reoxidant of TEMPO: application to the oxidation of alcohols to aldehydes and ketones.
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[reaction: see text] Chemoselective alcohol oxidations using catalytic TEMPO and stoichiometric iodine as the terminal oxidant were studied. Iodine was compared to other positive halogens as the terminal oxidant and shown to be superior in cases of electron-rich and heteroaromatic rings. The new conditions were successfully applied to an important intermediate (2) in the synthesis of Losartan.
- Miller, Ross A,Hoerrner, R Scott
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Read Online
- Preparation method of 2-n-butyl-4-chloro-5-formyl imidazole
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The invention discloses a preparation method of 2-n-butyl-4-chloro-5-formyl imidazole, and relates to a preparation method of 2-n-butyl-4-chloro-5-formyl imidazole. The method comprises the followingsteps: (1) cyclizing valeraldehyde and pyruvic aldehyde to obtain 2-butyl-5-methylimidazole; (2) carrying out chlorination reaction on the 2-butyl-5-methylimidazole to prepare 2-butyl-4-chloro-5-methylimidazole; and (3) carrying out an oxidation reaction on the 2-butyl-4-chloro-5-methylimidazole to obtain 2-n-butyl-4-chloro-5-formyl imidazole of which the structure is as shown in a formula I whichis described in the specification.
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Paragraph 0066-0068
(2020/09/09)
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- Production process of imidazole aldehyde
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The invention provides a production process of imidazole aldehyde. Imiline is prepared by using valeronitrile and methanol as raw materials, glycine and methanol are added to prepare imidic acid, anda further reaction is conducted with phosphorus oxychloride and DMF to obtain the imidazole aldehyde. By controlling reaction conditions and the feed ratio of the raw materials, the formation of by-products is reduced, and the yield is improved. A decoking and decolorization reaction and an activated carbon decolorization reaction are adopted, the solubility change of the imidazole aldehyde underdifferent pH conditions is used for purifying a product, and finally, the imidazole aldehyde with a purity of more than 99.2% is obtained by recrystallization.
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Paragraph 0048-0074
(2019/07/11)
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- Method for recovering and utilizing byproduct of chlorination of phosphorus pentachloride
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The invention relates to a technology for comprehensively utilizing the byproduct of chlorination of phosphorus pentachloride, and mainly relates to a post treatment, which scientifically utilizes the excess phosphorus pentachloride reagent. The byproduct is converted into an organic synthesis reagent with a wide application range. The wastes are converted into a valuable resource. The discharge of waste water, waste gas, and waste solid is reduced. The obtained reagent is an excellent active reagent, which is widely used in the chemical industry, pharmacy industry, and material industry. The production cost is reduced, and the environment is protected.
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Paragraph 0038-0039
(2017/08/28)
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- Preparation method of 2-n-butyl-4-chloro-5-formylimidazole
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The invention provides a preparation method of 2-n-butyl-4-chloro-5-formylimidazole. The preparation method comprises the following steps of using pentanimidamide hydrochloride and tert-butyl glycine hydrochloride as initial raw materials to react, so as to obtain (1-imido amyl)tert-butyl glycinate; performing deprotection, ring closing, chlorinating and vilsemier reaction, and recrystallizing, so as to obtain the 2-n-butyl-4-chloro-5-formylimidazole. The preparation method has the advantages that the price of raw materials is low, the obtaining is easy, the cost is low, the content of impurities is low, and the purity is high; the organic solvent used in the preparation process can be recycled, the pollution is little, the environment-friendly effect is realized, and the preparation method is suitable for industrialized large-scale production.
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Paragraph 0042-0050
(2017/08/31)
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- An efficient and green synthetic route to losartan
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A practical, efficient and green process for the preparation of losartan, an antihypertensive drug, has been developed with an overall yield of 58.6%. The key step is the synthesis of the two key intermediates 2-butyl-4-chloro-3H-imidazole-5-carbaldehyde (BCFI) and 2-cyano-4'-methyl biphenyl (OTBN). BCFI was synthesised from valeronitrile and acetyl chloride by three steps with an overall yield of 69%; OTBN was obtained in 86% yield by the coupling of o-chlorobenzonitrile with p-methylphenylmagnesium chloride in tetrahydrofuran in the presence of manganese chloride and chlorotrimethylsilane. The above route was successfully operated in at a pilot-plant operation.
