Category: 386704-04-7

On June 2, 2017, Vara, Brandon A.; Patel, Niki R.; Molander, Gary A. published an article.Related Products of 386704-04-7 The title of the article was O-Benzyl Xanthate Esters under Ni/Photoredox Dual Catalysis: Selective Radical Generation and Csp3-Csp2 Cross-Coupling. And the article contained the following:

Alkyl xanthate esters are perhaps best known for their use in deoxygenation chem. However, their use in cross-coupling chem. has not been productive, which is due, in part, to inadequate xanthate activation strategies. Herein, we report the use of O-benzyl xanthate esters, readily derived from alcs., as radical pronucleophiles in Csp3-Csp2 cross-couplings under Ni/photoredox dual catalysis. Xanthate (C-O) cleavage is found to be reliant on photogenerated (sec-butyl) radical activators to form new carbon-centered radicals primed for nickel-catalyzed cross-couplings. Mechanistic experiments support the fact that the key radical components are formed independently, and relative rates are carefully orchestrated, such that no cross reactivity is observed The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Related Products of 386704-04-7

The Article related to cross coupling benzyl xanthate ester nickel photoredox dual catalysis, radical generation xanthate cross coupling, alkyl xanthate esters, carbon-centered radicals, cross-coupling, metal-catalyzed reactions, selective radical generation and other aspects.Related Products of 386704-04-7

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On April 2, 2009, Ghosh, Arun K.; Liu, Chunfeng; Devasamudram, Thippeswamy; Lei, Hui; Swanson, Lisa M.; Ankala, Sudha V.; Lilly, John C.; Bilcer, Geoffrey M. published a patent.Formula: C7H6F3NO The title of the patent was Preparation of (3-hydroxy-4-amino-butan-2-yl)-3-[2-(thiazol-2-yl)pyrrolidine-1-carbonyl]benzamide derivatives and related compounds as selective beta-secretase inhibitors. And the patent contained the following:

The title compounds [I; A1 = each (un)substituted cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; A2 = each cycloalkylene, heterocycloalkylene, arylene, or heteroarylene; X = CH2, O, (un)substituted NH, or S(O)w; or where X is CH or N, and is the attachment point for R6 or R7; L1, L5 = a bond, (un)substituted NH, S(O)q, (un)substituted alkylene; L4 = a bond, C(O), (un)substituted NH, S(O)q, (un)substituted alkylene; R2, R3 = S(O)2R11, C(O)R12, each (un)substituted NH2, alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, aralkyl, heteroaryl, or heteroaralkyl; R4, R5 = H, halogen, NO2, each (un)substituted OH, NH2, alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, aralkyl, heteroaryl, or heteroaralkyl, S(O)nR11, C(O)R12; R6, R7 = H, halogen, NO2, each (un)substituted OH, NH2, alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, aralkyl, heteroaryl, or heteroaralkyl, S(O)nR11, C(O)R12; R11 = H, each (un)substituted alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, aralkyl, heteroaryl, or heteroaralkyl; R12 = H, each (un)substituted NH2, OH, alkyl, cycloalkyl, cycloalkylalkyl, heterocycloalkyl, heterocycloalkylalkyl, aryl, aralkyl, heteroaryl, or heteroaralkyl; m = 0-2] or pharmaceutically acceptable salts or solvates thereof were prepared The present invention provides novel β-secretase inhibitors which are capable of selectively reducing memapsin 2 catalytic activity relative to memapsin 1 catalytic activity or cathepsin D by greater than ∼5 or ∼10-fold. It also provides methods for their use, including methods of treating of Alzheimer’s disease. Thus, to 330 mg (R)-3-methyl-5-[2-(4-methylthiazol-2-yl)pyrrolidine-1-carbonyl]benzoic acid in CH2Cl2 at room temperature, 269 mg 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 162 mg HOBT were added, stirred at room temperature for 20 min, cooled to 0°, treated with a solution of (2R,3S)-3-amino-4-phenyl-1-[3-(trifluoromethyl)benzylamino]butan-2-ol and 2 mL diisopropylethylamine in CH2Cl2, and stirred at room temperature for 16 h to yield 60% N-[(2S,3R)-3-hydroxy-1-phenyl-4-[[3-(trifluoromethyl)benzyl]amino]butan-2-yl]-3-methyl-5-[[(R)-2-(4-methylthiazol-2-yl)pyrrolidin-1-yl]carbonyl]benzamide (II). II showed Ki of 7.09, 1,079.9, and 825.73 nM, for inhibiting memapsin 2 (β-secretase), cathepsin D, memapsin 1 (β-secretase 2), resp., and showed IC50 of 23 nM against memapsin 2 (β-secretase). The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Formula: C7H6F3NO

