Cyano Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/330)
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Patent number: 5708178Abstract: Novel acceptor-donor-acceptor and donor-acceptor-donor compounds for use in forming a thermally-stable electro-optic waveguide are disclosed. Also disclosed is a thermally stable waveguide material containing thermally stable acceptor-donor-acceptor or donor-acceptor-donor guest dipole compounds in a temperature-resistant polymer matrix. The waveguide has selected regions in which the net dipoles of the guest molecules are oriented, for electro-optic switching when an electric field is placed across these regions.Type: GrantFiled: September 20, 1996Date of Patent: January 13, 1998Assignee: Lockheed Martin CorporationInventors: Susan P. Ermer, Doris S. Y. Leung, Steven M. Lovejoy
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Patent number: 5668136Abstract: A benzene, pyridine or pyrimidine derivative having the below shown formula is novel and useful as an anti-arteriosclerotic agent. ##STR1## wherein R.sup.1 stands for a lower alkyl group, an amino group which may be substituted, or the like; R.sup.2 stands for a group represented by the formula: ##STR2## (wherein R.sup.16 stands for an alkyl group having 1 to 6 carbon atoms, or the like) or the like; R.sup.3 stands for a group represented by the formula: --O--(CH.sub.2).sub.m --Y (Y stands for an imidazolyl or piperazinyl group, or the like and m is 1 to 6) or the like; R.sup.5 stands for a hydrogen atom, a lower alkyl group, or the like; A stands for a group represented by the formula: ##STR3## (wherein R.sup.6 stands for a hydrogen atom, a lower alkyl group, or the like), --N.dbd., or the like; and B stands for a group represented by the formula: ##STR4## (wherein R.sup.4 stands for a hydrogen or the like), --N.dbd., or the like.Type: GrantFiled: September 11, 1991Date of Patent: September 16, 1997Assignee: Eisai Co., Ltd.Inventors: Teiji Kimura, Nobuhisa Watanabe, Yasutaka Takase, Kenji Hayashi, Makoto Matsui, Hironori Ikuta, Youji Yamagishi, Kozo Akasaka, Hiroshi Tanaka, Issei Ohtsuka, Takao Saeki, Motoji Kogushi, Tohru Fujimori, Isao Saito
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Patent number: 5656636Type: GrantFiled: May 11, 1995Date of Patent: August 12, 1997Assignee: SmithKline Beecham CorporationInventors: Pamela Anne Chambers, Robert A. Daines, Dalia R. Jakas, William D. Kingsbury, Israil Pendrak
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Patent number: 5652252Abstract: The subject of the invention is compounds of general formula: ##STR1## in which: X represents O or CHR,R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which are identical or different, represent a hydrogen atom or a C.sub.1 -C.sub.7 alkyl group, it being possible for R.sub.1 to additionally form a bond with R;R.sub.5 represents a hydrogen atom, a hydroxyl group or R.sub.5, taken together with R.sub.7, forms a bond or a>O; group;R.sub.6 represents a group of formula: ##STR2## in which R.sub.10 and R.sub.11, taken together with the carbon atom to which they are attached, form a nitrogenous heterocyclic group,and their N-oxides and pharmaceutically acceptable salts.These compounds are powerful activators of potassium channels.Type: GrantFiled: June 5, 1995Date of Patent: July 29, 1997Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Jean Jacques Berthelon, Michel Brunet, Marc Noblet, Philippe Durbin, Daniel Guerrier, Trong Nghia Luong
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Patent number: 5650511Abstract: Derivatives of 9-deazaguanine are prepared by reacting an aldehyde or ketone with a dialkylaminomalonate to form the corresponding enamine. The enamine is then reacted with a base to form a cyclic pyrrole. The cyclic pyrrole is reacted with an urea compound to provide a protected guanidino compound. The guanidino is converted to the desired 9-deazaguanine derivative by reacting with trifluoracetic acid or with an alkoxide or hydroxide followed by neutralization with an acid.Type: GrantFiled: December 12, 1995Date of Patent: July 22, 1997Assignee: BioCryst Pharmaceuticals, Inc.Inventors: Arthur J. Elliott, David A. Walsh
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Patent number: 5643914Abstract: This invention relates to a compound of formula 1 ##STR1## or an N-oxide, or a pharmaceutically acceptable salt, where A is CH.sub.2 and Z is S(O).sub.q where q is 0, 1 or 2, CH.sub.2, CHOH, CO, NR.sub.x, or O, orA is C.dbd.O and Z is NR.sub.x ;m is 0-5;R.sub.x is hydrogen or lower alkyl;R is C.sub.1 to C.sub.20 -aliphatic, unsubstituted or substituted five-membered heteroaryl-C.sub.1 to C.sub.10 -aliphatic-O--, unsubstituted or substituted phenyl-C.sub.1 to C.sub.10 -aliphatic where substituted p from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo, or R is C.sub.1 to C.sub.20 -aliphatic-O--, or R is unsubstituted or substituted phenyl-C.sub.1 to C.sub.10 -aliphatic-O-- where substituted phenyl has one or more radicals selected from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo;R.sub.1 is R.sub.4, --(C.sub.1 to C.sub.5 aliphatic)R.sub.4, --(C.sub.1 to C.sub.5 aliphatic)CHO, --(C.sub.1 to C.sub.5 aliphatic)CH.sub.2 OR.sub.5;R.sub.2 and R.sub.Type: GrantFiled: December 19, 1994Date of Patent: July 1, 1997Assignee: SmithKline Beecham CorporationInventor: Robert A. Daines
