- Reduction of aldehydes and oximes to their corresponding alcohols and amines by catalytic hydrogenation method
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The reduction of aldehydes such as 2-butyl-5-chloro-3H-imidazole-5- carbaldehyde and veratraldehyde, which are pharmaceutical key intermediates, have been reduced to alcohols by catalytic hydrogenation method in the presence of magnesium and also oximes are reduced to primary amines successively by magnesium/ammonium formate system, is a large scale feasible and cheaper method. The crystal structure of the product, (2-butyl-5-chloro-3H-imidazole-4-yl)- methanol 1 is reported.
- Basappa,Doreswamy,Mahendra,Mantelingu,Sridhar,Prasad, J. Shashidhara,Rangappa
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p. 148 - 151
(2007/10/03)
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- New method for the synthesis of diversely functionalized imidazoles from N-acylated α-aminonitriles
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(Equation presented) A new general method for the synthesis of medicinally important diversely functionalized imidazoles from N-acylated α-aminonitriles has been developed. N-Acylated α-aminonitriles were reacted with triphenylphosphine and carbon tetrahalide to afford 2,4-disubstituted 5-halo-1H-imidazoles in good yield. This new methodology was applied for the synthesis of 2-butyl-4-chloro-5-hydroxymethylimidazole. These halo-imidazoles can be directly converted to 2,4,5-trisubstituted imidazoles through palladium-catalyzed coupling reactions.
- Zhong, Yong-Li,Lee, Jaemoon,Reamer, Robert A.,Askin, David
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p. 929 - 931
(2007/10/03)
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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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- 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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- 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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- Process for synthesizing 4-halo-5-(hydroxymethyl) imidazole compounds
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A process for preparing, on an industrial scale, 4-halo-5-(hydroxymethyl) imidazole compounds that are useful as intermediates for medicines. A 4-chloro-5-(hydroxymethyl) imidazole compound, a 4-bromo-5-(hydroxymethyl) imidazole compound or a like compound is synthesized by reacting a 4,5-bis(hydroxymethyl) imidazole compound with a halogenating agent such as an N-chlorosuccinimide, an N-bromosuccinimide, a chlorinated isocyanuric acid compound or the like compound.
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- N-(heteroaryl) imidazolyl-alkenoic acids having angiotension II receptor antagonist activity
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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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- Method for purification of 2-alkyl-4-halo-5-formylimidazoles
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The invention provides a method of purifying 2-alkyl-4-halo-5-formylimidazoles, which comprises dissolving an 2-alkyl-4-halo-5-formylimidazole in an aqueous solution of a sulfonating agent, adjusting the solution to pH 1-6, and removing the impurity 2-alkyl-4,5-dihaloimidazole by filtration or extraction.
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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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- PREPARATION OF A MODEL SYSTEM FOR A CONSTRAINED ANGIOTENSIN II RECEPTOR ANTAGONIST
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An imidazooxazin-8-one system, designed to be a fused ring analog of a potent angiotensin II receptor antagonist, was prepared.
- Boschelli, Diane H.,Connor, David T.
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p. 121 - 124
(2007/10/02)
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- A practical synthesis of 2-butyl-4(5)-chloro-5(4)-hydroxymethyl-1H-imidazole
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A practical process for the synthesis of 2-butyl-4-hydroxymethyl imidazole (4) followed by chlorination to provide chloroimidazole 1 in an overall 71% yield has been developed.
- Shi,Frey,Tschaen,Verhoeven
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p. 2623 - 2630
(2007/10/02)
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- Hypotensive imidazole derivatives
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Novel imidazole derivatives of the formula: STR1 wherein R1 is lower alkyl or, phenyl-C1-2 alkyl which may be substituted with halogen or nitro; R2 is lower alkyl, cycloalkyl or, phenyl which may be substituted with halogen, lower alkyl, lower alkoxyl or di(lower alkyl)amino, one of R3 and R4 is of the formula: --(CH2)n --COR5 in the formula R5 is amino, lower alkoxyl or hydroxyl and n is integer of 0, 1 or 2, and the other is hydrogen or halogen; provided that R1 is lower alkyl or phenethyl when R3 is halogen, n is 1 and R5 is lower alkoxyl or hydroxyl, and their salts have hypotensive activity.
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