The Article related to thiazolylpyrrolidinecarbonylbenzamide preparation selective secretase inhibitor, alzheimer disease treatment thiazolylpyrrolidinecarbonylbenzamide preparation, hydroxyaminobutanylthiazolylpyrrolidinecarbonylbenzamide preparation secretase inhibitor and other aspects.Formula: C7H6F3NO

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On October 3, 2013, Saito, Noriko; Egi, Jun; Nagai, Hiroshi; Ueno, Megumi; Shintani, Yusuke; Inaba, Yusuke; Adachi, Michiaki; Hirai, Yuichi; Kawazu, Takeshi; Yasutake, Koichi; Takahashi, Daiki published a patent.Synthetic Route of 386704-04-7 The title of the patent was Preparation of triazinone compounds as T-type calcium channel inhibitors. And the patent contained the following:

The title compounds [I; R1 = H, halo, each (un)substituted C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, mono- or di(C1-6 alkyl)amino, or C3-11 cycloalkyl; L1, L2 = a single bond, (un)substituted NH or C1-6 alkylene, O, S(O), SO2; B = each (un)substituted C3-11 cycloalkylene, C3-11 cycloalkenylene, 3-11 membered heterocyclylene, C6-14 arylene, 5-10 membered heteroarylene, C1-6 alkylene, C2-6 alkenylene, or C2-6 alkynylene; A = each (un)substituted C1-6 alkyl, C2-6 alkenyl, C3-11 cycloalkyl, C3-11 cycloalkenyl, 3-11 membered heterocyclyl, C6-14 aryl, or 5-10 membered heteroaryl; L3 = (un)substituted C1-6 alkylene optionally having one of the methylene groups replaced by C(O) or C(S); D = each (un)substituted C3-11 cycloalkyl, C3-11 cycloalkenyl, 3-11 membered heterocyclyl, C6-14 aryl, or 5-10 membered heteroaryl], tautomers or pharmaceutically acceptable salts of the compounds, or solvates of the compounds, the tautomers or the pharmaceutically acceptable salts are prepared These compounds have an inhibitory activity on a T-type voltage-dependent calcium channel and are useful for the prevention, treatment, and/or improvement of diseases for which the T-type calcium channel-inhibitory activity are effective, in particular pain, more specifically neuropathic pain. Thus, amination of 1,3,5-trichlorotriazine with 1-(4-fluorophenyl)piperazine dihydrochloride in the presence of Na2CO3 in THF at room temperature for 3 days quant. gave 2,4-dichloro-6-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazine which underwent hydrolysis with aqueous NaOH solution at room temperature for 2 days and 2 h to give 79% 6-chloro-4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-one (II; X = Cl). Hydrogenation of II (X = Cl) in the presence of Pd(OH)2/activated charcoal in aqueous acetic acid solution under hydrogen atm. at room temperature for 3 days gave 99% 4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-one II (X = H) which underwent benzylation by 4-chlorobenzyl bromide in the presence of K2CO3 in N,N-dimethylformamide at 70° for 5 h to give 53% 1-(4-Chlorobenzyl)-4-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazin-2(1H)-one (III). III and (R)-4-[4-(4-fluorophenyl)-5-hydroxy-5,6-dihydropyridin-1(2H)-yl]-1-[[5-(trifluoromethyl)thiophen-2-yl]methyl]-1,3,5-triazin-2(1H)-one (IV) showed IC50 of 0.17 and 0.00046 μM, resp., for inhibiting the cellular calcium influx in KSE293 cells expressing human type T calcium channel (Cav3.2). The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Synthetic Route of 386704-04-7

The Article related to triazinone preparation t type calcium channel inhibitor, benzylphenylpiperazinyltriazinone phenylpyridinylthiophenylmethyltriazinone preparation t type calcium channel inhibitor, pain neuropathic pain treatment prevention improvement triazinone preparation and other aspects.Synthetic Route of 386704-04-7

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On April 1, 2022, Liu, Can; Li, Kang; Shang, Rui published an article.Computed Properties of 386704-04-7 The title of the article was Arenethiolate as a Dual Function Catalyst for Photocatalytic Defluoroalkylation and Hydrodefluorination of Trifluoromethyls. And the article contained the following:

