Spiro Patents (Class 548/216)
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Patent number: 5508428Abstract: A compound of formula I, having antibacterial activity and a pharmaceutical composition containing the compound of formula I: ##STR1## wherein Q represents a partial structure of formula II: ##STR2## wherein all substituents are defined in the specification.Type: GrantFiled: April 12, 1995Date of Patent: April 16, 1996Assignee: Daiichi Phamaceutical Co., Ltd.Inventors: Isao Hayakawa, Shohgo Atarashi, Masazumi Imamura, Youichi Kimura
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Patent number: 5486532Abstract: Compounds of formula (I): ##STR1## in which: X represents --CH.sub.2 --, --(CH.sub.2).sub.2 --, --CH.dbd.CH--, --O--CH.sub.2 --, --S--CH.sub.2 --, --SO--CH.sub.2 -- or --SO.sub.2 --CH.sub.2 --,Y represents oxygen or sulfur or --NR.sub.5 --,R.sub.1 represents halogen, linear or branched (C.sub.1 -C.sub.6) alkyl (unsubstituted or substituted), hydroxyl or linear or branched (C.sub.1 -C.sub.6) alkoxy,R.sub.2 represents hydrogen or halogen, linear or branched (C.sub.1 -C.sub.6) alkyl (unsubstituted or substituted), hydroxyl, linear or branched (C.sub.1 -C.sub.6) alkoxy or linear or branched (C.sub.1 -C.sub.6) alkylthio,R.sub.3 represents hydrogen or halogen, linear or branched (C.sub.1 -C.sub.6) alkyl (unsubstituted or substituted), hydroxyl, linear or branched (C.sub.1 -C.sub.6) alkoxy or linear or branched (C.sub.1 -C.sub.6) alkylthio,R.sub.4 represents hydrogen or amino (unsubstituted or substituted)R.sub.5 represents hydrogen or linear or branched (C.sub.1 -C.sub.6) alkyl,or alternativelyR.sub.1 and R.sub.Type: GrantFiled: July 19, 1994Date of Patent: January 23, 1996Assignee: Adir et CompagnieInventors: Alex Cordi, Jean-Michel Lacoste, Michel Laubie, Tony Verbeuren, Jean-Jacques Descombes, Mark Millan
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Patent number: 5444079Abstract: Arthropodicidal compounds, compositions and methods of use of compounds having formula (I) wherein A, G, Z and R.sup.1 to R.sup.4, are as defined in the text.Type: GrantFiled: October 19, 1994Date of Patent: August 22, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Victor E. Amoo
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Patent number: 5426192Abstract: Chromogenic lactam compounds of the formula ##STR1## in which the ring A is an aromatic or heteroaromatic radical which has 6 ring atoms and may contain a fused aromatic ring, it being possible for both the ring A and the fused ring to be substituted;the ring B is an unsubstituted or substituted benzene ring;Z is ##STR2## O or S; R is hydrogen; unsubstituted or substituted C.sub.1 -C.sub.12 alkyl, cycloalkyl having 5 to 10 carbon atoms; unsubstituted or substituted aryl or aralkyl; C.sub.1 -C.sub.12 acyl; N-(lower alkyl)carbamoyl; or N-arylcarbamoyl which is unsubstituted or substituted on the ring;Q is C.sub.1 -C.sub.12 alkylene, aryl-C.sub.1 -C.sub.4 alkylene, 1,2-cycloalkylene, 1,2- or 1,8-arylene or aralkylene; andX.sub.1 and X.sub.2, independently of one another, are each hydrogen; unsubstituted or substituted alkyl having a maximum of 12 carbon atoms; acyl having 1 to 8 carbon atoms; cycloalkyl having 5 to 10 carbon atoms; or unsubstituted or ring-substituted aralkyl or aryl; or (X.sub.1 and X.sub.Type: GrantFiled: April 7, 1994Date of Patent: June 20, 1995Assignee: Ciba-Geigy CorporationInventors: Hans Baumann, Ian J. Fletcher
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Patent number: 5373009Abstract: A compound of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, independently, halo, trifluoromethyl, cyano, nitro, alkyl, alkoxy, --CO.sub.2 H, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, mono- or di-alkylaminocarbonyl, or mono- or di-alkylaminocarbonyloxy;m is 0, 1 or 2 andR.sup.3 is alkyl;n and p are, independently, 0, 1 or 2;X is O, S or CR.sup.4 R.sup.5,where R.sup.4 and R.sup.5 are, independently, H or alkyl or R.sup.4 and R.sup.5 together with the interposed carbon atom form a 3 to 8 membered carbocyclic ring, are anti-cholesterolemic agents.Type: GrantFiled: February 2, 1994Date of Patent: December 13, 1994Assignee: American Home Products CorporationInventors: Thomas J. Commons, Donald P. Strike
