Boron Containing Patents (Class 548/405)
-
Patent number: 6368395Abstract: The present invention is directed to methods of making subphthalocyanine compounds. The methods of the present invention may be used to produce known subphthalocyanine compounds, as well as, a new family of subphthalocyanine compounds. The methods of the present invention may employ environmentally-friendly solvents, which donate a hydrogen atom for use in the reaction mechanism. The methods of the present invention produce subphthalocyanine compounds at a yield of greater than about 50%, and even greater than about 94%. The present invention is further directed to subphthalocyanine compounds having improved lightfastness. The subphthalocyanine compounds may have a Subphth-Lightfastness Test Value of less than 15%.Type: GrantFiled: May 12, 2000Date of Patent: April 9, 2002Assignee: Kimberly-Clark Worldwide, Inc.Inventors: Ronald Sinclair Nohr, John G. MacDonald
-
Publication number: 20020038004Abstract: A reagent having the general formula of General Formula I: 1Type: ApplicationFiled: June 4, 2001Publication date: March 28, 2002Inventors: Mark L. Stolowitz, Guisheng Li, Jean P. Wiley
-
Patent number: 6352962Abstract: A lubricant additive obtained by heating an acidic phosphate ester and/or a phosphite ester (A) represented by the general formula (I): (wherein A represents H or OH, m is 0 or 1, when m is 0, A is OH, and when m is 1, A is H or OH, R1 and R2 each independently represent H, or a hydrocarbon group having 1 to 18 carbon atoms that may contain at least one O and S, both R1 and R2 are not simultaneously hydrogen atoms) and an imide-based dispersant containing boron (B) at a temperature of 120 to 150° C. for 5 hours or more, which can concurrently enhance excellent wear resistance, excellent scoring resistance and prolong surface fatigue life while keeping the balance of these properties at an optimum level.Type: GrantFiled: April 3, 2000Date of Patent: March 5, 2002Assignees: Idemitsu Kosan Co., Ltd., NSK Ltd.Inventors: Hitoshi Hata, Hiromichi Seiki, Hisashi Machida
-
Publication number: 20020015961Abstract: A hydrocarbyldithiomethyl-modified compound of the Formula:Type: ApplicationFiled: September 12, 2001Publication date: February 7, 2002Inventor: Marek Kwiatkowski
-
Patent number: 6337399Abstract: This invention relates to processes for producing a 7-isoindoline-quinolonecarboxylic acid derivative represented by the general formula [1] which is useful as an antibacterial agent, and an intermediate thereof: wherein R1 represents a hydrogen atom or a carboxyl-protecting group; R2 represents a substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl or heterocyclic group; R3 represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, alkoxy or alkylthio groups, nitro group, cyano group, acyl groups, protected or unprotected hydroxyl groups and protected or unprotected or substituted or unsubstituted amino groups; R4 represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy or alkylthio groups, protected or unprotected hydroxyl or imino groups, protected or unprotected or substituted or unsubstituted aminType: GrantFiled: April 26, 2000Date of Patent: January 8, 2002Assignee: Toyama Chemical Co., Ltd.Inventors: Minoru Yamada, Shoichi Hamamoto, Kazuya Hayashi, Kazuko Takaoka, Hiroko Matsukura, Minako Yotsuji, Kenji Yonezawa, Katsuji Ojima, Tamotsu Takamatsu, Kyoko Taya, Hirohiko Yamamoto, Taro Kiyoto, Hironori Kotsubo
-
Patent number: 6323039Abstract: The invention provides compositions and methods for monitoring subcellular compartments such as organelles by energy transfer techniques that do not require specific intermolecular affinity binding events between energy transfer donor and energy transfer acceptor molecules. Provided are methods for assaying cellular membrane potential, including mitochondrial membrane potential, by energy transfer methodologies including fluorescence resonance energy transfer (FRET). Diagnostic and drug screening assays are also provided.Type: GrantFiled: June 22, 1999Date of Patent: November 27, 2001Assignee: MitokorInventors: James A. Dykens, Gönül Veliçelebi, Soumitra S. Ghosh
-
Patent number: 6294680Abstract: A process has been provided to produce semi synthetic statins, as for instance simvastatin with a high yield, for another statin, preferably a naturally occurring statin, as for instance lovastatin. Also a number of novel intermediate compounds, prepared during said process, has been provided.Type: GrantFiled: January 5, 2000Date of Patent: September 25, 2001Assignee: Plus Chemicals, B.V.Inventors: Ton Rene Vries, Hans Wijnberg, Wijnand Sjourd Faber, Venetka Ivanova Kalkman-Agayn, Mieke Ivanova Sibeyn
-
Patent number: 6229019Abstract: A process for producing phosphinopyrrolidine compounds especially useful for preparing optically active compounds through asymmetric synthesis which is a simplified short process requiring neither a step necessitating a high-temperature and high-pressure reaction nor special equipment for production. A phosphino group is incorporated into a pyrrolidine compound in the presence of a boron compound, and the resultant pyrrolidine compound is further reacted while protecting the phosphorous atom, whereby a dicyclohexylphosphino group can be efficiently incorporated into the pyrrolidine nucleus in the 4-position. Thus, the target phosphinopyrrolidine compounds useful as ligands for asymmetric synthesis catalysts can be obtained through a significantly small number of steps without resort to troublesome steps such as the step of reducing a phenyl group at high temperature and high pressure.Type: GrantFiled: June 17, 1999Date of Patent: May 8, 2001Assignees: Fuji Yakuhin Kogyo Kabushiki KaishaInventors: Shin-ichi Nakamoto, Kazuo Achiwa
-
Patent number: 6146431Abstract: A polysuccinimide composition is prepared by reacting a mixture of an alkenyl or alkylsuccinic acid derivative, an unsaturated acidic reagent copolymer, and a polyamine under reactive conditions. The alkenyl or alkyl substituent of the alkenyl or alkylsuccinic acid derivative has a Mn of from 140 to 3000. The unsaturated acidic reagent copolymer has an average degree of polymerization of from 2 to 20, and is a copolymer of an unsaturated acidic reagent and an olefin having a Mn of at least 1000. The polyamine has at least three nitrogen atoms and has from 4 to 20 carbon atoms.Type: GrantFiled: December 23, 1999Date of Patent: November 14, 2000Assignee: Chevron Chemical Company LLCInventors: James J. Harrison, William R. Ruhe, Jr.
