Double Bond Between Ring Members Of The Hetero Ring Patents (Class 549/479)
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Patent number: 5438056Abstract: The compounds of the present invention have the following formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently phenyl, pyridyl, thienyl, naphthyl, substituted phenyl wherein the substituent is selected from the group consisting of halogen, methoxy, and dialkylamino wherein alkyl contains 1 to 3 carbon atoms; or R.sup.1 and R.sup.2 are independently substituted furanone of the structure ##STR2## wherein R.sup.5 and R.sup.6 are independently alkyl containing 1 to 3 carbon atoms, cycloalkyl containing 5 to 7 carbon atoms, phenyl or substituted phenyl wherein the substituent is alkyl containing 1 to 5 carbon atoms or halogen; R.sup.7 is hydrogen or halogen; or R.sup.1 and R.sup.2 are joined to form ##STR3## R.sup.3 and R.sup.4 are independently hydrogen, alkyl containing 4 to 20 branched, straight chain, cyclic, saturated or unsaturated carbon atoms; or R.sup.3 and R.sup.4 are joined to form ##STR4## wherein R.sup.Type: GrantFiled: October 5, 1993Date of Patent: August 1, 1995Assignee: American Home Products CorporationInventors: Steven W. Felman, Kevin A. Memoli, Ivo Jirkovsky
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Patent number: 5436352Abstract: The present invention provides metal chelating compounds, to chelates and chelate-targeting agent conjugates formed from the chelating compounds, and to methods for making and using these compositions. The chelating compounds incorporate two nitrogen atoms and three sulfur atoms ("N.sub.2 S.sub.3 "), two nitrogen atoms and four sulfur atoms ("N.sub.2 S.sub.4 "), or three nitrogen atoms and three sulfur atoms ("N.sub.3 S.sub.3 "). Metals, and metal oxides, capable of being chelated by the compounds include those that are radionuclides, such as .sup.99m Tc and .sup.186/188 Re.The targeting agent portion of the chelate-targeting agent conjugates provided includes antibodies, peptides, hormones, enzymes and biological response modifiers. Methods for making the conjugates are provided and encompass the addition of a metal, or metal oxide, to a chelating compound prior to attachment to a targeting agent as well as subsequent to the attachment.Type: GrantFiled: December 6, 1991Date of Patent: July 25, 1995Assignee: NeoRx CorporationInventors: Ananthachari Srinivasan, Alan R. Fritzberg, David S. Jones
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Patent number: 5416235Abstract: A process for the preparation of aromatic compounds of the general formula I,Ar--X Iin which Ar represents an optionally substituted aryl group and X represents a group OH, Cl, Br or CN, by reaction of an aryl diazoniumsalt of the formula II,Ar--N.dbd.N.sup.+ Y.sup.- IIin which Ar is as defined above and Y represents a suitable counterion, with water, hydrogen chloride or a salt thereof, hydrogen bromide or a salt thereof, or a cyanide in the presence of a copper(I)salt, characterized in that the copper(I)salt is a copper(I)salt derived from an hydroxy carboxylic acid.Type: GrantFiled: November 1, 1993Date of Patent: May 16, 1995Assignee: Octel Chemicals LimitedInventors: Bruce C. Gilbert, Peter Hanson, Jason R. Jones, Allan W. Timms
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Patent number: 5416223Abstract: Water insoluble iodinated esters of formula (I), in which R.sup.1 is a substituted or unsubstituted C.sub.1-20 aliphatic, C.sub.7-20 araliphatic or C.sub.6-20 aryl group or a C.sub.1-20 heterocyclic group having one or more hereto atoms selected from O, S and N; R.sup.2 is hydrogen or a substituted or unsubstituted C.sub.1-6 aliphatic, C.sub.6-10 aryl or C.sub.7-20 araliphatic group; and R.sup.3 is a group as defined above for R.sup.1, which may be the same as or different from R.sup.1, or R.sup.2 and R.sup.3 together represent a substituted or unsubstituted C.sub.1-4 alkylene group, the molecule containing at least one iodine atom and being metabolisable to products which are soluble in body fluids and are physiologically acceptable. The esters are useful in X-ray and ultrasound imaging, especially liver and spleen imaging.Type: GrantFiled: September 30, 1994Date of Patent: May 16, 1995Assignee: Nycomed Imaging ASInventors: Jo Klaveness, Per Strande
