Carbon To Carbon Unsaturation Between Ring Members Of The Five-membered Hetero Ring (e.g., Maleimide, Etc.) Patents (Class 548/548)
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Patent number: 5310536Abstract: Amide-thiolate ligands having improved metal chelate formation kinetics are disclosed. The ligands include a tertiary amine strategically located to facilitate rapid formation of an amine-amide-thiolate intermediate complex, followed by transfer of the metal to a thermodynamically stable amide-thiolate complex. The amide-thiolate ligands of the present invention may be used for post formed labeling of biological substances for use in the fields of diagnosis and therapy.Type: GrantFiled: February 6, 1992Date of Patent: May 10, 1994Assignee: Mallinckrodt Medical, Inc.Inventor: Ananthachari Srinivasan
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Patent number: 5306828Abstract: In a process for the preparation of substituted maleimides the corresponding amines are reacted with maleic anhydride and the thermal imidization of the resulting substituted amic-acids is effected in a mixed apolar/polar aprotic solvent medium in the presence of an acid catalyst, a substantial portion of the apolar solvent is subsequently selectively removed from the reaction mixture and most of the final product is precipitated.Type: GrantFiled: February 13, 1992Date of Patent: April 26, 1994Assignee: Bromine Compounds Ltd.Inventors: Michel Adda, Chaim Eidelman, Leonard Shorr
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Patent number: 5292873Abstract: A sequence directed reagent is constructed by conjugating a methyl naphthoquinone derivative to a hexamethylamino linker attached to the 5' terminus of an oligonucleotide. Annealing this modified fragment of DNA to its complementary sequence allows for target modification subsequent to photochemical activation. The product of this reaction is a covalent crosslink between the reagent and target strands resulting from an alkylation of DNA by the photoexcited quinone. The modified sequence is not labile to acid, base or reductants, and blocks the exonuclease activity of the Klenow fragment of DNA polymerase I. In another embodiment, a highly reactive moiety, such as Br is attached to the methyl group of the naphthoquinone derivative. This reagent is similarly linked to an oligonucleotide probe. Activation of this probe linked alkylating agent is by a reductive signal which may either naturally occur within the cell, such as an enzyme, or introduced into the media containing the target molecule.Type: GrantFiled: November 29, 1989Date of Patent: March 8, 1994Assignee: The Research Foundation of State University of New YorkInventors: Steven E. Rokita, Moneesh Chatterjee
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Patent number: 5274119Abstract: A group of functionalized linking agents are disclosed. The linking agents contain thiol reactive functionalities for the covalent reaction with sulfhydryl groups from the hinge-region of antibody fragments. The linking agents also contain masked aldehyde functionalities for covalent attachment of amine-containing therapeutic agents by Schiff base formation. Carrier systems capable of delivering compounds to targeted sites in vivo based on antigen-antibody interactions are constructed from these linking agents.Type: GrantFiled: April 1, 1991Date of Patent: December 28, 1993Assignee: The Dow Chemical CompanyInventors: Kevin A. Frazier, Margaret E. Schott
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Patent number: 5264586Abstract: Chimeric analogs of calicheamicin that include an analog of calicheamicinone linked to an ester or glycoside, (-)-calicheamicinone and its analogs are disclosed.Type: GrantFiled: July 16, 1992Date of Patent: November 23, 1993Assignee: The Scripps Research InstituteInventors: Kyriacos C. Nicolaou, Adrian L. Smith, Chan-Kou Hwang, Emmanuel Pitsinos
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Patent number: 5262514Abstract: Substituted and unsubstituted di-phthalonitrile monomers devoid of ether /or phenoxy groups are solid at room temperature and which monomers are defined by the following general formula: ##STR1## where R is an aromatic tetravalent radical, thermoplastic prepolymers and thermosetting polymers which polymers are solid at room temperature and have a defined glass transition temperature if said polymers are cured at a temperature below a critical temperature or are devoid of a glass transition temperature if said polymers are postcured at a temperature exceeding said critical temperature.Type: GrantFiled: March 12, 1992Date of Patent: November 16, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