-
Patent number: 6124471Abstract: Reagents suitable for the modification of a bioactive species for the purpose of incorporating one or more phenyldiboronic acid (PDBA) moieties for subsequent conjugation to a different (or the same) bioactive species having one or more pendant boronic compound complexing moieties of the general formula of General Formula I, ##STR1## wherein group R is a reactive electrophilic or nucleophilic moiety suitable for reaction of the PDBA reagent with a bioactive species. Group Z is a spacer selected from a saturated or unsaturated chain up to about 0 to 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one intermediate amide or disulfide moiety, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length. Group Q is a linkage that includes one of amide, ether and thioether moieties.Type: GrantFiled: September 28, 1999Date of Patent: September 26, 2000Assignee: Prolinx, Inc.Inventors: Mark L. Stolowitz, Edward A. Kesicki, Kevin P. Lund, Karin A. Hughes
-
Patent number: 6106999Abstract: A visible light curable resin composition containing a photocurable resin, a photoreaction initiator and a photosensitizer having the formula (1). The composition has a very high sensitivity to a general-purpose visible light laser, so that a high-speed scanning exposure is possible by the laser, and an extremely fine high resolution can be obtained. In addition, the composition can be used for coating or printing under safelight irradiating conditions and under bright circumstantial conditions without any thickening of the composition, and hence the composition can exert excellent noticeable effects in points of safe operativity, operational efficiency and the stability of products. Formula (1) is as follows: ##STR1## wherein rings X.sub.1 and X.sub.2 are each an optionally substituted pyrrole ring; Y is H, CN, optionally substituted alkyl, aralkyl, aryl, heteroaryl or alkenyl group; and Z.sub.1 and Z.sub.Type: GrantFiled: August 10, 1998Date of Patent: August 22, 2000Assignees: Mitsui Chemicals, Kansai Paint Co., Ltd.Inventors: Akira Ogiso, Tsutami Misawa, Taizo Nishimoto, Hisashi Tsukahara, Keisuke Takuma, Kenichi Sugimoto, Takeshi Tsuda, Genji Imai, Hideo Kogure
-
Patent number: 6090950Abstract: Novel chiral boron and aluminum hydride complexes, compositions comprising the chiral hydride complexes, and methods for their synthesis and use are described. The novel chiral hydride complexes are of the formulas:MBH.sub.4-n-a (R*).sub.n (R').sub.a ;MBH.sub.2-b (R**) (R').sub.b ;MBH(R***);MBH(R*) (R");MAlH.sub.4-n-a (R*).sub.n (R').sub.a ;MAlH.sub.2-b (R**)(R').sub.b ;MAlH(R***); andMAlH(R*) (R"),whereinM is Na.sup.+, Li.sup.+ or K.sup.+ ;each R* is independently a monodentate chiral ligand;R** is a bidentate chiral ligand;R*** is a tridentate chiral ligand;R' is a monodentate achiral ligand;R" is a bidentate achiral ligand;n is 1-3;a is 0-2; andb is 0-1,with the proviso that n+a.ltoreq.3, and with the further proviso that when R** is S-BINOL, M is not Li.sup.+.Type: GrantFiled: August 23, 1996Date of Patent: July 18, 2000Assignee: Zeeland Chemicals, Inc.Inventor: Glenn L. Heise
-
Patent number: 6083903Abstract: Disclosed herein are boronic ester and acid compounds, their synthesis and uses. More specifically, disclosed herein is a method for reducing the rate of degradation of proteins in an animal comprising contacting cells of the animal with certain boronic ester and acid compounds.Type: GrantFiled: May 16, 1995Date of Patent: July 4, 2000Assignee: LeukoSite, Inc.Inventors: Julian Adams, Yu-Ting Ma, Ross Stein, Matthew Baevsky, Louis Grenier, Louis Plamondon
-
Patent number: 6066730Abstract: Disclosed herein is a method for reducing the rate of degradation of proteins in an animal comprising contacting cells of the animal with certain boronic ester and acid compounds. Also disclosed herein are novel boronic ester and acid compounds, their synthesis and uses.Type: GrantFiled: May 26, 1998Date of Patent: May 23, 2000Assignee: ProScript, Inc.Inventors: Julian Adams, Yu-Ting Ma, Ross Stein, Matthew Baevsky, Louis Grenier, Louis Plamondon
-
Patent number: 6060606Abstract: An optical recording medium having at least a recording layer and a reflective layer on a substrates, the said recording layer contains a dipyrromethene metal chelate compound obtained from a dipyrromethene compound represented by the general formula (1) and a metal ion: ##STR1## wherein R.sup.1 to R.sup.7 are defined in the specification.Type: GrantFiled: April 14, 1999Date of Patent: May 9, 2000Assignees: Mitsui Chemicals, Inc., Yamamoto Chemicals, Inc.Inventors: Tsutami Misawa, Kenichi Sugimoto, Taizo Nishimoto, Hisashi Tsukahara, Takeshi Tsuda, Keisuke Takuma, Hideki Umehara
