Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/78)
  • Patent number: 5550258
    Abstract: The present invention provides an ester compound represented by a formula I: ##STR1## wherein R.sub.1 denotes a hydrogen atom or a methyl group; R.sub.2 represents a 1-methyl-2-propenyl group, a 1-methyl-2-propynyl group, a 3,3-dihalogeno-1-methyl-2-propenyl group, or a C.sub.1 -C.sub.1 6 alkyl group which may be substituted with at least one halogen atom; and R.sub.3 represents an acid residue of pyrethroids.The invention also relates to an active agent for controlling noxious insect pests containing the ester compound as an active ingredient, an intermediate for production of the ester compound and a process for producing the intermediate. The ester compound represented by the formula I has good activities for controlling noxious insect pests.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: August 27, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tomonori Iwasaki, Masaya Suzuki, Takashi Furukawa, Kazunori Tsushima, Takao Ishiwatari, Toru Tsuchiya
  • Patent number: 5541219
    Abstract: This invention is directed to 1-alkoxy-2-(alkoxy- or cycloalkyloxy-)-4-(cyclothioalkyl- or cyclothioalkenyl-)benzene compounds that inhibit cyclic AMP phosphodiesterase or tumor necrosis factor (TNF) and are useful in treating patients suffering from disease state capable of being modulated by inhibiting production of cyclic AMP phosphodiesterase or TNF by administering the compound to the patient. The invention is also directed to the preparation of these compounds, pharmaceutical compositions containing these compounds and methods for their pharmaceutical use.
    Type: Grant
    Filed: November 3, 1994
    Date of Patent: July 30, 1996
    Assignee: Rhone-Poulenc Rorer Limited
    Inventors: Garry Fenton, Jonathan S. Mason, Malcolm N. Palfreyman, Andrew J. Ratcliffe
  • Patent number: 5534639
    Abstract: There are disclosed novel hydroquinone derivatives of the formulas: ##STR1## The derivatives of the formula (I) have various pharmacological activities such as antioxidation in living bodies and are useful as medicaments, and the derivatives of the formula (II) are intermediates for the production thereof.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: July 9, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirotomo Masuya, Masayoshi Yamaoka
  • Patent number: 5523495
    Abstract: The present invention provides a process for producing a propargylcarbinol compound of formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are as defined herein. The process comprises reacting a haloallylcarbinol compound of formula (II) with a base. The present invention also relates to a process for producing the haloallylcarbinol compound. The above propargylcarbinol compound is useful as an intermediate for agrochemicals, pharmaceuticals, perfumes, resin monomers, and the like.
    Type: Grant
    Filed: February 13, 1995
    Date of Patent: June 4, 1996
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
  • Patent number: 5514799
    Abstract: Nonlinear optical compounds having structures with delocalized resonance configurations corresponding to: ##STR1## wherein A.sub.1 and A.sub.2 are independently selected from electron withdrawing moieties; R.sub.1 and R.sub.2 are independently selected from aromatic rings, heteroaromatic rings and fused ring systems consisting of two or three aromatic or heteroaromatic rings; n and m are integers from one to five, and D.sub.1 and D.sub.2 are independently selected from hydrogen, electron donating groups and polymer attachment groups, with the proviso that at least one of D.sub.1 and D.sub.2 is an electron donating group. Polymers blended with, cured with, or having pendant side chains of the disclosed nonlinear optical materials and exhibiting second order nonlinear optical properties are also disclosed.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: May 7, 1996
    Assignee: Enichem S.p.A.
    Inventors: Pushkara R. Varanasi, Kwan-Yue A. Jen, King Y. Wong, Robert M. Mininni
  • Patent number: 5500484
    Abstract: A compound that can be converted, at a low cost and in a simple way, into 2-aryl-1,3-propanediols serving as precursors for synthesizing felbamate acting as an antiepileptic has a structure represented by Formula (1): ##STR1## wherein Ar represents an aryl group; R.sup.1 represents a hydrogen atom or is R.sup.4 or R.sup.5, where R.sup.4 represents an alkoxy group having 1 to 10 carbon atoms and R.sup.5 represents a hydroxy group or an acyloxy group having 1 to 10 carbon atoms; and R.sup.2 and R.sup.3 are hydrogen atoms at the same time or R.sup.2 and R.sup.3 together form a group represented by Formula (2): ##STR2## wherein R.sup.6 and R.sup.7 each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, or R.sup.6 and R.sup.7 together form an oligomethylene group having 2 to 10 carbon atoms.
