Plural Benzene Rings Bonded Directly To The Same Carbon Patents (Class 568/809)
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Publication number: 20140024657Abstract: The invention features a series of heterocyclic derivatives that inhibit tumor necrosis factor alpha (TNF-?) induced necroptosis. The heterocyclic compounds of the invention are described by Formulas (I)-(VIII) and by Compounds (1)-(7), (13)-(26), (27)-(33), (48)-(57), and (58)-(70). These necrostatins are shown to inhibit TNF-? induced necroptosis in FADD-deficient variant of human Jurkat T cells. The invention further features pharmaceutical compositions featuring necrostatins. The compounds and compositions of the invention may also be used to treat disorders where necroptosis is likely to play a substantial role.Type: ApplicationFiled: September 20, 2013Publication date: January 23, 2014Applicant: President and Fellows of Harvard CollegeInventors: Junying YUAN, Emily S. Hsu
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Patent number: 8227643Abstract: This invention relates to bis- and tris-dihydroxyaryl compounds and their methylenedioxy analogs and pharmaceutically acceptable salts and their use in the modulation of Sirtuin 1 (Sirt1) and there use in neuroprotection for subject suffering from neurodegenerative diseases such as Alzheimer's disease, Huntington's disease, Amyotrophic lateral sclerosis, frontotemporal dementia, Parkinson's disease, including Parkinson's plus diseases such as multiple system atrophy, progressive supranuclear palsy, corticobasal degeneration and dementia with Lewy bodies, and in the manufacture of medicaments for such Sirt1 modulation and neuroprotection.Type: GrantFiled: January 12, 2010Date of Patent: July 24, 2012Assignee: ProteoTech, Inc.Inventors: Alan D. Snow, Qubai Hu, Judy A. Cam
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Patent number: 8227371Abstract: This invention relates to a metathesis catalyst comprising (i) a Group 8 metal hydride-dihydrogen complex represented by the formula: wherein M is a Group 8 metal; X is an anionic ligand; and L1 and L2 are neutral donor ligands; and (ii) a ligand exchange agent represented by the formula J-Y, wherein J is selected from the group consisting of hydrogen, a C1 to C30 hydrocarbyl, and a C1 to C30 substituted hydrocarbyl; and Y is selected from the group consisting of halides, alkoxides, aryloxides, and alkyl sulfonates.Type: GrantFiled: September 24, 2010Date of Patent: July 24, 2012Assignee: ExxonMobil Chemical Patents Inc.Inventors: Matthew W. Holtcamp, Matthew S. Bedoya, Laughlin G. McCullough
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Publication number: 20120142934Abstract: A method for synthesis of secondary alcohols is provided for pharmaceutical secondary alcohol by addition of organoboronic acids with aldehydes in presence of the cobalt ion and bidentate ligands as the catalyst. In addition, an enantioselective synthesis method for secondary alcohols is also herein provided in the present invention. The present invention has advantages in using less expensive cobalt ion and commercially available chiral ligands as the catalyst, wide scope of organoboronic acids and aldehydes compatible with this catalytic reaction and achieving excellent yields and/or enantiomeric excess.Type: ApplicationFiled: March 10, 2011Publication date: June 7, 2012Inventors: Chien-Hong CHENG, Jaganathan Karthikeyan, Pang-Chi Huang
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Publication number: 20120122889Abstract: The invention features a series of heterocyclic derivatives that inhibit tumor necrosis factor alpha (TNF-?) induced necroptosis. The heterocyclic compounds of the invention are described by Formulas (I)-(VIII) and by Compounds (I)-(I), (13)-(26), (27)-(33), (48)-(57), and (58)-(70). These necrostatins are shown to inhibit TNF-? induced necroptosis in FADD-deficient variant of human Jurkat T cells. The invention further features pharmaceutical compositions featuring necrostatins. The compounds and compositions of the invention may also be used to treat disorders where necroptosis is likely to play a substantial role.Type: ApplicationFiled: December 23, 2009Publication date: May 17, 2012Applicant: President and Fellows of Harvard CollegeInventors: Junying Yuan, Emily S. Hsu
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Publication number: 20120088938Abstract: Disclosed is a method for producing an optically active alcohol including reacting a titanium compound, an aromatic magnesium compound and a carbonyl compound in the presence of an optically active biphenol compound having a predetermined structure and an ether compound having a predetermined structure.Type: ApplicationFiled: March 26, 2010Publication date: April 12, 2012Applicants: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH, MITSUI CHEMICALS, INC.Inventors: Manabu Wadamoto, Kazuhiko Yoshinaga, Takushi Nagata, Seayad Abdul Majeed, Ramalingam Balamurugan, Chai Christina L. L.
