Spiro Patents (Class 548/216)
  • Patent number: 5508428
    Abstract: 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: Grant
    Filed: April 12, 1995
    Date of Patent: April 16, 1996
    Assignee: Daiichi Phamaceutical Co., Ltd.
    Inventors: Isao Hayakawa, Shohgo Atarashi, Masazumi Imamura, Youichi Kimura
  • Patent number: 5486532
    Abstract: 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: Grant
    Filed: July 19, 1994
    Date of Patent: January 23, 1996
    Assignee: Adir et Compagnie
    Inventors: Alex Cordi, Jean-Michel Lacoste, Michel Laubie, Tony Verbeuren, Jean-Jacques Descombes, Mark Millan
  • Patent number: 5444079
    Abstract: 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: Grant
    Filed: October 19, 1994
    Date of Patent: August 22, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Victor E. Amoo
  • Patent number: 5426192
    Abstract: 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: Grant
    Filed: April 7, 1994
    Date of Patent: June 20, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans Baumann, Ian J. Fletcher
  • Patent number: 5373009
    Abstract: 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: Grant
    Filed: February 2, 1994
    Date of Patent: December 13, 1994
    Assignee: American Home Products Corporation
    Inventors: Thomas J. Commons, Donald P. Strike
  • Patent number: 5369117
    Abstract: 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: Grant
    Filed: August 17, 1993
    Date of Patent: November 29, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfred Sallmann, Hans-Peter Gschwind, Eric Francotte
  • Patent number: 5329006
    Abstract: 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: Grant
    Filed: September 6, 1991
    Date of Patent: July 12, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans Baumann, Ian J. Fletcher
  • Patent number: 5262566
    Abstract: 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: Grant
    Filed: December 10, 1992
    Date of Patent: November 16, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus-Helmut Mohrs, Axel Carstens, Dieter Hoppe
  • Patent number: 5235062
    Abstract: 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: Grant
    Filed: April 9, 1992
    Date of Patent: August 10, 1993
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Alberto Greco, Franco Mizia, Franco Rivetti
  • Patent number: 5225570
    Abstract: 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: Grant
    Filed: July 1, 1988
    Date of Patent: July 6, 1993
    Assignee: Monsanto Company
    Inventors: Eric L. Williams, Steven M. Massey, Brett H. Bussler, Ronald J. Brinker
  • Patent number: 5223616
    Abstract: 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: Grant
    Filed: November 4, 1991
    Date of Patent: June 29, 1993
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Jun Yamamoto, Junichi Sekihachi, Yosuke Yamamoto, Kazuhiro Machiguchi, Yutaka Kayane
  • Patent number: 5223523
    Abstract: Compounds for an methods of controlling plant diseases using thiooxazolidinones, oxazolidindiones and agriculturally suitable compositions containing them are disclosed.
    Type: Grant
    Filed: December 12, 1991
    Date of Patent: June 29, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John B. Adams, Jr., Detlef Geffken, Dennis R. Rayner
  • Patent number: 5196543
    Abstract: 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: Grant
    Filed: July 19, 1991
    Date of Patent: March 23, 1993
    Assignee: Delalande S.A.
    Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
  • Patent number: 5180825
    Abstract: Disclosed in a mitomycin derivative represented by the formula (I): ##STR1## wherein W is a heterocyclic group.
    Type: Grant
    Filed: November 13, 1991
    Date of Patent: January 19, 1993
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Hitoshi Arai, Motomichi Kono, Masaji Kasai, Katsushige Gomi, Tadashi Ashizawa
  • Patent number: 5180419
    Abstract: 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: Grant
    Filed: November 22, 1991
    Date of Patent: January 19, 1993
    Assignee: American Cyanamid Company
    Inventors: David M. Gange, Michael A. Guaciaro, Robert F. Doehner, Jr.
