Acyclic Patents (Class 562/512)
  • Patent number: 5095138
    Abstract: The invention relates to production of esters of mercaptocarboxylic acids and alcohols forming an azeotrope with water.The esterification is carried out continuously in the presence of an excess of alcohol and the water formed is removed by entraining azeotropically under vacuum at a temperature such that the residual water concentration in the reaction mixture remains constantly below 0.5% by weight.The process according to the invention applies more particularly to the synthesis of octyl esters of thioglycolic acid.
    Type: Grant
    Filed: October 5, 1990
    Date of Patent: March 10, 1992
    Assignee: Societe Nationale Elf Aquitaine (Production)
    Inventors: Yves Labat, Jean-Pierre Muller, Daniel Litvine
  • Patent number: 5082967
    Abstract: Novel diheteroatom-substituted fatty acid analog substrates of myristoylating enzymes are provided which contain oxyen and/or sulfur in place of two methylene groups in carbon positions from 3 to 13 in the fatty acid chain of a C.sub.13 -C.sub.14 fatty acid analog or alkyl ester thereof in which said oxygen or sulfur atoms are separated by at least one methylene group.
    Type: Grant
    Filed: February 9, 1990
    Date of Patent: January 21, 1992
    Assignee: Washington University
    Inventors: Robert O. Heuckeroth, Steven P. Adams, Jeffrey I. Gordon, George W. Gokel
  • Patent number: 5057622
    Abstract: 3-alkylthiopropionic acids are provided which are a direct addition reaction product of an alkylmercaptan and acrylic acid of an alkali metal salt thereof, the reaction being carried out by heating the reactants in the presence of an aqueous alkaline solution having a pH of at least about 11. The acids can be esterified with pentaerythritol in order to form tetraesters which are especially useful as stabilizers for polymer resins and polymers.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: October 15, 1991
    Assignee: Witco Corporation
    Inventors: Daniel R. Chisholm, Michael H. Fisch, Mark E. Flanagan, Richard D. Peveler
  • Patent number: 5023371
    Abstract: A process for forming thioglycolic acid by contacting in a reaction zone at elevated pressure of at least 250 psig a mixture of monochloroacetic acid and dichloroacetic acid with a molar excess of an alkali metal hydrosulfide to form the alkali metal salt of thioglycolic acid, acidifying said salt and removing the free thioglycolic acid. A preferred process further requires separating any formed thiodiglycolic acid from the resultant liquid phase materials and recycling said acid to the reaction zone.
    Type: Grant
    Filed: May 26, 1987
    Date of Patent: June 11, 1991
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Mosum E. Tsui, Martin B. Sherwin
  • Patent number: 5008432
    Abstract: Activated olefinically unsaturated organic compounds such as esters, acids, ketones, nitriles, and the like, are reacted with hydrogen sulfide in the presence of at least one of magnesium oxide and anion exchange resins catalysts to produce saturated sulfur-containing compounds. In a specific embodiment, unsaturated carboxylates are converted in high yields to mercaptoalkanoates.
    Type: Grant
    Filed: July 11, 1985
    Date of Patent: April 16, 1991
    Assignee: Phillips Petroleum Company
    Inventor: John S. Roberts
  • Patent number: 4966732
    Abstract: 1,2-Dithiolane-3-pentanoic acid (D,L-thioctic acid) of the formula ##STR1## is prepared by a process comprising (a) reacting a 2-(3-alkylthiopropionyl)-cyclopentanone-1 of the formula ##STR2## where R is a C.sub.1 -C.sub.4 alkyl, phenyl or benzyl in aqueous alkaline solution at a temperature of about 20.degree. C. to about 90.degree. C. to form the corresponding carboxylic acid of formula VI ##STR3## (b) reacting the compound of formula VI with an alkyl mercaptan at a temperature between -20.degree. C. and 0.degree. C. to form the corresponding thioketal of formula VII ##STR4## (c) reacting the compound of formula VII with sodium in liquid ammonia at temperature temperture between -60.degree. C. and -10.degree. C.
