Abstract: This invention provides a convenient method for converting oximes into enamides. The process does not require the use of metallic reagents. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. The enamides are useful precursors to amides and amines. The invention provides a process to convert a prochiral enamide into the corresponding chiral amide. In an exemplary process, a chiral amino center is introduced during hydrogenation through the use of a chiral hydrogenation catalyst. In selected embodiments, the invention provides methods of preparing amides and amines that include the 1,2,3,4-tetrahydro-N-alkyl-1-naphthalenamine or 1,2,3,4-tetrahydro-1-naphthalenamine substructure.
Type:
Grant
Filed:
March 30, 2007
Date of Patent:
January 17, 2012
Assignee:
Sunovion Pharmacuticals Inc.
Inventors:
Hang Zhao, Stefan G. Koenig, Charles P. Vandenbossche, Surendra Singh, Harold Scott Wilkinson, Roger P. Bakale
Abstract: The instability of carbamate-protected alkyl imines has greatly hampered the development of catalytic asymmetric Mannich reactions suitable for the synthesis of optically active carbamate-protected chiral alkyl amines. A highly enantioselective Mannich reaction with in situ generation of carbamate-protected imines from stable ?-amido sulfones catalyzed by an organic catalyst has been developed. This reaction provides a concise and highly enantioselective route converting aromatic and aliphatic aldehydes into optically active aryl and alkyl ?-amino acids.
Abstract: Methods of applying cyclopropene amine derivatives and compositions thereof to inhibit ethylene receptors in plants and plant material are disclosed. Methods include applying to the plant an effective ethylene response-inhibiting amount of at least one cyclopropene amine compound or composition thereof. Cyclopropene amine compounds, enantiomers, stereoisomers or salts thereof are also provided.
Abstract: Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein m, p, q, Ar, R1 and R2 are as defined herein. Also provided are methods for preparing, compositions comprising, and methods for using compounds of formula I.
Type:
Grant
Filed:
November 15, 2007
Date of Patent:
January 10, 2012
Assignee:
Roche Palo Alto LLC
Inventors:
Robert Greenhouse, Ralph New Harris, III, Saul Jaime-Figueroa, James M. Kress, David Bruce Repke, Russell Stephen Stabler
Abstract: The present invention discloses a pharmaceutical-grade ferric organic compounds, including ferric citrate, which are soluble over a wider range of pH, and which have a large active surface area. A manufacturing and quality control process for making a pharmaceutical-grade ferric citrate that consistently complies with the established Manufacture Release Specification is also disclosed. The pharmaceutical-grade ferric organic compounds are suitable for treating disorders characterized by elevated serum phosphate levels.
Abstract: In accordance with the present invention, a hydrolyzable silane of low VOC-generating potential is provided which possesses: (i) at least one organofunctional group, said group being a non-bulky electron-withdrawing group and/or a group which interacts with an organic resin, the organofunctional group being bonded to a silicon atom of a hydrolyzable silyl group through a stable bridging groups; and (ii) at least one hydrolyzable group bonded to silicon and containing at least two heteroatoms selected from the group consisting of oxygen, nitrogen and their combinations, hydrolysis of the hydrolyzable group generating a compound having a vapor pressure lower than 0.1 mm Hg at 20° C.
Type:
Grant
Filed:
March 30, 2007
Date of Patent:
January 3, 2012
Assignee:
Momentive Performance Materials Inc.
Inventors:
Misty W. Huang, Antonio Chaves, Bruce A. Waldman, Shayne J. Landon
Abstract: A reductive cross coupling reaction process for functionalization of a nucleophilic alkene can be achieved. The nucleophilic alkene and a nucleophilic cross coupling partner compound can be reacted in the presence of an oxidizable alcohol and a suitable catalyst to form a reductive coupling product. Various additives can also be useful to refine the process such as by mitigating certain undesirable intermediates, facilitating specific site selectivity for various substitutions or reaction sites, etc. Chiral additives can be optionally used which act to provide asymmetric catalysis, e.g. allow for regioselective and stereoselective production of reductive coupling products. A reductive cross coupling pathway can include oxidizing the oxidizable alcohol to form a catalyst hydride. The nucleophilic alkene can be inserted into the catalyst hydride to form a catalyst-alkyl intermediate.
