Nitrogen Containing Patents (Class 568/423)
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Publication number: 20150148523Abstract: The invention provides compounds and methods, for example, to carry out organocatalytic Michael additions of aldehydes to cyclically constrained nitroethylene compounds catalyzed by a proline derivative to provide cyclically constrained ?-substituted-?-nitro-aldehydes. The reaction can be rendered enantioselective when a chiral pyrrolidine catalyst is used, allowing for Michael adducts in nearly optically pure form (e.g., 96 to >99% e.e.). The Michael adducts can bear a single substituent or dual substituents adjacent to the carbonyl. The Michael adducts can be efficiently converted to cyclically constrained protected ?-amino acid residues, which are essential for systematic conformational studies of ?-peptide foldamers. New methods are also provided to prepare other ?-amino acids and peptides. These new building blocks can be used to prepare foldamers, such as ?/?-peptide foldamers, that adopt specific helical conformations in solution and in the solid state.Type: ApplicationFiled: January 28, 2014Publication date: May 28, 2015Applicant: Wisconsin Alumni Research FoundationInventors: Samuel Helmer Gellman, Li Guo, Michael Giuliano
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Patent number: 8614358Abstract: The present invention relates to a process for preparing 2-methyl-3-(4-tert-butyl-phenyl)propanal with high para-isomer purity, and also to a process for preparing 4-tert-butylbenzaldehyde with high para-isomer purity.Type: GrantFiled: September 16, 2011Date of Patent: December 24, 2013Assignee: BASF SEInventors: Ulrich Griesbach, Jörg Botzem, Florian Stecker
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Patent number: 8569526Abstract: The invention relates to a method for carrying out an oxidation reaction for producing a product by heating a reaction medium containing a reactant and oxygen or an oxygen carrier in a reactor, wherein the reaction medium is brought into contact with a solid heating medium which may be heated by electromagnetic induction, which is surrounded by the reaction medium. The heating medium is heated by electromagnetic induction using an inductor, wherein an oxidation reaction is carried out on the first reactant to give a product and the product is separated from the heating medium. The inductor preferably generates an alternating field with a frequency in the range 1 to 100 kHz, preferably in the range 10 to 80 kHz and in particular up to 50 kHz.Type: GrantFiled: August 16, 2011Date of Patent: October 29, 2013Assignee: Henkel AG & Co. KGaAInventors: Carsten Friese, Andreas Kirschning, Sascha Volkan Ceylan
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Publication number: 20120296093Abstract: This application discloses a novel process for the preparation of himbacine analogs useful as thrombin receptor antagonists. The process is based in part on the use of a base-promoted dynamic epimerization of a chiral nitro center.Type: ApplicationFiled: July 31, 2012Publication date: November 22, 2012Inventors: George Wu, Anantha R. SUDHAKAR, Tao WANG, Ji XIE, Frank Xing CHEN, Marc POIRIER, Mingsheng HUANG, Vijay SABESAN, Daw-long KWOK, Jian CUI, Xiaojing YANG, Tiruvettipuram K. THIRUVENGADAM, Jing LIAO, Ilia A. Zavialov, Hoa N. NGUYEN, Ngiap Kie LIM
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Patent number: 8269039Abstract: The invention provides novel compounds and methods to carry out organocatalytic Michael additions of aldehydes to nitroethylene catalyzed by a proline derivative to provide ?-substituted-?-nitroaldehydes. The reaction can be rendered enantioselective when a chiral pyrrolidine catalyst is used, allowing for Michael adducts in nearly optically pure form (e.g., 96-99% e.e.). The Michael adducts can bear a single substituent or dual substituents adjacent to the carbonyl. The Michael adducts can be efficiently converted to protected ?2-amino acids, which are essential for systematic conformational studies of ?-peptide foldamers.Type: GrantFiled: March 23, 2009Date of Patent: September 18, 2012Assignee: Wisconsin Alumni Research FoundationInventors: Samuel Helmer Gellman, Yonggui Chi, Li Guo