    Type: Grant
    Filed: July 15, 1987
    Date of Patent: October 30, 1990
    Assignee: Degussa Aktiengesellschaft
    Inventors: Guenes Giray, Klaus Huthmacher, Axel Kleemann, Thomas Lied
  • Patent number: 4942254
    Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula. ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, NR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.
    Type: Grant
    Filed: January 29, 1988
    Date of Patent: July 17, 1990
    Assignee: Union Oil Company of California
    Inventor: Donald C. Young
  • Patent number: 4927960
    Abstract: Novel phosphonium salts of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each is a hydrogen atom or a hydrocarbon group of 1 to 12 carbon atoms which may optionally be substituted; R.sup.3 is a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms which may optionally be substituted; R.sup.4, R.sup.5 and R.sup.6 each is a hydrocarbon group of 1 to 8 carbon atoms which may optionally be substituted; X is a hydroxyl group, a hydroxycarbonyloxy group or a lower alkylcarbonyloxy group, and processes for production of the salts are described. Telomerization catalysts containing said phosphonium salts and processes for production of straight-chain alkadienyl compounds using the same catalysts are also provided.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: May 22, 1990
    Assignee: Kuraray Company, Ltd.
    Inventors: Toshihiko Maeda, Yasuo Tokitoh, Noriaki Yoshimura
  • Patent number: 4900871
    Abstract: Hydrocarbons, and particularly lower molecular weight alkanes and cycloalkanes, may readily be oxidized with air or O.sub.2 to form such products as alcohols, ketones, and the like selectively high yields when there is employed as the catalyst a coordination complex containing an iron center and a halogenated ligand having the structure ##STR1## where Fe is iron; " .circle. " is a ligand; X is a halogen substituent of the ligand; and A is an anion.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: February 13, 1990
    Assignee: Sun Refining and Marketing Company
    Inventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
  • Patent number: 4879249
    Abstract: Novel immunoassay which utilizes an enzyme linked ligand or receptor wherein the enzyme is bacterial luciferase; mercantile kit useful in performing said immunoassay; and compounds utilized in performing said assay.
    Type: Grant
    Filed: March 17, 1986
    Date of Patent: November 7, 1989
    Inventors: Thomas O. Baldwin, Thomas F. Holzman, Paul S. Satoh, Frederick S. Yein
  • Patent number: 4799953
    Abstract: This invention relates to condensation polymers of thiolactic and thioglycolic acids. These polymers, as well as thiolactic acid, 2,2'-dithobisacetic acid, and 2,2'-dithiobispropanoic acid, increase both the rate of plant growth and the concentration of chlorophyll in the plant.
    Type: Grant
    Filed: October 8, 1987
    Date of Patent: January 24, 1989
    Assignee: CPC International Inc.
    Inventors: Morris J. Danzig, Alan M. Kinnersley
  • Patent number: 4734516
    Abstract: The reaction of a zinc compound compound of formula IIICF.sub.3 CCl.sub.2 ZnCl.yL (III)wherein y is 1 or 2 and L is a solvent ligand selected from the group consisting of the N-disubstituted acid amides, N-substituted lactams and organic sulfoxides, with an aldehyde of formula IIR--CHO (II)wherein R is an aliphatic or aromatic hydrocarbon radical or an aliphatic or aromatic heterocyclic radical, gives 1-propanols of formula I ##STR1## in high yields.
    Type: Grant
    Filed: March 19, 1986
    Date of Patent: March 29, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert W. Lang
  • Patent number: 4599469
    Abstract: Process for the hydrogenation of functionally substituted acetylenic compounds employing catalyst comprising nickel boride on an inorganic oxide support is disclosed. Functionally-substituted acetylenic compounds are selectively reduced under mild reaction conditions to give functionally-substituted cis-olefinic compounds in high yield.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: July 8, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Ted H. Cymbaluk, Jim D. Byers, Marvin M. Johnson
  • Patent number: 4497960
    Abstract: The invention declares new chiral, optically active compounds of the general formula ##STR1## wherein a 5 or 6 membered lactol ring (E), with X and Y meaning (CR.sup.1 R.sup.2).sub.n, with n=0 to 2 and R.sup.1, R.sup.2 =H, lower alkyl or aryl in any combination which does not impair the anomeric selectivity of I in forming acetals, is fused in a stereospecific manner to a bicyclo[2.2.
