Patents Examined by Norma S. Milestone
  • Octahydronapthalenes
    Patent number: 4499289
    Abstract: The invention relates to octahydronapthalenes which are useful in antiatherosclerotic agents.
    Type: Grant
    Filed: November 7, 1983
    Date of Patent: February 12, 1985
    Assignee: G. D. Searle & Co.
    Inventors: John S. Baran, Chi-Dean Liang
  • Process for the production of macrocyclic esters and lactones utilizing double metal salt catalysts
    Patent number: 4499288
    Abstract: A process is provided for the thermal depolymerization of polyesters to produce macrocyclic compounds utilizing mixed-metal catalysts. Useful mixed-metal catalysts consist of an aluminum alkoxide or aluminum carboxylate with an alkali metal or magnesium alkoxide or carboxylate, or double metal salts thereof. High yields and enhanced rates of reaction are obtained using the mixed-metal catalysts of this invention.
    Type: Grant
    Filed: June 6, 1983
    Date of Patent: February 12, 1985
    Assignee: National Distillers and Chemical Corporation
    Inventor: Eugene G. Harris
  • Process for preparation of substituted formamidine and substituted N-iminomethyl piperidine
    Patent number: 4499274
    Abstract: An improved process for preparing fenoctimine, which is 4-(diphenylmethyl)-1-[(octylimino)methyl]piperidine by: (1) reacting dimethylformamide with dimethyl sulfate to form a complex; (2) reacting the resultant dimethylformamide/dimethyl sulfate complex with n-octylamine and optionally with dimethylamine; (3) thereafter treating the reaction with aqueous base to form N,N-dimethyl-N'-octyl-formamidine; and (4) reacting said formamidine, without need for further purification, with 4-(diphenylmethyl) piperidine to obtain 4-(diphenylmethyl)-1-[(octylimino)-methyl]piperidine.
    Type: Grant
    Filed: March 17, 1983
    Date of Patent: February 12, 1985
    Assignee: McNeilab, Inc.
    Inventors: Georg Feth, John E. Mills
  • Process for production of methyl 2-tetradecylgycidate
    Patent number: 4499294
    Abstract: An improved process for producing the hypoglycemic compound, methyl 2-tetradecylglycidate, by reacting methyl .alpha.-chloropalmitate with lithium methoxide in the presence of formaldehyde in a dipolar aprotic solvent such as DMF or DMSO.
    Type: Grant
    Filed: January 21, 1983
    Date of Patent: February 12, 1985
    Assignee: McNeilab, Inc.
    Inventor: Cynthia A. Maryanoff
  • Cyclopentanone derivatives
    Patent number: 4497954
    Abstract: Certain substituted cyclopentanone ethylene ketal compounds, and ketones and amides derived therefrom are useful synthetic intermediates for compounds of pharmaceutical interest. A synthetic process for using the intermediates is also described.
    Type: Grant
    Filed: November 15, 1983
    Date of Patent: February 5, 1985
    Assignee: Riker Laboratories, Inc.
    Inventor: Elden H. Banitt
  • Production of epoxy compounds from olefinic compounds
    Patent number: 4496752
    Abstract: Chlorine and tertiary alkanol dissolved in an inert organic solvent are reacted with aqueous alkali to produce tertiary alkyl hypochlorite which is recovered in the organic solvent and reacted with water and olefinically unsaturated compound to produce chlorohydrin and tertiary alkanol. Chlorohydrin and tertiary alkanol recovered in the organic solvent are contacted with aqueous alkali to produce the epoxy compound, and tertiary alkanol recovered in the organic solvent is recycled to hypochlorite production. The process may be integrated with the electrolytic production of chlorine, with an appropriate treatment of the recycle aqueous stream when required.
    Type: Grant
    Filed: May 3, 1979
    Date of Patent: January 29, 1985
    Assignee: The Lummus Company
    Inventors: Abraham P. Gelbein, Joon T. Kwon
  • Saponification of chlorohydrins
    Patent number: 4496753
    Abstract: A chlorohydrin, such as glycerol dichlorohydrin is saponified in two stages, with the first stage being carried out in a high back-mix saponification reactor, and the second stage being carried out in a plug-flow saponification reactor. The use of two different stages improves both selectivity and yield.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: January 29, 1985
    Assignee: Lummus Crest, Inc.
    Inventors: Joon T. Kwon, George D. Suciu
  • Process for the preparation of dehydroacetic acid
    Patent number: 4496747
    Abstract: A process for the preparation of dehydroacetic acid which comprises heating 2,2,6-trimethyl-4H-1,3-dioxin-4-one, preferably at a temperature of about 130.degree. C. to about 160.degree.C., the heating being carried out preferably in the presence of an inert solvent such as xylene and preferably dehydroacetic acid; the solvent being present in an amount of about 0.05 to about 2.0 moles per mole of the compound being heated, the process further comprising recovering dehydroacetic acid so produced.