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Publication number: 20110077392Abstract: A method of crystallization is provided. The method includes providing a solution comprising a solute dissolved in a first solvent. The method includes providing a dispersion comprising a plurality of nanoparticles in a second solvent. The first solvent and the second solvent are mutually miscible. The method includes combining the solution and the dispersion to form a mixture. The nanoparticles remain dispersed in the mixture and the solute remains dissolved in the mixture at or below a saturation concentration. The method includes cooling the mixture such that the solute exceeds the saturation concentration forming crystals in the presence of the dispersed nanoparticles. The method includes separating the crystals from the mixture, wherein the nanoparticles remain dispersed in the mixture.Type: ApplicationFiled: June 26, 2009Publication date: March 31, 2011Inventors: Jimmie R. Baran, JR., William J. Hunt
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Patent number: 7807856Abstract: A process for producing a 2-benzylphenol compound represented by the following formula (2): wherein, R1, R2, R3 and R4 may be the same or different and are each independently hydrogen atom, alkyl group or the like; and R5, R6, R7, R8 and R9 are the same or different and are each independently hydrogen atom, alkyl group or the like, the process including reacting, in the presence of a dehydrogenating agent, a benzylidenecyclohexanone compound represented by the following formula (1): wherein, R1, R2, R3, R4, R5, R6, R7, R8 and R9 have the same definitions as given above.Type: GrantFiled: November 7, 2005Date of Patent: October 5, 2010Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Kentaro Kawazoe, Yasuo Yoshida
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Patent number: 7718831Abstract: Method of asymmetrically hydrosilylating substrates using catalysts having a ligand of the compound of the formula (I) wherein R is optionally substituted alkyl, cycloalkyl, aryl or heteroaryl; R? is hydrogen, optionally substituted lower alkyl; and R? is hydrogen, halogen, optionally substituted alkyl, hydroxy, amino (e.g., primary, secondary or tertiary), alkenyl; or an enantiomer thereof; or an enantiomeric mixture thereof with a transition metal. Particularly suitable reactions include the asymmetric hydrosilylation of ketones.Type: GrantFiled: February 16, 2006Date of Patent: May 18, 2010Assignee: The Hong Kong Polytechnic UniversityInventors: Albert S Chan, Jianxin Ji, Jing Wu
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Patent number: 7714170Abstract: Bis- and tris-dihydroxyaryl compounds and their methylenedioxy analogs and pharmaceutically acceptable esters, pharmaceutical compositions containing them, and their use in the treatment of amyloid diseases, especially A? amyloidosis, such as observed in Alzheimer's disease, use in the reduction of A? peptide in vivo, use in modulating APP processing, and use in modulating the activity of APP secretase.Type: GrantFiled: December 8, 2008Date of Patent: May 11, 2010Assignee: Proteotech, Inc.Inventors: Alan D. Snow, Qubai Hu, Judy A. Cam
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Patent number: 7622613Abstract: The present invention relates to a thiol compound represented by formula (1): wherein R1, R2 and n have the same meanings as in the specification, method for producing the compound, and to a photosensitive composition and a black matrix resist composition using the same which have high sensitivity and excellent property of retaining a line width in fine line patterns at the time of alkaline development, that is, being excellent in development latitude.Type: GrantFiled: October 25, 2005Date of Patent: November 24, 2009Assignee: Showa Denko K.K.Inventors: Hirotoshi Kamata, Mina Onishi, Katsumi Murofushi
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Patent number: 7601876Abstract: Bis- and tris-dihydroxyaryl compounds and their methylenedioxy analogs and pharmaceutically acceptable esters, their synthesis, pharmaceutical compositions containing them, and their use in the treatment of amyloid diseases, especially A? amyloidosis, such as observed in Alzheimer's disease, IAPP amyloidosis, such as observed in type 2 diabetes, AA/SAA amyloidosis, such as observed in systemic AA amyloidosis and synucleinopathies, such as observed in Parkinson's disease, and the manufacture of medicaments for such treatment.Type: GrantFiled: March 5, 2007Date of Patent: October 13, 2009Assignee: Proteotech, Inc.Inventors: Alan D. Snow, Beth P. Nguyen, Gerardo M. Castillo, Virginia J. Sanders, Thomas P. Lake, Lesley Larsen, Rex T. Weavers, Stephen D. Lorimer, David S. Larsen, David L. Coffen, Charlotte Coffen, legal representative
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Patent number: 7592487Abstract: The invention relates to the compounds of formula: (I) which are as defined in the specification. Their use as chiral ligands in catalytic aryl transfer reactions to aromatic aldehydes is also described.Type: GrantFiled: March 10, 2005Date of Patent: September 22, 2009Assignee: The Hong Kong Polytechnic UniversityInventors: Albert Sun-Chi Chan, Jianxin Ji
