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)
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Publication number: 20040014996Abstract: 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: ApplicationFiled: May 12, 2003Publication date: January 22, 2004Inventors: Carsten Oost, Gerd Kaibel, Harald Laas, Peter Schmitt, Jens von Erden
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Publication number: 20030220301Abstract: Metformin salts of lipophilic acids, their pharmaceutical formulations, and methods of administrating the metformin salts for the treatment of hyperglycemia.Type: ApplicationFiled: February 14, 2003Publication date: November 27, 2003Applicant: Sonus Pharmaceuticals, Inc.Inventors: Manjari Lal, Nagesh Palepu, Dean Kessler
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Patent number: 6518439Abstract: 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: GrantFiled: May 14, 2001Date of Patent: February 11, 2003Assignee: Aventis Animal Nutrition, S.A.Inventors: Jildaz Dhainaut, Thierry Durand
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Publication number: 20020161246Abstract: 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: ApplicationFiled: February 19, 2002Publication date: October 31, 2002Inventors: Werner Bonrath, Detlef Eisenkraetzer, Valerie Enjolras, Reinhard Karge, Thomas Netscher, Michael Schneider
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Patent number: 6417223Abstract: 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: GrantFiled: September 23, 1999Date of Patent: July 9, 2002Assignee: Research Development FoundationInventors: Bob G. Sanders, Kimberly Kline, Laurence Hurley, Robb Gardner, Marla Menchaca, Weiping Yu, Puthucode N. Ramanan, Shenquan Liu, Karen Israel
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Patent number: 6387882Abstract: 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: GrantFiled: June 15, 2000Date of Patent: May 14, 2002Assignee: Senju Pharmaceutical Co., Ltd.Inventors: Kazumi Ogata, Hidetoshi Nakao, Kazuhiko Ito, Takahiro Sakaue, Masahito Iemura, Yutaka Inoue
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Patent number: 6365758Abstract: 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: GrantFiled: January 26, 1998Date of Patent: April 2, 2002Assignee: BASF AktiengesellschaftInventors: Joanna Linda von dem Bussche-Hünnefeld, Hagen Jaedicke, Guido Harms, Harald Laas
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Patent number: 6329535Abstract: 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: GrantFiled: October 20, 2000Date of Patent: December 11, 2001Assignee: Degussa Dental GmbH & Co. KGInventors: Horst Weigel, Steffen Krill, Hans Joachim Hasselbach, Klaus Huthmacher
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Patent number: 6222051Abstract: 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: GrantFiled: October 18, 1999Date of Patent: April 24, 2001Assignee: SK CorporationInventors: Si-Joon Lee, Hee-Young Jung
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Patent number: 6136851Abstract: 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: GrantFiled: November 10, 1999Date of Patent: October 24, 2000Assignee: LVMH RechercheInventors: Frederic Bonte, Alex Saunois
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Patent number: 6136985Abstract: 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: GrantFiled: December 21, 1998Date of Patent: October 24, 2000Assignee: DCV, Inc.Inventor: James R. Millis
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Patent number: 6130343Abstract: 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: GrantFiled: August 29, 1996Date of Patent: October 10, 2000Assignee: Henkel CorporationInventors: Jeffrey C. Hunsicker, John F. Verhoeven, F. Scott McCunn
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Patent number: 6096907Abstract: 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: GrantFiled: September 14, 1999Date of Patent: August 1, 2000Assignee: BASF AktiengesellscahftInventors: Kai-Uwe Baldenius, Bernhard Bockstiegel, Hagen Jaedicke, Detlef Ruff, Carsten Siedenbiedel, Rainer Sturmer
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Patent number: 6090810Abstract: 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: GrantFiled: December 30, 1998Date of Patent: July 18, 2000Assignee: 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
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Patent number: 6066731Abstract: 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: GrantFiled: March 22, 1996Date of Patent: May 23, 2000Assignee: Roche Vitamins Inc.Inventors: Robert Karl Muller, Heinz Schneider