- Shuangxia, Feng,Zheng, Gu,Yelv, Tang,Hui, Liu,Guofang, Jiang
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p. 451 - 454
(2015/11/03)
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- Preparation of 2-Substituted 4-Chloro-5-Formylimidazole and 5-Formylimidazole
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The invention relates to a preparation process for 2-substituted 5-formylimidazoles, wherein the intermediate high-pressurized synthesis of an 2-substituted 4-hydroxymethylimidazole as known in the art is conveniently avoided, and wherein much higher yields are obtained. Instead, it is proposed to prepare such 2-substituted 5-formylimidazoles via a one-pot synthesis involving 2-substituted 4-chloro-5-formylimidazole, thereby employing an additional hydrodehalogenation step. Moreover, it is found that the yield and purity of 2-substituted 4-chloro-5-formylimidazole itself can be significantly improved using a triflate catalyst in the preparation process.
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Page/Page column 4-5
(2008/12/08)
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- Process for preparing 2,4,5-trisubstituted imidazoles from N-acylated alpha-amino nitriles
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The invention is a process for preparing an imidazole of formula I which comprises treating an N-acylated α-amino nitrile with a phosphine and a carbon tetrahalide of the formula CX4, wherein X is Cl or Br, to form a haloimidazole of the formula wherein R1 is selected from the group consisting of hydrogen, C1-6alkyl, —CH2-aryl, and aryl; and R2 is selected from the group consisting of hydrogen, C1-6alkyl, —CH2—O-aryl and aryl; and X is selected from the group consisting of Cl and Br.
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- A rapid and efficient synthesis of 2-butyl-5-chloro-3H-imidazole-4- carboxaldehyde
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A rapid, efficient, cost effective procedure has been developed for the synthesis of 2-butyl-5-chloro-3H-imidazole-4-carboxaldehyde. Preparation of methyl pentanimidate was accomplished in just 12 hours, followed by a sequence of reactions without isolation and purification of the formed intermediates. The final compound was purified by simple acid-base treatment to get a product with 99.9% HPLC purity.
- Srinivas,Snehalatha Nair,Ramesh,Pardhasaradhi
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p. 506 - 508
(2007/10/03)
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- Selective Oxidation of Alcohols to Carbonyl Compounds and Carboxylic Acids with Platinum Group Metal Catalysts
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The use of platinum group metal (PGM) catalysts for the selective oxidation of various primary and secondary alcohols under mild conditions is described. High throughput screening (HTS) techniques have been used to identify trends in catalyst activity and product selectivity. Using air as oxidant and water as solvent 5% Pt, 1% Bi/C has been identified as an efficient catalyst for the transformation of 2-octanol to 2-octanone and 1-octanol to octanoic acid. To improve aldehyde selectivity the promotion of Pt/Al 2O3 and Ru/C catalysts has been investigated. The use of H2O2 as oxidant has been demonstrated as a suitable alternative to air.
- Anderson, Ross,Griffin, Ken,Johnston, Peter,Alsters, Paul L.
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p. 517 - 523
(2007/10/03)
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- Crystal structures of two imidazole derivatives
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2-n-Butyl-5-chloro-3H-imidazole-4-carbaldehyde (BCIC), C8H 11ClN2O. F.W.= 186.64, monoclinic, P21/c, a=7.2617(3)A, b= 13.2067(6)A, c=9.8491(4)A β = 101.76(1)°, V= 924.74(7)A3, Z=4, Dcal = 1.341 Mgm-3, μ = 0.367mm-1, F000=392, λ (MoKα) = 0.71073A, final R1 and wR2 are 0.049 and 0.126, respectively. 2-n-Butyl-4-chloro-1 [(2-cyanobiphenyl-4-yl)methyl]-5- hydroxymethyl imidazok (BCCI), CvfliufilNnO, F.W. = 379.88, triclinic, P 1 a = 8.198(2)A, b = 10.997(3)A, c = 11.524(2)A, α= 90.83(2)°, β= 94.31(2)°, γ = 109.45(2)°, V= 976.0(2)A3, Z=2, Dcal = 1.293Mgm-3, μ = 1.856mm-1, F000 = 400, λ (CuKα) = 1.5418A, final R1 and wR2 are 0.081 and 0.239, respectively. The imidazole ring in both the molecules is planar. The n-butyl group adopts a bent conformation in BCIC where it is in extended conformation in BCCI. The biphenyl ring system orients at an angle of 45.1(1)° in BCCI. The molecules are stabilized by N-H...N and O-H... N type hydrogen bonds in addition to van der Waals forces.
