The Other Cyclo Of The Bicyclo Ring System Is A Six-membered Carbocyclic Ring To Which Chalcogen Is Directly Attached Patents (Class 549/289)
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Publication number: 20020120156Abstract: The present invention is a method for producing warfarin sodium from warfarin sodium 2-propanol clathrate by thermal, nondestructive solvent expulsion. The solvent expulsion is conducted under conditions of controlled heat transfer whereby the 2-propanol is expelled from the warfarin sodium 2-propanol clathrate without decomposition of warfarin sodium or the clathrate. Heating is conducted the clathrate at a temperature from about 100° C. to about 170° C. in an active oven under air or in an inert atmosphere and at partial pressures ranging from that of a relative vacuum to atmospheric pressure. The invention also relates to pure warfarin sodium prepared according to the method of the invention and pharmaceutical compositions containing warfarin sodium.Type: ApplicationFiled: February 28, 2001Publication date: August 29, 2002Inventors: Sorin Bercovici, Shimon Chernyak, Konstantin Ulanenko
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Publication number: 20020120157Abstract: The invention provides a method for the direct preparation of pure warfarin sodium from warfarin acid. The reaction is conducted in a polar organic solvent, preferably ethanol, using a volatilizable base, preferably sodium bicarbonate or sodium carbonate, at low temperature. Drying the final product is accomplished at low temperature to avoid decomposition of the final warfarin sodium product.Type: ApplicationFiled: February 28, 2001Publication date: August 29, 2002Inventors: Michel Ashkar, Sorin Bercovici, Robert Graff
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Patent number: 6426420Abstract: Provided is a process for producing an isocoumarin-3-yl-acetic acid derivative, characterized by reacting a homophthalic acid derivative represented by a formula: (wherein Rc, R2 and R are mainly protecting groups) with a malonic acid derivating represented by a formula: (wherein R is an organic group including a lower alkyl group; R3 is a protecting group for a carboxyl group; and X is a halogen atom or a —OM group (wherein M is alkaline metal or alkaline earth metal)). According to the above process, various isocoumarin-3-yl-acetic acid derivatives can efficiently be provided.Type: GrantFiled: July 5, 2000Date of Patent: July 30, 2002Assignees: Mercian Corporation, Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Toshio Tsuchida, Hazuki Nagai, Takashi Nakashima, Masashi Yoshida, Kaname Konuki, Asako Kuroda, Kunio Isshiki, Tomio Takeuchi
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Patent number: 6420130Abstract: The invention provides a compound, useful as an optical probe or sensor of the activity of at least one cytochrome P450 enzyme, and methods of using the compound to screen candidate drugs, and candidate drugs identified by these methods.Type: GrantFiled: April 28, 1999Date of Patent: July 16, 2002Assignee: Aurora Biosciences CorporationInventors: Lewis R. Makings, Gregor Zlokarnik
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Patent number: 6420401Abstract: Substituted derivatives of 1,2,5-thiadiazolidin-3-one 1,1-dioxides, oligomers containing them, and methods of using them.Type: GrantFiled: August 22, 1997Date of Patent: July 16, 2002Assignee: Wichita State UniversityInventors: William C. Groutas, Rongze Kuang
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Patent number: 6387258Abstract: A process for purifying statin compounds from a fermentation broth by extraction and crystallization is disclosed. A fermentation broth is subjected to a pretreatment procedure which involves an alkaline pretreatment and an alkaline purification. Following the pretreatment procedure, the statin compound is extracted under acidic conditions into a hydrophobic solvent and purified by crystallization. The organic extraction solvent is concentrated and then extracted with a mild base. The statin compound is then purified by crystallization.Type: GrantFiled: January 25, 2001Date of Patent: May 14, 2002Assignee: Biogal Gyogyszergyar Rt.Inventors: Vilmos Keri, Lajos Deak, Iiona Forgacs
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Patent number: 6372739Abstract: Compounds that modulate gene expression through the estrogen receptor (ER) are disclosed having the following structure, as well as pharmaceutical compositions containing the same: wherein R1, R2, R3, n and p are as defined here. Methods are also disclosed for modulating ER in cells and/or tissues expressing the same, such as bone, breast, prostate, uterus, CNS or the cardiovascular system. Methods for treating estrogen-related conditions are also disclosed, including conditions such as is breast cancer, osteoporosis, endometriosis, cardiovascular disease, hypercholesterolemia, prostatic hypertrophy, prostatic carcinomas, obesity, hot flashes, skin effects, mood swings, memory loss, and adverse reproductive effects associated with exposure to environmental chemicals or natural hormonal imbalances.Type: GrantFiled: July 2, 2001Date of Patent: April 16, 2002Assignee: Signal Pharmaceuticals, Inc.Inventors: Bernd M. Stein, David Wesley Anderson, Leah M. Gayo-Fung, Mary Doubleday, Graziella I. Shevlin, Adam Kois, Sak Khammungkhune, Ravi Kumar Jalluri, Shripad S. Bhagwat, Jeffrey A. McKie