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Patent number: 5369117Abstract: The present invention relates to novel oxazolidines of formula (1) ##STR1## wherein R.sub.1 and R.sub.2 are simultaneously hydrogen or both are the same lower alkyl radical or together are 4- to 7-membered lower alkylene, and to the salts thereof in racemic and chiral form, to the preparation of these novel compounds, to pharmaceutical compositions containing them and to the use thereof as medicaments. The compounds have a stimulating effect on beta-adrenergic receptors and can be used, inter alia, for the treatment of diseases associated with reversible obstruction of the respiratory tract, typically asthma and chronic bronchitis, and also for inflammations of different origin.Type: GrantFiled: August 17, 1993Date of Patent: November 29, 1994Assignee: Ciba-Geigy CorporationInventors: Alfred Sallmann, Hans-Peter Gschwind, Eric Francotte
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Patent number: 5329006Abstract: Chromogenic lactam compounds of the formula ##STR1## in which the ring A is an aromatic or heteroaromatic radical which has 6 ring atoms and may contain a fused aromatic ring, it being possible for both the ring A and the fused ring to be substituted;the ring B is an unsubstituted or substituted benzene ring;Z is ##STR2## R is hydrogen; unsubstituted or substituted C.sub.1 -C.sub.12 alkyl, cycloalkyl having 5 to 10 carbon atoms; unsubstituted or substituted aryl or aralkyl; C.sub.1 -C.sub.12 acyl; N-(lower alkyl)carbamoyl; or N-arylcarbamoyl which is unsubstituted or substituted on the ring;Q is C.sub.1 -C.sub.12 alkylene, aryl-C.sub.1 -C.sub.4 alkylene, 1,2-cycloalkylene, 1,2- or 1,8-arylene or aralkylene; andX.sub.1 and X.sub.2, independently of one another, are each hydrogen; unsubstituted or substituted alkyl having a maximum of 12 carbon atoms; acyl having 1 to 8 carbon atoms; cycloalkyl having 5 to 10 carbon atoms; or unsubstituted or ring-substituted aralkyl or aryl; or (X.sub.1 and X.sub.Type: GrantFiled: September 6, 1991Date of Patent: July 12, 1994Assignee: Ciba-Geigy CorporationInventors: Hans Baumann, Ian J. Fletcher
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Patent number: 5262566Abstract: The invention relates to a process for the preparation of optically active .alpha.-hydroxycarboxylic acids characterised in that carbamates are first reacted in the presence of a selective base and of a chelate-forming diamine to give a carbanion complex compound, this is then dia- or enantioselectively deprotonated, then substituted with CO.sub.2 and, as a final step, the heterocyclic protective group is eliminated.Type: GrantFiled: December 10, 1992Date of Patent: November 16, 1993Assignee: Bayer AktiengesellschaftInventors: Klaus-Helmut Mohrs, Axel Carstens, Dieter Hoppe
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Patent number: 5235062Abstract: New procedure for the preparation of polyoxazolidines which can be defined with the general formula: ##STR1## This procedure, which excludes the use of isocyanates, requires the simple transesterification of the dicarbamate of a diamine with an N-hydroxyalkyloxazolidine.Type: GrantFiled: April 9, 1992Date of Patent: August 10, 1993Assignee: Enichem Synthesis S.p.A.Inventors: Alberto Greco, Franco Mizia, Franco Rivetti