-
Patent number: 6025370Abstract: The present invention relates to a quinolone-carboxylic acid derivative represented by the general formula [1], or its salt: ##STR1## Of the compounds of the present invention, preferable are compounds in which R.sup.2 represents a substituted or unsubstituted cycloalkyl group; R.sup.3 represents at least one member selected from the group consisting of a hydrogen atom, a halogen atom, a substituted or unsubstituted lower alkyl or lower alkoxy group, and a protected or unprotected hydroxyl or amino group; R.sup.4 represents a hydrogen atom or a substituted or unsubstituted lower alkyl group; each of R.sup.5 and R.sup.6 represents a hydrogen atom; and A represents C--Y in which Y represents a halogen atom, a lower alkyl or lower alkoxy group which may be substituted by one or more halogen atoms, or a protected or unprotected hydroxyl group.Type: GrantFiled: August 10, 1998Date of Patent: February 15, 2000Assignee: Toyama Chemical Co., Ltd.Inventors: Yozo Todo, Kazuya Hayashi, Masahiro Takahata, Yasuo Watanabe, Hirokazu Narita
-
Patent number: 6015776Abstract: A polysuccinimide composition is prepared by reacting a mixture of an alkenyl or alkylsuccinic acid derivative, an unsaturated acidic reagent copolymer, and a polyamine under reactive conditions. The alkenyl or alkyl substituent of the alkenyl or alkylsuccinic acid derivative has a Mn of from 140 to 3000. The unsaturated acidic reagent copolymer has an average degree of polymerization of from 2 to 20, and is a copolymer of an unsaturated acidic reagent and an olefin having a Mn of at least 1000. The polyamine has at least three nitrogen atoms and has from 4 to 20 carbon atoms.Type: GrantFiled: September 8, 1998Date of Patent: January 18, 2000Assignee: Chevron Chemical CompanyInventors: James J. Harrison, William R. Ruhe, Jr.
-
Patent number: 6005113Abstract: The invention relates to fluorescent dyes that are substituted or unsubstituted derivatives of 1-(isoindolyl)methylene-isoindole that are bound through both isoindole nitrogens to a boron difluoride moiety, forming a fluorescent dibenzopyrrometheneboron difluoride compound ##STR1## that is further substituted by bathochromic substituents that are aryl or heteroaryl moieties further substituted by an additional aryl or heteroaryl, that is itself optionally further substituted by an additional aryl or heteroaryl. These aryl and heteroaryl groups are separated by a covalent bond, or by an ethenyl, butadienyl or hexatrienyl linkage. The dyes of the invention are particularly useful as labels for carriers, particularly polymeric microparticles. The resulting microparticles have a long-wavelength fluorescence emission, and possess utility for tracing flow in biological systems, particularly in tracing blood flow.Type: GrantFiled: May 14, 1997Date of Patent: December 21, 1999Assignee: Molecular Probes, Inc.Inventors: Yexin Wu, Dieter H. Klaubert, Hee Chol Kang, Yu-Zhong Zhang
-
Patent number: 6001999Abstract: The invention relates to a compound having the general Formula I in which one of the groups R.sub.1,R.sub.2,R.sub.3,R.sub.4,R.sub.5,R.sub.6 and R.sub.7 represents an ionophoric moiety and the remaining groups each independently are hydrogen, a lipophilic or hydrophilic group or a reactive group for coupling to a polymer or a biomolecule, or R.sub.2 forms an aromatic ring system together with R.sub.3 and R.sub.5 forms an aromatic ring system together with R.sub.6.the compound of the invention is useful as a luminescence indicator for cations.Type: GrantFiled: May 27, 1998Date of Patent: December 14, 1999Assignee: AVL Medical InstrumentsInventors: Otto S. Wolfbeis, Jorg Daub, Thomas Gareis, Matthias Kollmannsberger, Stefan Heinl, Tobias Werner, Christian Huber, Andrei Boila-Gockel, Marco Jean Pierre Leiner
-
Patent number: 5939560Abstract: Compounds selected from those of general formula ?A-B (Groups I and II)! and (group III), (1, 2 and 3) where B is (4) and A is selected from specified aminoacyl compounds are inhibitors of DP-IV mediated processes.Type: GrantFiled: August 27, 1996Date of Patent: August 17, 1999Assignee: Ferring B.V.Inventors: Paul D. Jenkins, D. Michael Jones, Michael Szelke
-
