Sulfur, Not Bonded Directly To A Ring, In Same Side Chain As Ester Function Patents (Class 560/15)
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Patent number: 6201020Abstract: This invention relates to compounds, pharmaceutical compositions, and methods of using compounds of the formula: A is O or S; R is C1-C10 straight or branched chain alkyl, C2-C10 straight or branched chain alkenyl, C2-C10 straight or branched chain alkynyl, aryl, heteroaryl, carbocycle, or heterocycle; D is a bond, or a C1-C3 straight or branched chain alkyl, C2-C3 straight or branched chain alkenyl, C2-C3 straight or branched chain alkynyl, wherein any of the carbon atoms of said alkyl, alkenyl, or alkynyl of D are optionally replaced with oxygen, nitrogen, or sulfur; and X is aryl, heteroaryl, carbocycle, or heterocycle.Type: GrantFiled: December 31, 1998Date of Patent: March 13, 2001Assignee: Guilford Pharmaceuticals, Inc.Inventors: Jie Zhang, Larisa E. Serdyuk, Jia-He Li
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Patent number: 6054457Abstract: This invention relates to new benzamide derivatives having a vasopressin antagonistic activity, etc, and represented by general formula (I): ##STR1## wherein R.sup.1 is aryl optionally substituted with lower alkoxy, etc., R.sup.2 is lower alkyl, etc.,R.sup.3 is hydrogen, etc.,R.sup.4 is lower alkoxy, etc.,R.sup.5 is hydrogen, etc.,A is NH, etc.,E is ##STR2## etc., X is --CH.dbd.CH--, --CH.dbd.N--, or S, andY is CH or N,and pharmaceutically acceptable salts thereof, to processes for preparation thereof and to a pharmaceutical composition comprising the same.Type: GrantFiled: December 9, 1997Date of Patent: April 25, 2000Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Hiroyuki Setoi, Takehiko Ohkawa, Tatsuya Zenkoh, Hitoshi Sawada, Kentaro Sato, Hirokazu Tanaka
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Patent number: 6043275Abstract: A 3,7-dithiaprostanoic acid derivative of the formula (I) ##STR1## (wherein, R.sup.1 is OH, C1.about.6 alkyloxy, NR.sup.6 R.sup.7 (R.sup.6, R.sup.7 are H, C1.about.6 alkyl.); R.sup.2 is H, OH; R.sup.3 is single bond, C1.about.6 alkylene; R.sup.4 is (i) C1.about.8 alkyl substituted by C1.about.6 alkyloxy, halogen etc., (ii) phenyloxy, C3.about.7 cycloalkyloxy, (iii) furyl, furyloxy, thienyl, thienyloxy, naphthyl, naphthyloxy, phthalanyl, phthalanyloxy, (iv) phenyl, phenyloxy, C3.about.7 cycloalkyl, C3.about.7 cycloalkyloxy substituted by C1.about.6 alkyl etc., (v) furyl, furyloxy, thienyl, thienyloxy, naphthyl, naphthyloxy, phthalanyl, phthalanyloxy substituted by C1.about.6 alkyl etc.; R.sup.5 is H, C1.about.6 alkyl.) can bind PGE.sub.2 receptor (particularly, EP4 subtype receptor) strongly. So, they are useful for the prevention and/or treatment of immunological diseases (autoimmune diseases, rejection after organ transplantation etc.Type: GrantFiled: April 8, 1999Date of Patent: March 28, 2000Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Toru Maruyama, Shuichi Ohuchida
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Patent number: 6028131Abstract: The invention relates to compounds of the formula I ##STR1## in which R is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.7 -C.sub.9 phenylalkyl, --CH.sub.2 --A--R.sub.2 or a group of the formula II, ##STR2## R.sub.1 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.7 -C.sub.9 phenylalkyl or a group of the formula (II),R.sub.2 is C.sub.4 -C.sub.18 alkyl, --(CH.sub.2).sub.m --COOR.sub.5 or a group of the formula III, ##STR3## R.sub.3 is hydrogen, C.sub.5 -C.sub.8 cycloalkyl or C.sub.1 -C.sub.12 alkyl,R.sub.4 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.7 -C.sub.9 phenylalkyl or a group of the formula II or IV, ##STR4## A is S or SO, E is a direct bond, --CH.sub.2 --, --CH.sub.2 --O-- or --CH.sub.2 --NH--,G is --O-- or --NR.sub.3 --,Y is C.sub.1 -C.sub.18 alkyl, cyclohexyl, phenyl or alpha- or beta-naphthyl,R.sub.5 is C.sub.1 -C.sub.18 alkyl, andm is 1 or 2,with the provisos thateither at least one of the radicals R and R.sub.Type: GrantFiled: April 27, 1998Date of Patent: February 22, 2000Assignee: Ciba Specialty Chemicals CorporationInventors: Hans-Rudolf Meier, Gerrit Knobloch
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Patent number: 5981556Abstract: 1,3-diazolino and 1,3-diazolidino heterocycle derivatives useful as nitric oxide synthase inhibitors.Type: GrantFiled: July 22, 1997Date of Patent: November 9, 1999Assignee: G.D. Searle & Co.Inventors: Donald W. Hansen, Jr., Arija A. Bergmanis, Timothy J. Hagen, E. Ann Hallinan, Steven W. Kramer, Suzanne Metz, Karen B. Peterson, Barnett S. Pitzele, Foe S. Tjoeng, Mihaly V. Toth, Mahima Trivedi, R. Keith Webber, Sofya Tsymbalov, Rolando E. Gapud