    Type: Grant
    Filed: August 26, 1994
    Date of Patent: March 19, 1996
    Assignee: Kuraray Co., Ltd.
    Inventors: Hideharu Iwasaki, Koichi Yoneda, Yoichi Kido, Takeo Hosogai, Kazuo Itoi, Masahiko Kitayama
  • 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: 5498730
    Abstract: The present invention provides fluorinated alkyl compound derivatives represented by formula of: ##STR1## wherein: R is C.sub.2-4 lower alkyl, cyclohexyl or thiophene; phenyl substituted with hydrogen, C.sub.1-6 alkyl, haloalkyl, halogen or alkoxy; and,R.sub.f is fluorinated C.sub.1-3 lower alkyl.The fluorinated alkyl compound derivatives of the invention can be used as agrochemicals, drugs and intermediates therefor. The present invention also provides a novel process for preparing the fluorinated alkyl compound derivatives (I).
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: March 12, 1996
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kwang-Yun Cho, Bum-Tae Kim, Young-Sup Kim, Yong-Ki Min, No-Kyun Park, In-Howa Jeong
  • Patent number: 5495054
    Abstract: A method for the enantioselective reduction of prochiral ketones using catalytic amounts of tetrahydroindeno[1,2-d][1,3,2] oxazaboroles of formula II is disclosed. ##STR1## The oxazaboroles can be generated in situ from the corresponding cis-1-amino-2-indanols or imino indanols (III) ##STR2## Novel compounds of formulas II and III are also disclosed.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: February 27, 1996
    Assignee: Sepracor, Inc.
    Inventors: Yun Gao, Yaping Hong, Charles M. Zepp
  • Patent number: 5484949
    Abstract: The present invention relates to a method for the synthesis of .alpha., .beta.-unsaturated ketones which comprises, in the method for the synthesis of .alpha., .beta.-unsaturated ketones represented by general formula ##STR1## reacting aldehydes represented by general formulaR.sup.1 CHO(where R.sup.1 is as defined above) with alkali metal salt of acetoacetic acid represented by general formula ##STR2## (where M.sup..sym. is an alkali metal ion), in the presence as a catalyst of 3-azabicyclo[3,2,2]nonane, a cyclic secondary amine represented by general formula (1) ##STR3## a cyclic secondary amine represented by general formula (2) ##STR4## (where, l is 1 or more and up to 6, a ring with N is a 6-membered, 7-membered or 8-membered ring, the two neighbors of N are methylene, R.sup.3 is a lower alkyl group, its substitution position is at a carbon atom other than two those adjacent to N, and ##STR5## is an alicyclic group or a phenol group), or a secondary amine represented by general formula (3)CH.sub.3 NHCH.
    Type: Grant
    Filed: March 2, 1994
    Date of Patent: January 16, 1996
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Keiichi Tsukashima, Masashi Nakajima, deceased, Masayoshi Fujimaru, Kenji Suzuki
  • Patent number: 5484872
    Abstract: The present invention provides a cyclic sulfide compound represented by a general formula (I) ##STR1## (where R.sup.1 represents --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --O--CH.sub.2 --, --CH.sub.2 --O--, or --CH.sub.2 --S--). According to this invention, a novel cyclic sulfide compound which gives high refractive index and high Abbe number can be obtained. The polymerizable compositions for manufacturing optical products with this compound as their main component can be readily molded into plastic lenses which give superhigh refractive indices and high Abbe numbers or those which give high refractive indices and high Abbe number with low sp.grs. in addition thereto. The castings obtained from said polymerizable compositions are useful as plastic lenses for glasses, manifesting optical uniformity and being excellent in processability, transparency, and thermal, impact and light resistance.