Patent number: 5872083Abstract: A succinimide composition is prepared by reacting a mixture of an alkenyl or alkylsuccinic acid derivative, an unsaturated acidic reagent copolymer, and a polyamine under reactive conditions. The alkenyl or alkyl substituent of the alkenyl or alkylsuccinic acid derivative has a Mn of from 1000 to 5000. The unsaturated acidic reagent copolymer is a copolymer of an unsaturated acidic reagent and an alkylene group. That alkylene group can be an .alpha.-olefin having 8 to 42 carbon atoms, a polyalkylene having from 8 to 28 carbon atoms, ethylene, styrene, 1,3-butadiene, vinyl alkyl ether having at least 3 carbon atoms, or vinyl alkanoate having at least 4 carbon atoms. The polyamine has at least three nitrogen atoms and 4 to 20 carbon atoms. The mixture contains from 0.5 to 10 equivalents of the alkenyl or alkylsuccinic acid derivative per equivalent of unsaturated acidic reagent copolymer and from 0.4 to 1.Type: GrantFiled: July 29, 1997Date of Patent: February 16, 1999Assignee: Chevron Chemical CompanyInventors: James J. Harrison, William R. Ruhe, Jr.
-
Patent number: 5869689Abstract: Dipyrrometheneboron difluoride dyes possessing a covalently attached basic amine moiety are described that have utility for staining acidic organelles. Samples comprising isolated acidic organelles, or a cell or cells containing acidic organelles, are stained by preparing an aqueous labeling solution of the dye and incubating the sample in the labeling solution for a time sufficient to produce fluorescent labeled acidic organelles.Type: GrantFiled: October 17, 1995Date of Patent: February 9, 1999Assignee: Molecular Probes, IncInventors: Yu-Zhong Zhang, Zhenjun Diwu, Richard P. Haugland
-
Patent number: 5864044Abstract: Disclosed herein are novel trisulfonated phathalocyanines, processes for making them and their derivatives. Also disclosed are key intermediates consisting of Boron(III) subphathalocyanines. Further disclosed are novel uses for various water soluble trisulfophathalocyanines, trisulfobenzonapthoporphyrazines and trisulfonated phathalocyanines. The new uses are directed to photsensitizers for the photodynamic therapy of cancer, the inactivation of viruses in stored blood, organic semiconductors, disk memory material or as materials for gas sensors. In the compounds of the present invention, the central metal atom may be Zn, Co(II), Ni or Cu(II).Type: GrantFiled: July 24, 1997Date of Patent: January 26, 1999Assignee: Universite de SherbrookeInventors: Johannes E. Van Lier, Svetlana V. Kudrevich, Sandra Gilbert
-
Patent number: 5808064Abstract: We have found that 2-unsubstituted indoles of structural formula (IV) can be cost-effectively synthesized in high yield by the palladium-catalyzed coupling/ring closure of a 2-halo or 2-trifluoromethylsulfonyloxy aniline (I) and an acyl silane derivative (II), followed by deprotection of the silyl protecting groups. ##STR1## The process of the present invention is particularly useful to form indoles containing acid-labile substituents such as triazole, acetyl, ketal, cyano, and carbamate, or indoles having a good leaving group in the benzyl position. The advantages of the present process are that it does not require the use of triphenyl phosphine or tetrabutyl ammonium chloride or lithium chloride. When applied to 5-triazolyl substituted indoles, the present process also eliminates the tendency of triazolyl polymerization in the Fischer indole synthesis.Type: GrantFiled: August 7, 1997Date of Patent: September 15, 1998Assignee: Merck & Co., Inc.Inventors: Cheng-Yi Chen, Robert D. Larsen
-
Patent number: 5804395Abstract: Fluorescent-labeled substrates are provided for fluorescence polarization says of enzymes. These substrates are proteins labeled with derivatives of BODIPY.RTM., 4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene. The BODIPY.RTM. fluorescent tag of the present invention is pH independent, and can be used over a pH range of from about 2 to about 11. Thus one can assay, in real time, enzymes with pH maxima at pH below 7 using fluorescence polarization methodology, which could not be done with fluorescein derivatives. Different enzymes can be compared using the same BODIPY.RTM. conjugate by merely changing the buffer system which changes the pH conditions.Fluorescence polarization assays of enzyme activity can be performed in the presence of whole bacteria and other finely suspended particles, such as might be present in tissue homogenates or cellular material. This is particularly useful for chairside assays on dental plaque or clinical assays on bacteria or tissue or exudates.Type: GrantFiled: December 1, 1995Date of Patent: September 8, 1998Assignee: The United States of America as represented by the Secretary of the NavyInventors: Sylvia Zottu Schade, Michael Ernest Jolley
-