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Patent number: 5633258Type: GrantFiled: May 11, 1995Date of Patent: May 27, 1997Assignee: SmithKline Beecham CorporationInventors: Pamela A. Chambers, Robert A. Daines, Dalia R. Jakas, William D. Kingsbury, Israil Pendrak
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Patent number: 5633257Abstract: Compounds of general formula (1) ##STR1## are described wherein Y is a halogen atom or a group --OR.sup.1, wherein R.sup.1 is an optionally substituted alkyl group; X is --O--, --S--, or --N(R.sup.6), wherein R.sup.6 is a hydrogen atom or an optionally substituted alkyl group; R.sup.2 is an optionally substituted cycloalkyl or cycloalkenyl group; R.sup.3 and R.sup.4, which may be the same or different, is each a hydrogen atom or an optionally substituted alkyl, --CO.sub.2 R.sup.7 (wherein R.sup.7 is a hydrogen atom, am optionally substituted alkyl, aralkyl, aryl, aryloxyalkyl, alkanoyloxyalkyl or aroyloxyalkyl group), --CONR.sup.8 R.sup.9 (where R.sup.8 and R.sup.9, which may be the same or different, is as defined for R.sup.7), --CSNR.sup.8 R.sup.9, --CN or --CH.sub.2 CN group; Z is --(CH.sub.2).sub.n -- where n is zero or an integer 1, 2 or 3; R.sup.Type: GrantFiled: March 9, 1994Date of Patent: May 27, 1997Assignee: Celltech Therapeutics LimitedInventors: Graham J. Warrellow, Valerie A. Cole, Rikki P. Alexander
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Patent number: 5633371Abstract: Catechol derivatives of the formula ##STR1## wherein Ra, Rb and Rc have the significance given herein, the ester and ether derivatives thereof which are hydrolyzable under physiological conditions and the pharmaceutically acceptable salts thereof are described and possess valuable pharmacological properties. In particular, they inhibit the enzyme catechol-O-methyltransferase (COMT), a soluble, magnesium-dependent enzyme which catalyses the transference of the methyl group of S-adenosylmethionine to a catechol substrate, whereby the corresponding methyl ethers are formed. Suitable substrates which can be O-methylated by COMT and which can thus be deactivated are, for example, extraneuronal catecholamines and exogeneously-administered therapeutically active substances having a catechol structure.Formula Ia above embraces not only compounds which form part of the invention, but also known compounds: the compounds which form part of the invention can be prepared according to known methods.Type: GrantFiled: September 15, 1995Date of Patent: May 27, 1997Assignee: Hoffmann-La Roche Inc.Inventors: Karl Bernauer, Janos Borgulya, Hans Bruderer, Mos e Da Prada, Gerhard Z urcher
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Patent number: 5631262Type: GrantFiled: May 11, 1995Date of Patent: May 20, 1997Assignee: SmithKline Beecham CorporationInventors: Pamela A. Chambers, Robert A. Daines, Dalia R. Jakas, William D. Kingsbury, Israil Pendrak
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Patent number: 5629323Abstract: Amide Derivatives of formula (I) wherein R.sup.1 is a mono or bicyclic heteroaryl radical, R.sup.2 is cycloalkyl, R.sup.3 and R.sup.4 each represent hydrogen or lower alkyl, and R.sup.5 is a group of formula (A) or (B) or (C): R.sup.8 --CH.sub.2 --CH.sub.2 -- or (D) or (E): R.sup.9 OCH.sub.2 CHOHCH.sub.2 -- or (F): R.sup.9 OCH.sub.2 CH.sub.2 -- and their pharmaceutically acceptable salts are 5-HT.sub.1A binding agents and may be used, for example, as anxiolytics.Type: GrantFiled: May 25, 1995Date of Patent: May 13, 1997Assignee: John Wyeth & Brother, Ltd.Inventors: Ian A. Cliffe, Anderson D. Ifill
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Patent number: 5616605Abstract: This invention is directed to a collagenase inhibitor of the formula: ##STR1##Type: GrantFiled: August 8, 1994Date of Patent: April 1, 1997Assignee: Research Corporation Tech., Inc.Inventors: Robert D. Gray, Arno F. Spatola, Krzysztof Darlak
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Patent number: 5616718Abstract: A compound having the formula: ##STR1## wherein W, X, Y, and Z are as defined in the specification is useful for making 2,4-diaminoquinazolines.Type: GrantFiled: April 20, 1995Date of Patent: April 1, 1997Assignee: FMC CorporationInventors: Robert N. Henrie, II, Clinton J. Peake, Thomas G. Cullen, Walter H. Yeager, John W. Buser, James J. Fiordeliso, John A. Dixson