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Patent number: 6344334Abstract: Method for identifying a drug lead compound that inhibits binding of target bioogical molecules (TBM) by contacting TBM with members of a library of candidate cross-linked target binding fragments (CXBF), each CXBF having at least two candidate target bindig fragments (CTBF), which are inhibitors of binding, linked to a cross-linker, and selecting CXBF that inhibit the binding of the TBM to a greater extent than either of the individual CTBF linked to said cross-linker, wherein the library of CXBF is produced by: (a) screening a population of CTBF capable of being chemically cross-linked by a cross-linker to identify a subpopulation of the CTBF that inhibit binding of the TBM; and (b) chemically cross-linking members of the subpopulation of CTBF or structurally related analogs thereof with a cross-linker to provide a library of CXBF, wherein at least one linking group comprises an oxime ether linking group.Type: GrantFiled: March 26, 1999Date of Patent: February 5, 2002Assignee: The Regents of the University of CaliforniaInventors: Jonathan A. Ellman, Ingrid Choong
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Patent number: 6344330Abstract: The present invention is directed to novel methods for identifying small molecule ligands that are capable of binding with high affinity to a biological target molecule of interest. High affinity binding ligands identified by the described methods find use, for example, as small molecule lead compounds that may they themselves be, or may give rise to, novel therapeutic drugs. More specifically, the subject invention is directed to methods for identifying a ligand that binds to a target biological molecule of interest, wherein a population of small organic compounds are selected and then “pre-screened” to identify those that are capable of binding to the molecular target.Type: GrantFiled: March 27, 1998Date of Patent: February 5, 2002Assignee: The Regents of the University of CaliforniaInventors: Jonathan A. Ellman, Ingrid Choong
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Patent number: 6331562Abstract: Compounds that modulate gene expression through the estrogen receptor (ER) are disclosed having the following structure, as well as pharmaceutical compositions containing the same: wherein R1, R2, R3, n and p are as defined here. In a specific embodiment, the compounds are selective modulators for Er-&bgr; over ER-&agr;. Methods are also disclosed for modulating ER-&bgr; in cells and/or tissues expressing the same, including cells and/or tissues that preferentially express ER-&bgr;. More generally, methods for treating estrogen-related conditions are also disclosed, including conditions such as is breast cancer, testicular cancer, osteoporosis, endometriosis, cardiovascular disease, hypercholesterolemia, prostatic hypertrophy, prostatic carcinomas, obesity, hot flashes, skin effects, mood swings, memory loss, urinary incontinence, hairloss, cataracts, natural hormonal imbalances, and adverse reproductive effects associated with exposure to environmental chemicals.Type: GrantFiled: July 6, 2000Date of Patent: December 18, 2001Assignee: Signal Pharmaceuticals, Inc.Inventors: Shripad S. Bhagwat, Jeffrey A. McKie, Sak Khammungkhune
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Patent number: 6310248Abstract: The invention relates to a process for the enantioselective preparation of tolterodine and analogues and salts thereof comprises the steps of: a) enantioselectively reducing the carbonyl function in a compound of formula (II): wherein R1, R2 and R3 independently of each other are hydrogen, methyl, methoxy, hydroxy, hydroxymethyl, carbamoyl, sulphamoyl or halogen, to form an enantiomerically enriched compound of formula (IIIa) or (IIIb): wherein R1, R2 and R3 are as defined above; b) subjecting the compound of formula (IIIa) or (IIIb) to a sigmatropic rearrangement to form a corresponding enantiomerically enriched compound of formula (IVa) or (IVb): wherein R1, R2 and R3 are as defined above; c) subjecting the compound of formula (IVa) or (IVb) to a Baeyer-Virliger oxidation to form a corresponding enantiomerically enriched compound of the general formula (Va) or (Vb): wherein R1, R2 and R3 are as defined above; d) converting the compoType: GrantFiled: December 22, 2000Date of Patent: October 30, 2001Assignee: Pharmacia ABInventors: Pher G. Andersson, Christian Hedberg
