Nitrogen Or Sulfur In Phenolic Moiety Patents (Class 560/142)
  • Patent number: 6380181
    Abstract: Catechol derivatives of general formula (I) in which R1 denotes O-acyl and R2 represents amino acid residues in the 3- and/or 4-position function as siderophores and/or as biological chelating agents for iron in gram-negative bacteria. Conjugates with antibiotics improve penetration into bacterial cells, thereby increasing antibacterial efficacy of the cells.
    Type: Grant
    Filed: September 10, 1999
    Date of Patent: April 30, 2002
    Assignee: Gruenenthal GmbH
    Inventors: Lothar Heinisch, Ute Moellmann, Matthias Schnabelrauch, Rolf Reissbrodt
  • Publication number: 20020022738
    Abstract: A solution of N-[o-(p-pivaloyloxybenzenesulfonylamino) benzoyl]glycine monosodium salt tetra-hydrate (I) comprising at least one pH adjuster selected from tri-sodium phosphate, a hydrate thereof, sodium hydroxide or potassium hydroxide and a drug product using the solution. According to the invention, the solubility of the compound (I) increases and thereby it is possible to provide a solution thereof and a drug product using it. Moreover, by using a mixture of water and an organic solvent, greatly improved solubility makes it possible to manufacture a solution of higher concentration of the compound (I), and high-dosage drug products using it.
    Type: Application
    Filed: June 18, 2001
    Publication date: February 21, 2002
    Inventors: Akira Takada, Masao Sudoh
  • Patent number: 6323359
    Abstract: A method is described for the preparation of water-soluble derivatives of probucol compounds having the following formula where R1 and R2 are the same or different and are alkyl, alkenyl or aryl having from 1 to 8 carbon atoms, R3, R4, R5 and R6 are the same or different and are alkyl having from 1 to 4 carbon atoms and X and Y are the same or different and are hydrogen or the groups saturated acyl or unsaturated acyl having from 1 to 8 carbon atoms said saturated or unsaturated acyl groups containing a polar or charged functionality.
    Type: Grant
    Filed: May 2, 2000
    Date of Patent: November 27, 2001
    Assignee: Salsbury Chemicals, Inc.
    Inventor: Paul Alan Jass
  • Patent number: 6310243
    Abstract: The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents, of formula C6R6 wherein three non-adjacent R groups are iodine and the remaining R groups are non-ionic, hydrophilic moieties, said compound being water soluble at 20° C. to a concentration of at least 350 mgl/ml and which in aqueous solution at 20° C. at a concentration of 350 mgl/ml has a viscosity no greater than 13.8 mPas.
    Type: Grant
    Filed: December 22, 1998
    Date of Patent: October 30, 2001
    Assignee: Nycomed Imaging AS
    Inventors: Torsten Almen, Sven Andersson, Lars-Goran Wistrand, Klaes Golman, Oyvind Antonsen, Rune Fossheim, Unni Nordby Wiggen, Hakan Wikstrom, Tomas Klingstedt, Ib Luenbach, Arne Berg, Harald Dugstad
  • Patent number: 6284918
    Abstract: The present invention provides a compound of the formula wherein when X is S; R is selected from the group consisting of CH3, CH2CH3, CH2Ph, (CH2)2Ph, (CH2)2CH3, (CH2)3CH3, (CH2)4CH3, CH2)5CH3, (CH2)6CH3, (CH2)2O(CH2)3CH3, CH2HC═CH(CH2)3CH3, CH2C≡C(CH2)3CH3, CH2C≡C(CH2)2CH3, CH2C≡CCH2CH3, CH2C≡CCH3, CH2C≡CH, CH2C≡C(CH2)4CH3, CH2C≡C(CH2)5CH3, CH2C≡C(CH2)6CH3, (CH2)2C≡C(CH2)2CH3, CH(Ch3)C≡C(CH2)3CH3, (CH2)6I, (CH2)6Br, (CH2)5Br, (CH2)5COOH and (CH2)5OCOCH3, and R′ is selected from the group consisting of CH3, CF3, CH2Cl, CH2Br, CH2CH3, NH2, and OSO2CH3; wherein when R is CH3, R′ can not be CH3 or CH2Cl; wherein when R is CH2CH3, R′ can not be CH3; wherein when X is Se, R is (CH2)6CH3, and R′ is CH3 or a pharmaceutically acceptable salt or hydrate thereof; and wherein when X is O, R is CH2C≡C(CH2)3CH3, and R′ is CH3 or a pharmaceutically acceptable salt or hydrate thereof.
    Type: Grant
    Filed: April 6, 1999
    Date of Patent: September 4, 2001
    Assignee: Vanderbilt University
    Inventors: Lawrence J. Marnett, Amit S. Kalgutkar
  • Patent number: 6162933
    Abstract: A process for the preparation of amido acid phenyl esters of the formula ##STR1## by reaction of a compound of the formula ##STR2## with a compound of the formula ##STR3## in the presence of an acid halide, where A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X and M are as defined in the description, is claimed. The resulting amido acid phenyl esters are used as bleach activators in detergents and cleaners.
