Cyano Attached Indirectly To The Piperidine Ring By Nonionic Bonding Patents (Class 546/230)
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Patent number: 5332743Abstract: Compounds of the general formula I: ##STR1## are disclosed as potent antipsychotic agents. Novel methods of use and intermediates used to make the compounds of formula I are also disclosed.Type: GrantFiled: June 12, 1992Date of Patent: July 26, 1994Assignee: McNeilab, Inc.Inventors: Ellen W. Baxter, Allen B. Reitz
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Patent number: 5300648Abstract: The invention relates to intermediates in the production of dialkylenepiperidino compounds and their enantiomers and their use for the treatment of substance p- and neurokinin-dependent pathology.Type: GrantFiled: May 4, 1992Date of Patent: April 5, 1994Assignee: Societe Anonyme: Elf SanofiInventors: Xavier Emonds-Alt, Isabelle Grossriether, Vincenzo Proietto, Didier Van Broeck
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Patent number: 5283352Abstract: Catechol compounds of formula I ##STR1## where R.sub.1, R.sub.2, R.sub.3 and X are as described herein are effective Catechol-O-methyltransferase inhibitors.Type: GrantFiled: December 7, 1992Date of Patent: February 1, 1994Assignee: Orion-yhtyma OyInventors: Reijo J. Backstrom, Kalevi E. Heinola, Erkki J. Honkanen, Seppo K. Kaakkola, Pekka J. Kairisalo, Inge-Britt Y. Linden, Pekka I. Mannisto, Erkki A. O. Nissinen, Pentti Pohto, Aino K. Pippuri, Jarmo J. Pystynen
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Patent number: 5231105Abstract: An ethylamine derivative of formula (I): ##STR1## wherein A represents a carbon atom or a nitrogen atom;B represents a substituted or unsubstituted aralkyl or aryl group;C represents hydrogen, alkyl, aralkyl, or aryl, each of which may optionally be substituted orC may optionally be bonded to A to form an alkylene bridge which is optionally substituted,Q represents a substituted or unsubstituted aryl group, said group optionally being substituted by hetero atom(s) or substituent(s) optionally containing hetero atom(s); andX represents an alkylene bridge having from 2 to 20 carbon atoms and is optionally substituted with groups which include hetero atoms with the non-hetero atom substituents optionally containing hetero atoms.Type: GrantFiled: May 22, 1989Date of Patent: July 27, 1993Assignee: Ajinomoto Co., Inc.Inventors: Masataka Shoji, Kozo Toyota, Chikahiko Eguchi, Ryota Yoshimoto, Yosikatsu Koyama, Hideki Domoto, Akira Kamimura
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Patent number: 5204474Abstract: 2,6-Diarylpiperidin-1-yl substituted 2-butene stabilizers of the formula I or IIT--CH.sub.2 --CH.dbd.CH--CH.sub.2 --T (I)T--CH.sub.2 --CH.dbd.CH--CH.sub.2 --N(E.sub.1)(E.sub.2) (II)where T is a 2,6-diarylpiperidin-1-yl moiety and E.sub.1 and E.sub.2 are independently alkyl, cycloalkyl, aralkyl or aryl, are effective in stabilizing organic materials against the deleterious effects of oxygen, heat and actinic radiation.Type: GrantFiled: June 3, 1991Date of Patent: April 20, 1993Assignee: Ciba-Geigy CorporationInventors: Glen T. Cunkle, Joseph E. Babiarz
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Patent number: 5192774Abstract: A substituted acetamide derivative of general formula (I): ##STR1## [in which Y represents as piperidino group, 1-pyrrolidinyl group or 3-hydroxy-1-pyrrolidinyl group, and Z represents a group selected from the group consisting of (a) to (e): (a) a cyano group, ##STR2## its salts, its cyclodextrin inclusion compounds and antiulcer drugs comprising them as their active ingredient are disclosed. Compounds (I) have excellent antiulcer actions and are highly safe, thus the antiulcer drugs containing the compounds are useful as a preventive and curative medicine against acute and chronic gastric ulcers, duodenal ulcers and gastric hyperacidities.Type: GrantFiled: May 7, 1990Date of Patent: March 9, 1993Assignee: Zeria Pharmaceutical Co., Ltd.Inventors: Katsuo Shinozaki, Katsuyuki Ishii, Ikuo Ueda
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Patent number: 5169856Abstract: The present invention relates to unsaturated carboxylic acid amide derivatives of the formula ##STR1## wherein ring A stands for an optionally substituted aromatic ring; R.sup.1 stands for a hydrogen atom or an optionally substituted hydrocarbon residue or forms an optionally substituted carbocyclic ring with the adjacent group --CH.dbd.C-- together with two carbon atoms constituting the ring A; R.sup.2 stands for a hydrogen atom, an optionally substituted hydrocarbon residue or an optionally substituted acyl group; R.sup.3 stands for an optionally substituted hydrocarbon residue; and n denotes an integer ranging from 2 to 6, and salts thereof, as well as the production thereof.The compounds of the present invention act on the central nervous system of mammals and has a strong anti-cholinesterase activity, which can be used for the prophylaxis and therapy of, for example, senile dementia, Alzheimer's diseases, Huntington's chorea, et., and are useful as medicines.Type: GrantFiled: February 6, 1989Date of Patent: December 8, 1992Assignee: Takeda Chemical Industries, Inc.Inventors: Giichi Goto, Akinobu Nagaoka
