Phenolic Hydroxy Or Metallate Patents (Class 560/75)
  • Patent number: 6878843
    Abstract: A process for the preparation of a compound of formula (I) wherein R1 and R2 are each independently of the other C1-C8alkyl, cyclopentyl or cyclohexyl, m is 1, 2 or 3, preferably 2, n is an integer from 1 to 30, and R3 is an n-valent radical from linear or branched C4-C30alkyl, which is optionally interrupted by one or more oxygen atoms, or (when n=1-12) an n-valent radical from C5-C12cycloalkyl, or a radical R4—[NR5—CmH2m—]p, R4 is hydrogen, an n-valent radical from linear or branched C4-C30alkyl, which is optionally interrupted by one or more —NR5— groups, or (when n=1-12) an n-valent radical from C5-C12cycloalkyl, R5 radicals, each independently of any other(s), are hydrogen or methyl or —CmH2m—, preferably hydrogen, and p corresponds to the number of —[NR5—CmH2m—] groups that gives n —CmH2m— radicals per molecule, by reaction of a compound of formula (II) wherein R is C1-C3alkyl, with a compound of formula (III) R3(OH)n??(III) wherein R3 and n have the definitions given, wherein the reaction
    Type: Grant
    Filed: June 14, 2001
    Date of Patent: April 12, 2005
    Assignee: Ciba Specialty Chemicals Corp.
    Inventor: Christoph Kleiner
  • Publication number: 20040258743
    Abstract: A class of UVA- and UVB-absorbing esters has been derived by modifying hydroxy triglycerides and other acyltriglycerides with any of a variety of cinnamic acids. The esterification reactions are preferably conducted at elevated temperatures without a catalyst. The resultant agents have the advantage of being synthesized from natural materials, while providing a value-added use for the oil. They are readily formulated into standard UV-absorbing daily-wear cosmetic, hair and skin care, and sunscreen formulations.
    Type: Application
    Filed: June 17, 2003
    Publication date: December 23, 2004
    Inventors: David L. Compton, Terry A. Isbell, Rogers E. Harry-O'kuru
  • Publication number: 20040209951
    Abstract: This invention relates to novel resveratrol analogs of the formula given below; wherein R, R1, R2 and R3 are: 1. R=OH, R1=R2=R3=H; 2. R=OH, R1=Br, R2=R3=H; 3. R=R1=OH, R2=R3=H; 4. R=R1=R3=H, R2=3,4,5-trihydroxybenzoyl; 5. R=R1=H, R2=R3=3,4,5-trihydroxybenzoyl; 6. R=R1=R3=H, R2=3,4-dihydroxycinnamoyl; 7. R=R1=R3=H, R2=3,4,5-trihydroxycinnamoyl; 8. R=R1=R3=H, R2=—CH2CH2N(CH3)2; 9. R=R1=R3=H, R2=—COCH2NH2.HCl. These compounds exhibited high antioxidant properties and are useful in food industry and in cosmetics. The compounds may be used in pharmaceutical composition as an antioxidant or free radical scavenger.
    Type: Application
    Filed: February 13, 2004
    Publication date: October 21, 2004
    Inventors: Ganga Raju Gokaraju, Rama Raju Gokaraju, Venkata Subbaraju Gottumukkala, Venkateswarlu Somepalli
  • Publication number: 20040209949
    Abstract: The present invention relates to the use of certain resorcinol derivatives as skin lightening agents.
    Type: Application
    Filed: May 5, 2004
    Publication date: October 21, 2004
    Inventors: Andrew Francis Browning, Eric William Collington, Martin James Procter, Joanna Victoria Geden
  • Patent number: 6787663
    Abstract: A composition of an antioxidant of the formula where R3 is an alkyl group of 2 to 6 carbon atoms, and a dispersant or a detergent, is a useful additive package for lubricant compositions.
    Type: Grant
    Filed: October 30, 2002
    Date of Patent: September 7, 2004
    Assignee: The Lubrizol Corporation
    Inventors: Paul E. Adams, Thomas J. Wolak
  • Publication number: 20040122092
    Abstract: The present invention relates to novel hydroxyphenylundecane derivatives of the formula (I), 1
    Type: Application
    Filed: October 1, 2003
    Publication date: June 24, 2004
    Applicant: Aventis Pharma Deutschland GmbH
    Inventors: Cordula Hopmann, Martin Knauf, Mark Bronstrup, Astrid Markus-Erb, Luigi Toti
  • Publication number: 20030157035
    Abstract: A compound of formula I 1
    Type: Application
    Filed: December 20, 2001
    Publication date: August 21, 2003
    Applicant: EM Industries
    Inventor: Ratan K. Chaudhuri
  • Patent number: 6559335
    Abstract: The present invention relates to an improved process for the preparation of 3-aryl-2-hydroxy propanoic acid derivatives of the formula (1) useful as an intermediate for the preparation of many pharmaceutically active compounds.
