Divalent Chalcogen Double Bonded Directly To Pentavalent Phosphorus Patents (Class 558/161)
  • Patent number: 5482638
    Abstract: Addition products of monoepoxides or diepoxides of mono- or polyunsaturated monocyclic or bicyclic hydrocarbons and dithiophosphoric acids, a process for the production of the adducts from the corresponding dithiophosphoric acids and epoxides and the use of the addition products as lubricant additives in lubricants based on mineral oils or native oils.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: January 9, 1996
    Assignee: Rhein Chemie Rheinau GmbH
    Inventors: Thomas Dimmig, Gunter Jager, Thomas Petri
  • Patent number: 5453524
    Abstract: The present invention provides a phosphorus-containing isoprenoid derivative represented by the following general formula (I) or a pharmacologically acceptable salt thereof, which is useful as a preventive and therapeutic agent for diseases for which a squalene synthetase inhibiting action is efficacious: ##STR1## wherein R.sup.1 and R.sup.2 each represent a hydrogen atom, a lower alkyl, cycloalkyl, alkenyl or alkynyl group, an aryl group which may be substituted, an arylalkyl group in which the aryl group may be substituted, or a heteroaryl or heteroarylalkyl group: R.sup.3 and R.sup.4 each represent a hydrogen atom, a lower alkyl group or an alkali metal; Y represents a group represented by the formula: ##STR2## (wherein R.sup.5 and R.sup.6 each represent a hydrogen atom, a lower alkyl group or an alkali metal or a group represented by the formula: --CO.sub.2 R.sup.7 (wherein R.sup.7 represents a hydrogen atom, a lower alkyl group or an alkali metal); Z represents a group represented by the Formula: --(CH.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: September 26, 1995
    Assignee: Eisai Co., Ltd.
    Inventors: Katsuya Tagami, Ichirou Yoshida, Naoki Kobayashi, Yoshio Fukuda, Yoshihito Eguchi, Makoto Nakagawa, Hironobu Hiyoshi, Hironori Ikuta, Makoto Kaino, Kenji Hayashi, Issei Ohtsuka, Shinya Abe, Shigeru Souda
  • Patent number: 5451401
    Abstract: Polyphosphonic acid ester compounds with flavorant, coolant and/or sweetener components, and tartar, plaque and/or calculus control compositions with improved taste comprising one or more polyphosphonic acid ester compounds are described.
    Type: Grant
    Filed: September 29, 1993
    Date of Patent: September 19, 1995
    Assignee: The Procter & Gamble Company
    Inventors: Kim W. Zerby, Jeffrey C. Hayes
  • Patent number: 5442085
    Abstract: A method of making a monomer of tetraalkyl vinylidene-1, 1-diphosphonate. The monomer is manufactured by combining an aqueous secondary amine solution with a formaldehyde and a tetra (alkyl) methylene diphosphonate. The resulting mixture is maintained at a pH above about 6 and refluxed for two hours to enable reaction to produce the monomer of tetraalkyl vinylidene-1, 1-diphosphonate. The product monomer is then purified to produce the final end product.
    Type: Grant
    Filed: October 5, 1993
    Date of Patent: August 15, 1995
    Assignee: The University of Tennessee Research Corporation
    Inventor: Spiro D. Alexandratos
  • Patent number: 5438048
    Abstract: Novel pharmacologically active methylenebisphosphonates having formula (I) wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently are straight or branched, optionally unsaturated C.sub.1 -C.sub.10 -alkyl, optionally unsaturated C.sub.3 -C.sub.10 -cycloalkyl, aryl, aralkyl, silyl SiR.sub.3 or hydrogen, whereby in formula (I) at least one of the groups R.sup.1, R.sup.2, R.sup.3 or R.sup.4 is hydrogen and at least one of the groups is different from hydrogen, Q.sup.1 is hydrogen, hydroxyl, halogen, amino NH.sub.2, or OR', wherein R' is C.sub.1 -C.sub.4 -lower alkyl or acyl, Q.sup.2 is straight or branched, optionally unsaturated C.sub.1 -C.sub.10 -alkyl, -hydroxyalkyl or -aminoalkyl, whereby the oxygen may, as a substituent, contain one group or the nitrogen as a substituent may contain one or two groups, which are C.sub.1 -C.sub.4 -lower alkyl or acyl, or the two substituents of the nitrogen form together with the nitrogen atom a saturated, partly saturated or an aromatic heterocyclic ring, or Q.sup.