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Patent number: 6291456Abstract: Compounds that modulate gene expression through the estrogen receptor (ER) are disclosed having the following structure, as well as pharmaceutical compositions containing the same: wherein R1, R2, R3, n and p are as defined here. Methods are also disclosed for modulating ER in cells and/or tissues expressing the same, such as bone, breast, prostate, uterus, CNS or the cardiovascular system. Methods for treating estrogen-related conditions are also disclosed, including conditions such as is breast cancer, osteoporosis, endometriosis, cardiovascular disease, hypercholesterolemia, prostatic hypertrophy, prostatic carcinomas, obesity, hot flashes, skin effects, mood swings, memory loss, and adverse reproductive effects associated with exposure to environmental chemicals or natural hormonal imbalances.Type: GrantFiled: January 27, 2000Date of Patent: September 18, 2001Assignee: Signal Pharmaceuticals, Inc.Inventors: Bernd M. Stein, David Wesley Anderson, Leah M. Gayo-Fung, May S. Sutherland, Mary Doubleday, Graziella I. Shevlin, Adam Kois, Sak Khammungkhune, Ravi Kumar Jalluri, Shripad S. Bhagwat, Jeffrey A. McKie
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Patent number: 6258839Abstract: A compound of general formula I in which the 2-3 bond in ring C could be double or single bond. Ring B and its substituents may be attached at position 2 (at J) in ring C. The key feature in the modifications is that the prenylation must not cyclize through the free OH groups(s) at ortho position to the prenylation. Atoms attached at X in ring C may be S or N or P or C or O or pharmaceutically acceptable metal or CH2.Type: GrantFiled: December 24, 1997Date of Patent: July 10, 2001Inventor: Peter Mashava
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Patent number: 6215006Abstract: The present invention relates to a process for the preparation of a 3-isochromanone of the formula (I) by reaction of an o-chloromethylphenylacetic acid of the formula (II) at a temperature of 100 to 250° C. in the presence or absence of an ionic halide, in the presence or absence of an organic solvent with and removal of hydrogen chloride, where in the formulae (I) and (II) the radicals R1, R2, R3 and R4 independently of one another are: a hydrogen or fluorine atom; an NC or F3C group; an alkyl alkoxy or acyloxy radical, each having 1 to 18 carbon atoms; or a C6-C18-aryloxy, aryl or heteroaryl radical, 1 to 3 atoms from the group consisting of O, N and/or S being present as heteroatoms; or in which at least two of the radicals R1, R2, R3 and R4 are linked to one another and form at least one aliphatic or aromatic ring having 5 to 18 carbon atoms.Type: GrantFiled: May 19, 2000Date of Patent: April 10, 2001Assignee: Clariant GmbHInventor: Holger Geissler
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Patent number: 6100292Abstract: This invention relates to ketones represented by the following formula ##STR1## and to drugs in which such a ketone or pharmacologically acceptable salt thereof is an effective component.The ketones of the present invention encourage the production of platelets, red blood cells, white blood cells and the like, and can be used to prevent or treat cytopaenia brought about by cancer chemotherapy, radiotherapy, bone marrow transplantation and drug therapy, or by immunological abnormality or anaemia, and the like.Type: GrantFiled: May 25, 1999Date of Patent: August 8, 2000Assignee: Toray Industries, Inc.Inventors: Tsuyoshi Matsumoto, Hideki Kawai, Kiyoshi Okano, Katsuyuki Mori, Yasumoto Adachi
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Patent number: 6083553Abstract: Methods for recovering isoflavones and derivatives thereof from soy molasses are disclosed. In a first embodiment, a method is disclosed in which isoflavones are recovered from soy molasses. In a second embodiment, a method is disclosed whereby isoflavone conjugates present in soy molasses are converted to isoflavone glucosides, and an isoflavone glucoside material is recovered from the soy molasses. In a third embodiment, a method is disclosed in which isoflavones are converted to their aglucone form, and an aglucone isoflavone material is recovered from soy molasses.Type: GrantFiled: June 5, 1998Date of Patent: July 4, 2000Assignee: Protein Technologies International, Inc.Inventors: Doyle H. Waggle, Barbara A. Bryan