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Patent number: 5250702Abstract: A compound of the formula II: ##STR1## wherein n is an integer of 2 to 10,A' is a bivalent linking group formed by reacting both the reactive groups of a cross linking reagent, andB is a residue of a polypeptide compound,and physiologically acceptable salts thereof are disclosed. Such compound is useful as a non-radioactive carrier for radioactive metal elements.Type: GrantFiled: April 26, 1991Date of Patent: October 5, 1993Assignee: Nihon Medi-Physics Co., Ltd.Inventors: Susumu Kondo, Miki Kurami, Makoto Azuma
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Patent number: 5242680Abstract: Novel thiol-reactive maleimido-based radiolabeling reagents are disclosed which are useful for binding and receptor studies and assays. The reagents are also useful as diagnostic imaging agents, and as radiotherapeutic drugs.Type: GrantFiled: August 23, 1991Date of Patent: September 7, 1993Assignee: Merck & Co., Inc.Inventor: Michael Chorev
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Patent number: 5206370Abstract: Bifunctional aromatic compounds which are capable of linking metal ions to biologically useful molecules. The bifunctional compounds are characterized as having a hydrazine or hydrazide group and a protein reactive group. The hydrazine or hydrazide group may be protected as a lower alkyl hydrazone. Conjugates of the bifunctional compounds with macromolecules are also described and labelled macromolecules comprised of the conjugates and metal ions are provided. Additionally, a method is provided for forming a labelled macromolecule by reacting a conjugate with a metal species The compounds and method of this invention are particularly useful in the fields of biology and medicine for imaging and/or therapy.Type: GrantFiled: May 26, 1992Date of Patent: April 27, 1993Assignee: Johnson Matthey, Inc.Inventors: David A. Schwartz, Michael J. Abrams, Christen M. Giadomenico, Jon A. Zubieta
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Patent number: 5204366Abstract: 2,5-Dioxo-3-pyrroline-1-acetanilide compounds which are effective for the control or prevention of phytopathogenic fungi are described. A method for the fungicidal use of said compounds, fungicidal compositions containing said compounds and a method for the preparation of said compounds are also presented.Type: GrantFiled: June 10, 1991Date of Patent: April 20, 1993Assignee: American Cyanamid CompanyInventors: Jerome M. Lavanish, Bomi Patel
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Patent number: 5196550Abstract: The present invention is directed to a reactive diluent comprising a backbone portion and a pendant group portion. The backbone portion comprises at least two polymerizable sites, and the pendant group portion comprising a functional group having the following formula: ##STR1## wherein Z is an ethylenically unsaturated hydrocarbyl or substituted hydrocarbyl group containing from 2 to about 12 carbon atoms and wherein said pendant group is capable of a (2+2) cyclo-addition with another like pendant group of the above formula. The chain extending reaction site is preferably used in a polymerization reaction to provide a polymeric material, and the cross-linking reactive site is preferably used to create cross-linking as needed or desired.Type: GrantFiled: April 30, 1990Date of Patent: March 23, 1993Assignee: The B. F. Goodrich CompanyInventors: Carl J. Long, II, William F. Masler, William R. Wilbur, Gary L. Julian, Julius Farkas
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Patent number: 5180816Abstract: A one vial method for labeling a protein, such as an antibody or antibody fragment, with a radiometal such as Tc-99m or a rhenium isotope, is disclosed. The method comprises contacting in a single vial a mixture comprised of a reducing agent and a protein molecule covalently bound to a sulfhydryl containing bifunctional coupling agent with Tc or Re in an oxidized state. A one vial kit for labeling a protein with Tc or Re is also disclosed.Type: GrantFiled: August 24, 1988Date of Patent: January 19, 1993Assignee: CentocorInventor: Richard T. Dean
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Patent number: 5175257Abstract: Chelating compounds of specified N.sub.2 S.sub.2 N.sub.3 S derived structure are useful for radiolabeling targeting molecules such as antibodies. Cleavable ester orthioester linkers connect the radionuclide metal chelates to the antibodies. The radiolabeled antibodies have improved biodistribution properties, including reduced localization within the intestines and kidneys.Type: GrantFiled: January 14, 1991Date of Patent: December 29, 1992Assignee: NeoRx CorporationInventors: Sudhakar Kasina, Ananthachari Srinivasan, John M. Reno, Linda M. Gustavson, Jeffrey N. Fitzner, David S. Jones