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Publication number: 20090143519Abstract: The present invention relates to a composition for obtaining artificial stone materials, which composition includes a compound selected from the group comprising benzopinacol and at least one derivative thereof. The present invention also relates to a mixture for obtaining an artificial stone material, including a resin compound and the above mentioned composition in a percentage ranging from 0.1 to 10% by weight with respect to the resin compound.Type: ApplicationFiled: June 3, 2008Publication date: June 4, 2009Applicant: AROS S.R.L.Inventors: Guglielmo CATEL, Ruggero FERRARIO, Giuseppe TESTA
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Publication number: 20080300430Abstract: The present disclosure relates to a process for the reduction of compounds comprising one or more carbon-oxygen (C?O) double bonds, to provide the corresponding alcohol, comprising contacting the compound with hydrogen gas at a pressure greater than 3 atm and a catalyst comprising an iridium aminodiphosphine complex.Type: ApplicationFiled: May 30, 2008Publication date: December 4, 2008Inventors: Kamaluddin Abdur-Rashid, Rongwei Guo, Xuanhua Chen, Wenli Jia
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Publication number: 20080045757Abstract: The invention relates to the compounds of formula: (I) which are as defined in the specification. Their use as chiral ligands in catalytic aryl transfer reactions to aromatic aldehydes is also described.Type: ApplicationFiled: March 10, 2005Publication date: February 21, 2008Inventors: Albert Sun-Chi Chan, Jianxin Ji
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Patent number: 7087798Abstract: A spirofluorenol such as 3?,9?-dimethoxy-5?-hydroxyspiro[(1H-cyclopent[d,e,f]phenanthrene)-1,7?-benzo[c]fluorene] is produced by protecting a hydroxyl group bonded to a particular fluorenone compound such as 3,9-dimethoxy-5-hydroxybenzo[c]fluorene-7-one with “a substituted silyl group in which the sum of carbon atoms of substituents bonded to a silicon atom is 5 to 12”, such as a t-butyldimethylsilyl group, then, reacting the fluorenone compound with a particular organometal compound such as 1-lithiophenanthrene so as to be transformed into a spiro form and, then, removing the protection therefrom. This method makes it possible to efficiently produce the spirofluorenol which is useful as a starting material for producing photochromic compounds.Type: GrantFiled: December 13, 2002Date of Patent: August 8, 2006Assignee: Tokuyama CorporationInventors: Hirohumi Shiigi, Noriyuki Fukada, Kenji Tanaka, Masao Yamaguchi
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Patent number: 7005525Abstract: Organometallic complexes are provided, which include a catalyst containing a transition metal, a ligand and a component having the formula GArF. ArF is an aromatic ring system selected from phenyl, naphthalenyl, anthracenyl, fluorenyl, or indenyl. The aromatic ring system has at least a substituent selected from fluorine, hydrogen, hydrocarbyl or fluorinated hydrocarbyl, G is substituted or unsubstituted (CH2)n or (CF2)n, wherein n is from 1 to 30, wherein further one or more CH2 or CF2 groups are optionally replaced by NR, PR, SiR2, BR, O or S, or R is hydrocarbyl or substituted hydrocarbyl, GArF being covalently bonded to either said transition metal or said ligand of said catalyst, thereby rendering said cationic organometallic complex liquid.Type: GrantFiled: December 9, 2003Date of Patent: February 28, 2006Assignee: Brookhaven Science Associates, LLCInventors: Vladimir K. Dioumaev, R. Morris Bullock
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Publication number: 20040230066Abstract: Citalopram can be industrially and economically produced and at a high yield by reacting a compound of the following formula [VI] with 3-(dimethylamino)propyl chloride in the presence of at least one of N,N,N′,N′-tetramethylethylenediamine and 1,3-dimethyl-2-imidazolidinone and a condensing agent. The compound of the following formula [III], which is a key compound for the production of citalopram, can be easily produced by subjecting the compound of the following formula [II] to reduction and cyclization.Type: ApplicationFiled: June 14, 2004Publication date: November 18, 2004Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Ikemoto, Wei-Guo Gao, Masami Igi
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Publication number: 20040121985Abstract: Farnesyl diphosphate analogs, specifically the 3-substituted alcohol precursors of the diphosphate analogs, 3-allylfarnesol and 3-vinylfarnesol, are potent inhibitors of mammalian protein fanesyltransferase (FTase). 3-allylgeranylgeraniol is a highly specific cellular inhibitor of protein geranylgeranylation (GGTase I). Furthermore, these compounds are able to efficiently block the anchorage-dependent growth of ras transformed cells. While 3-allylfarnesol inhibits protein farnesylation in situ, 3-vinylfarnesol instead leads to the abnormal prenylation of proteins with the 3-vinylfarnesyl group. In a similar manner, treatment with 3-allylgeranylgeraniol inhibits protein geranylgeranylation while 3-vinylgeranylgeraniol restores protein geranylgeranylation in cells.Type: ApplicationFiled: June 10, 2003Publication date: June 24, 2004Inventor: Richard A. Gibbs