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Patent number: 5977123Abstract: The invention relates to novel oximether and acrylic acid derivatives of the formula (I) ##STR1## in which Z, G, Ar, E, R.sup.1 and R.sup.2 have the meanings as given in the specification, to processes for their preparation and to their use as fungicides.Type: GrantFiled: January 9, 1998Date of Patent: November 2, 1999Assignee: Bayer AktiengesellscgaftInventors: Peter Gerdes, Herbert Gayer, Ulrich Heinemann, Ralf Tiemann, Klaus Stenzel, Stefan Dutzmann
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Patent number: 5952386Abstract: The present invention provides dihalopropene compounds of the general formula: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl or the like; L is C(.dbd.O)NH or the like; R.sub.2, R.sub.3 and R.sub.4 are independently halogen or the like; R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen or the like; m is an integer of 0 to 4; n is an integer of 0 to 2; X is chlorine or the like; Y is oxygen or the like; and Z is oxygen or the like, which have excellent insecticidal activity so that they are satisfactorily effective for the control of noxious insects.Type: GrantFiled: September 24, 1997Date of Patent: September 14, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Sanshiro Matsuo, Taro Hirose, Keiichi Izumi, Masaya Suzuki, Noriyasu Sakamoto, Kazunori Tsushima, Shigeru Saito, Hirotaka Takano
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Patent number: 5892099Abstract: A 3,7-dithiaprostanoic acid derivative of the formula (I) ##STR1## (wherein R.sup.1 is OH, C1-4 alkoxy, NR.sup.6 R.sup.7 (wherein R.sup.6, R.sup.7 are H, C1-4);R.sup.2 is H, OH; R.sup.3 is (i)alkyl, alkenyl, alkynyl (ii) phenyl, cycloalkyl (iii) alkyl, alkenyl, alkynyl substituted by phenyl, cycloalkyl (when R.sup.2 is H, alkyl, alkenyl, alkynyl in (i) or (iii) may be substituted by OH) possesses a binding activity for PGE.sub.2 receptor (especially for EP4). Therefore they are useful for the treatment and/or prevention of immunologic diseases (autoimmune diseases, immunological deficiency diseases, organ transplantation etc.), asthma, abnormal bone formation, neuronal cell death, liver damage, nephritis, hypertension, myocardiac ischemia etc.Type: GrantFiled: January 27, 1998Date of Patent: April 6, 1999Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Toru Maruyama, Shuichi Ohuchida
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Patent number: 5872282Abstract: A family of compounds has been found to be useful for right-shifting hemoglobin towards a low oxygen affinity state. The compounds are capable of acting on hemoglobin in whole blood. In addition, the compounds can maintain the oxygen affinity in blood during storage and can restore the oxygen affinity of outdated blood.Type: GrantFiled: March 13, 1998Date of Patent: February 16, 1999Assignee: Virginia Commonwealth UniversityInventors: Donald J. Abraham, Gajanan Joshi, Ramnarayan Randad
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Patent number: 5756838Abstract: The present invention relates to water soluble chiral sulfonated 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl and its use as organometallic catalysts for asymmetric synthesis of optically active compounds. Asymmetric reactions of the present invention include those reactions in which organometallic catalysts are commonly used. Such reactions include, but are not limited to, reduction and isomerization reactions on unsaturated substrates and carbon--carbon bond forming reactions. Examples of such reactions include, but are not limited to, hydrogenation, hydroboration, hydrosilylation, hydride reduction, hydroformylation, alkylation, allylic alkylation, arylation, alkenylation, epoxidation, hydrocyanation, disilylation, cyclization and isomerization reactions.The catalysts of the present invention provide the advantage of functioning in the presence of water without loss in enantioselectivity relative to the nonsulfonated BINAP catalyst in an organic solvent.Type: GrantFiled: August 16, 1995Date of Patent: May 26, 1998Assignee: California Institute of TechnologyInventors: Mark E. Davis, Kam To Wan
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Patent number: 5693848Abstract: .alpha.,.omega.-polymethacrylate dicarboxylic acids of the general formula ##STR1## wherein R.sup.1 is an optionally halogenated alkyl group with 1 to 22 carbon atoms, wherein the R1 group can assume different meanings in the polymer molecule,R.sup.2 is the group of a known chain transfer agent, which has a terminal --COOH croup anda has a value not less than 4. The invention furthermore relates to the synthesis of these compounds and their use as sole or partial components for the synthesis or modification of polyepoxides, polyesters, polyamides, alkyd resins or polyurethanes.Type: GrantFiled: October 18, 1995Date of Patent: December 2, 1997Assignee: Th. Goldschmidt AGInventors: Eberhard Esselborn, Jurgen Fock