    Type: Grant
    Filed: December 6, 1982
    Date of Patent: February 5, 1985
    Inventor: Christian Noe
  • Patent number: 4490307
    Abstract: There is provided a process for the production of .beta.-mercaptopropionic acid and its esters and nitriles by reacting the corresponding acrylic acid derivatives with trithiocarbonates in aqueous solution.
    Type: Grant
    Filed: June 15, 1983
    Date of Patent: December 25, 1984
    Assignee: Degussa Aktiengesellschaft
    Inventor: Herbert Klenk
  • Patent number: 4464304
    Abstract: A nucleophile substituted unsaturated hydrocarbon based compound is prepared by reacting a compound of the formula: ##STR1## wherein R and R' are hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkoxyalkyl, alkoxy, alkylthioalkyl, or carboxyalkyl or carboxyalkenyl and X is a leaving group selected from the group consisting of chlorine, bromine, and iodine with a nucleophilic reagent.
    Type: Grant
    Filed: June 30, 1982
    Date of Patent: August 7, 1984
    Assignee: Duke University
    Inventors: Ned A. Porter, Carl B. Ziegler, Jr., David H. Roberts
  • Patent number: 4417035
    Abstract: Water-emulsifiable hard waxes consisting of homogeneous copolymers of ethylene with from 1 to 8% by weight, based on copolymer, of one or more .alpha.-olefinically unsaturated C.sub.3 -C.sub.8 -carboxylic acids, and having the following characteristic data:Melt index=1,500 to 20 MFI units, measured at 160.degree. C. under 325 g loadAcid number=10-60Hoppler hardness=400-800 bar, measured at 23.degree. C. by DGF standard method M-III 9a (57).
    Type: Grant
    Filed: November 13, 1981
    Date of Patent: November 22, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Oeder, Wolfram Dietsche, Stefan Weiss, Walter Ziegler, Peter Kueppers, Albert Hettche
  • Patent number: 4384139
    Abstract: A process is disclosed wherein an optically active .beta.-mercaptoalkanoic acid represented by formula (I): ##STR1## wherein R.sub.1 is lower alkyl having from 1 to 4 carbon atoms, is prepared by(1) reacting an optically active .beta.-hydroxyalkanoic acid represented by formula (II): ##STR2## wherein R.sub.1 is the same as defined above, with a halogenating reagent to prepare an optically active .beta.-haloalkanoyl halide represented by formula (III): ##STR3## wherein X is halogen and R.sub.1 is the same as defined above; (2) reacting the .beta.-haloalkanoyl halide with water or an aqueous alkaline solution to prepare an optically active .beta.-haloalkanoic acid represented by formula (IV): ##STR4## wherein X and R.sub.1 are each the same as defined above, or a salt thereof, respectively; and(3) reacting the .beta.
    Type: Grant
    Filed: August 18, 1981
    Date of Patent: May 17, 1983
    Assignee: Kanegafuchi Chemical Industry Company, Limited
    Inventors: Takehisa Ohashi, Masami Shimazaki, Kenji Nomura, Kazunori Kan, Kiyoshi Watanabe
  • Patent number: 4367346
    Abstract: This invention is concerned with the preparation of long-chain carboxylic acids and alcohols from cyclododecanone and acyl chlorides. More specifically, this invention relates to a process for the preparation of 1-triacontanol, CH.sub.3 (CH.sub.2).sub.28 CH.sub.2 OH. Triacontanol acts as a growth stimulant on a wide range of plants to increase dry weight gains, water uptake, water use efficiency and protein synthesis in treated plants.
