Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/78)
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Patent number: 5550258Abstract: 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: GrantFiled: August 23, 1994Date of Patent: August 27, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Tomonori Iwasaki, Masaya Suzuki, Takashi Furukawa, Kazunori Tsushima, Takao Ishiwatari, Toru Tsuchiya
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Patent number: 5541219Abstract: 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: GrantFiled: November 3, 1994Date of Patent: July 30, 1996Assignee: Rhone-Poulenc Rorer LimitedInventors: Garry Fenton, Jonathan S. Mason, Malcolm N. Palfreyman, Andrew J. Ratcliffe
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Patent number: 5534639Abstract: 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: GrantFiled: April 24, 1995Date of Patent: July 9, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Hirotomo Masuya, Masayoshi Yamaoka
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Patent number: 5523495Abstract: 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: GrantFiled: February 13, 1995Date of Patent: June 4, 1996Assignee: Sumitomo Chemical Company LimitedInventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
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Patent number: 5514799Abstract: 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: GrantFiled: August 2, 1993Date of Patent: May 7, 1996Assignee: Enichem S.p.A.Inventors: Pushkara R. Varanasi, Kwan-Yue A. Jen, King Y. Wong, Robert M. Mininni
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Patent number: 5500484Abstract: 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: GrantFiled: August 26, 1994Date of Patent: March 19, 1996Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Koichi Yoneda, Yoichi Kido, Takeo Hosogai, Kazuo Itoi, Masahiko Kitayama
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Patent number: 5498795Abstract: 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: GrantFiled: December 29, 1994Date of Patent: March 12, 1996Assignee: Allergan, Inc.Inventors: Tae K. Song, Roshantha A. Chandraratna
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Patent number: 5498730Abstract: 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: GrantFiled: July 26, 1994Date of Patent: March 12, 1996Assignee: Korea Research Institute of Chemical TechnologyInventors: Kwang-Yun Cho, Bum-Tae Kim, Young-Sup Kim, Yong-Ki Min, No-Kyun Park, In-Howa Jeong
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Patent number: 5495054Abstract: 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: GrantFiled: May 31, 1994Date of Patent: February 27, 1996Assignee: Sepracor, Inc.Inventors: Yun Gao, Yaping Hong, Charles M. Zepp
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Patent number: 5484949Abstract: 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: GrantFiled: March 2, 1994Date of Patent: January 16, 1996Assignee: Nippon Soda Co., Ltd.Inventors: Keiichi Tsukashima, Masashi Nakajima, deceased, Masayoshi Fujimaru, Kenji Suzuki
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Patent number: 5484872Abstract: 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: GrantFiled: March 14, 1995Date of Patent: January 16, 1996Assignee: Daiso Co., Ltd.Inventors: Hiroyuki Kanesaki, Tetsuyuki Saika, Masafumi Mikami
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Patent number: 5466827Abstract: Thioalkane .alpha.,.beta.-diketones have interesting organoleptic properties and are therefore suitable as aroma substances.Type: GrantFiled: September 28, 1993Date of Patent: November 14, 1995Assignee: Haarmann & Reimer GmbHInventors: Heinz-Jurgen Bertram, Roland Emberger, Matthias Guntert, Peter Werkhoff
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Patent number: 5466845Abstract: 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: GrantFiled: October 20, 1994Date of Patent: November 14, 1995Assignee: Wacker-Chemie GmbHInventor: Christian Herzig
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Patent number: 5463083Abstract: 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: GrantFiled: January 6, 1994Date of Patent: October 31, 1995Assignee: Cytomed, Inc.Inventors: Tesfaye Biftu, Xiong Cai, Sajjet Hussion, Gurmit Grewal, T. Y. Shen
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Patent number: 5455265Abstract: 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: GrantFiled: February 11, 1993Date of Patent: October 3, 1995Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5446069Abstract: 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: GrantFiled: March 29, 1993Date of Patent: August 29, 1995Assignee: Schering CorporationInventors: Neng-Yang Shih, Pietro Mangiaracina, Michael J. Green, Ashit K. Ganguly
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Patent number: 5446173Abstract: 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: GrantFiled: March 23, 1993Date of Patent: August 29, 1995Assignee: Daiso Co., Ltd.Inventors: Hiroyuki Kanesaki, Tetsuyuki Saika, Masafumi Mikami
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Patent number: 5444084Abstract: 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: GrantFiled: February 11, 1994Date of Patent: August 22, 1995Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Yoshimi Tsuchiya, Takashi Nomoto, Morihiro Mitsuya, Katsumasa Nonoshita, Masahiro Hayashi, Toshihiko Satoh, Yoshio Sawasaki, Toshio Kamei
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Patent number: 5434151Abstract: 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: GrantFiled: August 24, 1992Date of Patent: July 18, 1995Assignee: CytoMed, Inc.Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5428174Abstract: .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: GrantFiled: August 5, 1991Date of Patent: June 27, 1995Assignee: BASF AktiengesellschaftInventors: Gernot Reissenweber, Winfried Richarz
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Patent number: 5418230Abstract: 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: GrantFiled: October 28, 1993Date of Patent: May 23, 1995Assignee: Shionogi & Co., Ltd.Inventors: Saichi Matsumoto, Tatsuo Tsuri, Masanao Inagaki, Hirokuni Jyoyama
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Patent number: 5391753Abstract: 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: GrantFiled: September 27, 1993Date of Patent: February 21, 1995Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5389656Abstract: 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: GrantFiled: July 13, 1992Date of Patent: February 14, 1995Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Uwe Kardorff, Christoph Kuenast, Hans Theobald, Thomas Kuekenhoehner