    Type: Grant
    Filed: April 17, 2001
    Date of Patent: May 6, 2003
    Assignee: Dr. Reddy's Laboratories Limited
    Inventors: Potlapally Rajender Kumar, Siripragada Mahender Rao, Kotra Narasimha Murthy, Sirisilla Raju, Mamillapalli Ramabhadra Sarma, Gaddam Om Reddy
  • Patent number: 6458523
    Abstract: New compounds of the formula I are described, wherein n is >1; X is O or NR4; L is a n-valent linking group defined in claim 1 and R1 is H, halogen, C1-C25-alkyl, C3-C25-alkenyl, unsubstituted or by C1-C4-alkyl substituted C5-C8-cycloalkyl; R2 and R3 independently of each other are C1-C4-alkyl, or together with the carbon atom they are bonded to, form a carbocyclic C5-C7 ring, especially C5-C7 cycloalkylene; and m is 1-20, especially 2-4. Compounds of the formula I are active as Dox-scavengers in color photographic material.
    Type: Grant
    Filed: January 7, 2002
    Date of Patent: October 1, 2002
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Suruliappa Gowper Jeganathan, Stéphane Biry
  • Patent number: 6444278
    Abstract: The present invention relates to 2,6-di-tert-butylphenols of the formula I in which R, A1 A2, Z1, Z2 m and n are as defined herein, and their use as stabilizers or antioxidants.
    Type: Grant
    Filed: October 10, 1997
    Date of Patent: September 3, 2002
    Assignee: Merck Patent Gesellschaft Mit Beschraenkter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause
  • Patent number: 6444839
    Abstract: Rosemarinic acid or its concentrate is made from seeds of lamiaceous plants in a predetermined period of germination. The method makes it possible to make the rosemarinic acid in any period through the year. High productivity can be achieved by small production facility since high-density cultivation of germinated seed is possible and a cultivation period is short. An amount of rosemarinic acid is rapidly increased after start of germination, and an increasing amount usually becomes maximum five to eight days after start of cultivation. Power obtained by pulverizing dry germinated seeds contains 3 to 5% of rosemarinic acid and can be used for various purposes. An extract obtained by water soluble alcohol from the powder and a fraction obtained by fractioning the extract by an organic solvent are concentrated containing about 15% and 30% of rosemarinic acid respectively. When each concentrate is processed by column chromatography, isolated 99%-rosemarinic acid is obtained.
    Type: Grant
    Filed: June 28, 2000
    Date of Patent: September 3, 2002
    Assignee: Salad Cosmo Co., Ltd.
    Inventor: Takeo Murui
  • Patent number: 6436991
    Abstract: Ferulate compounds derived from extracts from the plant Commiphora wightii are used in compositions and methods for prevention and treatment of abnormal cell growth and proliferation in inflammation, neoplasia and cardiovascular disease.
    Type: Grant
    Filed: May 21, 2001
    Date of Patent: August 20, 2002
    Assignees: Sabinsa Corporation, Sami Chemicals & Extracts (P) Ltd.
    Inventors: Muhammed Majeed, Vladimir Badmaev, Rajinder Kumar Bammi, Subbalakshmi Prakash, Sankaran Natarajan
  • Patent number: 6387951
    Abstract: Compounds having Formulas 5 and 6 wherein the symbols have the meaning defined in the specification are inhibitors of the cytochrome P450RAI (retinoic acid inducible) enzyme, and are used for treating diseases responsive to treatment by retinoids.
    Type: Grant
    Filed: August 29, 2000
    Date of Patent: May 14, 2002
    Assignee: Allergan Sales, Inc.
    Inventors: Jayasree Vasudevan, Alan T. Johnson, Liming Wang, Dehua Huang, Roshantha A. Chandraratna
  • Patent number: 6358431
    Abstract: A method of imparting a water repellent surface to a hydrophilic substrate which comprises contacting the substrate with a solution or dispersion of a suitable calixarene in a liquid medium.
