Carbon Bonded Directly To The Phosphorus Patents (Class 558/189)
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Patent number: 8426629Abstract: Disclosed is a process for producing a phosphine derivative from a phosphine oxide derivative, which comprises the following steps: (I) mixing a phosphine oxide derivative represented by formula (1) with a chlorinating agent in a polar organic solvent to cause the reaction between these components; and (II-1) adding a salt of a metal having an ionization tendency equal to or lower than that of aluminum to the reaction mixture and carrying out the reductive reaction in the presence of aluminum or (II-2) subjecting the reaction mixture to electrolytic reduction, thereby producing a phosphine derivative represented by formula (2). ArnR3-nP?O (1) ArnR3-nP (2) In formulae (1) and (2), Ar represents an aryl group such as a phenyl group, a phenyl group having a substituent, a heteroaromatic ring group, and a heteroaromatic ring group having a substituent; R represents an aliphatic hydrocarbon group or an aliphatic hydrocarbon group having a substituent; and n represents an integer of 0 to 3.Type: GrantFiled: May 14, 2009Date of Patent: April 23, 2013Assignees: National University Corporation Okayama University, Asahi Kasei Chemicals Corporation, Hokko Chemical Industry Co., Ltd.Inventors: Hideo Tanaka, Manabu Kuroboshi, Tomotake Yano, Masakatsu Hoshino, Hiromu Kawakubo
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Patent number: 8273886Abstract: The invention is directed to a radiation sensitive compound comprising a surface binding group proximate to one end of the compound for attachment to a substrate, and a metal binding group proximate to an opposite end of the compound. The metal binding group is not radiation sensitive. The radiation sensitive compound also includes a body portion disposed between the surface binding group and the metal binding group, and a radiation sensitive group positioned in the body portion or adjacent to the metal binding group. The surface binding group is capable of attaching to a substrate selected from a metal, a metal oxide, or a semiconductor material.Type: GrantFiled: August 27, 2008Date of Patent: September 25, 2012Assignee: International Business Machines CorporationInventors: Ali Afzali-Ardakani, Cherie R. Kagan, Laura L. Kosbar, Sally A. Swanson, Charan Srinivasan
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Patent number: 7795463Abstract: Disclosed is a process for preparing a compound of the following formula (2): including the steps of reacting a compound of the following formula (4): with trityl chloride to prepare trityloxy-acetic acid ethyl ester of the following formula (8): reacting the compound of formula (8) with ethyl magnesium halide to prepare 1-trityloxymethyl-cyclopropanol of the following formula (9): combining the 1-trityloxymethyl-cyclopropanol of formula (9) with diisopropylbromo-methylphosphonate in a solvent in the presence of a base to prepare (1-trityloxymethyl-cyclopropoxymethyl)-phosphonic acid diisopropyl ester of the following formula (10): as a solid form, and converting the trityl group of the compound of formula (10) into a hydroxyl group.Type: GrantFiled: June 27, 2005Date of Patent: September 14, 2010Assignee: LG Life Sciences Ltd.Inventors: Suk-Kyoon Yoon, Kun-Hye Nam, Sang-Who Lee, Won-Kyo Joung, Sang-Chul Choi, Ki-Kon Lee
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Patent number: 7723319Abstract: The present invention relates to an acyclic nucleoside phosphonate derivative which is useful as an antiviral agent (particularly, against hepatitis B virus), pharmaceutically acceptable salts, stereoisomers, and a process for the preparation thereof.Type: GrantFiled: September 9, 2009Date of Patent: May 25, 2010Assignee: LG Life Sciences Ltd.Inventors: Dong-Gyu Cho, Jae-Hong Lim, Jae-Taeg Hwang, Woo-Young Cho, Hyun-Sook Jang, Chang-Ho Lee, Tae-Saeng Choi, Chung-Mi Kim, Yong-Zu Kim, Tae-Kyun Kim, Seung-Joo Cho, Gyoung-Won Kim, Jong-Ryoo Choi, Jeong-Min Kim, Kee-Yoon Roh
