Isonitriles (i.e., Compounds Having An Isonitrile Group, Usually Represented As -n=c, Bonded Directly To Carbon, Which Carbon May Be Single Bonded To Any Atom But May Be Multiple Bonded Only To Carbon) Patents (Class 558/302)
  • Patent number: 5210270
    Abstract: A new method for synthesizing 2-alkoxyisobutylisonitrile is provided in which isobutylene is used as the starting material. The haloalkoxylation of isobutylene in alcohol medium gives 2-alkoxyisobutylhalide which is then converted to 2-alkoxyisobutylamine. In the basic condition, the reaction of 2-alkoxyisobutylamine with chloroform produces 2-alkoxyisobutylisonitrile. The synthesis process contains three steps by which a higher yield is achieved. 2-Alkoxyisobutylisonitrile is labelled with technetium-99m by exchange labelling of stable tetrakis(2-alkoxyisobutylisonitrile)copper(I) complex. Tetrakis(2-alkoxyisobutylisonitrile)copper(I) complex can be prepared by the exchange of acetonitrile molecules in tetrakis(acetonitrile)copper(I) complex with isonitrile ligands.
    Type: Grant
    Filed: November 25, 1991
    Date of Patent: May 11, 1993
    Assignee: Institute of Nuclear Energy Research
    Inventors: Lee Te-Wei, Ting Gann, Su Chang-Shinn, Chyi Shyh-Yi
  • Patent number: 5107021
    Abstract: The invention relates to polyfluoroalkyl nitrogen compounds of general formula:R.sub.F --(CH.sub.2).sub.2 --Xin which X denotes an isothiocynate --N.dbd.C.dbd.S, carbodiimide --N.dbd.C.dbd.N(CH.sub.2).sub.2 --R'.sub.F or thiourea --NH--CS--A group, A denoting an optionally substituted amino group, and each of the symbols R.sub.F and R'.sub.F denotes a perfluoroalkyl radical.These compounds, prepared from the corresponding azides R.sub.F (CH.sub.2).sub.2 N.sub.3 or amines R.sub.F (CH.sub.2).sub.2 NH.sub.2, can be used as surface-active agents or precursors of such agents.
    Type: Grant
    Filed: April 12, 1991
    Date of Patent: April 21, 1992
    Assignee: Societe ATOCHEM
    Inventors: Eric Bollens, Francois Szonyi, Aime Cambon
  • Patent number: 5091553
    Abstract: Process for the preparation of asymmetrically substituted ureas, carbamates, thiocarbamates or substituted isocyanates by reaction of an adduct of isocyanic acid and a tertiary amine with a primary and secondary amine, an alcohol, a thiol or a compound having one or two non-cumulated olefinic double bonds.
    Type: Grant
    Filed: July 12, 1990
    Date of Patent: February 25, 1992
    Assignee: Chemie Linz Gesellschaft m.b.H.
    Inventors: Martin Mullner, Gerhard Stern, Erich Schulz, Markus Rossler
  • Patent number: 5026910
    Abstract: The invention relates to polyfluoroaklyl nitrogen compounds of general formula:R.sub.F --(CH.sub.2).sub.2 --Xin which X denotes an isothiocyanate --N.dbd.C.dbd.S, carbodiimide --N.dbd.C.dbd.N(CH.sub.2).sub.2 --R'.sub.F or thiourea --NH--CS--A group, A denoting an optionally substituted amino group, and each of the symbols R.sub.F and R'.sub.F denotes a perfluoroalkyl radical.these compounds, prepared from the corresponding axides R.sub.F (CH.sub.2).sub.2 N.sub.3 or amines R.sub.F(CH.sub.2).sub.2 NH.sub.2, can be used as surface-active agents or precursors of such agents.
    Type: Grant
    Filed: May 22, 1990
    Date of Patent: June 25, 1991
    Assignee: Societe Atochem
    Inventors: Eric Bollens, Francois Szonyi, Aime Cambon
  • Patent number: 5008418
    Abstract: Tris(isonitrile)copper(I) complex salts with anions selected from BF.sub.4, PF.sub.6, ClO.sub.4, I, Br, Cl and CF.sub.3 COO are useful in preparing radionuclide complexes rapidly at room temperature. Preferred isonitrile ligands are ether isonitriles. The tris(isonitrile)copper(I) adducts enable technetium complexes, such as those of Tc99m, to be prepared easily just prior to their use as imaging agents.