    Type: Grant
    Filed: March 14, 1995
    Date of Patent: January 16, 1996
    Assignee: Daiso Co., Ltd.
    Inventors: Hiroyuki Kanesaki, Tetsuyuki Saika, Masafumi Mikami
  • Patent number: 5466827
    Abstract: Thioalkane .alpha.,.beta.-diketones have interesting organoleptic properties and are therefore suitable as aroma substances.
    Type: Grant
    Filed: September 28, 1993
    Date of Patent: November 14, 1995
    Assignee: Haarmann & Reimer GmbH
    Inventors: Heinz-Jurgen Bertram, Roland Emberger, Matthias Guntert, Peter Werkhoff
  • Patent number: 5466845
    Abstract: The present invention provides photoactive sulfonium salts which can be employed as photoinitiators for the polymerization of cationically polymerized organic substances and are soluble in these substances.
    Type: Grant
    Filed: October 20, 1994
    Date of Patent: November 14, 1995
    Assignee: Wacker-Chemie GmbH
    Inventor: Christian Herzig
  • Patent number: 5463083
    Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i,e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. Also disclosed is a method to treat disorders mediated by PAF and/or leukotrienes that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier, to a patient in need of such therapy.
    Type: Grant
    Filed: January 6, 1994
    Date of Patent: October 31, 1995
    Assignee: Cytomed, Inc.
    Inventors: Tesfaye Biftu, Xiong Cai, Sajjet Hussion, Gurmit Grewal, T. Y. Shen
  • Patent number: 5455265
    Abstract: Process of treatment of mammals, including humans to treat diseases or conditions of the type which are normally treated with retinoid-like compounds is disclosed, with pharmaceutical compositions containing an active compound which is a selective agonist of the RXR retinoid receptor sites in preference to the RAR retinoid receptor sites. A compound is defined to be a selective agonist of the RXR receptor site if the compound is at least approximately ten times more effective as an agonist in the RXR receptor sites than in the RAR receptor sites.
    Type: Grant
    Filed: February 11, 1993
    Date of Patent: October 3, 1995
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5446069
    Abstract: Disclosed are compounds of formula ##STR1## wherein F represents: ##STR2## or a pharmaceutically acceptable salt. The compounds are useful in treating hyperproliferative skin disease, allergic reactions and inflamation.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: August 29, 1995
    Assignee: Schering Corporation
    Inventors: Neng-Yang Shih, Pietro Mangiaracina, Michael J. Green, Ashit K. Ganguly
  • Patent number: 5446173
    Abstract: The present invention provides a cyclic sulfide compound represented by a general formula (I) ##STR1## (where R.sup.1 represents --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --O--CH.sub.2 --, --CH.sub.2 --O--, or --CH.sub.2 --S--). Polymerizable compositions for manufacturing optical products with this compound as their main component can be readily molded into plastic lenses which give superhigh refractive indices and high Abbe numbers or those which give high refractive indices and high Abbe number with low sp.grs. in addition thereto. The castings obtained from said polymerizable compositions are useful as plastic lenses for glasses, manifesting optical uniformity and being excellent in processability, transparency, and thermal, impact and light resistance. Further these polymerizable resin compositions are usable preferably as such optical products as prisms, optical fibers, optical disc substrates, color filters, or infrared absorption filters.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: August 29, 1995
    Assignee: Daiso Co., Ltd.
    Inventors: Hiroyuki Kanesaki, Tetsuyuki Saika, Masafumi Mikami
  • Patent number: 5444084
    Abstract: Substituted heterocyclic derivatives represented by the formula (I) ##STR1## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, Q.sup.1, Q.sup.2, Q.sup.3, Q.sup.4, X and Y are as defined, including, specifically, the compound (E)-3-[3-[3-(2-methoxymethyl-8,8-dimethyl-4-nonen-6-ynyl)phenoxymethyl]phe nyl]thiophene, exhibit squalene epoxidase inhibiting activity and are useful in the treatment or prophylaxis of hypercholesterolemia, hyperlipidemia and arteriosclerosis.
