- N-SUBSTITUTED-DIOXOCYCLOBUTENYLAMINO-3-HYDROXY-PICOLINAMIDES USEFUL AS CCR6 INHIBITORS
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The present invention relates to N-substituted-dioxocyclobutenylamino-3-hydroxy-picolinamide compounds of Formulae (IA and 1B) or a pharmaceutically acceptable salt or hydrate thereof, that inhibit CC chemokine receptor 6 (CCR6), pharmaceutical compositions containing these compounds, and the use of these compounds for treating or preventing diseases, conditions, or disorders ameliorated by inhibition of CCR6.
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Paragraph 0664; 0665
(2020/04/10)
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- A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones
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The acylation of the acetonitrile anion with lactones and esters in ethereal solvents was successfully exploited using inexpensive KOt-Bu to obtain a variety of β-ketonitriles and trifunctionalized building blocks, including useful O-unprotected diols. It was discovered that lactones react to produce the corresponding derivatized cyclic hemiketals. Furthermore, the addition of a catalytic amount of isopropanol, or 18-crown-6, was necessary to facilitate the reaction and to reduce side-product formation under ambient conditions.
- Pienaar, Daniel P.,Butsi, Kamogelo R.,Rousseau, Amanda L.,Brady, Dean
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supporting information
p. 2930 - 2935
(2019/12/23)
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- A Selective and Functional Group-Tolerant Ruthenium-Catalyzed Olefin Metathesis/Transfer Hydrogenation Tandem Sequence Using Formic Acid as Hydrogen Source
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A ruthenium-catalyzed transfer hydrogenation of olefins utilizing formic acid as a hydrogen donor is described. The application of commercially available alkylidene ruthenium complexes opens access to attractive C(sp3)-C(sp3) bond formation in an olefin metathesis/transfer hydrogenation sequence under tandem catalysis conditions. High chemoselectivity of the developed methodology provides a remarkable synthetic tool for the reduction of various functionalized alkenes under mild reaction conditions. The developed methodology is applied for the formal synthesis of the drugs pentoxyverine and bencyclane.
- Zieliński, Grzegorz K.,Majtczak, Jaros?awa,Gutowski, Maciej,Grela, Karol
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p. 2542 - 2553
(2018/03/09)
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- Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling
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The rhodium-catalyzed enantioselective desymmetrization of symmetric γ,δ-unsaturated amides via carbonyl-directed catalytic asymmetric hydroboration (directed CAHB) affords chiral secondary organoboronates with up to 98% ee. The chiral γ-borylated products undergo palladium-catalyzed Suzuki-Miyaura cross-coupling via the trifluoroborate salt with stereoretention.
- Hoang, Gia L.,Yang, Zhao-Di,Smith, Sean M.,Miska, Judy L.,Prez, Damaris E.,Zeng, Xiao Cheng,Takacs, James M.,Pal, Rhitankar,Pelter, Libbie S. W.
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supporting information
p. 940 - 943
(2015/03/30)
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- Enantioselective synthesis of nicotinic receptor probe 7,8-difluoro-1,2,3, 4,5,6-hexahydro-1,5-methano-3-benzazocine
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(Chemical Equation Presented) The development of a concise enantioselective synthesis of nicotinic alkaloid 1 is presented. The route features the synthesis and use of a "stable" aliphatic triflate 21 in an alkylation step to generate Heck precursor 24 and an enantioselective cyclization to establish a compound with the key [3.2.1]-bicyclic core, 29.
- Bashore, Crystal G.,Vetelino, Michael G.,Wirtz, Michael C.,Brooks, Paige R.,Frost, Heather N.,McDermott, Ruth E.,Whritenour, David C.,Ragan, John A.,Rutherford, Jennifer L.,Makowski, Teresa W.,Brenek, Steven J.,Coe, Jotham W.
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p. 5947 - 5950
(2007/10/03)
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- Aryl fused azapolycyclic compounds
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The present invention relates to compounds of formula (I) and their pharmaceutically acceptable salts, wherein R1, R2, R3and Z are as defined herein, intermediates in the synthesis of such compounds, pharmaceutical compositions containing such compounds and methods of using such compounds in the treatment of neurological and psychological disorders.
