Chalcogen Of A -c(=x)x- Group, Wherein The X's Are The Same Or Diverse Chalcogens, Bonded Directly To The Carbocyclic Ring Of The Bicyclo Ring System (e.g., Tocopherol Esters, Etc.) Patents (Class 549/410)
  • Publication number: 20040014996
    Abstract: A process is described for continuously preparing chromanol ester derivatives, in particular for continuously preparing carboxylic esters of tocopherols and tocotrienols by continuous acylation with carboxylic acids or carboxylic anhydrides.
    Type: Application
    Filed: May 12, 2003
    Publication date: January 22, 2004
    Inventors: Carsten Oost, Gerd Kaibel, Harald Laas, Peter Schmitt, Jens von Erden
  • Publication number: 20030220301
    Abstract: Metformin salts of lipophilic acids, their pharmaceutical formulations, and methods of administrating the metformin salts for the treatment of hyperglycemia.
    Type: Application
    Filed: February 14, 2003
    Publication date: November 27, 2003
    Applicant: Sonus Pharmaceuticals, Inc.
    Inventors: Manjari Lal, Nagesh Palepu, Dean Kessler
  • Patent number: 6518439
    Abstract: The invention concerns a novel method for preparing vitamin E. More particularly, it concerns a novel method for the condensation of Arimethylhydroquinone and isophytol.
    Type: Grant
    Filed: May 14, 2001
    Date of Patent: February 11, 2003
    Assignee: Aventis Animal Nutrition, S.A.
    Inventors: Jildaz Dhainaut, Thierry Durand
  • Publication number: 20020161246
    Abstract: The present invention is a process for converting trimethylhydroquinone diacetate (TMHQ-DA) into trimethylhydroquinone-1-monoacetate (TMHQ-1-MA) by contacting TMHQ-DA with a lipase to effect an enzymatic monosaponification of the TMHQ-DA. Also provided are methods of making (all-rac)-&agr;-tocopherol and (all-rac)-&agr;-tocopherol acetate.
    Type: Application
    Filed: February 19, 2002
    Publication date: October 31, 2002
    Inventors: Werner Bonrath, Detlef Eisenkraetzer, Valerie Enjolras, Reinhard Karge, Thomas Netscher, Michael Schneider
  • Patent number: 6417223
    Abstract: The present invention provides an antiproliferative compound having the structural formula wherein X is oxygen, nitrogen or sulfur; R1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, carboxylic acid, carboxylate, carboxamide, ester, thioamide, thiolacid, thiolester, saccharide, alkoxy-linked saccharide, amine, sulfonate, sulfate, phosphate, alcohol, ethers and nitriles; R2 is hydrogen, methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide and amine; R3 is selected from the group consisting of hydrogen, methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide and amine; R4 is of methyl, benzyl carboxylic acid, benzyl carboxylate, benzyl carboxamide, benzylester, saccharide and amine; and R5 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, carboxyl, amide and ester. Also provided is a method for inducing apoptosis in a cell comprising administering a composition comprising a compound.
    Type: Grant
    Filed: September 23, 1999
    Date of Patent: July 9, 2002
    Assignee: Research Development Foundation
    Inventors: Bob G. Sanders, Kimberly Kline, Laurence Hurley, Robb Gardner, Marla Menchaca, Weiping Yu, Puthucode N. Ramanan, Shenquan Liu, Karen Israel
  • Patent number: 6387882
    Abstract: The present invention provides novel vitamin E derivatives represented by the following formula (I) wherein: R1 and R2 are the same or different and each denotes hydrogen or methyl, R3 denotes an S-linked SH compound (glutathione, &ggr;-glutamylcysteine, cysteine, penicillamine, an ester thereof or cysteamine), and R4 denotes hydroxyl, a N-substituted amino acid (glycine, &bgr;-alanine, &ggr;-aminobutyric acid, 5-aminovaleric acid, &egr;-aminocaproic acid, anthranilic acid, tranexamic acid, proline, an ester thereof, aminoethylsulfonic acid , aminoethylsulfinic acid) or serotonin, or a pharmacologically acceptable salt thereof, which are useful as hepatopathy suppressing agents, anticataract agents, cerebral metabolism improving agents, antioxidants and cosmetic components.
    Type: Grant
    Filed: June 15, 2000
    Date of Patent: May 14, 2002
    Assignee: Senju Pharmaceutical Co., Ltd.