    Type: Grant
    Filed: October 20, 1993
    Date of Patent: August 1, 1995
    Assignee: Leiras Oy
    Inventors: Hannu Nikander, Marjaana Heikkila-Hoikka, Esko Pohjala, Hannu Hanhijarvi, Leena Lauren
  • Patent number: 5428181
    Abstract: A compound represented by the general formula: ##STR1## wherein A-O-denotes a residue of a compound having an estrogenic activity; R.sub.1 denotes H or a C.sub.1 -C.sub.6 alkyl group; X denotes a single bond, a C.sub.1 -C.sub.10 alkylene group or a group of the formula ##STR2## wherein R.sub.2 denotes H or a C.sub.1 -C.sub.5 alkyl group; Z denotes a nitro group or a halogen; n is an integer of 3 to 12; k is an integer of 1 to 5; L is an integer of 0 to 5; and q is an integer of 1 to 3,and physiologically acceptable salts thereof are disclosed.The compounds have a high affinity to bone tissues, and the compounds per se and metabolites thereof show significant therapeutic effect on bone diseases such as osteoporosis, rheumatoid arthritis and osteoarthritis.
    Type: Grant
    Filed: December 24, 1992
    Date of Patent: June 27, 1995
    Assignee: Hoechst Japan Limited
    Inventors: Tatsuo Sugioka, Mizuho Inazu
  • Patent number: 5413726
    Abstract: There is disclosed a group of lubricant additives that have improved oxidative stability, high viscosity and relatively lower cost and that comprise telomerized vegetable oils having no more than 4% polyunsaturated fatty acids. There is also disclosed sulfurized and phosphite adduct derivatives of telomerized vegetable oil for use as lubricant additives.
    Type: Grant
    Filed: May 14, 1993
    Date of Patent: May 9, 1995
    Assignee: International Lubricants, Inc.
    Inventor: Phillip S. Landis
  • Patent number: 5407923
    Abstract: Substituted derivatives of deoxymyoinositol of general formula (I): ##STR1## in which R.sup.1, R.sup.2 and R.sup.5 are identical or different and represent a linear or branched alkyl group of 3 to 14 carbon atoms.R.sup.3 and R.sup.4 are identical or different and represent a hydrogen atom, a protecting group of the hydroxyl groups or the residue of formula --CO--(CH.sub.2).sub.n --CH.sub.3in whichn represents the number 12, 13, 14, 15, 16 or 17, and their salts, process for preparing them and their use in medicaments.
    Type: Grant
    Filed: August 12, 1993
    Date of Patent: April 18, 1995
    Assignee: Bayer Pharma
    Inventors: Erwin Bischoff, Zhan Gao, Stefan Wohlfeil, Gabriele Hecker, Jeannine Cleophax, Didier Dubreuil, Stephane Gero, Alice Olesker, Catherine Verre-Sebrie, Mauro V. de Almeida, Georges Vass
  • Patent number: 5395828
    Abstract: A compound of the formula (I) ##STR1## in which R.sub.1 is e.g. phosphate,R.sub.2 is e.g. phosphate or OH, andR.sub.4 is e.g. ##STR2## are suitable Calcium antagonists and useful e.g. for the treatment of cardio-vascular diseases.
    Type: Grant
    Filed: June 24, 1992
    Date of Patent: March 7, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner Schiebler, Elke Deckert, Erik Dreef, Gijs V. D. Marel, Jacques V. Boom
  • Patent number: 5393912
    Abstract: Two types of structural analogues of D-myo-inositol 1,4,5-trisphosphate [Ins(1,4,5)P.sub.4 ] are prepared by a chemo-enzymatic route. These 6-O-substituted analogues retain the biological activity of Ins(1,4,5)P.sub.3 and are able to elicit Ca.sup.2+ release from porcine brain microsomes. Moreover, these analogues allow the preparation of Ins(1,4,5)P.sub.3 -based immunogens and affinity matrix which are successfully applied to the preparation and purification of antibodies against Ins(1,4,5)P.sub.3. These antibodies display discriminative affinity toward Ins(1,4,5)P.sub.3, and provide a useful tool to study intracellular Ca.sup.2+ mobilization.
    Type: Grant
    Filed: January 13, 1994
    Date of Patent: February 28, 1995
    Assignee: The Board of Governors for Higher Education, State of Rhode Island and Providence Plantations
    Inventors: Ching-Shih Chen, Da-Ming Gou, Woan-Ru Shieh
  • Patent number: 5376649
    Abstract: Novel pharmaceutically active bisphosphonic acid derivatives of formula (I), in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently are C.sub.1 -C.sub.22 -alkyl, C.sub.2 -C.sub.22 -alkenyl, C.sub.2 -C.sub.22 -alkynyl, C.sub.3 -C.sub.10 -cycloalkyl, C.sub.3 -C.sub.10 -cycloalkenyl, aryl, aralkyl, silyl and hydrogen, and R.sup.4 is different from hydrogen, Q.sup.1 is hydrogen, fluorine, chlorine, bromine or iodine, and Q.sup.2 is chlorine, bromine or iodine, including the stereoisomers, such as the geometrical isomers and optically active isomers, of the compounds, as well as the pharmaceutically acceptable salts of the compounds.