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Patent number: 5142089Abstract: 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 represents 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 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 represents substituted or unsubstituted amino, or R.sup.5 and R.sup.6 together represent the necessary atoms to close a heterocyclic nucleus or substituted heterocyclic nucleus, including a heterocyclic nucleus with an aliphatic or aromatic ring fused-on;R.sup.7 and R.sup.Type: GrantFiled: June 4, 1991Date of Patent: August 25, 1992Assignee: Agfa-Gevaert, N.V.Inventor: Luc J. Vanmaele
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Patent number: 5124326Abstract: A pharmaceutically efficacious pteridine compound of formula I: ##STR1## wherein A denote a bridging hydrocarbon group containing 1 to 8 carbon atoms and containing a ##STR2## group directly bonded to the phenyl group and one of the methylene radicals of the bridging A group is optionally replaced by --O--; R.sub.1 is hydrogen, a cycloalkyl group with up to 7 carbon ring atoms, or an alkyl group having 1 to 6 carbon atoms, benzyl, or aryl; R.sub.2 is hydrogen or an alkyl group having 1 to 6 carbon atoms, or wherein R.sub.1 and R.sub.2 together form a five- or six-membered heterocyclic group which optionally contains additional hetero atoms selected from the group consisting of nitrogen, oxygen, and sulfur; R.sub.3 is hydrogen or an alkyl group having 1 to 3 carbon atoms; R.sub.3 ' is hydrogen, an optionally substituted alkyl group having 1 to 3 carbon atoms, carboxyl, hydroxyl or R.sub.3 and R.sub.Type: GrantFiled: April 20, 1990Date of Patent: June 23, 1992Assignee: Roehm GmbH Chemische FabrikInventors: Ernst Mutschler, Angelika Christner, Ingrid Hofmann
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Patent number: 5116987Abstract: The invention describes a method of synthesizing a compound of the formula ##STR1## in which X=O or NR,Z=an electron-attracting group,R=H, CN or NO.sub.2,R.sub.1 +R.sub.2 +N--C.dbd.X=a 5-membered or 6-membered heterocycle, andR.sub.3 =H, R.sub.4 =OH or R.sub.3 +R.sub.4 =a bond,said method involving intermediates of the formula ##STR2## in which R.sub.5 =H, Br or N(R.sub.1)CXR.sub.2. This method of synthesis does not involve the epoxide derivative of the chroman.The novel compounds of formula (IX) form a further subject of the invention.Type: GrantFiled: September 20, 1991Date of Patent: May 26, 1992Assignee: SanofiInventors: Georges Garcia, Daniel Mettefeu, Richard Roux
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Patent number: 5109002Abstract: There are provided cycloalkyl piperidine compounds which are useful in the treatment of physiological or drug-induced psychosis or dyskinesia in a mammal. These novel compounds are selective sigma receptor antagonists and have a low potential for movement disorder side effects associated with typical antipsychotic agents.Type: GrantFiled: August 20, 1990Date of Patent: April 28, 1992Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Gary A. Cain, Paul J. Gilligan, Sang W. Tam
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Patent number: 5095133Abstract: Aminomethylene compounds of the formula ##STR1## can be prepared by reaction of C-H acid compounds of the formula ##STR2## with salts of the formula ##STR3## in the presence of alkoxides of the formulaM.sup.1 OR.sup.10 (IV)where the radicals R.sup.1 to R.sup.4, R.sup.7, R.sup.10, X.sup.- and M.sup.1 have the meaning mentioned in the description.Type: GrantFiled: July 16, 1990Date of Patent: March 10, 1992Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Helmut Kraus
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Patent number: 5091393Abstract: The invention relates to a group of tertiary 2,5-dialkyl-3-phenylpiperidine derivatives, having opiate-antagonistic activity represented by general formula 4, ##STR1## wherein A.sub.1 is hydrogen, an optionally esterified hydroxyl group or mercapto group, a group NHA.sub.8 or --CONHA.sub.8, wherein A.sub.8 is hydrogen, alkyl having 1-6 C-atoms or alkylcarbonyl having 2-7 C-atoms;A.sub.2 is hydrogen or, when A.sub.1 is hydrogen, one of the other meanings of A.sub.1, orA.sub.1 and A.sub.2 together with the 2 carbon atoms of the benzene ring,constitute a heterocyclic group which consists of five or six ring atoms and which comprises a group --NH-- and optionally as a second hetero atom may comprise an oxygen atom, sulphur atom or nitrogen atom;A.sub.3 and A.sub.4 independently of each other are straight or branched alkyl or alkenyl having 1-6 C-atoms;A.sub.Type: GrantFiled: May 29, 1990Date of Patent: February 25, 1992Assignee: Duphar International Research B.V.Inventors: Jacobus A. Den Hartog, Ineke Van Wijngaarden, Martinus T. Tulp
