Acridines (including Hydrogenated) Patents (Class 546/102)
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Patent number: 7973030Abstract: A pharmaceutical useful as a therapeutic agent and a preventive agent for hyperlipemia, and a pharmaceutical useful as a therapeutic agent and a preventive agent for hepatic disorders associated with cholestasis, particularly, primary biliary cirrhosis and primary sclerosing cholangitis, and a pharmaceutical useful as a therapeutic agent and a preventive agent for obesity, fatty liver and steatohepatitis are provided.Type: GrantFiled: February 25, 2005Date of Patent: July 5, 2011Assignee: Asahi Kasei Pharma CorporationInventors: Takehiko Sasahara, Mitsunobu Mohri, Ken-Ichi Kasahara
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Patent number: 7939185Abstract: A fused polycyclic compounds is represented by the general formula (I): wherein X1 to X18 each represent, independently of one another, a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.Type: GrantFiled: November 21, 2008Date of Patent: May 10, 2011Assignee: Canon Kabushiki KaishaInventors: Naoki Yamada, Minako Nakasu, Satoshi Igawa, Masashi Hashimoto
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Publication number: 20110077221Abstract: This invention provides nuclear hormone receptor binding compounds, compositions comprising the same and methods of uses thereof in treating a variety of diseases or conditions in a subject, including, inter-alia, prostate cancer and/or diseases or disorders of bone and muscle.Type: ApplicationFiled: July 19, 2007Publication date: March 31, 2011Inventors: James T. Dalton, Duane D. Miller, Igor Rakov, Casey Bohl, Michael L. Mohler
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Patent number: 7910754Abstract: A compound of the formula wherein R1, R2, R3, R4, R5, R6, R?, R?, Y, CA+, and A? each, independently of the others are as defined herein.Type: GrantFiled: December 17, 2008Date of Patent: March 22, 2011Assignee: Xerox CorporationInventor: Jeffrey H. Banning
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Publication number: 20110061723Abstract: The present invention pertains to an electrode layer comprising a porous film made of oxide semiconductor fine particles sensitized with certain methin dyes. Moreover the present invention pertains to a photoelectric conversion device comprising said electrode layer, a dye sensitized solar cell comprising said photoelectric conversion device and to novel methin dyes.Type: ApplicationFiled: February 26, 2009Publication date: March 17, 2011Applicant: BASF SEInventors: Kazuhiko Kunimoto, Hiroshi Yamamoto, Shinji Nakamichi, Ryuichi Takahashi, Junichi Tanabe
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Patent number: 7888509Abstract: One aspect of the invention relates to 1,8-diarylnaphthalene compounds. In certain embodiments, a compound of the invention is an N-oxide of a 1,8-diarylnaphthalene. In certain embodiments, the aryl group is an optionally substituted acridyl group. In certain embodiments, a compound of the invention is a single steroisomer. In certain embodiments, a compound of the invention is a single enantiomer. Another aspect of the present invention relates to a method of detecting the presence of an analyte in a sample by monitoring the fluorescence of a compound of the invention in a sample. In certain embodiments, the analyte is a metal ion. Another aspect of the present invention relates to a method of determining the enantiomeric purity of an analyte by monitoring the fluorescence of a compound of the invention in the presence of the analyte. In certain embodiments, the analyte is a compound that is capable of hydrogen bonding.Type: GrantFiled: November 1, 2004Date of Patent: February 15, 2011Assignee: Georgetown UniversityInventors: Christian Wolf, Xuefeng Mei
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Publication number: 20110031484Abstract: A condensed-cyclic compound represented by Formula 1 and an organic light emitting diode including the same:Type: ApplicationFiled: August 9, 2010Publication date: February 10, 2011Applicant: Samsung Mobile Display Co., Ltd.Inventors: Kwan-Hee Lee, Mi-Kyung Kim, Seung-Gak Yang
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Publication number: 20110003992Abstract: A quaternary nitrogen-containing corrosion inhibitor of formula wherein is an aromatic, nitrogen-containing ring of 5 to 14 ring atoms, optionally containing an additional N, O or S ring atom and optionally substituted with one or more alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, amino, aminoalkyl, alkoxy, hydroxylalkyl, or cyano groups, or a mixture thereof; Y is a group of formula —OC(O)R1 or —C(O)R1; L is C1-C10 alkyl, C2-C10 alkenyl or a group of formula —CH2CH(OR2)CH2—; R1 is C8-C20 alkyl or C8-C20 alkenyl; R2 is H or —C(O)R1; R3 and R4 are independently selected from H, alkyl, alkenyl, amino, alkoxy, hydroxylalkyl and cyano; and X is Br, Cl or I is particularly useful for inhibiting corrosion in oil and gas field applications.Type: ApplicationFiled: September 15, 2010Publication date: January 6, 2011Inventor: Laxmikant Tiwari