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Patent number: 6075152Abstract: The present invention relates to a process for preparing an isochroman-3-one of the formula (I) by reacting a 1,2-bishalomethylbenzene of the formula (II) ##STR1## in which X is chlorine, bromine or iodine with carbon monoxide and water at a CO pressure of from 0.1 to 50 MPa and a temperature of from 20 to 200.degree. C. in the presence or absence of an ionic halide, in the presence of a palladium catalyst and a dipolar aprotic solvent, where in the formulae (I) and (II) the radicals R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another denote:a hydrogen or fluorine atom;a HO.sub.2 CCH.dbd.CH--, NC-- or F.sub.3 C group;an alkyl, alkoxy or acyloxy radical having in each case 1 to 18 carbon atoms; or a C.sub.6 -C.sub.18 -aryloxy, aryl or heteroaryl radical, where the heteroatoms present are 1 to 3 atoms from the group O, N and/or S;a R.sup.5.sub.2 P(.dbd.O)--, R.sup.6 C(.dbd.O)--, R.sup.6 OC(.dbd.O)--, R.sup.6 OC(.dbd.O)CH.dbd.CH--, R.sup.7 C(.dbd.O)--, R.sup.7 OC(.dbd.O)CH.dbd.CH-- or R.sup.7.sub.Type: GrantFiled: April 5, 1999Date of Patent: June 13, 2000Assignee: Clariant GmbHInventors: Holger Geissler, Ralf Pfirmann
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Patent number: 6025387Abstract: The present invention relates to novel flavone/flavanone compounds or their pharmaceutically acceptable salts and process for preparation thereof for protecting gastrointestinal tracts against gastritis, ulcers and inflammatory bowel disease.Type: GrantFiled: January 14, 1999Date of Patent: February 15, 2000Assignee: Dong a Pharmaceutical Co., Ltd.Inventors: Moohi Yoo, Mi Won Son, Ik Yon Kim, Won Bae Kim, Soon Hoe Kim, Sang Deuk Lee, Geun Jho Lim, Joong In Lim, Byoung Ok Ahn, Nam Gi Baik, Dong Sung Kim, Tae Young Oh, Byung Kwon Ryu, Jae Sung Yang, Hee Chan Shin
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Patent number: 6020363Abstract: Compounds of the formula (I) ##STR1## wherein R is a hydrogen atom or a C.sub.1-6 alkyl group and n is an integer of 0 or 1, and pharmaceutical preparations thereof are provided. These pharmaceutical preparations are useful for the prevention or treatment of diseases associated with an abnormality in immunological regulatory function or vascularization.Type: GrantFiled: December 17, 1998Date of Patent: February 1, 2000Assignees: Mercian Corporation, Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Shin-ichi Hirano, Toshiyuki Mase, Naoki Agata, Hiroshi Iguchi, Naoki Matsumoto, Takeo Yoshioka, Hiroshi Tone, Hiroyuki Kumagai, Masaaki Ishizuki, Tomio Takeuchi
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Patent number: 6005093Abstract: Novel coumarin derivatives comprising a coumarin moiety linked to a non-nucleosidic backbone moiety are disclosed. The resulting molecules are typically used as photoactivate cross-linking groups when incorporated into polynucleotides as replacements for one or more of the complementary nucleoside bases present in probes used in procedures involving nucleic acid hybridization reactions.Type: GrantFiled: March 9, 1995Date of Patent: December 21, 1999Assignee: NaxcorInventors: Michael L. Wood, Peter C. Cheng, Douglas Y. Thien, David Albagli
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Patent number: 6002020Abstract: Good yields and selectivities are achieved in a process for preparing an isochroman-3-one of the formula (I) ##STR1## by reacting a 1,3-dihydroisobenzofuran of the formula (II) ##STR2## with carbon monoxide at a CO pressure of from 0.1 to 20 MPa in the presence of an ionic halide, a palladium catalyst and a dipolar aprotic solvent.Type: GrantFiled: January 27, 1999Date of Patent: December 14, 1999Assignee: Clariant GmbHInventors: Holger Geissler, Daniel Decker, Peter Gross
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Patent number: 5985912Abstract: Compounds of the formula The compounds are useful in the treatment of bacterial infections.Type: GrantFiled: September 18, 1998Date of Patent: November 16, 1999Assignee: Pfizer Inc.Inventors: Bingwei Yang, Joyce Sutcliffe, Chris J. Dutton
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Patent number: 5925671Abstract: Antitumor isocoumarins are of general formula (III) where R is --CONH.sub.2 or --CH(CH.sub.3).sub.2, or a pharmaceutically acceptable addition salt thereof. The compound wherein R is --CONH.sub.2 is the known compound amicoumacin A. The compound wherein is --CH(CH.sub.3).sub.2 is a new compound which can be obtained from fermentation of the new marine bacterium Bacillus sp. strain M-00-PHD-090, CECT 4546.Type: GrantFiled: November 6, 1997Date of Patent: July 20, 1999Assignee: Pharma Mar, s.a.Inventors: Librada Canedo Hernandez, Cristina Acebal Sarabia, Dolores Garcia Gravalos
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Patent number: 5872265Abstract: A process for producing coumarin and substituted coumarins starting from substituted hexahydrocoumarins or from substituted dihydrocoumarins. The process includes dehydrogenation in the presence of catalysts based on metals of Group VIII of the periodic table of the elements and in the presence of at least one easily reducible organic compound. The invention allows to achieve exceptionally high yields that do not require the recycling of the hexahydrocoumarin or of the dihydrocoumarin that are present at the end of the reaction, and also allows to achieve high selectivity and easy purification.Type: GrantFiled: March 17, 1997Date of Patent: February 16, 1999Assignee: Industrie Chimiche Caffaro S.P.A.Inventors: Stefano Alini, Livius Cotarca, Pietro Delogu