    Type: Grant
    Filed: April 23, 1981
    Date of Patent: January 4, 1983
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Dane K. Parker
  • Patent number: 4365086
    Abstract: A polyperoxyketal having at least one carboxy group--an acid, hydrocarbon ester, a metal ion, or as part of an anhydride. Illustrations are: n-Butyl .gamma.,.gamma.-bis-(t-butylperoxy) valerate and Barium .gamma.,.gamma.-bis(t-butylperoxy) valerate. These polyperoxyketals are vulcanizing agents for thermoplastic polymers such as rubber and ethylenepropylene rubber.
    Type: Grant
    Filed: June 6, 1963
    Date of Patent: December 21, 1982
    Assignee: Pennwalt Corporation
    Inventors: Wilbur H. McKellin, Orville L. Mageli, Antonio J. D'Angelo
  • Patent number: 4355183
    Abstract: Inhibition of the formation of color bodies and color-forming materials and other contaminants and/or decolorization of discolored sulfur-containing organic compounds containing divalent sulfur by addition of a small amount of oxalic acid.
    Type: Grant
    Filed: August 8, 1979
    Date of Patent: October 19, 1982
    Assignee: Phillips Petroleum Company
    Inventors: Martin E. Nash, Edward E. Huxley
  • Patent number: 4350834
    Abstract: A nucleophile substituted unsaturated hydrocarbon based compound is prepared by reacting a compound of the formula: ##STR1## wherein R and R' are hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkoxyalkyl, alkoxy, alkylthioalkyl, or carboxyalkyl or carboxyalkenyl and X is a leaving group selected from the group consisting of chlorine, bromine, and iodine with a nucleophilic reagent.
    Type: Grant
    Filed: August 27, 1980
    Date of Patent: September 21, 1982
    Assignee: Duke University
    Inventors: Ned A. Porter, Carl B. Ziegler, Jr., David H. Roberts
  • Patent number: 4334094
    Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more palladium-containing catalysts in combination with a Group VB tertiary donor ligand and in the presence of an iodide or bromide promoter.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: June 8, 1982
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4328163
    Abstract: A process for preparing a secondary or tertiary 2-carboxyethyl- or carboxymethylphosphine or a salt thereof comprisessaponifying the corresponding cyanoalkyl phosphine with an aqueous-alcoholic alkali metal hydroxide solution, to prepare the alkali metal salt of the corresponding phosphino carboxylic acid,treating an aqueous solution of the acid salt so produced with a strongly acidic ion exchanger, andneutralizing the resultant free acid with an alkali metal hydroxide, ammonia or an amine when a salt thereof is to be prepared.
    Type: Grant
    Filed: January 17, 1980
    Date of Patent: May 4, 1982
    Assignee: Chemische Werke Huels, A.G.
    Inventor: Peter Hanssle
  • Patent number: 4323702
    Abstract: A process for recovering carboxylic acids with a material of which the main component is a polymeric compound having a pyridine skeletal structure and a crosslinked structure, followed by desorbing the captured carboxylic acids by use of a desorbing agent.
    Type: Grant
    Filed: November 17, 1980
    Date of Patent: April 6, 1982
    Assignee: Koei Chemical Co., Ltd.
    Inventors: Nariyoshi Kawabata, Shinichi Yasuda, Takeshi Yamazaki
  • Patent number: 4322550
    Abstract: Various mercaptoalkanoic acids are recovered from an aqueous medium or water in which they are contained by a liquid-liquid solvent extraction operation employing at least one of an alkanoic acid ester and an alkylene glycol ether. In one embodiment, thioglycolic acid has been extracted with ethyl acetate. In another embodiment, it has been recovered with ethylene glycol monoethyl ether acetate. In a further embodiment, it has been recovered with diethylene glycol diethyl ether.