    Type: Grant
    Filed: July 30, 1999
    Date of Patent: December 19, 2000
    Assignee: Clariant GmbH
    Inventors: Michael Seebach, Peter Naumann, Werner Janitschek
  • Patent number: 6066757
    Abstract: A stilbene compound is disclosed which has the following general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 each stand for hydrogen, an alkyl group or an acyl group and Ar.sup.1 and Ar.sup.2 each stand for a monovalent homocyclic aromatic group. The stilbene compound may be incorporated into a photoconducting layer of an electrophotographic photoconductor as a charge transporting material. A process for the production of the stilbene compound is also disclosed.
    Type: Grant
    Filed: January 20, 1998
    Date of Patent: May 23, 2000
    Assignee: Ricoh Company, Ltd.
    Inventors: Chiaki Tanaka, Masaomi Sasaki, Tomoyuki Shimada
  • Patent number: 6040338
    Abstract: The present invention relates to a compound of the formula wherein R.sup.1 and R.sup.2 are selected from lower alkyl groups having 1-6 carbon atoms, substituted or unsubstituted aryl groups, and unsaturated alkyl groups having 1-6 carbon atoms; R.sup.3 is a substituted or unsubstituted lower alkyl group having 1-6 carbons; and R.sup.4 is selected from substituted or unsubstituted lower alkyl groups having 1-6 carbon atoms, substituted or unsubstituted aryl groups, and unsaturated alkyl groups having 1-6 carbon atoms. The present invention also relates to a pharmaceutical composition comprising the above compound, as well as a method of treating tumor cells with the compound.
    Type: Grant
    Filed: November 3, 1997
    Date of Patent: March 21, 2000
    Assignee: Yale University
    Inventors: Alan C. Sartorelli, Krishnamurthy Shyam, Philip G. Penketh, Shu-Hui Chen
  • Patent number: 5993780
    Abstract: The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents, of formula I ##STR1## (wherein n is 0 or 1, and where n is 1 each C.sub.6 R.sub.5 moeity may be the same or different; each group R is a hydrogen atom, an iodine atom or a hydrophilic moiety M or M.sub.1, two or three non-adjacent R groups in each C.sub.6 R.sub.5 moiety being iodine and at least one, and preferably two or three, R groups in each C.sub.6 R.sub.5 moiety being M or M.sub.1 moieties; X denotes a bond or a group providing a 1 to 7 atom chain linking two C.sub.6 R.sub.5 moieties or, where n is 0, X denotes a group R; each M independently is a non-ionic hydrophilic moiety; and each M.sub.1 independently represents a C.sub.1-4 alkyl group substituted by at least one hydroxyl group and optionally linked to the phenyl ring via a carbonyl, sulphone or sulphoxide group, at least one R group being an M.sub.1 moiety; with the proviso that where n is zero either at least one M.sub.
    Type: Grant
    Filed: March 24, 1997
    Date of Patent: November 30, 1999
    Assignee: Nycomed Imaging AS
    Inventors: Torsten Almen, Sven Goran Andersson, Lars-Goran Wistrand, Klaes Golman, .O slashed.yvind Antonsen, Rune Fossheim, Unni Nordby Wiggen, H.ang.kan Wikstrom, Tomas Klingstedt, Ib Leunbach, Arne Berg, Harald Dugstad
  • Patent number: 5985859
    Abstract: A method of inhibiting bacterial sialidase comprising administering to a subject an inhibiting effective amount of a compound of formula I: ##STR1## wherein A is CO.sub.2 H, PO.sub.2 H, or SO.sub.2 H; B is N; R.sub.1 and R.sub.2 are H; R.sub.3 and R.sub.4 are, independently, H, OH, NO.sub.2, guanidino, or alkyl or alkenyl of from 1 to 3 carbons where the alkyl or alkenyl is unsubstituted or is substituted, independently, with one or more of OH, NH2, or halide; R.sub.5 is H; and R.sub.6 is COCH.sub.3, or COCI.sub.3 ; or an analog, pharmaceutically acceptable salt, derivative, or mixture thereof. A method of preventing a bacterial or trypanosomal infection using the compounds of formula I. A method of treating a bacterial or trypanosomal infection using the compounds of formula I. A pharmaceutical composition comprising a pharmaceutically acceptable carrier admixed with an inhibiting effective amount of a compound of formula I.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: November 16, 1999
    Assignee: The University of Alabama
    Inventor: Ming Luo
  • Patent number: 5985927
    Abstract: Medicinal products for the selective control of tumor tissue and a method for control of such tumor tissue by administration of such product to a host. The products comprise: (a) two different compounds having a pH below 7 when the compounds are present in a protonated form, such compounds having the formula set forth below and (b) a pharmaceutically acceptable inert medicinal product carrier. The compounds have the following ##STR1## wherein R.sub.1 is hydrogen or a moiety which completes an ester group or an ether group, R.sub.2 is independently selected from the group consisting of an amino group, hydroxyl, an ester group, an ether group and a halogen, and n is an integer of 1 to 4.