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Patent number: 5686633Abstract: 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: GrantFiled: December 31, 1991Date of Patent: November 11, 1997Assignee: Ciba Specialty Chemicals CorporationInventors: Eric Vieira, Hugh Stephen Laver
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Patent number: 5663128Abstract: Products are described which can be obtained by reacting components a), b), c) and d), where component a) is a compound of the formula I or a mixture of compounds of the formula I, component b) is a compound of the formula II or a mixture of compounds of the formula II, component c) is a compound of the formula III or a mixture of compounds of the formula III and component d) is a compound of the formula IV or a mixture of compounds of the formula IV, ##STR1## in which the general symbols are as defined in claim 1, the compound of the formula I being, for example, pentaerythritol, thiodiethylene glycol, 1,4-butanediol, 1,2-propanediol, diethylene glycol, triethylene glycol, diethanolamine or glycerol, the compound of the formula II being, for example, sunflower oil or coconut fat, the compound of the formula III being, for example, methyl 3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate and the compound of the formula IV, being for example, sulfur or diisopropyl dithiophosphate.Type: GrantFiled: September 19, 1994Date of Patent: September 2, 1997Assignee: Ciba-Geigy CorporationInventors: Samuel Evans, Paul Dubs, Hugo Camenzind
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Patent number: 5639903Abstract: The present invention is related to sulfonium salt compounds useful as an initiator of cationic polymerization and represented by a following general formula (I): ##STR1## wherein R.sub.1 is benzyl, phenyl, etc., R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, alkyl, etc., R.sub.5 is hydrogen, alkyl, phenyl, etc., R.sub.6 is a group represented by a formula, --(CH.sub.2).sub.m --R.sub.11 wherein R.sub.11 is COR.sub.12, COOR.sub.13, OR,.sub.14, nitrile, OCOR.sub.15 or SOR.sub.16, wherein R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are each independently hydrogen, alkyl or phenyl, m is 0 or 1, and X represents SbF.sub.6, AsF.sub.6, PF.sub.6 or BF.sub.4.Type: GrantFiled: December 11, 1995Date of Patent: June 17, 1997Assignee: Nippon Soda Co., Ltd.Inventors: Eiji Takahashi, Hiroo Muramoto
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Patent number: 5625067Abstract: The invention relates to cyclopentane ether derivatives of Formula I ##STR1## their salts with physiologically compatible bases, as well as the .alpha.-, .beta.- or .gamma.-cyclodextrin clathrates, and also the liposome-encapsulated compounds of Formula I, processes for their production, and their pharmaceutical usage.Type: GrantFiled: December 14, 1994Date of Patent: April 29, 1997Assignee: Schering AktiengesellschaftInventors: Hartmut Rehwinkel, Ulrich Klar, Helmut Vorbruggen, Karl-Heinz Thierauch, Peter Verhallen
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Patent number: 5536870Abstract: A process for preparing olefin compounds of the formula ##STR1## where A is aryl, substituted aryl, heteroaryl, substituted heteroaryl, benzyl, substituted benzyl, vinyl or substituted vinyl and R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkyl, cycloalkyl, alkyl-substituted cycloalkyl, aryl, substituted aryl, alkoxy, alkythio, heteroaryl, substituted heteroaryl, alkanoyl, aroyl, substituted aroyl, heteroarylcarbonyl, substituted heteroarylcarbonyl, trifluoromethyl or halo, which comprises reacting an organic halide of the formula A-X where X is chloro, bromo or iodo with a vinyl or substituted vinyl compound of the formula ##STR2## where R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: February 17, 1995Date of Patent: July 16, 1996Assignee: Albemarle CorporationInventor: Tse-Chong Wu
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Patent number: 5534651Abstract: .gamma.-Mercaptocarboxylic acids and their derivatives, in particular esters and amides, are prepared from .gamma.-butyrolactones via the corresponding thiolactones. The thiolactones are obtained by reaction of a .gamma.-lactone with thiocarboxylates in polar solvents and are converted by ring opening using nucleophilic reagents, such as, alkali metal alkoxides, into the .gamma.-mercaptocarboxylic acid derivatives. These are intermediates, for example, for the synthesis of leucotriene antagonists.Type: GrantFiled: August 30, 1994Date of Patent: July 9, 1996Assignee: Lonza Ltd.Inventors: Wilhelm Quittmann, John McGarrity