    Type: Grant
    Filed: February 24, 1999
    Date of Patent: March 19, 2002
    Assignee: The University of Sheffield
    Inventors: Charles James Matthew Stirling, Frank Davis
  • Publication number: 20020022731
    Abstract: A description is given of a process for the transesterification of carboxylic esters, characterized in that the catalyst used is a tin(IV) compound comprising a radical of the formula 1
    Type: Application
    Filed: March 29, 2001
    Publication date: February 21, 2002
    Inventors: Benoit Pugin, Benoit Dubuis, Adrian Muller
  • Patent number: 6331565
    Abstract: This invention relates to the new use of dicaffeoylquinic acid derivatives for treating Hepatitis B and diseases associated with retrovirus (such as HIV), the new caffeoylquinic acid derivatives and the composition containing the same.
    Type: Grant
    Filed: March 1, 1999
    Date of Patent: December 18, 2001
    Assignee: Institute of Radiation Medicine Academy of Military Medical Sciences of the PLA
    Inventors: Junxing Dong, Zhongming Tang, Zhibao Mi, Bingji Wang
  • Patent number: 6326510
    Abstract: The invention relates to novel biaromatic compounds having general formula I and their use in pharmaceutical compositions for use in human and veterinary medicine, in particular for treating dermatological, rheumatic, respiratory, cardiovascular, and ophthalmological disorders, and for use in cosmetic compositions.
    Type: Grant
    Filed: January 8, 1999
    Date of Patent: December 4, 2001
    Assignee: Centre International de Recherches Dermatologiques
    Inventor: Jean-Michel Bernardon
  • Patent number: 6303052
    Abstract: An antioxidant composition comprising at least one compound having the formula: wherein R1 and R2 are each hydrocarbon groups having from 1 to 8 carbon atoms, a is from 1 to 3, R3 is a linear alkyl group having from 4 to 22 carbon atoms, and R4 is a linear alkyl group having from 6 to 24 carbon atoms.
    Type: Grant
    Filed: March 2, 1999
    Date of Patent: October 16, 2001
    Assignee: Condea Vista Company
    Inventors: Shirley A. Moy, Kurt W. McWilliams
  • Patent number: 6291703
    Abstract: Substituted hydroxyhydrocinnamate esters of the formula (I) where R is alkyl, n is 0 to 2, m is 1 to 4 and A is alkyl, interrupted or uninterrupted alkylene, alkanetriyl or pentaerythrityl, are prepared by continuous transesterification of the corresponding lower alkyl mono-ester with an alkanol or polyol of the formula A-(OH)m. This novel process comprises continuously introducing into and reacting the reactants in a heated distillation column reactor having a reaction zone which contains a solid, heterogeneous transesterification catalyst to form the compound of formula (I) and the corresponding lower alkanol; separating the products so formed based on their difference in volatility; and continuously removing said products from the distillation column at a steady rate, thereby preventing the reaction mixture from reaching chemical equilibrium.
    Type: Grant
    Filed: January 28, 1999
    Date of Patent: September 18, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Robert Anthony Schaerfl, Jr., Michael James Day, Sean Peter Piecuch, Ronald Robert Tellier
  • Patent number: 6184411
    Abstract: The invention is directed to an improved process for the preparation of a compound of formula (I) wherein R is alkyl, n is 0 to 2, m is 1 to 4 and A is alkyl, interrupted or uninterrupted alkylene, alkanetriyl or pentaerythrityl, by transesterifying the corresponding lower alkyl with a higher alkanol of the formula A-(OH)m in the presence of a tin catalyst; wherein the improvement comprises reacting the tin catalyzed transesterification reaction mass with a carboxylic acid or hydrate thereof neat, in the absence of an aqueous medium, until the tin catalyst forms an insoluble derivative, and then separating the insoluble derivative from the reaction mass by filtration without the assistance of a filtration aid. The invention allows for a convenient method by which to remove the residual tin catalyst from the substituted hydroxyphenylcarboxylic acid ester compounds of formula (I).
    Type: Grant
    Filed: January 28, 1999
    Date of Patent: February 6, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: John Richard Ross
  • Patent number: 6150408
    Abstract: Compounds that are isolatable from cherries and have antioxidant activity, and methods for isolating these compounds are described. In particular, the invention relates to 1-(3',4'-dihydroxycinnamoyl)-cyclopenta-2,3-diol and 1-(3',4'-dihydroxycinnamoyl)-cyclopenta-2,5-diol, which have antioxidant activity. These antioxidant compounds and compositions containing these compounds are useful as food preservatives, dietary supplements, nutraceuticals, and phytoceuticals.