    Type: Grant
    Filed: February 17, 1998
    Date of Patent: November 16, 1999
    Inventor: Werner Kreutz
  • Patent number: 5973191
    Abstract: The present invention provides a compound of the formula ##STR1## wherein R is selected from the group consisting of CH.sub.3, CH.sub.2 CH.sub.3, (CH.sub.2).sub.2 CH.sub.3, (CH.sub.2).sub.3 CH.sub.3, (CH.sub.2).sub.4 CH.sub.3, (CH.sub.2).sub.5 CH.sub.3, (CH.sub.2).sub.6 CH.sub.3, (CH.sub.2).sub.2 O(CH.sub.2).sub.3 CH.sub.3, CH.sub.2 HC.dbd.CH(CH.sub.2).sub.3 CH.sub.3, CH.sub.2 C.tbd.C(CH.sub.2).sub.3 CH.sub.3, CH.sub.2 C.tbd.C(CH.sub.2).sub.2 CH.sub.3, CH.sub.2 C.tbd.CCH.sub.2 CH.sub.3, CH.sub.2 C.tbd.CCH.sub.3 and CH.sub.2 C.tbd.CH; and R' is selected from the group consisting of CH.sub.3, CF.sub.3, CH.sub.2 Cl and CH.sub.2 Br or a pharmaceutically acceptable salt or hydrate thereof. Also provided is a method of inhibiting the synthesis of prostaglandin endoperoxide syntase-2 (PGHS-2) in a mammal.
    Type: Grant
    Filed: December 30, 1996
    Date of Patent: October 26, 1999
    Assignee: Vanderbilt University
    Inventors: Lawrence J. Marnett, Amit S. Kalgutkar
  • Patent number: 5882628
    Abstract: The invention provides low viscosity iodinated aryl compounds, useful as X-ray contrast agents, of formula I ##STR1## (wherein n is 0 or 1, and where n is 1 each C.sub.6 R.sub.5 moeity may be the same or different; each group R is a hydrogen atom, an iodine atom or a hydrophilic moiety M or M.sub.1, two or three non-adjacent R groups in each C.sub.6 R.sub.5 moiety being iodine and at least one, and preferably two or three, R groups in each C.sub.6 R.sub.5 moiety being M or M.sub.1 moieties; X denotes a bond or a group providing a 1 to 7 atom chain linking two C.sub.6 R.sub.5 moieties or, where n is 0, X denotes a group R; each M independently is a non-ionic hydrophilic moiety; and each M.sub.1 independently represents a C.sub.1-4 alkyl group substituted by at least one hydroxyl group and optionally linked to the phenyl ring via a carbonyl, sulphone or sulphoxide group, at least one R group being an M.sub.1 moiety; with the proviso that where n is zero either at least one M.sub.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: March 16, 1999
    Assignee: Nycomed Imaging AS
    Inventors: Torsten Almen, Sven Andersson, Lars-Goran Wistrand, Klaes Golman, Oyvind Antonsen, Rune Fossheim, Unni Nordby Wiggen, Hakan Wikstrom, Tomas Klingstedt, Ib Luenbach, Arne Berg, Harald Dugstad
  • Patent number: 5811579
    Abstract: The present invention relates to a method of synthesizing a 2-substituted nitrogen containing compound having a formula (I): ##STR1## by reacting a hydroxylamine of formula (II); ##STR2## or a nitrone of formula (III): ##STR3## with a compound of formula (IV); ##STR4## thereby to form an intermediate compound, and thereafter causing or allowing said intermediate compound to undergo a pericyclic sigmatropic rearrangement reaction to form the compound (I); wherein X is a nucleofugal group, Y is selected from O,S,NH,NR.sub.5 and CR.sub.6 R.sub.7, R.sub.1 is a group which directs the reactivity of compound (II) on to the oxygen atom and R.sub.2 to R.sub.9 are each a substituted or unsubstituted aliphatic, aromatic, heteroaryl or cyclic group or hydrogen which is substantially inert or is protected during the reaction.
    Type: Grant
    Filed: May 7, 1997
    Date of Patent: September 22, 1998
    Assignee: Eastman Kodak Company
    Inventor: John DeMita Goddard
  • Patent number: 5728588
    Abstract: A surface of specific reactivity is formed by adsorbing a modified block polymeric surfactant of the Pluronic-type, i.e., containing pendant poly(ethylene oxide) blocks attached at an end to poly(propylene oxide) center blocks and with specifically reactive groups at the unattached ends of the poly(ethylene oxide) blocks, upon a hydrophobic surface.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: March 17, 1998
    Inventors: Karin Maria Elisabet Caldwell, Per Jan Erik Carlsson, Jenq-Thun Li
  • Patent number: 5723651
    Abstract: An economical process for producing .alpha.-L-aspartyldipeptide amide derivatives useful as sweeteners, by using amino protecting groups which can be removed by hydrolysis under acidic conditions, resulting in conversion of a .beta.-carboxyl acid ester to a carboxylic acid.
    Type: Grant
    Filed: December 28, 1995
    Date of Patent: March 3, 1998
    Assignee: Ajinomoto Co., Inc.