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Patent number: 5508275Abstract: Lipid-selective antioxidants of the formula I(A).sub.a (L)(X).sub.a, (I),in whichA=an antioxidative component,L=a bridging member,X=a lipophilic componenta and a'=independently of one another the numbers 1 or 2.The compounds are used for the protection of lipid-containing substances against oxidation and in pharmaceuticals for the prophylaxis and treatment of diseases in which bioradicals are involved, in particular of coronary, circulatory and vascular diseases.Type: GrantFiled: March 15, 1994Date of Patent: April 16, 1996Assignee: Hoechst AktiengesellschaftInventors: Klaus-Ulrich Weithmann, Gunther Wess, Dirk Seiffge
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Patent number: 5502246Abstract: A method for photochemical cleavage of carbon-sulfur bonds in conjunction with solid-phase synthesis utilizing a deoxygenated solvent and light to cleave the carbon-sulfur bond from a heterogeneous support. Also disclosed are compounds for use with said photochemical cleavage and methods of preparing them.Type: GrantFiled: March 22, 1994Date of Patent: March 26, 1996Assignee: Eli Lilly and CompanyInventor: Irving Sucholeiki
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Patent number: 5453443Abstract: Compounds having the formula I: ##STR1## are inhibitors of the PLA.sub.2 s enzymes. These compounds are useful as anti-allergic, anti-asthmatic, they are also useful in treating various inflammatory diseases such as rheumatoid arthritis, osteoarthritis, bursitis, psoriasis; immunoinflammatory disorders such as contact dermatitis, irritable bowel disease and the like.Type: GrantFiled: July 20, 1994Date of Patent: September 26, 1995Assignee: Merck Frosst Canada, Inc.Inventors: Helene Perrier, Petpiboon Prasit, Ian Street, Zhaoyin Wang
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Patent number: 5434288Abstract: PLA.sub.2 inhibitors selected from the group consisting of ##STR1## wherein A is selected from the group consisting of ##STR2## and Z, W, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, X, X' and Y are as defined herein.Type: GrantFiled: June 14, 1994Date of Patent: July 18, 1995Assignee: Monsanto CompanyInventor: Patrick J. Lennon
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Patent number: 5428140Abstract: Reactive dyes of the formula ##STR1## where n is 0 or 1R.sup.1, R.sup.2 and R.sup.3 are in each case hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.4 is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl or a radical of the formula ##STR2## L is a bridge member, A is unsubstitued or substituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, Q being a group which can be removed under alkaline reaction conditions, andD is phenyl or naphthyl, it being possible for these radicals to be substituted,and a process for preparing reactive dyes by oxidation of the abovementioned compounds are described.Type: GrantFiled: June 6, 1994Date of Patent: June 27, 1995Assignee: BASF AktiengesellschaftInventors: Matthias Wiesenfeldt, Bernd Siegel, Manfred Patsch
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Patent number: 5403953Abstract: Compound of formula (I): ##STR1## in which: R.sub.1 represents halogen, or hydroxy, alkyl, alkoxy, cyano, amino, mercapto, alkylthio or phenoxy,R.sub.2 and R'.sub.2 represent two hydrogen when the ring is unsaturated, or alternatively identical or different, represent hydrogen or halogen, or hydroxy, alkyl, alkoxy, cyano, amino or oxo when the ring is saturated,R.sub.3 represents any one of the following groups: ##STR2## in which: m represents 1, 2 or 3,X represents oxygen or sulfur or N-R, R.sub.5 or R.sub.6, which are identical or different, represent hydrogen or alkyl or trifluoromethyl or form (C.sub.3 -C.sub.6) cycloalkyl,n represents 0, 1 or 2,R.sub.7 represents hydroxy, alkoxy, amino, or --O--CH.sub.2 --CO--NRR',R.sub.4 represents hydrogen or halogen or alkyl, alkoxy or trihaloalkyl.Type: GrantFiled: November 23, 1993Date of Patent: April 4, 1995Assignee: Adir et CompagnieInventors: Guillaume de Nanteuil, Michel Vincent, Christine Lila, Jacqueline Bonnet, Armel Fradin