Patent number: 5786485Abstract: An optically active .beta.-aminoalkoxyborane complex of the formula (I): ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.7 -C.sub.11 aralkyl or C.sub.6 -C.sub.10 aryl, R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.7 -C.sub.11 aralkyl, or R.sup.1 and R.sup.2 together form (CH.sub.2).sub.n wherein n is 3 or 4, and Ar is naphthyl, anthryl or phenanthryl, which may be substituted by from 1 to 3 substituents selected from the group consisting of halogen, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.7 -C.sub.11 aralkyl, C.sub.6 -C.sub.10 aryl, C.sub.1 -C.sub.6 alkoxy and styrene polymer substituents.Type: GrantFiled: April 29, 1997Date of Patent: July 28, 1998Assignee: Nissan Chemical Industries, Ltd.Inventors: Hiroshi Kashihara, Mikio Suzuki, Yoshio Ohara
-
Patent number: 5728529Abstract: Methods for the use of a class of dyes for improved DNA sequencing by the chain termination method of DNA sequencing, and internal labelling of polynucleotides by enzymatic incorporation of fluorescently-labeled ribonucleotides or deoxyribonucleotides are provided. A new class of dyes, BODIPY.RTM. fluorophores, has been described recently. The parent heterocyclic molecule of the BODIPY.RTM. fluorophores is a dipyrrometheneboron difluoride compound which is modified to create a broad class of spectrally-discriminating fluorophores. BODIPY.RTM. fluorophores have improved spectral characteristics compared to conventional fluorescein and rhodamine dyes. BODIPY.RTM. fluorophores have narrower band width, insensitivity to solvent or pH, and improved photostability, thus, BODIPY.RTM. fluorophores lead to improved DNA sequencing and/or detection in any method where electrophoresis and detection of DNA is required. Additionally, the spectral properties of the BODIPY.RTM.Type: GrantFiled: November 6, 1995Date of Patent: March 17, 1998Assignee: Baylor College Of MedicineInventors: Michael L. Metzker, Richard A. Gibbs
-
Patent number: 5723218Abstract: The invention is a novel fluorescently labeled microparticle, where the microparticle internally incorporates at least one dipyrrometheneboron difluoride dye. Appropriate selection of substituents results in dipyrrometheneboron difluoride derivatives that, when incorporated into polymer microparticles, give the desired excitation and emission wavelengths. The spectral characteristics of the labeling dyes in liquid are not greatly changed when the dye is incorporated into the particles, and the spectral excitation and emission wavelengths are compatible with commonly used filter sets. Other embodiments of the fluorescent microparticles include additional dyes and/or bioreactive substances.Type: GrantFiled: June 7, 1995Date of Patent: March 3, 1998Assignee: Molecular Probes, Inc.Inventors: Richard P. Haugland, Rosaria P. Haugland, John Michael Brinkley, Hee Chol Kang, Michael Kuhn, K. Sam Wells, Yu Zhong Zhang
-
Patent number: 5703258Abstract: A flame retardant organic silicon and phosphorus containing compound is produced by reacting a silicon halides compound with an organic phosphorus compound to produce an organic silicon and phosphorus halides compound which is then reacted with an organic compound to produce an organic silicon and phosphorus containing compound. This organic silicon and phosphorus containing compound is incorporated in an otherwise more flammable organic material under reaction conditions and in an amount sufficient to reduce the combustibility of the otherwise more flammable organic material. The organic silicon and phosphorus containing compound may also be utilized as coating agents, adhesives, surfactants, insecticides, hydraulic fluid and other uses.Type: GrantFiled: November 20, 1996Date of Patent: December 30, 1997Inventor: David H. Blount
-
Patent number: 5691436Abstract: A mixture of silicon and phosphorus are heated and reacted with halide to produce silicon tetrahalides, silicon-phosphorus halide and phosphorus trihalides compositions. These compositions are reacted with any suitable organic, inorganic-organic and/or inorganic compound to produce novel organic silicon-phosphorus containing compositions. These compositions may be utilized as flame retardants, coating agents, adhesives and many other uses.Type: GrantFiled: December 16, 1996Date of Patent: November 25, 1997Inventor: David H. Blount
-
Patent number: 5691374Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.Type: GrantFiled: May 18, 1995Date of Patent: November 25, 1997Assignee: Merck Frosst Canada Inc.Inventors: Cameron Black, Erich Grimm, Zhaoyin Wang, Serge Leger
-