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Patent number: 6737531Abstract: A compound is provided including an organometallic complex represented by the formula I: [CpM(CO)2(NHC)Lk]+A− I wherein M is an atom of molybdenum or tangsten, Cp is substituted or unsubstituted cyclopentadienyl radical represented by the formula [C5Q1Q2Q3Q4Q5], wherein Q1 to Q5 are independently selected from the group consisting of H radical, C1-20 hydrocarbyl radical, substituted hydrocarbyl radical, halogen radical, halogen-substituted hydrocarbyl radical, —OR, —C(O)R′, —CO2R′, —SiR′3 and —NR′R″, wherein R′ and R″ are independently selected from the group consisting of H radical, C1-20 hydrocarbyl radical, halogen radical, and halogen-substituted hydrocarbyl radical, wherein said Q1 to Q5 radicals are optionally linked to each other to form a stable bridging group, NHC is any N-heterocyclic carbene ligand, L is either any neutral electron donor ligand, wherein k is a number from 0 to 1 or LType: GrantFiled: December 17, 2002Date of Patent: May 18, 2004Assignee: Brookhaven Science Associates, LLCInventors: Vladimir K. Dioumaev, R. Morris Bullock
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Patent number: 6646170Abstract: The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.Type: GrantFiled: April 26, 2002Date of Patent: November 11, 2003Assignee: Esperion Therapeutics, Inc.Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
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Patent number: 6613923Abstract: The present invention is a process for the catalytic hydrogenation of ketones and aldehydes to alcohols at low temperatures and pressures using organometallic molybdenum and tungsten complexes and the catalyst used in the process. The reactants include a functional group which is selected from groups represented by the formulas R*(C═O)R′ and R*(C═O)H, wherein R* and R′ are selected from hydrogen or any alkyl or aryl group. The process includes reacting the organic compound in the presence of hydrogen and a catalyst to form a reaction mixture. The catalyst is prepared by reacting Ph3C+A− with a metal hydride. A− represents an anion and can be BF4−, PF6−, CF3SO3− or Bar′4−, wherein Ar′=3,5-bis(trifluoromethyl)phenyl.Type: GrantFiled: April 19, 2000Date of Patent: September 2, 2003Assignee: Brookhaven Science Associates, LLCInventors: R. Morris Bullock, Barbara F. M. Kimmich, Paul J. Fagan, Elisabeth Hauptman
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Patent number: 6610705Abstract: The invention relates to novel diaryl naphthyl methane compounds having general formula I as shown herein below, and said compounds useful in the treatment of esterogen related disease or syndrome, Pharmaceutical compositions comprising said novel methane derivatives, process for the preparation of the novel methane derivatives and methods for the treatment of esterogen related diseases or syndrome.Type: GrantFiled: March 31, 2000Date of Patent: August 26, 2003Assignee: Council of Scientific and Industrial ResearchInventors: Neeta Srivastava, Arvinder Grover
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Patent number: 6455739Abstract: 4-Fluorobenzaldehyde is produced by a commercially feasible process. The process comprises heating a mixture of fluorobenzene and a strong Lewis acid with dissolved hydrogen halide in an atmosphere of carbon monoxide at about 45 to about 100° C. and at a total pressure of about 150 psig up to the maximum pressure rating of the reactor. Formed is a reaction mass containing a Lewis acid complex of 4-fluorobenzaldehyde and at least a halobis(fluorophenyl)methane by-product. The complex is broken by quenching the reaction mass with a Lewis acid-solvating liquid to liberate 4-fluorobenzaldehyde. By-product halobis(fluorophenyl)methane is converted to di(fluorophenyl)methanol to avoid potential corrosion problems and formation of light sensitive color bodies in the recovered 4-fluorobenzaldehyde.Type: GrantFiled: September 7, 2001Date of Patent: September 24, 2002Assignee: Albemarle CorporationInventors: Steven G. Karseboom, Michael J. Turpie, Phillip R. Devrou, John F. Balhoff
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Publication number: 20020095051Abstract: Citalopram can be industrially and economically produced and at a high yield by reacting a compound of the following formula [VI] with 3-(dimethylamino)propyl chloride in the presence of at least one of N,N,N′,N′-tetramethylethylenediamine and 1,3-dimethyl-2-imidazolidinone and a condensing agent. The compound of the following formula [III], which is a key compound for the production of citalopram, can be easily produced by subjecting the compound of the following formula [II] to reduction and cyclization.Type: ApplicationFiled: February 28, 2002Publication date: July 18, 2002Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Ikemoto, Wei-Guo Gao, Nobuhiro Arai, Masami Igi