    Inventors: Kazumi Ogata, Hidetoshi Nakao, Kazuhiko Ito, Takahiro Sakaue, Masahito Iemura, Yutaka Inoue
  • Patent number: 6365758
    Abstract: A process for preparing tocopheryl esters or tocotrienyl esters by acid-catalyzed esterification of a tocopherol or a tocotrienol in a solvent while stirring at elevated temperature, which comprises a) carrying out the esterification with the appropriate carboxylic acid, b) carrying out the esterification with from 2.5 to 6 mol of the carboxylic acid in an aliphatic, cycloaliphatic or aromatic hydrocarbon boiling in the range from 80 to 200° C., or else with from 1.0 to 2.5 mol of the carboxylic acid in a mixture consisting of an aliphatic or cycloaliphatic hydrocarbon boiling in the range from 80 to 200° C.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: April 2, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Joanna Linda von dem Bussche-Hünnefeld, Hagen Jaedicke, Guido Harms, Harald Laas
  • Patent number: 6329535
    Abstract: A process for preparing esterified chroman compounds from 2,6,6-trimethylcylohex-2-ene-1,4-dione, wherein the esterified intermediates are reacted directly to give the desired chroman derivatives without an additional purification step.
    Type: Grant
    Filed: October 20, 2000
    Date of Patent: December 11, 2001
    Assignee: Degussa Dental GmbH & Co. KG
    Inventors: Horst Weigel, Steffen Krill, Hans Joachim Hasselbach, Klaus Huthmacher
  • Patent number: 6222051
    Abstract: Alpha-tocopherol 4-aminobenzoate compounds, represented by formula (I), are prepared by the esterification of alpha-tocopherol with 4-aminobenzoic acid. The esters are converted into the element compounds in vivo, so that they have alpha-tocopherol's biological effect including antioxidation as well as the pharmaceutical and biological effects of 4-aminobenzoic acid, including the promotion of red blood cell formation and metabolism, the role of a growth stimulating factor, keeping the skin healthy, and the prevention of hair decoloration. In said formula (I) R1 and R2 which may be the same or different, each is a hydrogen atom or a linear or branched C1˜C4 alkyl chain.
    Type: Grant
    Filed: October 18, 1999
    Date of Patent: April 24, 2001
    Assignee: SK Corporation
    Inventors: Si-Joon Lee, Hee-Young Jung
  • Patent number: 6136851
    Abstract: The invention relates to an ester. The ester is characterized in that it presents the following chemical formula (I): ##STR1## in which: R.sub.1, R.sub.2 and R.sub.3 independently represent an atom of hydrogen, a methyl radical,A represents the following groups: ##STR2## R.sub.4 and R.sub.5 are identical or different and each represents a chain of the form:--B.sub.m --C.sub.n --B.sub.p --C.sub.q --Hin which:B is the following group: ##STR3## C is the following group: ##STR4## and in which the indices m, n, p, and q are respective integers lying in the range 0 to 4, it being understood that the sum m+n+p+q is limited to integers in the range 0 to 4.The ester can be used for preparing cosmetic or pharmaceutical, in particular dermatological, compositions having activity against radicals, against inflammation, favoring differentiation of keratinocytes, improving skin moisturizing, improving skin grain fineness, and having anti-aging or depigmenting activity.
    Type: Grant
    Filed: November 10, 1999
    Date of Patent: October 24, 2000
    Assignee: LVMH Recherche
    Inventors: Frederic Bonte, Alex Saunois
  • Patent number: 6136985
    Abstract: The present invention provides CLA esters and uses thereof. More particularly, the present invention provides a composition for topical use comprising CLA esters and a topical carrier. In addition, the present invention specifically provides tocopheryl CLA esters, ascorbyl CLA esters and retinyl CLA esters.
    Type: Grant
    Filed: December 21, 1998
    Date of Patent: October 24, 2000
    Assignee: DCV, Inc.
    Inventor: James R. Millis
  • Patent number: 6130343
    Abstract: A process of producing a coated tocopheryl succinate is provided. The process comprises contacting a tocopheryl succinate powder with a solution of a pharmaceutically acceptable binder, said tocopheryl succinate being maintained in a fluidized bed during said contacting by passage of a fluidizing gas through said bed. The solvent is then evaporated from said contacted tocopheryl succinate in said fluidized bed. The temperature of said fluidizing gas when introduced into said bed is sufficiently low, e.g. no higher than about 30.degree. C., such that the bed of tocopheryl succinate remains in a fluidized state during said contacting and said evaporating.