    Type: Grant
    Filed: June 10, 1999
    Date of Patent: November 21, 2000
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Muraleedharan G. Nair, Haibo Wang, Gale M. Strasburg, Alden M. Booren, James I. Gray
  • Patent number: 6136852
    Abstract: The present invention relates to 3,4-disubstituted phenylethanolaminotetralincarboxylic acid derivatives represented by the general formula: ##STR1## [wherein Q represents a vinylene group or a group represented by the general formula:-A-(CH.sub.2).sub.m --(wherein A represents an oxygen atom or a methylene group; and m is an integer of from 1 to 6); R represents a hydrogen atom or a lower alkyl group; n is an integer of 1 or 2; the carbon atom marked with * represents a carbon atom in R configuration, S configuration or a mixture thereof; and the carbon atom marked with (S) represents a carbon atom in S configuration] and pharmaceutically acceptable salts thereof, which have a selective .beta..sub.2 -adrenergic receptor stimulating effect with relieved burdens on the heart such as tachycardia and are useful as an agent for the prevention of threatened abortion and premature labor, a bronchodilator and an agent for pain remission and promoting stone removal in urolithiasis.
    Type: Grant
    Filed: March 8, 1999
    Date of Patent: October 24, 2000
    Assignee: Kissei Pharmaceutical Co., Ltd.
    Inventors: Makio Kitazawa, Kosuke Okazaki, Tetsuro Tamai, Masaru Saito, Nobuyuki Tanaka, Hiroaki Kobayashi, Ken Kikuchi, Hideyuki Muranaka
  • Patent number: 6066311
    Abstract: There is disclosed a novel method of producing caffeic acid in large quantities, comprising the esterification of chlorogenic acid with an esterifying enzyme. Caffeic acid and its derivatives, produced by this method, may be used in sunscreen compositions, the caffeic acid and its derivatives absorbing both uvA and uvB light.
    Type: Grant
    Filed: March 14, 1997
    Date of Patent: May 23, 2000
    Assignee: Zylepsis Limited
    Inventors: Peter S. J. Cheetham, Nigel E. Banister
  • Patent number: 5981583
    Abstract: The present invention is drawn to the inhibition of activation of NF-.kappa.B by caffeic acid phenethyl ester (CAPE) and two analogues of CAPE. Tumor necrosis factor (TNF) activation of NF-.kappa.B is completely blocked by CAPE in a dose- and time-dependent manner, as is activation by phorbol ester, ceramide, hydrogen peroxide, and okadaic acid. Additionally, capsaicin (8-methyl-N-vanillyl-6-noneamide) and resiniferatoxin inhibit the activation of NF-.kappa.B induced by different agents.
    Type: Grant
    Filed: September 5, 1997
    Date of Patent: November 9, 1999
    Assignee: Research Development Foundation
    Inventors: Bharat B. Aggarwal, Dezider Grunberger
  • Patent number: 5973072
    Abstract: The present invention is directed to a polymeric vehicle, the formulated coating composition and a coating binder made from the polymeric vehicle and a method for making the polymeric vehicle where the polymeric vehicle includes a phenolic urethane reactive diluent. The phenolic urethane reactive diluent may be made from a phenolic ester alcohol having at least one aliphatic hydroxyl group.
    Type: Grant
    Filed: March 21, 1996
    Date of Patent: October 26, 1999
    Assignee: Exxon Chemical Patents, Inc.
    Inventors: Frank N. Jones, Vijay Swarup, Ramachandran P. Subrayan, Suru Zhang
  • Patent number: 5948922
    Abstract: Compounds containing two cyclic hydrocarbon moieties which are substituted to provide crosslinking functionality and which are linked to each other by secondary or tertiary oxycarbonyl containing moiety are basis for compositions which are cured to provide cured thermosets for encapsulation and underfill for electronic components that are thermally decomposable to allow repair, replacement, recovery or recycling of operative electronic components from assemblies that are inoperative.