An arene thiolate with an appropriate substituent was photoactivated under visible light to function as both a strongly reducing electron-donating redox catalyst and a HAT catalyst to enable catalytic C-F activation of trifluoromethyl substrates for selective hydrodefluorination and coupling with various alkenes in the presence of formate salts. These reactions demonstrated the promising utility of arenethiolates as dual function photocatalysts. The synthetic utility of this method was demonstrated by the broad scope of amenable trifluoromethyl substrates, including trifluoromethylated (hetero)arenes, trifluoroacetates, and trifluoroacetamides, which exhibited high levels of chemoselectivity. The reaction efficacy allowed site-selective late-stage functionalization of multitrifluoromethylated bioactive compounds and pharmaceuticals. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Computed Properties of 386704-04-7

The Article related to difluoroarene preparation, trifluoroarene thiol catalyst photochem defluoroalkylation, difluoroamide preparation, trifluoroacetamide thiol catalyst photochem defluoroalkylation, difluoroacetate preparation, trifluoroacetate thiol catalyst photochem defluoroalkylation and other aspects.Computed Properties of 386704-04-7

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On December 17, 2009, Knust, Henner; Nettekoven, Matthias; Pinard, Emmanuel; Roche, Olivier; Rogers-Evans, Mark published a patent.Quality Control of (6-(Trifluoromethyl)pyridin-3-yl)methanol The title of the patent was Preparation of heteroaromatic monoamides as orexin receptor antagonists. And the patent contained the following:

The present invention is concerned with novel amides of formula [I; (i) Ar1 = heteroaryl, Ar2 = Ph, and Ar = Ph or heteroaryl; or (ii) Ar1 = Ph, Ar2 = heteroaryl, and Ar = Ph or heteroaryl; or (iii) Ar1 = heteroaryl, Ar2 = heteroaryl, and Ar = Ph or heteroaryl; R1 = H, halogen, lower alkyl, halo-lower alkyl, lower alkoxy; R2 = H, halogen, lower alkyl, halo-lower alkyl, lower alkoxy, halo-lower alkoxy; R3 = H, halogen, lower alkyl, halo-lower alkyl, hydroxy-lower alkyl, cycloalkyl-lower alkyl, C(O)O-lower alkyl, C(O)NH-lower alkyl, (CH2)m-O-lower alkyl, lower alkoxy, etc.; or where Ar2 = Ph and o = 2, R3 optionally is R3 and R3′ which together with the corresponding carbon atoms to which they are attached form a non aromatic ring containing the groups (CH2)4, (CH2)3, CH2S(O)2CH2, N(Me)C(O)N(Me), (CH2)2O, O(CH2)2O, O(CH2)2CH(OH), O(CH2)2, O(CH2)3, etc.; R4, R5 = H, hydroxy, lower alkyl, lower alkoxy, CH2NH2, O-C(O)lower alkyl, or NRR’; or R4 and R5 together are :O; R, R’ = H, S(O)2-lower alkyl, cycloalkyl, (CH2)mOH, (CH2)mO-lower alkyl, C(O)CH(NH2)Ph, or oxetan-3-yl optionally substituted by CH2NH2, or NRR’ together form a heterocycloalkyl ring, optionally containing in addition to the N atom a further heteroatom, selected from the group consisting of N, S and O; n, o, p = 1-3; m = 0-2] or pharmaceutically suitable acid addition salts, optically pure enantiomers, racemates or diastereomeric mixtures thereof. These compounds are orexin receptor antagonists that may be useful in the treatment of disorders, in which orexin pathways are involved, e.g. in arousal, sleep/wakefulness, appetite regulation and their roles in anxiety and stress response, etc. The drugs (or compounds) targeting orexin system will have beneficial therapeutic effects for the treatments of diseases like sleep disorders including sleep apnea, narcolepsy, insomnia, parasomnia, jet lag syndrome, circadian rhythms disorder, restless leg syndrome, psychiatric, neurol. and neurodegenerative disorders, etc. Thus, 500 mg (3,4-dimethylphenyl)[2-(6-trifluoromethylpyridin-3-yl)ethyl]amine > was condensed with 300 mg (4-fluorophenyl)oxoacetic acid using in CH2Cl2 with stirring for 12 h at ambient temperature to give, after workup and silica gel chromatog., N-(3,4-dimethylphenyl)-2-(4-fluorophenyl)-2-oxo-N-[2-(6-trifluoromethylpyridin-3-yl)ethyl]acetamide (527 mg, 70%) (II) as a light yellow. II (515 mg) was reduced by 88 mg NaBH4 in MeOH with stirring for 12 h at ambient temperature to give, after workup and silica gel chromatog., N-(3,4-dimethylphenyl)-2-(4-fluorophenyl)-2-hydroxy-N-[2-(6-trifluoromethylpyridin-3-yl)ethyl]acetamide (501 mg, 97%) which was separated by chromatog. on a chiral column to give (S)-N-(3,4-dimethylphenyl)-2-(4-fluorophenyl)-2-hydroxy-N-[2-(6-trifluoromethylpyridin-3-yl)ethyl]ethanamide (III). III showed inhibited orexin receptor-2 receptor (OX2R) with Kb of 0.0005 μM in an intracellular Ca2+ mobilization assay in Chinese hamster ovary mutant cell line stably expressing human OX2R. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Quality Control of (6-(Trifluoromethyl)pyridin-3-yl)methanol