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Patent number: 6048988Abstract: 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: GrantFiled: December 21, 1998Date of Patent: April 11, 2000Assignee: Degussa-Huls AGInventors: Steffen Krill, Frank Hubner, Rainer Hahn, Horst Weigel, Klaus Huthmacher
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Patent number: 6005122Abstract: 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: GrantFiled: December 12, 1997Date of Patent: December 21, 1999Assignee: BASF AktiengesellschaftInventors: Kai-Uwe Baldenius, Wulf Kaiser, Bernhard Bockstiegel, Harald Laas, Bernhard Schulz, Peter Schmitt, Helmut Glietenberg
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Patent number: 5990322Abstract: 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: GrantFiled: March 9, 1999Date of Patent: November 23, 1999Assignee: SK CorporationInventors: Sijoon Lee, Heui-young Cheong
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Patent number: 5922889Abstract: 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: GrantFiled: June 21, 1996Date of Patent: July 13, 1999Assignee: The United States od America as Represented by the Secretary of AgricultureInventors: Horace G. Cutler, George Majetich, Xinrong Tian, Paul Spearing
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Patent number: 5917060Abstract: 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: GrantFiled: December 17, 1997Date of Patent: June 29, 1999Assignee: BASF AktiengesellschaftInventors: Thomas Rosenau, Wolf-Dieter Habicher
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Patent number: 5869703Abstract: 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: GrantFiled: October 28, 1997Date of Patent: February 9, 1999Assignee: Pacific CorporationInventors: Young Dae Kim, Jung No Lee, Won Chae Kim, Young Hyun Kim, Min Ki Kim, Myoung Su Ku, Iw Han Cho
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Patent number: 5869704Abstract: 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: GrantFiled: August 24, 1998Date of Patent: February 9, 1999Assignee: Eastman Chemical CompanyInventor: John A. Hyatt
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Patent number: 5767290Abstract: 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: GrantFiled: February 26, 1997Date of Patent: June 16, 1998Assignee: BASF AktiengesellschaftInventors: Thomas Rosenau, Wolf-Dieter Habicher, Chen-Loung Chen
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Patent number: 5750564Abstract: 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: GrantFiled: September 12, 1995Date of Patent: May 12, 1998Inventors: Mark Hellberg, Pete Delgado, Jon C. Nixon
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Patent number: 5719180Abstract: 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: GrantFiled: August 12, 1996Date of Patent: February 17, 1998Assignee: Koichi ShudoInventors: Koichi Shudo, Masashi Akaike
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Patent number: 5686632Abstract: 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: GrantFiled: August 14, 1996Date of Patent: November 11, 1997Assignee: Henkel CorporationInventor: Leo Walsh
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Patent number: 5670668Abstract: 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: GrantFiled: July 3, 1996Date of Patent: September 23, 1997Assignee: Eastman Chemical CompanyInventor: John Anthony Hyatt
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Patent number: 5663389Abstract: 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: GrantFiled: March 6, 1996Date of Patent: September 2, 1997Assignee: Alfa Wassermann S.p.A.Inventors: Goffredo Rosini, Claudia Baldazzi, Silvano Piani
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Patent number: 5627205Abstract: 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: GrantFiled: August 3, 1995Date of Patent: May 6, 1997Assignee: Adir Et CompagnieInventors: Gilbert Regnier, Claude Guillonneau, Jean-Paul Vilaine, Albert Lenaers, Christine Breugnot
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Patent number: 5527926Abstract: 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: GrantFiled: June 6, 1995Date of Patent: June 18, 1996Assignee: Bracco International B.V.Inventors: Ramachandran S. Ranganathan, Radhakrishna K. Pillai
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Patent number: 5510379Abstract: .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: GrantFiled: December 19, 1994Date of Patent: April 23, 1996Assignee: Warner-Lambert CompanyInventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
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Patent number: 5495026Abstract: 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: GrantFiled: September 13, 1994Date of Patent: February 27, 1996Assignee: Kuraray Company Ltd.Inventors: Eriko Fukumoto, Masahiro Torihara, Yoshin Tamai