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Patent number: 5225570Abstract: The disclosure herein relates to a new family of haloalkyl oxazolidinyl derivatives as antidotal compounds to reduce injury to crop plants by a variety of herbicides. The antidotal compounds are characterized particularly by having heterocyclyl or spiroheterocyclyl radicals attached to the 5-position of haloalkyl oxazolidine compounds and are especially useful as in-can antidotes against injury by acetanilide and thiocarbamate herbicides to corn, sorghum, soybeans, wheat, rice and other crops.Type: GrantFiled: July 1, 1988Date of Patent: July 6, 1993Assignee: Monsanto CompanyInventors: Eric L. Williams, Steven M. Massey, Brett H. Bussler, Ronald J. Brinker
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Patent number: 5223616Abstract: A heterocyclic compound which is useful for dyeing or printing hydrophobic fiber materials and which has the following formula (I), ##STR1##wherein A.sub.1, A.sub.2, A.sub.3 and A.sub.4 are each hydrogen, halogen, alkyl, alkoxy or alkenyl, X.sub.1 is --O-- or the like, R.sub.1 is a methylene or the like, X.sub.2 is a direct linkage or a divalent group of --O--, --S--, --SO--, --SO.sub.2 --, ##STR2## in which R.sub.3 is a hydrogen atom or a C.sub.1-4 alkyl group, ##STR3## in which R.sub.3 is as defined above, T and u are each independently hydrogen or a C.sub.1-4 alkyl, l is O or an integer of 1 to 3, Q is an unsubstituted or substituted 5-, 6- or 7-membered saturated or unsaturated heterocyclic residue, Y is hydrogen, C.sub.1-4 alkyl, a C.sub.1-4 alkoxy group or the like.Type: GrantFiled: November 4, 1991Date of Patent: June 29, 1993Assignee: Sumitomo Chemical Company, Ltd.Inventors: Jun Yamamoto, Junichi Sekihachi, Yosuke Yamamoto, Kazuhiro Machiguchi, Yutaka Kayane
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Patent number: 5223523Abstract: Compounds for an methods of controlling plant diseases using thiooxazolidinones, oxazolidindiones and agriculturally suitable compositions containing them are disclosed.Type: GrantFiled: December 12, 1991Date of Patent: June 29, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: John B. Adams, Jr., Detlef Geffken, Dennis R. Rayner
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Patent number: 5196543Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is either an oxygen atom, in which case R.sub.2 =H or halogen, or a methylene group or a --CH.dbd.CH-- group, in which case R.sub.2 =H;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group; each of R.sub.3 and R.sub.4 is independently H, C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.5 is H or C.sub.1 -C.sub.4 alkyl;R.sub.6 is C.sub.1 -C.sub.4 alkyl, CHF.sub.2, CF.sub.3, CF.sub.3 CF.sub.2, C.sub.4 -C.sub.7 cycloalkyl, phenyl or benzyl;R.sub.4 and R.sub.6 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --chain;R.sub.5 and R.sub.6 may further form together a --(CH.sub.2).sub.4 --or --(CH.sub.2).sub.5 --chain; andR.sub.7 is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 acyl or benzyl,useful as drugs, prepared by cyclizing N ethoxy carbonyl anilines with substituted 1, 3 dioxolane-2-ones.Type: GrantFiled: July 19, 1991Date of Patent: March 23, 1993Assignee: Delalande S.A.Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
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Patent number: 5180825Abstract: Disclosed in a mitomycin derivative represented by the formula (I): ##STR1## wherein W is a heterocyclic group.Type: GrantFiled: November 13, 1991Date of Patent: January 19, 1993Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Hitoshi Arai, Motomichi Kono, Masaji Kasai, Katsushige Gomi, Tadashi Ashizawa
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Patent number: 5180419Abstract: There are provided o-carboxy-(5-oxo-2-imidazolin-2-yl)benzo-(5-membered)-heterocyclic compounds and derivatives thereof and a method for the use therewith to control monocotyledenous and dicotyledenous plant species.Type: GrantFiled: November 22, 1991Date of Patent: January 19, 1993Assignee: American Cyanamid CompanyInventors: David M. Gange, Michael A. Guaciaro, Robert F. Doehner, Jr.