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Publication number: 20020062040Abstract: Citalopram can be industrially and economically produced and at a high yield by reacting a compound of the following formula [VI] with 3-(dimethylamino)propyl chloride in the presence of at least one of N,N,N′,N′-tetramethylethylenediamine and 1,3-dimethyl-2-imidazolidinone and a condensing agent. The compound of the following formula [III], which is a key compound for the production of citalopram, can be easily produced by subjecting the compound of the following formula [II] to reduction and cyclization.Type: ApplicationFiled: November 28, 2001Publication date: May 23, 2002Applicant: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Ikemoto, Wei-Guo Gao, Nobuhiro Arai, Masami Igi
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Patent number: 6342642Abstract: The present invention provides novel 1,4-diaryl-2-fluoro-1-buten-3-ol compounds of the structural formula I a method for the preparation of those formula I compounds, and the use of those formula I compounds in the preparation of 1,4-diaryl-2-fluoro-1,3-butadiene compounds of formula II and 1,4-diaryl-2-fluoro-2-butene compounds of formula IIIType: GrantFiled: August 13, 2001Date of Patent: January 29, 2002Assignee: BASF AktiengesellschaftInventors: Yulin Hu, David Allen Hunt
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Patent number: 6207865Abstract: A carbonyl compound or a mixture of two or more carbonyl compounds is catalytically hydrogenated in the presence of a Raney copper catalyst in the form of nuggets.Type: GrantFiled: January 11, 2000Date of Patent: March 27, 2001Assignee: BASF AktiengesellschaftInventors: Boris Breitscheidel, Marc Walter, Detlef Kratz, Gerhard Schulz, Manfred Sauerwald
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Patent number: 6127407Abstract: The present invention provides substituted 3,3-diphenyl indanone, indane and indole compounds, as well as analogues thereof, which are specific, potent and safe inhibitors of mammalian cell proliferation. The compounds can be used to inhibit mammalian cell proliferation in situ as a therapeutic approach towards the treatment or prevention of diseases characterized by abnormal cell proliferation, such as cancer.Type: GrantFiled: November 20, 1997Date of Patent: October 3, 2000Assignees: Ion Pharmaceuticals, Inc., President and Fellows of Harvard College, Children's Medical Center CorporationInventors: Carlo Brugnara, Jose Halperin, Rudolf Fluckiger, Emile M. Bellott, Jr., Richard John Lombardy, John J. Clifford, Ying-Duo Gao, Reem M. Haidar, Eugene W. Kelleher, Adel M. Moussa, Yesh P. Sachdeva, Minghua Sun, Heather N. Taft
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Patent number: 6124509Abstract: The present invention is a process for the catalytic hydrogenation of ketones and aldehydes to alcohols at low temperatures and pressures using organometallic molybdenum and tungsten complexes. The functional group is selected from groups represented by the formulas R(C.dbd.O)R' and R(C.dbd.O)H, wherein R and R' are selected from hydrogen or any alkyl or aryl group. The active catalyst for the process has the form: [CpM(CO).sub.2 (PR*.sub.3) L].sup.+ A.sup.-, where Cp=.eta..sup.5 -R.sup..tangle-solidup..sub.m C.sub.5 H.sub.5-m and R.sup..tangle-solidup. represents an alkyl group or a halogen (F, Cl, Br, I) or R.sup..tangle-solidup. =OR' (where R'=H, an alkyl group or an aryl group) or R.sup..tangle-solidup. =CO.sub.2 R' (where R'=H, an alkyl group or an aryl group) and m=0 to 5; M represents a molybdenum atom or a tungsten atom; R*.sub.3 represents three hydrocarbon groups selected from a cyclohexyl group (C.sub.6 H.sub.11), a methyl group (CH.sub.3), and a phenyl group (C.sub.6 H.sub.Type: GrantFiled: January 22, 1999Date of Patent: September 26, 2000Assignee: Brookhaven Science AssociatesInventors: Mark Voges, R. Morris Bullock
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Patent number: 6043272Abstract: The present invention provides substituted 3,3-diphenyl indanone, indane and indole compounds, as well as analogues thereof, which are specific, potent and safe inhibitors of mammalian cell proliferation. The compounds can be used to inhibit mammalian cell proliferation in situ as a therapeutic approach towards the treatment or prevention of diseases characterized by abnormal cell proliferation, such as cancer.Type: GrantFiled: November 20, 1997Date of Patent: March 28, 2000Assignees: Ion Pharmaceuticals, Inc., President and Fellows of Harvard College, Children's Medical Center CorporationInventors: Carlo Brugnara, Jose Halperin, Rudolf Fluckiger, Emile M. Bellott, Jr., Richard John Lombardy, John J. Clifford, Ying-Duo Gao, Reem M. Haidar, Eugene W. Kelleher, Adel M. Moussa, Yesh P. Sachdeva, Minghua Sun, Heather N. Taft