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Publication number: 20100317031Abstract: New chemiluminescent compounds, stable in aqueous buffers, for use in biological assaying include acridane-based compounds and 1,2-dioxetanes. Among the new acridane-based compounds are water-soluble acridanes, enhancer coupled acridanes, bis and tris-acridanes as well as acridane-1,2-dioxetanes. Among the new 1,2-dioxetanes are electron deficient group-containing dioxetanes and tethered bis-1,2-dioxetanes. The 1,2-dioxetanes are useful as substrates for various enzymes. The acridanes can be admixed with an oxidizing agent an aqueous buffer and, optionally, a stabilizer to form a substrate or reagent formulation useful for assaying, inter alia, HRP.Type: ApplicationFiled: August 23, 2010Publication date: December 16, 2010Inventors: Brij Pal Giri, Dinesh Dagli, Pritam Singh
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Patent number: 7847125Abstract: A compound having the formula: R1 and R2 together with the carbon atoms to which they are bonded are joined together to form a C3-C30 ring. The C3-C30 ring may be substituted with one or more substituents or unsubstituted. The C3-C30 ring may contain one or more heteroatoms. The C3-C30 ring may be saturated, partially unsaturated, or fully unsaturated.Type: GrantFiled: November 16, 2007Date of Patent: December 7, 2010Assignee: Chemtura CorporationInventors: Qinggao Ma, Cyril Migdal
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Patent number: 7824928Abstract: In accordance with the present invention, it has been discovered that introduction of hydrophilic sulfoalkyl substituents and/or hydrophilic linkers derived from homocysteic acid, cysteic acid, glycine peptides, tetraethylene oxide, and the like, offset the hydrophobicity of the acridinium ring system to produce a more soluble label which can be attached to an antibody at higher loading before precipitation and aggregation problems are encountered. Additional compounds described herein contain linkers derived from short peptides and tetraethylene oxide which increase aqueous solubility due to hydrogen bonding with water molecules. The present invention also embraces reagents for multiple acridinium labeling for signal amplification composed of a peptide bearing several acridinium esters with sulfonate groups at regularly spaced intervals for increased solubility. The invention also embraces assays employing the above-described compounds.Type: GrantFiled: November 7, 2007Date of Patent: November 2, 2010Assignee: Quest Diagnostics Investments IncorporatedInventors: Ramon Evangelista, Martha Garrity
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Publication number: 20100256380Abstract: A method is provided for N-alkylation of acridine compounds, typically with a 1,3-propane sultone alkylating reagent, in ionic liquid solvents to provide the corresponding acridinium compounds in high yield.Type: ApplicationFiled: November 18, 2008Publication date: October 7, 2010Applicant: Siemens Healthcare Diagnostics Inc.Inventors: Anand Natrajan, David Wen
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Patent number: 7785904Abstract: The present invention relates to hydrophilic, high quantum yield acridinium compounds. It has been discovered that the placement of electron-donating groups in the acridinium ring system increases the amount of light that is emitted by the corresponding acridinium compound when its chemiluminescence is triggered by alkaline peroxide. More specifically, it has been found that the placement of one or two hydrophilic, alkoxy groups at the C-2 and/or C-7 position of the acridinium ring system of acridinium compounds increases their quantum yield and enhances the aqueous solubility of these compounds. The present hydrophilic, high quantum yield, acridinium compounds are useful chemiluminescent labels for improving the sensitivity of immunoassays.Type: GrantFiled: June 19, 2007Date of Patent: August 31, 2010Assignee: Siemens Healthcare Diagnostics Inc.Inventors: Anand Natrajan, Qingping Jiang, David Sharpe, James Costello