    Inventors: Toyoto Hijiya, Tadashi Takemoto, Ryoichiro Nakamura, Yusuki Amino, Naoko Sugiyama
  • Patent number: 5703073
    Abstract: Nonsteroidal antiinflammatory drugs which have been substituted with a nitrogen monoxide group; compositions comprising (i) a nonsteroidal antiinflammatory drug, which can optionally be substituted with a nitrogen monoxide group and (ii) a compound that directly donates, transfers or releases a nitrogen monoxide group (preferably as a charged species, particularly nitrosonium); and methods of treatment of inflammation, pain, gastrointestinal lesions and/or fever using the compositions are disclosed. The compounds and compositions protect against the gastrointestinal, renal and other toxicities that are otherwise induced by nonsteroidal antiinflammatory drugs.
    Type: Grant
    Filed: October 13, 1995
    Date of Patent: December 30, 1997
    Assignee: NitroMed, Inc.
    Inventors: David S. Garvey, L. Gordon Letts, H. Burt Renfroe, Sang William Tam
  • Patent number: 5681965
    Abstract: Compositions containing as the active ingredient a spin-trapping reagent, preferably .alpha.-phenyl butyl nitrone (PBN) or spin-trapping derivatives thereof, in a suitable pharmaceutical carrier for administration to a patient are disclosed for treating or preventing symptoms associated with aging or other conditions associated with oxidative tissue damage. Other spin-trapping agents can also be used, such as 5,5-dimethyl pyrroline N-oxide (DMPO) or .alpha.-(4-pyridyl 1-oxide)-N-tert-butylnitrone (POBN), and other spin-trapping derivatives thereof. These compositions and methods are useful in the treatment of age-related disorders, pre-surgical and/or pre-anesthetic preparation or administration of chemotherapeutic agents, and in the treatment of disorders or trauma of the brain, cardiovascular system, and lymphatic system.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 28, 1997
    Assignees: Oklahoma Medical Research Foundation, University of Kentucky Research Foundation
    Inventors: John M. Carney, Robert A. Floyd
  • Patent number: 5663308
    Abstract: Organosilicon polymers, including crosslinked polymers and crosslinkable prepolymers, of cyclic polysiloxane, organic dyes, and, optionally, polyenes. The dyes include those with delocalized Pi electron systems linking electron donor groups and electron acceptor groups, and with at least two carbon-carbon double bond-containing pendant groups attached to at least two different sites from among the indicated delocalized Pi electron systems, donor groups, and acceptor groups.
    Type: Grant
    Filed: February 7, 1994
    Date of Patent: September 2, 1997
    Assignee: Hercules Incorporated
    Inventors: Wayne Michael Gibbons, Robert Paul Grasso, Michael Kevin O'Brien, Paul Joseph Shannon, Shao-Tang Sun
  • Patent number: 5599990
    Abstract: A quaternary ammonium halide is prepared by reacting a substituted or unsubstituted haloalkane with a tert-amine in a mol ratio not higher than 1.1/1 in the absence of a solvent and at a temperature such as to maintain the reaction mixture liquid.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: February 4, 1997
    Assignee: Albemarle Corporation
    Inventors: Joseph H. Miller, Joe D. Sauer, Dru L. DeLaet
  • Patent number: 5587509
    Abstract: A method of releasing a caged carboxylic acid in which a 2-alkoxy-5-nitro-phenyl photosensitive group blocks a carboxyl function and the compositions so produced are disclosed.
    Type: Grant
    Filed: March 8, 1995
    Date of Patent: December 24, 1996
    Assignee: Cornell Research Foundation, Inc.
    Inventors: George P. Hess, Barry K. Carpenter, Doraiswamy Ramesh, Raymond Wieboldt
  • Patent number: 5565490
    Abstract: p-Hydroxyaniline derivatives of the formula I ##STR1## where the substituents have the following meanings: R.sup.1 is hydrogen, or unsubstituted or substituted alkyl;R.sup.2 and R.sup.3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy;R.sup.4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl,OR.sup.5 or NR.sup.6 R.sup.7, whereR.sup.5, R.sup.6 are unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, andR.sup.7 is hydrogen or alkyl,and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests, and also compounds of the formula VI ##STR2## and their salts, processes for their preparation, compositions containing them and their use as intermediates and for controlling pests are described.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: October 15, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Oliver Wagner, Karl Eicken, Norbert G otz, Harald Rang, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5565611
    Abstract: The present invention provides a process for preparing an acid addition salt of the Z-isomer of a compound of the formula ##STR1## wherein R.sup.1 and R.sup.2 represent a lower alkyl group, or taken together with the nitrogen atom to which they are attached, form a nitrogen-containing heterocyclic group optionally containing other hetero atom or atoms; R.sup.3 and R.sup.4 represent H, a lower alkyl group, OH, a lower alkoxy group, a lower alkylcarbonyloxy group, an arylcarbonyloxy group optionally substituted with 1-2 substituents selected from lower alkyl, lower alkoxy, halo and CN on the benzene ring, a benzylcarbonyloxy group, a mono- or di(lower alkyl)aminocarbonyloxy group or a mono- or di(aryl)aminocarbonyloxy group; R.sup.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 15, 1996
    Assignee: Taiho Pharmaceutical Co., Ltd.