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Patent number: 5053504Abstract: A process is disclosed for providing benzazepine intermediates of the formulae ##STR1## wherein R.sub.3, R.sub.4 and Y are as defined herein, which intermediates are useful in a process for the preparation of pharmaceutically useful benzazepine derivatives.Type: GrantFiled: November 29, 1989Date of Patent: October 1, 1991Assignee: E. R. Squibb & Sons, Inc.Inventors: Wen-Sen Li, John K. Thottathil, Michael Murphy
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Patent number: 5053516Abstract: 3-Methyl-2-alkylamino-1-halo-1-cyano cyclobutanes are cleaved under acid conditions to form 2-halo-4-formylvaleronitrile and 4-formyl-2-pentenonitrile which can be cyclized to form 2-substituted-5-methylpyridine derivatives. These pyridine derivatives are useful as starting materials in the manufacture of herbicides such as fluazifop-butyl.Type: GrantFiled: March 12, 1990Date of Patent: October 1, 1991Assignee: ICI Americas Inc.Inventors: Ludwig A. Hartmann, John F. Stephen
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Patent number: 5047570Abstract: 3-Amino-2-cyanoacrylonitrile derivatives of the formula ##STR1## where R is substituted C.sub.1 -C.sub.10 -alkyl, substituted or unsubstituted styryl, substituted or unsubstituted phenyl or aromatic heterocyclyl, are prepared by treating a nitrile in an inert organic diluent at from 0.degree. to +30.degree. C. with a substituted or unsubstituted C.sub.1 -C.sub.6 -alkanol in the presence of a hydrogen halide and reacting the resulting iminoester hydrohalide directly or after isolation with malodinitrile in an inert organic diluent at from 20.degree. to 100.degree. C. in the presence of a base.Type: GrantFiled: February 10, 1989Date of Patent: September 10, 1991Assignee: BASF AktiengesellschaftInventor: Ernst Schefczik
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Patent number: 5039681Abstract: A novel piperidine derivative is defined by the formula (I), including a salt thereof, ##STR1## wherein R.sup.1 denotes a univalent group derived from one selected among substituted or unsubstituted benzene, pyridine, pyrazine, indole, anthraquinone, quinoline, substituted or unsubstituted phthalimide, homophthalimide, pyridinecarboxylic acid imide, pyridine N-oxide, pyrazinedicarboxylic acid imide, naphthalenedicarboxylic acid imide, substituted or unsubstituted quinazolinedione, 1,8-naphthalimide, bicyclo [2.2.2] oct-5-ene-2,3-dicarboxylic acid imide and pyromerylimide,X denotes a group of the formula --(CH.sub.2).sub.n --, a group of the formula --O(CH.sub.2).sub.n --, a group of the formula --S(CH.sub.2).sub.n --, a group of the formula --NH(CH.sub.2).sub.n --, a group of the formula --SO.sub.2 NH(CH.sub.2).sub.n --, a group of the formula ##STR2## a group of the formula ##STR3## a group of the formula ##STR4## a group of the formula --CH.sub.2 NH(CH.sub.2).sub.Type: GrantFiled: February 14, 1990Date of Patent: August 13, 1991Assignee: Eisai Co., Ltd.Inventors: Hachiro Sugimoto, Takaharu Nakamura, Yutaka Tsuchiya, Hiroyuki Sugumi, Kunizou Higurashi, Norio Karibe, Yoshiharu Yamanishi, Hiroo Ogura, Shin Araki, Atsuhiko Kubota, Michiko Ohtake, Kiyomi Tamatsu
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Patent number: 5021480Abstract: Compounds which contain azo linkages as well as a hindered amine light stabilizer moiety of low basicity function as free radical polymerization initiators and provide a polymer containing a hindered amine stabilizer chemically bonded to said polymer. The low basicity of the instant compounds prevents interaction with acid catalysts used in some polymerization systems.Type: GrantFiled: February 14, 1990Date of Patent: June 4, 1991Assignee: Ciba-Geigy CorporationInventor: Ramanathan Ravichandran