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Patent number: 5482942Abstract: 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: GrantFiled: June 28, 1994Date of Patent: January 9, 1996Assignee: American Home Products CorporationInventors: Richard M. Soll, Paul J. Dollings
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Patent number: 5468883Abstract: 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: GrantFiled: September 9, 1994Date of Patent: November 21, 1995Assignee: BASF AktiengesellschaftInventors: Paul Grafen, Hans Kiefer, Hagen Jaedicke
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Patent number: 5424457Abstract: 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: GrantFiled: May 27, 1994Date of Patent: June 13, 1995Assignee: Eastman Chemical CompanyInventors: Charles E. Sumner, Jr., Scott D. Barnicki, Martin D. Dolfi
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Patent number: 5348975Abstract: 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: GrantFiled: October 27, 1993Date of Patent: September 20, 1994Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5324744Abstract: 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: GrantFiled: July 22, 1992Date of Patent: June 28, 1994Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5260294Abstract: 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: GrantFiled: May 27, 1992Date of Patent: November 9, 1993Assignee: Hoffman-La Roche Inc.Inventor: Armin Walser
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Patent number: 5223510Abstract: 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: GrantFiled: July 26, 1991Date of Patent: June 29, 1993Assignee: SanofiInventors: Jean Gubin, Pierre Chatelain, Jean Lucchetti, Gilbert Rosseels, Henri Inion
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Patent number: 5157132Abstract: 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: GrantFiled: May 18, 1990Date of Patent: October 20, 1992Assignee: Carotech AssociatesInventors: Barrie Tan, Mohammed H. Saleh
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Patent number: 5134159Abstract: 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: GrantFiled: March 26, 1991Date of Patent: July 28, 1992Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5132310Abstract: 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: GrantFiled: December 14, 1990Date of Patent: July 21, 1992Assignee: Hoffmann-La Roche Inc.Inventor: Armin Walser
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Patent number: 5110955Abstract: 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: GrantFiled: April 5, 1990Date of Patent: May 5, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Andreas Knierzinger, Michelangelo Scalone
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Patent number: 5102895Abstract: 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: GrantFiled: December 31, 1990Date of Patent: April 7, 1992Assignee: 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
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Patent number: 5015661Abstract: 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: GrantFiled: June 16, 1989Date of Patent: May 14, 1991Assignee: Hoffmann-La Roche Inc.Inventor: Armin Walser
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Patent number: 4983779Abstract: 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: GrantFiled: December 14, 1989Date of Patent: January 8, 1991Assignee: The Board of Governors of Wayne State UniversityInventor: Arthur P. Schaap
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Patent number: 4870196Abstract: 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: GrantFiled: February 24, 1988Date of Patent: September 26, 1989Assignee: Danochemo A/SInventor: Bitten Thorengaard
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Patent number: 4861580Abstract: 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: GrantFiled: September 24, 1986Date of Patent: August 29, 1989Assignee: The Liposome Company, Inc.Inventors: Andrew S. Janoff, Lois E. Bolcsak, Alan L. Weiner, Paul A. Tremblay, Michael V. W. Bergamini, Robert L. Suddith
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Patent number: 4824971Abstract: Novel 2-halochromans and their coupling to various nucleophiles to produce Vitamin E and as well as novel intermediates for Vitamin E.Type: GrantFiled: January 21, 1988Date of Patent: April 25, 1989Assignee: Hoffman-La Roche Inc.Inventor: Noal Cohen
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Patent number: 4752646Abstract: Novel 2-halochromans and their coupling to various nucleophiles to produce Vitamin E and as well as novel intermediates for Vitamin E.Type: GrantFiled: November 20, 1986Date of Patent: June 21, 1988Assignee: Hoffmann-La Roche Inc.Inventor: Noal Cohen