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Patent number: 5602155Abstract: This invention herein relates to compounds having the following formula ##STR1## or a pharmaceutically acceptable salt thereof which are useful in the inhibition of platelet aggregation, to pharmaceutical compositions containing the compound and to a method of inhibiting platelet aggregation in mammals by administering such compounds and compositions.Type: GrantFiled: January 17, 1995Date of Patent: February 11, 1997Assignee: G. D. Searle & Co.Inventor: Peter G. Ruminski
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Patent number: 5597837Abstract: Methods of inhibiting cell proliferation in a patient suffering from such disorder comprising the use of a styryl-substituted heteroaryl compound wherein the heteroaryl group is a monocyclic ring with 1 or 2 heteroatoms, or a bicyclic ring with 1 to about 4 heteroatoms, said compound optionally substituted or polysubstituted, with the proviso that when said ring is polysubstituted, the substituents do not have a common point of attachment to said ring, and those compounds wherein no substituent on the heteroaryl group is a carboxy group or an ester group, and pharmaceutical compositions comprising such compounds.Type: GrantFiled: April 11, 1994Date of Patent: January 28, 1997Assignee: Rh one-Poulenc Rorer Pharmaceuticals Inc.Inventors: Alfred P. Spada, Paul E. Persons
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Patent number: 5563168Abstract: O-Benzyloxime ethers of the formula I ##STR1## where 5 X is substituted or unsubstituted CH.sub.2, NOalkylY isO, S, NR.sup.5R.sup.1, R.sup.2, R.sup.5 are H, alkylZ.sup.1, Z.sup.2 are H, halogen, methyl, methoxy, cyanoR.sup.3, R.sup.4 are hydrogen, cyano, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, benzylthio, alkylcarbonyl, substituted or unsubstituted phenylcarbonyl, substituted or unsubstituted benzylcarbonyl, alkoxycarbonyl, substituted or unsubstituted phenoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl,N(R.sup.6).sub.2, where R.sup.6 is H, alkyl, substituted or unsubstituted phenyl,--CO--N(R.sup.7).sub.2, where R.sup.Type: GrantFiled: June 16, 1995Date of Patent: October 8, 1996Assignee: BASF AktiengesellschaftInventors: Siegbert Brand, Uwe Kardorff, Reinhard Kirstgen, Bernd Mueller, Klaus Oberdorf, Hubert Sauter, Gisela Lorenz, Eberhard Ammermann, Christoph Kuenast, Albrecht Harreus
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Patent number: 5545744Abstract: The invention relates to a process for preparing a substituted 2-amino-benz[cd]indole of the Formula I: ##STR1## The nitro group of a substituted 1-nitro-8-cyano-naphthalene compound is reduced to an amine group to form a substituted 1-amino-8-cyano-naphthalene compound, which is cyclized to form the substituted 2-amino-benz[cd]indole. The reduction and cyclization may be effected in a one-pot procedure using a reducing agent such as stannous chloride, which generates an acid that cyclizes the reduction product. The syntheses of the 1-nitro-8-cyano-naphthalene compound and its precursors are also described.Type: GrantFiled: May 25, 1995Date of Patent: August 13, 1996Assignee: Agouron Pharmaceuticals, Inc.Inventors: Michael D. Varney, Cindy L. Palmer, Judy G. Deal
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Patent number: 5508293Abstract: Disclosed are pyridinecarboximidamides having a vasodilating effect (hypotensive activity or antianginal activity), and acid adduct salts thereof. ##STR1## wherein when R.sup.1 represents an alkyl, hydroxyalkyl, carboxyl, amino, acylamino, alkylamino, dialkylamino, aralkylamino, alkylsulfonamide, bisalkylsulfonylamino or hydroxyl group, R.sup.2 represents a hydrogen atom and R.sup.3 represents a nitroxyl, 2-chlorophenyl or phenyl group; andwhen R.sup.1 represents a hydrogen atom, R.sup.2 represents an alkyl, hydroxyalkyl, carboxyl, amino, acylamino, alkylamino, dialkylamino, aralkylamino, alkylsulfonamide, bisalkylsulfonylamino or hydroxyl group and R.sup.3 represents a nitroxyl, 2-chlorophenyl or phenyl group.There is also disclosed the use of the compounds represented by the formula (I) for antihypertensive or antianginal purpose.Type: GrantFiled: September 27, 1994Date of Patent: April 16, 1996Assignee: Kirin Beer Kabushiki KaishaInventors: Hideki Okawara, Tatsuo Nakajima, Nobuyuki Ogawa, Tomoko Kashiwabara, Soichiro Kaneta
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Patent number: 5506227Abstract: Compounds having the formula I: ##STR1## are antagonists of the actions of leukotrienes. 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.Type: GrantFiled: April 13, 1992Date of Patent: April 9, 1996Assignee: Merck Frosst Canada, Inc.Inventors: Robert Zamboni, Daniel Guay, Jacques-Yves Gauthier