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Patent number: 7781628Abstract: A fluorene-based derivative having a specific structure and an organic electroluminescence device in which an organic thin film layer comprising a single layer or plural layers including at least a light emitting layer is sandwiched between a cathode and an anode, wherein at least one layer of the organic thin film layers described above comprises the above fluorene-based derivative having a specific structure in the form of a single component or a mixed component. The organic electroluminescence device has a high luminous efficiency, and the fluorene-based derivative materializes the same.Type: GrantFiled: July 24, 2008Date of Patent: August 24, 2010Assignee: Idemitsu Kosan Co., Ltd.Inventors: Mitsunori Ito, Hiroshi Yamamoto, Satoshi Hachiya, Hisayuki Kawamura
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Patent number: 7781229Abstract: New chemiluminescent compounds, stable in aqueous buffers, for use in biological assaying include acridanebased compounds and (1,2)-dioxetanes. Among the new acridanebased compounds are water-soluble acridanes, enhancer coupled acridanes, bis and trisacridanes as well as acridane-(1,2)-dioxetanes. Among the new (1,2)-dioxetanes are electron deficient group-containing dioxetanes and tethered bis-1,2-dioxetanes. The (1,2)-dioxetanes are useful as substrates for various enzymes. The acridanes can be admixed with an oxidizing agent. An aqueous buffer and, optionally, a stabilizer to form a substrate or reagent formulation useful for assaying, inter alia, HRP.Type: GrantFiled: April 14, 2005Date of Patent: August 24, 2010Assignee: Michigan Diagnostics, LLCInventors: Brij Pal Giri, Dinesh Dagli, Pritam Singh
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Patent number: 7781588Abstract: Acridian monomers and polymers are described, as well as their use in organic electronic devices, and materials and methods for fabrication of the same.Type: GrantFiled: December 16, 2005Date of Patent: August 24, 2010Assignee: E.I. du Pont de Nemours and CompanyInventors: Hailiang Wang, Zhensheng Zhang
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Publication number: 20100171417Abstract: Provided is a charge transport material represented by the following general formula (1) or (2). In the foregoing general formulae, each of L1 and L2 independently represents a connecting group; each of R and RN independently represents a substituent; each of R1 and R2 independently represents a substituent, provided that R1 and R2 do not represent an aryl group at the same time; each A independently represents a carbon atom or a nitrogen atom; n represents an integer of 2 or more and not more than 10; and each m independently represents an integer.Type: ApplicationFiled: January 6, 2010Publication date: July 8, 2010Applicant: FUJIFILM CORPORATIONInventors: Tetsu KITAMURA, Satoshi SANO, Toshihiro ISE, Saki TAKADA
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Publication number: 20100099077Abstract: Chemiluminescent acridinium esters are provided which are fast light emitting and hydrolytically stable. The chemiluminescent acridinium esters are useful labels in assays for detecting or quantifying analytes.Type: ApplicationFiled: October 15, 2007Publication date: April 22, 2010Applicant: Siemens Healthcare Diagnostics Inc.Inventors: Anand Natrajan, Qingping Jiang, David Sharpe
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Publication number: 20100032658Abstract: Provided are novel organic electroluminescent compounds and organic electroluminescent devices comprising the same as electroluminescent material. Specifically, the organic electroluminescent compounds according to the invention are characterized in that they are represented by Chemical Formula (1): wherein, L is selected from the following structures. The organic electroluminescent compounds according to the invention exhibit high luminous efficiency in blue color and excellent life property as a material, so that an OLED having very good operation life can be prepared therefrom.Type: ApplicationFiled: July 13, 2009Publication date: February 11, 2010Applicant: Gracel Display Inc.Inventors: Hyo Jung Lee, Young Jun Cho, Hyuck Joo Kwon, Bong Ok Kim, Sung Min Kim, Seung Soo Yoon
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Publication number: 20100019658Abstract: Organic compounds and organic electroluminescence devices employing the same are provided. The organic compound has a chemical structure represented as follows: wherein, R1 and R2 are independent and can be aryl, heteroaryl, cycloalkyl, hetero-cycloalkyl, or a cycloaliphatic group, or R1 and R2 link together with the carbon atoms to which they are attached to form a fused aryl, heteroaryl, cycloalkyl, hetero-cycloalkyl, or a cycloaliphatic group, and R3, R4, and R5 are independent and can be H, C1-8 alkyl, C1-8 alkoxy, C1-8 halo-alkyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, or a cycloaliphatic group.Type: ApplicationFiled: December 19, 2008Publication date: January 28, 2010Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTEInventors: Chi-Jen LIN, Heh-Lung HUANG, Jin-Sheng LIN, Chien-Hong CHENG, Mei-Rurng TSENG