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Patent number: 6025531Abstract: A process for preparing an optically active alcohol by reacting a prochiral ketone corresponding to the optically active alcohol and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride; or obtained from the optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine and (2) a metal borohydride; and a process for preparing an optically active amine by reacting an oxime derivative and an acid with a mixture of (1) a boron-containing compound selected from the group consisting of i) a borane compound which is obtained from an optically active .beta.-aminoalcohol and a boron hydride, or obtained from said optically active .beta.-aminoalcohol, a metal borohydride and an acid and ii) an optically active oxazaborolidine, and (2) a metal borohydride.Type: GrantFiled: June 3, 1998Date of Patent: February 15, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Naoto Konya, Gohfu Suzukamo
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Patent number: 5830920Abstract: Compounds of the formula ##STR1## wherein n.sup.1 -n.sup.9 are each independently 0 or 1;m.sup.1 -m.sup.9 are each independently 0 or 1, but with the proviso that at least one of m.sup.1, m.sup.2 and m.sup.3, at least one of m.sup.4, m.sup.5 and m.sup.6 and, when present, at least one of m.sup.7, m.sup.8 and m.sup.9 is 1; and whereinX.sup.1 -X.sup.18 each independently is --O--, --CONR.sup.1,--NR.sup.1 CO-- or --NR.sup.1 --;R.sup.1 is hydrogen or lower alkyl;W is a benzene or s-triazine;Y.sup.1 -Y.sup.9 each independently is an aromatic ring systems;A.sup.1 -A.sup.3 each independently is a residue of a sugar alcohol devoid of the 1-hydroxy group or a derivative thereof, a residue of a sugar acid devoid of the 1-carboxy group or a derivative thereof or tris-(hydroxymethyl)-methyl;D is the di-residue of a sugar alcohol devoid of 2 hydroxy groups or a derivative thereof or the di-residue of a sugar dicarboxylic acid devoid of 2 carboxy group or a derivative thereof;Q.sup.1 -Q.sup.3 and Z.sup.Type: GrantFiled: April 26, 1996Date of Patent: November 3, 1998Assignee: Hoffmann-La Roche Inc.Inventors: Alexander Chucholowski, Jurgen Fingerle, Niggi Iberg, Hans Peter Marki, Rita Muller, Michael Pech, Marianne Rouge, Gerard Schmid, Thomas Tschopp, Hans Peter Wessel
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Patent number: 5792876Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.Type: GrantFiled: November 6, 1996Date of Patent: August 11, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
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Patent number: 5780692Abstract: A process for producing a benzhydrol compound (II) which comprises hydrogenating a benzophenone compound (I) in the presence of a hydrogenation catalyst consisting of a transition metal complex, a base and an optically active diamine compound: ##STR1## wherein R.sup.1 to R.sup.10 each represents H, OH, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkanoyl, etc., R.sup.2 and R.sup.3, and R.sup.8 and R.sup.9 may form --CH.dbd.CH--CH.dbd.CH--, or any two of R.sup.1 to R.sup.9 adjacent to each other may be bonded to thereby form --OCH.sub.2 O-- or --(CH.sub.2).sub.3 --. By using this process, optically active benzhydrol compounds which have a high purity and are useful as, for example, intermediates in the synthesis of drugs can be produced by simple procedures.Type: GrantFiled: December 24, 1996Date of Patent: July 14, 1998Assignee: Takasago International CorporationInventors: Minzo Sakaguchi, Takashi Imai, Takashi Miura, Tetsuro Yamazaki
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Patent number: 5750784Abstract: The present invention provides a method of effecting vasodilation, comprising:administering to a warm blooded animal in need of such treatment, an effective amount of a (1,5-inter) aryl prostaglandin derivative represented by the Formula I ##STR1## wherein n is 0 or an integer of from 1 to 6, R is selected from the group of radicals represented by the formulae:CO.sub.2 R', CONR'.sub.2, CH.sub.2 OR' and SO.sub.2 NR'.sub.2 'wherein R' is hydrogen or a lower alkyl radical having from one to six carbon atoms; R" is hydrogen or an acyl radical having the formula (CO)R'" wherein R'" is a saturated or unsaturated acyclic hydrocarbon radical having from 1 to about 10 carbon atoms, or --(CH.sub.2).sub.m R"" wherein m is 0 or an integer of from 1 to 6 and R"" is an aliphatic ring having from 3 to 7 carbon atoms or an aryl group, e.g. phenyl, or a heteroaryl group, e.g.Type: GrantFiled: February 18, 1997Date of Patent: May 12, 1998Assignee: AllerganInventors: June Chen, Robert M. Burk, David F. Woodward
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Patent number: 5681835Abstract: Prescribed herein are novel non-steroidal ligands for the estrogen receptor which possess tissue-dependent estrogenic and antiestrogenic activity as well as methods for making the same and their applications in treating a variety of disease states.Type: GrantFiled: April 25, 1994Date of Patent: October 28, 1997Assignee: Glaxo Wellcome Inc.Inventor: Timothy Mark Willson