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Publication number: 20110251392Abstract: This application discloses a novel process for the preparation of himbacine analogs useful as thrombin receptor antagonists. The process is based in part on the use of a base-promoted dynamic epimerization of a chiral nitro center.Type: ApplicationFiled: June 24, 2011Publication date: October 13, 2011Inventors: George Wu, Anantha R. Sudhakar, Mingsheng Huang, Tao Wang, Vijay Sabesan, Ji Xie, Frank Xing Chen, Marc Poirier, Daw-long Kwok, Jian Cui, Xiaojing Yang, Tiruvettipuram K. Thiruvengadam, Jing Liao, Ilia A. Zavialov, Hoa N. Nguyen, Ngiap Kie. Lim
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Publication number: 20100130749Abstract: The invention related to a novel process, novel process steps and novel intermediates useful in the synthesis of pharmaceutically active compounds, especially renin inhibitors, such as Aliskiren Inter alia the invention relates to a process for the manufacture of a compound of the formula I. or a salt thereof, wherein R1 as well as Act are as defined in the specification, and processes of manufacturing this compound as well as intermediates in this process.Type: ApplicationFiled: April 1, 2008Publication date: May 27, 2010Inventor: Gottfried Sedelmeier
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Publication number: 20090264676Abstract: The invention provides novel compounds and methods to carry out organocatalytic Michael additions of aldehydes to nitroethylene catalyzed by a proline derivative to provide ?-substituted-?-nitroaldehydes. The reaction can be rendered enantioselective when a chiral pyrrolidine catalyst is used, allowing for Michael adducts in nearly optically pure form (e.g., 96-99% e.e.). The Michael adducts can bear a single substituent or dual substituents adjacent to the carbonyl. The Michael adducts can be efficiently converted to protected ?2-amino acids, which are essential for systematic conformational studies of ?-peptide foldamers.Type: ApplicationFiled: March 23, 2009Publication date: October 22, 2009Applicant: WARF - Wisconsin Alumni Research FoundationInventors: Samuel Helmer Gellman, Yonggui Chi, Li Guo
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Patent number: 7270985Abstract: A process is disclosed to treat the protein hydrolysate, prepared conventionally from a proteinous source, with alkali metal hydride to obtain alcohol which is subsequently oxidized to obtain aldehyde under certain specified conditions, thereby converting large protein molecules into aldehyde based industrial products of much smaller molecular size.Type: GrantFiled: September 14, 2004Date of Patent: September 18, 2007Assignee: Council of Scientific & Industrial ResearchInventors: James Kanagaraj, Gopala Suseela Rajakumar, Sayeed Sadulla
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Patent number: 7115387Abstract: A process is disclosed to treat the protein hydrolysate, prepared conventionally from a proteinous source, with alkyl halide to obtain alcohol which is subsequently oxidized to obtain aldehyde under certain specified conditions, thereby converting large protein molecules into aldehyde based industrial products of much smaller molecular size.Type: GrantFiled: September 15, 2003Date of Patent: October 3, 2006Assignee: Council of Scientific & Industrial ResearchInventors: James Kanagaraj, Gopala Suseela Rajakumar, Sayeed Sadulla
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Patent number: 6949681Abstract: This invention provides compounds of the formula: wherein A and B are as defined; and Fmoc is 9-fluorenylmethoxycarbonyl. Such compounds are useful as intermediates for preparing glycopeptide derivatives which are useful as antibiotics.Type: GrantFiled: April 15, 2004Date of Patent: September 27, 2005Assignee: Theravance, Inc.Inventor: Martin S. Linsell
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Patent number: 6515137Abstract: Acid addition salts of imidazolidinones are provided as catalysts for transforming a functional group within a first reactant by reaction with a second reactant. Exemplary first reactants are &agr;,&bgr;-unsaturated carbonyl compounds such as &agr;,&bgr;-unsaturated ketones and &agr;,&bgr;-unsaturated aldehydes. Chiral imidazolidinone salts can be used to catalyze enantioselective reactions, such that a chiral product is obtained from a chiral or achiral starting material in enantiomerically pure form.Type: GrantFiled: July 30, 2001Date of Patent: February 4, 2003Assignee: The Regents of the University of CaliforniaInventors: David W. C. MacMillan, Kateri A. Ahrendt