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Patent number: 5502057Abstract: For the treatment of lipoproteinaemia and arteriosclerosis, the new disubstituted pyridines of the formula ##STR1## in which R.sup.1 is optionally substituted aryl or heteroaryl,R.sup.2 is cycloalkyl or optionally substituted alkyl,R.sup.3 is hydrogen, cycloalkyl, or optionally substituted alkyl, aryl or heteroaryl,x is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--,A is ##STR2## R.sup.6 is hydrogen or alkyl, and R.sup.7 is hydrogen, alkyl, aralkyl or a cation.Type: GrantFiled: July 14, 1993Date of Patent: March 26, 1996Assignee: Bayer AktiengesellschaftInventors: Rolf Angerbauer, Peter Fey, Walter Hu/ bsch, Thomas Philipps, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt, Gu/ nter Thomas
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Patent number: 5493047Abstract: The invention relates to a method of preparing an optically active cyanohydrin carboxylic acid ester from an optically active cyanohydrin of opposite configuration, wherein said starting cyanohydrin is converted with a carboxylic acid in the presence of a dialkyl azodicarboxylate and a triarylphosphine.The invention also relates to a method of preparing an optically active cyanohydrin of opposite configuration by a subsequent solvolysis of the ester obtained under conservation of the configuration.Type: GrantFiled: December 6, 1993Date of Patent: February 20, 1996Assignee: Duphar International Research B.V.Inventors: Johannes Brussee, Arne Van Der Gen, Erwin G. J. C. Warmerdam, Chris G. Kruse
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Patent number: 5489603Abstract: An insecticidal composition containing a guanidine derivative of the formula: ##STR1## wherein R.sup.1 is an optionally substituted homocyclic or heterocyclic group, n is 0 or 1, R.sup.2 is a hydrogen atom or an optionally substituted hydrocarbon group, R.sup.3 is a primary, secondary or tertiary amino group, X is an electron attractive group such as nitro or trifluoroacetyl group, provided that when n is 0, R.sup.1 is an optionally substituted heterocyclic group or a salt thereof.Type: GrantFiled: July 15, 1993Date of Patent: February 6, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Hideki Uneme, Koichi Iwanaga, Noriko Higuchi, Isao Minamida, Tetsuo Okauchi
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Patent number: 5482942Abstract: This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.Type: GrantFiled: June 28, 1994Date of Patent: January 9, 1996Assignee: American Home Products CorporationInventors: Richard M. Soll, Paul J. Dollings
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Patent number: 5482948Abstract: This invention relates to pyridyl derivatives of the formula ##STR1## wherein X, Y, A, n and R.sub.3 to R.sub.8 are defined hereinbelow, the enantiomers thereof, the cis- and trans-isomers thereof, which have antithrombotic pharmaceutical activity.Type: GrantFiled: July 5, 1994Date of Patent: January 9, 1996Assignee: Dr. Karl Thomae GmbHInventors: Rainer Soyka, Thomas Muller, Johannes Weisenberger
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Patent number: 5478497Abstract: Compounds of the formula ##STR1## wherein rings A, B and C, Z.sup.1, Z.sup.2, Z.sup.3, R.sup.1, R.sup.2 and R.sup.3 are defined in the specification, their manufacture, liquid crystalline mixtures which contain such compounds and the use of these compounds for electro-optical purposes.Type: GrantFiled: February 1, 1995Date of Patent: December 26, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Richard Buchecker, Martin Schadt, Alois Villiger
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Patent number: 5475119Abstract: Ionic monomeric diallylammonium compounds having a targeted combination of diallylammonium cations with selected anions have particularly high and constant charge control properties and very good heat stabilities and dispersibilities.The compounds according to the invention are outstandingly suitable for use as colorless charge control agents in toners and developers for electrophotographic recording processes and for use as charge-improving agents in powders and paints for surface coating, in particular in triboelectrically or electrokinetically sprayed powder paints.Type: GrantFiled: December 17, 1992Date of Patent: December 12, 1995Assignee: Hoechst AktiengesellschaftInventors: Rudiger Baur, Hans-Tobias Macholdt
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Patent number: 5475012Abstract: Antiinfluenza A activity was found in compounds of the formula: ##STR1## wherein: X is 2-phenylethyl, 2-furanylmethyl, or ##STR2## where one of R.sup.1 and R.sup.2 is H and the other is phenylamino; Z is --SCH.sub.3 when X is ##STR3## or ##STR4## when X is 2-phenylethyl or 2-furanylmethyl; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: October 13, 1994Date of Patent: December 12, 1995Assignee: American Home Products CorporationInventors: Kuo-Hom L. Hsu, Daniel M. Teller, Alan R. Davis, Michael D. Lubeck, Harry R. Munson, Jr., Gunnar E. Jagdmann, Ibrahim M. Uwaydah