    Type: Grant
    Filed: April 21, 1983
    Date of Patent: January 29, 1985
    Assignee: Eastman Kodak Company
    Inventor: Robert J. Clemens
  • Stereoselective reduction of 2- or 3-substituted 4-piperidones with sodium borohydride
    Patent number: 4496732
    Abstract: A stereoselective reduction of 2- or 3-substituted 4-piperidones of the formula ##STR1## where R.sub.1 is hydrogen, loweralkyl or benzyl and R.sub.2 is methyl or ethyl, to the di-equatorial isomer of the corresponding 4-piperidinol is described. Said reduction is conducted by use of sodium borohydride in a protic solvent medium at a temperature substantially lower than ambient temperature in the presence of an effective amount of an inorganic acid. Under favorable reaction conditions, the stereoselectivity of the reduction is so high that simple crystallization of the reaction product affords the pure isomer in a commercially acceptable and advantageous process.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: January 29, 1985
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: George E. Lee, Thomas B. K. Lee
  • Analgesic dibenz[b,f]oxepins
    Patent number: 4496582
    Abstract: There are described analgesic dibenz[b,f]oxepins having the general formula ##STR1## wherein n is an odd integer 1-7 inclusive; R is --CO.sub.2 R.sub.1 or --CH.sub.2 OR.sub.2 where R.sub.1 is H, C.sub.1-5 lower alkyl, aralkyl, ##STR2## R.sub.3 being C.sub.1-5 lower alkyl; X and Y are each independently hydrogen, halogen, trifluoromethyl, C.sub.1-5 lower alkoxy, C.sub.1-5 lower alkyl, C.sub.1-5 lower alkylthio, or hydroxy; and the dotted line may be a bond or nothing.
    Type: Grant
    Filed: December 12, 1983
    Date of Patent: January 29, 1985
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Helen H. Ong, Matthew J. Flynn
  • Multidentate macromolecular complex salt clathrates
    Patent number: 4496744
    Abstract: A liquid clathrate of a multidentate macromolecular compound complex salt of the formula:[M(multidentate macromolecular compound).sub.m ].sub.x [Al.sub.n R.sub.3n X].sub.y.pZwherein M is a mono-, di, or trivalent cation, R is a lower alkyl group of 1 to 8 carbon atoms, X is a monovalent, divalent or trivalent anion, n is an integer of 2 to 4, x and y are integers from 1 to 3 and m is 1 to 2, Z is an aromatic hydrocarbon compound and p is an integer from 1 to 40. The present liquid clathrate is useful in separating an aromatic hydrocarbon compound from a non-aromatic hydrocarbon compound as well as from a different aromatic hydrocarbon compound.
    Type: Grant
    Filed: February 28, 1980
    Date of Patent: January 29, 1985
    Assignee: University of Alabama
    Inventor: Jerry L. Atwood
  • Metabolite
    Patent number: 4496734
    Abstract: Synthetic 5-hydroxy-N-(6-oxo-2-piperidylmethyl)-2-(2,2,2-trifluoroethoxy) benzamide. The compound 5-hydroxy-N-(6-oxo-2-piperidylmethyl)-2-(2,2,2-trifluoroethoxy) benzamide is a metabolite of the antiarrhythmic agent 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)-benzamide.
    Type: Grant
    Filed: November 15, 1983
    Date of Patent: January 29, 1985
    Assignee: Riker Laboratories, Inc.
    Inventors: Roy L. McQuinn, William R. Bronn, Elden H. Banitt
  • Epoxycarbacyclin derivatives, their preparation and use
    Patent number: 4496745
    Abstract: Compounds of formula (I): ##STR1## (in which: R.sup.1 and R.sup.2 are the same or different and each represents hydrogen or a hydroxy-protecting group:R.sup.3 represents an alkyl group having from 1 to 12 carbon atoms which is optionally substituted, an alkenyl group having from 2 to 12 carbon atoms, an alkynyl group having from 2 to 6 carbon atoms or a cycloalkyl group which is optionally substituted; andX represents an ethylene group, a trans-vinylene group or an ethynylene group) and salts and esters thereof are useful intermediates in the conversion of 5Z-carbacyclin derivatives to their 5E-isomers and in the preparation of certain other carbacyclin compounds.
    Type: Grant
    Filed: October 25, 1983
    Date of Patent: January 29, 1985
    Assignee: Sankyo Company, Limited
    Inventors: Shigeo Amemiya, Koichi Kojima
  • deA-steroids
    Patent number: 4492797
    Abstract: The present disclosure is directed to 5-oxo- or methylene 17.beta.-hydroxy saturated or unsaturated deA-steroids wherein the 17.alpha.-position contains a propionic acid or propanol substituent and derivatives thereof wherein the hydroxy group at the 17-position forms a lactone ring with the carboxy substituent when the substituent at position 21 is carboxy. The deA-steroids and derivatives of the present disclosure are useful as potassium-sparing diuretics or for flushing oedemas.