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Patent number: 7605147Abstract: The present invention relates to an acyclic nucleoside phosphonate derivative represented by the following formula (1): in which represents single bond or double bond, R1, R2, R3, R7 and R8 are defined herein, Y represents —O—, —S—, —CH(Z)-, ?C(Z)-, —N(Z)-, ?N—, or —SiH(Z)-, wherein Z represents hydrogen, hydroxy or halogen, or represents C1-C7-alkyl, C1-C5-alkoxy, allyl, hydroxy-C1-C7-alkyl, C1-C7-aminoalkyl or phenyl, Q represents a group having the following formula: wherein X1, and X2 independently of one another represent hydrogen, amino, hydroxy or halogen, or represent C1-C7-alkyl, C1-C5-alkoxy, allyl, hydroxy-C1-C7-alkyl, phenyl or phenoxy each of which is optionally substituted by nitro or C1-C5-alkoxy, or represent C6-C10-arylthio which is optionally substituted by nitro, amino, C1-C6-alkyl or C1-C4-alkoxy, or represent C6-C12-arylamino, C1-C7-alkylamino, di(C1-C7-alkyl)amino, C3-C6-cycloalkylamino or a structure of wherein n denotes an integer of 1 or 2 and Y1 represents O, CH2 or N—Type: GrantFiled: June 20, 2006Date of Patent: October 20, 2009Assignee: LG Life Sciences Ltd.Inventors: Dong-Gyu Cho, Jae-Hong Lim, Jae-Taeg Hwang, Woo-Young Cho, Hyun-Sook Jang, Chang-Ho Lee, Tae-Saeng Choi, Chung-Mi Kim, Yong-Zu Kim, Tae-Kyun Kim, Seung-Joo Cho, Gyoung-Won Kim, Jong-Ryoo Choi, Jeong-Min Kim, Kee-Yoon Roh
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Patent number: 7157448Abstract: The present invention relates to a nucleoside phosphonate derivative represented by formula (1): pharmaceutically acceptable salts, and stereoisomers. This nucleoside phosphonate derivative is useful as an antiviral agent, particularly, against hepatitis B virus. Also disclosed are processes for the preparation of the nucleoside phosphonate derivative. Also disclosed are methods treating hepatitis B by administering a nucleoside phosphonate derivative of formula (1).Type: GrantFiled: January 18, 2002Date of Patent: January 2, 2007Assignee: LG Life Sciences Ltd.Inventors: Jong-Ryoo Choi, Jeong-Min Kim, Kee-Yoon Roh, Dong-Gyu Cho, Jae-Hong Lim, Jae-Taeg Hwang, Woo-Young Cho, Hyun-Sook Jang, Chang-Ho Lee, Tae-Saeng Choi, Chung-Mi Kim, Yong-Zu Kim, Tae-Kyun Kim, Seung-Joo Cho, Gyoung-Won Kim
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Patent number: 6653296Abstract: Resolved enantiomers of the formula (IA) and (IB) wherein B is a purine or pyrimidine base or aza and/or deaza analogs thereof are useful in antiviral pharmaceutical compositions to treat retroviral infections.Type: GrantFiled: February 2, 1995Date of Patent: November 25, 2003Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Antonin Holy, Hana Dvorakova, Erik Desire Alice De Clercq, Jan Marie Rene Balzarini
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Patent number: 6562992Abstract: The optical material in accordance with the present invention contains a specific phosphonate monoester compound such as monoethyl 3-methoxy butyl phosphonate, and a metal ion such as a copper ion or rare-earth metal ion. They may be contained in a solvent or resin. The use of such a specific phosphonate monoester compound improves the compatibility with a resin, whereby the metal ion can favorably be dispersed into the resin. Consequently, spectral characteristics can be improved when the optical member is formed into a resin-made optical member.Type: GrantFiled: August 24, 2001Date of Patent: May 13, 2003Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Naoki Hayashi, Shigeru Mizusawa, Tomoyoshi Koizumi, Katsuichi Machida