    Type: Grant
    Filed: February 20, 1997
    Date of Patent: September 7, 1999
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Hilmar Koerner
  • Patent number: 5945448
    Abstract: The present invention relates to a composition for treating or preventing brain edemas which comprises containing an endothelin antagonist as an active ingredient, for example, the compound of the following formula (I): ##STR1## or pharmaceutically acceptable salts or hydrates thereof, bosentan, cyclo?D-aspartyl-L-?3-(4-phenylpiperazin-1-ylcarbonyl)!-alanyl-L-aspartyl- D-?2-(2-thienyl)!glycyl-L-leucyl-D-tryptophyl!disodium or cyclo ?D-Asp-L-Pro-D-Val-L-Leu-D-Trp!.Furthermore, the present invention provides a method for treating or preventing brain edemas, which comprises administering an effective amount of an endothelin antagonist and use of an endothelin antagonist for the manufacture of a medicament for treating or preventing brain edemas.An endothelin antagonist exhibits an inhibitory effect, on all brain edemas regardless of the onset mechanism and thus is highly useful in the treatment or prevention of brain edemas.
    Type: Grant
    Filed: October 10, 1997
    Date of Patent: August 31, 1999
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuyoshi Ninomiya, Yoshiyuki Matsuo
  • Patent number: 5892097
    Abstract: The transesterification of substituted lower alkyl hydroxyhydrocinnamates with a higher alcohol or a polyol is greatly facilitated by the use of a trace amount of a tin catalyst. In many cases, the amount of the catalyst is so small that it is unnecessary to remove it from the final product by distillation of said product.
    Type: Grant
    Filed: May 22, 1997
    Date of Patent: April 6, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: John R. Ross, Michael E. Schultz, Benoit Dubuis, Peter Kung
  • Patent number: 5739377
    Abstract: Compounds of formula (I): ##STR1## wherein: R.sup.1 represents an alkyl group having from 1 to 6 carbon atoms;R.sup.2 represents an alkyl group having from 8 to 24 carbon atoms;EO represents an ethyleneoxy group;PO represents a propyleneoxy group;k is 0 or an integer from 1 to 10; andm is an integer from 1 to 4;provided that the total of (k+m) is greater than 1 and not greater than 10;are useful as antioxidant stabilizers for polymeric materials.
    Type: Grant
    Filed: April 7, 1995
    Date of Patent: April 14, 1998
    Assignee: Sankyo Company, Limited
    Inventors: Hisayu Ohsawa, Tomoyuki Kurumada, Takaaki Yamazaki, Satoru Naito, Kohtaro Kanetaki
  • Patent number: 5721103
    Abstract: Novel trienoic compounds having activity for retinoic acid receptors and retinoid X receptors are provided. Also provided are pharmaceutical compositions incorporating such compounds and methods for their use.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 24, 1998
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventors: Marcus F. Boehm, Lin Zhang, Youssef L. Bennani, Alex M. Nadzan
  • Patent number: 5713966
    Abstract: Polyalkyl hydroxyaromatic esters having the formula: ##STR1## or a fuel-soluble salt thereof; where R.sub.1 and R.sub.2 are independently hydrogen, hydroxy, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; R.sub.3 is a polyalkyl group having a weight average molecular weight in the range of about 450 to 5,000; and x is an integer from 0 to 10.The polyalkyl hydroxyaromatic esters of formula I are useful as fuel additives for the prevention and control of engine deposits.
    Type: Grant
    Filed: April 16, 1996
    Date of Patent: February 3, 1998
    Assignee: Chevron Chemical Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5696281
    Abstract: The present invention relates to novel liquid phenolic antioxidants, to organic materials stabilized with said compounds against thermal, oxidalive and/or actinic degradation, and to the use of said novel compounds as stabilizers.
    Type: Grant
    Filed: June 20, 1995
    Date of Patent: December 9, 1997
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Samuel Evans
  • Patent number: 5686633
    Abstract: Inks, particularly inks for ink jet printing, contain at least one compound of the formula I ##STR1## as a stabilizer. The symbols R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.3 ' and R.sub.4 ' are as defined in claim 1. The compounds are in part novel and are suitable for use as light stabilizers for organic materials.
    Type: Grant
    Filed: December 31, 1991
    Date of Patent: November 11, 1997
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Eric Vieira, Hugh Stephen Laver
  • Patent number: 5659067
    Abstract: A description is given of a process for the preparation of 2,5-bis(1,1-dimethyl-4-hexyloxycarbonylbutyl)hydroquinone by reacting 5-methyl-4-hexenoic acid (m)ethyl ester, which is obtainable by reacting 2-hydroxy-2-methyl-3-butene with tri(m)ethyl orthoacetate in the presence of an acid catalyst, with hydroquinone according to Friedel-Crafts, and transesterifying the resulting 2,5-bis(1,1-dimethyl-4-(m)ethoxycarbonylbutyl)-hydroquinone product direct with hexanol in a one-pot process.