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Patent number: 5409944Abstract: Disclosed are compounds of Formula I useful in the treatment of cyclooxygenase mediated diseases such as pain, fever and inflammation of a variety of conditions including rheumatic fever, symptoms associated with influenza or other viral infections, common cold, low back and neck pain, dysmenorrhea, headache, toothache, sprains and strains, myositis, neuralgia, synovitis, arthritis, including rheumatoid arthritis degenerative joint diseases (osteoarthritis), gout and ankylosing spondylitis, bursitis, burns, injuries.Type: GrantFiled: March 12, 1993Date of Patent: April 25, 1995Assignee: Merck Frosst Canada, Inc.Inventors: W. Cameron Black, Chun-Sing Li, Daniel Guay, Petpiboon Prasit, Patrick Roy
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Patent number: 5391577Abstract: N-phenylalkyl substituted .alpha.-amino carboxamide derivatives of formula (I) ##STR1## wherein R is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, furyl, thienyl, pyridyl or unsubstituted or substituted phenyl; A is a --(CH.sub.2).sub.m -- or --(CH.sub.2).sub.p --X--(CH.sub.2).sub.q -- group wherein X is --O--, --S-- or --NR.sub.4 --; R.sub.1, R.sub.2, R.sub.3, R'.sub.3, R.sub.4, n, m, p and q are as herein defined; and each of R.sub.5 and R.sub.6 is independently hydrogen or C.sub.1 -C.sub.6 alkyl, and the pharmaceutically acceptable salts thereof, are active on the central nervous system and can be used as anti-epileptic, anti-Parkinson, neuroprotective, antidepressant, antispastic and/or hypnotic agents in mammals.Type: GrantFiled: May 25, 1993Date of Patent: February 21, 1995Assignee: Farmitalia Carlo Erba S r lInventors: Philippe Dostert, Paolo Pevarello, Franco Heidempergher, Mario Varasi, Alberto Bonsignori, Romeo Roncucci
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Patent number: 5387594Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical,and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function.Use in human and veterinary medicine and in cosmetics.Type: GrantFiled: August 4, 1992Date of Patent: February 7, 1995Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Jean-Michel Bernardon, William R. Pilgrim
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Patent number: 5374644Abstract: Compounds of formula: ##STR1## and stereoisomers thereof, wherein X, Y and Z, which are the same or different, are hydrogen, halogen, hydroxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted aralkyl, optionally substituted arylalkoxy, optionally substituted aryloxyalkyl, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, cyano, --CO.sub.2 R.sup.1, --CONR.sup.2 R.sup.3, or --COR.sup.Type: GrantFiled: December 31, 1991Date of Patent: December 20, 1994Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey, Ian T. Streeting
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Patent number: 5330965Abstract: Cyclohexenone oxime ethers of the formula I ##STR1## (R.sup.1 =C.sub.1 -C.sub.6 -alkyl; A=substituted or unsubstituted alkylene or alkenylene;Z=a 5-membered or 6-membered heteroaromatic structure;X=substituted or unsubstituted amino, nitro, cyano, halogen, 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 phenyl;n=0 to 3, or 1 to 4 where Z is halogen-substituted pyridyl; andR.sup.Type: GrantFiled: January 15, 1993Date of Patent: July 19, 1994Assignee: BASF AktiengesellschaftInventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Norbert Goetz, Albrecht Harreus, Thomas Kuekenhoehner, Bruno Wuerzer, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