    Inventors: Shinozaki Fumihiko, Nagasawa Hiroshi, Maruhashi Kazuo
  • Patent number: 5523434
    Abstract: The synthesis of phenol sulfonate esters of alkanoyl amino acids is conducted in the presence of aqueous base to provide bleach activator compounds. Thus, the acid chloride of N-nonanoyl-6-aminocaproic acid is reacted with the sodium salt of p-phenol sulfonate in the presence of water at a pH in the range of about 9 to about 12 to yield the corresponding phenol sulfonate ester. The synthesis of the phenol sulfonate ester of the monononyl amide of adipic acid is also illustrated.
    Type: Grant
    Filed: March 15, 1995
    Date of Patent: June 4, 1996
    Assignee: The Procter & Gamble Company
    Inventors: Michael E. Burns, Anthony J. Simpson
  • Patent number: 5488137
    Abstract: An electrophotographic photoconductor is composed of a substrate and a photoconductive layer formed thereon. The photoconductive layer is composed of a polymer including an acrylic acid ester moiety of formula (I) as repeat unit: ##STR1## wherein R.sup.1 represents hydrogen or a methyl group; R.sup.2, R.sup.3, and R.sup.4 each represent an alkyl group having 1 to 4 carbon atoms, a benzyl group, a phenyl group, a phenoxyl group, chlorine or bromine; n is an integer of 1 to 4; m is 0 or 1; and k is 0 or 1.The polymer and the monomer from which the polymer is prepared are synthesized.
    Type: Grant
    Filed: March 22, 1994
    Date of Patent: January 30, 1996
    Assignee: Ricoh Company, Ltd.
    Inventors: Hiroshi Tamura, Toshio Fukagai, Naoshi Mishima, Masaomi Sasaki
  • Patent number: 5484935
    Abstract: Pharmaceutical compounds of the formula ##STR1## in which R.sup.1 and R.sup.3 are each C.sub.1-4 alkyl or C.sub.1-4 alkyl-carbonyl, and R.sup.2 is carboxy, tetrazolyl, C.sub.1-4 alkyl-sulphonamido or --CR.sup.4 R.sup.5 CO.sub.2 H where R.sup.4 and R.sup.5 are each hydrogen or C.sub.1-4 alkyl; provided that when R.sup.1 and R.sup.3 are both methyl and when R.sup.1 and R.sup.3 are both methylcarbonyl, R.sup.2 is not carboxy; and salts and esters thereof.
    Type: Grant
    Filed: August 11, 1994
    Date of Patent: January 16, 1996
    Assignee: Lilly Industries Limited
    Inventors: Peter T. Gallagher, Terence A. Hicks, William M. Owton
  • Patent number: 5468474
    Abstract: The present invention relates to N-acylglutamine derivatives of formula (I): ##STR1## The N-acylglutamine derivatives are well compatible with oily bases and have good skin-moisturizing activity and hair growth-stimulative effect. These are useful as cosmetics and hair growth stimulants.
    Type: Grant
    Filed: July 27, 1994
    Date of Patent: November 21, 1995
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Shinkichi Honda, Kenji Torii, Yoichiro Arai, Masaji Kasai, Hiromasa Kato, Takao Iida, Tomoya Takahashi, Yoshiharu Yokoo, Toshikazu Kamiya, Tatsuya Tamaoki
  • Patent number: 5466840
    Abstract: This invention relates to a 5 step process for preparing a purified alkali metal salt of 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate in one reaction vessel without isolation of intermediates. The steps are as follows: A) reacting an alkali metal salt of 4-hydroxybenzenesulfonic acid with a C.sub.2 to C.sub.4 carboxylic anhydride in a solvent to form an alkali metal salt of 4-acyloxybenzenesulfonic acid and a C.sub.2 to C.sub.4 carboxylic acid. B) adding an [(1-oxyalkanoyl)amino]alkanoic acid and a transesterification catalyst to the reaction product of step A) and heating at a temperature and pressure sufficient to maintain reflux of the solvent and to remove the C.sub.2 to C.sub.4 carboxylic acid from the reaction vessel to form a reaction mixture containing an alkali metal salt of 4-sulfophenyl-[(1-oxyalkanoyl)amino]alkanoate. C) removing the solvent from the reaction mixture formed in step B).