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Patent number: 5869701Abstract: Viral and bacterial contaminants present in biological solutions are inactivated by mixing one of a novel class of photosensitizer with said solution and irradiating the mixture.Type: GrantFiled: June 5, 1995Date of Patent: February 9, 1999Assignee: Baxter International Inc.Inventors: Sang Chul Park, Raymond P. Goodrich, Jr., Nagender Yerram, Samuel O. Sowemimo-Coker, Matthew S. Platz, Brian M. Aquila
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Patent number: 5869522Abstract: The present invention provides novel antiviral naphthoquinone compounds, which may be isolated from plants of the genus Conospermum or synthesized chemically, in accordance with the present inventive methods. The antiviral naphthoquionone compounds, derivatives thereof, and prodrugs thereof, may be used alone or in combination with other antiviral agents in compositions, such as pharmaceutical compositions, to inhibit the growth or replication of a virus, such as a retrovirus, in particular a human immunodeficiency virus, specifically HIV-1 or HIV-2, in the treatment or prevention of viral infection.Type: GrantFiled: May 31, 1995Date of Patent: February 9, 1999Assignee: The United States of America as represented by the Secretary of the Department of Health and Human ServicesInventors: Michael R. Boyd, John H. Cardelina, II, Kirk R. Gustafson, Laurent A. Decosterd, Ian Parsons, Lewis Pannell, James B. McMahon, Gordon M. Cragg
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Patent number: 5830912Abstract: The present invention comprises 6,8-difluoro-7-hydroxycoumarins and derivatives of 6,8-difluoro-7-hydroxycoumarins, including reactive dyes, dye-conjugates and enzyme substrates. These fluorine-substituted fluorescent dyes typically possess greater photostability and lower pH sensitivity in the physiological pH range than their nonfluorinated analogs, exhibit less fluorescence quenching when conjugated to a substance, possess absorption and emission spectra that closely match those of their nonfluorinated analogs, and also exhibit higher quantum yields than their nonfluorinated analogs.Type: GrantFiled: November 15, 1996Date of Patent: November 3, 1998Assignee: Molecular Probes, Inc.Inventors: Kyle R. Gee, Richard P. Haugland, Wei-Chuan Sun
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Patent number: 5731293Abstract: A compound of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are, independently, --CON(R.sup.4)R.sup.5, or a monosaccharide, or acylated monosaccharide group, with the proviso that at least one of R.sup.1 and R.sup.2 is --CON(R.sup.4)R.sup.5, and R.sup.4 and R.sup.5 are, independently, a hydrogen atom, or a hydroxyl, alkyl, aryl, or aralkyl group, or R.sup.4 and R.sup.5 together with the nitrogen atom attached thereto form a 3- to 7-membered saturated cycloaliphatic amino group, and R.sup.3 is a hydrogen atom, or a hydroxyl, alkyl, aryl, aralkyl, or --COOR.sup.8 group, and R.sup.3 is at 3- or 4-position, and R.sup.8 is a hydrogen atom or an alkyl group, or a salt thereof is disclosed. The compound has a function to inhibit a matrix metalloproteinase.Type: GrantFiled: December 28, 1995Date of Patent: March 24, 1998Assignee: Kureha Chemical Industry Co., Ltd.Inventors: Koju Watanabe, Koichi Niimura, Toru Yamazaki, Hiroshi Maruoka
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Patent number: 5723631Abstract: The present invention relates to a process for the preparation of a compound of the following structure: ##STR1## wherein, substituents are as defined in the specification.Type: GrantFiled: June 22, 1995Date of Patent: March 3, 1998Assignee: SmithKline Beecham CorporationInventors: Ashok Dharmaji Patil, Robert Philip Hertzberg, Geoffrey B. Dreyer, Alan James Freyer, John W. Westley, Balan Chenera, Michael Leo West
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Patent number: 5716982Abstract: New retinoid compounds, as coumarin retinoids and/or purine retinoids and compositions thereof, are provided which exhibit therapeutic and/or biological activity on cancer or precancer cells, as well as to methods of use of same.Type: GrantFiled: June 7, 1995Date of Patent: February 10, 1998Assignee: Institute of Materia Medica, an institute of the Chinese Academy of Medical SciencesInventors: Rui Han, Shi-Ping Xu
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Patent number: 5703113Abstract: The invention relates to benzopyran compounds of formula (I) possessing pharmacological activity, as well as to pharmaceutical compositions containing the compounds of formula (I) and processes for the preparation thereof.Type: GrantFiled: November 8, 1995Date of Patent: December 30, 1997Assignee: Alkaloida Vegyeszeti GyarInventors: Tibor Eszenyi, Peter Sebok, Laszlo Frank, Gyula Papp, Tibor Timar, Tamas Bartik