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Patent number: 5468870Abstract: Dye-donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer containing a dye corresponding to the following formula ##STR1## wherein Z represents CN, COOR.sup.1 or CONR.sup.2 R.sup.3 ;R.sup.1, R.sup.2 and R.sup.3 each independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or R.sup.2 and R.sup.3 together represent the necessary atoms to close a heterocyclic nucleus or substituted heterocyclic nucleus;Y represents OR.sup.4 or NR.sup.5 R.sup.6 or CN;R.sup.4 represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, SO.sub.2 R.sup.7, COR.sup.7, CSR.sup.7, POR.sup.7 R.sup.8 ;R.sup.5 and R.sup.6 each independently has one of the significances given to R.sup.4 or represent substituted or unsubstituted amino, or R.sup.5 and R.sup.Type: GrantFiled: October 20, 1994Date of Patent: November 21, 1995Assignee: AGFA-GAVAERT, N.V.Inventor: Luc J. Vanmaele
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Patent number: 5455348Abstract: The invention relates to cyclic imino derivatives of general formulaB--X.sub.5 --X.sub.4 --X.sub.3 --X.sub.2 --X.sub.1 --A--Y--E(I)whereinA, B, E, X.sub.2 to X.sub.5 and Y are defined as in claim 1, the stereoisomers, tautomers, mixtures and salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable pharmacological properties, preferably aggregation-inhibiting effects, pharmaceutical compositions which contain these compounds and processes for preparing them.Type: GrantFiled: December 23, 1993Date of Patent: October 3, 1995Assignee: Karl ThomaeInventors: Volkhard Austel, Wolfgang Eisert, Frank Himmelsbach, Guenter Linz, Thomas Mueller, Helmut Pieper, Johannes Weisenberger
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Patent number: 5438059Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is optionally substituted aryl or optionally substituted heteroaryl; Y is oxygen, sulphur or NR.sup.4 ; R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, are hydrogen, C.sub.1-4 alkyl or C.sub.2-4 alkenyl; X is halogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkoxy, nitro or cyano; and n is 0 or an integer of 1 to 4; provided that when Y is oxygen, n is 0 and R.sup.1 is unsubstituted phenyl at least one of R.sup.2 and R.sup.3 is other than hydrogen or methyl.Type: GrantFiled: July 6, 1993Date of Patent: August 1, 1995Assignee: Zeneca LimitedInventors: John M. Clough, Christopher R. A. Godfrey, Paul J. de Fraine, Michael G. Hutchings, Vivienne M. Anthony
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Patent number: 5438065Abstract: Diaminoethylene derivatives of the formula: ##STR1## wherein R.sup.1 is a heterocyclic group which may be substituted, R.sup.2, R.sup.3 and R.sup.4 are a hydrogen atom or a hydrocarbon group which may be substituted or R.sup.3 and R.sup.4 are combined to form a cyclic amino group together with the adjacent nitrogen atom; R.sup.5 is hydrogen atom or a hydrocarbon group or heterocyclic group which may be substituted; X is an electron attractive group; Y is a hydroxyl or substituted hydroxyl group, amino or substituted amino group or mercapto or substituted mercapto group; n is 0 or 1; or their salts, which are useful as insecticides.Type: GrantFiled: April 12, 1990Date of Patent: August 1, 1995Assignee: Takeda Chemical IndustriesInventors: Hideki Uneme, Isao Minamida, Tetsuo Okauchi
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Patent number: 5434267Abstract: Process for the preparation of compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, X and n have the meaning given in the description, by reacting acetates with carbon monoxide in the presence of a basic auxiliary, followed by alkylation. The products are intermediates for fungicidal acrylates.Type: GrantFiled: March 14, 1994Date of Patent: July 18, 1995Assignee: Bayer AktiengesellschaftInventors: Helmut Kraus, Alexander Klausener, Hans-Joachim Diehr
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Patent number: 5418245Abstract: Methods of inhibiting cell proliferation in a patient suffering from such disorder comprising the use of a styryl-substituted heteroaryl compound wherein the heteroaryl group is a monocyclic ring with 1 or 2 heteroatoms, or a bicyclic ring with 1 to about 4 heteroatoms, said compound optionally substituted or polysubstituted, with the proviso that when said ring is polysubstituted, the substituents do not have a common point of attachment to said ring, and those compounds wherein no substituent on the heteroaryl group is a carboxy group or an ester group, and pharmaceutical compositions comprising such compounds.Type: GrantFiled: March 17, 1994Date of Patent: May 23, 1995Assignee: Rhone-Poulenc Rorer International (Holdings) Inc.Inventors: Alfred P. Spada, Paul E. Persons