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Patent number: 5021429Abstract: Compounds of the general formula: ##STR1## and physiologically acceptable salts, and hydrates, N-oxides and bioprecursors of such compounds and such salts in whichR.sub.1 and R.sub.2, which may be the same or different, represent hydrogen or lower alkyl, cycloalkyl, aralkyl or lower alkenyl groups, or lower alkyl groups interrupted by an oxygen atom or a group ##STR2## in which R.sub.4 represents hydrogen or lower alkyl; or R.sub.1 and R.sub.2 may, together with the nitrogen atom to which they are attached form a heterocyclic ring which may contain the hetero functions --O-- and ##STR3## R.sub.3 represents hydrogen, lower alkyl, alkenyl or alkoxyalkyl; X represents --O--, --S-- or --CH.sub.2 -- or ##STR4## where R.sub.5 is hydrogen or lower alkyl; Y represents .dbd.S, .dbd.O, .dbd.NR.sub.6 or .dbd.CHR.sub.7 ;in which R.sub.6 represents hydrogen, nitro, cyano, lower alkyl, aryl, arylsulphonyl or lower alkylsulphonyl; R.sub.Type: GrantFiled: December 22, 1986Date of Patent: June 4, 1991Assignee: Allen & Hansburys LimitedInventor: Michael Martin-Smith
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Patent number: 5006523Abstract: Novel compounds of the formula ##STR1## and tautomers thereof are disclosed. These compounds possess potassium channel blocking activity and, as such, are useful as antiarrhythmic agents.Type: GrantFiled: October 26, 1989Date of Patent: April 9, 1991Assignee: E. R. Squibb & Sons, Inc.Inventor: Karnail Atwal
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Patent number: 4980349Abstract: The invention relates to new compounds corresponding to formula I: ##STR1## in which: W represents C=O, CH.sub.2 or CHOH,Z represents ##STR2## R.sub.1 and R.sub.2 represent especially Cl or F, R, R' and R" represent especially H,X represents especially CH.sub.2,Y represents especially COOH,u and v are two integers ranging from 0 to 10,p and q take the value 0 or 1,n and m are two integers ranging 0 to 10 andt is 0 or 1the total number of carbon atoms in the chain ##STR3## ranging from 2 to 20, and to their physiologically acceptable salts obtained with organic or inorganic acids.These compounds are useful for preparing medicinal products which have, especially, anti-inflammatory properties.Type: GrantFiled: November 12, 1987Date of Patent: December 25, 1990Assignee: SANOFIInventors: Pierre Roger, Jean-Paul Fournier, Alain Martin, Jean Choay
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Patent number: 4977165Abstract: A piperidine compound has the generic formula and is useful to treat arrhythmia. ##STR1## in which R.sup.1 is a lower alkyl and W is: ##STR2## X is --S--, --SO-- or --SO.sub.2 --, R.sup.2 is hydrogen or --(CH.sub.2).sub.n --Y, n is an integer of 1 to 5, Y is an aryl, pyridyl or a substituted pyridyl, X' is --CO-- or --CH(OH)--,p is an integer of 1 to 4, R.sup.12 is hydrogen or a lower alkyl, Y' is --(CH.sub.2).sub.m --A, m is 1 or 2, A is an aryl, a substituted aryl, pyridyl or a substituted pyridyl, R.sup.12 and Y may form a 5- or 6-membered ring or a 5- or 6-membered ring having one or more substituents andR.sup.22 is hydrogen, a halogen, a lower alkyl, a lower alkoxy or hydroxy.Type: GrantFiled: August 19, 1988Date of Patent: December 11, 1990Assignee: Eisai Co., Ltd.Inventors: Hitoshi Oinuma, Motosuke Yamanaka, Kazutoshi Miyake, Tomonori Hoshiko, Norio Minami, Tadao Shoji
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Patent number: 4970022Abstract: Mustard oils of the formula IR--(A.sup.1 --Z.sup.1).sub.n --A.sup.2 --Z.sup.2 --A.sup.3 --NCSin which A.sup.1, A.sup.2, A.sup.3, R, Z.sup.1, Z.sup.2 and n have the meaning specified in claim 1 can be used as components of liquid-crystalline phases.Type: GrantFiled: August 19, 1987Date of Patent: November 13, 1990Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Bernhard Scheuble, Rudolf Eidenschink, Joachim Krause, Eike Poetsch, Andreas Wachtler
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Patent number: 4950766Abstract: A method for preparing a benzamide by reacting an aromatic acid with an amine having a primary amino group and a secondary amino group wherein the reaction is directed to the primary amino group by first reacting the acid with N,N'-carbonyldiimidazole.Type: GrantFiled: September 21, 1989Date of Patent: August 21, 1990Assignee: Erbamont, Inc.Inventor: Jung-Hui Sun
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Patent number: 4942169Abstract: A novel piperidine derivative is defined by the formula (I), including a salt thereof, ##STR1## wherein R.sup.1 denotes a univalent group derived from one selected among substituted or unsubstituted benzene, pyridine, pyrazine, indole, anthraquinone, quinoline, substituted or unsubstituted phthalimide, homophthalimide, pyridinecarboxylic acid imide, pyridine N-oxide, pyrazinedicarboxylic acid imide, naphthalenedicarboxylic acid imide, substituted or unsubstituted quinazolinedione, 1,8-naphthalimide, bicyclo [2.2.2.] oct-5-ene-2,3-dicarboxylic acid imide and pyromerylimide,X denotes a group of the formula --(CH.sub.2).sub.n --, a group of the formula --O(CH.sub.2).sub.n --, a group of the formula --S(CH.sub.2).sub.n --, a group of the formula --NH(CH.sub.2).sub.n --, a group of the formula --SO.sub.2 NH(CH.sub.2).sub.n --, a group of the formula ##STR2## a group of the formula ##STR3## a group of the formula ##STR4## a group of the formula --CH.sub.2 NH(CH.sub.2).sub.Type: GrantFiled: March 10, 1989Date of Patent: July 17, 1990Assignee: Eisai Co., Ltd.Inventors: Hachiro Sugimoto, Takaharu Nakamura, Yutaka Tsuchiya, Hiroyuki Sugumi, Kunizou Higurashi, Norio Karibe, Yoshiharu Yamanishi, Hiroo Ogura, Shin Araki, Atsuhiko Kubota, Michiko Ohtake, Kiyomi Tamatsu