- Ambalavanan,Palani,Ponnuswamy,Thirumuruhan,Yathirajan,Prabhuswamy,Raju,Nagaraja,Mohana
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- Novel Syntheses of 2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde: A Key Intermediate for the Synthesis of the Angiotensin II Antagonist Losartan
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Reaction of glycine methyl ester (19) with imidate 18 under carefully optimized conditions allowed preparation of the rather unstable imidazolinone 11 in ca. 90% yield. Reaction of 11 with POCl3/ DMF followed by aqueous workup gave aldehyde 2, a key intermediate for the synthesis of the angiotensin II antagonist Losartan, in ca. 55% yield. Structural identification of intermediates and byproducts formed during both the reaction to prepare 11 and the reaction of 11 with POCl3/DMF allowed development of several closely related syntheses of aldehyde 2.
- Griffiths, Gareth J.,Hauck, Michael B.,Imwinkelried, Rene,Kohr, Joerg,Roten, Conrad A.,Stucky, Gerhard C.,Gosteli, Jacques
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p. 8084 - 8089
(2007/10/03)
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- Process for the preparation of formylimidazoles
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A process for the catalytic conversion of halogenated hydroxymethylimidazoles to halogenated formylimidazoles. The catalysis takes place in the presence of a peroxide. Halogenated formylimidazoles are important intermediates for pharmaceutical active ingredients.
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- Substituted imidazolyl-alkylthio-alkanoic acids
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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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- A New Regioselective Synthesis of 1,2,5-Trisubstituted 1H-Imidazoles and Its Application to the Development of Eprosartan
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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.
- Shilcrat, Susan C.,Mokhallalati, Mohamed K.,Fortunak, Joseph M. D.,Pridgen, Lendon N.
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p. 8449 - 8454
(2007/10/03)
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- Preparation of a key intermediate for the angiotensin II antagonist losartan via vilsmeier chloroformylation
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A novel preparation of 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde (1), a key intermediate for the synthesis of the angiotensin II antagonist Losartan potassium, via Vilsmeier chloroformylation of imidazolinone 3 is described.
- Griffiths, Gareth J.
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p. 283 - 284
(2007/10/03)
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- Process for the production of 2-substituted 5-chloroimidazole-4-carbaldehydes
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A process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: STR1 in which glycine is reacted with an imido ester of the general formula: STR2 and the resultant intermediate is converted into the product by a Vilsmeier reagent. The 2-substituted 5-chloroimidazole-4-carbaldehydes are valuable intermediates for the preparation of pharmaceuticals or herbicidally active compounds.
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- Process for the preparation of optionally 2-substituted 5-chloroimidazole-4-carbaldehydes
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A process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: STR1 wherein R is hydrogen, an alkyl group, an alkenyl group, a cycloalkyl group, a benzl group or a phenyl group. The imidazole compounds are important starting products for the preparation of hypotensive pharmaceuticals or herbicides.
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- Process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes
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A process for preparing 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: STR1 In the process, a glycine ester hydrohalide is ring-closed with an imidate ester to obtain the intermediate 2-substituted 3,5-dihydroimidazol-4-one. This intermediate is converted with an N,N-substituted formamide acetal into an N,N-substituted aminomethyleneimidazolinone. This latter intermediate is chlorinated with phosphorus oxychloride or phosgene to obtain the final product 2-substituted 5-chlorimidazole-4-carbaldehydes of the general formula I. Also disclosed are N,N-substituted aminomethyleneimidazolinones of the general formula: STR2 wherein R is hydrogen or is an alkyl group, an alkenyl group, a cycloalkyl group, an arylalkyl group or an aryl group, and R5 and R6 are identical or different and each is an alkyl group or an aryl group, in the form of the E- or Z-isomer.