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Patent number: 5326883Abstract: The present invention provides certain substituted oxime ether compounds which inhibit lipoxygenase enzyme activity and are useful in the treatment of allergic and inflammatory disease states. The compounds of this invention have the structure ##STR1## where M is hydrogen, a pharmaceutically acceptable cation, or a pharmaceutically acceptable metabolically cleavable group; p and q are independently zero or one, with the provisos that (i) p and q may not both be the same; (ii) when p is one and q is zero, R is selected from the group consisting of hydrogen, straight or branched alkyl of from one to twelve carbon atoms, and cycloalkyl of from three to eight carbon atoms; and (iii) when p is zero and q is one, R is selected from the group consisting of hydrogen, alkyl of from one to twelve carbon atoms, cycloalkyl of from three to eight carbon atoms, and --NR.sub.1 R.sub.2.L.sub.Type: GrantFiled: December 18, 1992Date of Patent: July 5, 1994Assignee: Abbott LaboratoriesInventors: Dee W. Brooks, Andrew O. Stewart, Robert G. Maki
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Patent number: 5314913Abstract: The present invention relates to novel 4- or 5-(substituted sulfonyl)methyl-3(2H)-furanones having the formula (I) ##STR1## wherein R.sup.1 and R.sup.2 are independently alkyl containing 1 to 6 branched or straight chain carbon atoms, phenyl, or halogen substituted phenyl; or R.sup.1 and R.sup.2 are joined by 5 to 7 carbon atoms;R.sup.3 and R.sup.4 are independently hydrogen, alkyl containing 1 to 6 branched or straight chain carbon atoms or R.sup.3 and R.sup.4 are joined by 4 to 6 carbon atoms;R.sup.Type: GrantFiled: December 8, 1992Date of Patent: May 24, 1994Assignee: American Home Products CorporationInventors: Steven W. Felman, Ivo L. Jirkovsky, Kevin A. Memoli
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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: 5274072Abstract: Provided are certain novel substituted 2(5H)furanone compounds which are useful as ultraviolet/visible light absorbing compounds. Also provided are polyester compositions having such compounds copolymerized therein and shaped or formed articles comprised of such polyester compositions.Type: GrantFiled: May 4, 1992Date of Patent: December 28, 1993Assignee: Eastman Kodak CompanyInventors: Max A. Weaver, James J. Krutak, Clarence A. Coates, Jr., William W. Parham, Wayne P. Pruett, Samuel D. Hilbert
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Patent number: 5270301Abstract: The present invention relates to certain fluoro-amide derivatives, as described herein, which are human leukocyte elastase (HLE) inhibitors making them useful whenever such inhibition is desired, such as for research tools in pharmacological, diagnostic and related studies and in the treatment of diseases in mammals in which HLE is implicated, including treatment of tissue degenerative diseases such as pulmonary emphysema. The invention also includes intermediates useful in the synthesis of these fluoro-amide derivatives, processes for preparing them, pharmaceutical compositions containing such peptide derivatives and methods for their use.Type: GrantFiled: May 7, 1990Date of Patent: December 14, 1993Assignee: ICI Americas Inc.Inventor: Donald J. Wolanin
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Patent number: 5254595Abstract: Aryloxypropanolaminotetralins with beta-antagonist activity of the formula ##STR1## wherein R is hydrogen, hydroxy or methoxy and Ar is an optionally substituted aromatic or heteroaromatic group, in optically active or inactive form as well as their acid addition salts are described.A process for their preparation and pharmaceutical compositions containing the compounds of formula (i) or their pharmaceutically acceptable acid addition salts, are also described.Type: GrantFiled: January 9, 1992Date of Patent: October 19, 1993Assignee: Elf SanofiInventors: Umberto Guzzi, Marco Baroni, Sergio Boveri, Luciano Manara, Alberto Bianchetti
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Patent number: 5238957Abstract: New esters of 2,2-dimethyl-cyclopropane-carboxylic acid, which are endowed ith insecticidal and acaricidal activity, have the general formula: ##STR1## wherein: represents ##STR2## or aR.sub.1 --Y--CF.sub.2 --C.tbd.C--group;Y represents either O or S;X represents H, F, Cl, Br, or --CF.sub.3 ;R.sub.1 represents either a linear or a branched (C.sub.1 -C.sub.6)-aklyl group, or a (C.sub.3 -C.sub.6)-cycloalkyl group, optionally substituted with halogen atoms;R.sub.2 represents one from the following groups: ##STR3## wherein: R.sub.3 represents an F atom, a (C.sub.1 -C.sub.5)-aklyl, an alkyloxy, an alkylthio, an alkylsulfinyl, or an alkylsulfonyl group; andY.sub.1 is either O or CH.sub.2.Type: GrantFiled: October 14, 1992Date of Patent: August 24, 1993Assignee: Presidenza Del Consiglio Dei Ministri-Uffico del Ministro per il coordinamento delle Iniziative per la ricerca Scientifica e TecnologicaInventors: Luigi Capuzzi, Franco Bettarini, Paolo Castoro, Sergio Massimini, Vincenzo Caprioli