Patent number: 5643893Abstract: Novel N-substituted-(dihydroxyboryl)alkyl purine, indole and pyrimidine derivatives have been found to be useful as inhibitors of inflammatory cytokines. They can be used, inter alia, in the therapy of septic shock, cachexia, rheumatoid arthritis, inflammatory bowel disease, multiple sclerosis and AIDS. The compounds are typically prepared by reaction of an bromoalkyl boronic acid with the purine, indole or pyrimidine base.Type: GrantFiled: June 22, 1994Date of Patent: July 1, 1997Assignees: Macronex, Inc., University of North CarolinaInventors: Bradley J. Benson, Xiannong Chen, George J. Cianciolo, Jose-Luis Diaz, Khalid S. Ishaq, Susan L. Morris-Natschke, Ronald J. Uhing, Henry Wong
-
Patent number: 5631364Abstract: The invention provides novel labelled boronic acid conjugates of formula ##STR1## (wherein V is a reporter moiety; W.sup.2 is a bond or an organic linker moiety;W.sup.1 is a *SO.sub.2 NR.sup.2, *CON.sup.2 or *CH.sub.2 N.sym.R.sup.2 .sub.2 group bound at the *-marked atom to the phenyl ring;R.sup.1 is hydrogen or an electron withdrawing substituent group; andeach R.sup.2 independently is hydrogen or an optionally hydroxylated and optionally C.sub.1-6 -alkoxylated C.sub.1-6 -alkyl group) and salts thereof, e.g. for use in assays for cis-diols such as glycated blood proteins, having enhanced water-solubility and storage stability.Type: GrantFiled: March 31, 1994Date of Patent: May 20, 1997Assignee: AXIS Biochemicals ASAInventors: Erling Sundrehagen, Frank Frantzen
-
Patent number: 5563127Abstract: Novel boronic acid and ester and carboxyl-modified amino acid compounds of the Formula I, which are inhibitors of trypsin-like enzymes, are disclosed :R.sup.1 --Z--CHR.sup.2 --A,where R.sup.1, Z, R.sup.2 and A are defined within.Type: GrantFiled: December 27, 1994Date of Patent: October 8, 1996Assignee: The DuPont Merck Pharmaceutical CompanyInventors: Eugene C. Amparo, William H. Miller, Gregory J. Pacofsky, John Wityak, Patricia C. Weber, John J. V. Duncia, Joseph B. Santella, III
-
Patent number: 5552548Abstract: The borane reduction of prochiral ketones to optically pure alcohols is effectively achieved by the utilization of catalytic amounts of the new and valuable oxazaborolidine catalysts of formula (I).Type: GrantFiled: October 13, 1994Date of Patent: September 3, 1996Assignee: Pfizer Inc.Inventor: George J. Quallich
-
Patent number: 5514642Abstract: Cyclohexenone oxime ethers of the formula I ##STR1##Type: GrantFiled: February 13, 1995Date of Patent: May 7, 1996Assignee: BASF AktiengesellschaftInventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Dieter Kolassa, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber, Uwe Kardorff
-
Patent number: 5502065Abstract: The present invention provides compounds of the formula: ##STR1## and pharmaceutically acceptable salts thereof.Type: GrantFiled: September 21, 1994Date of Patent: March 26, 1996Assignee: Pfizer Inc.Inventors: Alan D. Brown, Roger P. Dickinson, Martin J. Wythes
-
Patent number: 5482960Abstract: Novel indole and indoline nonpeptide antagonists of endothelin I are described, as well as novel intermediates used in their preparation, methods for the preparation and pharmaceutical compositions of the same, which are useful in treating elevated levels of endothelin, essential renovascular malignant and pulmonary hypertension, cerebral infarction, cerebral ischemia, congestive heart failure and subarachnoid hemorrhage.Type: GrantFiled: November 14, 1994Date of Patent: January 9, 1996Assignee: Warner-Lambert CompanyInventors: Kent A. Berryman, Amy M. Bunker, Annette M. Doherty, Jeremy J. Edmunds
-
Patent number: 5466798Abstract: The present invention relates to novel, powerful reducing agents, lithium aminoborohydrides which are prepared by addition of BH.sub.3 .cndot.THF to the corresponding dialkylamine at 25.degree. C. to give the intermediate amineborane complex. Subsequent deprotonation by strong base, e.g. n-BuLi, yields the aminoborohydride quantitatively. Lithium aminoborohydrides are powerful reducing agents, comparable in strength to lithium aluminum hydride. The activity is determined by the dialkylamine. Lithium pyrrolidinoborohydride has unique activity and selectivity in its reducing properties. Esters, lactones and anhydrides are reduced cleanly at 25.degree. C. to give the corresponding alcohols, while carboxylic acids are not reduced. Test reductions show that lithium pyrrolidinoborohydride is also capable of reducing a wide range of functional groups including amides, epoxides, oximes, nitriles and halides.Type: GrantFiled: October 15, 1993Date of Patent: November 14, 1995Assignee: The Regents of the University of CaliforniaInventors: Bakthan Singaram, Gary B. Fisher, Joseph C. Fuller, John Harrison, Christian T. Goralski
-