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Patent number: 5426196Abstract: The present Invention includes synthetic steps and intermediates involved in the following reaction scheme a of converting compounds of Formula (II) to the diarylmethanes of Formula (I): ##STR1## wherein: Y is oxygen or sulfur;A, B, C, D, and E are carbon or 1, 2 or 3 of A, B, C, D, and E are independently nitrogen, and the others are carbon; andwhereinR.sup.1 through R.sup.10 are selected independently from the group consisting of: hydrogen, hydroxy, alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl alkyl, alkenyl, hydroxy alkyl, alkoxy alkyl, perhalo-alkyl, amino, nitro, nitrile, halo, carboxyl, sulfonyl, acyl, formyl, carbamoyl, trifluoromethyl, aminomethyl, azido, amido, hydrazino, aryl, aryloxy, heteroaryl, or aryl or heteroaryl, mono, di, or tri substituted with one or more hydrogen, hydroxy, alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.Type: GrantFiled: December 22, 1993Date of Patent: June 20, 1995Assignee: Glaxo Inc.Inventor: Francis G. Fang
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Patent number: 5395985Abstract: A compound represented by the general formula (I) and a separating agent comprising the same: ##STR1## wherein Ar and Ar' are each an aromatic group; and the positional relationship of the two substituents on the central benzene ring may be any of ortho, meta and para.The above compound is effective in the separation and purification of many compounds to and enables the provision of various compounds (such as intermediates of drugs) which are useful in the field of fine chemicals, particularly optically active substances, at high purities and in large amounts.Type: GrantFiled: March 4, 1994Date of Patent: March 7, 1995Assignee: Daicel Chemical Industries, Ltd.Inventor: Fumio Toda
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Patent number: 5393885Abstract: Compounds of the formula ##STR1## in which R.sub.1 is halogen, C.sub.1 -C.sub.3 alkyl, halo-C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, halo-C.sub.1 -C.sub.3 alkoxy or cyano and/or two substituents R.sub.1 which are bonded to adjacent C atoms of the phenyl ring together are --O--CH.sub.2 --O--; R.sub.2 is hydrogen, halogen or methyl;R.sub.3 is fluorine, chlorine, bromine or C.sub.1 -C.sub.3 alkyl; R.sub.4 is hydrogen or C.sub.1 -C.sub.3 alkyl;either R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, ##STR2## --COCO--R.sub.8,--CO--R.sub.9 or S(O).sub.m --N(R.sub.10)--COO--R.sub.11 andR.sub.6 is C.sub.1 -C.sub.6 alkyl, halo-C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkenyl, halo-C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.5 alkynyl, halo-C.sub.3 -C.sub.5 alkynyl, C.sub.1 -C.sub.3 alkoxy-C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.6 cycloalkyl, unsubstituted or substituted phenyl; or R.sub.5 and R.sub.6 together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; R.sub.7 is hydrogen, halogen or C.sub.1 -C.sub.3 alkyl; R.Type: GrantFiled: February 22, 1994Date of Patent: February 28, 1995Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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Patent number: 5227537Abstract: A method is described for the production of 6,12-dihydro-6-hydroxy-cannabidiol which is obtained by the reaction of olivetol and cis-p-menth-2-ene-1,8,-diol and the reaction thereof to yield trans-delta-9-tetrahydrocannabinol.Type: GrantFiled: January 8, 1992Date of Patent: July 13, 1993Assignee: Heinrich Mack Nachf.Inventors: Peter Stoss, Peter Merrath
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Patent number: 5196607Abstract: A novel multi-step process for preparing the (4S)-enantiomer of 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone in a highly-optically pure form is disclosed. The process involves (1) first reacting 3,4-dichlorocinnamyl chloride with L-(-)-ephedrine in a chlorinated lower hydrocarbon solvent to form the corresponding chiral N-methyl-N-(.beta.-hydroxy-.beta.-phenylisopropyl)-3-(3,4-dichlorophenyl)p ropenoamide; (2) then subjecting the chiral .alpha.,.beta.-unsaturated amide formed in the first step to a Grignard reaction with phenyl magnesium chloride or bromide, followed by hydrolysis, to effect a conjugate addition of the phenyl group and the hydrogen element to the aforesaid .alpha.,.beta.-unsaturated propenoamide and so selectively form the corresponding chiral N-methyl-N-(.beta.-hydroxy-.beta.Type: GrantFiled: February 14, 1992Date of Patent: March 23, 1993Assignee: Pfizer Inc.Inventor: George J. Quallich
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Patent number: 5144039Abstract: The process for producing an optically active alcohol of the present invention comprises allowing(A) an optically active amino alcohol represented by the general formula (I) ##STR1## (R.sup.1 is an aryl group, R.sup.2 is a lower alkyl group, R.sup.3 is a hydrogen atom or a lower alkyl group, and the carbon atoms having a mark * are each an asymmetric carbon atom) and an acid, or a salt of the optically active amino alcohol (I) and an acid,(B) a metal borohydride, and(C) at least one member selected from the group consisting of water, sulfides, cyclic ethers, ethers of mono alcohol to react witha prochiral ketone represented by the general formula (II) ##STR2## [R.sup.4 and R.sup.5 are different and each a lower alkyl group, an aryl group, an aralkyl group or a 2-substituted-1-triazoleethylene group represented by the general formula (III) ##STR3## (R.sup.6 is a halogen- or haloalkyl-substituted or unsubstituted phenyl group or a cycloalkyl group)].Type: GrantFiled: January 29, 1990Date of Patent: September 1, 1992Assignee: Sumitomo Electric Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Naoto Konya, Takaharu Ikeda