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Patent number: 5234946Abstract: The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7,X and Y are linking groups,R.sup.2 is H or lower alkyl,R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl,R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms,R.sup.Type: GrantFiled: August 30, 1991Date of Patent: August 10, 1993Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Hiroshi Takezawa, Masahiro Hayashi, Yoshikazu Iwasawa, Masaaki Hosoi, Yoshiaki Iida, Yoshimi Tsuchiya, Masahiro Horie, Toshio Kamei
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Patent number: 5232936Abstract: The present invention relates to novel hydantoin derivatives, processes for producing said hydantoin derivatives, pharmaceutical compositions containing at least one of said hydantoin derivatives as aldose reductase inhibitors and novel intermediate compounds in the synthesis of said hydantoin derivatives.The present invention is based on the selection of a hydantoin which is bonded by a sulfonyl group to various substituents at the 1-position of the hydantoin skeleton.The compounds of the present invention have a strong inhibitory activity against aldose reductase. These compounds are extremely useful for the treatment and/or prevention of various forms of diabetic complications based on the accumulation of polyol metabolites.Type: GrantFiled: January 23, 1991Date of Patent: August 3, 1993Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Ei Mochida, Kimihiro Murakami, Kazuo Kato, Katsuaki Kato, Jun Okuda, Ichitomo Miwa
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Patent number: 5229393Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.Type: GrantFiled: April 6, 1992Date of Patent: July 20, 1993Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey
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Patent number: 5228896Abstract: Cyclohexenone oxime ethers of the formula I ##STR1## (R.sup.1 =C.sub.1 -C.sub.6 -alkyl; A=substituted or unsubstituted alkylene or alkenylene;Z=a 5-membered or 6-membered heteroaromatic structure;X=substituted or unsubstituted amino, nitro, cyano, halogen, 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 phenyl;n=0 to 3, or 1 to 4 where Z is halogen-substituted pyridyl; andR.sup.Type: GrantFiled: May 8, 1991Date of Patent: July 20, 1993Assignee: BASF AktiengesellschaftInventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Norbert Goetz, Albrecht Harreus, Thomas Kuekenhoehner, Bruno Wuerzer, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
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Patent number: 5217991Abstract: Non-peptidyl compounds characterized generally as cycloalkyl/cycloalkylalkyl-N-terminal cycloalkoxy-C-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from cycloalkyl and cycloalkylalkyl groups, wherein said cycloalkyl group contains three to about eight carbon atoms and the acyclic alkyl portion of said cycloalkylalkyl group contains one to about eight carbon atoms; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl: wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 and R.sub.Type: GrantFiled: May 28, 1992Date of Patent: June 8, 1993Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