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Patent number: 5696157Abstract: The present invention describes 7-aminocoumarin dyes that are substituted one or more times at the 3-, 6- and/or 8-positions by a sulfonic acid or a salt of a sulfonic acid, said dyes being useful as fluorescent probes or in the preparation of enzyme substrates, caged probes, or adducts with reducing sugars. The dyes of the invention optionally possess a reactive group useful for preparing fluorescent conjugates, which conjugates and methods for their preparation are described herein.Type: GrantFiled: November 15, 1996Date of Patent: December 9, 1997Assignee: Molecular Probes, Inc.Inventors: Hui-Ying Wang, Wai-Yee Leung, Fei Mao
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Patent number: 5686485Abstract: The present invention relates to EI-1941 compounds having interleukin-1 production inhibitory activity which are represented by the formula: ##STR1## wherein either of R.sup.1 and R.sup.2 is hydrogen and the other is hydroxy, or R.sup.1 and R.sup.2 together represent oxygen; and R.sup.3 is hydroxy and R.sup.4 is hydrogen, or R.sup.3 and R.sup.4 together represent --0--.Type: GrantFiled: October 9, 1996Date of Patent: November 11, 1997Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Takeo Tanaka, Hidemasa Kondo, Fumito Koizumi, Hiroki Ishiguro, Mayumi Yoshida, Katsuhiko Ando, Yuzuru Matsuda
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Dual purposed diagnostic/therapeutic agent having a tri-iodinated benzoyl group linked to a coumarin
Patent number: 5665330Abstract: The invention provides a novel compound having the structure ##STR1## wherein R is alkyl and R1, R2, R3 and R4 are each independently OCH3, H or I and n is 0 or 1 and m is 0 or 1.The compound is useful in a method of treating mammals either therapeutically or imaging mammals for diagnostic purposes. Useful therapeutic areas are in treating lymph nodes and tumors and diagnostic treatment is applicable to lymph nodes, tumors and in blood pool imaging. It is particularly advantageous to link an insoluble carrier molecule with a therapeutic or imaging agent to form the structure above. This makes the conjugate insoluble and thus amenable to forming nanoparticles.Type: GrantFiled: February 8, 1995Date of Patent: September 9, 1997Assignee: Nano Systems LLCInventor: Sui-Ming Wong -
Patent number: 5624951Abstract: A compound of formula V: ##STR1## wherein all the R's groups are as defined in the specification, is useful in the treatment of bacterial infections.Type: GrantFiled: March 1, 1995Date of Patent: April 29, 1997Assignee: Pfizer Inc.Inventors: Bingwei Yang, Joyce Sutcliffe, Chris J. Dutton
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Patent number: 5574062Abstract: The present invention provides compounds having 12-lipoxygenase inhibitory effect and medicines inhibiting 12-lipoxygenase selectively, and relates to novel coumarin derivatives and medicines containing the compounds as effective ingredients. Furthermore, this invention relates to compounds capable of converting to compounds inhibiting 12-lipoxygenase activities selectively according to the cleavage of modified moieties in vivo and medicines inhibiting 12-lipoxygenase selectively, and relates to novel coumarin derivatives having acyl groups as modified moieties and medicines containing the compounds as effective ingredients. The compounds of the present invention can inhibit 12-lipoxygenase strongly and selectively, and being useful as medicines for preventing and treating various circulatory diseases such as arteriosclerosis and vasospasm and for preventing of the metastasis of some kinds of cancers, and show low toxicity and few side effects.Type: GrantFiled: December 13, 1994Date of Patent: November 12, 1996Assignee: Morinaga Milk Industry Co., Ltd.Inventors: Koichi Hashimoto, Akio Yamada, Hirokazu Hamano, Shigehiro Mori, Hisako Moriuchi
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Patent number: 5552437Abstract: Compounds having the Formula I:R.sup.1 R.sup.2 C(OR.sup.3)--Ar.sup.1 --X--Ar.sup.2 --Ar.sup.3Ire inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.Type: GrantFiled: October 27, 1994Date of Patent: September 3, 1996Assignee: Merck Frosst Canada, Inc.Inventors: Daniel Delorme, Daniel Dub e, Yves Ducharme, Erich L. Grimm, Richard Friesen, Carole Lepine
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Patent number: 5489697Abstract: A method for preparing (.+-.)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. Useful intermediates for preparing (.+-.)-calanolide A and its derivatives are also provided.According to the disclosed method, chromene 4 intermediate was reacted with acetaldehyde diethyl acetal in the presence of an acid catalyst with heating to produce chromanone 7. Reduction of chromene 7 with sodium borohydride, in the presence of cerium trichloride, produced (.+-.)-calanolide A, which was purified chromatographically.Type: GrantFiled: August 3, 1994Date of Patent: February 6, 1996Assignee: MediChem Research, Inc.Inventors: William A. Boulanger, Michael T. Flavin, Alla Kucherenko, Abram K. Sheynkman