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Patent number: 5136114Abstract: The invention relates to a new process for the preparation of geminal diarylalkanes of the formula ##STR1## by Friedel-Crafts alkylation of aromatic compounds with specific aliphatic halogen compounds (addition compounds of CCl.sub.4 , to .alpha.-olefins), to new geminal diarylalkanes and the aralkyl compounds resulting as intermediates.Type: GrantFiled: April 30, 1990Date of Patent: August 4, 1992Assignee: Bayer AktiengesellschaftInventor: Dieter Arlt
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Patent number: 5120853Abstract: The optically active benzylamine derivatives of the present invention are very useful for use as the asymmetric ligand of an asymmetric reducing agent. By using the optically active amine-boron complex prepared from the compound of the present invention, optically active products can be obtained in a specifically high optical yield. Moreover, the separation and recovery of the reaction products and asymmetric ligand can be easily achieved.Type: GrantFiled: February 8, 1991Date of Patent: June 9, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Yoji Sakito
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Patent number: 5118878Abstract: A gram-negative, aerobic, motile, rod-shaped bacterium which is closely related to Chryseomonas luteola and Flavimonas oryzihabitans, has been found to catalyze the biodegradation and biotransformation of bisphenol alkanes, such as 2,2-bis(4-hydroxyphenyl)-propane or bisphenol A. A variety of bisphenol alkyl alcohols can be made by this procedure.Type: GrantFiled: April 26, 1991Date of Patent: June 2, 1992Assignee: General Electric CompanyInventors: John H. Lobos, Terry K. Leib, Tah-Mun Su
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Patent number: 5118881Abstract: The present invention provides for an improved practical process for producing DDTr-free p,p'-dicofol and its formulations substantially free of the practically inactive o-p'-dicofol comprising either directly recrystallizing technical dicofol from a suitable solvent such as acetic acid or alkanes, or alternatively preparing the p,p'-dicofol by the steps of (a) dehydrohalogenating technical DDT to give DDE; (b) chlorinating DDE to give Cl-DDT; and (c) hydrolyzing Cl-DDT to dicofol, wherein the technical DDT is initially recrystallized from a suitable solvent such as lower alkyl alcohols and then recrystallizing the ressulting p,p'-dicofol from a suitable solvent such as acetic acid or alkanes.Type: GrantFiled: November 8, 1990Date of Patent: June 2, 1992Assignee: Agan Chemical Manufacturers, Ltd.Inventors: Bernard Vaisbuch, Benjamin Shifman, Michael Pikarski
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Patent number: 5093516Abstract: An aromatic compound of the formula ##STR1## wherein n is 0 or 1,(1) when n is 1,R' represents hydrogen or C.sub.1 -C.sub.4 alkoxy,R" represents hydrogen, OH, C.sub.1 -C.sub.4 acyloxy, C.sub.1 -C.sub.4 alkoxy or amino,or R' and R" taken together form an oxo, methano or hydroxy-imino radical,R.sub.1 represents--CH.sub.2 OH or --COR.sub.10,R.sub.10 represents hydrogen, OR.sub.11 or ##STR2## R.sub.11 represents hydrogen, C.sub.1 -C.sub.20 alkyl, monohydroxyalkyl, polyhydroxy alkyl, aryl, aralkyl, the residue of a sugar or ##STR3## p is 1,2 or 3, r' and r" represent hydrogen, lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl, benzyl, the residue of an amino acid or the residue of an aminated sugar, of r' and r" taken together form a heterocycle,R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 represent hydrogen, OH, C.sub.1 -C.sub.12 alkyl, cycloalkyl, cycloalkenyl, phenyl or a radical of the formulas (i)--X--C.sub.6 H.sub.5, (ii)--X--R.sub.12 or (iii)--NHCOR.sub.13,X is --0--,--S--,--SO--,--SO.sub.Type: GrantFiled: April 3, 1987Date of Patent: March 3, 1992Assignee: L'OrealInventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle, Braham Shroot
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Patent number: 5081319Abstract: 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethanol is separated from a mixture comprising by way of the formation of an addition compound between 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethanol and a moderately electron donating compound, preferably selected from a group formed by dimethyl sulphoxide, cyclohexanone, isophoron, pyridine, 1,4-dioxane, acetic acid, acetonitrile and water.Type: GrantFiled: July 18, 1990Date of Patent: January 14, 1992Assignee: Sociedad Espanola de Desarrollos Quimicos S.A.Inventors: Jaime Palencia Adrubau, Jaume Castella Sola