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Patent number: 4933367Abstract: This invention relates to carboxylic acid derivatives and their use thereof. The compounds are useful in treatment of various diseases such as diabetes, prediabetic conditions, adipositas ailments or atherosclerosis.Type: GrantFiled: March 12, 1987Date of Patent: June 12, 1990Assignee: Boehringer Mannheim GmbHInventors: Hans P. Wolff, Ernst-Christian Witte, Hans-Frieder Kuhnle
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Patent number: 4898977Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.Type: GrantFiled: August 13, 1987Date of Patent: February 6, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst
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Patent number: 4897223Abstract: Color-forming agents of the general formula ##STR1## wherein X denotes hydroxyl, alkoxy, alkenyloxy, aralkoxy, cycloalkoxy, aryloxy, acyloxy, alkoxycarbonyloxy, alkylamino, dialkylamino, acylamino, aralkylamino or arylamino,Q denotes cyano, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, carbamoyl, N-alkylcarbamoyl, N,N-dialkylcarbamoyl, N-alkyl-N-aryl-carbamoyl, acyl, alkoxysulphonyl, aralkoxysulphonyl, sulphamoyl, N-alkylsulphamoyl, N,N-dialkylsulphamoyl, alkylsulphonyl, arylsulphonyl or aralkylsulphonyl andR denotes alkyl, alkenyl or aralkyl,further isocyclic or heterocyclic rings can be fused on to the rings A, B, C and D, and the cyclic and acyclic radicals and the rings A, B, C and D can carry further substituents, are used for the preparation of pressure-sensitive recording materials.Type: GrantFiled: March 1, 1988Date of Patent: January 30, 1990Assignee: Bayer AktiengesellschaftInventors: Udo Eckstein, Hubertus Psaar, Roderich Raue
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Patent number: 4894472Abstract: The invention relates to new dicyanoethylaryl derivatives and to processes for their preparation. The compounds according to the invention can be used as redox indicators, such as, for example, for the detection of hydrogen peroxide with the aid of peroxidases or peroxidatively active substances.These redox indicators are futhermore suitable for the detection of peroxidases or peroxidatively active compounds, it also being possible to use other peroxides as oxidizing agents.Type: GrantFiled: March 21, 1988Date of Patent: January 16, 1990Assignee: Miles Inc.Inventors: Florin Seng, Klaus Wehling
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Patent number: 4889953Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a higher alkyl group which may be substituted; R.sup.2 is a hydrogen, a lower alkyl group which may be substituted, a lower alkanoyl group which may be substituted or a lower alkylthiocarbamoyl group; R.sup.3 is a primary to tertiary amino group or a quaternary ammonium group; and n is 2 or 3, and salts thereof, have antitumor activity and platelet activating factor inhibitory activity.Type: GrantFiled: July 22, 1987Date of Patent: December 26, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
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Patent number: 4876262Abstract: A new piperidine compound is pharmacologically effective for treatment of the arrythmia and is defined by the formula: ##STR1## in which R1 is a lower alkyl or a tolyl, R2 is hydrogen, hydroxyl, a lower alkoxy or a lower alkyl, R3 is hydrogen, a lower alkyl, a lower alkenyl, a cycloalkyl or a cycloalkylalkyl, X is --CO--, --CH2-- or --CHOH--, g is an integer of 1 to 3, h is an integer of 1 to 3, Y is hydrogen, a lower alkyl, a lower alkenyl, cyano, --CH2COOR, R being hydrogen or a lower alkyl, a cycloalkyl, a cycloalkylalkyl, ##STR2## 1 being 1 or 2, --A--B, A being --(CH2)n--, n being an integer of 1 to 5, a straight-chain alkylene group having 1 to 5 carbon atoms which is a divalent group derived from a straight-chain alkane having lower alkyl, phenyl or hydroxyl group(s) bonded directly to one or more carbon atoms constituting said alkane by removing a hydrogen atom bonded to each of the carbon atoms placed at both ends thereof,a straight-chain alkylene group having 1 to 5 carbon atoms which is a divalentType: GrantFiled: February 18, 1987Date of Patent: October 24, 1989Assignee: Eisai Co., Ltd.Inventors: Hitoshi Oinuma, Motosuke Yamanaka, Kazutoshi Miyake, Tomonori Hoshiko, Norio Minami, Tadao Shoji, Yoshiharu Daiku, Kohei Sawada, Kenichi Nomoto