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: October 10, 2000
    Assignee: Henkel Corporation
    Inventors: Jeffrey C. Hunsicker, John F. Verhoeven, F. Scott McCunn
  • Patent number: 6096907
    Abstract: A process for preparing chromanol derivatives of the formula I ##STR1## where n is from 1 to 10,R.sup.1, R.sup.2,R.sup.3, R.sup.4 independently of one another are hydrogen or C.sub.1 -C.sub.4 alkyl,R.sup.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.6 -C.sub.10 aryl, C.sub.7 -C.sub.18 aralkyl, C.sub.7 -C.sub.18 alkylaryl, C.sub.1 -C.sub.22 acyl, or a group protecting the hydroxyl,by reduction of the corresponding 4-oxochromanol derivatives of the formula II ##STR2## comprises reacting the 4-oxochromanol derivatives of the formula II with metallic zinc in the presence of an acid or an acid mixture.Compounds of the formula I having C.sub.1 -C.sub.22 acyl as radical R.sup.5 can also be prepared by the above-described reduction of the compounds of the formula II with hydrogen as radical R.sup.5 and simultaneous or subsequent esterification.
    Type: Grant
    Filed: September 14, 1999
    Date of Patent: August 1, 2000
    Assignee: BASF Aktiengesellscahft
    Inventors: Kai-Uwe Baldenius, Bernhard Bockstiegel, Hagen Jaedicke, Detlef Ruff, Carsten Siedenbiedel, Rainer Sturmer
  • Patent number: 6090810
    Abstract: Aryl-substituted and aryl and (3-oxo-1-propenly)-substituted benzopyran, benzothiopyran, 1,2-dihydroquinoline, and 5,6-dihydronaphthalene derivatives have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action of RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists. For example, the retinoid negative hormone called AGN 193109 effectively increased the effectiveness of other retinoids and steroid hormones in in vitro transactivation assays. Additionally, transactivation assays can be used to identify compounds having negative hormone activity.
    Type: Grant
    Filed: December 30, 1998
    Date of Patent: July 18, 2000
    Assignee: Allergan Sales, Inc.
    Inventors: Elliott S. Klein, Alan T. Johnson, Andrew M. Standeven, Richard L. Beard, Samuel J. Gillett, Tien T. Duong, Sunil Nagpal, Vidyasagar Vuligonda, Min Teng, Roshantha A. Chandraratna
  • Patent number: 6066731
    Abstract: A process for the production of a Mannich reagent comprises reacting formaldehyde, especially paraformaldehyde, with a secondary amine in the complete or almost complete absence of a solvent. An alternative comprises reacting a diaminomethane produced from a secondary amine, formaldehyde, especially paraformaldehyde, as well as water with one another in about equimolar amounts. The invention is also concerned with a process for the aminomethylation of .delta.-tocopherol or of tocopherol mixtures containing this and comprises using a Mannich reagent which has been produced in the above manner. After completion of this aminomethylation process excess Mannich reagent can be separated by distillation and can be reacted with water and formaldehyde, especially paraformaldehyde, in order to regenerate further Mannich reagent suitable for use in the aminomethylation, this regeneration representing a further aspect of the invention. Finally, the invention includes certain novel bis(aminomethyl)-.gamma.-tocopherols.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: May 23, 2000
    Assignee: Roche Vitamins Inc.
    Inventors: Robert Karl Muller, Heinz Schneider
  • Patent number: 6048988
    Abstract: A process for the production of .alpha.-tocopherol esters, derivatives or homologs thereof of the general formula ##STR1## in which the mono- or diester of a hydroquinone is reacted with an allyl alcohol derivative or an allyl alcohol in the presence of zinc halides and proton-liberating acids at a temperature of 25.degree. to 100.degree. C.
    Type: Grant
    Filed: December 21, 1998
    Date of Patent: April 11, 2000
    Assignee: Degussa-Huls AG
    Inventors: Steffen Krill, Frank Hubner, Rainer Hahn, Horst Weigel, Klaus Huthmacher
  • Patent number: 6005122
    Abstract: A process for preparing .alpha.-tocopherol or .alpha.-tocopheryl acetate by reacting 2,3,5-trimethylhydroquinone with isophytol or phytol in the presence of a zinc halide condensation catalyst and a proton donor in a solvent with or without subsequent esterification with acetic anhydride, which comprisesA. carrying out the reaction in a nonpolar solvent which is only slightly water-miscible, if at all andB. introducing the required zinc halide into the reaction in the form of a mixture of from 1 to 4 mol of water per mol of zinc halide.The possibility of introducing the zinc halide required in the process according to the invention in the form of a mixture of zinc halide and water which can be readily handled and metered at from 50 to 200.degree. C.