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Patent number: 5484951Abstract: Unsubstituted or substituted 5-iodo-6-amino-1,2-benopyrones and their metabolites are potent, selective and non-toxic inhibitors and suppressants of cancer growth and viral infections in a mammalian host. The compounds are particularly useful for treatment and suppression of tumors and viruses associated with AIDS, herpetic episodes and cytomegaloviral infections. The methods of treatment of tumorigenic and viral diseases by 5-iodo-6-amino-1,2-benzopyrones and/or its metabolites are described.Type: GrantFiled: October 19, 1990Date of Patent: January 16, 1996Assignee: Octamer, IncorporatedInventors: Ernest Kun, Jerome Mendeleyev
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Patent number: 5480907Abstract: Aromatic amide compounds of the formula: ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 are independently hydrogen, a lower alkyl or lower alkoxy group; Ar is an optionally substituted aromatic group; the groupC - - - -Cis C.dbd.C or HC--CH; X is hydrogen, CH.sub.2 COOH or CH.sub.2 CONHAr; and Y is hydrogen or COOH; provided that when X is CH.sub.2 COOH or Y is COOH, the COOH may be taken together with the adjacent hydroxy group on the benzene ring to form a lactone ring by dehydration, a quinone form thereof or a pharmaceutically acceptable salt thereof have potent nerve growth factor (NGF) secretion inducing activity, and are thus useful as a drug for the treatment or prophylaxis of degenerative nervous system disorders such as senilic dementis, and Alzheimer's disease.Type: GrantFiled: May 13, 1992Date of Patent: January 2, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Kyozo Hayashi, Munekazu Iinuma
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Patent number: 5441974Abstract: This invention relates to compounds having the following formula ##STR1## wherein Z is a lactone or a lactone which is fused to a benzene ring which are useful in the inhibition of platelet aggregation. This invention also relates to pharmaceutical compositions of such phenyl amidines derivatives.Type: GrantFiled: May 25, 1994Date of Patent: August 15, 1995Assignee: G. D. Searle & Co.Inventors: Philippe R. Bovy, Thomas E. Rogers, Masateru Miyano, Joseph G. Rico
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Patent number: 5414006Abstract: Arylalkoxythiocoumarins of the formula ##STR1## where R.sup.1 and R.sup.2 are each, independently of one another, hydrogen, C.sub.1 -C.sub.5 -alkyl, trifluoromethyl, phenyl or halogen, or together are a C.sub.3 -C.sub.5 -alkylene chain, andX is oxygen or sulfur,R.sup.3 is C.sub.1 -C.sub.5 -alkyl or halogen,n is an integer from 0 to 3,R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl andAr is phenyl, which can be mono- or disubstituted by halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, nitro, cyano, trifluoromethyl or a combination of these substituents or is a heteraromatic ring which has from one to three heteroatoms which can, independently of one another, be N, O or S, and which can be substituted by C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.4 -alkoxy-substituted C.sub.1 -C.sub.6 -alkyl, 5-6-membered oxacycloalkyl, benzyl, C.sub.1 -C.sub.5 -alkoxycarbonyl, perfluoro-C.sub.1 -C.sub.Type: GrantFiled: October 14, 1993Date of Patent: May 9, 1995Assignee: BASF AktiengesellschaftInventors: Beatrice Rendenbach-Mueller, Ulrich Karl, Harald Weifenbach
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Patent number: 5399561Abstract: Compounds of the formula ##STR1## where R.sub.1 and R.sub.2 are hydrogen, lower alkyl of 1-6 carbons, or halogen; R.sub.3 is hydrogen, lower alkyl of 1-6 carbons, halogen, OR.sub.11, SR.sub.11, OCOR.sub.11, SCOR.sub.11, NH.sub.2, NHR.sub.11, N(R.sub.11).sub.2, NHCOR.sub.11 or NR.sub.11 COR.sub.11 ; X is O, S or NR' where R' is hydrogen or lower alkyl of 1-6 carbons; Y is phenyl or a heteroaryl group selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl and oxazolyl; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub. 12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.Type: GrantFiled: January 7, 1994Date of Patent: March 21, 1995Assignee: Allergan, Inc.Inventor: Roshantha A. Chandraratna