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- Azole derivatives, process for their preparation and their use
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Azole derivatives, process for their preparation, and their useAzole derivatives of the formula (I) STR1 in which A, L, O, R 1, X, Y, Z and q have the meanings given, process for their preparation, pharmaceutical preparations and the use of the compounds are described. Azole derivatives of the formula I where the symbols have for example the following meanings:R 1 is (C 2 -C 10)-alkyl,Z is nitrogen,X and Y are independently of one another CR 2,L is --CH 2 --,q is zero or 1,A is a biphenyl radical which is substituted for example by R 15,R 2 is halogen or hydrogen,R 15 is SO 2 --NH--CO--OR 6 andR 6 is phenyl,are highly active antagonists of angiotensin II receptors.
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- 2-substituted 5-chlorimidazoles
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The 2-substituted 5-chlorimidazoles of general formula: STR1 are new intermediate products for the production of antihypertensive pharmaceutical agents or of herbicidal compounds. A process for the production of these intermediate products as well as a new process for the further reaction of 2-substituted 5-chlorimidazoles of general formula I, wherein R1 is hydrogen, to the 2-substituted 5-chlorimidazole-4-carbaldehydes of general formula: STR2
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- Process for the production of 2-substituted 5-chlorimidazole-4-carbaldehydes
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A process for the production of 2-substituted 5-chlorimidazole-4-carbaldehydes of the general formula: STR1 wherein R is hydrogen, an alkyl group, and alkenyl group, a cycloalkyl group, a benzyl group, a phenyl group or an aryl group. These compounds form important intermediate products for the production of antihypertensive pharmaceutical agents or herbicidal compounds.
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- Process for the production of 2-substituted-5-chlorimidazole-4-carbaldehydes
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Process for the production of 2-substituted 5-chlorimidazole-4-carbaldehydes of general formula: STR1 wherein R is alkyl, cycloalkyl, benzyl, or phenyl. These compounds form valuable intermediate products for the production of antihypertensive pharmaceutical agents or herbicidal compounds.
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- N-SUBSTITUTED IMIDAZOLE AND BENZIMIDAZOLE DERIVATIVES USEFUL AS ANGIOTENSON II ANTAGONISTS
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Compounds are disclosed having the formula STR1 These compounds inhibit the action of angiotensin II and are useful, therefore, for example, as antihypertensive agents.
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- Substituted imidazoles, pharmaceutical compositions containing these, and the use thereof as antagonists of angiotensin II receptors for the treatment of high blood pressure
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The invention relates to compounds of the formula I STR1 in which X, Y and Z are identical or different and are N or CR 2, R 1 and R 2 are as defined in the description, L is an alkylene radical, q is 0 or 1, and A is the radical of a fused heterobicyclic compound. The invention furthermore relates to a process for preparing the said compounds, agents containing these, and the use thereof in the treatment of high blood pressure.
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- IMIDAZOLE WITH ANGIOTENSIN II ANTAGONIST PROPERTIES
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This invention relates to novel substituted imidazole and triazole derivatives which antagonize the binding of angiotensin II to its receptors. The compounds are useful in the treatment of hypertension, heart failure, glaucoma, and hyperaldosteronism. Methods of making the compounds, novel intermediates useful in the preparation of the compounds, pharmaceutical compositions containing the compounds, and methods of using them are also covered.
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- Method of producing formylimidazoles
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In producing formylimidazoles by catalytically oxidizing the corresponding 4- or 5-hydroxymethylimidazoles, the catalytic oxidation is carried out in the presence of a noble metal catalyst while oxygen or air is blown into the reaction system. In this case, it is particularly desirable that the catalytic oxidation in the presence of a noble metal catalyst be carried out in a solvent comprising an aqueous alkali or in a mixed solvent composed of an aqueous alkali and an organic solvent immiscible with water.