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Patent number: 5216013Abstract: Non-peptidyl compounds characterized generally as heterocyclic acyl aminodiol .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are compounds of the formula ##STR1## wherein R.sub.1 is selected from aryl and aralkyl groups represented by ##STR2## and wherein R.sub.1 may be further selected from heteroaryl and heteroaralkyl represented by ##STR3## wherein each of T and A is independently selected from N and CH; wherein n is a number selected from zero through five, inclusive; wherein X is selected from oxygen atom, methylamino and NH; wherein each of Y and Z is independently selected from chloro, fluoro, methoxy and dimethylamino; wherein Q is oxygen atom; and wherein each of T and A is independently selected from N and CH; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is selected from methyl and ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; wherein R.Type: GrantFiled: July 16, 1992Date of Patent: June 1, 1993Assignee: G. D. Searle & Co.Inventor: Gunnar J. Hanson
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Patent number: 5214188Abstract: 2,3-dicyanonaphthalene derivatives useful in the synthesis of naphthalocyanine derivatives are disclosed. The 2,3-dicyanonaphthalene derivatives have the formula: ##STR1## wherein each R.sup.1 may be the same or different and represents an alkyl group, substituted alkyl group, or aryl group; and n is an integer from 1 to 4.Type: GrantFiled: May 2, 1991Date of Patent: May 25, 1993Assignees: Hitachi, Ltd., Hitachi Chemical Company, Ltd.Inventors: Seiji Tai, Shigeru Hayashida, Nobuyuki Hayashi, Hideo Hagiwara, Mitsuo Katayose, Koichi Kamijima, Takayuki Akimoto, Susumu Era, Setsuo Kobayashi, Akio Mukoh
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Patent number: 5207816Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1 is alkyl, R.sup.2 is alkyl, unsubstituted or halogen-substituted alkenyl or alkynyl, X is a substituted or unsubstituted five-membered heteroaromatic radical, and Z is hydrogen, methoxycarbonyl, ethoxycarbonyl, methyl or cyano, processes for their manufacture, and the use of these compounds for controlling undesirable plant growth.Type: GrantFiled: June 6, 1991Date of Patent: May 4, 1993Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Dieter Jahn, Michael Keil, Hans Theobald, Wolfgang Spiegler, Bruno Wuerzer
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Patent number: 5190573Abstract: Cyclohexenone oxime ethers ##STR1## where R.sup.1 is alkyl;A is substituted or unsubstituted alkylene or alkenylene, where methylene is replaced by an oxygen atom, a sulfur atom, a sulfoxyl group, a sulfonyl group or --NR.sup.a --,Z is phenyl or a 5- or 6-membered heteroaromatic structure;X is substituted or unsubstituted amino, nitro, cyano, halogen, 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 benzyloxycarbony or phenyl;n is 0 to 3, or 1 to 5 where X is halogen;R.sup.Type: GrantFiled: May 8, 1991Date of Patent: March 2, 1993Assignee: BASF AktiengesellschaftInventors: Ulf Misslitz, Norbert Meyer, Juergen Kast, Norbert Goetz, Albrecht Harreus, Bruno Wuerzer, Helmut Walter, Karl-Otto Westphalen, Matthias Gerber
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Patent number: 5187192Abstract: Compounds of the structure ##STR1## where M is a pharmaceutically acceptable cation or a metabolically cleavable group, R is alkyl, cycloalkyl or --NR.sup.1 R.sup.2, where R.sup.1 and R.sup.2 are hydrogen, alkyl, cycloalkyl or alkanoyl, and A is optionally substituted alkyl, cycloalkyl, carbocyclic aryl, benzo[b]furyl, thienyl, or benzo[b]thienyl are potent inhibitors of lipoxygenase enzymes and thus inhibit the biosynthesis of leukotrienes. These compounds are useful in the treatment or amelioration of allergic and inflammatory disease states.Type: GrantFiled: March 13, 1992Date of Patent: February 16, 1993Assignee: Abbott LaboratoriesInventors: Dee W. Brooks, Karen E. Rodriques
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Patent number: 5179121Abstract: Novel 4-chloro-4,4-difluorothiobutyric acid derivatives of the formula I ##STR1## in which R.sub.1 and R.sub.2 are, independently of one another, hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 halogenoalkyl and R.sub.3 is hydrogen or an organic radical can be employed as pest-control agents. Control of insects and arachnids is possible and preferable.Type: GrantFiled: August 15, 1991Date of Patent: January 12, 1993Assignee: Ciba-Geigy CorporationInventors: Peter Maienfisch, Manfred Boger, Eginhard Steiner