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Patent number: 5382679Abstract: 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: GrantFiled: February 10, 1993Date of Patent: January 17, 1995Assignee: Boehringer Mannheim Italia S.p.A.Inventor: Lauro Galzigna
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Patent number: 5360815Abstract: 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: GrantFiled: June 23, 1993Date of Patent: November 1, 1994Assignee: Merck Frosst Canada, Inc.Inventors: Rejean Fortin, Yves Girard, Erich Grimm, John Hutchinson, John Scheigetz
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Patent number: 5358938Abstract: 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: GrantFiled: July 13, 1992Date of Patent: October 25, 1994Assignee: CytoMed, Inc.Inventors: Xiong Cai, Saijat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5359126Abstract: 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: GrantFiled: February 7, 1994Date of Patent: October 25, 1994Assignee: Eastman Chemical CompanyInventor: Charles A. McCombs
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Patent number: 5352822Abstract: 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: GrantFiled: April 7, 1993Date of Patent: October 4, 1994Assignee: Roussel UclafInventors: Robert J. Blade, George S. Cockerill, John E. Robinson
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Patent number: 5302724Abstract: This invention provides certain sulfonamide compounds, formulations and method of use of certain sulfonamide compounds in treating susceptible neoplasms.Type: GrantFiled: April 29, 1992Date of Patent: April 12, 1994Assignee: Eli Lilly and CompanyInventors: J. Jeffry Howbert, Fariborz Mohamadi, Michael M. Spees
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Patent number: 5288750Type: GrantFiled: January 31, 1991Date of Patent: February 22, 1994Assignee: Orion-yhtyma OyInventors: Pentti Pohto, Paivi A. Aho, Reijo J. Backstrom, Erkki J. Honkanen, Inge-Britt Y. Linden, Erkki A. O. Nissinen
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Patent number: 5286899Abstract: 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: GrantFiled: August 27, 1992Date of Patent: February 15, 1994Assignee: Sepracor, Inc.Inventor: Yun Gao
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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: 5258529Abstract: 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: GrantFiled: June 15, 1990Date of Patent: November 2, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
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Patent number: 5246962Abstract: 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: GrantFiled: September 21, 1992Date of Patent: September 21, 1993Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5247098Abstract: 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: GrantFiled: June 27, 1991Date of Patent: September 21, 1993Assignee: Canon Kabushiki KaishaInventors: Hiroaki Kumagai, Tomokazu Iyoda, Takeo Shimizu
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Patent number: 5225436Abstract: 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: GrantFiled: October 15, 1991Date of Patent: July 6, 1993Assignee: Schering CorporationInventors: Neng-Yang Shih, Pietro Mangiaracina, Michael J. Green, Ashit K. Ganguly
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Patent number: 5220020Abstract: 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: GrantFiled: November 14, 1991Date of Patent: June 15, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
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Patent number: 5220037Abstract: 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: GrantFiled: January 27, 1992Date of Patent: June 15, 1993Assignee: BASF AktiengesellschaftInventors: Reinhold Schwalm, Andreas Boettcher
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Patent number: 5210219Abstract: 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: GrantFiled: July 14, 1992Date of Patent: May 11, 1993Inventor: John Stenger-Smith
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Patent number: 5208353Abstract: 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: GrantFiled: July 15, 1992Date of Patent: May 4, 1993Assignee: SmithKline Beecham Corp.Inventors: Joseph R. Flisak, Paul G. Gassman, Ivan Lantos, Wilford L. Mendelson
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Patent number: 5202500Abstract: 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: GrantFiled: November 21, 1991Date of Patent: April 13, 1993Assignee: Huels AktiengesellschaftInventors: Christoph Theis, Wilfried Latz
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Patent number: 5194619Abstract: 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: GrantFiled: February 14, 1992Date of Patent: March 16, 1993Assignee: Hoechst AktiengesellschaftInventors: Dieter Reuschling, Jurgen Rohrmann, Gerhard Erker, Reiner Nolte, Michael Aulbach, Astrid Weiss
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Patent number: 5189165Abstract: 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: GrantFiled: December 21, 1990Date of Patent: February 23, 1993Assignee: Hoechst AktiengesellschaftInventors: Gerhard Burdinski, Reinhard Kirsch, Hariolf Kottmann
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Patent number: 5175185Abstract: 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: GrantFiled: March 14, 1991Date of Patent: December 29, 1992Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5149705Abstract: 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: GrantFiled: March 13, 1987Date of Patent: September 22, 1992Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5130435Abstract: 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: GrantFiled: August 9, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 5126461Abstract: 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: GrantFiled: November 14, 1990Date of Patent: June 30, 1992Assignee: Shell Research LimitedInventors: Mark S. Baird, Ian Bruce
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Patent number: 5077411Abstract: 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: GrantFiled: June 21, 1990Date of Patent: December 31, 1991Assignee: Warner-Lambert Co.Inventors: David T. Connor, Daniel L. Flynn
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Patent number: 5041613Abstract: 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: GrantFiled: August 28, 1989Date of Patent: August 20, 1991Assignee: Eastman Kodak CompanyInventor: Charles A. McCombs
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Patent number: 5032592Abstract: 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: GrantFiled: May 30, 1989Date of Patent: July 16, 1991Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, John Oldfield, Howard Tucker