The Article related to phenylpyridinylethylacetamide preparation orexin receptor antagonist, sleep disorder treatment phenylpyridinylethylacetamide preparation, heteroaromatic monoamide preparation orexin receptor antagonist, psychiatric neurol neurodegenerative disorder treatment heteroaromatic monoamide preparation and other aspects.Quality Control of (6-(Trifluoromethyl)pyridin-3-yl)methanol

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On June 5, 2003, Devita, Robert J.; Chang, Lehua; Chaung, Danny; Hoang, Myle; Jiang, Jinlong; Lin, Peter; Sailer, Andreas W.; Young, Jonathan R. published a patent.Product Details of 386704-04-7 The title of the patent was Preparation of 2-aminoquinolines as melanin concentrating hormone receptor (MCH-1R) antagonists.. And the patent contained the following:

Title compounds [I; R1, R2 = H, (substituted) alkyl, alkenyl, alkynyl, cycloalkylalkyl, aralkyl, etc.; R1R2N = 4-11 membered (bridged) (substituted) heterocyclyl; R3, R4 = H, halo, (substituted) alkyl, alkenyl, alkynyl, perfluoroalkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaralkyl, OR7, N(R7)2, cyano, etc.; R3R4 = atoms to form 5-7 membered (substituted) ring; R5 = H, halo, alkyl, perfluoroalkyl, OR7, N(R7)2; R6 = (CH2)nR7, (CH2)nCN, (CH2)nCO2R7, (CH2)nOR7, (CH2)nN(R7)2, etc.; R7 = H, alkyl, aryl, heteroaryl, cycloalkyl, aralkyl, aralkenyl, cycloalkylalkenyl, etc.; n = 0-5], were prepared for the treatment or prevention of obesity, eating disorders, osteoarthritis, cancer, AIDS wasting, cachexia, frailty, mental disorders, stress, cognitive disorders, sexual function, reproductive function, kidney function, locomotor disorders, attention deficit disorder (ADD), substance abuse disorders and dyskinesias, Huntington’s disease, epilepsy, memory function, and spinal muscular atrophy. Thus, 2-piperidin-1-ylquinolin-6-amine and (2E)-3-(4-chlorophenyl)prop-2-enoyl chloride were stirred 3 h in HOAc to give (2E)-3-(4-chlorophenyl)-N-(2-piperidin-1-ylquinolin-6-yl)prop-2-enamide hydrochloride. I bound to MCH-1R receptors with IC50 = 0.1-10000 nM. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Product Details of 386704-04-7

The Article related to aminoquinoline preparation melanin concentrating hormone receptor mch1r antagonist, obesity eating disorder osteoarthritis cancer wasting treatment aminoquinoline preparation, cachexia frailty mental disorder stress treatment aminoquinoline preparation, cognitive disorder sexual dysfunction reproductive dysfunction treatment aminoquinoline preparation and other aspects.Product Details of 386704-04-7

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On May 28, 2020, Zhong, Wenge published a patent.Category: alcohols-buliding-blocks The title of the patent was Preparation of 1H-benzimidazole-6-carboxylic acid derivatives as glucagon-like peptide-1 receptor (GLP-1R) agonists and uses thereof. And the patent contained the following:

The title compounds represented by formula I (X1-X5, Y1-Y5, Z1-Z4, T2-T4, T6-T8, Ra, Rb, Rc, Rd, R1-R3, m, n, and o are defined below) or pharmaceutically acceptable salts, stereoisomers, solvates, or hydrates thereof are prepared for use in, e.g. treating type 2 diabetes mellitus, pre-diabetes, obesity, non-alc. fatty liver disease, non-alc. steatohepatitis, and cardiovascular disease. X1-X5, Y1-Y5, Z1-Z4, T2-T4, and T6-T8 are defined as [the dashed line with a solid line = a single bond or a double bond; X1, X2, X3, X4, X5 = each independently N or CH, wherein no more than three of X1-X5 are N and ring A does not contain 3-nitrogen ring atoms at 3 contiguous positions; W = O, S, or each (un)substituted CH2 or NH; Y1, Y3, Y4, Y5 = each independently N, NH, CH, or CH2; Y2, Y6 = each independently N, C, or CH, wherein there is no more than 3-nitrogen ring atoms in ring B and ring B does not contain 3-nitrogen ring atoms at 3 contiguous positions; Z1, Z2 = each independently N, C, or CH, wherein at least one of Z1 and Z2 is N; Z3, Z4 = each independently a bond, CH, CH2, CH:CH, CH2CH2, CH2CH, or CHCH2, wherein ring C contains no more than two double bonds; provided that when ring B = (un)substituted pyridine-2,6-diyl, then (1) W is not O, and/or (2) ring C is not (un)substituted piperazine-1,4-diyl and/or (3) ring C is not (un)substituted piperidine-1,4-diyl; wherein Z1 is N, and/or (4) ring A is not phenyl; T2, T3, T4 = each independently N, O, S, C, or each (un)substituted NH or CH ; T6, T6, T8 = each independently selected N or (un)substituted CH; wherein no more than 4 of T2, T3, T4, T6, T7, and T8 are selected from N, O, and S; EE = CO2H or a carboxylic group surrogate (e.g. C(O)CF3, CH(F)CF3, C(O)NHCN, C(O)NHOH, C(O)NHOMe, 2H-tetrazol-2-yl, etc.)]. Ra, Rb, Rc, and Rd are defined as [Ra = hydrogen, deuterium, halogen, cyano, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, 3-8 membered saturated or partially saturated heterocyclyl; Rb = hydrogen, deuterium, halogen, cyano, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl; Rc = hydrogen, deuterium, halogen, cyano, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl; Rd = hydrogen, deuterium, halogen, cyano, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl]. R1-R3, m, n, and o are defined as [R1 = independently halogen, cyano, OH, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, C2-6 alkenyl, C2-6 alkynyl, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl; R2 = independently halogen, cyano, OH, oxo, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl; R3 = independently halogen, cyano, OH, oxo, or each (un)substituted C1-6 alkyl, C1-6 alkoxy, NH2, 6-10 membered aryl, 5-8 membered heteroaryl, 3-8 membered saturated or partially saturated cycloalkyl, or 3-8 membered saturated or partially saturated heterocyclyl; m = an integer of 0-4; n, o = each independently an integer of 0-5]. Thus, sequential amination of 2,6-dichloropyridine with tert-Bu piperazine-1-carboxylate in DMSO at 110° for 12 h and (4-chloro-2-fluorophenyl)methanamine in the presence of BINAP, Pd2(dba)2, sodium tert-butoxide in toluene at 100° for 12 h gave tert-Bu 4-[6-(4-chloro-2-fluorobenzylamino)pyridin-2-yl]piperazine-1-carboxylate which was treated with CF3CO2H in CH2Cl2 and underwent alkylation with tert-Bu (S)-2-(chloromethyl)-1-(oxetan-2-ylmethyl)-1H-benzimidazole-6-carboxylate in the presence of K2CO3 in DMF at 90° for 5 h and deprotection by treatment with CF3CO2H to give (S)-2-[[4-[6-(4-chloro-2-fluorobenzylamino)pyridin-2-yl]piperazin-1-yl]methyl]-1-(oxetan-2-ylmethyl)-1H-benzimidazole-6-carboxylic acid (II). II in vitro showed EC50 of ≤0.015μM for production of cAMP in HEK293T cells expressing human GLP-1R. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Category: alcohols-buliding-blocks

The Article related to benzimidazolecarboxylic acid preparation glp 1r agonist, oxetanylmethylbenzimidazolecarboxylic acid preparation glp 1r agonist, piperazinylmethyloxetanylmethylbenzimidazolecarboxylic acid preparation glp 1r agonist, glucagon peptide 1 receptor glp 1r agonist, type 2 diabetes mellitus prediabetes obesity treatment and other aspects.Category: alcohols-buliding-blocks

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On June 26, 2014, Kobayashi, Kaori; Suzuki, Tamotsu; Okuzumi, Tatsuya published a patent.Synthetic Route of 386704-04-7 The title of the patent was Preparation of N-arylsulfonyl amino acid amide derivatives as transient receptor potential ankyrin 1 (TRPA1) antagonists and medicine containing them. And the patent contained the following:

The title compounds represented by formula [I; Ar = each (un)substituted C6-10 aryl or C1-9 heteroaryl; Y = C(Ry1)(Ry2) or a single bond; Z = C(Rz1)(Rz2), O, S, or a single bond; n, m = 0 or 1 and n+m≤1; ring A = (un)substituted phenylene or 5- or 6-membered divalent heteroaromatic ring; ring B = (un)substituted C6-10 aryl or C1-9 heteroaryl; R1 = H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halo-C1-6 alkyl, C3-6 cycloalkyl, or C3-6 cycloalkyl-C1-6 alkyl; R2, R3 = H, C1-6 alkyl, C2-6 alkenyl, or C2-6 alkynyl; R4-R8, Ry1, Ry2, Rz1, Rz2 = H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halo-C1-6 alkyl, C1-6 alkoxy, HO, halo-C1-6 alkoxy, NH2, C1-6 alkyl, mono- or disubstituted amino, or halo; each adjacent R4-R8, Ry1, Ry2, Rz1, or Rz2 together forms a double bond and/or ring; or R5 and R6, R7 and R8, Ry1 and Ry2, or Rz1 and Rz2 on the same carbon atom together form a ring; Rx1, Rx2, Rx2, Rx3, Rx4 = H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, hydroxy-C1-6 alkyl, amino-C1-6 alkyl, or mono- or di(C1-6 alkyl)amino-C1-6 alkyl; or Rx1 and Rx2 or Rx3 and Rx4 on the same carbon together form a ring] or pharmaceutically acceptable salts thereof are prepared These compounds have transient receptor potential ankyrin 1 (TRPA1) antagonistic activity and are useful for the prevention or treatment of diseases associated with a TRPA1 antagonist and TRPA1, in particular pain-related diseases, inflammatory diseases, digestive tract diseases, pulmonary diseases, bladder diseases, skin diseases, or nerve diseases, more specifically chronic pain, acute pain, asthma, chronic obstructive pulmonary disease, functional gastrointestinal disorders, reflux esophagitis, inflammatory bowel disease, or pruritus. Thus, L-proline was condensed with 5-chlorothiophene-2-sulfonyl chloride in the presence of NaOH in aqueous THF solution at room temperature overnight to give 97% (2S)-1-(5-chlorothiophene-2-sulfonyl)pyrrolidine-2-carboxylic acid which was condensed with 4-(aminomethyl)phenol using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 1-hydroxy-7-azabenzotriazole (HOAt) in the presence of Et3N in CH2Cl2 at room temperature for a few hours to give 72% (2S)-1-(5-chlorothiophene-2-sulfonyl)-N-[(4-hydroxyphenyl)methyl]pyrrolidine-2-carboxamide (II; R = H). II (R = H) was condensed with phenylboronic acid in the presence of supper acetate, Et3N, and mol. sieve 4Å in CH2Cl2 at room temperature for a few hours to give II (R = Ph). II (R = Ph) and (2S)-1-(3-thienylsulfonyl)-N-[[3-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]methyl]pyrrolidine-2-carboxamide (III) inhibited the allyl isothiocyanate-stimulated increase in cellular calcium concentration in human fetus kidney cell-derived 293T cells expressing human TRPA1 with IC50 of 0.22 and 0.0085 μM, resp. The experimental process involved the reaction of (6-(Trifluoromethyl)pyridin-3-yl)methanol(cas: 386704-04-7).Synthetic Route of 386704-04-7

The Article related to arylsulfonylproline amide preparation transient receptor potential ankyrin 1 antagonist, arylsulfonyl amino acid amide preparation trpa1 antagonist, pain inflammatory disease prevention treatment, digestive tract disease prevention treatment, pulmonary disease prevention treatment, bladder disease skin disease prevention treatment and other aspects.Synthetic Route of 386704-04-7

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