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Patent number: 5171867Abstract: The present invention relates to a method of preparing 2,5-dimethyl-4-hydroxy-2H-furan-3-one. It consists in reacting hydrogen peroxide with 2,5-dimethyl-2H-furan-3-one in the presence of a base.Type: GrantFiled: July 10, 1991Date of Patent: December 15, 1992Assignee: SanofiInventors: Roland Fellous, Gerard George
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Patent number: 5169854Abstract: Compounds useful in inhibiting the biosynthesis of leukotrienes have the structure ##STR1## where M is hydrogen, a pharmaceutically acceptable cation, or a metabolically cleavable group, R.sup.4 is alkyl, cycloalkyl or --NR.sup.5 R.sup.6, where R.sup.5 and R.sup.6 are hydrogen, alkyl, cycloalkyl or alkanoyl, where A is a valence bond or is a straight or branched divalent alkylene group of from one to twelve carbon atoms, R.sup.2 and R.sup.3 are independently selected from hydrogen, straight or branched alkyl of from one to twelve carbon atoms, halogen, or trifluoroalkyl, and R.sup.1 is selected from phenoxy, phenylthio, 2-, 3-, or 4-pyridyloxy, 1 or 2-naphthyloxy, or 2,4,5, or 8-quinolyloxy, all optionally substituted with alkyl, haloalkyl, alkoxy, hydroxy or halogen.Type: GrantFiled: February 26, 1992Date of Patent: December 8, 1992Assignee: Abbott LaboratoriesInventors: Dee W. Brooks, Andrew O. Stewart, Pramila Bhatia, Richard A. Craig
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Patent number: 5162364Abstract: A compound of formula (I): ##STR1## in which R, R.sub.1 and R.sub.2 are as defined in the description. Medicinal product, which is useful in treating disorders related to a dysfunction of GABA.sub.B receptors.Type: GrantFiled: June 11, 1991Date of Patent: November 10, 1992Assignee: Adir et CompagnieInventors: Michel Debaert, Pascal Berthelot, Claude Vaccher
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Patent number: 5158962Abstract: Fungicidal substituted amino acid amides of the formula ##STR1## in which Ar and Ar' are identical or different and represent unsubstituted or substituted aryl, unsubstituted or substituted aralkyl, unsubstituted or substituted heteroaryl and unsubstituted or substituted heteroarylalkyl, andR.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are identical or different and represent hydrogen or alkyl orR.sup.3 and R.sup.4, together with the carbon atom to which they are bonded, form a cycloalkyl ring.Type: GrantFiled: October 2, 1990Date of Patent: October 27, 1992Assignee: Bayer AktiengesellschaftInventors: Thomas Seitz, Detlef Wollweber, Wilhelm Brandes
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Patent number: 5145703Abstract: The invention relates to new thio-alkanones of the formula ##STR1## in which X represents an oxygen or sulphur atom,R.sub.1 represents hydrogen or a C.sub.1 -C.sub.2 -alkyl group and the broken lines represent a single bond or no bond,to a process for their preparation and their use as flavorings.Type: GrantFiled: May 16, 1991Date of Patent: September 8, 1992Assignee: Haarmann & ReimerInventors: Roland Emberger, Matthias Gunter, Rudolf Hopp, Manfred Kopsel, Walter Kuhn, Peter Werkhoff
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Patent number: 5128370Abstract: New furans and lactones from streptomycetes, a process for the preparation thereof, and the use thereof.It is possible with the aid of various streptomycetes species to prepared new compounds having a furan or lactone structure. These compounds have a pharmacological, especially antibiotic, action.Type: GrantFiled: March 20, 1989Date of Patent: July 7, 1992Assignee: Hoechst AktiengesellschaftInventors: Susanne Grabley, Joachim Wink, Klaus Kuhlein, Gerhard Seibert, Klaus Hutter, Hermann Uhr, Axel Zeeck
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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: 5055471Abstract: This invention relates to derivatives of propanoic acid of the formula ##STR1## Useful as fungicides, insecticides and miticides, to processes for preparing them, to compositions containing them, and to methods of using them to combat fungi, especially fungal infections of plants, and to kill or control insects and mites.Type: GrantFiled: November 15, 1989Date of Patent: October 8, 1991Assignee: Imperial Chemical Industries PLCInventors: Paul J. de Fraine, Anne Martin