    Type: Grant
    Filed: October 3, 1980
    Date of Patent: March 30, 1982
    Assignee: Phillips Petroleum Company
    Inventor: James B. Kimble
  • Patent number: 4315867
    Abstract: Secondary and tertiary 2-carboxyethyl or carboxymethylphosphines or a salt thereof, of the formulaR--P(CH.sub.2 COOMe).sub.2 or R--P(CH.sub.2 --CH.sub.2 --COOMe).sub.2whereinMe is hydrogen, an alkali metal or NR'.sub.4 wherein R' is hydrogen, C.sub.1-10 alkyl or C.sub.6-14 aryl, andR is hydrogen or a saturated or unsaturated, aliphatic or cycloaliphatic group of 1-20 carbon atoms and, for the 2-carboxyethylphosphines, also C.sub.6-14 aryl,are useful as components in catalysts for ethylene oligomerization.
    Type: Grant
    Filed: January 17, 1980
    Date of Patent: February 16, 1982
    Assignee: Chemische Werke Huels, Aktiengesellschaft
    Inventor: Peter Hanssle
  • Patent number: 4314842
    Abstract: This invention concerns certain substituted 1,3,4-thiadiazol-2-yl-4-hydroxy-1-methyl-2-imidazolidinones having herbicidal activity, their preparation, and the control of weeds therewith.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: February 9, 1982
    Assignee: PPG Industries, Inc.
    Inventor: Jerome M. Lavanish
  • Patent number: 4273944
    Abstract: A novel method for the selective preparation of the cis isomer of a disubstituted ethylenically unsaturated compound is proposed in which a disubstituted acetylenically unsaturated compound is partially hydrogenated in the presence of, in place of a conventional Lindlar catalyst or a combination of a Lindlar catalyst with an amine, a palladium catalyst borne on an alumina carrier in combination with water and a hydroxide or a basic salt of an alkali metal or an alkaline earth metal. The inventive method is advantageous over conventional methods by the unnecessity of the use of an amine compound which is definitely undesirable when the product is directed to the application in perfumery and by the easiness in handling of the catalyst which can be easily separated from the reaction mixture after completion of the reaction.
    Type: Grant
    Filed: October 30, 1979
    Date of Patent: June 16, 1981
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Shigeru Ohno, Haruya Tezuka, Toshinobu Ishihara
  • Patent number: 4273936
    Abstract: A one-step process is disclosed for forming a carboxylic acid and its anhydride directly from the corresponding olefin which comprises reacting the olefin with carbon monoxide, hydrogen and oxygen in the presence of a stable rhodium complex catalyst. The rhodium catalyst is stabilized by a pentavalent Group V ligand, such as a phosphine oxide. The reaction is preferably conducted in an inert organic solvent. In an alternate embodiment, a carboxylic acid may be obtained by oxidation of an aldehyde (produced, for example, by hydroformylation of the corresponding olefin) in the presence of a rhodium complex catalyst stabilized by a pentavalent Group V ligand. This reaction is also preferably conducted in an inert organic solvent.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: June 16, 1981
    Assignee: Union Carbide Corporation
    Inventors: Rocco A. Fiato, Roy L. Pruett
  • Patent number: 4260820
    Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more ruthenium catalyst components and an iodide or bromide promoter.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: April 7, 1981
    Assignee: Texaco Development Corp.
    Inventor: John F. Knifton
  • Patent number: 4249015
    Abstract: Carboxylic acids and/or esters are prepared by converting the ##STR1## moiety in a 1-substituted 2,2-trihaloethanol, or derivative wherein X represents halogen and R is hydrogen or an acyl group to an organic acid and/or ester grouping of the formula ##STR2## wherein R' is hydrogen or alkyl of 1 to 6 carbon atoms, in the process which comprises reacting the 1-substituted 2,2,2-trihaloethanol or acylated derivative with molecular oxygen in the presence of a catalyst comprising a complex of a transition metal having an atomic number from 21-30, 39-48 or 57-80 and at least one molecule of a ligand containing trivalent nitrogen, phosphorus, arsenic or antimony. This reaction is carried out in a reaction medium comprising an alcohol or aqueous alcohol having 1 to 6 carbon atoms optionally containing an alkali metal, said alcoholic solvent also serving as a reactant source when carboxylic acid esters are formed.