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Patent number: 6509506Abstract: D- and L- &agr;-amino acids and D- and L-&agr;-amino aldehydes are synthesized from olefin substrates in two steps. The first step is a catalyzed asymmetric aminohydroxylation addition reaction to the olefin substrate. The addition reaction is catalyzed by osmium and is co-catalyzed by chiral ligands. The chiral ligands, in addition to being co-catalysts with the osmium, also serve to direct the addition reaction regioselectively and enantioselectively, divalent ligands are preferred over monovalent ligands because of their enhanced regio-and enantio-selectivity. As an oxidant nitrogen source for the addition reaction, either a carbamate or sulfonamide may be employed. If carbamate is employed as an oxidant nitrogen source, the resultant &bgr;-hydoxycarbamate is deprotected to yield the corresponding &bgr;-hydroxyamine. If sulfonamide is employed as an oxidant nitrogen source, the resultant &bgr;-hydroxysulfonamide is deprotected to yield the corresponding &bgr;-hydroxyamine.Type: GrantFiled: April 5, 1999Date of Patent: January 21, 2003Assignee: The Scripps Research InstituteInventors: K. Barry Sharpless, Guigen Li
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Patent number: 6486307Abstract: A method of producing glucosamine hydrochloride from chitin by grinding the chitin to a very fine size and digestion with concentrated hydrochloric acid. The glucosamine hydrochloride is decolorized with activated charcoal, washed with ethanol and assayed by pH titration with a base.Type: GrantFiled: August 23, 2001Date of Patent: November 26, 2002Assignee: Alberta Research Council Inc.Inventors: Neena Gandhi, James Kenneth Laidler
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Patent number: 6395916Abstract: One aspect of the present invention relates to novel, electron-rich bidentate ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.Type: GrantFiled: July 10, 1998Date of Patent: May 28, 2002Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, John P. Wolfe, David W. Old, Ken Kamikawa, Michael Palucki
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Patent number: 6291702Abstract: The present invention relates to chromotropic nitrone spin trapping agents, methods of making these agents, compositions comprising same, and methods of their use. In particular, azulenyl nitrones of the present invention are effective agents for trapping free radical species and find use as efficient antioxidants in physicochemical and biological systems. Accordingly, the invention also relates to spin adducts formed from the combination of azulenyl nitrones with free radicals. The compounds of the present invention are readily prepared from available starting materials and find further use in assays and in a number of diagnostic, prophylactic and therapeutic applications, including but not limited to the alleviation, modulation and inhibition of the negative effects of carbon-centered or oxygen-centered radical species and other products of oxidation. Moreover, the combination adducts may be colorimetrically detected and, optionally, isolated and characterized to obtain valuable information (e.g.Type: GrantFiled: February 8, 2000Date of Patent: September 18, 2001Assignee: Florida International UniversityInventor: David Alan Becker
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Patent number: 6197825Abstract: The present invention relates to chromotropic nitrone spin trapping agents, methods of making these agents, compositions comprising same, and methods of their use. In particular, azulenyl nitrones of the present invention are effective agents for trapping free radical species and find use as efficient antioxidants in physicochemical and biological systems. Accordingly, the invention also relates to spin adducts formed from the combination of azulenyl nitrones with free radicals. The compounds of the present invention are readily prepared from available starting materials and find further use in assays and in a number of diagnostic, prophylactic and therapeutic applications, including but not limited to the alleviation, modulation and inhibition of the negative effects of carbon-centered or oxygen-centered radical species and other products of oxidation. Moreover, the combination adducts may be calorimetrically detected and, optionally, isolated and characterized to obtain valuable information (e.g.Type: GrantFiled: May 28, 1998Date of Patent: March 6, 2001Assignee: Florida International UniversityInventor: David Alan Becker
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Patent number: 5659065Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, aromatic or heteroaromatic radical, a hydroxy group that is aliphatically, araliphatically or heteroarylaliphatically etherified or protected by a hydroxy-protecting group, or an aliphatically etherified mercapto group, andR.sub.2 is an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, araliphatic or heteroarylaliphatic radical, orR.sub.1 and R.sub.2 together form a divalent aliphatic radical,R.sub.3 is free or aliphatically, araliphatically or aromatically esterified carboxy, formyl or hydroxymethyl,R.sub.4 is hydrogen, an aliphatic or araliphatic radical or an amino-protecting group, andR.sub.5 is hydrogen or an aliphatic radical,and the salts thereof can be used as intermediates in the preparation of medicinal active ingredients.Type: GrantFiled: April 4, 1995Date of Patent: August 19, 1997Assignee: Novartis CorporationInventor: Richard Goschke
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Patent number: 5543560Abstract: A method for the hydrogenolytic reduction of peroxidic ozonolysis products to the corresponding carbonyl compounds in the presence of an inert organic diluting agent and in the presence of a monolith catalyst at hydrogen pressures of 0.01 to 2.0 MPa and at temperatures of -10.degree. to 150.degree. C., and a device for the catalytic hydrogenolysis of chemical compounds which yield uniform, new products by means of hydrogenolysis with hydrogen.Type: GrantFiled: March 11, 1994Date of Patent: August 6, 1996Assignee: Chemie Linz Gesellschaft m.b.H.Inventors: Stefan Pollhammer, Josef Scaller, Willibald Winetzhammer
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Patent number: 5530150Abstract: A phosphine compound represented by one of the formulas: ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a halogen atom or a lower alkyl group or taken together form a divalent hydrocarbon group; and R.sup.3 and R.sup.4, which may be the same or different, each represent a lower alkyl group, a phenyl group or a phenyl group substituted with a halogen atom, a lower alkyl group or a lower alkoxy group or taken together form a divalent hydrocarbon group, and wherein R.sup.6 and R.sup.6' which may be the same or different, each represent a hydrogen atom, a lower alkyl group or a lower alkoxy group; R.sup.5, R.sup.5', R.sup.11 and R.sup.11' which may be the same or different, each represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; or a pair of R.sup.5 and R.sup.6 or a pair of R.sup.5' and R.sup.6' may form a ring; R.sup.7 and R.sup.Type: GrantFiled: October 12, 1994Date of Patent: June 25, 1996Assignee: Takasago International CorporationInventors: Hidemasa Takaya, Nozomu Sakai, Kyoko Tamao, Satoshi Mano, Hidenori Kumobayashi, Tetsuo Tomita, Takao Saito, Kazuhiko Matsumura, Yasushi Kato, Noboru Sayo
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Patent number: 5489714Abstract: Described is a method of preparing dinitrobis(hydroxymethyl)benzene, useful as a photoreactive monomer, from a derivative of stilbene. Also disclosed is a novel dinitrocarbomethoxybenzaldehyde compound useful as an intermediate.Type: GrantFiled: May 22, 1995Date of Patent: February 6, 1996Assignee: PPG Industries, Inc.Inventors: Charles F. Kahle, II, Raphael O. Kollah, Gregory J. McCollum
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Patent number: 5449834Abstract: Described is a method of preparing dinitrobis(hydroxymethyl)benzene, useful as a photoreactive monomer, from a derivative of stilbene. Also disclosed is a novel dinitrocarbomethoxybenzaldehyde compound useful as an intermediate.Type: GrantFiled: July 13, 1994Date of Patent: September 12, 1995Assignee: PPG Industries, Inc.Inventors: Charles F. Kahle, II, Raphael O. Kollah, Gregory J. McCollum
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Patent number: 5329025Abstract: A new and practical method for synthesizing heterocyclic polyhydroxylated alkaloids using enzymatic aldol condensation and catalytic intramolecular reductive amination is disclosed.Type: GrantFiled: April 2, 1992Date of Patent: July 12, 1994Assignee: G. D. Searle & Co.Inventors: Chi-Huey Wong, Richard L. Pederson, Yi-Fong Wang
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Patent number: 5232915Abstract: 9.alpha.-Hydroxy-19,11.beta.-bridged steroids of general formula I ##STR1## are described. The more detailed meaning of A, B, R.sup.1, R.sup.2, G, Z, R.sup.4 --Y and R.sup.4' --Y' follows from the description. The steroids of general formula I have antigestagen and/or antiglucocorticoidal action and can be used for the production of pharmaceutical agents.Type: GrantFiled: January 14, 1992Date of Patent: August 3, 1993Assignee: Schering AktiengesellschaftInventors: Eckhard Ottow, Gunter Neef, Rudolf Wiechert, Walter Elger, Sybille Beier, Karl-Heinrich Fritzemeier
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Patent number: 5166373Abstract: The present invention provides novel acyclic terpenes of the formula: ##STR1## which are useful as intermediates for the industrially advantageous production of sarcophytol A.Type: GrantFiled: December 30, 1991Date of Patent: November 24, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5082976Abstract: Benzaldehydes of the formula ##STR1## can be obtained by reaction of substituted .beta.-amino-styrenes of the formula ##STR2## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.8, R.sup.9, R.sup.10, m, n and o have the scope of meaning indicated in the description, with oxygen in the presence of a Cu compound in the solution of an aprotic polar solvent at 0.degree.-120.degree. C.Type: GrantFiled: October 25, 1990Date of Patent: January 21, 1992Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Helmut Kraus
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Patent number: 4605749Abstract: There is provided a process for the production of aldehydes wherein an oric halide is reacted with carbon monoxide at a superatmospheric pressure in the presence of a hydrogen donor and in the presence of a base and of a catalyst in a solvent system.Catalysts of choice are transition metal catalysts. A preferred temperature range is from about 50.degree. to 150.degree. C.Type: GrantFiled: June 20, 1985Date of Patent: August 12, 1986Assignee: State of Israel, Prime Minister's Office, Atomic Energy CommissionInventors: Ouri Buchman, Ilan Pri-Bar
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Patent number: 4544765Abstract: Chloramphenicol derivatives are provided for use in the preparing of antigen conjugates for the production of antibodies specifically for chloramphenicol. Specifically, the aryl amino group is derivatized to introduce a non-oxocarbonyl group which is used for amide formation with an antigen. The conjugate is then injected into a vertebrate for production of antisera which is isolated in conventional ways and find particular use in competitive protein binding assays.Type: GrantFiled: November 30, 1984Date of Patent: October 1, 1985Assignee: Syra CompanyInventors: Pyare Khanna, Evan S. Snyder, Prithipal Singh
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Patent number: 4299985Abstract: This invention concerns the synthesis of linear alkyl primary amines from a-olefins via an oxoamination process comprising (a) hydrogen and carbon monoxide addition to olefinic substrates to obtain aldehyde-containing compounds in the presence of ligand-stabilized platinum(II) halide catalysts with Group IVB metal halide cocatalysts, and (b) reductive amination of said aldehydic intermediates in the presence of oxide-supported, nickel catalysts.Type: GrantFiled: December 16, 1980Date of Patent: November 10, 1981Assignee: Texaco Inc.Inventors: John F. Knifton, Philip H. Moss
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Patent number: 4219660Abstract: There are disclosed herein derivatives of bisfunctionalized compounds, wherein said compounds have been formed by the introduction of a nitro group and a hydroxyl group in the form of an ester into a conjugated diene molecule by treatment of said conjugated dienes with nitric acid in the presence of a carboxylic acid anhydride. The novel compounds produced by this process are useful as bactericides, fungicides and valuable organic synthesis intermediates.Type: GrantFiled: June 24, 1977Date of Patent: August 26, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Pius A. Wehrli
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Patent number: 4211727Abstract: Carboxylic acid halides are reduced to the corresponding aldehydes using zinc borohydride or cadmium borohydride as the reducing agent.Type: GrantFiled: March 15, 1979Date of Patent: July 8, 1980Assignee: Shell Oil CompanyInventors: Ian D. Entwistle, Robert A. W. Johnstone