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Patent number: 5922696Abstract: Disclosed are novel unsaturated phosphonate derivatives of certain purines or pyrimidines useful as antiviral agents, methods useful for their preparation and use of these compounds as antiviral agents effective against DNA viruses, retroviruses and viruses involved in tumor formation.Type: GrantFiled: August 10, 1998Date of Patent: July 13, 1999Assignee: Merrell Pharmaceuticals Inc.Inventors: Patrick Casara, Jean-Fran.cedilla.ois Nave, Serge Halazy
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Patent number: 5817647Abstract: Disclosed are novel unsaturated acetylene phosphonate derivatives of certain purines or pyrimidines useful as antiviral agents, methods useful for their preparation and use of these compounds as antiviral agents effective against DNA viruses, retroviruses and viruses involved in tumor formation.Type: GrantFiled: November 17, 1995Date of Patent: October 6, 1998Assignee: Merrell Pharmaceuticals Inc.Inventors: Patrick Casara, Jean-Fran.cedilla.ois Nave, Serge Halazy
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Patent number: 5728686Abstract: Alkylxanthine phosphonates and alkylxanthine phosphine oxides and their use as pharmaceuticalsA compound of the formula ##STR1## where R.sup.1 and R.sup.3 are identical or different and at least one of the radicals R.sup.1 and R.sup.3 is a radical of the formula XI ##STR2## in which E is a covalent bond or a (C.sub.1 -C.sub.Type: GrantFiled: October 31, 1996Date of Patent: March 17, 1998Assignee: Hoechst AktiengesellschaftInventors: Gunter Billen, Ismahan Okyayuz-Baklouti, Hiristo Anagnostopulos, Stefan Mullner
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Patent number: 5650510Abstract: A series of compounds of Formula I which have anti-tumor activity, and are useful in treating viral infections, their compositions and use. ##STR1## In Formula I B is a purine or pyrimidine base; alk.sub.1 alk.sub.2 and alk.sub.3 are chemical bonds or alkylene groups; Q is hydrogen or hydroxyl; and R.sub.1 -R.sub.4 are hydrogen or alkyl.Type: GrantFiled: January 31, 1992Date of Patent: July 22, 1997Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Sciences of the Czech Republic, Rega Stichting v.z.w.Inventors: Robert W. Webb, II, Joanne J. Bronson, John C. Martin
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Patent number: 5574025Abstract: The compounds disclosed inhibit the prenylation of several proteins. These compounds are potent inhibitors of famesyl-protein transferase and geranylgeranyl-protein transferase. Further contained in this invention are chemotherapeutic compositions containing these prenyl-transferase inhibitors and methods for their production.Type: GrantFiled: October 26, 1994Date of Patent: November 12, 1996Assignee: Merck & Co., Inc.Inventors: Neville J. Anthony, Robert P. Gomez, Charles A. Omer
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Patent number: 5532225Abstract: Acyclic purine phosphonate nucleotide analogs useful to treat herpes viral infections are provided in enantiomerically pure form. These antiviral agents have the structural formula (Ia) or (Ib) ##STR1## and may be in acid, salt or ester form. Such compounds may also be dehydrated to provide antiviral agents in cyclic form. Pharmaceutical compositions are provided containing the antiviral agents, as is a chiral synthesis which may be used to prepare the agents in enantiomerically pure form or as a racemic mixture.Type: GrantFiled: July 31, 1992Date of Patent: July 2, 1996Assignee: SRI InternationalInventors: Elmer J. Reist, Beatrice Ruhland-Fritsch, Pricilla A. Sturm
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Patent number: 5386030Abstract: The present invention concerns nucleotide analogs and their compositions and use. In particular it relates to novel (phosphonomethoxy) methoxy purine/pyrimidine derivatives.Type: GrantFiled: February 11, 1993Date of Patent: January 31, 1995Assignees: Institute of Organic Chemistry and Biochemistry of the Academy of Science of the Czech Republic, Rega Stichting v.z.w.Inventors: Choung U. Kim, John C. Martin, Bing Y. Luh, Peter F. Misco