    Type: Grant
    Filed: December 12, 1997
    Date of Patent: December 21, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Kai-Uwe Baldenius, Wulf Kaiser, Bernhard Bockstiegel, Harald Laas, Bernhard Schulz, Peter Schmitt, Helmut Glietenberg
  • Patent number: 5990322
    Abstract: The present invention relates to novel alpha-tocopherol cyclopropylates, represented by the following formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.2', R.sub.3 and R.sub.3', which may be the same or different, each is a hydrogen atom, a linear or branched C.sub.1 -C.sub.10 alkyl chain, phenyl, acetyl or halogen.
    Type: Grant
    Filed: March 9, 1999
    Date of Patent: November 23, 1999
    Assignee: SK Corporation
    Inventors: Sijoon Lee, Heui-young Cheong
  • Patent number: 5922889
    Abstract: Isochromans and their derivatives have been chemically synthesized. These compounds possess significant phytotoxic activity which may be used as a biodegradable contact herbicide. The synthetic method allows for economic production of these herbicides.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: July 13, 1999
    Assignee: The United States od America as Represented by the Secretary of Agriculture
    Inventors: Horace G. Cutler, George Majetich, Xinrong Tian, Paul Spearing
  • Patent number: 5917060
    Abstract: A process for the preparation of chromanyl derivatives of the formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.8 -alkyl, aryl, aralkyl, Si(R.sup.4).sub.3, C(.dbd.O)R.sup.4 or C.sub.1 -C.sub.4 -alkoxymethyl,R.sup.2 and R.sup.3 are hydrogen or C.sub.1 -C.sub.3 -alkyl, andR.sup.4 is C.sub.1 -C.sub.8 -alkyl or aryl,which comprises decarboxylating 5-carboxychromanyl derivatives of the formula II ##STR2## where the substituents R.sup.1 to R.sup.3 are as defined above and 5-carboxylchromanyl derivatives of the formula II.
    Type: Grant
    Filed: December 17, 1997
    Date of Patent: June 29, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Rosenau, Wolf-Dieter Habicher
  • Patent number: 5869703
    Abstract: Disclosed herein are nonionic vitamin E or polyethoxylated vitamin E derivatives represented by the following formula (I) and a method for the preparation thereof, and polymeric amphiphilic vesicles made therefrom. ##STR1## wherein, n is an integer from 0 to 30, inclusive;A is --CH.sub.2 --CH(CH.sub.3)-- or --CH.dbd.C(CH.sub.3)--;B is --CH.sub.3 at the 5-, 7- or 8- position;m is 1, 2, or 3; andR is residue of acrylate or methacrylate derivatives represented by the following formula (II); ##STR2## wherein, R.sub.1 is H or CH.sub.3.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: February 9, 1999
    Assignee: Pacific Corporation
    Inventors: Young Dae Kim, Jung No Lee, Won Chae Kim, Young Hyun Kim, Min Ki Kim, Myoung Su Ku, Iw Han Cho
  • Patent number: 5869704
    Abstract: The invention relates to a water-dispersible or water-soluble compound having the structure I ##STR1## wherein, R.sup.1,R.sup.2, and R.sup.3 are, independently, hydrogen or methyl, and R.sup.4 is--(CH.sub.2 CH.sub.2 O).sub.n CH.sub.2 CH.sub.2 OH, wherein n is from 10 to 100, wherein compound I is the substantially pure D-enantiomer. The invention further relates to a water-dispersible or water-soluble compound having the structure II ##STR2## wherein, R.sup.1, R.sup.2, and R.sup.3 are, independently, hydrogen or methyl, or the salt thereof, wherein compound II is the substantially pure D-enantiomer. The invention further relates to methods for making the tocotrienol compounds of the present invention.
    Type: Grant
    Filed: August 24, 1998
    Date of Patent: February 9, 1999
    Assignee: Eastman Chemical Company
    Inventor: John A. Hyatt
  • Patent number: 5767290
    Abstract: The present invention relates to a process for preparing protected amines or amino acids. The invention furthermore relates to the use of tocopheryl radicals or radicals derived therefrom as protective groups for amines and amino acids, and to compounds obtained in this process as intermediates and to processes for preparing dipeptides and oligopeptides.