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Publication number: 20090318627Abstract: Acridinium-functionalized solid-phase supports and methods for making acridinium-functionalized solid-phase supports are disclosed. The acridinium-functionalized solid-phase supports comprise a solid phase support linked to a chemiluminescent substituted acridinium compound through a linker group covalently attached to the nitrogen atom of the acridinium nucleus and the solid phase support as exemplified in FIG. 1.Type: ApplicationFiled: February 6, 2007Publication date: December 24, 2009Applicant: Siemens Healthcare Diagnostics Inc.Inventors: Anand Natrajan, David Sharpe, Jim Costello, Qingping Jiang
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Patent number: 7579468Abstract: Disclosed are compositions which modulate the interaction with nerve growth factor and precursors thereof with neurotrophic receptors. Also disclosed are methods of using the compositions of the invention, including methods of administration.Type: GrantFiled: September 14, 2006Date of Patent: August 25, 2009Assignee: PainCeptor Pharma CorporationInventors: Kazimierz Babinski, Rahul Vohra, Xilin Cui, Daniel Scott Auld, Nachhattarpal Gill
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Patent number: 7579448Abstract: A method for purifying a desired heterologous polypeptide from microbial fermentation broth or homogenate in which it is produced and solubilized is described. This method involves adding to the broth or homogenate an effective amount of a solution of 6,9-diamino-2-ethoxyacridine lactate (ethacridine lactate) to precipitate host cell impurities under conditions wherein the majority of polypeptide remains soluble, and separating the desired polypeptide from the broth or homogenate. The broth or homogenate containing the ethacridine lactate and polypeptide is also disclosed.Type: GrantFiled: December 12, 2006Date of Patent: August 25, 2009Assignee: Genentech, Inc.Inventors: Philip M. Lester, Josefine Persson
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Publication number: 20090189518Abstract: A fused polycyclic compounds is represented by the general formula (I): wherein X1 to X18 each represent, independently of one another, a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aralkyl group, a substituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.Type: ApplicationFiled: November 21, 2008Publication date: July 30, 2009Applicant: CANON KABUSHIKI KAISHAInventors: Naoki Yamada, Minako Nakasu, Satoshi Igawa, Masashi Hashimoto
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Publication number: 20090192146Abstract: The present invention provides substituted di-, tri-, tetra- and penta-sulfide compounds and compositions, and methods of using the same for the treatment and/or prevention of a cell proliferative disorder. The present invention also provides methods for preparing trisulfide compounds and compositions.Type: ApplicationFiled: February 9, 2009Publication date: July 30, 2009Applicant: ACEA BIOSCIENCES, INC.Inventors: Xiao XU, Haoyun An, Xiaobo Wang
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Publication number: 20090181943Abstract: This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula compounds of the Formula (I) and N-oxides, hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof, and racemic and scalemic mixtures, diastereomers and enantiomers thereof, wherein groups L, M, X and Y are as defined herein.Type: ApplicationFiled: April 9, 2008Publication date: July 16, 2009Applicant: METHYLGENE INC.Inventors: Pierre Tessier, Silvana Leit, David Smil, Robert Deziel, Alain Ajamian, Yves Andre Chantigny, Celia Dominguez
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Publication number: 20090131290Abstract: A compound having the formula: R1 and R2 together with the carbon atoms to which they are bonded are joined together to form a C3-C30 ring. The C3-C30 ring may be substituted with one or more substituents or unsubstituted. The C3-C30 ring may contain one or more heteroatoms. The C3-C30 ring may be saturated, partially unsaturated, or fully unsaturated.Type: ApplicationFiled: November 16, 2007Publication date: May 21, 2009Inventors: Qinggao Ma, Cyril Migdal