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Patent number: 5175309Abstract: A process for the preparation of N-substituted maleimides by conducting heat-dehydration and dehydrating imidization of N-substituted maleamic acids under azeotropic distillation of generated water in a solvent mixture containing a solvent capable of forming water azeotrope and an organic aprotic polar solvent, in the presence as catalyst of a zinc salt of a maleamic acid, metallic zinc or a zinc compound which forms a zinc salt of the N-substituted maleamic acid in the reaction system.Type: GrantFiled: December 8, 1989Date of Patent: December 29, 1992Assignee: Mitsui Toatsu Chemicals Inc.Inventors: Ryuichiro Tsumura, Kunimitsu Fukumura, Teruo Muraishi
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Patent number: 5175069Abstract: A thermally-transferred color filter array element comprising a support having thereon a polymeric dye image-receiving layer containing a thermally-transferred image comprising a repeating pattern of colorants of a maleimide blue dye having the formula: ##STR1## wherein: R.sup.1 and R.sup.2 each independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 8 carbon atoms; a cycloalkyl group having from about 5 to about 8 carbon atoms; or a substituted or unsubstituted alkenyl group having from about 2 to about 8 carbon atoms;R.sup.1 and R.sup.2 may represent the elements which may be taken together to form a 5- or 6-membered heterocyclic ring;each Y independently represents hydrogen; a substituted or unsubstituted alkyl group having from 1 to about 8 carbon atoms; an alkoxy group OR.sup.Type: GrantFiled: June 14, 1991Date of Patent: December 29, 1992Assignee: Eastman Kodak CompanyInventors: Leslie Shuttleworth, Helmut Weber
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Patent number: 5149827Abstract: A method for handling a maleimide, which method comprises handling said maleimide in the presence of a stabilizer at a temperature exceeding the melting point thereof in a state kept in contact with a gas phase having a molecular oxygen content of not more than 10% by volume.Type: GrantFiled: January 8, 1991Date of Patent: September 22, 1992Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Yuichi Kita, Kazuo Kishino, Hiroko Ueda
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Patent number: 5145984Abstract: A process for producing a lubricating oil dispersant additive comprises:step (1) reacting compound (A), wherein compound (A) is a hydrocarbyl-substituted or a substituted hydrocarbyl-substituted succinic acid or anhydride or ester thereof, with compound (B) of formula (I)H.sub.2 N(CHR.sup.1 CHR.sup.2 O).sub.n CHR.sup.3 CHR.sup.4 NH.sub.2 (I)wherein one R.sup.2 and R.sup.2 is hydrogen and the other is hydrogen or a lower alkyl group and n is an integer from 1 to 10 and one of R.sup.3 and R.sup.4 is hydrogen and the other is hydrogen or a lower alkyl group, each of the --(CHR.sup.1 CH.sup.2 O)--units being independently defined, to give a product (C) andstep(2) reacting product (C) with a diisocyanate (D) of formula (II)OCN--R.sup.5 --NCO (II)wherein R.sup.5 is a divalent organic group. Novel succinimides have been prepared by the disclosed process, lubricating oil compositions comprise 1-20% w/w of the modified succinimdes. The succinimides have dispersancy and VI improver properties.Type: GrantFiled: September 17, 1990Date of Patent: September 8, 1992Assignee: BP Chemicals (Additives) LimitedInventor: Stephen J. Cook
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Patent number: 5143953Abstract: Thermal stability of vinyl halide polymers is enhanced by the use of dienophiles such as N-alkyl maleimides, and bis compounds thereof, disclosed herein. The maleimides and bis compounds thereof produce synergistic results in terms of thermal stability of vinyl halide polymers when used in conjunction with conventional metal-containing thermal stabilizers. Environmental concerns are abated and certain other advantages are realized if the maleimides disclosed herein are used in conjunction with conventional nonmetallic thermal stabilizers to stabilize vinyl halide polymers against heat deterioration. Bis compounds of the N-alkyl maleimides disclosed herein, when used as thermal stabilizers for vinyl halide polymers, promote crosslinking without degrading the vinyl halide polymer.Type: GrantFiled: December 28, 1990Date of Patent: September 1, 1992Assignee: The B. F. Goodrich CompanyInventor: Naser Pourahmady