    Type: Grant
    Filed: February 26, 1997
    Date of Patent: June 16, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Rosenau, Wolf-Dieter Habicher, Chen-Loung Chen
  • Patent number: 5750564
    Abstract: Compounds having anti-inflammatory and anti-oxidant activity are disclosed. The compounds are useful in preventing and treating inflammatory disorders through several mechanisms. Methods of treatment employing these properties of the compounds and corresponding pharmaceutical compositions are disclosed.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: May 12, 1998
    Inventors: Mark Hellberg, Pete Delgado, Jon C. Nixon
  • Patent number: 5719180
    Abstract: Described herein is a chroman derivative represented by the following formula: ##STR1## wherein X represents H, --CH.sub.2 OH, --CHO, --COOH, --COOCH.sub.3, --CH.dbd.NOH, --CONH.sub.2, --COCH.sub.3, --CH(OH)CH.sub.3, Br, or CN; Y represents a hydroxyl group which may optionally be protected; R represents an alkyl group, alkenyl group, or aralkyl group; provided that, where X is hydrogen atom, R is an alkyl group, alkenyl group, or aralkyl group each having 16 or more carbon atoms; and a vitamin E-like active medicament comprising said derivative as an active ingredient.
    Type: Grant
    Filed: August 12, 1996
    Date of Patent: February 17, 1998
    Assignee: Koichi Shudo
    Inventors: Koichi Shudo, Masashi Akaike
  • Patent number: 5686632
    Abstract: A process of producing a tocopheryl succinate powder is provided. The process forming a tocopheryl succinate powder into a plastic mass. The plastic mass is then allowed to cool whereupon its sets to a solid state. The solid mass can then be subjected to a size reduction to obtain a tocopherol succinate powder having a desirable particle size, e.g. not more than 5% by weight through a 120-mesh sieve and not more than 5% by weight retained on a 14-mesh sieve.
    Type: Grant
    Filed: August 14, 1996
    Date of Patent: November 11, 1997
    Assignee: Henkel Corporation
    Inventor: Leo Walsh
  • Patent number: 5670668
    Abstract: Disclosed is are the palmitate, stearate and 4-phenylbenzoate esters of D-.gamma.-tocotrienol which are the only known derivatives of D-.gamma.-tocotrienol which are crystalline solids and, therefore, may be utilized in the isolation and purification of D-.gamma.-tocotrienol by crystallization and recrystallization procedures.
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: September 23, 1997
    Assignee: Eastman Chemical Company
    Inventor: John Anthony Hyatt
  • Patent number: 5663389
    Abstract: The present invention refers to compounds having a benzopyranic structure of general formula I ##STR1## wherein R represents a hydrogen atom or an acyl group, useful as intermediates in the synthesis of vitamin E and of other compounds having benzopyranic structure endowed with properties inhibiting the formation of organic peroxides and therefore having antioxidizing activity, and to the process for their preparation.
    Type: Grant
    Filed: March 6, 1996
    Date of Patent: September 2, 1997
    Assignee: Alfa Wassermann S.p.A.
    Inventors: Goffredo Rosini, Claudia Baldazzi, Silvano Piani
  • Patent number: 5627205
    Abstract: New substituted phenoxyisobutyric acids and esters that can be used as medicaments and correspond to the formula: ##STR1## wherein X, A, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and Z are as defined in the description.Those compounds and their physiologically tolerable salts can be used therapeutically.
    Type: Grant
    Filed: August 3, 1995
    Date of Patent: May 6, 1997
    Assignee: Adir Et Compagnie
    Inventors: Gilbert Regnier, Claude Guillonneau, Jean-Paul Vilaine, Albert Lenaers, Christine Breugnot
  • Patent number: 5527926
    Abstract: In accordance with the present invention a novel method and composition for using nonionic contrast media to reduce the risk of clot formation in a diagnostic procedure is disclosed. Novel compositions for such method are also disclosed. The present method comprises employing a triiodinated phenyl contrast agent having a heterocyclic group or a dimeric triiodinated phenyl contrast agent having one or more heterocyclic groups.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: June 18, 1996
    Assignee: Bracco International B.V.
    Inventors: Ramachandran S. Ranganathan, Radhakrishna K. Pillai
  • Patent number: 5510379
    Abstract: .beta.-Carboxy sulfonates of the formula ##STR1## wherein R.sub.1 is aryl, R.sub.3 and R.sub.4 are hydrogen or alkyl, Y is -O-, -S-, or -NR.sub.2 -, and R.sub.5 is alkyl or aryl are potent inhibitors of the enzyme acyl CoA:cholesterol acyltransferase (ACAT) and are thus useful for treating hypercholesterolemia and atherosclerosis.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: April 23, 1996
    Assignee: Warner-Lambert Company
    Inventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
  • Patent number: 5495026
    Abstract: A phenol, a formaldehyde and an unsaturated compound having carbon-carbon double bond are reacted in the presence of a secondary amine and an acid at a temperature of 100.degree. to 250.degree. C., to give a chroman.