Abstract: Systems and methods for processing glycerol into one or more useful products are provided. The method can include decreasing a pH of a mixture comprising glycerol and fatty acids to produce an emulsion comprising a glycerol-rich portion and a fatty acids-rich portion. At least a portion of the glycerol-rich portion can be reacted with at least one of an oxidant and a catalyst at conditions sufficient to produce a reacted product comprising glyceric acid, oxalic acid, glycolic acid, formic acid, or any combination thereof.
Abstract: A two-photon probe for real-time monitoring of intracellular calcium ions is provided. The two-photon probe is very suitable for real-time imaging of intracellular calcium ions, shows 20˜50-fold TPEF enhancement in response to Ca2+, has a dissociation constant (KdTP) of 0.14±0.02 to 0.25±0.03 ?M, and emits 5-fold stronger TPEF than currently available one-photon fluorescent Ca2+ probes. Unlike the previously available probes, the two-photon probe can selectively detect dynamic levels of intracellular free Ca2+ in live cells and living tissues without interference from other metal ions and from the membrane-bound probes. Moreover, the two-photon probe is capable of monitoring the calcium waves at a depth of 100-300 ?m in live tissues for 1,100-4,000 s using two-photon microscopy (TPM) with no artifacts of photo-bleaching. Further provided are a method for preparing the two-photon probe and a method for real-time monitoring of intracellular calcium ions using the two-photon probe.
Type:
Grant
Filed:
January 21, 2008
Date of Patent:
December 27, 2011
Assignee:
Korea University Industry and Academy Cooperation Foundation
Abstract: The invention relates to organomodified siloxane compounds of the general formula (I) the use of at least one of these compounds for producing aqueous preparations for the water-repellent impregnation of organic or inorganic materials.
Type:
Grant
Filed:
March 7, 2008
Date of Patent:
December 27, 2011
Assignee:
Evonik Goldschmidt GmbH
Inventors:
Sascha Herrwerth, Frank Koenig, Andrea Lohse
Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2?CClCH2Cl (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF3CCl?CH2, preferably in a 80-96% selectivity. The CF3CCl?CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl?CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3.
Type:
Grant
Filed:
January 3, 2007
Date of Patent:
December 27, 2011
Assignee:
Honeywell International, Inc.
Inventors:
Hsueh S. Tung, Sudip Mukhopadhyay, Michael Van Der Puy, Daniel C. Merkel, Jing Ji Ma, Cheryl L. Bortz, Barbara A. Light, Steven D. Phillips, Rajesh K. Dubey
Abstract: The compound (I) or a salt thereof has an excellent controlling activity against pests. Then the compound (I) or a salt thereof is useful for an active ingredient of a pesticidal composition.
Abstract: A compound of the present invention, or a pharmaceutically acceptable salt thereof is indicated by formula (1) below: wherein, R1, R2, R3, R4, R5, R6, Q, R8, and R9 have the same meanings as R1, R2, R3, R4, R5, R6, Q, R8, and R9 in the specification.
Abstract: Disclosed are compounds represented by structural formula (I): methods of producing compounds represented by structural formula (I), and their use in inhibiting oxidation in an oxidizable material.
Type:
Grant
Filed:
August 11, 2010
Date of Patent:
December 20, 2011
Assignee:
Polnox Corporation
Inventors:
Rajesh Kumar, Suizhou Yang, Vijayendra Kumar, Ashok L. Cholli
Abstract: Disclosed herein are a novel dicarboxylic acid salt of N,N-dimethylimidodicarbonimidic diamide, a preparation method thereof and a pharmaceutical composition comprising the same. More specifically, disclosed herein are a novel dicarboxylic acid salt of N,N-dimethylimidodicarbonimidic diamide, a crystalline acid addition salt prepared by allowing N,N-dimethylimidodicarbonimidic diamide to react with a specific dicarboxylic acid, which has improved physical and chemical properties including solubility, stability, non-hygroscopicity and anti-adhesive properties, and low toxicity, and thus is very effective in the prevention and treatment of not only diabetes and its complications in patients with so-called metabolic syndromes, in which diabetes, obesity, hyperlipidemia, fatty liver, coronary artery disease, osteoporosis, polycystic ovary syndromes, etc.