    Type: Grant
    Filed: September 12, 1996
    Date of Patent: August 19, 1997
    Assignee: Ciba-Geigy Corporation
    Inventor: Reinhard Sommerlade
  • Patent number: 5654338
    Abstract: Optically active .alpha.-(hydroxyphenoxy)-alkanecarboxylic acids or derivatives thereof, for example D-2-(4-hydroxyphenoxy)propionic acid or lower alkyl ester thereof, are prepared by (a) saponifying an alkyl ester of an optically active .alpha.-halogeno-alkanecarboxylic acid, in an alcoholic solvent medium, by reacting same with an aqueous solution of an alkali metal hydroxide, thereby providing a solution of an alkali metal salt of an optically active .alpha.-halogeno-alkanecarboxylic acid, (b) next reacting the step (a) solution thus provided with a dihydroxybenzene or salt thereof, in the presence of an alkali metal hydroxide and in an alcoholic solvent medium, and thence (c) recovering the optically active .alpha.-(hydroxyphenoxy)-alkanecarboxylic acid or derivative thereof from the medium of reaction.
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: August 5, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventor: Pascal Metivier
  • Patent number: 5637756
    Abstract: A cosmetic or dermatological composition with a depigmenting action comprises derivatives of 2,5-dihydroxyphenylcarboxylic acids, their homologs, and their salts, with the derivatives having the following structural formula: ##STR1## wherein: R.sub.1 represents OR.sub.5, OH, or ##STR2## R.sub.5 is a linear or branched C.sub.1 -C.sub.20 alkyl radical, a linear or branched C.sub.2 -C.sub.20 alkenyl radical, or a C.sub.1 -C.sub.20 alkyl radical substituted by one or more hydroxy or alkoxy groups; r' and r", identical or different, represent a hydrogen atom, a C.sub.1 -C.sub.20 alkyl radical, a C.sub.2 -C.sub.6 hydroxyalkyl radical, or a C.sub.3 -C.sub.6 polyhydroxyalkyl, or r' and r" taken together, with the nitrogen atom, form a heterocycle;the number of carbon atoms in the --(CH.sub.2).sub.n --COR.sub.1 chain is less than or equal to 21;R.sub.2 and R.sub.3, identical or different, represent a hydrogen atom, a linear or branched C.sub.1 -C.sub.4 alkyl radical, or a C.sub.1 -C.sub.4 alkoxy; R.sub.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: June 10, 1997
    Assignee: L'Oreal
    Inventors: Alex Junino, Alain Lagrange, Quang L. N'Guyen, Marie-Alix Bourboulon
  • Patent number: 5629422
    Abstract: New compounds of the formula I are described which are active, for example, as antioxidants, and also a process for their preparation: ##STR1## R.sub.1 and R.sub.2 are independently of one another C.sub.1 -C.sub.20 alkyl, allyl, methallyl, unsubstituted or C.sub.1 -C.sub.8 alkyl-substituted C.sub.5 -C.sub.12 cycloalkyl, C.sub.5 -C.sub.8 cycloalkenyl, phenyl or C.sub.7 -C.sub.9 phenylalkyl, A is a direct bond, --CH.sub.2 --, --(CH.sub.2).sub.2 -- or --CH.sub.2 --CH(CH.sub.3)--, E is --(CH.sub.2).sub.2 --, --CHR.sub.6 --CH.sub.2 -- or --CH.sub.2 CHR.sub.6 --, n is 1, 2 or 3, R.sub.3 is C.sub.1 -C.sub.18 alkyl or is C.sub.1 -C.sub.18 alkyl which is interrupted by --O-- or --S--, unsubstituted or C.sub.1 -C.sub.8 alkyl-substituted C.sub.5 -C.sub.12 cycloalkyl, phenyl, naphthyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.7 -C.sub.18 alkylphenyl or is of the formula ##STR2## R.sub.4 is phenyl, naphthyl, C.sub.7 -C.sub.9 phenylalkyl, C.sub.7 -C.sub.18 alkylphenyl or is a radical of the formula ##STR3## or NR.sub.3 R.sub.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: May 13, 1997
    Assignee: Ciba Geigy Corporation
    Inventor: Hugo Camenzind
  • Patent number: 5563291
    Abstract: There is disclosed a process for the preparation of compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other C.sub.1 -C.sub.8 alkyl or cyclopentyl or cyclohexyl,m is 0, 1, 2 or 3,n is 1 or 2, andR.sub.3, depending on the value of n, is C.sub.4 -C.sub.20 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.2 -C.sub.4 alkylene, or C.sub.4 -C.sub.12 alkylene which is interrupted by oxygen,by reaction of a compound of formula II ##STR2## wherein R is methyl or ethyl, with a compound of formula IIIR.sub.3 (OH).sub.n (III)which reaction is carried out in the presence of magnesium acetate as catalyst.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: October 8, 1996
    Assignee: Ciba-Geigy Corporation
    Inventor: Christoph Kleiner
  • Patent number: 5536874
    Abstract: There is provided a process for preparing an arylacetic acid or arylpropionic acid divative from an arylcarbinol which comprises the step of subjecting said arylcarbinol to suitable carbonylation conditions for a sufficient period of time and under suitable pressure and temperature to form said acid derivative, with the proviso that said carbonylation conditions include conducting the reaction in a two-phase system wherein one phase is an aqueous medium which contains (1) a catalyst which is a water-soluble metal complex consisting essentially of a Group VIII metal and a hydrophilic ligand such as palladium complexed with trisulfonated triphenylphosphine, and (2) optionally an acid, and wherein the second phase comprises said arylcarbinol.