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Patent number: 5411936Abstract: Cyclohexenone oxime ethers of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, A is substituted or unsubstituted C.sub.4 -alkylene or C.sub.4 -alkenylene,x is nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl and/or phenyl,n is from 0 to 3 or from 1 to 5 when X is halogen,R.sup.2 is C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl or C.sub.5 -C.sub.Type: GrantFiled: January 19, 1993Date of Patent: May 2, 1995Assignee: BASF AktiengesellschaftInventors: Juergen Kast, Dieter Kolassa, Norbert Meyer, Ulrich Schirmer, Albrecht Harreus, Jochen Wild, Karl-Otto Westphalen, Bruno Wuerzer
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Patent number: 5409910Abstract: New substituted pyridines are prepared by reducing suitably substituted pyridine derivatives. The new substituted pyridines are suitable as active compounds in pharmaceuticals, in particular for the treatment of hyperlipoproteinaemia.Type: GrantFiled: December 17, 1993Date of Patent: April 25, 1995Assignee: Bayer AktiengesellschaftInventors: Rolf Angerbauer, Peter Fey, Walter Hubsch, Thomas Philipps, Hilmar Bischoff, Hans-Peter Krause, Jorg P. von Gehr, Delf Schmidt
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Patent number: 5399575Abstract: Compounds of the formula I ##STR1## in which A signifies an alkylene radical with 1 to 3 carbon atoms or a group --CH.dbd.CH--, B an oxygen atom or a valency bond, m a whole number from 0 to 5, n the number 0 or 1, X a valency bond, an oxygen atom or a sulphur atom, Y a valency bond or a phenylene radical substituted, if desired, one or more times by C.sub.1 - to C.sub.6 -alkyl, C.sub.1 - to C.sub.6 -alkoxy, halogen, hydroxyl or aminocarbonyl, Z hydrogen, halogen, C.sub.1 - to C.sub.6 -alkyl or cyano and R a group CN, COOH, COOC.sub.1 - to C.sub.6 -alkyl, CONH-tetrazolyl, CON(OH)(C.sub.1 -C.sub.6 -alkyl) or 5-(1H)-tetrazolyl, as well as, for the case that Y represents a phenylene radical, also hydrogen, with the exception of the compound 4-[2-(4)-pyridinovinyl]-carboxymethoxybenzene, their physiologically compatible salts and processes for their preparation, as well as medicaments containing these compounds for the treatment of allergic diseases.Type: GrantFiled: June 14, 1993Date of Patent: March 21, 1995Assignee: Boehringer Mannheim GmbHInventors: Walter-Gunar Friebe, Wolfgang Kampe, Marcel Linssen, Otto-Henning Wilhelms
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Patent number: 5397793Abstract: A class of novel heterocyclicacetonitriles which is useful in the control of fungi, especially bitunicate asci and unitunicate asd, has been discovered. These compounds are of the general formula: ##STR1## wherein Ar.sub.1 and Ar.sub.2 are substituted or unsubstituted aryl groups; Het is a six-membered nitrogen-containing heterocyclic ring; n is the integer 2 or 3; and the agronomically acceptable enantiomorphs, add addition salts and metal complexes thereof.Type: GrantFiled: November 15, 1993Date of Patent: March 14, 1995Assignee: Rohm and Haas CompanyInventors: Steven H. Shaber, Edward M. Szapacs, Charles H. Reynolds
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Patent number: 5380734Abstract: Antiinfluenza A activity was found in compounds of the formula: ##STR1## wherein: X is 2-phenylethyl, 2-furanylmethyl, or ##STR2## where one of R.sup.1 and R.sup.2 is H and the other is phenylamino; Z is --SCH.sub.3 when X is ##STR3## when X is 2-phenylethyl or 2-furanylmethyl; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: April 15, 1993Date of Patent: January 10, 1995Assignee: American Home Products CorporationInventors: Kuo-Hom L. Hsu, Daniel M. Teller, Alan R. Davis, Michael D. Lubeck, Harry R. Munson, Jr., Gunnar E. Jagdmann, Ibrahim M. Uwaydah
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Patent number: 5371228Abstract: Dye-donor element for use according to thermal dye sublimation transfer comprising a support having thereon a dye layer containing a dye corresponding to the following formula ##STR1## wherein Z represents CN, COOR.sup.1 or CONR.sup.2 R.sup.3 ;R.sup.1, R.sup.2 and R.sup.3 each independently represent hydrogen, alkyl, cycloalkyl, aryl, or R.sup.2 and R.sup.3 together represent the necessary atoms to close a heterocyclic nucleus;Y represents OR.sup.4 or NR.sup.5 R.sup.6 ;R.sup.4 represents hydrogen, alkyl, cycloalkyl, aryl, SO.sub.2 R.sup.7, COR.sup.7, CSR.sup.7, POR.sup.7 R.sup.8 ;R.sup.5 and R.sup.6 each independently has one of the significances given to R.sup.4 or represent amino, or R.sup.5 and R.sup.6 together represent the necessary atoms to close a heterocyclic nucleus, including a heterocyclic nucleus with an aliphatic or aromatic ring fused-on;R.sup.7 and R.sup.Type: GrantFiled: August 24, 1992Date of Patent: December 6, 1994Assignee: Agfa-Gevaert, N.V.Inventor: Luc J. Vanmaele