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Publication number: 20090121623Abstract: A condensed polycyclic compound is represented by the following Formula [1]: wherein in Formula [1], R1 to R16 each represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a substituted amino group, an aryl group that may optionally have a substituent group, or a heterocyclic group that may optionally have a substituent group, provided that at least one of R1, R2, R7 and R8 is an aryl group that may optionally have a substituent group, or a heterocyclic group that may optionally have a substituent group.Type: ApplicationFiled: October 30, 2008Publication date: May 14, 2009Applicant: CANON KABUSHIKI KAISHAInventors: Masashi Hashimoto, Satoshi Igawa, Naoki Yamada, Takayuki Horiuchi
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Publication number: 20090093062Abstract: The present teachings generally relate to fluorescent dyes, linkable forms of fluorescent dyes, energy transfer dyes, reagents labeled with fluorescent dyes and uses thereof.Type: ApplicationFiled: December 17, 2007Publication date: April 9, 2009Applicant: Applera CorporationInventors: Ronald J. Graham, Ruiming Zou, Krishna G. Upadhya, Scott C. Benson
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Patent number: 7511064Abstract: The present invention relates to derivatives of 4-(Thio- or Selenoxanthene-9-ylidene)-piperidine or acridine and pharmaceutically acceptable salts thereof, use of these compounds as a medicament and for the manufacture of a medicament for treatment of a disease state which can be alleviated by treatment with a 5-HT2B antagonist.Type: GrantFiled: April 19, 2006Date of Patent: March 31, 2009Assignee: Biofrontera Bioscience GmbHInventors: Hermann Lubbert, Christoph Ullmer, Emile Bellott, Mark Froimowitz, Douglas Gordon
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Patent number: 7485737Abstract: A compound of the formula wherein R1, R2, R3, R4, R5, R6, R?, R?, Y, CA+, and A? each, independently of the others are as defined herein.Type: GrantFiled: February 6, 2007Date of Patent: February 3, 2009Assignee: Xerox CorporationInventor: Jeffrey H. Banning
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Publication number: 20080308770Abstract: A quaternary nitrogen-containing corrosion inhibitor of formula wherein is an aromatic, nitrogen-containing ring of 5 to 14 ring atoms, optionally containing an additional N, O or S ring atom and optionally substituted with one or more alkyl, alkenyl, aryl, arylalkyl, cycloalkyl, amino, aminoalkyl, alkoxy, hydroxylalkyl, or cyano groups, or a mixture thereof, Y is a group of formula —OC(O)R1 or —C(O)R1; L is C1-C10 alkyl, C2-C10 alkenyl or a group of formula CH2CH(OR2)CH2—; R1 is C8-C20 alkyl or C8-C20 alkenyl; R2 is H or C(O)R1; R3 and R4 are independently selected from H, alkyl, alkenyl, amino, alkoxy, hydroxylalkyl and cyano; and X is Br, Cl or I is particularly useful for inhibiting corrosion in oil and gas field applications.Type: ApplicationFiled: June 14, 2007Publication date: December 18, 2008Inventor: Laxmikant Tiwari
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Patent number: 7459284Abstract: A chemiluminescent substrate of a hydrolytic enzyme having the following general Formula I is disclosed, as follows: Lumi-M-P??Formula I where “Lumi” is a chemiluminescent moiety capable of producing light (a) by itself, (b) with MP attached and (c) with M attached. Examples of Lumi include chemiluminescent acridinium compounds, benzacridinium compounds, quinolinium compounds, isoquinolinium compounds, phenanthridinium compounds, and lucigenin compounds, spiroacridan compounds, luminol compounds and isoluminol compounds. M is a multivalent heteroatom having at least one lone pair of electrons selected from oxygen, nitrogen and sulfur, directly attached to the light emitting moiety of Lumi at one end and to P at the other end. P is a group that can be readily removed by hydrolytic enzymes. An enzymatic reaction utilizing the above compound is the following: where HE is a hydrolytic enzyme. Lumi-M is a chemiluminescent product having physical and/or chemical properties different from those of Lumi-M-P.Type: GrantFiled: June 5, 2006Date of Patent: December 2, 2008Assignee: Siemens Healthcare Diagnostics Inc.Inventors: Qingping Jiang, Anand Natrajan, David Sharpe, Wen-Jee Wong, Say-Jong Law
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Publication number: 20080185555Abstract: Acene-based compounds that can be used to prepare n-type semiconductor materials are provided with processes for preparing the same. Composites and electronic devices including n-type semiconductor materials prepared from these compounds also are provided.Type: ApplicationFiled: November 19, 2007Publication date: August 7, 2008Inventors: Antonio Facchetti, Tobin J. Marks, Zhiming M. Wang