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Patent number: 5173484Abstract: An antibacterially active quinolone or naphthyridonecarboxylic acid derivative of the formula ##STR1## in which R.sup.1 stands for various organic radical,R.sup.2 stands for hydrogen, alkyl having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl,R.sup.3 stands for hydrogen or amino,R.sup.4 stands for a radical of the formula ##STR2## A stands for N or C-R.sup.5, whereinR.sup.5 stands for hydrogen, halogen methyl, cyano or nitro or else together with R.sup.1 can form a bridge of the structure ##STR3## or a pharmaceutically utilizable hydrate, acid addition salt, alkali metal salt, alkaline earth metal salt, silver salt or guanidinium salt of the carboxylic acid when R.sup.2 is hydrogen.Type: GrantFiled: May 14, 1991Date of Patent: December 22, 1992Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Thomas Schenke, Klaus Grohe, Michael Schriewer, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
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Patent number: 5171747Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is an oxygen atom, a methylene group or a --CH.dbd.CH-- group;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group;D is an oxygen atom or a NOR group, wherein R.dbd.H or C.sub.1 -C.sub.4 alkyl;R.sub.3 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group;each of R.sub.2 and R'.sub.2 independently is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group; andR'.sub.2 and R.sub.3 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain,useful as drugs.Type: GrantFiled: October 16, 1990Date of Patent: December 15, 1992Assignee: Delalande S.A.Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
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Patent number: 5157108Abstract: Compounds containing alpha-amidoacetyle linkages are described that are thermally labile and yield nucleophilic and azlactone products. Nucleophiles are useful as curing agents for epoxy resin sealants and adhesives and azlactones are useful in crosslinking systems for polymers.Type: GrantFiled: December 12, 1989Date of Patent: October 20, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventors: Larry R. Krepski, Steven M. Heilmann, Dean M. Moren, Jerald K. Rasmussen
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Patent number: 5153211Abstract: Disclosed are substituted or unsubstituted planar tricyclic fluorene or nuclear analogs thereof, spiro-coupled to a five-membered ring containing a secondary amide, and the pharmaceutically acceptable salts thereof. These compounds are useful, inter alia in the treatment of diabetes. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when indicated for, inter alia, long term, prophylactic treatment of the diabetes syndrome. A particularly preferred class of compounds comprise difluoro-dialkoxy substituted spiro-(9H-fluorene-9,4'-imidazolidine)-2',5-diones.Type: GrantFiled: August 27, 1991Date of Patent: October 6, 1992Assignee: Alcon Laboratories, Inc.Inventor: Billie M. York, Jr.
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Patent number: 5149823Abstract: A novel class of sulfonamoyl-substituted 1,6-diaza[4.4]spirodilactams, having a sulfonamoyl substituent on the hydrocarbyl group attached to each spiro ring nitrogen atom, is useful for the preparation of polymers, including polyamides and as latent curing agents for epoxy resins.Type: GrantFiled: August 9, 1990Date of Patent: September 22, 1992Assignee: Shell Oil CompanyInventor: Pen-Chung Wang
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Patent number: 5140033Abstract: Antibacterial 5-alkylquinolonecarboxylic acids of the formula ##STR1## in which R.sup.3 is C.sub.1 -C.sub.4 -alkyl,R.sup.1 is optionally substituted alkyl or cycloalkyl, alkenyl, alkoxy, amino or alkylamino or optionally substituted phenyl,R.sup.2 is hydrogen or optionally substituted alkyl,R.sup.4 is a nitrogen-containing heterocyclic radical, andA is hydrogen, halogen, methyl, cyano or nitro, or forms a bridge with R.sup.1.and hydrates and salts thereof.Type: GrantFiled: October 1, 1990Date of Patent: August 18, 1992Assignee: Bayer AktiengesellschaftInventors: Michael Schriewer, Klaus Grohe, Andreas Krebs, Uwe Petersen, Thomas Schenke, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
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Patent number: 5105009Abstract: Intermediates of Formula ##STR1## where R is a methylthio, methylsulfoxy, methylsulfonyl or a nitro group; andX1 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl, phenyl or phenylalkyl(1-6C), where the phenyl ring may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX1 together with X2 is an oxygen atom or an alkylene having from two to five Carbon atoms; orX1 together with X2 and R4 is a chain of formula ##STR2## where p is 3 or 4 and q is 1 or 2; and X2 is hydrogen, 1-6 C alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl or phenyl which may be substituted by one or two halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; orX2 together with R4 is ##STR3## where n is 1 or 2; m is 0 or 1; X is hydrogen, halogen, 1-3 C alkyl, 1-3 C alkoxy or nitro; andX3 is hydrogen or --CO--R4 where R4 is hydrogen, 1-6 alkyl, 1-6 C haloalkyl, 3-6 C cycloalkyl, phenylalkyl(1-6C) or phenyl where the phenyl ring may be substituted by one or two halogen, 1-3 alkyl, 1-3 alkoxy or nitro; andX4 is --OH, fluorine,Type: GrantFiled: February 29, 1988Date of Patent: April 14, 1992Assignee: Zambon S.p.A.Inventors: Giancarlo Jommi, Dario Chiarino