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Patent number: 4873327Abstract: Compounds of the general formula ##STR1## in which each of A and B independently represents a halogen atom or an alkyl group; m is 0 or 1; Q represents a group of general formula ##STR2## in which R is as defined, or Q represents a group of general formula --CR.sup.2 R.sup.3 R.sup.4 in which R.sup.2, R.sup.3 and R.sup.4 are as defined; together with processes for the preparation of such compounds, pesticidal compositions containing them and their pesticidal use, and certain novel intermediates.Type: GrantFiled: March 8, 1988Date of Patent: October 10, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Martin Anderson, Anthony G. Brinnand
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Patent number: 4863966Abstract: Compounds of formula (I) are pesticides having activity against arthropods: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are H, alkyl, alkoxy, halo, cyano or trifluoromethyl, or two of R.sup.1, R.sup.2 and R.sup.3 are linked to form a 3 or 4 carbon atom group;X is O or NA where A is H or alkyl;R is H or alkyl; andR.sup.4 and R.sup.5 are H, alkenyl or haloalkenyl or optionally substituted alkyl, aryl or aralkyl, or NR.sup.4 R.sup.5 represents a heterocyclic ring; or an acid addition salt thereof.The invention further provides methods for the preparation of the compounds, pesticidal formulations containing them, and their use in controlling arthropod pests.Type: GrantFiled: February 17, 1981Date of Patent: September 5, 1989Assignee: Burroughs Wellcome Co.Inventors: Malcolm H. Black, Alexander D. Frenkel, Peter T. Roberts
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Patent number: 4849431Abstract: A novel piperidine derivative or a pharmacologically acceptable salt thereof is used in the treatment and prevention of dementias and sequelae of cerebrovascular diseases. These compounds also exhibit strong, highly selective anticholinesterase activity and may be orally or parenterally administered.Type: GrantFiled: December 24, 1986Date of Patent: July 18, 1989Assignee: Eisai Co., Ltd.Inventors: Hachiro Sugimoto, Takaharu Nakamura, Yutaka Tsuchiya, Hiroyuki Sugumi, Kunizou Higurashi, Norio Karibe, Yoshiharu Yamanishi, Hiroo Ogura, Shin Araki, Atsuhiko Kubota, Michiko Ohtake, Kiyomi Tamatsu
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Patent number: 4837236Abstract: A heterocyclic compound of the formula: ##STR1## wherein A is an oxygen atom or a sulfur atom;B is either one of the groups: --CH.sub.2 --CHR.sup.1 -- or --CH.dbd.CR.sup.1 -- (in which R.sup.1 is a hydrogen atom or a methyl group);W is, the same or different, each a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group;X is either one of the following groups: ##STR2## (in which R.sup.2 is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy(lower)alkyl group, a hydroxyl group or a hydroxy(lower)alkyl group, R.sup.3 is a hydrogen atom or a lower alkyl group and n is an integer of 0 or 1);Z is, the same or different, each a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a halo(lower)alkyl group, a halo(lower)alkoxy group, a nitro group, a methylenedioxy group or a cyano group;p is an integer of 0 to 5; andq is an integer of 0 or 1, or its salt, which is useful as a fungicide.Type: GrantFiled: September 24, 1987Date of Patent: June 6, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Naoto Meki, Hirotaka Takano
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Patent number: 4812459Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein all the symbols are defined in the specification; having pharmacological activity, including blood pressure lowering activity, a process and intermediates for their preparation and their use as pharmaceuticals.Type: GrantFiled: June 6, 1986Date of Patent: March 14, 1989Assignee: Beecham Group p.l.c.Inventors: John M. Evans, Geoffrey Stemp, Frederick Cassidy
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Patent number: 4810725Abstract: 1-Aryloxy-3-(substituted aminoalkylamino)-2-propanols and pharmaceutically acceptable salts thereof have .beta.-adrenergic blocking activity with some cardioselectivity and hence are useful as anti-hypertensive, antianginal, antiarrhythmic and cardioprotective agents and in the treatment of elevated intraocular pressure such as glaucoma.Type: GrantFiled: October 14, 1986Date of Patent: March 7, 1989Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, Gerald S. Ponticello, Sandor L. Varga