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Publication number: 20080152950Abstract: An anthracene derivative and an organic electroluminescent device using the same are provided. More specifically, provided are an anthracene derivative represented by Formula 1: wherein each R1 is aryl; and each R2 is independently C6-C20 aryl or C3-C19 heteroaryl, which are unsubstituted or substituted with one or more substituents selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, cyano, C1-C10 alkylamino, C1-C10 alkylsilyl, halogen, C6-C10 aryl, C6-C10 aryloxy, C6-C10 arylamino, C6-C10 arylsilyl, C3-C19 heteroaryl and hydrogen; and an organic electroluminescent device using the same. The present invention can provide an organic electroluminescent device having excellent power and luminance efficiencies in conjunction with a long service life.Type: ApplicationFiled: November 30, 2007Publication date: June 26, 2008Applicant: SFC CO., LTD.Inventors: Jong-Tae JE, Sug-Kwang Hwang, Sung-Hoon Kim, Seung-Hyuck Choi, Seon-Keun Yoo
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Patent number: 7388017Abstract: The present invention relates to compounds, methods and pharmaceutical compositions for inhibiting proteases, particularly serine proteases, and more particularly HCV NS3 proteases. The compounds, and the compositions and methods that utilize them, can be used, either alone or in combination to inhibit viruses, particularly HCV virus.Type: GrantFiled: June 27, 2003Date of Patent: June 17, 2008Assignee: Vertex Pharmaceuticals IncorporatedInventors: Roger D Tung, Scott L Harbeson, David D Deininger, Mark A Murcko, Govinda R Bhisetti, Luc J Farmer
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Patent number: 7332354Abstract: The present invention relates to a chemical compound comprising a light emitting moiety precursor and a precursor of a leaving group, bound to each other by an amide or by an ester bond and characterized in that the leaving group precursor upon oxidation is converted into the leaving group. The invention also relates to compounds additionally comprising a coupling group to the use of such compounds for labeling of biomolecules and more generally to the use of such compounds in chemiluminescence detection procedures.Type: GrantFiled: May 28, 2002Date of Patent: February 19, 2008Assignee: Roche Diagnostics Operations, Inc.Inventors: Dieter Heindl, Rupert Herrmann, Hans-Peter Josel, Erasmus Huber, Ursula Klause
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Patent number: 7319041Abstract: Chemiluminescent acridinium compounds are used in homogeneous assays to determine the concentration of an analyte in a sample without strong acid or strong base treatment. The chemiluminescent acridinium compounds include acridinium esters with electron donating functional groups at the C2 and/or C7 position on the acridinium nucleus to inhibit pseudo-base formation, or acridinium sulfonamides with or without electron donating functional groups at the C2 and/or C7 position on the acridinium nucleus.Type: GrantFiled: September 27, 2002Date of Patent: January 15, 2008Assignee: Siemens Medical Solutions DiagnosticInventors: Anand Natrajan, Todd Sells, Hartmut Schroeder, Guohan Yang, David Sharpe, Qingping Jiang, Hana Lukinsky, Say-Jong Law
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Patent number: 7309615Abstract: The present invention relates to hydrophilic, high quantum yield acridinium compounds. It has been discovered that the placement of electron-donating groups in the acridinium ring system increases the amount of light that is emitted by the corresponding acridinium compound when its chemiluminescence is triggered by alkaline peroxide. More specifically, it has been found that the placement of one or two hydrophilic, alkoxy groups at the C-2 and/or C-7 position of the acridinium ring system of acridinium compounds increases their quantum yield and enhances the aqueous solubility of these compounds. The present hydrophilic, high quantum yield, acridinium compounds are useful chemiluminescent labels for improving the sensitivity of immunoassays.Type: GrantFiled: June 2, 2005Date of Patent: December 18, 2007Assignee: Siemens Medical Solutions DiagnosticInventors: Anand Natrajan, Qingping Jiang, David Sharpe, James Costello
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Patent number: 7300930Abstract: The present invention pertains to acridone and acridine compounds of formula (I), wherein either: (a) K is ?O, L is —H, alpha is a single bond, beta is a double bond, gamma is a single bond (acridones); or, (b) K is a 9-substituent, L is absent, alpha is a double bond, beta is a single bond, gamma is a double bond (acridines); and wherein: J1 is a 2- or 3-substituent; J2 is a 6- or 7-substituent; J1 and J2 are each independently a group of the formula —NHCO(CH2)nNR1R2, wherein: n is an integer from 1 to 5; and, R1 and R2 are independently hydrogen, C1-7alkyl, C3-20heterocyclyl, or C5-20aryl, or R1 and R2, taken together with the nitrogen atom to which they are attached, form a heterocyclic ring having from 3 to 8 ring atoms; and wherein, when K is a 9-substituent, K is a group of the formula —N(RN)Q, wherein: RN is an amino substituent and is hydrogen, C1-7alkyl, C3-20heterocyclyl, or C5-20aryl; and, Q is C1-7alkyl, C3-20heterocyclyl, or C5-20aryl, and is optionally substituted; and pharmaceutically acceptablType: GrantFiled: June 22, 2005Date of Patent: November 27, 2007Assignee: Cancer Research Technology LimitedInventors: Stephen Neidle, Richard John Harrison, Lloyd Royston Kelland, Sharon Michele Gowan, Martin Anthony Read, Anthony Reszka