    Type: Grant
    Filed: August 23, 1989
    Date of Patent: April 16, 1991
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Tahir Iqbal, John H. Cain, Jr., Jack J. Slosky
  • Patent number: 4990633
    Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
  • Patent number: 4988827
    Abstract: Ether-substituted isonitriles, Tc99m complexes thereof, and processes for myocardial tissue radioimaging using the Tc99m complexes.
    Type: Grant
    Filed: June 1, 1987
    Date of Patent: January 29, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Paul L. Bergstein, Vinayakam Subramanyam
  • Patent number: 4922016
    Abstract: N-(sulfonylmethyl)formamides are obtained by reacting a sulfinic acid, formaldehyde and formamide in the presence of a second acid and a controlled amount of water. The formamides can be converted to the corresponding sulfonylmethylisocyanides.
    Type: Grant
    Filed: July 26, 1989
    Date of Patent: May 1, 1990
    Assignee: Gist-Brocades N.V.
    Inventor: Nicolaas C. M. E. Barendse
  • Patent number: 4898964
    Abstract: An additive for synthetic resins includes a [liquid rubber]/[polyester] block copolymer comprising block liquid rubber compound parts and block polyester parts as constituent segments. One or more of these polyester blocks are connected to each one of the polydiene block parts through ester bond.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: February 6, 1990
    Assignee: Takemoto Yushi Kabushiki Kaisha
    Inventors: Mitsuo Kinoshita, Shigeru Imamura, Hirokazu Matsueda
  • Patent number: 4898965
    Abstract: An additive for synthetic resins contains a block copolymer having as its constituent segments both polyester block obtainable by ring-opening polymerization of .epsilon.-aliphatic lactone and polydiene block. One or more of these polyester blocks are connected to the polydiene block through ester bond and at least one of these polyester blocks has at its end a reactive group such as vinyl group, epoxy group, isocyanate group or carboxyl group.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: February 6, 1990
    Assignee: Takemoto Yushi Kabushiki Kaisha
    Inventors: Mitsuo Kinoshita, Shigeru Imamura, Hirokazu Matsueda
  • Patent number: 4885100
    Abstract: Tris(isonitrile)copper(I) complex salts with anions selected from BF.sub.4, PF.sub.6, ClO.sub.4, I, Br, Cl and CF.sub.3 COO are useful in preparing radionuclide complexes rapidly at room temperature. Preferred isonitrile ligands are ether isonitriles. The tris(isonitrile)copper(I) adducts enable technetium complexes, such as those of Tc99m, to be prepared easily just prior to their use as imaging agents.
    Type: Grant
    Filed: September 11, 1987
    Date of Patent: December 5, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Tahir Iqbal, John H. Cain, Jr., Jack J. Slosky
  • Patent number: 4872561
    Abstract: A coordination complex comprising a radionuclide selected from the class consisting of radioactive isotopes of Tc, Ru, Co, Pt and Re and an isonitrile ligand of the formula:(CNX)R,where X is a lower alkyl group having 1 to 4 carbon atoms, wherein R is selected from the group consisting of COOR.sup.1 and CONR.sup.2 R.sup.3 where R.sup.1 can be H, a pharmaceutically acceptable cation, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms. R.sup.2, and R.sup.3 can be H, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and R.sup.2 and R.sup.3 can be the same of different is disclosed. Kits that can be used to form these complexes are also disclosed.
    Type: Grant
    Filed: December 29, 1987
    Date of Patent: October 10, 1989
    Assignees: Massachusetts Institute of Technology, President and Fellows of Harvard College
    Inventors: Alun G. Jones, Alan Davison, James Kronauge, Michael J. Abrams
  • Patent number: 4868323
    Abstract: Phenyl isonitriles are prepared by reaction of substantially equimolar amounts on N-arylformimidates and a lithium dialkylamide.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: September 19, 1989
    Assignee: Mine Safety Appliances Company
    Inventor: Lin-Chen Yu
  • Patent number: 4864051
    Abstract: A new process for preparing 2-methoxyisobutylisonitrile is described. 2-methoxyisobutylisonitrile is used in the preparation of Tc-99m hexakis (2-methoxyisobutylisonitrile). This cationic complex is useful as a myocardial perfusion agent.