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Patent number: 5144043Abstract: A bifunctional coupling agent for joining a sulfhydryl containing protein or peptide and a metallic radionuclide comprising a sulfhydryl selective electrophile, a chelator containing at least one protected thiol and a organic linking radical containing at least one cleavable site which serves to join said electrophile and said chelator is disclosed. A radiodiagnostic or radiotherapeutic precursor comprising an antibody or antibody fragment and the specified bifunctional coupling agent bound to a sulfhydryl group on the antibody or antibody fragment and a radiodiagnostic or radiotherapeutic agent comprising such precursor having a metallic radionuclide bound thereto are also disclosed.Type: GrantFiled: August 24, 1988Date of Patent: September 1, 1992Assignee: CentocorInventors: Richard T. Dean, Raymond H. Boutin, Robert W. Weber
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Patent number: 5136052Abstract: A process for the manufacture of N-phenylmaleimide which comprises reacting maleic anhydride with aniline in a single step at elevated temperature in the presence of a water-immiscible organic solvent capable of forming an azeotrope with water and of p-toluenesulfonic acis as catalyst.Type: GrantFiled: May 29, 1991Date of Patent: August 4, 1992Assignee: U C B, S.A.Inventors: August Van Gysel, Ivan Vanden Eynde, Jean-Claude Vanovervelt
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Patent number: 5132431Abstract: A process for the continuous preparation of imidoperoxycarboxylic acids of the formula ##STR1## in which A is C.sub.2 -C.sub.4 -alkylene, phenylene, naphthylene or a group of the formula ##STR2## and R is a group of the formula --COOH, --SO.sub.3 H or --Cl, and X is C.sub.1 -C.sub.19 -alkylene or arylene, in which a solution of imidocarboxylic acids of the formula ##STR3## in sulfuric acid or methanesulfonic acid and an aqueous solution of hydrogen peroxide are continuously metered into a static mixer, then the solution of the imidoperoxycarboxylic acid obtained in this way is treated with water and the precipitated product is isolated.Type: GrantFiled: February 1, 1991Date of Patent: July 21, 1992Assignee: Hoechst AktiengesellschaftInventors: Hermann Fuchs, Hanspeter Gethoffer, Walter Gilb
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Patent number: 5130378Abstract: The present invention relates to copolymers prepared from olefinically unsaturated compounds, having a molecular weight (M.sub.n) of 600 to 20,000 and containing 0.1 to 6.0% by weight of secondary amino groups, --NH--, in the form of structural units corresponding to formula I ##STR1## wherein R.sub.1 is a saturated aliphatic hydrocarbon radical containing 2 to 6 carbon atoms, provided that at least two carbon atoms are arranged between the two nitrogen atoms, andR.sub.2 is a methyl, ethyl or 2-hydroxyethyl group.The present invention also relates to a process for the production of these copolymers.Type: GrantFiled: August 28, 1990Date of Patent: July 14, 1992Assignee: Bayer AktiengesellschaftInventors: Harald Blum, Josef Pedain, Christian Wamprecht
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Patent number: 5128484Abstract: The present invention is directed to an acrylonitrile maleimides solution composition of highly desirable shelf like, having the acid component in said acrylonitrile maleimides soltuion adjusted to a level of no more than 0.1% by weight based on the amount of said maleimides contained in said solution and having a polymerization inhibitor in said solution adjusted to a level in the range of 0.0001 to 1% by weight based on the amount of said solution, and a method for the production thereof.Type: GrantFiled: December 27, 1988Date of Patent: July 7, 1992Assignee: Sokubai Kagaku Kogyo, Co., Ltd.Inventors: Yuichi Kita, Kazuo Kishino, Masakazu Nakagawa, Hitoshi Kanei, Kentaro Sakamoto, Takeshi Okuno
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Patent number: 5112953Abstract: Chelating compounds of specified structure are useful for radiolabeling targeting molecules such as antibodies. Cleavable linkers connect the radionuclide metal chelates to the antibodies. The radiolabeled antibodies have improved biodistribution properties, including reduced localization within the intestines and kidneys.Type: GrantFiled: December 29, 1989Date of Patent: May 12, 1992Assignee: NeoRx CorporationInventors: Linda M. Gustavson, Ananthachari Srinivasan, Sudhakar Kasina, John M. Reno, Jeffrey N. Fitzner, David S. Jones
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Patent number: 5112989Abstract: A process for producing an unsaturated dicarboxylic acid imide compound of formula (I): ##STR1## wherein D represents a divalent organic group having at least one carbon/carbon double bond; R.sup.1 represents an n-valent organic group having at least one carbon atom; and n is an integer of 1 or above, which comprises reacting an unsaturated amide acid compound of formula (II): ##STR2## wherein D, R.sup.1, and n are as defined above, with an orthoester of formula (III): ##STR3## wherein R.sup.2 and R.sup.3, which may be the same or different, each represents a monovalent organic group having at least one carbon atom, to form an unsaturated dicarboxylic acid amide acid ester compound of formula (IV): ##STR4## wherein D, R.sup.1, R.sup.3, and n are as defined above, and then imidating the compound of formula (IV).Type: GrantFiled: March 20, 1989Date of Patent: May 12, 1992Assignee: Matsushita Electric Works Ltd.Inventors: Tatsuo Yonemoto, Eiichiro Saito, Masahiro Matsumura