    Type: Grant
    Filed: February 3, 1992
    Date of Patent: December 27, 1994
    Assignee: Leiras Oy
    Inventors: Esko Pohjala, Keikki Nupponen, Jouko Vepsalainen
  • Patent number: 5338731
    Abstract: Bisphosphonate compounds are of the Formula (I): ##STR1## wherein Y is .dbd.O or .dbd.N--OH and n is from 3 to 24, and further wherein when Y is .dbd.O, (i) R.sub.1 is hydrogen and R.sub.2 is sodium, or (ii) R.sub.1 is sodium and R.sub.2 is methyl, and when Y is .dbd.N--OH, R.sub.1 is sodium and R.sub.2 is methyl.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: August 16, 1994
    Assignee: Yissum, Research Development Company of the Hebrew University of Jerusalem
    Inventors: Eli Breuer, Gershon Golomb
  • Patent number: 5312954
    Abstract: Novel bisphosphonates comprise compounds of the formula (I) ##STR1## wherein m and l are independently 1 or 2; R.sub.1 represents hydrogen, a lower alkyl group, or an alkali metal cation; R.sub.2 represents hydrogen, a lower alkyl group or an alkali metal cation; Y represents .dbd.0 or .dbd.N--OH, or --OH and X represents --(CH.sub.2).sub.n --, a branched alkylene group, or a branched or straight alkenylene or alkynylene chain optionally substituted by one or more oxygen or nitrogen atoms, wherein n is an integer from 3 to 24. Further definitions of X are included in the description.
    Type: Grant
    Filed: May 13, 1992
    Date of Patent: May 17, 1994
    Assignee: Yissum, Research Development Company of the Hebrew University of Jerusalem
    Inventors: Eli Breuer, Gershon Golomb
  • Patent number: 5300671
    Abstract: Diphosphonic acids of formula (I), wherein R.sub.1 and R.sub.2 are hydrogen or C.sub.1 -C.sub.4 alkyl; (A) is hydrogen, halogen, hydroxy or C.sub.1 -C.sub.12 alkyl; (B) is a bond, a C.sub.1 -C.sub.8 alkylene chain, a cycloalkylalkylene chain, an alkylene chain substituted by cyclohexyl or cyclopentyl groups, or an aralkyl chain, an alkyl chain containing an heteroatom (O, S or N--CH.sub.3) or an ureido residue --(CH.sub.2).sub.nl --NHCONH--(CH.sub.2).sub.n --with n ranging from 1 to 5, R.sub.3 is hydrogen, C.sub.1 -C.sub.9 alkyl, C.sub.3 -C.sub.6 cycloalkyl, benzyl, phenyl or p-methoxybenzyl; (C) is C.sub.1 -C.sub.5 alkyl, phenyl or an aralkyl chain; R.sub.4 is hudrogen, C.sub.1 -C.sub.5 alkyl or an amino group optionally substituted by alkyl, phenyl, benzyl, p-methoxybenzyl, acyl, amminoacidic or peptide groups; R.sub.5 and R.sub.6 are 2-haloethyl or together form a 1-aziridinyl residue, are useful as antitumor agent.
    Type: Grant
    Filed: June 9, 1992
    Date of Patent: April 5, 1994
    Assignee: Boehringer Mannheim Italia S.p.A.
    Inventors: Sergio Tognella, Valeria Livi, Ernesto Menta, Silvano Spinelli
  • Patent number: 5292913
    Abstract: Disclosed herein are phosphoric acid esters of myoinositol, which are represented by the following general formula (I): ##STR1## and their salts, as well as a preparation process thereof. The myoinositol derivatives can each be obtained by causing a phosphorylating agent to act on a myoinositol derivative substituted with catalytic reduction removable substituent groups at the positions other than those desired to be substituted by phosphoric acid residual groups and then catalytically reducing the thus-phosphorylated myoinositol.