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Patent number: 4778901Abstract: Intermediates for the production of microbicidal pyrrolines of the formula ##STR1## in which R is halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 14 C.sub.6 -haloalkyl, and n is 0, 1 or 2, and a method of converting the pyrrolines to phytofungicidal pyrroles by oxidation with bromine or oxygen. Catalysts are provided for the oxidation with oxygen.Type: GrantFiled: June 3, 1987Date of Patent: October 18, 1988Assignee: Ciba-Geigy CorporationInventor: Pierre Martin
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Patent number: 4774331Abstract: A process for ortho-cyanation of phenols or phenylamines which comprises reacting a phenyl compound having hydroxy or optionally substituted amino or cyclic amino, of which ortho position is vacant, with trichloroacetonitrile, C.sub.1 -C.sub.5 alkyl thiocyanate or C.sub.6 -C.sub.12 aryl thiocyanate in the presence of a boron trihalide and treating the resultant product with an alkali is provided, and said process is useful in the synthesis of intermediates for medicinals or pesticides.Type: GrantFiled: August 21, 1987Date of Patent: September 27, 1988Assignee: Shionogi & Co., Ltd.Inventors: Makoto Adachi, Hiromu Matsumura, Tsutomu Sugasawa
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Patent number: 4735959Abstract: There are described novel carboxylic acid derivatives of the formula ##STR1## and derivatives of the formula ##STR2## and the addition salts thereof, which exhibit an effect on the intermediary metabolism. Furthermore, the compounds of Formula Ia as well as the compounds of Formula I possess blood-sugar lowering properties.Type: GrantFiled: May 14, 1985Date of Patent: April 5, 1988Assignee: Dr. Karl Thomae GmbHInventors: Wolfgang Grell, Gerhart Griss, Robert Sauter, Rudolf Hurnaus, Eckhard Rupprecht, Nikolaus Kaubisch, Joachim Kahling, Bernhard Eisele
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Patent number: 4670593Abstract: Dichloroacetamidines having the formula ##STR1## in which A and B are independently selected from hydrogen, fluorine, chlorine, bromine and methyl, provided that at least one of A or B is other than hydrogen;M is hydrogen or methyl;X is selected from the group consisting of trifluoromethyl, lower alkyl, nitro, chloro, bromo, fluoro, cyano, lower alkoxy acetyl, lower alkylthio, trifluoromethylthio, and 3,3-diloweralkyl ureido;Y is selected from the group consisting of hydrogen, lower alkyl, chloro, fluoro, nitro, trifluoromethyl, and lower alkoxy;Z is selected from the group consisting of hydrogen and chloro;R.sub.1 is selected from the group consisting of hydrogen, alkyl and allyl;R.sub.2 is selected from the group consisting of alkyl, allyl, benzyl, hydroxyalkyl, alkynyl, N-alkyl amido, alkoxyalkyl, dialkoxyalkyl, alkoxy, cyano alkyl, substituted phenyl wherein the substituent is selected from the group trifluoromethyl, dichloro and 3,3-dimethylureido; andR.sub.1 and R.sub.Type: GrantFiled: November 5, 1984Date of Patent: June 2, 1987Assignee: Stauffer Chemical Co.Inventor: Eugene G. Teach
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Patent number: 4659818Abstract: 2,4-Diamino-5-benzylpyrimidines of the formula ##STR1## wherein R.sup.1, R.sup.2, A, Z and n are as hereinafter set forth, are described. The 2,4-diamino-5-benzylpyrimidines of the invention have useful antibacterial activity. More particularly, they inhibit bacterial dihydrofolate reductase and potentiate the antibacterial activity of sulfonamides.Type: GrantFiled: February 27, 1985Date of Patent: April 21, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Ivan Kompis, Gerald Rey-Bellet, Guido Zanetti
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Patent number: 4659721Abstract: Alkanol derivatives corresponding to the general formula IR.sup.1 R.sup.2 N--(CH.sub.2).sub.m --Q--CH.sub.2 X--CH.sub.2 --Y--(CH.sub.2).sub.n --NHR.sup.3 (I)which have a highly selective action on histamine-H.sub.2 receptors are described. Due to this action, these compounds may advantageously be used for treatment of diseases caused by raised gastric secretion.Type: GrantFiled: January 22, 1985Date of Patent: April 21, 1987Assignee: Ludwig Heumann & Co. GmbHInventors: Helmut Schickaneder, Stefan Postius, Istvan Szelenyi, Peter Morsdorf, Rolf Herter, Kurt H. Ahrens