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Patent number: 5053430Abstract: Novel compounds having the general formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined herein. These compounds are useful in the treatment of schizophrenia.Type: GrantFiled: September 22, 1989Date of Patent: October 1, 1991Assignee: Boehringer Ingelheim KGInventors: Matthias Grauert, Herbert Merz, Joachim Mierau, Gunter Schingnitz, Claus Schneider
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Patent number: 5049676Abstract: A process for the preparation of optically active esters of 2-chloropropionic acid of the formula: ##STR1## from an optically active lactate of the formula: ##STR2## with inversion of configuration. COOR.sub.1 in formula I and formula II is a hydrolyzable group. The lactate of formula II is brought into contact with SOCl.sub.2, followed by decomposition of the chlorosulfite formed, the process being one in which at least the decomposition stage is carried out in the presence of an ether.Type: GrantFiled: May 30, 1990Date of Patent: September 17, 1991Assignee: Rhone-Poulenc ChimieInventors: Pascal Metivier, Harivelo Rajoharisson
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Patent number: 5010102Abstract: A compound of the formula: ##STR1## in which R is alkyl, phenyl or halophenyl; R.sup.2 is substituted phenyl having from 1 to 3 substiuents selected from halo, alkyl, alkylthio, alkylsulfonyl, cyano, trifluoromethyl, or R.sup.2 is pyridinyl, pyrazinyl, quinolinyl, N-alkylpyrrolyl, thienyl, benzothienyl, or furyl; and n is 1 or 2, are cytoprotective anti-ulcer agents.Type: GrantFiled: August 23, 1990Date of Patent: April 23, 1991Assignee: American Home Products Corp.Inventors: Steven W. Felman, Ivo L. Jirkovsky, Kevin A. Memoli
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Patent number: 5010104Abstract: Novel tricyclic compounds having a TXA.sub.2 -antagonizing activity represented by formul (I): ##STR1## which strongly antagonize an action of thromboxane A.sub.2 and are expected to have preventive and therapeutic effects on ischemica diseases, cerebro-vascular diseases, etc.Type: GrantFiled: June 29, 1989Date of Patent: April 23, 1991Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Etsuo Oshima, Hiroyuki Obase, Akira Karasawa, Kazuhiro Kubo, Ichiro Miki, Akio Ishii
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Patent number: 4999429Abstract: Aryl difluoromethyl sulfone adds to aldehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.Type: GrantFiled: November 13, 1989Date of Patent: March 12, 1991Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4990630Abstract: The present invention relates to a 2,3-diaminoacrylonitrile derivative or salts thereof, having the formula ##STR1## wherein R represents an alkyl group (which may be substituted by unsubstituted or substituted phenyl groups, halogen atoms, C.sub.1-6 alkoxycarbonyl groups, carboxy groups, C.sub.1-6 alkoxycarbonyl C.sub.1-6 alkylthio groups, hydroxy groups, mercapto groups, cycloalkyl groups or heterocyclic groups containing oxygen atoms); an alkenyl group; a cycloalkyl group; an aryl group (which may be substituted by halogen atoms, C.sub.1-6 alkyl groups, nitro-groups, unsubstituted or substituted phenyl or phenoxy groups or heterocyclic groups containing oxygen atoms or sulfur atoms).The 2,3-diaminoacrylonitrile derivative can be used as starting materials for the production of pharmaceutical and/or agricultural intermediates such as cyanoimidazoles, cyanopyrazines or other cyano-substituted heterocycles.Type: GrantFiled: August 28, 1989Date of Patent: February 5, 1991Assignee: Nippon Soda Co., Ltd.Inventors: Katsunori Mikuma, Nobuhiro Umeda, Tomio Yagihara, Isami Hamamoto
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Patent number: 4988526Abstract: New hemimercaptals of the formula ##STR1## in which X represents an oxygen or sulphur atom, a process for their preparation and their use as flavorings have been found.Type: GrantFiled: September 13, 1989Date of Patent: January 29, 1991Assignee: Haarmann & Reimer GmbHInventors: Jurgen Bruning, Roland Emberger, Matthias Guntert, Rudolf Hopp, Manfred Kopsel, Theodor Sand, Peter Werkhoff