    Type: Grant
    Filed: September 24, 1992
    Date of Patent: March 8, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Shoichiro Ozaki, Yutaka Watanabe, Akira Awaya, Yusaku Ishizuka
  • Patent number: 5260472
    Abstract: Multigram quantities of Ins(1,4,5) P.sub.3, Ins(1,3,4) P.sub.3, and Ins(1,3,4,5)P.sub.4 are prepared in their enantiomerically pure forms from the two enantiomers of 1,2:5,6-di-O-cyclohexylidene myo-inositol. Also, a facile enzymatic preparation is also described of these chiral precursors through enantiospecific deacylation of the corresponding racemic esters is disclosed.
    Type: Grant
    Filed: January 29, 1992
    Date of Patent: November 9, 1993
    Assignee: The Board of Governors for Higher Education State of Rhode Island and Providence Plantations
    Inventor: Ching-Shih Chen
  • Patent number: 5256808
    Abstract: A method of making a monomer of tetraalkyl vinylidene-1, 1-diphosphonate. The monomer is manufactured by combining an aqueous secondary amine solution with a formaldehyde and a tetra (alkyl) methylene diphosphonate. The resulting mixture is maintained at a pH above about 6 and refluxed for two hours to enable reaction to produce the monomer of tetraalkyl vinylidene-1, 1-diphosphonate. The product monomer is then purified to produce the final end product.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: October 26, 1993
    Assignee: The University of Tennessee Research Corp.
    Inventor: Spiro D. Alexandratos
  • Patent number: 5254544
    Abstract: Hydroxyphosphinyl phosphonate compounds are provided which inhibit the enzyme squalene synthetase and thereby inhibit cholesterol biosynthesis. These compounds have the formula ##STR1## wherein R.sup.2, R.sup.3 and R.sup.4 are independently H, alkyl, metal ion or a prodrug ester; and R.sup.1 is a lipophilic group which contains at least 6 carbons and is alkyl, alkenyl, alkynyl, mixed alkenylalkynyl, a hetero-containing moiety as defined herein, or a phenylalkyl or phenylalkenyl group including those containing a biphenyl group.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: October 19, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Scott A. Biller, John K. Dickson, Jr.
  • Patent number: 5212164
    Abstract: 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 m is 0, 1, 2 or 3; n is 0, 1, 2, 3 or 4;Y.sup.1 and Y.sup.2 are H or halogen;R.sup.2, R.sup.3 and R.sup.4 may be the same or different and are independently H, metal ion, C.sub.1 to C.sub.8 alkyl or C.sub.3 to C.sub.12 alkenyl;X is O, S, NH or NCH.sub.2 R.sup.15 wherein R.sup.15 is H or C.sub.1 to C.sub.5 alkyl; 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;and when m is o, X is other than S; and if m is o and X is 0, then n is 1, 2, 3 or 4; including all stereoisomers thereof.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: May 18, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Scott A. Biller, Michael J. Sofia
  • Patent number: 5210263
    Abstract: The present invention provides novel inositol phosphate analogs and a method for their use for detecting the phosphatidylinositol cycle-dependent calcium of a cell.
    Type: Grant
    Filed: May 15, 1990
    Date of Patent: May 11, 1993
    Assignees: University of Pittsburgh, Mayo Foundation For Medical Education and Research
    Inventors: Alan P. Kozikowski, Garth Powis
  • Patent number: 5210262
    Abstract: 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=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: Grant
    Filed: September 14, 1992
    Date of Patent: May 11, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Janak Singh, Richard H. Mueller
  • Patent number: 5204336
    Abstract: Substituted gem-diphosphonate compounds having use as cholesterol lowering agents are disclosed. A compound of the invention is tetraethyl-2-[3-t-butyl-4-hydroxynaphthyl]ethenylidene-1,1-diphosphonate.
    Type: Grant
    Filed: May 6, 1992
    Date of Patent: April 20, 1993
    Assignee: Symphar S.A.
    Inventors: Lawrence I. Kruse, Virendra P. Shah
  • Patent number: 5196409
    Abstract: Novel bisphosphonates comprise compounds of the formula (I) ##STR1## wherein m and l are independently 1 or 2; R.sub.1 represents hydrogen, a lower alkyl group, or an alkali metal cation; R.sub.2 represents hydrogen, a lower alkyl group or an alkali metal cation; Y represents .dbd.0 or .dbd.N--OH, or --OH; and X represents --(CH.sub.2).sub.n --, a branched alkylene group, or a branched or straight alkenylene or alkynylene chain optionally substituted by one or more oxygen or nitrogen atoms, wherein n is an integer from 3 to 24; with the provision that when l.dbd.m.dbd.1, Y is .dbd.0, and R.sub.1 and R.sub.2 denote a lower alkyl group, n represents an integer from 9 to 20; and with the provision that when l.dbd.m.dbd.2, Y is --OH and R.sub.1 and R.sub.2 are methyl groups, n represents an integer from 9-24; and with the further provision that when l.dbd.m.dbd.2, Y is --OH and R.sub.1 and R.sub.2 are hydrogen, n represents 3, 5 or an integer from 7 to 24; or X is--(CH.sub.2).sub.p --(OCH.sub.2 CH.sub.2).sub.