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: November 14, 1995
    Assignee: Eastman Chemical Company
    Inventors: Gary P. Lutz, George C. Zima, Rex Bernard
  • Patent number: 5463108
    Abstract: The present invention provides a unique and novel way of producing 4-acetoxystyrene. In this new process, 4-hydroxystyrene is acetylated, in the presence of an acetylation agent, under suitable conditions of temperature and pressure and for a sufficient period of time to form acetoxystyrene.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: October 31, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, William W. Wilkison, III, Keith M. Russ, Lynn Massarelli
  • Patent number: 5453533
    Abstract: An influenza virus neuraminidase inhibitor, its analogs, its pharmaceutically acceptable salts, derivatives, and mixtures thereof having the following formula: ##STR1## where A is CO.sub.2 H, CO.sub.2 H.sub.3, NO.sub.2, SO.sub.3 H or PO.sub.3 H.sub.2, B is CH, N, O or S, R.sub.1 and R.sub.2 are H, NO.sub.2 or (CH.sub.m).sub.n X.sub.1 where m=1 or 2, n is an integer from 0 to 4 and X.sub.1 is guanidino, OH, NH.sub.2, SH, NO.sub.2, F, Cl, Br, I, CN, CF.sub.3, CO.sub.2 H, SO.sub.3 H or PO.sub.3 H.sub.2, R.sub.3 and R.sub.4 are H, (CH.sub.o).sub.p X.sub.2, (CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2, NH(CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2, NHCO(CH.sub.o).sub.p CH.sub.2 X.sub.2 or NHCO(CH.sub.o).sub.p CHX.sub.2 CH.sub.2 X.sub.2 where o=1 or 2, p is an integer from 0 to 4 and X.sub.2 is H, guanidino, OH, NH.sub.2, SH, NO.sub.2, CF.sub.3, CO.sub.2 H, SO.sub.3 H or PO.sub.3 H.sub.2 , R.sub.5 =H, OH, NH.sub.2, (CH.sub.k).sub.1 X.sub.3, CO(CH.sub.k).sub.1 X.sub.3, SO(CH.sub.k).sub.1 X.sub.3 or SO.sub.2 (CH.sub.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: September 26, 1995
    Assignee: The University of Alabama at Birmingham
    Inventors: Ming Luo, Wayne J. Brouillette, Gillian Air
  • Patent number: 5391812
    Abstract: Polyglycolate compounds are provided having the general structure: ##STR1## wherein n is an integer from 2 to about 10; R is C.sub.1-20 linear or branched alkyl, alkoxylated alkyl, cycloalkyl, aryl, alkylaryl, substituted aryl; R' and R" are independently H, C.sub.1-20 alkyl, aryl, C.sub.1-20 alkylaryl, substituted aryl, and NR.sub.3.sup..alpha.+, wherein R.sup..alpha. is C.sub.1-30 alkyl; and L is a leaving group displaceable in a peroxygen bleaching solution by perhydroxide anion. When this compound is combined with a source of peroxygen in aqueous solution, then a plurality of stain removing peracids are formed. Such peracids are formed substantially sequentially beginning with the carbonyl adjacent to the leaving group L. Thus, a first stain removing peracid having the structure ##STR2## will be formed in amounts approaching quantitative yield.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: February 21, 1995
    Assignee: The Clorox Company
    Inventors: Richard R. Rowland, Ronald A. Fong, Richard J. Wiersema, Alfred G. Zielske
  • Patent number: 5385942
    Abstract: A quinone derivative useful in the treatment of hepatic diseases defined by the general formula: ##STR1## where X and Y may be the same or different from each other and are each a hydroxyl group, a group represented by the formula --(--OCH.sub.2 --).sub.n --OR.sup.6, wherein n is 0 or 1 and R.sup.6 is a lower alkyl group, or an acyl group.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: January 31, 1995
    Assignee: Eisai Co., Ltd.
    Inventors: Shinya Abe, Yasushi Okamoto, Katsuya Tagami, Shigeki Hibi, Junichi Nagakawa, Kazuo Hirota, Ieharu Hishinuma, Kaname Miyamoto, Takashi Yamanaka, Hiromitsu Yokohama, Tsutomu Yoshimura, Tohru Horie, Yasunori Akita, Koichi Katayama, Isao Yamatsu
  • Patent number: 5384425
    Abstract: Diurea derivatives are provided which can be represented by the following general formula and salts thereof: ##STR1## wherein, R.sup.1 and R.sup.2 are the same or different, and each represents C.sup.1 -10 alkyl group, a C.sup.3 -18 cycloalkyl group, or a lower alkyl group substituted by cycloalkyl radical(s);R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different, and each represents a hydrogen atom, a lower alkyl group, a cycloalkyl group, hydrocarbyl aralkyl group, a pyridyl group, or an unsubstituted or substituted phenyl group, the substituents of the phenyl group being selected from a group consisting of lower alkyl radical, halogen atom-substituted lower alkyl radical, halogen atom, nitro radical, amino radical, mono- or di-lower alkylamino radical, lower acylamino radical, hydroxyl radical, lower alkoxy radical and lower acyloxy radical;X represents an oxygen atom or a sulfur atom, and n.sup.1 and n.sup.2 represent an integer of 1 to 6; and wherein at least one of R.sup.3 -R.sup.
    Type: Grant
    Filed: October 7, 1993
    Date of Patent: January 24, 1995
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Noriki Ito, Tomoyuki Yasunaga, Yuichi Iizumi, Tomio Araki
  • Patent number: 5338886
    Abstract: Disclosed is a process for preparation of an aromatic thiol corresponding to the structureA-(SH)nwhereinA is a substituted or unsubstituted aromatic radical and n is 1, 2, 3, 4, 5 or 6 comprising contacting at a temperature of at least 80.degree. C. an aromatic halide corresponding to the structureA-XmwhereinA is the same as above, X is bromine oriodine and n is 1, 2, 3, 4, 5, or 6with thiourea in the presence of nickel metal.