    Type: Grant
    Filed: November 30, 1994
    Date of Patent: July 16, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: Roger A. Sheldon, Leendert Maat, Georgios Papadogianakis
  • Patent number: 5498795
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 -R.sub.3 and R.sub.5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R.sub.4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; X is S or O; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl, said groups being substituted with the R.sub.5 group defined above; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: March 12, 1996
    Assignee: Allergan, Inc.
    Inventors: Tae K. Song, Roshantha A. Chandraratna
  • Patent number: 5481023
    Abstract: There is disclosed a process for the preparation of compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other C.sub.1 --C.sub.8 alkyl, m is 0, 1, 2 or 3, n is 1 or 2, and A, if n 32 1, is OR.sub.3, and R.sub.3 is C.sub.4 -C.sub.20 alkyl or C.sub.5 -C.sub.12 cycloalkyl, or A, if n=2, has the formula --O--C.sub.x H.sub.2x --O-- or --O--(CH.sub.2 CH.sub.2 O).sub.a CH.sub.2 CH.sub.2 O--, x is a number from 2 to 8 and a is a number from 1 to 12, by reacting a compound of formula II ##STR2## with a compound of formula III ##STR3## the reaction being carded out in the presence of an aluminium trialcoholate or triphenolate as catalyst.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: January 2, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Christoph Kleiner, Samuel Evans, Ralf Schmitt
  • Patent number: 5457226
    Abstract: A novel process for the manufacture of a cinnamic acid derivative of the formula ##STR1## wherein R.sup.1 signifies hydrogen or C.sub.1-8 -alkyl and R.sup.2 signifies hydrogen, C.sub.1-10 -alkyl, C.sub.1-10 -hydroxyalkyl or C.sub.1-4 -alkoxy-C.sub.1-10 -alkyl, is described in which a 4-R.sup.1 O-halobenzene is reacted with acrylic add or an acrylic acid ester CH.sub.2 .dbd.CHCOOR.sup.2 using a heterogeneous palladium catalyst in the presence of the alkanoic acid ammonium salt formed from a C.sub.2-5 -alkanoic acid and an aliphatic mono-, di- or trialkylamine or heterocyclic amine. In the case of the manufacture of the cinnamic acid derivative I in which R.sup.2 signifies hydrogen, the reaction can be carried out in the presence of the amine in place of the alkanoic acid ammonium salt. A further aspect of the described invention comprises reacting the 4-R.sup.1 O-iodobenzene with the product of the Michael addition of an acrylic acid ester CH.sub.2 .dbd.CHCOOR.sup.2', wherein R.sup.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: October 10, 1995
    Assignee: Givaudan-Roure Corporation
    Inventor: Peter Gygax
  • Patent number: 5449518
    Abstract: A cosmetic or dermatological composition with a depigmenting action comprises derivatives of 2,5-dihydroxyphenylcarboxylic acids, their homologs, and their salts, with the derivatives having the following structural formula: ##STR1## wherein: R.sub.1 represents OR.sub.5, or ##STR2## R.sub.5 is a hydrogen atom, a linear or branched C.sub.1 -C.sub.20 alkyl radical, a linear or branched C.sub.2 -C.sub.20 alkenyl radical, or a C.sub.1 -C.sub.20 alkyl radical substituted by one or more hydroxy or alkoxy groups; r' and r", identical or different, represent a hydrogen atom, a C.sub.1 -C.sub.20 alkyl radical, a C.sub.2 -C.sub.6 hydroxyalkyl radical, or a C.sub.3 -C.sub.6 polyhydroxyalkyl, or r' and r" taken together, with the nitrogen atom, form a heterocycle; the number of carbon atoms in the --(CH.sub.2).sub.n --COR.sub.1 chain is less than or equal to 21;R.sub.2 and R.sub.3, identical or different, represent a hydrogen atom, a linear or branched C.sub.1 -C.sub.4 alkyl radical, or a C.sub.1 -C.sub.4 alkoxy; R.sub.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: September 12, 1995