Type:
Grant
Filed:
September 19, 2008
Date of Patent:
December 13, 2011
Assignee:
Hanall Pharmaceutical Company, Ltd.
Inventors:
Sung Wuk Kim, Sung Soo Jun, Young Gwan Jo, Ja Seong Koo, Young Woong Kim, Byoung Ha Kim, Duck Kim
Abstract: A method for the production of N-aryl carbamates (urethanes) and N-aryl isocyanates is described in which aromatic nitro compounds are subjected to a reductive carbonylation in the presence of carbon monoxide and organic compounds carrying hydroxyl groups, wherein the carbonylation is carried out in the presence of metal complex catalysts, for which anionic N,O chelate ligands of the general type [M(N˜O)?2] and [M(O˜N˜N˜O)2?] containing a bi- or trivalent transition metal of the groups 5 to 11 are used.
Abstract: A process for the preparation of N-isobutyl-N-(2-hydroxy-3-amino-4-phenylbutyl)-p-nitrobenzenesulfonylamide derivatives in which a (1-benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid derivative is reacted with a p-nitrophenylsulfonyl halide to provide the desired product in a high yield and degree of purity.
Type:
Grant
Filed:
April 25, 2008
Date of Patent:
December 13, 2011
Assignee:
Tibotec Pharmaceuticals Ltd.
Inventors:
Hartmut Burghard Zinser, Peter Hermann Hölzle
Abstract: An improvement of the methanol carbonylation process for manufacturing acetic acid is disclosed. Specifically disclosed is a method for reducing the formation of alkyl iodides and C3-8 carboxylic acids by removing permanganate reducing compounds (“PRC's”) from the light phase of the condensed light ends overhead stream, including (a) distilling the light phase to yield a PRC enriched overhead stream; and (b) extracting the third overhead stream with water in at least two consecutive stages and separating therefrom one or more aqueous streams containing PRC?s.
Type:
Grant
Filed:
April 20, 2007
Date of Patent:
December 13, 2011
Assignee:
Celanese International Corporation
Inventors:
Mark O. Scates, David A. Trueba, Raymond J. Zinobile
Abstract: Described herein are compounds that are antagonists of PGD2 receptors. Also described are pharmaceutical compositions that include the compounds described herein, and methods of using such antagonists of PGD2 receptors, alone or in combination with other compounds, for treating respiratory, cardiovascular, and other PGD2-dependent or PGD2-mediated conditions or diseases.
Type:
Grant
Filed:
July 2, 2009
Date of Patent:
December 6, 2011
Assignee:
Panmira Pharmaceuticals, LLC
Inventors:
John Howard Hutchinson, Thomas Jon Seiders, Bowei Wang, Jeannie M. Arruda, Brian Andrew Stearns
Abstract: (R) and (S) 2-Aryl-propionic acids, and pharmaceutical compositions that contain them, are useful in inhibiting chemotactic activation of neutrophils (PMN leukocytes) induced by the interaction of Interleukin-8 (IL-8) with CXCR1 and CXCR2 membrane receptors. The acids are used for the prevention and treatment of pathologies deriving from said activation. In particular, the (R) enantiomers of said acids are lacking cyclo-oxygenase inhibition activity and are particularly useful in the treatment of neutrofil-dependent pathologies such as psoriasis, ulcerative colitis, melanoma, chronic obstructive pulmonary disease (COPD), bollous pemphigo, rheumatoid arthritis, idiopathic fibrosis, glomerulonephritis and in the prevention and treatment of damages caused by ischemia and reperfusion.
Type:
Grant
Filed:
November 19, 2002
Date of Patent:
November 22, 2011
Assignee:
Dompe PHA.R.MA S.p.A.
Inventors:
Marcello Allegretti, Riccardo Bertini, Cinzia Bizzarri, Maria Candida Cesta, Francesco Colotta