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Patent number: 5366982Abstract: This invention relates to compounds having selective LTB.sub.4 antagonist properties, compositions comprising said compounds and methods for the treatment of disorders involving LTB.sub.4 agonist-mediated activity utilizing said compositions wherein the compounds are described by the general formula ##STR1## and pharmaceutically acceptable salts thereof.Type: GrantFiled: February 17, 1993Date of Patent: November 22, 1994Assignee: Rhone-Poulenc Rorer S.A.Inventors: Norbert Dereu, Wolfram Hendel, Richard Labaudiniere
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Patent number: 5356914Abstract: Compounds of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein R.sub.1 represents a 1,2,5,6-tetrahydropyridin-3-yl group N-substituted by R.sub.10 wherein R.sub.10 represents OH; a group hydrolysable in vivo to OH or hydrogen; C.sub.1-8 alkoxy; C.sub.2-8 alkenyloxy; C.sub.2-8 alkynyloxy; C.sub.3-8 cycloalkyloxy; or COR.sub.13 wherein R.sub.13 represents hydrogen, C.sub.1-8 alkyl, phenyl or phenyl C.sub.1-4 alkyl; in which any phenyl moiety is optionally substituted by up to 3 substituents independently selected from C.sub.1-6 alkoxy, C.sub.1-6 alkyl, halo, C.sub.1-6 alkoxycarbonyl, cyano, C.sub.1-6 alkylthio or C.sub.1-6 alkylsulphonyl; enhance acetylcholine function via an action at muscarinic receptors within the central nervous system and are therefore of potential use in the treatment and/or prophylaxis of dementia in mammals.Type: GrantFiled: April 5, 1993Date of Patent: October 18, 1994Assignee: Beecham Group p.l.c.Inventors: Steven M. Bromidge, Barry S. Orlek, Steven Dabbs
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Patent number: 5356915Abstract: The present invention relates to new tetralones having formula I: ##STR1## wherein R.sup.1 to R.sup.7 are as defined in claim 1. The invention also relates to processes for their preparation, to pharmaceutical compositions containing them and to their use in the manufacture of medicaments. These compounds are antihypertensive and bronchodilator agents.Type: GrantFiled: April 20, 1993Date of Patent: October 18, 1994Assignee: J. Uriach & Cia. S.A.Inventors: Carmen Almansa, Concepcion Gonzalez, Ma. Carmen Torres, Elena Carceller, Javier Bartroli
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Patent number: 5350871Abstract: The invention relates to a method of preparing an optically active cyanohydrin by addition of hydrogen cyanide to a carbonyl compound, selected from aldehydes and ketones, in the presence of hydroxynitrile lyase, in a biphasic solvent system, comprising a homogeneous aqueous solution of said enzyme, and a suitable organic solvent which is at least substantially immiscible with water. Said method is performed in that said homogeneous aqueous solution is buffered with an acetate buffer having a buffer concentration of between 0.005 and 0.1 mole per liter or with a non-acetate buffer, that the volume ratio organic phase:aqueous phase is between approx. 5:1 and approx. 1:5, and that a solution of hydrogen cyanide and said carbonyl compound in said organic solvent is properly mixed during the reaction period with said homogeneous aqueous solution of hydroxynitrile lyase.Type: GrantFiled: December 8, 1992Date of Patent: September 27, 1994Assignee: Duphar International Research B.V.Inventors: Hendrik W. Geluk, Wybrand T. Loos
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Patent number: 5332826Abstract: This invention relates to a process for preparing aminoacetonitriles in one vessel. The process involves the steps of: (A) reacting an alkali metal cyanide with an aldehyde in water to form a cyanohydrin; (B) extracting the cyanohydrin formed in Step (A) into a water immiscible solvent to form a two phase system comprising a water immiscible phase containing the cyanohydrin and an aqueous phase; (C) removing at least 50 weight percent, based on the weight of the water immiscible phase, of the water immiscible solvent from the water immiscible phase thereby concentrating the cyanohydrin; (D) adding a water miscible amide solvent to the concentrated cyanohydrin to form a cyanohydrin solution; and (E) passing ammonia through the cyanohydrin solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.Type: GrantFiled: October 13, 1993Date of Patent: July 26, 1994Assignee: Eastman Kodak CompanyInventor: Paul R. Buckland
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Patent number: 5332825Abstract: This invention relates to two processes for preparing aminoacetonitriles in one vessel under anhydrous conditions. Process I involves the steps of: (A) reacting trimethylsilyl cyanide and an aldehyde in a water miscible amide solvent to obtain a silyl blocked cyanohydrin solution; (B) adding a catalytic amount of water to the silyl blocked cyanohydrin solution from Step (A); and (C) passing ammonia through the solution to obtain an aminoacetonitrile. Process II involves the steps of: (A') reacting trimethylsilyl cyanide with an aldehyde in the absence of solvent to form a silyl blocked cyanohydrin; (B') adding a water miscible amide solvent to the silyl blocked cyanohydrin from Step (A') to obtain a solution; and (C') passing ammonia through the solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.Type: GrantFiled: October 13, 1993Date of Patent: July 26, 1994Assignee: Eastman Kodak CompanyInventor: Paul R. Buckland