    Type: Grant
    Filed: February 11, 1994
    Date of Patent: August 22, 1995
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Yoshimi Tsuchiya, Takashi Nomoto, Morihiro Mitsuya, Katsumasa Nonoshita, Masahiro Hayashi, Toshihiko Satoh, Yoshio Sawasaki, Toshio Kamei
  • Patent number: 5434151
    Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.
    Type: Grant
    Filed: August 24, 1992
    Date of Patent: July 18, 1995
    Assignee: CytoMed, Inc.
    Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
  • Patent number: 5428174
    Abstract: .alpha.,.beta.-Unsaturated ketones of the general formula I ##STR1## where R is an organic radical, are prepared by reacting a corresponding aldehyde R--CHO with acetoacetic acid or one of its salts in the presence of an amine in a two-phase reaction mixture by a process in which the reaction is carried out at a pH of from 6 to 8 in the presence of a catalytic amount of a primary amine.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: June 27, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Winfried Richarz
  • Patent number: 5418230
    Abstract: Benzylidene derivatives having anti-inflammatory activities, are shown by the following formula I: ##STR1## wherein A is -CH.sub.2 - or -CH.sub.2 CH.sub.2 -; B is a bond or -CH.sub.2 -, -CHOH-, -CO-, -O-, or A and B may taken together form -CH=CH-; D is >N- or >CH-; R.sup.1 and R.sup.2 each independently is hydrogen, lower alkyl or lower alkoxy; R.sup.3 is hydrogen, lower alkyl, cycloalkyl, lower alkoxy, arylalkyloxy, heteroarylalkyloxy, lower alkylcarbonyl, arylcarbonyl, substituted or unsubstituted carbamoyl, or a group of the formula:-(CH.sub.2).sub.n -R.sup.4wherein R.sup.4 is hydrogen, hydroxy, substituted or unsubstituted amino, aryl, heteroaryl, hydroxycarbonyl or lower alkyloxycarbonyl; n is an integer of 0-3.
    Type: Grant
    Filed: October 28, 1993
    Date of Patent: May 23, 1995
    Assignee: Shionogi & Co., Ltd.
    Inventors: Saichi Matsumoto, Tatsuo Tsuri, Masanao Inagaki, Hirokuni Jyoyama
  • Patent number: 5391753
    Abstract: Compounds of the formula ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen, lower alkyl of 1-6 carbons, halogen or lower alkoxy of 1-6 carbons; R.sub.5 and R.sub.5 ' independently are hydrogen or lower alkyl of 1-6 carbons; Y is oxygen or sulfur; Z is n-alkyl having 1-10 carbons, cyclo or branch-chained alkyl of 3-10 carbons, and straight chain alkenyl having 2-10 carbons, or cyclo or branched chained alkenyl of 3-10 carbons; X is thienyl, pyridyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl and oxazolyl; 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.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: February 21, 1995
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5389656
    Abstract: Acetylene derivatives of the Formula IR.sup.1 --C.tbd.C--R.sup.2 Iwhere R.sup.1 is an unsubstituted or substituted five-membered heteroaromatic structure and R.sup.2 is an unsubstituted or substituted mononuclear to trinuclear aromatic ring system, their preparation, insecticides and acaricides containing them and methods for their use.
    Type: Grant
    Filed: July 13, 1992
    Date of Patent: February 14, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Uwe Kardorff, Christoph Kuenast, Hans Theobald, Thomas Kuekenhoehner
  • Patent number: 5382679
    Abstract: A selective and high yield process for S-acylating glutathione, comprising the eaction between glutathione and an acyl chloride or a carboxylic anhydride in trifluoroacetic acid is described.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: January 17, 1995
    Assignee: Boehringer Mannheim Italia S.p.A.
    Inventor: Lauro Galzigna
  • Patent number: 5360815
    Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.
    Type: Grant
    Filed: June 23, 1993
    Date of Patent: November 1, 1994
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Rejean Fortin, Yves Girard, Erich Grimm, John Hutchinson, John Scheigetz
  • Patent number: 5358938
    Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl terahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiphenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.