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Patent number: 4980371Abstract: Furan ketone derivatives thereof having antiretrovirus activity and effective in a method of treatment of a retrovirus infection, have the formula ##STR1## wherein Y is a bond, oxygen or divalent sulfur; n is 0 or 1; R is a straight or branched C.sub.8-20 alkyl chain or a straight or branched C.sub.8-20 alkenyl chain having from 1 to 4 double bonds; and R.sub.1 is C.sub.1-6 alkyl.Type: GrantFiled: November 27, 1989Date of Patent: December 25, 1990Assignee: Merrell Dow PharmaceuticalsInventors: Roger A. Parker, Sai P. Sunkara
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Patent number: 4977185Abstract: Novel furan ketone derivatives having antiretrovirus activity and effective in a method of treatment of a retrovirus infection, have the formula ##STR1## wherein Y represents a bond, oxygen or divalent sulfur; Ar represents phenyl or naphthylenyl; n is 0 or 1; m is an integer of from 4 to 10; and R.sub.1 represents C.sub.1-6 alkyl.Type: GrantFiled: November 27, 1989Date of Patent: December 11, 1990Assignee: Merrell Dow PharmaceuticalsInventors: Roger A. Parker, Sai P. Sunkara
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Patent number: 4962198Abstract: The invention relates to a generally applicable process for the hydroxylation of electrophilic aromatic compounds, according to which the electrophilic aromatic compounds are reacted with organic hydroperoxides in the presence of bases.Type: GrantFiled: July 7, 1989Date of Patent: October 9, 1990Assignee: Bayer AktiengesellschaftInventors: Mieczyslaw Makosza, Krzysztof Sienkiewicz
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Patent number: 4957925Abstract: An aminoalkoxyphenyl compound of formula ##STR1## as well as a pharmaceutically acceptable salt of this compound.Type: GrantFiled: August 7, 1987Date of Patent: September 18, 1990Assignee: SanofiInventors: Jean Gubin, Pierre Chatelain, Marcel Descamps, Dino Nisato, Henri Inion, Jean Lucchetti, Jean-Marie Mahaux, Jean-Noel Vallat
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Patent number: 4946845Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 and R.sup.2 are the same and are lower alkoxy or optionally substituted phenoxy,R.sup.3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2 or R.sup.3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O).sub.n R wherein R is lower alkyl; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or optionally substituted heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2;at least one of X or Y is C(O)W and the other X or Y is different and is hydrogen, C(O)W or R.sup.Type: GrantFiled: November 25, 1988Date of Patent: August 7, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: D. V. Krishna Murthy, Michael C. Venuti, John M. Young
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Patent number: 4935530Abstract: A process for preparing 5-substituted-3-furaldehydes which comprises reacting 3-furaldehyde with lithium morpholide, followed by sec-butyl lithium, followed by an electrophile.Type: GrantFiled: October 18, 1988Date of Patent: June 19, 1990Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 4929738Abstract: Microbicidal substituted pyrazolin-5-ones of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, alkylaminocarbonylalkyl or dialkylaminocarbonylalkyl, or represent in each case optionally substituted oxiranylalkyl, aralkyl, heterocyclyl or aryl andHet represents an optionally substituted heterocyclic radial.Intermediates therefor of the formula ##STR2## in which R is alkyl, are also new.Type: GrantFiled: May 10, 1989Date of Patent: May 29, 1990Assignee: Bayer AktiengesellschaftInventors: Klaus Jelich, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
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Patent number: 4913721Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.Type: GrantFiled: October 31, 1988Date of Patent: April 3, 1990Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey