- Base directed palladium catalysed Heck arylation of acrolein diethyl acetal in water
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The selective Heck arylation of acrolein diethyl acetal catalysed by [Pd(NH3)4]Cl2 in the presence of RAME-β-CD in water as solvent is described. Depending on the base (i.e. NaOAc or HN(i-Pr)2) good to high selectivity's towards, respectively, the cinnamaldehydes 2 or the 3-arylpropionic esters 1 were achieved. The results support that depending on the base different palladium intermediate complexes are formed. Using NaOAc, {[ArPdX(H2O)2]} complex is preferentially generated giving the cinnamaldehyde 2. On the other hand, in the presence of HN(i-Pr)2, a L-type ligand, [ArPdX(HN(i-Pr) 2(H2O)] or [ArPdX(HN(i-Pr)2(HN(i-Pr) 2)] will be generated leading to the formation of the 3-arylpropionic ester 1. For the last, coordinated amine participates very probably to the formation of the esters through intramolecular syn β-H elimination.
- Al-Maksoud, Walid,Menuel, Stéphane,Jahjah, Mohamad,Monflier, Eric,Pinel, Catherine,Djakovitch, Laurent
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p. 250 - 258
(2013/11/19)
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- 7-HYDROXY-PYRAZOLO[1,5-A] PYRIMIDINE COMPOUNDS AND THEIR USE AS CCR2 RECEPTOR ANTAGONISTS
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The compounds of formula (I) are antagonists of the CCR2 receptor Wherein R1-7 and A are as defined in the claims.
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Paragraph 0252
(2013/10/07)
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- 7-HYDROXY-PYRAZOLO[1,5-A] PYRIMIDINE COMPOUNDS AND THEIR USE AS CCR2 RECEPTOR ANTAGONISTS
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The compounds of formula (I) are antagonists of the CCR2 receptor Wherein R1-7 and A are as defined in the claims.
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Page/Page column 39
(2012/04/17)
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- PROCESS FOR PREPARING CINACALCET HYDROCHLORIDE
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Processes for preparing cinacalcet are provided.
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Page/Page column 28
(2008/06/13)
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- CoBr2(Bpy): An efficient catalyst for the direct conjugate addition of aryl halides or triflates onto activated olefins
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An efficient cobalt-catalyzed method devoted to the direct conjugate addition of functionalized aryl compounds onto Michael acceptors is described. The CoBr2(2,2′-bipyridine) complex appears to be an extremely suitable catalyst for the activation of a variety of aromatic reagents ranging from halides to triflates functionalized by reactive groups. This procedure allows for the synthesis of compounds resulting from 1,4-addition in good to excellent yields. The versatility of this original process represents a simple alternative to most known methods using organometallic reagents.
- Amatore, Muriel,Gosmini, Corinne,Perichon, Jacques
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p. 6130 - 6134
(2007/10/03)
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- 3-arylpropanoate esters through the palladium-catalyzed reaction of aryl halides with acrolein diethyl acetal
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The reaction of aryl halides with acrolein diethyl acetal in the presence of Pd(OAc)2, n-Bu3N, and n-Bu4NCl in DMF at 90°C affords ethyl 3-arylpropanoates. A variety of functional groups are tolerated in the aryl halides, including ether, aldehyde, ketone, ester, nitrile, and nitro groups. ortho-Substituents do not hamper the reaction. 3-Arylpropanoate esters were isolated in good to excellent yields with many neutral, electron-rich and electron-poor aryl iodides and electron-poor aryl bromide. Neutral and electron-rich aryl bromides gave the desired ester in moderate yields.
- Battistuzzi, Gianfranco,Cacchi, Sandro,Fabrizi, Giancarlo,Bernini, Roberta
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p. 1133 - 1136
(2007/10/03)
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- Inhibition of uridine phosphorylase: Synthesis and structure-activity relationships of aryl-substituted 5-benzyluracils and 1-[(2- hydroxyethoxy)methyl]-5-benzyluracils
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A series of 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils were synthesized and tested for inhibition of murine liver uridine phosphorylase (UrdPase). Inhibitors of UrdPase are reported to enhance the chemotherapeutic utility of 5-fluoro-2'-deoxyuridine and 5-fluorouracil and to ameliorate zidovudine- induced anemia in animal models. We prepared a series of 5-aryl-substituted analogues of 5-benzylacyclouridine (BAU), a good inhibitor of UrdPase (IC50 of 0.46 μM), to develop a compound with enhanced potency and improved pharmacokinetics. The first phase of structure-activity relationship studies on a series of 32 aryl-substituted 5-benzyluracils found several 5-(3- alkoxybenzyl) analogues of 5-benzyluracil with enhanced potency. The acyclovir side chain, the (2-hydroxyethoxy)methyl group, was substituted on the more potent aryl-substituted 5-benzyluracils. The two most potent compounds, 10y (3-propoxy) and 10dd (3-sec-butoxy), were inhibitors of UrdPase with IC50s of 0.047 and 0.027 μM, respectively. Six compounds were tested in vivo for effects on steady-state concentrations of circulating uridine in rats. Plasma uridine levels were elevated 3-9-fold by compound levels that ranged from 8 to 50 μM.
- Orr,Musso,Boswell,Kelley,Joyner,Davis,Baccanari
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p. 3850 - 3856
(2007/10/02)
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- PHENYL ALKYLAMINOPYRIMIDONES
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The compounds are phenyl alkylaminopyrimidones which are histamine H. sub.2-antagonists. A specific compound of the present invention is 2-[2-[3-(dimethylaminomethyl)benzylthio]ethylamino]-5-(6-methyl-3-pyridylme thyl)-4-pyrimidone.
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- GUANIDINOTHIAZOLYL DERIVATIVES
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The compounds are guanidinothiazolyl derivatives which are histamine H. sub.2-antagonists. A specific compound of the present invention is 2-2-(2-guanidino-4-thiazolylmethylthio)ethylamino!-5-(6-methyl-3-pyridylmethy l)-4-pyrimidone.
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- Tertiary alcohols
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Tertiary alcohols of the formula: STR1 wherein Y1 represents a carbonyl or hydroxymethylene group, and either (i) A1 represents a direct bond and R1 represents a phenyl group which may optionally carry one or more substituents selected from halogen atoms, straight- or branched-chain alkyl or alkoxy groups, each containing from 1 to 4 carbon atoms, and the trifluoromethyl group, or (ii) A1 represents a straight- or branched-chain alkylene group containing from 1 to 10 carbon atoms and R1 represents a hydrogen atom, or a phenyl, phenoxy or phenylthio group each of which may optionally carry one or more substituents selected from halogen atoms, straight- or branched-chain alkyl or alkoxy groups, each containing from 1 to 4 carbon atoms, and the trifluoromethyl group, are new compounds of use in the field of mammalian reproduction and also of use in the control of insects and acarines.
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- ISOUREAS AND ISOTHIOUREAS
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The compounds are isoureas and isothioureas which have an O-or S-alkylpyrimidone substituent and which are histamine H 2-antagonists and antiinflammatory agents. A specific compound of this invention is 2-[5-(O-isoureido)pentylamino]-5-(6-methyl-3-pyridylmethyl)-4-pyrimidone.
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- Pyrimidine compounds
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The compounds are substituted pyrimidine compounds which are histamine H2 -antagonists. A specific compound of the present invention is 2-[2-(5-dimethylaminomethyl)-2-furylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone.
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