  • Patent number: 5173484
    Abstract: 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: Grant
    Filed: May 14, 1991
    Date of Patent: December 22, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Thomas Schenke, Klaus Grohe, Michael Schriewer, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 5171747
    Abstract: 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: Grant
    Filed: October 16, 1990
    Date of Patent: December 15, 1992
    Assignee: Delalande S.A.
    Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
  • Patent number: 5157108
    Abstract: 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: Grant
    Filed: December 12, 1989
    Date of Patent: October 20, 1992
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Larry R. Krepski, Steven M. Heilmann, Dean M. Moren, Jerald K. Rasmussen
  • Patent number: 5153211
    Abstract: 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: Grant
    Filed: August 27, 1991
    Date of Patent: October 6, 1992
    Assignee: Alcon Laboratories, Inc.
    Inventor: Billie M. York, Jr.
  • Patent number: 5149823
    Abstract: 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: Grant
    Filed: August 9, 1990
    Date of Patent: September 22, 1992
    Assignee: Shell Oil Company
    Inventor: Pen-Chung Wang
  • Patent number: 5140033
    Abstract: 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: Grant
    Filed: October 1, 1990
    Date of Patent: August 18, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Grohe, Andreas Krebs, Uwe Petersen, Thomas Schenke, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 5105009
    Abstract: 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: Grant
    Filed: February 29, 1988
    Date of Patent: April 14, 1992
    Assignee: Zambon S.p.A.
    Inventors: Giancarlo Jommi, Dario Chiarino
  • Patent number: 5103001
    Abstract: 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: Grant
    Filed: January 31, 1991
    Date of Patent: April 7, 1992
    Assignee: Shell Oil Company
    Inventor: Pen-Chung Wang
  • Patent number: 5103007
    Abstract: 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: Grant
    Filed: October 27, 1989
    Date of Patent: April 7, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
  • Patent number: 5095118
    Abstract: 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: Grant
    Filed: April 13, 1990
    Date of Patent: March 10, 1992
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Eike Poetsch, Michael Casutt
  • Patent number: 5087752
    Abstract: 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: Grant
    Filed: September 12, 1990
    Date of Patent: February 11, 1992
    Assignee: Curators of the University of Missouri
    Inventors: Robert W. Murray, Megh Singh
  • Patent number: 5081245
    Abstract: 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: Grant
    Filed: August 18, 1989
    Date of Patent: January 14, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
  • Patent number: 5081197
    Abstract: 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: Grant
    Filed: October 23, 1990
    Date of Patent: January 14, 1992
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Steven M. Heilmann, Dean M. Moren, Jerald K. Rasmussen, Larry R. Krepski, Sadanand V. Pathre
  • Patent number: 5068341
    Abstract: 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: Grant
    Filed: September 5, 1989
    Date of Patent: November 26, 1991
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Eike Poetsch, Michael Casutt
  • Patent number: 5061719
    Abstract: 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: Grant
    Filed: July 20, 1990
    Date of Patent: October 29, 1991
    Assignee: Ube Industries, Ltd.
    Inventors: Hisao Sugiura, Toshinobu Tanaka, Takashi Nishimura, Shuji Yokoyama
  • Patent number: 5055125
    Abstract: 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: Grant
    Filed: April 10, 1990
    Date of Patent: October 8, 1991
    Assignee: Nitrokemia Ipartelepek
    Inventors: Gyorgy Matolcsy, Antal Gimesi, Antalne Tombor, Barna Bordas, Janosne Benczik, Zoltan Kolonics, Csaba Soptei, Sandor Boros, Agota Kener, Denzso Sebok, Geza Szabo, Imre Varga
  • Patent number: 5039813
    Abstract: 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: Grant
    Filed: June 29, 1990
    Date of Patent: August 13, 1991
    Assignee: Polaroid Corporation
    Inventors: Robert C. Fazio, Lloyd D. Taylor
  • Patent number: 5013827
    Abstract: 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: Grant
    Filed: November 13, 1989
    Date of Patent: May 7, 1991
    Assignee: Board of Governors of Wayne State University
    Inventor: Arthur P. Schaap
  • Patent number: 5001233
    Abstract: 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: Grant
    Filed: September 14, 1989
    Date of Patent: March 19, 1991
    Assignee: The Curators of the University of Missouri
    Inventors: Robert W. Murray, Megh Singh
  • Patent number: 4973593
    Abstract: Compounds of the formulae: ##STR1## are useful as anti-hypertensives.