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Patent number: 5314901Abstract: Compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein R.sub.1 represents a 1,2,5,6-tetrahydropyridin-3-yl group N-substituted by R.sub.10 wherein R.sub.10 represents hydrogen, C.sub.1-2 alkyl, prop-2-enyl, prop-2-ynyl or cyclopropyl, R.sub.2 is a group OR.sub.4, where R.sub.4 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, a group OCOR.sub.5 where R.sub.5 is hydrogen or R.sub.4, or a group NHR.sub.6, or NR.sub.7 R.sub.8 where R.sub.6, R.sub.7 and R.sub.8 are independently C.sub.1-2 alkyl; and R.sub.3 is chloro, fluoro, bromo, methoxy, C.sub.1-3 alkyl substituted by one, two or three halogen atoms, or R.sub.3 is a group (CH.sub.2).sub.n R.sub.9 where R.sub.9 is --CN, --SH or --SCH.sub.3 and n is 0 or 1, with the proviso that when n is 0, R.sub.9 is not --SH; enhance acetylcholine function via an action at muscarinic receptors within the central nervous system and are therefore of potential use in the treatment and/or prophylaxis of dementia in mammals.Type: GrantFiled: February 23, 1993Date of Patent: May 24, 1994Assignee: Beecham Group p.l.c.Inventors: Steven M. Bromidge, Barry S. Orlek, Steven Dabbs
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Patent number: 5304564Abstract: Novel guanidine derivatives of the formula (I) ##STR1## wherein Z is 2-chloro-5-pyridyl, 2-chloro-5-thiazolyl, or 3-chloro-5-isoxazolyl,R.sup.1 is hydrogen or C.sub.1-4 alkyl,R.sup.2 is hydrogen, C.sub.1-4 alkyl, C.sub.3-4 alkynyl, C.sub.3-4 alkenyl or 2-chloro-5-pyridylmethyl,R.sup.3 and R.sup.4 each represent hydrogen, halogen, C.sub.1-4 alkyl, C.sub.3-1 alkynyl, C.sub.3-4 alkenyl, benzyl which may be substituted, or Z--C(R.sup.1)H--,n is 2 or 3, andY is nitro or cyano,and pesticidal compositions comprising the compound of the formula (I) as active components.Type: GrantFiled: December 7, 1992Date of Patent: April 19, 1994Assignee: Nihon Bayer Agrochem K.K.Inventors: Shin-ichi Tsuboi, Koichi Moriya, Yumi Hattori, Shinzaburo Sone, Katsuhiko Shibuya
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Patent number: 5302606Abstract: Methods of inhibiting cell proliferation in a patient suffering from such disorder comprising the use of a styryl-substituted heteroaryl compound wherein the heteroaryl group is a monocyclic ring with 1 or 2 heteroatoms, or a bicyclic ring with 1 to about 4 heteroatoms, said compound optionally substituted or polysubstituted, with the proviso that when said ring is polysubstituted, the substituents do not have a common point of attachment to said ring, and those compounds wherein no substituent on the heteroaryl group is a carboxy group or an ester group, and pharmaceutical compositions comprising such compounds.Type: GrantFiled: April 16, 1991Date of Patent: April 12, 1994Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Alfred P. Spada, Paul E. Persons, Alexander Levitzki, Chaim Gilon
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Patent number: 5296497Abstract: The invention relates to 3,4-dehydropiperidine derivatives having psychotropic activity, which compounds are represented by the general formula 1 ##STR1## wherein R is hydrogen or C.sub.1 -C.sub.3 alkyl;R.sub.2 is hydrogen, an unsubstituted or substituted C.sub.1 -C.sub.10 hydrocarbon group, or a group of the general formula ##STR2## wherein A is C.sub.2 -C.sub.10 alkylene,R.sub.5 is hydrogen or C.sub.1 -C.sub.3 alkyl, andR.sub.6 is unsubstituted or substituted aryl or heteroaryl, hydrocarbon, substituted or unsubstituted (hetero)aralkyl, or substituted or unsubstituted heterocyclic; or wherein R.sub.5 and R.sub.6 together with the carbamoyl group to which they are bound constitute a heterocyclic ring system;n has the value 1 or 2; andZ is a heterocyclic group.Type: GrantFiled: October 30, 1992Date of Patent: March 22, 1994Assignee: Duphar International Research B.V.Inventors: Jan Hartog, Roelof Van Hes, Berend Olivier, Ineke Van Wijngaarden
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Patent number: RE35230Abstract: A method of enantiomerically enriching chiral cyanohydrins is disclosed that involves selective cleavage of the unwanted enantiomer into its cleavage products HCN and the corresponding aldehyde or ketone by use of an enantioselective dehydrocyanation catalyst, coupled with simultaneous removal of at least one of the dehydrocyanation products.Type: GrantFiled: February 7, 1994Date of Patent: May 7, 1996Assignee: Bend Research, Inc.Inventor: Paul van Eikeren