    Type: Grant
    Filed: September 13, 1994
    Date of Patent: February 27, 1996
    Assignee: Kuraray Company Ltd.
    Inventors: Eriko Fukumoto, Masahiro Torihara, Yoshin Tamai
  • Patent number: 5482942
    Abstract: This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: January 9, 1996
    Assignee: American Home Products Corporation
    Inventors: Richard M. Soll, Paul J. Dollings
  • Patent number: 5468883
    Abstract: A process for preparing dl-.alpha.-tocopherol or dl-.alpha.-tocopheryl acetate by acid-catalyzed reaction of 2,3,5-trimethylhydroquinone (TMH) with phytol or isophytol in a solvent at elevated temperature, with or without subsequent esterification of the resulting tocopherol with acetic anhydride, entails the reaction being carried out in the presence of a mixture of ortho-boric acid and certain aliphatic di- or tricarboxylic acids, preferably in the presence of a mixture of ortho-boric acid and oxalic acid.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: November 21, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Paul Grafen, Hans Kiefer, Hagen Jaedicke
  • Patent number: 5424457
    Abstract: A process is provided which allows the isolation of sterols and a tocopherol concentrate in high yields from a deodorizer distillate (DOD) mixture obtained from the processing of, for example, soybean oils. Treatment of DOD with methanol at preferably 200.degree.-220.degree. C. in the presence of a monoalkyl- or dialkyl-tin compound results in the conversion of fatty acids and fatty acid esters into fatty acid methyl esters (FAME) and the liberation of free sterols and glycerin without appreciable degradation of tocopherols or sterols. The process can also be carried out in two steps where glycerin is used in the initial step and the fatty acids are converted into glycerides allowing the water of reaction to be removed as it is formed. The FAME produced by both methods are removed by a stripping operation to give a concentrate that allows the isolation of sterols in high yield and high purity and the isolation of a tocopherol concentrate by molecular distillation.
    Type: Grant
    Filed: May 27, 1994
    Date of Patent: June 13, 1995
    Assignee: Eastman Chemical Company
    Inventors: Charles E. Sumner, Jr., Scott D. Barnicki, Martin D. Dolfi
  • Patent number: 5348975
    Abstract: Retinoid like activity is exhibited by compounds of the formula ##STR1## wherein the R.sub.1 -R.sub.6 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl of 1 to 6 carbons; X symbolizes an ester or thioester linkage, Y is lower branched chain alkyl having 2 to 6 carbons, cycloalkyl having 3 to 6 carbons or is (CH.sub.2).sub.n where n is an integer between 0 to 6 or is an alkenyl group of 2 to 6 carbons, and having 1 or 2 double bonds, or an alkynyl group of 2 to 6 carbons; and Z is H, OH, OR', OCOR', --COOH or a pharmaceutically acceptable salt COOR.sub.8, COONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12), CHOR.sub.13 O, --COR', CR'(OR.sub.12).sub.2, or CR'OR.sub.13 O; where R' is an alky, cycloalkyl or alkenyl group containing 1-5 carbons, R.sub.8 is an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons,, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: September 20, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5324744
    Abstract: Retinoid like activity is exhibited by compounds of the formula ##STR1## wherein the R.sub.1 -R.sub.6 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl of 1 to 6 carbons; X symbolizes an ester or thioester linkage, Y is lower branched chain alkyl having 2 to 6 carbons, cycloalkyl having 3 to 6 carbons or is (CH.sub.2).sub.n where n is an integer between 0 to 6 or an alkenyl group of 2 to 6 carbons, and having 1 or 2 double bonds, or an alkynyl group of 2 to 6 carbons; and Z is H, OH, OR', OCOR', --COOH or a pharmaceutically acceptable salt, COOR.sub.8, COONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12), CHOR.sub.13 O, --COR', CR'(OR.sub.12).sub.2, or CR'OR.sub.13 O; where R' is an alkyl, cycloalkyl or alkenyl group containing 1-5 carbons, R.sub.8 is an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.
    Type: Grant
    Filed: July 22, 1992
    Date of Patent: June 28, 1994
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5260294
    Abstract: Racemic Compounds of the formula ##STR1## A is --C.tbd.C--R.sub.6, --CH.sub.2 --CH.sub.2 --R.sub.7 or ##STR2## and the remainder of the variables are as defined in the specification, and their enantiomers and salts thereof are described.The compounds of formula I exhibit activity as inhibitors of 5-lipoxygenase and inhibit lipid peroxidation. They are, therefore, useful in the treatment of diseases caused or aggravated by excess oxidative metabolism of arachidonic acid via the 5-lipoxygenase pathway and in the treatment of inflammation, arthritis, allergies, asthma and psoriasis. The compounds of formula I can also be used to prevent peroxidation of lipids and thus protect lipid membranes from oxidative stress.