    Type: Grant
    Filed: August 4, 1987
    Date of Patent: November 27, 1990
    Assignee: Research Corporation Technologies, Inc.
    Inventor: Abram N. Brubaker
  • Patent number: 4952707
    Abstract: 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: Grant
    Filed: June 30, 1988
    Date of Patent: August 28, 1990
  • Patent number: 4940703
    Abstract: 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: Grant
    Filed: April 4, 1989
    Date of Patent: July 10, 1990
    Assignee: Merck Sharp & Dohme Limited
    Inventors: Raymond Baker, Clare O. Kneen, John Saunders, Christopher Swain
  • Patent number: 4939270
    Abstract: 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: Grant
    Filed: February 23, 1989
    Date of Patent: July 3, 1990
    Assignee: Shell Oil Company
    Inventor: Pen C. Wang
  • Patent number: 4904300
    Abstract: 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: Grant
    Filed: August 17, 1988
    Date of Patent: February 27, 1990
    Assignee: Ciba-Geigy Corp.
    Inventors: Hans-Dieter Schneider, William R. Lutz, Henry Szczepanski, Werner Topfl
  • Patent number: 4879365
    Abstract: 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: Grant
    Filed: November 14, 1988
    Date of Patent: November 7, 1989
    Assignee: NL Chemicals, Inc.
    Inventors: Glenn H. Petschke, Bernard Taub
  • Patent number: 4871719
    Abstract: 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: Grant
    Filed: March 16, 1988
    Date of Patent: October 3, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Maienfisch
  • Patent number: 4864028
    Abstract: 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: Grant
    Filed: September 9, 1987
    Date of Patent: September 5, 1989
    Assignee: Alcon Laboratories, Inc.
    Inventor: Billie M. York, Jr.
  • Patent number: 4847388
    Abstract: 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: Grant
    Filed: September 16, 1988
    Date of Patent: July 11, 1989
    Assignee: Shell Oil Company
    Inventor: Pen C. Wang
  • Patent number: 4835280
    Abstract: 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: Grant
    Filed: July 14, 1987
    Date of Patent: May 30, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Martens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckman, Klaus Strein, Egon Roesch
  • Patent number: 4824472
    Abstract: 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: Grant
    Filed: December 23, 1987
    Date of Patent: April 25, 1989
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Guy R. E. Van Lommen, Victor Sipido, Wim G. Verschueren, William R. Lutz
  • Patent number: 4753957
    Abstract: 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: Grant
    Filed: September 28, 1981
    Date of Patent: June 28, 1988
    Assignee: Rohm and Haas Company
    Inventor: Hak-Foon Chan
  • Patent number: 4743700
    Abstract: 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: Grant
    Filed: February 1, 1985
    Date of Patent: May 10, 1988
    Assignee: Zambon S.p.A.
    Inventors: Giancarlo Jommi, Dario Chiarino, Roberto Pagliarin
  • Patent number: 4730003
    Abstract: 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: Grant
    Filed: September 4, 1986
    Date of Patent: March 8, 1988
    Assignee: Boehringer Mannheim GmbH
    Inventors: Wolfgang von der Saal, Alfred Mertens, Herbert Berger, Bernd Muller-Beckmann
  • Patent number: 4716113
    Abstract: 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: Grant
    Filed: March 31, 1986
    Date of Patent: December 29, 1987
    Assignee: Pfizer Inc.
    Inventor: Frank J. Urban
  • Patent number: 4698416
    Abstract: 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: Grant
    Filed: June 23, 1986
    Date of Patent: October 6, 1987
    Assignee: Ashland Oil, Inc.
    Inventors: Anil B. Goel, Harvey J. Richards