Patent number: 5462964Abstract: The present invention relates to the discovery of new C-terminal boronic acid dipeptide inhibitors of trypsin-like enzymes such as thrombin and pharmaceutical compositions thereof.Type: GrantFiled: October 20, 1993Date of Patent: October 31, 1995Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: John M. Fevig, Matthew M. Abelman, Eugene C. Amparo, Joseph Cacciola, Charles A. Kettner, Gregory J. Pacofsky, Chia-Lin Wang
-
Patent number: 5451663Abstract: This invention relates to derivatives of dipyrrometheneboron difluoride fluorescent dyes that have an absorption maximum at wavelengths longer than about 525 nm, and are chemically reactive with nucleic acids, proteins, carbohydrates, and other biologically derived or synthetic chemical materials to form dye-conjugates. The dye-conjugates generally have the structure: ##STR1## wherein at least one of the substituents R.sub.1 -R.sub.7, covalently bonds to a specific binding pair member, and further where at least one of the substituents R.sub.1 -R.sub.7 contains a bathochromic moiety that is heteroaryl or alkenyl. The remaining substituents, which may be the same or different, are hydrogen, halogen, alkyl (containing 1-5 carbon atoms), aryl, arylalkyl, or sulfo.Type: GrantFiled: April 8, 1993Date of Patent: September 19, 1995Assignee: Molecular Probes, Inc.Inventors: Hee C. Kang, Richard P. Haugland
-
Patent number: 5446157Abstract: A new group of fluorescent organic compounds having a variety of uses are described. They are especially useful as dye compounds in dye laser systems, and as photochemical agents in the treatment of diseased tissues using photodynamic therapy techniques. The compounds include a tri-cyclic compound having the following structure: ##STR1## Preferably R.sub.1 -R.sub.5 .dbd.R.sub.9 -R.sub.12 .dbd.C; R.sub.7 .dbd.B; R.sub.6 and R.sub.8 .dbd.N; R.sub.14 .dbd.lower n-alkyl or an electron withdrawing group such as CN.sup.- ; R.sub.16 and R.sub.19 are independently selected from the group consisting of lower n-alkyl, a sulfate or an acid or salt thereof, or hydrogen; and R.sub.20 .dbd.R.sub.21 .dbd.F.Type: GrantFiled: February 19, 1993Date of Patent: August 29, 1995Inventors: Lee R. Morgan, Joseph H. Boyer
-
Patent number: 5433896Abstract: The invention relates to fluorescent dyes that are substituted or unsubstituted derivatives of 1-[isoindolyl]methylene-isoindole that are bound through both isoindole nitrogens to a boron difluoride moiety, forming a fluorescent dibenzopyrrometheneboron difluoride compound ##STR1## whose fluorescence properties are modified by the selection of appropriate chemical substituents.The dibenzopyrrometheneboron difluoride compound is optionally substituted by hydrogen, halogen cyano, sulfo, alkali or ammonium salts of sulfo, carboxy, substituted or unsubstituted alkyl, perfluoroalkyl, alkoxy, alkylthio, nitro, amino, monoalkylamino, dialkylamino, substituted or unsubstituted aryl substituents, substituted or unsubstituted heteroaryl substituents, or additional substituted or unsubstituted fused benzo rings or substituted or unsubstituted fused heteroaromatic rings.Type: GrantFiled: May 20, 1994Date of Patent: July 18, 1995Assignee: Molecular Probes, Inc.Inventors: Hee C. Kang, Richard P. Haugland
-
Patent number: 5432288Abstract: Novel O.sub.10eq -derivatives of ryanodine and dehydroryanodine characterized as binding strongly to ryanodine receptor, useful in affecting Ca.sup.++ efflux in tissue and also in isolating ryanodine receptor from sarcoplasmic reticulum. Also described are novel radio-iodinated alanine derivatives useful to radio label ryanodine and dehydroryanodine derivatives.Type: GrantFiled: March 2, 1993Date of Patent: July 11, 1995Assignee: Indiana University FoundationInventors: Koert Gerzon, Rod A. Humerickhouse, Henry R. Bensch, Jr., Keshore R. Bidasee
-
Patent number: 5397792Abstract: An improved process for the preparation of trans-6-[2-(substituted-pyrrole-1-yl)alkyl]pyran-2-ones by a novel synthesis is described where .alpha.-metalated N,N-disubstituted acetamide is converted in seven operations to the desired products, and specifically, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl) -N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyr role-3-carboxamide, as well as other valuable intermediates used in the processes and prodrugs which are bioconverted to hypolipidemic and hypocholesterolemic agents and pharmaceutical compositions of the same.Type: GrantFiled: May 16, 1994Date of Patent: March 14, 1995Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, Tung Van Le, Thomas N. Nanninga
-