    Type: Grant
    Filed: May 17, 1993
    Date of Patent: August 16, 1994
    Assignee: Eastman Chemical Company
    Inventors: Mark Rule, James T. Tanner, III
  • Patent number: 5306837
    Abstract: Novel intermediates useful in the preparation of the optically active antiviral compound [1R-(1.alpha.,2.beta.,3.alpha.)]-2-amino-9-[2,3-bis(hydroxymethyl)cyclobut yl]-1,9-dihydro-6H-purin-6-one are described.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: April 26, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Gregory S. Bisacchi, Toomas Mitt
  • Patent number: 5290793
    Abstract: Dihydrocaffeic acid derivatives are here disclosed which are applicable as medicines having excellent absorbency in the case of oral administration and good concentration retention in blood.The disclosed compounds have the function to induce the production and secretion of a nerve growth factor (NGF) in the brain tissue, and therefore they are effective as medicines for the progression inhibition and therapy of regressive disorders of the central nervous system.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: March 1, 1994
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Nobuyuki Fukazawa, Hajime Iizuka, Osamu Yano, Yukio Miyama
  • Patent number: 5283352
    Abstract: Catechol compounds of formula I ##STR1## where R.sub.1, R.sub.2, R.sub.3 and X are as described herein are effective Catechol-O-methyltransferase inhibitors.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: February 1, 1994
    Assignee: Orion-yhtyma Oy
    Inventors: Reijo J. Backstrom, Kalevi E. Heinola, Erkki J. Honkanen, Seppo K. Kaakkola, Pekka J. Kairisalo, Inge-Britt Y. Linden, Pekka I. Mannisto, Erkki A. O. Nissinen, Pentti Pohto, Aino K. Pippuri, Jarmo J. Pystynen
  • Patent number: 5258406
    Abstract: This invention provides certain sulfonimidamide compounds, formulations and method of use of these compounds in treating susceptible neoplasms.
    Type: Grant
    Filed: December 16, 1992
    Date of Patent: November 2, 1993
    Assignee: Eli Lilly and Company
    Inventors: John E. Toth, James E. Ray
  • Patent number: 5234946
    Abstract: The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7,X and Y are linking groups,R.sup.2 is H or lower alkyl,R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl,R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms,R.sup.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: August 10, 1993
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Takezawa, Masahiro Hayashi, Yoshikazu Iwasawa, Masaaki Hosoi, Yoshiaki Iida, Yoshimi Tsuchiya, Masahiro Horie, Toshio Kamei
  • Patent number: 5220051
    Abstract: The polycationic compound having the formula (I) is useful for an organic peracid precursor. A bleach composition comprises the polycationic compound and a peroxide. ##STR1## in which X is a cation, Y is an alkylene, Z is a specific group containing carbonyl group and A is an anionic group.
    Type: Grant
    Filed: October 29, 1990
    Date of Patent: June 15, 1993
    Assignee: KAO Corporation
    Inventors: Kohshiro Sotoya, Nobuyuki Ogura, Hiroyuki Imoto
  • Patent number: 5214194
    Abstract: A process for the preparation of 5-substituted 2-aminophenols via nitrones, comprises two reactions. First, a nitrone is reacted with a trihaloacetyl halide to regiospecifically convert the nitrone to a 5-substituted-2-aminophenol derivative (I). Subsequently, the derivative is hydrolyzed to form the 5-substituted-2-aminophenol. The product is useful as a chemical intermediate, e.g. for the preparation of couplers used in photographic chemistry.
    Type: Grant
    Filed: September 24, 1991
    Date of Patent: May 25, 1993
    Assignee: Eastman Kodak Company
    Inventors: Ping-Wah Tang, Jeffrey R. Neff, Frank T. Melia, Donald J. Schuster
  • Patent number: 5214192
    Abstract: Diacetoxyatene compounds are obtained by reacting a perborate such as sodium perborate monohydrate or tetrahydrate and acetic acid with an iodoarene compound under mild conditions, such as 40 to 50.degree. C. The iodoarene can be further substituted by a wide range of substituents, such as halo, nitro, alkyl, alkoxy or carbosylic acid, in any position around the nucleus, except that electron withdrawing substituents occupy meta positions only. The invention process thus enables a wide range of substituted diacetoxyarene compounds to be produced using widely available and easily handled materials under mild operating conditions.