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Patent number: 5403952Abstract: Novel substituted cyclic compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophic epidermolysis bullosa, and coronary thrombosis associated with atherosclerotic plaque rupture. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also be useful as novel birth control agents by preventing ovulation or implantation.Type: GrantFiled: October 8, 1993Date of Patent: April 4, 1995Assignee: Merck & Co., Inc.Inventors: William Hagmann, Charles G. Caldwell, Paul R. Gooley
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Patent number: 5399747Abstract: A new process for preparing aryl-substituted aliphatic carboxylic acids is provided. Aryl-substituted aliphatic ether or thioether compound is reacted with carbon monoxide in aqueous conditions at a temperature between about 25.degree. C. and about 200.degree. C. An acid such as hydrochloric acid may be added. As catalyst, a mixture of palladium or a palladium compound and a copper compound with at least one acid-stable ligand are present.Type: GrantFiled: January 27, 1994Date of Patent: March 21, 1995Assignee: Albemarle CorporationInventors: Kannappan Chockalingam, Tse-Chong Wu
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Patent number: 5389619Abstract: Compounds of the formula I ##STR1## where n, W, X, Y, Z, R.sup.1, R.sup.2, and R.sup.3 are as defined herein exhibit fungicidal, insecticidal, and acaracidal activity.Type: GrantFiled: March 29, 1993Date of Patent: February 14, 1995Assignee: BASF AktiengesellschaftInventors: Reinhard Doetzer, Hubert Sauter, Horst Wingert, Reinhard Kirstgen, Albrecht Harreus, Gisela Lorenz, Eberhard Ammermann
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Patent number: 5371284Abstract: Phenyl acetylenic acetals and thioacetals and their use in the treatment of allergy, asthma, inflammation, arthritis, hyperproliferative skin disease, psoriasis or contact dermatitis are disclosed. Also disclosed are intermediates useful for producing said phenyl acetylenic acetals and thioacetals.Type: GrantFiled: July 23, 1993Date of Patent: December 6, 1994Assignee: Schering CorporationInventors: Richard J. Friary, Michael J. Green, Anil K. Saksena, Vera A. Seidl
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Patent number: 5310634Abstract: A p-phenylenediamine series color developing agent or a precursor thereof having a substituent A at the ortho-position; Substituent A: ##STR1## wherein R.sup.1 represents a hydrogen atom or an alkyl group and X represents --O--R.sup.7 or ##STR2## wherein R.sup.7 represents an alkyl group, an aryl group, or a heterocyclic ring and R.sup.8 and and R.sup.9, which may be the same or different, each represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic ring, R.sup.8 and R.sup.9 may combine with each other to form a heterocyclic ring, and a process for forming an image which comprises imagewise exposing a silver halide color photographic material and thereafter color developing the color photographic material in the presence of a p-phenylenediamine series color developing agent or a precursor thereof having the aforesaid substituent A.Type: GrantFiled: October 30, 1991Date of Patent: May 10, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Hisashi Mikoshiba, Mitsugu Tanaka, Kei Sakanoue
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Patent number: 5298647Abstract: Aromatic compounds absorbing UVB and/or UVA, substituted with an amide function, selected from the group consisting of ##STR1## whose variable substituents are as defined in the specification, e.g. ##STR2## are useful as photoprotective agents or tanning accelerators.Type: GrantFiled: December 14, 1987Date of Patent: March 29, 1994Inventors: Dominique Robert, Louis Jung
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Patent number: 5288900Abstract: This invention relates to certain salts of leukotriene antagonists and the use of certain amines to form these salts as a means for selectively crystallizing optical isomers of the leukotriene antagonists recited herein.Type: GrantFiled: April 22, 1993Date of Patent: February 22, 1994Assignee: Smithkline Beecham CorporationInventors: Trevor Laird, Robert J. Mills
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Patent number: 5278338Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.Type: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace
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Patent number: 5272178Abstract: The present invention relates to compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and independently represent tert-alkyl, phenyl, or hydrogen; R.sup.3 represents hydrogen or alkyl; X represents O, S or (CH.sub.2).sub.m wherein m is 1 or 2; A represents O or S(O).sub.n wherein n is 0, 1, or 2; p is an integer from 0 to 4; and R represents alkyl; OH; OR.sup.4 wherein R.sup.4 is alkyl; or NR.sup.5 R.sup.6 wherein R.sup.5 is hydrogen or alkyl, and R.sup.6 is hydrogen, alkyl, heterocyclealkyl, substituted heterocyclealkyl, cycloalkyl, substituted cycloalkyl, phenyl, substituted phenyl, phenylalkyl, or substituted phenylalkyl, or NR.sup.5 R.sup.6 together form a heterocyclic ring which may optionally be substituted; or (CH.sub.2).sub.t COOR.sup.7 wherein t is an integer from 1 to 4 and R.sup.7 is hydrogen or alkyl; and the pharmaceutically acceptable salts thereof. The compounds are inhibitors or stimulators of superoxide generation.Type: GrantFiled: April 8, 1993Date of Patent: December 21, 1993Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 5264609Abstract: Compounds of formula I ##STR1## in which Ar is aryl and R.sup.1 and R.sup.2 are alkyl, are obtained by a process in which a compound of formula II ##STR2## where Z is a disubstituted amino group, a) is reacted with an alcohol, R.sup.2 OH, preferably under acidic conditions, to give a compound of formula III ##STR3## which is then dealkanolated, or b) is hydrolysed under acid conditions, to give a compound of formula IV ##STR4## which then alkylated. The compounds of formula I have fungicidal activity, as do many of the compounds of formula II, III and IV.Type: GrantFiled: May 14, 1992Date of Patent: November 23, 1993Assignee: Schering Agrochemicals LimitedInventors: Clive L. Cornell, Ian C. Richards
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Patent number: 5258433Abstract: Sulfoxides of alkylthiomethylphenols of the formula I ##STR1## in which R.sub.1 is hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.5 -C.sub.7 cycloalkenyl, phenyl or C.sub.7 -C.sub.9 phenylalkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.5 -C.sub.7 cycloalkyl, C.sub.5 -C.sub.7 cycloalkenyl, phenyl, C.sub.7 -C.sub.9 phenylalkyl or a radical --CH.sub.2 --SO--R.sub.5, in which R.sub.5 is C.sub.8 -C.sub.20 alkyl which may be interrupted by --O--, --S-- or --SO-- groups, mono- or dihydroxy-substituted C.sub.2 -C.sub.12 alkyl, phenyl, benzyl, --(CH.sub.2).sub.n COOR.sub.6 or --CH(CH.sub.3)COOR.sub.6, in which R.sub.6 is C.sub.1 -C.sub.20 alkyl and n is 1 or 2, R.sub.3 is hydrogen or a group --CH.sub.2 --SO--R.sub.5, in which R.sub.5 is as defined above, and R.sub.4 has the same meanings as R.sub.2 , with the proviso that only one of the radicals R.sub.2, R.sub.3 or R.sub.4 is the group --CH.sub.2 --SO--R.sub.5 and that, if R.sub.Type: GrantFiled: August 20, 1991Date of Patent: November 2, 1993Assignee: Ciba-Geigy CorporationInventors: Hans-Rudolf Meier, Paul Dubs
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Patent number: 5256692Abstract: Novel sulfur-containing compounds which inhibit the activity of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, having a sulfur-containing side-chain bonded to a hydrophobic anchor group through an acetylenic or ethylenic linkage. Pharmaceutical compositions, and methods of use for the treatment or prevention of hypercholesterolemia, atheroschlerosis, hyperlipoproteinaemia and hyperlipidemia are provided, as are novel methods for preparation and intermediate compounds.Type: GrantFiled: January 7, 1992Date of Patent: October 26, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: Eric M. Gordon, Jelka Pluscec
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Patent number: 5237089Abstract: N-substituted 3,4,5,6-tetrahydrophthalimides and their intermediates of the general formula I ##STR1## where A is --NO.sub.2, --NH.sub.2 or ##STR2## corresponding to the compounds Ia, Ib and Ic, B is --CH.sub.2 --, --CH.sub.2 --CHR.sup.1 --, --CH.sub.2 --CHR.sup.1 --CH.sub.2 --, --CH.dbd., --CH.dbd.CR.sup.1 -- or --CH.dbd.CR.sup.1 --CH.dbd., R.sup.1 being --H, --Cl, --Br or --CH.sub.3, D is ##STR3## or .dbd.C<, depending on the terminal group B, X is --H, --Cl or --Br, Y is --H, C.sub.1 -C.sub.7 -alkyl, --Cl, --Br, --CN, --CONH.sub.2 or --CO.sub.2 R.sup.2, where R.sup.2 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.5 - or C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylmercapto-C.sub.2 -C.sub.4 -alkyl, propargyl, benzyl, .alpha.-phenylethyl, .alpha.-phenylpropyl, C.sub.2 -C.sub.4 -alkyl which is monosubstituted, disubstituted or trisubstituted by F or Cl, or CH.sub.3 -substituted or Cl-substituted allyl, and Z is --COOR.sup.2, --CONR.sup.3 R.sup.4, ##STR4## or --COR.Type: GrantFiled: December 3, 1992Date of Patent: August 17, 1993Assignee: BASF AktiengesellschaftInventors: Peter Plath, Karl Eicken, Norbert Goetz, Jochen Wild, Norbert Meyer, Bruno Wuerzer