    Type: Grant
    Filed: October 4, 1982
    Date of Patent: January 8, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Andor Furst, Peter Keller, Marcel Muller
  • Process for preparing L-ascorbic acid
    Patent number: 4491668
    Abstract: L-ascorbic acid is prepared from sodium 2-keto-L-gulonate by introducing gaseous hydrogen chloride in a molar ratio of about 1.5-2.0 to the sodium-2-keto-L-gulonate into a mixture composed of the sodium 2-keto-L-gulonate, ethanol and acetone at a ratio of 1:0.25-1.00:0.5-2.5 by weight at a temperature of about 25.degree.-75.degree. C. until precipitation of sodium chloride ends, removing the precipitated sodium chloride before L-ascorbic acid begins to crystalize out, maintaining the filtrate or supernatant at a temperature of about 25.degree.-75.degree. C. for a period of 5-100 hours and cooling it to yield crystals of L-ascorbic acid as a final product. A solvent inert to the L-ascorbic acid and 2-keto-L-gulonate may be added to the filtrate or supernatant with a favorable result in obtaining purer intended product.
    Type: Grant
    Filed: March 23, 1983
    Date of Patent: January 1, 1985
    Assignee: Shionogi & Co., Ltd.
    Inventors: Kenji Ikawa, Kanji Tokuyama, Masumi Kiyokawa
  • Macrocyclic carbonates, processes for preparing same, organoleptic uses thereof and intermediates used in said process
    Patent number: 4490544
    Abstract: Described is a class of macrocyclic carbonates defined according to the structure: ##STR1## wherein n is an integer of from 1 up to 8 and m is an integer of from 1 up to 8 and where n and m may be the same or different and organoleptic uses thereof in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfume compositions, colognes and perfumed articles (i.e. solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and perfumed polymers).
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: December 25, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Wilhelmus J. Wiegers, Augustinus G. Van Loveren, Marie R. Hanna, Domenick Luccarelli, Jr., David R. Bowen, Manfred H. Vock
  • Process for 4a'(R),5'-dihydromevinolin
    Patent number: 4490546
    Abstract: Mevinolin is converted to its 4a',5'-dihydro derivative by a route involving protection of the 3',4'-double bond followed by reduction of the 4a',5'-double bond followed by deprotection of the 3',4'-positions.
    Type: Grant
    Filed: June 20, 1983
    Date of Patent: December 25, 1984
    Assignee: Merck & Co., Inc.
    Inventor: Chan-Hwa Kuo
  • Low toxicity radiation sensitizer
    Patent number: 4490543
    Abstract: Bis(5-aminofluorescein)dichloroplatinum(II), and substituted fluoresceinamine derivatives of this compound are disclosed as highly effective radiation sensitizers which enhance the effect of ionizing radiation on tumor cells, but uniquely do so without the usual accompanying high toxicity level to surrounding normal cells. A direct combination, single step reaction synthesis is disclosed for preparing bis(5-aminofluorescein)dichloroplatinum(II) from the reaction between an alkali metal tetrachloroplatinate(II) and 5-aminofluorescein.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: December 25, 1984
    Assignee: University of Northern Iowa Foundation
    Inventors: Barton L. Bergquist, James C. Chang
  • Polyglycidyl hindered aromatic amines
    Patent number: 4487948
    Abstract: Polyglycidyl amines having room temperature latency when blended with curing agents and high heat distortion temperatures when cured are derived from hindered aromatic diamines and epihalohydrins. Cured products obtained from these polyglycidyl amines and curing agents are useful in structural composites, film adhesives, molding compounds and the like.
    Type: Grant
    Filed: March 23, 1983
    Date of Patent: December 11, 1984
    Assignee: Celanese Corporation
    Inventors: David A. Shimp, Richard B. Graver
  • Process for the preparation of bis(perfluoroalkyl-alkylthio)alkanoic acids and lactone intermediates thereof
    Patent number: 4485251
    Abstract: Disclosed is a process for the preparation of a bis(perfluoroalkyl-alkylthio)alkanoic acid of the formula ##STR1## wherein each R.sub.f is independently perfluoroalkyl of 3 to 18 carbon atoms or perfluoroalkoxyperfluoroalkyl of 3 to 18 carbon atoms, or mixtures thereof;each A is independently alkylene of up to 6 carbon atoms or said alkylene interrupted by --O--; N(H)-- or --N(lower alkyl)--;R is hydrogen or alkyl of 1 to 6 carbon atoms;R.sub.1 is hydrogen or lower alkyl; andR.sub.2 is hydrogen, lower alkyl, aryl or aryl substituted lower alkyl;by reacting a perfluoroalkyl-alkyl mercaptan of the formulaR.sub.f --A--SH (II)with a lactone of the formula ##STR2## in the presence of a catalytic amount of a Lewis acid to form a perfluoroalkyl-alkylthio lactone of the formula ##STR3## and reacting said perfluoroalkyl-alkylthio lactone with additional perfluoroalkyl-alkylmercaptan of the formulaR.sub.
    Type: Grant
    Filed: December 23, 1982
    Date of Patent: November 27, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert A. Falk