    Type: Grant
    Filed: January 26, 1979
    Date of Patent: February 3, 1981
    Assignee: Shell Oil Company
    Inventors: John A. Schofield, John E. Hawes
  • Patent number: 4178300
    Abstract: A novel process is described for the preparation of novel organic solutions of organooxy magnesium compounds of low viscosity, which solutions are formed in the presence of at least 5 mol % based on the magnesium compound of an organooxy compound of a transition metal of Groups IV through VI of the Periodic Table.
    Type: Grant
    Filed: October 31, 1978
    Date of Patent: December 11, 1979
    Assignee: Stamicarbon, B.V.
    Inventor: Cornelis E. P. V. van den Berg
  • Patent number: 4172211
    Abstract: A process for preparing thioethers of mercaptocarboxylic acids by contacting glycolic acid or bromoacetic acid and a mercaptan in the presence of aqueous hydrogen bromide.
    Type: Grant
    Filed: March 31, 1978
    Date of Patent: October 23, 1979
    Assignee: Chevron Research Company
    Inventor: Shigeto Suzuki
  • Patent number: 4166132
    Abstract: Novel amine and amidine derivatives of di-0-(n-higher alkyl and alkenyl)-glycerols and -propanediols, and their pharmaceutically acceptable acid addition salts, are useful for combating viral infections in mammals. Of particular interest is 1,3-di-0-(n-hexadecyl)-2-0-(3-aminopropyl)-glycerol, and its pharmaceutically acceptable acid addition salts.
    Type: Grant
    Filed: August 18, 1977
    Date of Patent: August 28, 1979
    Assignee: Pfizer Inc.
    Inventor: Allen R. Kraska
  • Patent number: 4154946
    Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.
    Type: Grant
    Filed: June 28, 1978
    Date of Patent: May 15, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Miguel A. Ondetti, Michael E. Condon
  • Patent number: 4143066
    Abstract: A lower carboxylic acid such as acetic acid is separated and recovered from an aqueous medium by the steps which include contacting, in an extraction zone, the aqueous medium with an extracting agent such as trioctyl phosphine oxide dissolved in an organic solvent such as a mixture of paraffins having a boiling range of about 160.degree. C. to 175.degree. C.
    Type: Grant
    Filed: December 16, 1976
    Date of Patent: March 6, 1979
    Assignee: The Dow Chemical Company
    Inventor: Victor Kalcevic
  • Patent number: 4135047
    Abstract: This invention relates to a process for preparing thioethers by the addition of an SH group from a thiol-containing compound, e.g., an alcohol, ester or acid, across at least one double bond of an ethylenically unsaturated compound in the presence of an initiator comprising a pinacol of the general formula: ##STR1## wherein R is phenyl or substituted phenyl, said substituents being members of the group consisting of halogen, alkyloxy and alkyl, said alkyloxy and alkyl containing 1 to 6 carbon atoms.
    Type: Grant
    Filed: March 23, 1978
    Date of Patent: January 16, 1979
    Assignee: W. R. Grace & Co.
    Inventor: Charles R. Morgan
  • Patent number: 4116962
    Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.
    Type: Grant
    Filed: December 3, 1976
    Date of Patent: September 26, 1978
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Miguel Angel Ondetti, Frank Lee Weisenborn
  • Patent number: H78
    Abstract: Energetic diols of the formula ##STR1## wherein R is --H, --NO, --NO.sub.2, --CN, or --CH.sub.2 COOH, and diesters of the formula ##STR2## wherein R is --H, --NO, --NO.sub.2, --CN, --CH.sub.2 COOCH.sub.3, --CH.sub.2 COOCH.sub.2 C(NO.sub.2).sub.2 CH.sub.3, or --CH.sub.2 COOCH.sub.2 C(NO.sub.2).sub.3 and R' is an alkyl, fluoroalkyl, chloroalkyl, aryl, fluoroaryl, chloroalkyl, aralkyl, fluoroaralkyl, chloroaralkyl, or alkene group.
    Type: Grant
    Filed: May 6, 1983
    Date of Patent: July 1, 1986
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst G. Adolph, Michael E. Sitzmann