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Patent number: 5221765Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.2 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 75.degree. C. to about 200.degree. C.Type: GrantFiled: January 24, 1992Date of Patent: June 22, 1993Assignee: Ethyl CorporationInventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
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Patent number: 5220053Abstract: An improved process for the separation of enantiomers of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process involves adding a mixture of the aliphatic carboxylic acid to the material formed by: (i) forming a solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic solvent; (ii) treating said solution with a chiral organic nitrogenous base; (iii) precipitating from the reaction solution formed in step (ii) a crystalline material comprised of the less soluble diastereomeric salt. The solution is admixed with the crystalline material for a time sufficient to cause an increase in the amount of the less soluble diastereomeric salt in the crystalline material.Type: GrantFiled: January 24, 1992Date of Patent: June 15, 1993Assignee: Ethyl CorporationInventors: Azfar A. Choudhury, Abbas Kadkhodayan, Deepak R. Patil
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Patent number: 5198570Abstract: Highly fluorinated aryloxyfluoroether esters, acids and alcohols, which are intermediates in the production of vinyl monomers, are provided. Also provided is a process for making aryloxyfluoroether esters by the base catalyzed addition of hydroxyaromatic compounds to perfluorovinylether esters.Type: GrantFiled: January 31, 1990Date of Patent: March 30, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Andrew E. Feiring
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Patent number: 5192357Abstract: The invention provides compounds of formula I ##STR1## wherein W, D, R.sup.1, R.sup.2, R.sup.3, x, m, n and p are as defined in the description. The compound have valuable pesticidal activity especially against fungi, insects, nematodes, acarids and weeds.Type: GrantFiled: July 8, 1988Date of Patent: March 9, 1993Assignee: Schering Agrochemicals LimitedInventors: Geoffrey R. Cliff, Ian C. Richards
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Patent number: 5189063Abstract: Pesticidal substituted acrylic esters of the formula ##STR1## in which R.sup.1 represents alkyl, or represents unsubstituted or substituted aralkyl,R.sup.2 represents dialkylamino, or represents a radical --Z--R.sup.3,R.sup.3 represents alkyl, or represents unsubstituted or substituted aralkyl,Z represents oxygen or sulphur,A represents ##STR2## where n represents a number from 0 to 6,R.sup.4 and R.sup.5 in each case independently of one another represent alkyl, or together represent an alkylene chain having 2 to 7 carbon atoms, andR.sup.6 represents alkyl, or represents a radical ##STR3## where R.sup.7 represents alkyl, alkoxy or dialkylamino,B represents the group CH--R.sup.8 or, whereR.sup.9 represents unsubstituted or substituted alkyl, alkenyl, alkynyl, aralkyl, aryl or hetaryl, andR and Q independently of one another represent hydrogen, alkyl, halogenoalkyl or alkoxy.Type: GrantFiled: August 17, 1990Date of Patent: February 23, 1993Assignee: Bayer AktiengesellschaftInventors: Alexander Klausener, Herbert Gayer, Wolfgang Kramer, Dieter Berg, Wilhelm Brandes, Gerd Hanssler, Ulrike Wachendorff-Neumann
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Patent number: 5166373Abstract: The present invention provides novel acyclic terpenes of the formula: ##STR1## which are useful as intermediates for the industrially advantageous production of sarcophytol A.Type: GrantFiled: December 30, 1991Date of Patent: November 24, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5162405Abstract: The present invention comprises novel single-functional and mixtures of multi-functional oligomeric performance additive compounds having one or more components of Structure A R1 ? ? ##STR1## (The definitions of R, Z1, Z2, Z3, A1, A2, A3 and y are given in the Summary Section), their uses and polymeric compounds and compositions containing them which have enhanced oxidative stabilities, enhanced ultraviolet (UV) and light stabilites and/or enhanced flame retardance. An example is the bis sulfonic acid bispotassium salt reaction product from an oligomeric caprolactone diol (TONE.RTM. 260), 2-sulfobenzoic acid anhydride and potassium carbonate, and use of this product, at levels up to about 3.0%, in a general purpose bisphenol A polycarbonate resin, to enhance the fire resistance or flame retardance of the polycarbonate resin.Type: GrantFiled: March 22, 1991Date of Patent: November 10, 1992Assignee: ELF Atochem North America, Inc.Inventors: Ronald E. MacLeay, Jose Sanchez, Daryl L. Stein