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Patent number: 5091407Abstract: Fungicidally active compounds of the formula ##STR1## and steroisomers thereof, wherein A is the group .dbd.CW--or a nitrogen atom, B is the group .dbd.CX--or a nitrogen atom, D is the group .dbd.CY--or a nitrogen atom, and E is the group .dbd.CZ--or a nitrogen atom, wherein W, X, Y and Z, which may be the same or different, are, for example, hydrogen, halogen, nitro, nitrile, or other defined groups and wherein R.sup.1 and R.sup.2 are alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted aralkyl, cycloalkyl groups, or optionally substituted heteroaromatic, and V is oxygen or sulfur.Type: GrantFiled: November 24, 1989Date of Patent: February 25, 1992Assignee: Imperial Chemical Industries PLCInventors: Paul deFraine, Brian K. Snell, Kevin Beautement, Vivienne M. Anthony, John M. Clough
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Patent number: 5075488Abstract: A soil disease controlling agent for preventing and controlling diseases caused by pathogenic fungi living in soil, which comprises an effective amount of at least one of a 2-cycloalkenylamine derivative and its salts as an active ingredient, and at least one inert carrier or diluent.Type: GrantFiled: June 25, 1987Date of Patent: December 24, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroki Tomioka, Tadashi Ooishi, Junya Takahashi, Mitsuru Sasaki, Naonori Hirata
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Patent number: 5068356Abstract: Phenolic N-(amido) imides are provided which are useful as antioxidant stabilizers for organic materials, including a large variety of synthetic polymers, typically subject to thermooxidative degradation. The antioxidant effectiveness of the phenolic N-(amido)imide stabilizers is enhanced by the deactivating potential of the amido-imide moiety towards metals or metal ions that frequently contaminate polymer compositions and serve to catalyze thermal degradation.Type: GrantFiled: February 20, 1990Date of Patent: November 26, 1991Assignee: Atochem North America, Inc.Inventor: Jerome Wicher
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Patent number: 5068357Abstract: A process for the preparation of N-substituted maleimides by conducting heat-dehydration and dehydrating imidization of N-substituted maleamic acids under azeotropic distillation of generated water in a solvent mixture containing a solvent capable of forming water azeotrope and an organic aproptic polar solvent, in the presence as catalyst of metallic tin, tin oxide, a tin salt of a maleamic acid or a tin compound which forms a thin salt of the N-substituted maleamic acid in the reaction system.Type: GrantFiled: June 11, 1990Date of Patent: November 26, 1991Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ryuichiro Tsumura, Teruo Muraishi, Keiichi Ideda, Jin-Kai Wang
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Patent number: 5039696Abstract: A maleimide derivative useful as an active agent for a fungicide for agriculture and horticulture, having the formula (I): ##STR1## wherein X and Y each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group, a lower alkoxy group, an aralkyloxy group or a trifluoromethyl group,Z represents a chlorine atom or bromine atom,and R represents a straight or branched alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkynyl group having 2 to 5 carbon atoms, an alkoxyalkyl group having 2 to 5 carbon atoms, an oxoalkyl group having 3 to 6 carbon atoms or a phenyl group or a phenyl alkyl group which may be substituted.Type: GrantFiled: February 1, 1990Date of Patent: August 13, 1991Assignee: Suntory LimitedInventors: Shinjiro Niwata, Harukazu Fukami, Masaki Hashimoto, Norio Ohtsuka, Fumio Fujita
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Patent number: 4987130Abstract: Substituted amino derivatives represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 each stand for an acyclic hydrocarbon residue or an alicyclic hydrocarbon residue; R.sup.3 and R.sup.4 each stand for hydrogen or a hydrocarbon residue optionally containing hetero-atom(s); A stands for a carbon chain having two or more carbon atoms optionally containing ether linkage or sulfide linkage, which may be substituted and which may per se form a ring; X.sup.1 and X.sup.2 each stand for oxygen atom or sulfur atom; and Y stands for amino group or an organic residue bonded through nitrogen atom, which may form a ring by combining with a carbon atom constituting A; and their salts have anti-arrhythmic activity and are useful for prevention and treatment of a variety of arrhythmias.Type: GrantFiled: December 22, 1989Date of Patent: January 22, 1991Assignee: Takeda Chemical Industries, Ltd.Inventors: Susumu Tsushima, Muneo Takatani, Minoru Hirata