    Type: Grant
    Filed: September 2, 1988
    Date of Patent: September 5, 1989
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Kondareddiar Ramalingham
  • Patent number: 4834909
    Abstract: Compositions of matter and methods of preparation are described for water and air stable, square planar transition metal double-complex salts which contain isonitrile ligands derivatized with long chain aliphatic groups. These salts are composed of two metal-containing complex ions: the cation is a tetrakis isonitrile metal ion and the anion is a tetrahalometallate or tetracyanometallate. These double-complex salts exhibit the novel property of thermochromism and are useful as temperature indicators and in imaging applications.
    Type: Grant
    Filed: January 30, 1987
    Date of Patent: May 30, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Colleen C. Nagel
  • Patent number: 4735793
    Abstract: A coordination complex comprising a radionuclide selected from the class consisting of radioactive isotopes of Tc, Ru, Co, Pt and Re and an isonitrile ligand of the formula:(CNX)R,where X is a lower alkyl group having 1 to 4 carbon atoms, wherein R is selected from the group consisting of COOR.sup.1 and CONR.sup.2 R.sup.3 where R.sup.1 can be H, a pharmaceutically acceptable cation, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, R.sup.2, and R.sup.3 can be H, or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and R.sup.2 and R.sup.3 can be the same or different is disclosed. Kits that can be used to form these complexes are also disclosed.
    Type: Grant
    Filed: August 30, 1985
    Date of Patent: April 5, 1988
    Assignees: Massachusetts Institute of Technology, President and Fellows of Harvard College
    Inventors: Alun G. Jones, Alan Davison, James Kronauge, Michael J. Abrams
  • Patent number: 4707544
    Abstract: A method for preparing a coordination complex of an isonitrile ligand and radionuclide such as Tc, Ru, Co, Pt, Fe, Os, Ir, W, Re, Cr, Mo, Mn, Ni, Rh, Pd, Nb and Ta is disclosed. The method comprises preparing a soluble metal adduct of said isonitrile ligand by admixing said ligand with a salt of a displaceable metal having a complete d-electron shell selected from the group consisting of Zn, Ga, Cd, In, Sn, Hg, Tl, Pb and Bi to form a soluble metal-isonitrile salt, and admixing said metal isonitrile salt with a salt comprising said radioactive metal in a suitable solvent to displace said displaceable metal with the radioactive metal thereby forming said coordination. The complex is useful as a diagnostic agent for labelling liposomes or vesicles, and selected living cells containing lipid membranes, such as blood clots, myocardial tissue, gall bladder tissue, etc.
    Type: Grant
    Filed: November 28, 1984
    Date of Patent: November 17, 1987
    Assignees: President and Fellows of Harvard College, Massachusetts Institute of Technology
    Inventors: Alun G. Jones, Alan Davison, Michael J. Abrams
  • Patent number: 4704449
    Abstract: A poly(vinyliminomethylene) polymer having at least one recurring structural unit of the formula: ##STR1## wherein R and R', which are the same or different, are each hydrogen, a C.sub.1 -C.sub.8 alkyl group or C.sub.3 -C.sub.7 cycloalkyl group which alkyl or cycloalkyl groups are unsubstituted or substituted by lower alkyl or alkoxy groups or which contain up to four non-catenated oxygen atoms, a C.sub.2 -C.sub.8 alkenyl group or a C.sub.5 -C.sub.7 cycloalkenyl group which is unsubstituted or substituted by lower alkyl or alkoxy groups, a phenyl group or naphthyl group which is unsubstituted or substituted by lower alkyl or alkoxy groups, with the proviso that at least one of R and R' be a substituent other than hydrogen; R" is hydrogen; and n has a value such that the weight-average molecular weight is in the range of about 2,000 to 400,000 as determined by gel permeation chromatography.
    Type: Grant
    Filed: September 30, 1985
    Date of Patent: November 3, 1987
    Inventors: Robert B. King, Lester Borodinsky