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Patent number: 5145611Abstract: Carboxylic acid derivatives of the formula ##STR1## R.sub.1 is alkoxy, alkylthio, alkylsulphinyl, alkulsulphonyl, alkylamino, cycloalkyl, or cycloalkoxy or optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl or arylamino. R.sub.2 is optionally substituted aryl or, when B is alkylene also a hydrogen atom. A is a straight-chained or branched, saturated or unsaturated alkylene containing 3 to 10 carbon atoms which is optionally interrupted by a heteratom attached to a saturated carbon and has a chain length of at least 3 atoms. Y is S(O).sub.n group or oxygen, n being 0, 1 or 2. B is a valency bond or a straight-chained or branched, saturated or unsaturated alkylene containing 1 to 18 carbon atoms. Physiologically acceptable salts, esters and amides thereof are also included. The compounds are useful in the treatment of metabolic diseases.Type: GrantFiled: January 12, 1988Date of Patent: September 8, 1992Assignee: Boehringer Mannheim GmbHInventors: Hans P. Wolff, Ernst-Christian Witte, Hans-Frieder Kuehnle
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Patent number: 5145954Abstract: Compounds of formula: ##STR1## and stereoisomers thereof, wherein R.sup.1 and R.sup.2, which are the same or different, are optionally substituted alkyl; W, X, Y and Z, which are the same or different, are hydrogen, halogen, hydroxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, optionally substituted amino, optionally substituted arylazo, optionally substituted heteroarylalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted acylamino, nitro, cyano, --OR.sup.3, --SR.sup.3, --CO.sub.2 R.sup.4, --CONR.sup.5 R.sup.6, --COR.sup.7, --CR.sup.8 .dbd.NR.sup.9, --N.dbd.CR.sup.10 R.sup.11, --SOR.sup.12 or --SO.sub.2 R.sup.Type: GrantFiled: April 17, 1989Date of Patent: September 8, 1992Assignee: Imperial Chemical Industries PLCInventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Thomas E. Wiggins, David J. Tapolczay
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Patent number: 5124353Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.Type: GrantFiled: October 3, 1989Date of Patent: June 23, 1992Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey
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Patent number: 5118858Abstract: Disclosed herein are /.sup.35 S/-labelled compound of the formula (I):(C.sub.6 H.sub.5).sub.3 C.sup.35 SHand processes therefor. This Compound (I) is useful as an intermediate for the introduction of sulfur isotope into a variety of compounds. For example, it is useful in the introduction of sulfur isotope into important compounds such as 6-mercaptopurine, 5-[3-(2-(7-chloroquinolin-2-yl)ethenyl)phenyl]-8-dimethylcarbamyl-4,6-dith ioactanoic acid, a potent antagonist of leukotriene D.sub.4 ; thiophosphoric acid derivatives, photo-affinity reagents and the like.Type: GrantFiled: October 19, 1990Date of Patent: June 2, 1992Assignee: Merck Frosst Canada, Inc.Inventors: Haydn W. R. Williams, Robert N. Young, Robert J. Zamboni
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Patent number: 5118681Abstract: S-beta-dicarbonyl substituted beta-thioacrylamide compounds have been discovered to be useful as biocides and fungicides. Compositions comprising the compound and isothiazolin-3-ones and/or carries, methods of preparation of the compounds and methods of using the compounds and compositions are also disclosed.Type: GrantFiled: July 28, 1989Date of Patent: June 2, 1992Assignee: Rohm and Haas CompanyInventors: David R. Amick, Katherine E. Flynn, Cherylann Schieber
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Patent number: 5116869Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.Type: GrantFiled: September 3, 1991Date of Patent: May 26, 1992Assignee: Teijin LimitedInventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
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Patent number: 5110978Abstract: A process for the preparation of compounds of formula I ##STR1## by reacting a phenol with formaldehyde and a thiol of formula HS--C.sub.n H.sub.2n --COO--R.sub.3 under excess pressure and in the presence of dimethylamine.The symbols R.sub.1 and R.sub.2 are independently alkyl, R.sub.3 is alkyl or alkyl interrupted by --O-- or --S--, and n is 1 or 2.Type: GrantFiled: December 21, 1990Date of Patent: May 5, 1992Assignee: Ciba-Geigy CorporationInventors: Werner Stegmann, Reto Luisoli