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- Antiparasitic agents
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The invention provides novel compounds having the formula: STR1 wherein R when taken individually is H; R1 when taken individually is H or OH; R and R1 when taken together represent a double bond; R2 is an alpha-branched C3 -C8 alkyl, alkenyl, alkynyl, alkoxyalkyl or alkylthioalkyl group; a C3 -C8 cycloalkyl, C5 -C8 cycloalkenyl or C5 -C8 cycloalkylalkyl group, any of which may be substituted by methylene or one or more C1 -C4 alkyl groups or halo atoms; or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may be substituted by one or more C1 -C4 alkyl groups or halo atoms; R3 is hydrogen or methyl; R4 is H or 4'-(alpha-L-oleandrosyl)-alpha-L-oleandrosyloxy with the proviso that when R2 is alkyl it is not isopropyl or sec-butyl; when R4 is H, each of R and R1 is H, and R2 is not methyl or ethyl; and when R4 is H, R is H, R1 is OH, and R2 is not 2-buten-2-yl, 2-penten-2-yl or 4-methyl-2-penten-2-yl. The compounds are broad spectrum antiparasitic agents having utility as anthelmintics, ectoparasiticides, insecticides and acaricides. The invention also provides a process for producing the novel avermectin and milbemycin derivatives by adding a carboxylic acid or derivative thereof to a fermentation of an avermectin or milbemycin producing organism.
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- Medicament compositions derived from quinolizine and quinolizinone and methods of use thereof
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The present invention is directed to the use of esters of hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one and hexahydro-8-hydroxy-2,6-methano-2H-quinolizines in the manufacture of a medicament for the treatment of anxiety, psychosis, glaucoma and for the stimulation of gastric motility.
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- (Lig)Ni(0) induced preparation of mono- and dicarboxylic acids from cyclopentene and carbon dioxide
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Cyclopentene is shown to be an ideal substrate for coupling reactions with (Lig)nickel(0) systems. By variation of the ligands and addition of promoters, it is possible by successive application of carbon dioxide or carbon monoxide to prepare highly selectively series of cyclopentane- and cyclopentenecarboxylic acids (six examples), 4, 5, 6, 11, 14, 15, cyclopentanedicarboxylic acids (three examples), 7, 8, 12, or 2-hydroxycyclopentanecarboxylic acid (9) in good yields. The C5-skeleton is retained in the products.
- Hoberg,Ballesteros,Sigan,Jegat,Milchereit
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p. 395 - 398
(2007/10/02)
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- Esters of hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3-(4H)-one and related compounds
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The present invention is directed to a group of esters of hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(3H)-ones and related compounds. The compounds are prepared from the appropriate carboxylic acids and alcohols by standard procedures or, where steric factors are significant, a new process which makes use of heavy metal salts of super acids can be used. The compounds involved are useful in the treatment of migraine and similar disorders and in cytotoxic drug-induced vomiting.
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- Use of quinolizine and quinolizinone derivatives in the manufacture of medicaments for the treatment of cardiac arrhythmia
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The present invention is directed to the use of heterocyclic esters of hexahydro-8-hydroxy-2,6-methano-2H--quinolizin-3(4H)-ones and hexahydro-B-hydroxy-2,6-methano--2H-quinolizines in the manufacture of cardiac antiarrhythmic agents
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- Ozonolysis of Tetrasubstituted Ethylenes, Cycloolefins, and Conjugated Dienes on Polyethylene
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Ozonolyses of four tetrasubstituted ethylenes (7a-d), of two medium-sized cycloolefins (10a,b), and of norbornene (14) on polyethylene gave the corresponding ozonides, which could not be obtained by ozonolyses in solution.Ozonolyses of three conjugated dienes (25a,b,28) on polyethylene gave the corresponding diozonides, as the first examples of this class of ozonides.The thermal decomposition of some of the ozonides has been studied.
- Griesbaum, Karl,Volpp, Willi,Greinert, Reinhard,Greunig, Hans-Joachim,Schmid, Jurgen,Henke, Henning
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p. 383 - 389
(2007/10/02)
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- A short and stereoselective synthesis of (±)-aristeromycin
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A new stereoselective three-step total synthesis of (±)-aristeromycin starting from readily available 1-hydroxymethyl-3-cyclopentene is described.
- Hutchison,Grim,Chen
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p. 451 - 452
(2007/10/02)
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- 2. 2. 1.
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A new class of bicyclic compounds containing a single silicon atom at the bridge, 2-exo- and endo-substituted 2-methyl-2-silabicyclo left bracket 2. 2. 1 right bracket heptanes, have been prepared from the corresponding 3-cyclopentenylmethylhydrosilane by the intramolecular hydrosilylation catalyzed by chloroplatinic acid, and their structures were unequivocally assigned by **1H and **1**3C NMR spectra. Dramatic crossover from inversion to retention was found in the phenylation of chlorosilanes with phenyllithium and phenylmagnesium bromide in ether. Regio- and stereoselective insertion of dichlorocarbene generated from phenyl(bromodichloromethyl)mercury, or from chloroform and sodium hydroxide in the presence of a phase transfer catalyst, into C//(//6//)-H//(//e//x//o//) bond of 2-silanorbornanes is observed.
- Hosomi,Mikami,Sakurai
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p. 2784 - 2794
(2007/10/02)
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