    Type: Grant
    Filed: September 23, 1991
    Date of Patent: March 23, 1993
    Assignee: Yissum, Research Development Company of the Hebrew University of Jerusalem
    Inventors: Eli Breuer, Gershon Golomb
  • Patent number: 5177239
    Abstract: 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: Grant
    Filed: July 17, 1989
    Date of Patent: January 5, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Janak Singh, Richard H. Mueller
  • Patent number: 5166388
    Abstract: A stabilized composition of phytic acid is obtained by the steps of:heating and drying rice bran de-fatted by pressing;adding acidic water of pH 3 to 5 to the dried rice bran, stirring the solution and completing the stirring before the pH of the solution reaches 5.7; andheating the thus obtained liquid extract to solidify protein components, followed by the removal of the solid matters by filtration. This composition is advantageously used for removing uraroma and body odor.
    Type: Grant
    Filed: July 6, 1990
    Date of Patent: November 24, 1992
    Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.
    Inventors: Kiichi Sawai, Masayasu Kurono, Hiromoto Asai, Takahiko Mitani, Naohisa Ninomiya
  • Patent number: 5157027
    Abstract: 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## and analogs thereof, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are H, lower alkyl, a metal ion or a prodrug ester;R.sup.5 is H, halogen or lower alkyl;Zq is substituted alkenyl, substituted alkynyl, mixed alkenyl-alkynyl or substituted phenylalkyl or, phenylalkenyl or phenylalkynyl, or alkyl, including all stereoisomers thereof.New methods for using such compounds to inhibit cholesterol biosynthesis are also provided.
    Type: Grant
    Filed: May 13, 1991
    Date of Patent: October 20, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Scott A. Biller, David R. Magnin
  • Patent number: 5153183
    Abstract: This invention relates to a methylenediphosphonic acid compound expressed by the formula (1). The compound has a marked effect as an anti-inflammatory agent or, more particularly, against inflammations accompanying disturbances in bone metabolism.
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: October 6, 1992
    Assignee: Toray Industries, Inc.
    Inventors: Norio Kawabe, Keijiro Takanishi, Shu Matsumoto
  • Patent number: 5104863
    Abstract: This invention relates to pyrindine-diphosphonic acid derivatives which are useful in treating or preventing diseases characterized by abnormal calcium and phosphate matabolism, in particular those which are characterized by abnormal bone metabolism. This invention further relates to pharmaceutical compositions which contain the novel compounds of the present invention, and to a method of treating or preventing diseases characterized by abnormal calcium and phosphate metabolism utilizing a compound of the present invention.
    Type: Grant
    Filed: July 3, 1990
    Date of Patent: April 14, 1992
    Assignees: The Procter & Gamble Company, The Procter & Gamble Company
    Inventors: James J. Benedict, Karen Y. Johnson, James J. Benedict, Karen Y. Johnson
  • Patent number: 5103036
    Abstract: A process is provided for preparing a 3-alkenylidene-1,1-bisphosphonate which is an intermediate for preparing an inhibitor of the enzyme squalene synthetase which is useful as an inhibitor of cholesterol biosynthesis, or which bisphosphonate itself is useful as an inhibitor of cholesterol biosynthesis. The process involves the palladium catalyzed coupling of an allylic ester with a tetraester of a methylenebisphosphonate to form a 3-alkenylidene-1,1-bisphosphonate containing an alkene moiety located .gamma., .delta. to the phosphonates.
    Type: Grant
    Filed: May 13, 1991
    Date of Patent: April 7, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: David R. Magnin, Richard B. Sulsky
  • Patent number: 5097057
    Abstract: There are disclosed novel phosphorus-containing compounds including and derived from hydrogen phosphonates. The compounds of the present invention can be prepared by reacting a hydrogen phosphonate with: (a) an ethylene derivative in a Michael reaction, (b) an amine or amide and formaldehyde in a Mannich reaction, (c) an aldehyde or ketone, (d) a halogen, (e) carbon tetrachloride and an alkylamine, and (f) carbon tetrachloride and a hydroxyphosphonate. Halophosphonates produced according to procedure (d) can also be used in reactions with (a) alkylamines and (b) hydroxyphosphonates or epoxides to produce the compounds of the present invention.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: March 17, 1992
    Assignee: Akzo America Inc.
    Inventors: Thomas A. Hardy, Edward N. Walsh
  • Patent number: 5043330
    Abstract: The invention relates to new gem-diphosphonates derivatives substituted by phenol groups of formula (I): ##STR1## as well as the process for their preparation and the pharmaceutical compositions containing them.
    Type: Grant
    Filed: March 14, 1989
    Date of Patent: August 27, 1991
    Assignee: Symphar S.A.
    Inventors: Lan Nguyen, Eric Niesor, Hieu Phan, Pierre Maechler, Craig Bentzen
  • Patent number: 5041429
    Abstract: Phytic acid or at least one of its salts is used as an effective component for cell activators in a hypoxic state, circulatory ameliorators, dementia remedies and edible compositions.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: August 20, 1991
    Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.
    Inventors: Kiichi Sawai, Masayasu Kurono, Hiromoto Asai, Takahiko Mitani, Motohide Hayashi, Tunematu Suzuki, Naohisa Ninomiya
  • Patent number: 4977066
    Abstract: Esters of trihydric or tetrahydric alcohols with alkenylphosphonic or -phosphinic acids, which can be polymerized by means of actinic light, are disclosed. They are combined with polymeric binders, in particular water-soluble polymers, and free-radical-forming photoinitiators to form photopolymerizable mixtures which are suitable for the preparation of photoresists and the production of printing plates. The mixtures show reduced temperature sensitivity and have long shelf lives.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: December 11, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Joachim Gersdorf, Hans-Jerg Kleiner
  • Patent number: 4959441
    Abstract: Alkenylphosphonic and -phosphinic acid esters of 1,1,1-tris(hydroxymethyl)alkanes and of 2,2-bis-hydroxymethyl-1,3-propanediol are useful as cross-linking agents in polymeric hydrogels.
    Type: Grant
    Filed: May 8, 1989
    Date of Patent: September 25, 1990
    Assignee: Cassella Aktiengesellschaft
    Inventors: Friedrich Engelhardt, Ulrich Riegel, Joachim Gersdorf, Hans-Jerg Kleiner
  • Patent number: 4939131
    Abstract: Novel cyclic geminal-diphosphonic acid compounds, and pharmaceutical compositions containing these compounds, which are useful for treating diseases characterized by abnormal calcium and phosphate metabolism; and a method of treating diseases characterized by abnormal calcium and phosphate metabolism utilizing these novel cyclic diphosphonic acid compounds.
    Type: Grant
    Filed: August 14, 1987
    Date of Patent: July 3, 1990
    Assignee: The Procter & Gamble Company
    Inventors: James J. Benedict, Karen Y. Johnson
  • Patent number: 4939284
    Abstract: Disclosed are tetraalkyl enthenylidenebisphosphonates and a method for their manufacture. These compounds are suitable for use as antimicrobial agents in combating a number of pathogenic microorganisms, such as bacteria, yeasts, viruses, fungi and protozoa, when used together with a pharmaceutically-acceptable carrier. Also disclosed is a method for treating infectious diseases by administering a safe and effective amount of these tetraalkyl ethenylidenebisphosphonates.
    Type: Grant
    Filed: January 24, 1989
    Date of Patent: July 3, 1990
    Assignee: The Procter & Gamble Company
    Inventor: Charles R. Degenhardt
  • Patent number: 4886895
    Abstract: There are disclosed multiphosphorus-containing compounds comprising phosphonate-containing or phosphate-containing phosphate esters. The compounds can be prepared by: (a) reacting a phosphonate-containing or phosphate-containing alcohol with phosphorus pentoxide following by reaction with an epoxide, (b) reacting a phosphonate-containing or phosphate-containing alcohol with a phosphorus oxyhalide, hydrolyzing any phosphorus halogen bonds and then reacting the resulting phosphoric acid derivative with an epoxide, (c) transesterifying a phosphonate-containing or phosphate-containing alcohol with a dialkyl phosphite, oxidizing the resulting compound to yield a phosphoric acid derivative and reacting the phosphoric acid derivative with an epoxide. The compounds are useful as flame retardant additives for polyurethanes and textiles.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: December 12, 1989
    Assignee: Akzo America Inc.
    Inventors: Thomas A. Hardy, Edward N. Walsh
  • Patent number: 4883891
    Abstract: There are disclosed novel phosphorous-containing compounds including and derived from hydrogen phosphonates. The compounds of the present invention can be prepared by reacting a hydrogen phosphonate with: (a) an ethylene derivative in a Michael reaction, (b) an amine or amide and formaldehyde in a Mannich reaction, (c) an aldehyde or ketone, (d) a halogen, (e) carbon tetrachloride and an alkylamine, and (f) carbon tetrachloride and a hydroxyphosphate. Halophosphonates produced according to procedure (d) can also be used in reactions with (a) alkylamines and (b) hydroxyphosphonates or epoxides to produce the compounds of the present invention.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: November 28, 1989
    Assignee: Akzo America Inc.
    Inventors: Thomas A. Hardy, Edward N. Walsh
  • Patent number: 4873355
    Abstract: A process for regioselectively preparing phosphorylated cyclitols, in particular phosphorylated inositols such as myo-inositol 1,4,5-tris(phosphate) and myo-inositol 1,3,4,5-tetrakis(phosphate). Novel cyclitols produced by means of this process are also described.
    Type: Grant
    Filed: May 29, 1987
    Date of Patent: October 10, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Frank W. Hobbs, James L. Meek
  • Patent number: 4826629
    Abstract: Multifunctional (antiwear/anitoxidant) additives prepared by reaction of diorganophosphorodithioic acids and a sulfurous-oxyhalide, e.g. thionyl chloride impart resistance to oxidation and abrasion when incorporated into lubricating oils.
    Type: Grant
    Filed: April 20, 1987
    Date of Patent: May 2, 1989
    Assignee: Mobil Oil Corporation
    Inventor: Abraham O. M. Okorodudu
  • Patent number: 4818774
    Abstract: Polyvalent cations (e.g., U(IV), Fe(III) can be extracted from aqueous solution using novel organophosphorus compounds of the formulas: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are selected from alkyl, alkoxyl, alkylaryl and alkylaryloxy groups having from 1 to 18 carbon atoms or hydroxyl;R.sup.3 is independently selected from substituted and unsubstituted alkyl and alkylaryl groups having 1 to about 18 carbon atoms or hydrogen;R.sup.4 is independently selected from alkyl and alkylaryl groups having 1 to about 18 carbon atoms; provided that the sum of the carbon atoms of the R.sup.1, R.sup.2, R.sup.3 and R.sup.4 groups is at least 15; andR.sup.5 is independently selected from substituted and unsubstituted alkyl and alkylaryl groups having 1 to about 18 carbon atoms or a polymeric group; provided that the sum of the carbon atoms of the R.sup.1, R.sup.2 and R.sup.5 groups is at least 16.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: April 4, 1989
    Assignee: Occidental Chemical Corporation
    Inventor: Kenneth M. Kem
  • Patent number: 4732998
    Abstract: The present invention relates to hitherto unknown compounds of the formula I ##STR1## in which R.sub.1 is a straight or branched, saturated or unsaturated aliphatic or alicyclic C.sub.1 -C.sub.10 hydrocarbon radical, an aryl or an aryl-C.sub.1 -C.sub.4 -alkyl radical, R.sub.1 if desired being unsubstituted or substituted with straight or branched C.sub.1 -C.sub.4 -alkyl, amino, C.sub.1 -C.sub.4 -alkamino, di-(C.sub.1 -C.sub.4 -alkyl)-amino, carboxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, hydroxy, C.sub.1 -C.sub.4 -alkoxy, phenoxy, mercapto, C.sub.1 -C.sub.4 -alkylthio, phenylthio, halogen, trifluoromethyl; R.sub.2 stands for hydrogen, C.sub.1 -C.sub.8 -alkyl, aryl-C.sub.1 -C.sub.4 -alkyl or halogen; X is O or S, and n is an integer from 0 to 2; with the proviso that R.sub.2 cannot be hydrogen or methyl if n=O and R.sub.1 is methyl.The compounds of the invention are valuable in the human and veterinary practice.
    Type: Grant
    Filed: March 31, 1986
    Date of Patent: March 22, 1988
    Assignee: Leo Pharmaceutical Products, Ltd.
    Inventor: Ernst T. Binderup
  • Patent number: 4719203
    Abstract: Diphosphonate compounds, processes for their preparation and pharmaceutical compositions containing them and being useful for treating calcium metabolism disorders. The diphosphonates are of the formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen, acyl or alkyl which can be substituted by aryl, R.sub.3 and R.sub.4 are hydrogen or alkyl or R.sub.3 and R.sub.4 together represent lower alkylene, R.sub.5 is a hydrogen atom or alkyl, X is a valency bond or alkylene, Y is a valency bond, alkylene or substituted alkylene, Z is hydrogen, hydroxyl or amino group optionally substituted by alkyl and n is 1, 2 or 3; and including the pharmacologically acceptable salts thereof.
    Type: Grant
    Filed: November 12, 1986
    Date of Patent: January 12, 1988
    Assignee: Boehringer Mannheim GmbH
    Inventors: Elmar Bosies, Rudi Gall
  • Patent number: 4696920
    Abstract: 2-Substituted-1,3-propylidenediphosphonates of formula (I), where A, R.sup.1 and R.sup.2 are defined in claim 1, are therapeutically active compounds, namely for the treatment of cardiovascular diseases.They can be prepared by reacting phosphonating agents with 1,3- dibromopropanes or ditosylates of 1,3-propanediols substituted in position 2. ##STR1## .
    Type: Grant
    Filed: July 16, 1985
    Date of Patent: September 29, 1987
    Assignee: Symphar S.A.
    Inventors: Craig L. Bentzen, Yves Guyon-Gellin, Kyriacos Kalathakis, Hieu T. Phan, Lan Nguyen Mong, Eric Niesor, Jean-Robert Rossier
  • Patent number: 4689123
    Abstract: As novel compounds, ethane tetraphosphonate esters, including octaalkyl and trimethylsilyl esters, and ethylene tetraphosphonic acid, as well as new compositions including a mixture of the acid with tetramethyl methylene diphosphonic acid, and a process for the preparation thereof.
    Type: Grant
    Filed: December 23, 1986
    Date of Patent: August 25, 1987
    Assignee: The Dow Chemical Company
    Inventor: Stephen A. Noding
  • Patent number: 4687768
    Abstract: Novel cyclic geminal-diphosphonic acid compounds, and pharmaceutical compositions containing these compounds, which are useful for treating diseases characterized by abnormal calcium and phosphate metabolism; and a method of treating diseases characterized by abnormal calcium and phosphate metabolism utilizing these noval cyclic diphosphonic acid compounds.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: August 18, 1987
    Assignee: The Procter & Gamble Company
    Inventors: James J. Benedict, Karen Y. Johnson
  • Patent number: 4631142
    Abstract: New diphosphonic acid diesters in which the two phosphorus atoms are bound by a hydrocarbon group while each of the two acid functions of the diphosphonate is esterified by a radical having at least three carbon atoms are prepared by the treatment with a weak base of a corresponding tetramethyl diphosphonate, thereupon replacement of the cations of the base in the resultant disalt, by a radical R by means of a halide of said radical, and finally hydrolysis of the mixed diphosphonate thus obtained. The new compounds are suitable for various known uses of the different diphosphonates and in particular for the complexing of heavy metals; they are used in particular for the extraction of uranium and metals associated with it.
    Type: Grant
    Filed: October 11, 1983
    Date of Patent: December 23, 1986
    Assignee: Societe Nationale Elf Aquitaine (Production)
    Inventor: Georges Sturtz
  • Patent number: 4613674
    Abstract: This invention relates to novel substituted 2-hydroxy-2-phosphinyl ethanals of the general Formula I. ##STR1## to 1,2-dihydroxy-1,2-bisphosphinylethanes of the general Formula II ##STR2## to methods of making the same, to compositions containing compounds of the general Formula I, and/or of the general Formula II, to the use of such compositions to impart flame-resistance to cellulose and cellulose containing materials, to flame-resistant compositions containing compounds of the general Formula II and to the use of the compounds of the general Formula II as metal complexing agents.In the compounds of the Formulas I and II R.sub.1 and R.sub.2 may be the same or different radicals including alkoxy, aryloxy, arylalkoxy, cycloalkoxy, alkyl, alkenyl, aryl, aralkyl, cycloalkyl as well as such radicals containing substituents such as halogen, amino, hydroxy, alkoxy, mercapto, carboxy, carbalkoxy and the like in addition R.sub.1 and/or R.sub.2 may be hydroxy.
    Type: Grant
    Filed: September 23, 1983
    Date of Patent: September 23, 1986
    Inventors: Alexandros K. Tsolis, Ioannis A. Mikroyannidis
  • Patent number: 4587034
    Abstract: Triphosphonic ester, each of the three phosphorus atoms of which is bound to a carbon atom of the same hydrocarbon group, having 2 or 4 free acid functions or two salt functions, is prepared by reacting an alkaline-metal derivative of a phosphite diester with a diphosphonic acid tetra-ester, followed by hydrolysis of the compound obtained. The triphosphonic esters may be used for various known uses of phosphonates, including the extraction of heavy metals.
    Type: Grant
    Filed: October 11, 1983
    Date of Patent: May 6, 1986
    Assignee: Societe Nationale Elf Aquitaine (Production)
    Inventors: Georges Sturtz, Thierry Pensec, Jean-Claude Gautier