    Type: Grant
    Filed: July 13, 1992
    Date of Patent: October 25, 1994
    Assignee: CytoMed, Inc.
    Inventors: Xiong Cai, Saijat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
  • Patent number: 5359126
    Abstract: Preparing cyclohexanediones of the formula ##STR1## an aldehyde is reacted with a ketene to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the cyclohexanedione give the productwherein:R is selected, e.g.
    Type: Grant
    Filed: February 7, 1994
    Date of Patent: October 25, 1994
    Assignee: Eastman Chemical Company
    Inventor: Charles A. McCombs
  • Patent number: 5352822
    Abstract: The present invention discloses pesticidally active compounds of formula (II) ##STR1## or a salt thereof, wherein Q is an monocyclic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halogen or hydrogen; R.sup.2, R.sup.3 , R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy and X.sup.1 is hydrogen, fluoro or chloro.
    Type: Grant
    Filed: April 7, 1993
    Date of Patent: October 4, 1994
    Assignee: Roussel Uclaf
    Inventors: Robert J. Blade, George S. Cockerill, John E. Robinson
  • Patent number: 5302724
    Abstract: This invention provides certain sulfonamide compounds, formulations and method of use of certain sulfonamide compounds in treating susceptible neoplasms.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: April 12, 1994
    Assignee: Eli Lilly and Company
    Inventors: J. Jeffry Howbert, Fariborz Mohamadi, Michael M. Spees
  • Patent number: 5288750
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: February 22, 1994
    Assignee: Orion-yhtyma Oy
    Inventors: Pentti Pohto, Paivi A. Aho, Reijo J. Backstrom, Erkki J. Honkanen, Inge-Britt Y. Linden, Erkki A. O. Nissinen
  • Patent number: 5286899
    Abstract: An efficient and commercially-viable method for the stereoselective transformation of a diol to an alcohol is disclosed. The present method is particularly well-suited for the preparation of the unnatural D-isomer of malic acid or its derivatives from the abundant naturally occurring L-tartaric acid or derivatives thereof.
    Type: Grant
    Filed: August 27, 1992
    Date of Patent: February 15, 1994
    Assignee: Sepracor, Inc.
    Inventor: Yun Gao
  • Patent number: 5278338
    Abstract: 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: Grant
    Filed: November 4, 1992
    Date of Patent: January 11, 1994
    Assignee: Ethyl Corporation
    Inventor: Rhonda L. Trace
  • Patent number: 5258529
    Abstract: The present invention provides a process for producing a propargylcarbinol compound of formula (I): ##STR1## where R.sup.1 and R.sup.2 are as defined herein. The process comprises reacting a haloallycarbinol compound of formula (II) with a base. The present invention also relates to a process for producing the haloallylcarbinol compound. The above propargylcarbinol compound is useful as an intermediate for agrochemicals, pharmaceuticals, perfumes, resin monomers, and the like.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: November 2, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
  • Patent number: 5246962
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH or an ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.1 or a ketal derivative thereof where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: September 21, 1992
    Date of Patent: September 21, 1993
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5247098
    Abstract: Thiophene derivatives represented by the general formula (I): ##STR1## where R is an aldehyde, carboxyl, C.sub.1-5 -alkyl ester or C.sub.1-5 -alkyl acetal group and n is 3 to 5, are prepared. These compounds are reversibly converted to their respective isomers by light irradiation, accompanied with a large shift of absorption and emission bands, thus suitable for a photo-responsive material.