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Patent number: 4639524Abstract: Compositions of matter are disclosed of compounds of the formula ##STR1## and the pharmaceutically acceptable acid addition salts thereof wherein X represents a halo, lower alkyl, hydrogen, trifluoromethyl, phenyl, or lower alkoxy substituent; Y represents --CN, --CONH.sub.2, --CON(R.sub.1).sub.2 or --CO.sub.2 R.sub.1 where R.sub.1 is a lower alkyl; m is the integer 1 or 2 and n is an integer from 1 to 3 inclusive; R.sub.2 represents lower alkyl; R.sub.3 represents lower alkyl or acetyl, aroyl, phenacetyl or trifluoracetyl; A, B, and D are carbonyl or methylene such that when one of A, B, or D is carbonyl, the others are methylene and R.sub.3 is lower alkyl, whereas when R.sub.3 is acetyl, aroyl, phenacetyl or trifluoroacetyl, A, B, and D are methylene. These compounds have utility as antiarrhythmic agents.Type: GrantFiled: July 9, 1984Date of Patent: January 27, 1987Assignee: G. D. Searle & Co.Inventors: Bipinchandra N. Desai, Robert J. Chorvat, Kurt J. Rorig
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Patent number: 4632986Abstract: Thiocarbamylsulfenamides are readily recovered from solutions of the thiocarbamylsulfenamides by the addition of a dilute aqueous caustic solution, to flash off the solvent separating the thiocarbamylsulfenamide from the resulting water slurry and drying the thiocarbamylsulfenamide.Type: GrantFiled: July 29, 1985Date of Patent: December 30, 1986Assignee: The BFGoodrich CompanyInventors: Enrique G. Reynes, John O. Leising
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Patent number: 4614742Abstract: A fluorinated isophthalonitrile compound having the general formula ##STR1## wherein Y is --O, --S, or --N(R'), R and R' are independently hydrogen, an alkyl group, an alkyl group, an alkynyl group, a haloalkyl group, an alkoxyl group, alkoxyalkyl group, a phenyl group which may be substituted, a tetrahydrofurfuryl group, or a cycloalkyl group, provided that, in the case of Y=--N(R'), R and R' or Y may be a tetrahydrofurfuryl group, or a cycloalkyl group, a heterocyclic compound residue.This fluorinated isophthalonitrile compound is suitable for use as an agricultural fungicide.Type: GrantFiled: August 29, 1985Date of Patent: September 30, 1986Assignee: S.D.S. Biotech K.K.Inventors: Nobuo Ishikawa, Akio Takaoka, Takashi Isono, Masatoshi Motoyoshi, Kazuhiro Kojima
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Patent number: 4612329Abstract: Novel alpha-aminoalkyl-alpha-alkylphenylacetonitrile derivatives useful for treatment of cartino vaso diseases, a peripheral circulatory insufficiency and cerebral circulation failure are disclosed.Type: GrantFiled: October 11, 1985Date of Patent: September 16, 1986Assignee: Hokuriku Pharmaceutical Co., Ltd.Inventors: Yasuo Itoh, Hideo Kato, Eiichi Koshinaka, Nobuo Ogawa, Sakae Kurata, Hiroyuki Nishino, Toshihiko Yoshida
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Patent number: 4604393Abstract: This invention relates to novel piperidines substituted on the nitrogen atom with a (phenyloxo alkyl) group as well as the processes for their production.Type: GrantFiled: January 30, 1984Date of Patent: August 5, 1986Inventors: Pierre-Jean Cornu, Claude Perrin, Bernard Dumaitre, Gilles Streichenberger
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Patent number: 4600780Abstract: New N-cyano-formamidine are disclosed of the formula I: ##STR1## wherein R is 2-[[(5-methyl-1H-Imidazol-4-yl)methyl]thio]ethyl, 2-[[[5-[dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl, 2-[[[2-[(aminoiminomethyl)amino]-4-thiazolyl]methyl]thio]ethyl or 3-[3-(1-piperidinylmethyl)phenoxy]propyl, as well as a process for its production, and pharmaceutical preparations containing the same. The compounds possess histamine--induced gastric acid secretion--inhibiting activity, and are indicated for use in the treatment of peptic ulcer and other pathologies caused or stimulated by gastric acidity.Type: GrantFiled: March 20, 1984Date of Patent: July 15, 1986Assignee: Ferrer International, S.A.Inventors: Rafael Foguet, Luis Anglada, Manuel M. Raga, Jose A. Ortiz, Aurelio Sacristan, Jose M. Castello
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Patent number: 4597912Abstract: A compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 independently of one another are unsubstituted or hydroxy substituted, C.sub.1 -C.sub.4 alkoxy substituted, cyano substituted, C.sub.1 -C.sub.4 alkoxycarbonyl substituted, di-C.sub.1 -C.sub.4 alkylamino substituted, (CH.sub.3)(C.sub.6 H.sub.5 CH.sub.2)NC.sub.2 H.sub.4 substituted, chlorine substituted or bromine substituted C.sub.1 -C.sub.4 -alkyl, cyclohexyl, benzyl, phenylethyl or phenyl, R.sup.1 and R.sup.2 together with the nitrogen are morpholino, pyrrolidino, piperidino or N-methylpiperazino;R.sup.3 is hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy or nitro;R.sup.4 and R.sup.5 independently of one another are hydrogen, C.sub.1 -C.sub.4 -alkyl or benzyl; X is oxygen or imino; A.sup.Type: GrantFiled: May 17, 1985Date of Patent: July 1, 1986Assignee: BASF AktiengesellschaftInventors: Manfred Eisert, Klaus Grychtol