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Patent number: 5103001Abstract: Novel 1,6-diaza [4.4] spirodilactams having heterocyclic-containing substituents on each spiro ring nitrogen atom are produced by reaction of a heterocyclic-substituted primary amine compound and a spirodilactam precursor selected from 4-oxoheptanedioic acid compounds or 1,6-dioxaspiro[4.4]nonane-2,7-dione compounds. The substituted spirodilactam products have a plurality of heterocyclic rings and are useful in biological applications and as stabilizers.Type: GrantFiled: January 31, 1991Date of Patent: April 7, 1992Assignee: Shell Oil CompanyInventor: Pen-Chung Wang
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Patent number: 5103007Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.Type: GrantFiled: October 27, 1989Date of Patent: April 7, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
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Patent number: 5095118Abstract: D-(+)-biotin can be prepared from optically active hydantoins of the formula I ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X and Y have the meaning given in Patent claim 1, in a simple, stereospecific manner. Furthermore bicyclic nitriles of the formula XI ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X and Y have the meaning given represent precious intermediate products and educts of a multitude of possibilities to synthesize optically active D-(+)-biotin.Type: GrantFiled: April 13, 1990Date of Patent: March 10, 1992Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Eike Poetsch, Michael Casutt
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Patent number: 5087752Abstract: The subject invention relates to a method of synthesizing nitroxides from secondary amines. This method uses a suitable dioxirane compound such as dimethyldioxirane (DMD), which is relatively stable and simple to synthesize, as the oxidizing agent. A quantity of a secondary amine having no hydrogen atoms directly attached to the alpha carbon atoms is mixed with a 2x molar ratio of the dioxirane. In a first reaction, the secondary amine is oxidized to form a hydroxylamine; in a second reaction, the hydroxylamine is further oxidized to form a nitroxide. When the dioxirane loses an oxygen atom it converts into a ketone; for example, dimethyldioxirane is converted into acetone. This is very convenient, since the ketone byproduct is a solvent that can be easily removed after the reaction without causing interfering reactions. This method provides a simple, highly selective, rapid reaction with very high yields.Type: GrantFiled: September 12, 1990Date of Patent: February 11, 1992Assignee: Curators of the University of MissouriInventors: Robert W. Murray, Megh Singh
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Patent number: 5081245Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.Type: GrantFiled: August 18, 1989Date of Patent: January 14, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
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Patent number: 5081197Abstract: This invention provides novel azlactone-functional oligomers of 2-alkenyl azlactones in which oligomerization has occurred predominantly via the 2-alkenyl group. Oligomerization of the 2-alkenyl group provides oligomers having 2 to 15 mer units with predominantly carbon-carbon backbone segments. Oligomerized in this fashion, the novel compositions possess azlactone groups which can be reacted with nucleophiles in the normal ring-opening sense. The oligomers are prepared by a novel process in which both Lewis and Bronsted acidic catalysts are effective. The reactive oligomers find utility as crosslinking agents for polymers containing azlactone-reactable nucleophilic groups.Type: GrantFiled: October 23, 1990Date of Patent: January 14, 1992Assignee: Minnesota Mining and Manufacturing CompanyInventors: Steven M. Heilmann, Dean M. Moren, Jerald K. Rasmussen, Larry R. Krepski, Sadanand V. Pathre
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Patent number: 5068341Abstract: Optically active hydantoins of the formula I ##STR1## wherein X, Y, R.sup.1, R.sup.2 and R.sup.3 have the meaning given in Patent claim 1, are useful intermediate products for the preparation of D-(+)-biotin.Type: GrantFiled: September 5, 1989Date of Patent: November 26, 1991Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Eike Poetsch, Michael Casutt
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Patent number: 5061719Abstract: There are disclosed an azolidine derivative represented by the formula: ##STR1## wherein R.sup.1 represents a hydrogen atom, an alkyl group or a cycloalkyl group; R.sup.2 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, an alkenyloxyalkyl group, an alkylthioalkyl group, an alkoxycarbonyl group, a furyl group or a thienyl group, or a phenylalkyl group, a phenoxyalkyl group, a phenylthioalkyl group, a phenylalkyloxyalkyl group, a pyridyloxyalkyl group, a phenoxyphenoxyalkyl group, a benzyloxyphenoxyalkyl group or a pyridyloxyphenoxyalkyl group, or R.sup.1 and R.sup.2 may be combined with each other with carbon atoms bonded thereto to form a group represented by the formula: ##STR2## where R.sup.6 represents a hydrogen atom, a halogen atom or a lower alkyl group; R.sup.Type: GrantFiled: July 20, 1990Date of Patent: October 29, 1991Assignee: Ube Industries, Ltd.Inventors: Hisao Sugiura, Toshinobu Tanaka, Takashi Nishimura, Shuji Yokoyama
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Patent number: 5055125Abstract: Herbicidal compositions comprising a substituted thiolcarbamate derivative corresponding to the formula (I) wherein R.sub.1, R.sub.2 and R.sub.3 are selected independently from alkyl groups having 1 to 4 carbon atoms and/or a chloroacetanilide derivative corresponding to the formula (II) wherein R.sub.4 and R.sub.5 are hydrogen or alkyl group having 1 to 4 carbon atoms, identical or different, R.sub.6 is an alkoxyalkyl group corresponding to the formula --R.sub.7 --O--R.sub.8 in which R.sub.7 and R.sub.8 are selected from alkyl groups having 1 to 4 carbon atoms and, as an antidote, a thiocarbamic acid derivative corresponding to the formula (III) wherein R.sub.9 and R.sub.10 independently from each other are alkyl or alkenyl group having 1 to 4 carbon atoms, or R.sub.9 and R.sub.Type: GrantFiled: April 10, 1990Date of Patent: October 8, 1991Assignee: Nitrokemia IpartelepekInventors: Gyorgy Matolcsy, Antal Gimesi, Antalne Tombor, Barna Bordas, Janosne Benczik, Zoltan Kolonics, Csaba Soptei, Sandor Boros, Agota Kener, Denzso Sebok, Geza Szabo, Imre Varga
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Patent number: 5039813Abstract: Disclosed are certain 2-(4-alkenylphenyl-5-oxazolones useful in the production of polymers containing pendant functional groups obtained by nucleophilic ring-opening addition reactions, the 2-(4-alkenylphenyl)-5-oxazolones having the formula ##STR1## wherein R.sup.1 is hydrogen or alkyl; each of R.sup.2 and R.sup.3 is hydrogen, alkyl, aryl, alkaryl, aralkyl, cycloalkyl, or R.sup.2 and R.sup.3 together with the carbon atom to which they are bonded constitute a carbocyclic or heterocyclic ring.Type: GrantFiled: June 29, 1990Date of Patent: August 13, 1991Assignee: Polaroid CorporationInventors: Robert C. Fazio, Lloyd D. Taylor
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Patent number: 5013827Abstract: Triggerable dioxetanes with a fluorescent molecule containing group bonded or tethered in the dioxetane so as to produce fluorescence from the group are described. The compounds are useful in immunoassays and in probes using enzymes or other chemicals for triggering the dioxetanes to produce light from the fluorescent molecule in the group as a signal.Type: GrantFiled: November 13, 1989Date of Patent: May 7, 1991Assignee: Board of Governors of Wayne State UniversityInventor: Arthur P. Schaap
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Patent number: 5001233Abstract: The subject invention relates to a method of synthesizing hydroxylamines from secondary amines. This method uses a dioxirane compound such as dimethyldioxirane (DMD, which is relatively stable and simple to synthesize), as the oxidizing agent. The reaction proceeds as follows: ##STR1## This method provides a simple, one-step reaction with high yields. It can be performed in acetone solution, and the transferral of an oxygen atom from dimethyldioxirane to the secondary amine converts the dioxirane into acetone, the solvent, permitting simple workup and purification. This method can be used with a wide variety of secondary amines, including aliphatic, aromatic, cyclic, and heterocyclic secondary amines, to create a corresponding variety of hydroxylamines.Type: GrantFiled: September 14, 1989Date of Patent: March 19, 1991Assignee: The Curators of the University of MissouriInventors: Robert W. Murray, Megh Singh
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Patent number: 4973593Abstract: Compounds of the formulae: ##STR1## are useful as anti-hypertensives.Type: GrantFiled: August 4, 1987Date of Patent: November 27, 1990Assignee: Research Corporation Technologies, Inc.Inventor: Abram N. Brubaker
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Patent number: 4952707Abstract: Chemiluminescent 1,2-dioxetane compounds are disclosed in which the molecule is stabilized at the 3-position on the dioxetane ring against decomposition prior to the molecule's coming in contact with a labile group-removing substance (e.g., an enzyme that will cleave the labile group to cause the molecule to decompose to form at least one light-emitting fluorophore) and substituted at the 4-position on the dioxetane ring with a fused polycyclic ring-containing fluorophore moiety bearing a labile ring substituent whose point of attachment to the fused polycyclic ring, in relation to this ring's point(s) of attachment to the dioxetane ring, is such that the total number of ring atoms separating these points of attachment, including the ring atoms at the points of attachment, is an odd whole number. These odd pattern substituted compounds decompose to emit light of greater intensity and of a different wavelength than that emitted by the corresponding even pattern substituted isomers.Type: GrantFiled: June 30, 1988Date of Patent: August 28, 1990