    Type: Grant
    Filed: June 27, 1991
    Date of Patent: September 21, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroaki Kumagai, Tomokazu Iyoda, Takeo Shimizu
  • Patent number: 5225436
    Abstract: Certain aryl substituted naphthalene, benzoxepine, benzazepine and henzocycloheptene derivatives are disclosed. The compounds are useful in treating hyperproliferative skin disease, allergic reactions and inflammation.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: July 6, 1993
    Assignee: Schering Corporation
    Inventors: Neng-Yang Shih, Pietro Mangiaracina, Michael J. Green, Ashit K. Ganguly
  • Patent number: 5220020
    Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: June 15, 1993
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
  • Patent number: 5220037
    Abstract: Novel sulfonium salts useful as photoinitiators for cationic polymerization and for producing relief patterns and relief images have the general formula (I) ##STR1## where A.sup..crclbar. is a non-nucleophilic counterion,x is 1, 2 or 3,R is a hydrocarbon radicalR' is arylene or substituted arylene, andR" is ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are each alkyl or monohalogenated or polyhalogenated alkyl orR.sup.1 and R.sup.2 are each hydrogen or alkyl, and R.sup.3 is phenyl, alkenyl or cycloalkenyl, orR.sup.1 is hydrogen, and R.sup.2 and R.sup.3 form ethylenically unsaturated ring, orR.sup.1 and R.sup.2 are each hydrogen, alkyl, cycloalkyl or aryl, and R.sup.3 is alkoxy orR.sup.1 is hydrogen or alkyl and R.sup.2 and R.sup.3 are each alkoxy, aryloxy or substituted aryloxy.
    Type: Grant
    Filed: January 27, 1992
    Date of Patent: June 15, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhold Schwalm, Andreas Boettcher
  • Patent number: 5210219
    Abstract: Novel conjugated stilbenylene polymers are disclosed having non-linear optical properties, and which can be converted to electrically conductive polymers. Such polymers are produced by reacting a novel bis-cycloalkylene sulfonium salt of 2,5-dimethyl stilbene, e.g. 2,5-(4'-methoxy)-stilbene dimethylene bis-(tetramethylene sulfonium bromide), with alkali metal hydroxide to form a cycloalkylene sulfonium salt precursor polymer, and then heating the precursor polymer under conditions to produce the stilbenylene vinylene polymer, e.q. poly(2,5-(4'-methoxy) stilbenylene vinylene).
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: May 11, 1993
    Inventor: John Stenger-Smith
  • Patent number: 5208353
    Abstract: This invention relates to a process for preparing epoxy esters, and intermediates prepared by this process, in particular, to a process which produces non-racemic epoxy esters which are of use as intermediates in the preparation of pharmaceutical compounds.
    Type: Grant
    Filed: July 15, 1992
    Date of Patent: May 4, 1993
    Assignee: SmithKline Beecham Corp.
    Inventors: Joseph R. Flisak, Paul G. Gassman, Ivan Lantos, Wilford L. Mendelson
  • Patent number: 5202500
    Abstract: Arylacetaldehyde-dialkylacetals are prepared with high yields and selectivity from the corresponding chloromethylaromatics in the presence of hydrogen chloride acceptors and methyl carbonyl compounds as catalysts and in the presence of orthoesters as water-binding agents by hydroformylation with carbon monoxide and hydrogen.
    Type: Grant
    Filed: November 21, 1991
    Date of Patent: April 13, 1993
    Assignee: Huels Aktiengesellschaft
    Inventors: Christoph Theis, Wilfried Latz
  • Patent number: 5194619
    Abstract: The compounds of the formula I or Ia ##STR1## in which R.sup.1 is alkyl, aryl, alkoxy, alkenyl, arylalkyl, alkylaryl, aryloxy, fluoroalkyl, halogenoaryl, alkynyl, trialkylsilyl or a heteroaromatic radical,R.sup.2, R.sup.3 and R.sup.4, in addition to hydrogen, have the meanings given under R.sup.1 andR.sup.5 is hydrogen, alkyl, fluoroalkyl or alkenyl, can be obtained in a one-stage process by reaction of a compound II ##STR2## with (substituted) cyclopentadiene in the presence of a base. The compounds I and Ia are suitable as ligands for metallocene complexes which are used as catalysts in olefin polymerization.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: March 16, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dieter Reuschling, Jurgen Rohrmann, Gerhard Erker, Reiner Nolte, Michael Aulbach, Astrid Weiss
  • Patent number: 5189165