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- QUINOLINE DERIVATIVES, PROCESS FOR THEIR PREPARATION, AND THEIR THERAPEUTIC APPLICATIONS
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The present invention provides a compound which is a quinoline derivative of the formula (I) STR1 in which R 1 represents either 1H-tetrazol-5-yl, or CO 2 H,R 2 represents either (C 1-7) alkyl or (C 2-6)alkenyl,R 3 and R 4 represent, independently of each other, hydrogen, halogen, cyano group, (C 1-7) alkyl, (C 3-7)cycloalkyl(C 1-4)alkyl, aryl, aryl(C 1-4)alkyl, aryl(C 2-6)alkenyl,--(CH 2) m--COR 5 in which m=0 to 4 and R 5 represents hydrogen,--OH,--(C. sub.1-6)alkoxy, or--NR 7 R. sub.8, R 7 and R 8 representing, independently of each other, hydrogen or--(C 1-4)alkyl group, or a--(CH 2) n--R 6 group in which n=1 to 4 and R 6 represents--OH,--(C 1-6)alkoxy,--(C 1-4) alkoxy--(C 1-4) alkoxy, or (C. sub.3-7)cycloalkyl(C 1-4)alkoxy group, or a pharmaceutically acceptable salt thereof and their therapeutic applications.
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- Indole- and benzimidazole-substituted imidazole and benzimidazole derivatives
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Novel compounds are disclosed having the formula STR1 wherein X, R1, R2, R3, R4, and R5 are substituents. These compounds inhibit the action of angiotensin II and are useful, therefore, for example, as antihypertensive agents.
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- IMIDAZOLE DERIVATIVES BEARING ACIDIC FUNCTIONAL GROUPS AT THE 5-POSITION, THEIR COMPOSITIONS AND METHODS OF USE AS ANGIOTENSIN II ANTAGONISTS
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There are disclosed substituted imidazole derivatives of Formula I bearing acidic functional groups which are useful as angiotensin II antagonists. STR1
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- BENZOXAZOLE AND RELATED HETEROCYCLIC SUBSTITUTED IMIDAZOLE AND BENZIMIDAZOLE DERIVATIVES
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Novel compounds are disclosed having the formula STR1 wherein X, Y, R 1, R 2, R 3, R 4, and R 5 are as defined herein. These compounds inhibit the action of angiotensin II and are useful, therefore, for example, as antihypertensive agents.
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- Imidazole and benzimidazole derivatives
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Novel angiotensin-II receptor antagonists are disclosed having the general formula STR1 wherein R 1, R 2, R 3, R 4, R 5, W and X are as defined herein.
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- A convenient synthesis of 2-butyl-4(5)-chloro-1H-imidazole-5(4)-carboxaldehyde
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A convenient synthesis of 2-butyl-4(5)-chloro-1H-imidazole-5(4)-carboxaldehyde, starting from 2-butyl imidazole, has been developed.
- Watson
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p. 2971 - 2977
(2007/10/02)
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- ANGIOTENSIN II RECEPTOR BLOCKING IMIDAZOLES
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Substituted imidazoles such as STR1 are useful as angiotensin II blockers. These compounds have activity in treating hypertension and congestive heart failure.
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- Treatment of congestive heart failure with angiotensin 11 receptor blocking imidazoles
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Substituted imidazoles such as STR1 are useful as angiotensin II blockers. These compounds have activity in treating hypertension and congestive heart failure.
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- Nonpeptide Angiotensin II Receptor Antagonists: The Discovery of a Series of N-(Biphenylylmethyl)imidazoles as Potent, Orally Active Antihypertensives
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A new series of nonpeptide angiotensin II (AII) receptor antagonists has been prepared.These N-(biphenylylmethyl)imidazoles, e.g. 2-butyl-1--4-chloro-5-(hydroxymethyl)imidazole, differ from the previously reported N-(benzamidobenzyl)imidazoles and related compounds in that they produce a potent antihypertensive effect upon oral administration; the earlier series generally were active only when administered intravenously.It has been found that the acidic group at the 2'-position of the biphenyl is essential.Only ortho-substituted acids possess both high affinity for the AII receptor and good oral antihypertensive potency.The carboxylic acid group has been replaced with a variety of acidic isosteres, and the tetrazole ring has been found to be the most effective.The tetrazole derivative, DuP 753, is currently in development for the treatment of hypertension.
- Carini, David J.,Duncia, John V.,Aldrich, Paul E.,Chiu, Andrew T.,Johnson, Alexander L.,et al.
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p. 2525 - 2547
(2007/10/02)
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