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Patent number: 4940703Abstract: The present invention provides a compound of formula I or a salt or prodrug thereof: ##STR1## wherein the dotted line represents an optional chemical bond in one of the two possible positions;A represents a group of formula II: ##STR2## in which R.sup.1 represents hydrogen, hydroxy, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 alkoxy, benzyloxy, hydroxy (C.sub.1-6)alkyl, halogen, amino, cyano, nitro, --CONR.sup.6 R.sup.7 or --SO.sub.2 NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 independently represent hydrogen, halogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl;R.sup.2 represents hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkylcarbonyl;V represents nitrogen, --CH or --C--; andW represents oxygen, sulphur or --NR.sup.8, in which R.sup.8 represents hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.Type: GrantFiled: April 4, 1989Date of Patent: July 10, 1990Assignee: Merck Sharp & Dohme LimitedInventors: Raymond Baker, Clare O. Kneen, John Saunders, Christopher Swain
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Patent number: 4939270Abstract: Primary diamines, employed in stoichiometric excess, react with a spirodilactam precursor selected from 4-oxoheptandioic acid compounds or 1,6-dioxaspiro[4.4]nonane-2,7-diones, to produce 1,6-diaza[4.4]spirodilactams having an amino-containing substituent on each spiro ring nitrogen atom. The spirodilactams are useful in the production of thermoplastic polyamides by reaction with diacids and as curing agents for epoxy resins in the production of thermoset resins.Type: GrantFiled: February 23, 1989Date of Patent: July 3, 1990Assignee: Shell Oil CompanyInventor: Pen C. Wang
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Patent number: 4904300Abstract: Imidazole derivatives of formula I ##STR1## and the stereochemically isomeric forms thereof, and salts thereof, have useful herbicidal properties. The substituents R.sup.1, L and X have the meanings defined herein.Type: GrantFiled: August 17, 1988Date of Patent: February 27, 1990Assignee: Ciba-Geigy Corp.Inventors: Hans-Dieter Schneider, William R. Lutz, Henry Szczepanski, Werner Topfl
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Patent number: 4879365Abstract: A storage stable one-component air curable urethane coating composition having improved color, abrasion resistance and weather resitance comprising at least twenty percent by weight of resin solids of a compound comprising at least one oxazolidine ring chemically combined from the nitrogen atom of the ring through an alkylene-urethane linking group to a tetramethylxylylenediisocyanate prepolymer radical.The invention also comprises the method for preparing the compound and composition and a method for coating a surface by applying the composition of the invention to the surface and exposing the applied composition to air having a relative humidity of at least 10% and incudes an article coated with the cured composition.Type: GrantFiled: November 14, 1988Date of Patent: November 7, 1989Assignee: NL Chemicals, Inc.Inventors: Glenn H. Petschke, Bernard Taub
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Patent number: 4871719Abstract: Novel 13-spiro-2'-[tetrahydrofuran]-milbemycins of the formula I ##STR1## in which X represents one of the groups --CH(OR.sub.1)--, --C(.dbd.O)-- or --C(.dbd.N--OH)--;R.sub.1 represents hydrogen or a OH-protecting group;R.sub.2 represents methyl, ethyl, isopropyl or sec.-butyl or the group --C(CH.sub.3).dbd.CH--A in which A represents methyl, ethyl or isopropyl; andR.sub.3 represents hydrogen; C.sub.1 -C.sub.10 -alkyl; C.sub.1 -C.sub.10 -alkyl substituted by at least one substituent selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy C.sub.3 -C.sub.9 -alkoxyalkoxyalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.3 -alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, hydroxy, benzyloxy, C.sub.1 -C.sub.6 -acyl and C.sub.1 -C.sub.6 -acyloxy, it being possible for each of the above-mentioned radicals representing or containing an alkoxy group to be terminally substituted at a terminal alkoxy group by hydroxy, halogen, C.sub.1 -C.sub.Type: GrantFiled: March 16, 1988Date of Patent: October 3, 1989Assignee: Ciba-Geigy CorporationInventor: Peter Maienfisch
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Patent number: 4864028Abstract: Disclosed are substituted or unsubstituted planar tricyclic fluorene or nuclear analogs thereof, spiro-coupled to a five-membered ring containing a secondary amide, and the pharmaceutically acceptable salts thereof. These compounds are useful, inter alia, in the treatment of diabetes. Also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when indicated for, inter alia, long term, prophylactic treatment of the diabetes syndrome.Type: GrantFiled: September 9, 1987Date of Patent: September 5, 1989Assignee: Alcon Laboratories, Inc.Inventor: Billie M. York, Jr.