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Patent number: 5334740Abstract: Cyclohexanetriol derivatives represented by the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are the same or different, and each denotes a hydrogen atom or a protecting group of a hydroxyl group,X denotes an oxygen atom, .dbd.CHCH.sub.2 OR.sup.4, .dbd.CHCHO or .dbd.CHCO.sub.2 R.sup.5, Y denotes a hydrogen atom and Z denotes --OR.sup.6, or Y and Z together form a single bond; or X and Z together form .dbd.NO--, .dbd.CHCH(OR.sup.7)O-- or .dbd.CHCO.sub.2 -- and Y is a hydrogen atom, R.sup.4 and R.sup.6 denote a hydrogen atom or a protecting group of a hydroxyl group respectively, R.sup.5 denotes a lower alkyl group, and R.sup.7 denotes a hydrogen atom or a lower alkyl group.Said derivatives are useful as synthetic intermediates of 1-hydroxyvitamin D derivatives.Type: GrantFiled: March 13, 1992Date of Patent: August 2, 1994Assignee: Kurary Co., Ltd.Inventors: Takashi Takahashi, Manzo Shiono
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Patent number: 5281721Abstract: This invention relates to a novel class of heterocyclic compounds useful for selectively inhibiting elastase, selectively inhibiting chymotrypsin-like enzymes, selectively inhibiting trypsin-like enzymes, or for generally inhibiting serine proteases of all classes.Type: GrantFiled: April 28, 1992Date of Patent: January 25, 1994Assignee: Georgia Tech Research CorporationInventors: James C. Powers, Wade Harper
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Patent number: 5254595Abstract: Aryloxypropanolaminotetralins with beta-antagonist activity of the formula ##STR1## wherein R is hydrogen, hydroxy or methoxy and Ar is an optionally substituted aromatic or heteroaromatic group, in optically active or inactive form as well as their acid addition salts are described.A process for their preparation and pharmaceutical compositions containing the compounds of formula (i) or their pharmaceutically acceptable acid addition salts, are also described.Type: GrantFiled: January 9, 1992Date of Patent: October 19, 1993Assignee: Elf SanofiInventors: Umberto Guzzi, Marco Baroni, Sergio Boveri, Luciano Manara, Alberto Bianchetti
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Patent number: 5247099Abstract: A process for synthesis of a compound of the formula: ##STR1## said process comprising the steps of (a) reacting 4-bromomethyl-7-methoxy coumarin with a malonic ester under conditions sufficient to achieve condensation of the ester to give the monoalkylated (2-bis(carbalkoxy)-2-R.sub.1 -1-ethyl) derivative; (b) removing one of the carbalkoxy groups from the product of step (a); (c) demethylation of the product of step (b) to give the 7-hydroxycoumarin compound; and (d) chemically modifying the remaining ester to yield a desired R.sub.2.Type: GrantFiled: May 21, 1991Date of Patent: September 21, 1993Assignee: Abbott LaboratoriesInventor: Joseph E. Celebuski
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Patent number: 5216176Abstract: A photochemotherapeutic compound of the formula ##STR1## wherein (i) n is zero, W is a (C.sub.1-16) alkyl, alkenyl, or alkynyl linear or branched chain hydrocarbon, having no more than four O, N, or S atoms in or attached to the chain; or(ii) n is 1, W is CR or CR.sub.2, and R, R', and R" are independently H or CH.sub.3 ; or(iii) N is 2, W is CR or CR.sub.2, and R, R', and R" are independently H or CH.sub.3 ; andA, B, C, and D are independently selected from hydrogen, alkyl, aryl, halogen, amino, aminoalkyl, nitro, alkoxy, aryloxy, hydroxy, carboxy, haloalkyl, or haloalkoxy, particularly compounds of the foregoing structure in which W is a charged substiuent and n=0 or 1.Type: GrantFiled: December 21, 1990Date of Patent: June 1, 1993Assignee: Lehigh UniversityInventors: Ned D. Heindel, Michele C. Jetter nee Siller, Jeffrey D. Laskin, Michael A. Gallo
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Patent number: 5208350Abstract: This invention relates to fluorescent 7-hydroxy coumarin compounds with substitutions in the 4 position having a length greater than one carbon atom. The compounds thus are related to 4-methylumbelliferone (7-hydroxy-4-methyl coumarin, or 4-MU), the detectable label used in the IM.sub.x .RTM. instrument assays (Abbott Laboratories, Abbott Park, Ill.). The substitutions in the 4 position are branched and include functional groups for coupling to biological molecules.Type: GrantFiled: May 21, 1991Date of Patent: May 4, 1993Assignee: Abbott LaboratoriesInventors: Stanley R. Bouma, Joseph E. Celebuski
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Patent number: 5192799Abstract: Amine represented by the following formula (1), or their acid addition salts or their quaternary ammonium salts. ##STR1## The amines of formula (1) or their pharmaceutically acceptable acid addition salts or quaternary ammonium salts are useful for the treatment and prevention of heart diseases of animals, particularly arrhythima, myocardial infarction, angina pectoris and heart failure and psychoneurological diseases.Type: GrantFiled: June 5, 1992Date of Patent: March 9, 1993Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Ikuo Tomino, Masaharu Ishiguro, Takumi Kitahara, Keiichi Yokoyama, Noriaki Kihara, Joji Kamiya, Kanji Yoshihara, Masaaki Ishii, Akira Mizuchi, Kazutoshi Horikomi, Akira Awaya, Takuo Nakano