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Patent number: 4980483Abstract: A method for the production of a maleimide, which comprises effecting a former-stage reaction by adding maleic anhydride and a primary amine in amounts such that the molar ratio of said maleic anhydride to said primary amine is less than 1 under application of heat to a water-insoluble or water-immisible inert organic solvent containing an acid catalyst and subsequently carrying out a latter-stage reaction by adding to the reaction system maleic anhydride in an amount such that the molar ratio of the total amount of maleic anhydride to be added to said reaction system to the total amount of said primary amine added to said reaction system exceeds 1.Type: GrantFiled: February 14, 1989Date of Patent: December 25, 1990Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Yuichi Kita, Masakazu Nakagawa, Hitoshi Kanei, Akio Fukui
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Patent number: 4980482Abstract: A process for the preparation of activated esters of certain N-maleoyl amino acids is disclosed. In the process, maleamic acids are cyclized and esterified to the desired products by the initial reaction with an acid halide reagent followed by a subsequent reaction with the appropriate hydroxyl-containing compound. The activated esters of N-maleoyl amino acids are particularly suited for linking compounds containing an amino group with those containing a thiol group.Type: GrantFiled: January 19, 1988Date of Patent: December 25, 1990Assignee: The Dow Chemical CompanyInventor: Kevin A. Frazier
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Patent number: 4968321Abstract: A motor fuel composition which inhibits engine ORI and intake valve deposit formation and sticking comprises a mixture of hydrocarbons boiling in the range of 90.degree. F.-450.degree. F. and (I) the reaction product of a hydrocarbyl-substituted dibasic acid anhydride and a polyoxyalkylene diamine; (II) a polymeric component which is a polyolefin polymer, copolymer, or the corresponding aminated or hydrogenated polymer or copolymer, or mixtures thereof, of a C.sub.2 -C.sub.10 hydrocarbon; (III) a polyalkylene glycol having a molecular weight in the range of 500-2000; and (IV) a lubricating oil composition.Type: GrantFiled: February 6, 1989Date of Patent: November 6, 1990Assignees: Texaco Inc., Texaco Technology Europe GmbHInventors: Rodney L. Sung, Daniel T. Daly, Thomas E. Hayden, Rolf Sieverding
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Patent number: 4957537Abstract: The present invention discloses a new plant growth regulating composition which comprises, as an active ingredient, a selected succinamide compounds, maleimide compounds, succinic anhydride compounds, maleic anhydride compounds of general formula: ##STR1## if preferably, along with ethephon. In this invention, the plant growth regulating composition has the effect of plant growth controlling activity (herbicidal activity) and an abscission layer forming activity for a fruit harvest aid, and the said plant growth regulating composition does not cause hazards such as defoliation and injuries to the fruit surface, nor does it affect immature fruit, but acts specifically on matured fruit and promptes formation of abscission layer that aids in the separation of matured fruit.Type: GrantFiled: March 22, 1988Date of Patent: September 18, 1990Assignees: Fujisawa Pharmaceutical Company, Ltd, Nissan Chemical Industries, Ltd.Inventors: Tsutomu Teraji, Atsushi Yamamura, Yasuo Kamuro, Koichi Hirai, Seiichi Fujii
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Patent number: 4954638Abstract: Leukotrienes may be conjugated with various proteins such as Bovine Serum Albumin (BSA) and Hemocyanin from Giant Keyhole Limpets (KLH) using 1,5-difluoro-2,4-dinitrobenzene or 6-N-maleimidohexanoic acid chloride as coupling agents.These conjugates are useful as reagents in a newly developed immunoassay for leukotrienes, as well as having potential utility as chemical immunotherapeutic agents in the treatment of various allergic and chronic inflammatory diseases of the skin, lung, and airways, including asthma, allergic rhinitis, rheumatoid arthritis, and skin diseases such as psoriasis and eczema.Type: GrantFiled: August 1, 1988Date of Patent: September 4, 1990Assignees: Merck Frosst Canada, Inc., Merck & Co., Inc.Inventors: Robert N. Young, Joshua Rokach, Edward C. Hayes