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Patent number: 4847388Abstract: A novel class of unsaturated polycyclic ethers and esters comprises unsaturated ether and ester derivatives of a hydroxyaryl-substituted [4.4] spirodilactams having nitrogen atoms in the 1- and 6-positions of the spiro ring system and having the hydroxyaryl groups attached to each spiro ring nitrogen. Such unsaturated ethers and esters react with conventional curing agents to produce cured, insoluble products having high glass transition temperatures.Type: GrantFiled: September 16, 1988Date of Patent: July 11, 1989Assignee: Shell Oil CompanyInventor: Pen C. Wang
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Patent number: 4835280Abstract: The present invention provides Indolines of the formula: ##STR1## ps useful to provide pharmaceutically active pyrrolobenzimidazoles or tautomers thereof, of the formula: These compounds are useful for treating heart or circulatory diseases, especially those which respond to a change of blood pressure, an increase in cardiac output and/or a change in micro-circulation.Type: GrantFiled: July 14, 1987Date of Patent: May 30, 1989Assignee: Boehringer Mannheim GmbHInventors: Alfred Martens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckman, Klaus Strein, Egon Roesch
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Patent number: 4824472Abstract: Novel herbicidal 1-cyclyl or polycyclyl substituted 1H-imidazole-5-carboxylic acid derivatives, compositions containing these compounds as active ingredients, and a method for controlling weeds, preferably selectively in crops of useful plants. Processes for making these novel compounds.Type: GrantFiled: December 23, 1987Date of Patent: April 25, 1989Assignee: Janssen Pharmaceutica N.V.Inventors: Guy R. E. Van Lommen, Victor Sipido, Wim G. Verschueren, William R. Lutz
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Patent number: 4753957Abstract: This invention relates to substituted 2,4-imidazolidinediones, their method of preparation and use as broad spectrum systemic fungicides effective in controlling phytopathogenic fungi such as barley net blotch (Helminthosporium teres), bean powdery mildew (Erysiphi polygoni), grape downy mildew (Plasmorpora viticola), tomato late blight (Phytophthora infestans), and wheat stem rust (Puccinia graminis f. sp. tritici race 15 B-2.Type: GrantFiled: September 28, 1981Date of Patent: June 28, 1988Assignee: Rohm and Haas CompanyInventor: Hak-Foon Chan
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Patent number: 4743700Abstract: Replacement with fluorine of the primary hydroxy group of 1-phenyl-2-amino-1,3-propanediol compounds wherein the secondary hydroxy group and the amino group have been suitably protected.The reaction is carried out with an inorganic fluoride in a polyglycol.New oxazoline compounds particularly useful in said process.Type: GrantFiled: February 1, 1985Date of Patent: May 10, 1988Assignee: Zambon S.p.A.Inventors: Giancarlo Jommi, Dario Chiarino, Roberto Pagliarin
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Patent number: 4730003Abstract: The present invention provides compounds of the general formula: ##STR1## wherein the various substituents are defined hereinbelow. The compounds are used for the treatment and/or prophylaxis of heart and circulatory diseases.Type: GrantFiled: September 4, 1986Date of Patent: March 8, 1988Assignee: Boehringer Mannheim GmbHInventors: Wolfgang von der Saal, Alfred Mertens, Herbert Berger, Bernd Muller-Beckmann
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Patent number: 4716113Abstract: An improved process for preparing (4S)-6-fluoro-spiro-[chroman-4,4'-imidazolidine]-2',5'-dione (sorbinil) or its (2R)-methyl derivative (2-methylsorbinil) is disclosed herein, starting from p-fluorophenol in each instance. The final products obtained have known pharmaceutical value as agents for the control of certain chronic diabetic complications. Key steps concerned with the process involve converting p-fluorophenol into the appropriate .beta.-(4-fluorophenoxy)alkane halide, followed by amidoalkylation with N-benzoyl or N-(lower alkanoyl)-.alpha.-hydroxyglycine to form an intermediate 2-amidoalkylated derivative thereof, and then dehydration and spiroalkylation of said intermediate by treatment with a dehydrating agent and a base to yield a spiroalkylated azlactone compound.Type: GrantFiled: March 31, 1986Date of Patent: December 29, 1987Assignee: Pfizer Inc.Inventor: Frank J. Urban
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Patent number: 4698416Abstract: The process for preparing novel polymers by the reaction of a bicyclic amide acetal with sulfur at a temperature in the range of from about 25.degree. C. to about 200.degree. C. is described.Type: GrantFiled: June 23, 1986Date of Patent: October 6, 1987Assignee: Ashland Oil, Inc.Inventors: Anil B. Goel, Harvey J. Richards