    Type: Grant
    Filed: October 2, 1991
    Date of Patent: May 25, 1993
    Assignee: Interox Chemicals Limited
    Inventors: Alexander McKillop, Duncan Kemp
  • Patent number: 5202483
    Abstract: Ethylenically unsaturated compounds of the general formula I ##STR1## where R.sub.1 is alkyl of 1 to 4 carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, phenyl or phenyl in which some or all of the hydrogen atoms have been replaced by radicals R.sup.4, not more than two substituents R.sup.4 being identical, or R.sup.1 together with R.sup.2 or together with R.sup.6 forms a --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 -- bridge,R.sup.4 is alkyl of 1 to 24 carbon atoms, --OH, --O--R.sup.7, --S--R.sup.7, ##STR2## R.sup.2 or R.sup.6, independently of one another, both are hydrogen, or one of the radicals R.sup.4, or, where R.sup.1 is aryl,R.sup.2 or R.sup.6 is a direct bond to R.sup.1 in the ortho-position with respect to the carbonyl group, andR.sup.3 and R.sup.5 are each hydrogen, one of the radicals R.sup.4 or a group the general formula II ##STR3## where R.sup.7 and R.sup.8 are each alkyl of 1 to 4 carbon atoms,R.sup.9 is cycloalkyl of 5 or 6 carbon atoms,R.sup.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: April 13, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Rehmer, Kaspar Bott
  • Patent number: 5192799
    Abstract: 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: Grant
    Filed: June 5, 1992
    Date of Patent: March 9, 1993
    Assignee: 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
  • Patent number: 5177252
    Abstract: Esters having the general formula ##STR1## where X is a halogen, the sum of the atomic masses of the halogen atoms on the phenyl ring is at least 90, n is 1-5, Y is an alkyl, ether, ester, aldehyde, ketone, acetal, ketal, cyano, or nitro substituent, m is 0-2, Z is an ester linkage --OCO-- or --CO.sub.2 --, R' is a haloalkyl group containing at least one F atom and containing halogen atoms in place of greater than 60% of the hydrogen atoms of the corresponding unhalogenated alkyl group, with the sum of the atomic masses of the halogen atoms on said R' group being greater than 135 and the compound as a whole containing at least two types of halogen atoms, and p is 1-3, constitute high density flotation fluids and lubricants for inertial instruments such as gyroscopes and accelerometers, and for electrical contacts. Synthetic methods are disclosed for production of such fluids from available starting materials.
    Type: Grant
    Filed: April 11, 1990
    Date of Patent: January 5, 1993
    Assignee: The Charles Stark Draper Laboratory, Inc.
    Inventor: John R. Williams
  • Patent number: 5166218
    Abstract: Tertiary and secondary amines of the formulas ##STR1## and ##STR2## wherein n is the integer 1 or 2,R is hydrogen, lower-alkanoyl or phenyl-lower-alkanoyl,X.sup.1 is phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position,X.sup.2 is lower-alkyl, phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position or phenyl optionally monosubstituted by fluorine, chlorine, trifluoromethyl or lower-alkoxy,Y is hydrogen or methyl, andZ is a phenyl or thienyl residue substituted as hereinafter described,and the physiologically and pharmaceutically compatible salts are described. The compounds of formulas I and V-1 have catabolic activity and can be used for the treatment of obesity and diabetes mellitus or for the treatment of conditions which are associated with an increased protein breakdown, or as feed additives for fattening animals. The compounds of formulas I and V-1 can be prepared starting from corresponding primary amines.
    Type: Grant
    Filed: August 12, 1991
    Date of Patent: November 24, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Leo Alig, Marcel Muller
  • Patent number: 5153357
    Abstract: A process for the preparation of 2-(hydrogen, halogen or lower alkyl)-3-(hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, --OCH.sub.2 CH.sub.2 OCH.sub.3, --OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, --OCH.sub.2 CH.sub.2 SCH.sub.3 or --OCH.sub.2 CH.sub.2 SC.sub.2 H.sub.5)-4-(alkylthio or alkylsulfonyl)-acetophenones.
    Type: Grant
    Filed: December 17, 1991
    Date of Patent: October 6, 1992
    Assignee: Imperical Chemical Industries PLC
    Inventor: Richard W. Brown
  • Patent number: 5145997
    Abstract: Poly (alkylene oxide) substituted acetoacetanilides of the formula: ##STR1## wherein B comprises a divalent bridging moiety selected from the group consisting of C.sub.1 -C.sub.6 alkylene, --NHSO.sub.2 --, --O--, --CO--, --COO--, and --NCHO--; X comprises a poly (alkylene oxide) having a number average molecular weight of about 200 to 10,000; R comprises 0 to 4 moieties independently selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and halogen; and d is an integer of 1 to 3. The poly (alkylene oxide) substituted acetoacetanilides are prepared by reacting a poly (alkylene oxide) monoamine, diamine or triamine with isatoic anhydride followed by acetoacetylation of the resultant aminobenzamide. The substituted acetoacetanilides are useful for preparing improved diarylide pigment compositions which in turn are useful for preparing storage stable printing inks (especially of the publication gravure type).
    Type: Grant
    Filed: February 12, 1991
    Date of Patent: September 8, 1992
    Assignee: Sun Chemical Corporation
    Inventors: Russell J. Schwartz, Anthony C. Zwirgzdas, Terence R. Chamberlain
  • Patent number: 5144059
    Abstract: The compound of the formula ##STR1## (wherein R, R.sub.1 and R.sub.2 have the meanings given in the description), salts thereof with pharmaceutically acceptable organic or inorganic acids, process and intermediates for the preparation thereof and a pharmaceutical composition containing said compound are described.The compounds of formula I and the salts thereof are useful in the treatment of heart and renal diseases.
    Type: Grant
    Filed: April 20, 1990
    Date of Patent: September 1, 1992
    Assignee: Simes Societa Italiana Medicinali E. Sintetici S.A.
    Inventors: Cesare Casagrande, Francesco Santangelo
  • Patent number: 5142095
    Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migraines, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.
    Type: Grant
    Filed: August 17, 1989
    Date of Patent: August 25, 1992
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Daniel L. Flynn