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Patent number: 4945104Abstract: A maleimide derivative having the formula (I): ##STR1## wherein R.sub.1 represents a lower alkyl group having 1 to 4 carbon atoms, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 independently represent a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a phenyl group which may be substituted, or an aralkyl group having 7 to 10 carbon atoms, and X.sub.1 and X.sub.2 independently represent a hydrogen atom or a halogen atom, and a production process thereof as well as a agricultural and horticultural fungicide containing, as an active ingredient, the maleimide derivative.Type: GrantFiled: June 23, 1989Date of Patent: July 31, 1990Assignee: Suntory LimitedInventors: Harukazu Fukami, Masaki Hashimoto, Shinjiro Niwata, Norio Ohtsuka, Fumio Fujita
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Patent number: 4933425Abstract: An aromatic polycarbonate containing at least one terminal group represented by the formula ##STR1## wherein R and R' are the same or different and are alkyl, aryl or halogen; a and b are the same or different and are zero or an integer of one to four; W is 0, S, SO, SO.sub.2, CH.sub.2, CHR or CR.sub.2 wherein R is identified above: ##STR2## Preferably a and b are the same or different and are zero or one, more preferably each is zero. W is CH.sub.2, CHR or CR.sub.2.Type: GrantFiled: August 15, 1988Date of Patent: June 12, 1990Assignee: General Electric Co.Inventor: Robert R. Gallucci
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Patent number: 4906252Abstract: This invention is to a fuel oil composition containing polyolefinic succinimide polyamine alkyl acetoacetate adducts of the general following: ##STR1## wherein the variables are defined herein. The adduct additives are especially useful in concentrates and fuel oil compositions as dispersants. The formulations have excellent cold flow properties compared to similar formulations not containing the inventive adduct.Type: GrantFiled: April 7, 1989Date of Patent: March 6, 1990Assignee: Exxon Chemical Patents Inc.Inventors: Antonio Gutierrez, Robert D. Lundberg, Robert A. Kleist, Ricardo Bloch
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Patent number: 4904803Abstract: N-substituted maleimides are prepared by reacting maleic anhydride with an amine in the presence of Cu or a copper compound and purifying the maleimide produced in the absence of presence of said Cu or copper compound. N-substituted maleimides are widely useful or starting materials or intermediates for medicines, agricultural chemicals, dyes, macromolecular compounds, and the like.Type: GrantFiled: February 16, 1989Date of Patent: February 27, 1990Assignees: Nitto Chemical Industry Co., Ltd., Mitsubishi Rayon Co., Ltd.Inventors: Takeyuki Fujita, Tuyoshi Irie, Yasuyuki Takayanagi, Takeshi Narita, Yuya Yano
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Patent number: 4886911Abstract: The invention concerns compounds of formula I ##STR1## wherein: X and Y are independently selected from the group consisting of hydrogen, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl, and the group wherein X and Y together from a three or four-membered carbon bridge the bridge optionally comprising one or both of a double bond and a carbonyl group;Z is selected from the group consisting of hydrogen, halogen, C.sub.1 to C.sub.4 alkyl and C.sub.1 to C.sub.4 alkanoyl;R.sup.1 is selected from the group consisting of: hydrogen; an acyl group; and an inorganic or organic cation;R.sup.2 is selected from the group consisting of: C.sub.1 to c.sub.6 alkyl; C.sub.2 to C.sub.6 alkenyl; C.sub.2 to C.sub.6 haloakenyl; C.sub.2 to C.sub.6 alkynyl; and substituted C.sub.1 to C.sub.Type: GrantFiled: June 12, 1987Date of Patent: December 12, 1989Assignee: ICI Australia LimitedInventors: Keith G. Watson, Craig G. Lovel
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Patent number: 4883883Abstract: Novel N-[(meth)allyloxy-mono-/di(meth)allylphenyl]maleimides, in admixture with at least one N-[(meth)allyloxyphenyl]maleimide, are reacted with at least one bismaleimide, and optionally a hydroxylated organosilicon compound, in the presence of an imidazole compound, to obtain mechanically improved thermosetting imido copolymerizates well adapted for the production of, e.g., coatings, adhesive bondings, laminates and composites.Type: GrantFiled: December 17, 1987Date of Patent: November 28, 1989Assignee: Rhone-Poulenc ChimieInventors: Pascal Barthelemy, Michel Crochemore