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Patent number: 7297555Abstract: In accordance with the present invention, it has been discovered that introduction of hydrophilic sulfoalkyl substituents and/or hydrophilic linkers derived from homocysteic acid, cysteic acid, glycine peptides, tetraethylene oxide, and the like, offset the hydrophobicity of the acridinium ring system to produce a more soluble label which can be attached to an antibody at higher loading before precipitation and aggregation problems are encountered. Additional compounds described herein contain linkers derived from short peptides and tetraethylene oxide which increase aqueous solubility due to hydrogen bonding with water molecules. The present invention also embraces reagents for multiple acridinium labeling for signal amplification composed of a peptide bearing several acridinium esters with sulfonate groups at regularly spaced intervals for increased solubility. The invention also embraces assays employing the above-described compounds.Type: GrantFiled: July 14, 2005Date of Patent: November 20, 2007Assignee: Quest Diagnostics Investments IncorporatedInventors: Ramon Evangelista, Martha Garrity
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Publication number: 20070191606Abstract: The present invention provides novel 2,2-bis(4-hydroxyphenyl)-alkyl onium salts as illustrated by 2,2-bis(4-hydroxyphenyl)-tridecyl(1,2-dimethylimidazolium)bromide and a process for preparation thereof by hydroxyalkylating acetoacetate to the corresponding hyroxyalkylacetoacetate, dealkoxycarbonylating the hydroxyalkyl acetoacetate to ?-hydroxyalkan-2-one and contacting the ?-hydroxyalkan-2-one with phenol in the presence of an acidic catalyst to give 2,2-bis(4-hydroxyphenyl)alkanol, brominating the 2,2-bis(4-hydroxyphenyl)alkanol to 2,2-bis(4-hydroxyphenyl)alkyl bromide, quaternizing 1,2-dimethylimidazole with the 2,2-bis(4-hydroxyphenyl)alkyl bromide to 2,2-bis(4-hydroxyphenyl)alkyl(1,2-dimethylimidazolium)bromide. The products can be used as reactive modifiers for layered phyllosilicates that can be used in the preparation of polymer-nanocomposites, wherein the said polymers are prepared from 2,2-bis(4-hydroxyphenyl)propane as one of the reacting monomers.Type: ApplicationFiled: October 13, 2006Publication date: August 16, 2007Applicant: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCHInventors: Shroff Rama Mallikarjuna, Swaminathan Sivaram
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Patent number: 7256292Abstract: The present teachings generally relate to fluorescent dyes, linkable forms of fluorescent dyes, energy transfer dyes, reagents labeled with fluorescent dyes and uses thereof.Type: GrantFiled: September 16, 2005Date of Patent: August 14, 2007Assignee: Applera CorporationInventors: Ronald J. Graham, Ruiming Zou, Krishna G. Upadhya, Scott C. Benson
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Patent number: 7223865Abstract: The present invention relates to novel chromogenic substrates which are used to detect aminopeptidase activity in microorganisms or to determine whether at least one bacterium belongs to the Gram-positive group or to the Gram-negative group according to the color thereof. The invention also relates to culture media containing such substrates, to the use of the substrates or media for the detection of aminopeptidase activities and/or the differentiation of Gram-positive bacteria from Gram-negative bacteria and to methods of use. The aforementioned novel substrates have the formula below: in which: R1 is nothing or an alkyl, allyl or aryl group, R2 consists of at least one amino acid, preferably alanine, R3, R4, R5 and R6 consist, independently of one another, of H— or —O-alkyl, preferably —O—CH3, R7 consists of H, O—CH3, alkyl or halogen, R8 consists of H or Cl, and n is an integer corresponding to 0 or 1. The invention is particularly suitable for use in the field of diagnostics.Type: GrantFiled: January 26, 2004Date of Patent: May 29, 2007Assignee: BiomerieuxInventors: Arthur James, Annette Rigby