    Abstract: A process for preparing a compound I ##STR1## with A=t-butyl, aryl andR=alkyl, alkenyl, alkynyl, alkenynyl, cycloalkyl(alkyl), aryl, arylalkyl, alkyl-S-(-O)-arylby reacting a compound III ##STR2## with a compound IV ##STR3## under the conditions of a phase-transfer reaction, is described. The process gives excellent yields and is not associated with the unpleasant odor of mercaptans.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: February 23, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Burdinski, Reinhard Kirsch, Hariolf Kottmann
  • Patent number: 5175185
    Abstract: Retinoid like activity is exhibited by compounds of the formula ##STR1## R.sub.1 -R.sub.3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and A.sub.1 independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR.sub.4 or OR.sub.4 where R.sub.4 is lower alkyl, cycloalkyl or lower alkenyl; Y is selected from a group consisting of thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl or oxazolyl; E is lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl, or is characterized by the formula (CH.sub.2).sub.n where n is 0-5, and Z is H, OH, OR.sub.5, OCOR.sub.5, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH, CH.sub.2 OR.sub.6, CH.sub.2 OCOR.sub.6, or --CHO, CH(OR.sub.7).sub.2, CHOR.sub.8 O, or COR.sub.9, CR.sub.9 (OR.sub.7).sub.2, CR.sub.9 OR.sub.8 O where R.sub.5 is lower alkyl, phenyl or lower alkylphenyl, R.sub.6 is lower alkyl, phenyl or lower alkylphenyl, R.sub.7 is lower alkyl, R.sub.
    Type: Grant
    Filed: March 14, 1991
    Date of Patent: December 29, 1992
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5149705
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH or an ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative thereof, or --CHO or an acetal derivative thereof, or --COR.sub.1 or a ketal derivative thereof where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: March 13, 1987
    Date of Patent: September 22, 1992
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5130435
    Abstract: Vinyl ethers of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are identical to or different from one another, each being hydrogen, straight-chain or branched alkyl or alkenyl of up to 12 carbon atoms, cycloalkyl or cycloalkylene of from 5 to 8 carbon atoms, aryl, alkylaryl, alkenylaryl, aralkyl and aralkenyl of from 6 to 16 carbon atoms, halogen-substituted aryl or heterocyclyl, and in addition the radicals R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3, together with the carbon atom to which they are bonded, can form a cycloalkane, cycloalkene or a heterocycle, and R.sup.4 is alkyl, alkylaryl or aralkyl, are prepared by eliminating an alcohol from an acetal/ketal of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: August 9, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
  • Patent number: 5126461
    Abstract: Process for ring opening compounds of the formula ##STR1## in which R.sup.1 is heteroaryl or aryl, R.sup.2 is a leaving group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, alkyl, aralkyl, aryl, heteroaryl and alkenyl, provided that at least one of the groups R.sup.3 to R.sup.6 is other than hydrogen, by breaking the bond joining the carbon atom attached to R.sup.3 and the carbon atom attached to R.sup.6 in organic solution using silica, giving useful diene or allyl derivatives, certain of which are novel.
    Type: Grant
    Filed: November 14, 1990
    Date of Patent: June 30, 1992
    Assignee: Shell Research Limited
    Inventors: Mark S. Baird, Ian Bruce
  • Patent number: 5077411
    Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migrains, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.
    Type: Grant
    Filed: June 21, 1990
    Date of Patent: December 31, 1991
    Assignee: Warner-Lambert Co.
    Inventors: David T. Connor, Daniel L. Flynn
  • Patent number: 5041613
    Abstract: Processes, intermediates, and products involved in preparing cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketone type compound of the formula (R.sub.1)(R.sub.2)C.dbd.C.dbd.O at a temperature below about 110.degree. C. to give a polymer having the repeating unit --OCH(R)C(R.sub.1)(R.sub.2)CO].sub.n wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: August 20, 1991
    Assignee: Eastman Kodak Company
    Inventor: Charles A. McCombs
  • Patent number: 5032592
    Abstract: A compound of the formula ##STR1## wherein X has the formula ##STR2## wherein ring a is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano, trifluoromethyl, alkylthio, alkylsulphinyl, and alkylsulphonyl or each is hydrogen, alkyl, alkoxy or dialkylamino provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R.sup.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: July 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, John Oldfield, Howard Tucker