    Type: Grant
    Filed: May 27, 1992
    Date of Patent: November 9, 1993
    Assignee: Hoffman-La Roche Inc.
    Inventor: Armin Walser
  • Patent number: 5223510
    Abstract: The subject of the invention is benzofuran, benzothiophene, indole or indolizine compounds of general formula: ##STR1## in which: Het represents one of the groups: ##STR2## in which T,T' and T"represent particularly a group: ##STR3## R and R.sub.a, identical or different, represent X represent --O-- or --S--Y represents a radical ##STR4## These compounds are useful as medecines particularly for the treatment of pathological syndroms of the cardio-vascular system.
    Type: Grant
    Filed: July 26, 1991
    Date of Patent: June 29, 1993
    Assignee: Sanofi
    Inventors: Jean Gubin, Pierre Chatelain, Jean Lucchetti, Gilbert Rosseels, Henri Inion
  • Patent number: 5157132
    Abstract: A process and apparatus is disclosed for separation of fatty acid alkyl esters, carotenoids and tocotrienols from oil. Fatty acids in a vegetable oil are subjected to alcoholic esterification to form an ester-rich layer including fatty acid alkyl esters, carotenoids and tocotrienols. The ester-rich layer is exposed to solvolytic micellization to form a carotenoid-rich layer. The ester-rich layer is separated from the carotenoid-rich layer. The carotenoids in the carotenoid-rich layer are concentrated and can be adsorptively separated from the carotenoid-rich layer. Fatty acid alkyl esters are separated from the ester-rich layer to form a tocotrienol-rich layer. Individual tocotrienols in the tocotrienol-rich layer are adsorptively separated and concentrated.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: October 20, 1992
    Assignee: Carotech Associates
    Inventors: Barrie Tan, Mohammed H. Saleh
  • Patent number: 5134159
    Abstract: Retinoid like activity is exhibited by compounds of the formula ##STR1## wherein the R.sub.1 -R.sub.6 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl of 1 to 6 carbons; X symbolizes an ester or thioester linkage, Y is lower branched chain alkyl having 2 to 6 carbons, cycloalkyl having 3 to 6 carbons or is (CH.sub.2).sub.n where n is an integer between 0 to 6 or is an alkenyl group of 2 to 6 carbons, and having 1 or 2 double bonds, or an alkynyl group of 2 to 6 carbons; and Z is H, OH, OR', OCOR', --COCH or a pharmaceutically acceptable salt, COOR.sub.8, COONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12), CHOR.sub.13 O, --COR', CR'(OR.sub.12).sub.2, or CR'OR.sub.13 O; where R' is an alkyl cycloalkyl or alkenyl group containing 1-5 carbons, R.sub.8 is an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.
    Type: Grant
    Filed: March 26, 1991
    Date of Patent: July 28, 1992
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5132310
    Abstract: Racemic Compounds of the formula ##STR1## A is --C.tbd.C--R.sub.6, --CH.sub.2 --CH.sub.2 --R.sub.7 or ##STR2## R.sub.1 is hydrogen or lower alkanoyl, R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl,R.sub.5 is lower alkyl,R.sub.6 is a heteroaromatic radical or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl lower alkoxy, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, hydroxyimino lower alkyl, amino, amino lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy, pyridyl, or on adjacent carbons can be ##STR3## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R" hydrogen or lower alkyl,R.sub.
    Type: Grant
    Filed: December 14, 1990
    Date of Patent: July 21, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Armin Walser
  • Patent number: 5110955
    Abstract: The invention relates to a process for the manufacture of vinylchromanes. This process is concerned with the manufacture of the compounds having the formula ##STR1## wherein R.sup.o is hydrogen or a cleavable protecting group, and comprises cyclizing a compound having the formula ##STR2## wherein R.sup.o is defined above and R.sup.1 is--CH.sub.2 --CH.sub.2 --C(W)(CH.sub.3)--CH.dbd.CH.sub.2 or--CH.sub.2 --CH.sub.2 C(CH.sub.3).dbd.CH--CH.sub.2 --Wwhere W is a leaving group,by means of a chiral transition metal-diphosphine complex.The compounds of formula I are useful intermediates, e.g. in the manufacture of (R,R,R)-.alpha.-tocopherol.