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Patent number: 5312953Abstract: Polyether bis-phosphonic acid compounds are disclosed which have the formula (HO).sub.2 OP--R--(OR').sub.n --OR--PO(OH).sub.2 where R is selected from the group consisting of methylene and ethylene, R' is selected from the group consisting of ethylene and ethylene substituted with one or more methyl groups, and n is an integer from 1 to 4, water soluble salts thereof, and esters thereof with alkyl groups having from 1 to 6 carbon atoms. Also disclosed is a novel preparation of these compounds by reacting hydroxyalkylphosphonic acid dialkyl ester compounds with 2-benzyloxyalkyl organic sulfonates; reacting the intermediate formed therefrom with hydrogen or a hydrogen source; reacting the intermediate formed therefrom with a hydrogen ion acceptor and certain sulfonyl chlorides; and reacting the intermediate formed therefrom with hydroxyalkylphosphonic acid dialkyl ester compounds to form a polyether bis-phosphonic acid compound which may be hydrolyzed to form the polyether bis-phosphonic acid.Type: GrantFiled: August 17, 1993Date of Patent: May 17, 1994Assignee: W. R. Grace & Co.-Conn.Inventors: Charles G. Carter, Ranjit Kumar
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Patent number: 5266722Abstract: Polyether bis-phosphonic acid compounds are disclosed which have the formula (HO).sub.2 OP--R--(OR').sub.n --OR--PO(OH).sub.2 where R is selected from the group consisting of methylene and ethylene, R' is selected from the group consisting of ethylene and ethylene substituted with one or more methyl groups, and n is an integer from 1 to 4, water soluble salts thereof, and esters thereof with alkyl groups having from 1 to 6 carbon atoms.Type: GrantFiled: November 9, 1988Date of Patent: November 30, 1993Assignee: W. R. Grace & Co.-Conn.Inventors: Charles G. Carter, Ranjit Kumar
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Patent number: 5242908Abstract: The use of a compound of the formula I ##STR1## in which V is an alkyl group, fluorine, chlorine, bromine, or iodine, n is an integer from 1 to 5, W is an alkyl, alkenyl, alkynyl or alkoxy group, cyanide, nitro, carboxyl, hydrogen or a cycloalkyl, aryl, aralkyl or carboalkoxy group, R.sup.1 and R.sup.2 are an alkyl, alkenyl, alkynyl, cycloalkyl or halogenoalkyl group, sodium, potassium, calcium, magnesium, aluminum, lithium, ammonium, triethylammonium or hydrogen, R.sup.1 and R.sup.2 together form a cyclic diester, R.sup.3 and R.sup.4 are an alkyl, alkenyl, alkynyl, carboalkoxy, cycloalkyl or alkoxy group, hydrogen, fluorine, chlorine, bromine or iodine and X, Y and Z are oxygen or sulfur, for the treatment of diseases caused by DNA viruses or RNA viruses is described.Type: GrantFiled: February 1, 1991Date of Patent: September 7, 1993Assignee: Hoechst AktiengesellschaftInventors: Anuschirwan Peyman, Eugen Uhlmann, Karlheinz Budt, Jochen Knolle, Irvin Winkler, Matthias Helsberg
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Patent number: 5225584Abstract: A novel synthesis of compounds having the formula: ##STR1## wherein T is a stabilizing spiro-linked polycycloalkylidene group, R.sup.3 is a C.sub.1 -C.sub.20 alkyl, aralkyl or heteroatom containing group, Y is an aromatic fluorescent chromophore, and Z is a cleavable group which, when cleaved, induces decomposition of the dioxetane ring and emission of optically detectable light, is disclosed. A tertiary phosphorous acid alkyl ester of the formula:(R.sup.1 O).sub.3 Pwherein R.sup.1 is a lower alkyl group, is reacted with an aryl dialkyl acetal produced by reacting a corresponding aryl aldehyde with an alcohol of the formula:R.sup.3 OHwherein R.sup.3 is as defined above, to produce a 1-alkoxy-1-arylmethane phosphonate ester of the formula: ##STR2## reacting the phosphonate with base to produce a phosphonate-stabilized carbanion, reacting the carbanion with a ketone of the formula:T.dbd.Type: GrantFiled: April 3, 1991Date of Patent: July 6, 1993Assignee: Tropix, Inc.Inventors: Edwards Brooks, Juo Rhou-Rong