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Patent number: 7205311Abstract: This invention pertains to certain acridone and acridine compounds of the formula which inhibit telomerase, regulate cell proliferation, etc., and/or treat cancer, proliferative conditions, etc.Type: GrantFiled: January 14, 2003Date of Patent: April 17, 2007Assignee: Cancer Research Technology LimitedInventors: Stephen Neidle, Richard John Harrison, Lloyd Royston Kelland, Sharon Michele Gowan, Martin Anthony Read, Anthony Reszka
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Patent number: 7186568Abstract: Methods are disclosed for producing electrochemiluminescence by electrochemically oxidizing an acridan compound at an electrode in the presence of a peroxide. Maintaining a sufficiently positive potential results in continuous oxidation of the acridan compound to an acridinium compound which reacts with peroxide to produce the luminescence. Light emission can be reversibly and repeatedly cycled on and off by sweeping the potential between two values. The acridan compounds can be provided with a labeling group for linking to an analyte or analyte binding partner. The present electrochemiluminescent reaction can find use in assay methods for detecting analytes by immunoassays and nucleic acid assays.Type: GrantFiled: June 26, 2001Date of Patent: March 6, 2007Assignee: Lumigen Inc.Inventors: Hashem Akhavan-Tafti, Robert Wilson, David Jorge Schiffrin
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Patent number: 7160896Abstract: The present invention pertains to acridone and acridine compounds of formula (I), wherein either: (a) K is ?O, L is —H, alpha single bond, beta is a double bond, gamma is a single bond (acridones); or, (b) K is a 9-substituent, L is absent, alpha is a double bond, beta is a single bond, gamma is a double bond (acridines); and wherein: J1 is a 2- or 3-substituent; J2 is a 6- or 7-substituent; J1 and J2 are each independently a group of the formula —NHCO(CH2)nNR1R2, wherein: n is an integer from 1 to 5; and, R1 and R2 are independently hydrogen, C1-7alkyl, C3-20heterocyclyl, or C5-20aryl, or R1 and R2, taken together with the nitrogen atom to which they are attached, form a heterocyclic ring having from 3 to 8 ring atoms; and wherein, when K is a 9-substituent, K is a group of the formula —N(RN)Q, wherein: RN is an amino substituent and is hydrogen, C1-7alkyl, C3-20heterocyclyl, or C5-20aryl; and, Q is C1-7alkyl, C3-20heterocyclyl, or C5-20aryl, and is optionally substituted; and pharmaceutically acceptable salType: GrantFiled: July 6, 2001Date of Patent: January 9, 2007Assignee: Cancer Research Technology LimitedInventors: Stephen Neidle, Richard John Harrison, Lloyd Royston Kelland, Sharon Michele Gowan, Martin Anthony Read, Anthony Reskza
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Patent number: 7160732Abstract: The present invention is directed, in part, to fluorescein-based ligands for detection of metal ions, and methods of making and using the same.Type: GrantFiled: July 9, 2001Date of Patent: January 9, 2007Assignee: Massachusetts Institute of TechnologyInventors: Stephen J. Lippard, Shawn Burdette, Scott Hilderbrand, Roger Y. Tsien, Grant K. Walkup
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Patent number: 7148069Abstract: The present invention provides a method for the analysis of a compound with amino group (e.g., an amino acid or peptide) contained in a sample and convenient manner with a high sensitivity. The compound with amino group in a sample containing the compound with amino group is labeled with a specific carbamate compound such as p-trimethylammonium anilyl-N-hydroxysuccinimidyl carbamate iodide to enhance the selectivity and sensitivity. The present invention is preferably used in conjunction with mass spectrometry such as MS/MS method to facilitate quantitative analysis. The present invention further provides labeling reagents for mass spectrometry.Type: GrantFiled: August 16, 2004Date of Patent: December 12, 2006Assignee: Ajinomoto Co., Inc.Inventors: Hiroshi Miyano, Akihisa Yahashi, Kazutaka Shimbo, Masakazu Nakazawa, Kazuo Hirayama
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Patent number: 7122671Abstract: A compound for use as a chemiluminescent label in immunoassay comprises an aryl acridinium ester linked to an N-succinimidyl moiety. The compound is conveniently linked to a monoclonal antibody or other protein and is used in a two-site immunoassay for the quantitation of an antigen of interest, by initiation of the luminescent reaction and subsequent measurement of the photonic emission of the immune complex formed during the immunological reaction.Type: GrantFiled: May 31, 1995Date of Patent: October 17, 2006Assignee: University College Cardiff Consultants LimitedInventors: Anthony Keith Campbell, James Stuart Woodhead, Ian Weeks