    Type: Grant
    Filed: April 5, 1990
    Date of Patent: May 5, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Andreas Knierzinger, Michelangelo Scalone
  • Patent number: 5102895
    Abstract: The novel vitamin E derivative provides an excellent antihyperlipemic effect and is defined by the formula (I): ##STR1## wherein R represents a nicotinoyl group; and m is an integer of from 2 to 5 while n is an integer of from 3 to 6, provided that n is larger than m.
    Type: Grant
    Filed: December 31, 1990
    Date of Patent: April 7, 1992
    Assignee: Eisai Co., Ltd.
    Inventors: Noriyasu Hirose, Kimio Hamamura, Takaharu Nakamura, Kiiti Ema, Takashi Banba, Tetsuya Nakamura, Hidetoshi Kawashima, Yuuichi Inai, Noritoshi Sano, Yuko Miyauchi, Shizumasa Kijima
  • Patent number: 5015661
    Abstract: Racemic Compounds of the formula ##STR1## A is --C.tbd.C--R.sub.6, --CH.sub.2 --CH.sub.2 --R.sub.7 or ##STR2## R.sub.1 is hydrogen or lower alkanoyl, R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl,R.sub.5 is lower alkyl,R.sub.6 is a heteroaromatic radical or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl lower alkoxy, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, hydroxyimino lower alkyl, amino, amino lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy, pyridyl, or on adjacent carbons can be ##STR3## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R" hydrogen or lower alkyl,R.sub.
    Type: Grant
    Filed: June 16, 1989
    Date of Patent: May 14, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Armin Walser
  • Patent number: 4983779
    Abstract: An improved process for the preparation of vinyl ethers by the coupling reaction of an ester of the formula ##STR1## with a carbonyl containing compound of the formula ##STR2## wherein A and R are passive organic groups and OY is a hydroxyl group or OP where P is a protecting group is described. The ester and the carbonyl containing compound are reacted in an organic solvent with a titanium salt, a metallic reducing agent and an amine base to provide the vinyl ether. The reaction is safe and produces high yields. The vinyl ethers are useful for producing dioxetanes which produce light upon triggering.
    Type: Grant
    Filed: December 14, 1989
    Date of Patent: January 8, 1991
    Assignee: The Board of Governors of Wayne State University
    Inventor: Arthur P. Schaap
  • Patent number: 4870196
    Abstract: A method of preparing powdered, free-flowing tocopheryl succinate having a high bulk density comprising melting a mixture of tocopheryl succinate and wax, spraying the melt in a spraying zone containing a cloud of a powdering agent consisting of fine tocopheryl succinate and an additional powdering agent, and maintaining the product formed in a fluidized state by introducing cooling air until the tocopheryl succinate particles have hardened, and separating the product formed into a product fraction and a fine fraction, and recyclying the fine fraction to the spraying zone.
    Type: Grant
    Filed: February 24, 1988
    Date of Patent: September 26, 1989
    Assignee: Danochemo A/S
    Inventor: Bitten Thorengaard
  • Patent number: 4861580
    Abstract: Methods and compositions are described for the preparation of alpha-tocopherol vesicles, the bilayers of which comprise a salt form of an organic acid derivative of alpha-tocopherol such as the Tris salt form of alpha-tocopherol hemisuccinate. The method is rapid and efficient and does not require the use of organic solvents. The alpha-tocopherol vesicles may be used to entrap compounds which are insoluble in aqueous solutions. Such preparations are especially useful for entrapping bioactive agents of limited solubility, thus enabling administration in vivo.
    Type: Grant
    Filed: September 24, 1986
    Date of Patent: August 29, 1989
    Assignee: The Liposome Company, Inc.
    Inventors: Andrew S. Janoff, Lois E. Bolcsak, Alan L. Weiner, Paul A. Tremblay, Michael V. W. Bergamini, Robert L. Suddith
  • Patent number: 4824971
    Abstract: Novel 2-halochromans and their coupling to various nucleophiles to produce Vitamin E and as well as novel intermediates for Vitamin E.
    Type: Grant
    Filed: January 21, 1988
    Date of Patent: April 25, 1989
    Assignee: Hoffman-La Roche Inc.
    Inventor: Noal Cohen
  • Patent number: 4752646
    Abstract: Novel 2-halochromans and their coupling to various nucleophiles to produce Vitamin E and as well as novel intermediates for Vitamin E.
    Type: Grant
    Filed: November 20, 1986
    Date of Patent: June 21, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Noal Cohen