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Patent number: 5177239Abstract: A method is provided for preparing a phosphonic acid ester having the structure ##STR1## wherein R.sup.1 is farnesyl or a derivative or analog thereof, and R.sup.2 is lower alkyl, by treating a farnesyl halide R.sup.1 Hal(Hal.dbd.Cl,Br,I) with an alkoxide of the structure ##STR2## wherein M is an alkali metal and R.sup.2c is lower alkyl. The resulting phosphonic acid ester is an intermediate in preparing a squalene synthetase inhibitor which is used for inhibiting cholesterol biosynthesis.Type: GrantFiled: July 17, 1989Date of Patent: January 5, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: Janak Singh, Richard H. Mueller
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Patent number: 5166198Abstract: A compound of formula (I), or a pharmaceutically acceptable salt thereof: ##STR1## wherein R.sub.1 is hydroxy or amino;R.sub.2 is hydrogen or amino;R.sub.3 is hydrogen, hydroxymethyl or acyloxymethyl;R.sub.4 is hydrogen or (when R.sub.3 =H and Z is a bond or CH.sub.2) hydroxy, acyloxy, hydroxymethyl or acyloxymethyl;Z is a bond, or a group CHR.sub.8 wherein R.sub.8 is hydrogen, or (when R.sub.3 =R.sub.4 =H), R.sub.8 is hydroxy, acyloxy, hydroxymethyl or acyloxymethyl;R.sub.5 is a group of formula: ##STR2## wherein R.sub.6 and R.sub.7 are independently selected from hydrogen,C.sub.1-6 alkyl and optionally substituted phenyl.Type: GrantFiled: March 28, 1990Date of Patent: November 24, 1992Assignee: Beecham p.l.c.Inventors: Michael R. Harnden, David M. Duckworth, Halina T. Serafinowska
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Patent number: 5153347Abstract: Novel angiotensin II receptor antagonists of the formula ##STR1## wherein X, X.sub.1, X.sub.2, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined herein, are disclosed. These compounds are useful, for example, in the treatment of hypertension, congestive heart failure and cardiac hypertrophy.Type: GrantFiled: January 31, 1991Date of Patent: October 6, 1992Assignee: E. R. Squibb & Sons, Inc.Inventor: John E. Lloyd
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Patent number: 5108994Abstract: Compounds of formula (I), and pharmaceutically acceptable salts thereof: ##STR1## wherein R.sub.1 is hydroxy or amino;R.sub.2 is hydrogen or amino;R.sub.3 is hydrogen, hydroxymethyl or acyloxymethyl;R.sub.4 is a group of formula: ##STR2## wherein R.sub.5 and R.sub.6 are independently selected from hydrogen, C.sub.1-6 alkyl and optionally substituted phenyl; orR.sub.3 and R.sub.4 together are: ##STR3## wherein R.sub.6 is as defined above;having antiviral activity, processes for their preparation and their pharmaceutical use.Type: GrantFiled: May 23, 1990Date of Patent: April 28, 1992Assignee: Beecham Group p.l.c.Inventors: Michael R. Harnden, Leslie J. A. Jennings
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Patent number: 5107011Abstract: Compounds which are inhibitors of cholesterol biosynthesis (by inhibiting de novo squalene biosynthesis), and thus are useful as hypocholesterolemic agents and antiatherosclerotic agents, are provided which have the structure ##STR1## wherein R.sup.2 is a metal ion, lower alkyl or H; R.sup.3 is a metal ion or lower alkyl;R is R.sup.1 --(CH.sub.2).sub.n --, R.sup.1 --(CH.sub.2).sub.m --O-- or R.sup.1 --(CH.sub.2).sub.m --OCH.sub.2 --, wherein n is 1 to 4 and m is 0 to 3, andR.sup.1 is R.sup.5 --Q.sup.1 --Q.sup.2 --Q.sup.3 -- wherein R.sup.5, Q.sup.1, Q.sup.2 and Q.sup.3 are as defined herein.New intermediates, new methods of preparation and a method for using such compounds to inhibit cholesterol biosynthesis are also provided.Type: GrantFiled: February 5, 1991Date of Patent: April 21, 1992Assignee: E. R. Squibb & Sons, Inc.Inventor: Scott A. Biller