Patent number: 5384410Abstract: A method for the removal of ester protecting groups from .alpha.-amino boronic acid is disclosed for the preparation of compounds of formula (II) belowR.sup.1 -X.sub.n -NHCH (R.sup.2)-B(OH).sub.Type: GrantFiled: March 24, 1993Date of Patent: January 24, 1995Assignee: The Du Pont Merck Pharmaceutical CompanyInventor: Charles A. Kettner
-
Patent number: 5338854Abstract: This invention relates to improved fluorescent fatty acid analogs derived from dipyrrometheneboron difluoride ("BDY") dyes that absorb light at wavelengths longer than 480 nm. The BDY fluorophore or a derivative thereof is incorporated at various locations along the alkyl portion of the fatty acid ("BDY fatty acid"). The general formula of a BDY fatty acid is as follows: ##STR1## wherein at least one of the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 is a carboxylic acid terminated alkyl residue containing 5 to 22 carbon atoms. The remaining substituents, singly or in any combination, are: additional alkyl or arylalkyl residues containing 1 to 16 aliphatic carbon atoms, or aryl or heteroaryl residues, or hydrogen. Symmetrically substituted BDY fluorophores are conveniently synthesized from a single pyrrole precursor in a "one-pot" reaction. Alternatively, BDY fatty acids are synthesized from two different pyrrole precursors.Type: GrantFiled: February 13, 1991Date of Patent: August 16, 1994Assignee: Molecular Probes, Inc.Inventors: Hee C. Kang, Richard P. Haugland
-
Patent number: 5329046Abstract: The invention relates to biscationic acid amide and acid imide derivatives with an anion of formula (BR.sub.9 R.sub.10 R.sub.11 R.sub.12)--, where R.sub.9 to R.sub.12 are aliphatic, iso- or heterocyclic aromatic residues or aralkyl residues, which may be substituted by C.sub.1 -C.sub.4 -alkyl residues, C.sub.1 -C.sub.4 -alkoxy residues, aryl residues or halogen atoms (e.g. fluorine atoms), and mixtures of these compounds and mixed crystals with mixed anions and/or cations. The invention also relates to a process for preparing them. The new compounds are excellent colorless charge controllers in toners and developers for electrophotographic recording and as charge-enhancers in powders and paints for surface coating, in particular in triboelectrically or electrokinetically sprayed powder paints.Type: GrantFiled: June 25, 1992Date of Patent: July 12, 1994Assignee: Hoechst AktiengesellschaftInventors: Hans-Tobias Macholdt, Siegfried Schiessler, Jorg Gitzel, Erwin Dietz
-
Patent number: 5280119Abstract: Heterocyclic amine-borane compounds of the formula: ##STR1## wherein: A is a heterocyclic amine moiety selected from the group consisting of piperidine, substituted piperidine, piperazine, substituted piperazine, imidazole, substituted imidazole, pyrazole, substituted pyrazole, pyrazine, substituted pyrazine, pyrrole, substituted pyrrole, pyrrolidine, substituted pyrrolidine, indole, substituted indole, indoline, substituted indoline, quinoline, substituted quinoline, isoquinoline, substituted isoquinoline, thiazole, substituted thiazole, oxazole, substituted oxazole, thiazolidine, and substituted thiazolidine, wherein substitution is at any or all substituent positions, and comprises substituents selected from the group consisting of alkyl (preferably C.sub.1 -C.sub.10 linear or branched alkyl), alkylaryl, aryl, aralkyl, nitro, alkoxy, hydroxy, cyano, thiol, and halo;R.sub.1 is selected from H, alkyl (preferably C.sub.1 -C.sub.10 linear or branched alkyl), alkylaryl, aryl, and arylalkyl; andR.sub.Type: GrantFiled: November 1, 1991Date of Patent: January 18, 1994Assignee: Boron Biologicals, Inc.Inventors: Bernard F. Spielvogel, Anup Sood, Iris H. Hall
-
Patent number: 5274113Abstract: This invention relates to derivatives of dipyrrometheneboron difluoride fluorescent dyes that have an absorption maximum at wavelengths longer than about 525 nm, and are chemically reactive with nucleic acids, proteins, carbohydrates, and other biologically derived or synthetic chemical materials. The dyes generally have the structure: ##STR1## wherein at least one of the substituents R.sub.1 -R.sub.7, is a reactive functional group, and at least one of the substituents R.sub.1 -R.sub.7 contains a bathochromic moiety. The bathochromic moiety is an unsaturated organic group, preferably heteroaryl or alkenyl. The remaining substituents, which may be the same or different, are hydrogen, halogen, alkyl (containing 1-5 carbon atoms), aryl, arylalkyl, or sulfo. The dyes are used to make novel conjugates with members of specific binding pairs that are ligands or receptors.Type: GrantFiled: November 1, 1991Date of Patent: December 28, 1993Assignee: Molecular Probes, Inc.Inventors: Hee C. Kang, Richard P. Haugland