    Assignee: L'Oreal
    Inventors: Alex Junino, Alain Lagrange, Quang L. N'Guyen, Marie-Alix Bourboulon
  • Patent number: 5434302
    Abstract: The present process is directed to preparing optically active 2-aryl alkyl aldehydes by various processes through the use of an optically active amine, (-)-2'-amino-3-phenyl propane. The aldehyde formed can then be oxidized to produce the corresponding acid.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: July 18, 1995
    Inventor: H. Henrich Paradies
  • Patent number: 5414108
    Abstract: The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula ##STR1## wherein R means hydrogen, or a C.sub.1-4 alkyl or a (C.sub.1-5 alkoxy)carbonyl group,R.sub.1 is as defined in claim 1,R.sub.7 stands for hydrogen or a C.sub.1-7 alkyl group andR.sub.8 means hydrogen or a carboxyl group.
    Type: Grant
    Filed: August 11, 1992
    Date of Patent: May 9, 1995
    Assignee: Biogal Gyogyszergrar
    Inventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
  • Patent number: 5319127
    Abstract: Disclosed are a class of phenolic-hydrazide compounds of diverse structure which are useful as stabilizers for polyolefins. The phenolic-hydrazide compounds inhibit oxidative degradation of polyolefins which is attributable to heat and/or ultraviolet light and is promoted or accelerated by metals, e.g., copper, in contact with the polyolefin.
    Type: Grant
    Filed: September 23, 1993
    Date of Patent: June 7, 1994
    Assignee: Eastman Chemical Company
    Inventors: Richard H. S. Wang, Ping P. Shang, Daniel A. Jervis
  • Patent number: 5310773
    Abstract: Perfluoroalkyl substituted neopentyl alcohols can be reacted with substituted hydroxphenylalkanoic esters to form perfluoroalkyl containing hydroxyphenylalkanoic ester antioxidants. The perfluoroalkyl substituted hindered hydroxyphenyl alkanoates are stablizers which confer superior processing stability to polymers processed at elevated temperatures such as polypropylene, as well as protecting said polymers from thermal and oxidative degradation.
    Type: Grant
    Filed: June 4, 1992
    Date of Patent: May 10, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert A. Falk, Eduard K. Kleiner
  • Patent number: 5302744
    Abstract: Disclosed are a class of phenolic-hydrazide compounds of diverse structure which are useful as stabilizers for polyolefins. The phenolic-hydrazide compounds inhibit oxidative degradation of polyolefins which is attributable to heat and/or ultraviolet light and is promoted or accelerated by metals, e.g., copper, in contact with the polyolefin.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: April 12, 1994
    Assignee: Eastman Kodak Company
    Inventors: Richard H. S. Wang, Ping P. Shang, Daniel A. Jervis
  • Patent number: 5290937
    Abstract: Novel compounds, useful as radiolabeling reagents, including an alkoxy group on the phenyl ring and having the formula ##STR1## wherein X is a radionuclide are disclosed. The invention further includes novel radiohalogenated proteins as well as processes for preparing such reagents and radiohalogenated proteins.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: March 1, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Frank P. Tomasella
  • Patent number: 5283352
    Abstract: Catechol compounds of formula I ##STR1## where R.sub.1, R.sub.2, R.sub.3 and X are as described herein are effective Catechol-O-methyltransferase inhibitors.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: February 1, 1994
    Assignee: Orion-yhtyma Oy
    Inventors: Reijo J. Backstrom, Kalevi E. Heinola, Erkki J. Honkanen, Seppo K. Kaakkola, Pekka J. Kairisalo, Inge-Britt Y. Linden, Pekka I. Mannisto, Erkki A. O. Nissinen, Pentti Pohto, Aino K. Pippuri, Jarmo J. Pystynen