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Patent number: 4851547Abstract: A method for the production of a maleimide by dehydration and ring-closure of maleinamic acid obtained by the reaction of maleic anhydride with an amine, which method is characterized by effecting ring-closure imidation of said maleinamic acid by heating said maleinamic acid in a water-insoluble or water-immiscible inert organic non-polar solvent in the presence of a catalyst of an amine salt produced from the amine and an acid, a mixture of the amine salt and the acid, or a supported catalyst on a solid carrier the catalyst or the acid.Type: GrantFiled: December 23, 1988Date of Patent: July 25, 1989Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Yuichi Kita, Koichi Nakagawa, Kentaro Sakamoto, Akio Fukui, Masao Baba, Yoichi Nakagawa
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Patent number: 4851546Abstract: Disclosed is a process for making a 2-pyrrolidone and a succinimide by the vapor phase catalytic reaction of a maleimide with molecular hydrogen.Type: GrantFiled: October 28, 1988Date of Patent: July 25, 1989Assignee: The Standard Oil CompanyInventors: Anne M. Graham, Thomas G. Attig
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Patent number: 4841069Abstract: Ammonolysis-alkylation using a C.sub.1 to C.sub.8 alkanol and ammonia is used to prepare cyclic N-alkylated compounds in a one-step process. In the presence of hydrogen added as a reducing agent, a reduced N-alkylated compound can be formed.Type: GrantFiled: March 30, 1987Date of Patent: June 20, 1989Assignee: Amoco CorporationInventor: Robert J. Olsen
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Patent number: 4826997Abstract: The invention is a compound which comprises an unsaturated cyclic imide moiety and an aryl cyclobutene moiety, wherein the cyclobutene moiety is fused to the aryl radical, and wherein the imide nitrogen is connected to the aryl radical by a direct bond or a bridging member. Another aspect of this invention is a polyimide polymeric composition which results from the polymerization of the above-described compounds.Type: GrantFiled: August 4, 1986Date of Patent: May 2, 1989Assignee: The Dow Chemical CompanyInventor: Robert A. Kirchhoff
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Patent number: 4814464Abstract: An improved process for making N-alkylpyrrolidones from a maleic derivative or a succinic derivative which involves catalytically reducing the maleic derivative with hydrogen to succinic anhydride, if the maleic derivative is the starting point, converting succinic anhydride to a N-alkylsuccinimide by ammonolysis-alkylation with a C.sub.1 and C.sub.4 alkanol and ammonia, and catalytically reducing the resulting N-alkylsuccinimide to the N-alkylpyrrolidone.Type: GrantFiled: March 30, 1987Date of Patent: March 21, 1989Assignee: Amoco CorporationInventor: Robert J. Olsen
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Patent number: 4812579Abstract: A process for producing N-substituted maleimides which comprises heating maleic anhydride and an aromatic or aliphatic amine, or maleic acid monoamides obtained from them, in the presence of an ion exchange resin in an organic solvent to effect cyclodehydration.Type: GrantFiled: October 13, 1987Date of Patent: March 14, 1989Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Shunichi Doi, Yasuyuki Takayanagi
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Patent number: 4808646Abstract: Solutions of maleimide resins comprising a mixture of bismaleimides and low but solubilizing amounts of maleamic acids are provided at high solids levels, e.g. at least about 50%. Such solutions which comprise common solvents such as acetone, methyl ethyl ketone and toluene are useful in preparing laminates based on bismaleimide resins.Type: GrantFiled: June 15, 1987Date of Patent: February 28, 1989Assignee: Monsanto CompanyInventor: Ronald H. Dahms
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Patent number: 4801586Abstract: This invention relates to a method for administering systemically active agents including therapeutic agents through the skin or mucosal membranes of humans and animals in a transdermal device or formulation comprising topically administering with said systemic agent an effective amount of a membrane penetration enhancer having the structural formula ##STR1## wherein X and Y, each, may represent sulfur, oxygen or two hydrogen atoms, A is a branched or a straight chain, divalent aliphatic radical having from 0 to 2 double bonds; R' is selected from the group consisting of H, a lower alkyl group having 1-4 carbon atoms, phenyl, lower alkyl or halogen substituted phenyl, acetamido, halogen, piperidinyl, lower alkyl or halogen substituted piperidinyl, carbalkoxy, carboxamide, and alkylformyl; m is 3-7; q is 2m-2x, wherein x equals the number of double bonds in the lactam ring and may be 1, 2 or 3, and R is CH.sub.3, ##STR2## wherein R" is H or halogen.Type: GrantFiled: October 7, 1986Date of Patent: January 31, 1989Assignee: Nelson Research & Development Co.Inventors: Gevork Minaskanian, James V. Peck