And Chalcogen Bonded Directly To The Other Ring Carbon Of The Five-membered Hetero Ring Which Is Adjacent To The Ring Nitrogen (e.g., Succinimide, Etc.) Patents (Class 548/545)
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Patent number: 5696282Abstract: A process comprises contacting, in the presence of a catalyst, hydrogen sulfide or a mercaptan such as, for example, n-dodecyl mercaptan with an .alpha.,.beta.-unsaturated carbonyl or .alpha.,.beta.-unsaturated cyano compound such as, for example, methyl acrylate wherein the catalyst comprises a pyridine derivative such as, for example, 4-(dimethylamino)pyridine or an ion exchange resin such as, for example, "AMBERLYST A-21" to produce a 3-hydrocarbylthio derivative of the .alpha.,.beta.-unsaturated carbonyl or .alpha.,.beta.-unsaturated cyano compound such as, for example, methyl 3-(dodecylthio)propionate.Type: GrantFiled: March 26, 1996Date of Patent: December 9, 1997Assignee: Phillips Petroleum CompanyInventors: James E. Shaw, Harry Porter
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Patent number: 5688825Abstract: Disclosed is a method of inhibiting anandamide amidase in an individual or animal and novel inhibitors of anandamide amidase. The disclosed method and novel compounds can be used to reduce pain in an individual or animal suffering from pain, reducing nausea in an individual undergoing chemotherapy, for example cancer chemotherapy, suppressing appetite in an individual, reducing intraocular pressure in the eye of an individual or animal suffering from glaucoma and suppressing the immune system in an individual with an organ transplant.Type: GrantFiled: May 31, 1996Date of Patent: November 18, 1997Assignee: University of ConnecticutInventors: Alexandros Makriyannis, Sonyan Lin, William Adam Hill
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Patent number: 5684163Abstract: A process for the preparation of a N-)ortho-alkylphenyl)-imide of the formula ##STR1## in which R.sup.1 to R.sup.9 is defined in the specification which comprises reacting a cyclic anhydride of the formula ##STR2## wherein R.sup.6 to R.sup.9 are difined in the specification with an amine of the formula ##STR3## optionally in the presence of an acid catalyst and optionally in the presence of a solvent which is immiscible or only slightly miscible with water but can form an azeotrope with water, at a temperature between 100.degree. to 200.degree. C. under conditions so that the water formed during the reaction is removed from the reaction mixture without the addition of a polymerization inhibitor or a dipolar solvent. The final products are used as intermediates to prepare heat-stable plastics as well as intermediates to prepare pharmaceutical and agricultural chemicals.Type: GrantFiled: February 5, 1996Date of Patent: November 4, 1997Assignee: Bayer AktiengesellschaftInventors: Torsten Groth, Bernd-Michael Konig, Josef Kasbauer, Michael Schwamborn
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Patent number: 5681963Abstract: Fluorinated imides useful for imparting repellency of low surface tension fluids to thermoplastic polymers of formulae ##STR1## wherein R.sub.1 is F(CF.sub.2).sub.x --(CH.sub.2).sub.m, or F(CF.sub.2).sub.x SO.sub.2 N(R.sub.5) (CH.sub.2) .sub.p wherein x is from about 4 to about 20, m is from about 2 to about 6, p is from 1 to about 12, and R.sub.5 is an alkyl radical of from 1 to about 4 carbons;R.sub.2 is a linear, branched or cyclic alkylene or poly(oxyalkylene) hydrocarbon group having from about 2 to about 15 carbons;R.sub.3 is selected from the group consisting of F(CF.sub.2).sub.x --(CH.sub.2).sub.m, F(CF.sub.2).sub.x --(CH.sub.2).sub.m --OC(O)--(CH.sub.2).sub.n, and F(CF.sub.2).sub.x SO.sub.2 N(R.sub.5)(CH.sub.2).sub.p OC(O)(CH.sub.2).sub.n wherein x is from about 4 to about 20, m is from about 2 to about 6, n is about 2 to about 12, p is from 1 to about 12, and R.sub.5 is an alkyl radical of from 1 to about 4 carbons;R.sub.4 is an alkyl or alkenyl group of from about 4 to about 20 carbons, andR.sub.Type: GrantFiled: December 21, 1995Date of Patent: October 28, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventor: Theodor Arthur Liss
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Patent number: 5654477Abstract: The present invention relates to a novel enantiospecific processes for preparing (S)-4-amino-hepta-5,6-dienoic acid and pharmaceutically acceptable salts thereof, which is useful as an irreversible inhibitor of GABA-T, to novel intermediates thereof, and a process for preparing an intermediate thereof.Type: GrantFiled: March 6, 1995Date of Patent: August 5, 1997Assignee: Merrell Pharmaceuticals Inc.Inventor: H. Michael Kolb
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Patent number: 5644001Abstract: This invention relates to novel pure hydrocarbyl succinylating agents, substantially pure derivatives thereof, to a method of preparation of pure substituted succinylating agents and their derivatives, and to the use of thereof as additives for fuels and lubricants. The hydrocarbyl substituted succinylating agents are pure because the real and apparent mole ratios of the succinyl groups to the hydrocarbyl groups in such agents are substantially the same. These are produced by reacting an olefin polymer such as poly(iso)butylene with maleic anhydride to form a hydrocarbyl substitued succinylating agent which is then cleaned by solvent extraction to remove any impurities therein before use in further reactions.Type: GrantFiled: March 11, 1996Date of Patent: July 1, 1997Assignee: BP Chemicals LimitedInventors: John Richard Blackborow, Michael John Clarke
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Patent number: 5637731Abstract: This disclosure describes novel substituted oxotremorine derivatives of formula I having nitrogen, oxygen or sulfur groups and the prodrug forms of these derivatives. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and the processes for the production of the compounds.Type: GrantFiled: April 30, 1996Date of Patent: June 10, 1997Assignee: American Home Products CorporationInventors: Eugene J. Trybulski, Richard H. Kramss, Herbert J. Brabander
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Patent number: 5631381Abstract: Process for preparing complex pesticidal 1-(haloaryl)heterocyclic compounds by reacting 1-(nitroaryl)heterocycles with metallic halide salts.Type: GrantFiled: June 28, 1996Date of Patent: May 20, 1997Assignee: Rhone-Poulenc Inc.Inventors: Jamin Huang, Scot K. Huber, Philip H. G. Smith, John H. Wilkinson
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Patent number: 5631259Abstract: Cycloalkyltriols containing heterocyclic substituents, in particular cyclopentyl- and cyclohexyltriols containing heterocyclic substituentsCompounds of the formulae I and II ##STR1## in which the substituents A, R.sup.1, R.sup.2 and R.sup.3 and n have the meanings given, have an antiviral and antiparasitic action.Type: GrantFiled: June 6, 1995Date of Patent: May 20, 1997Assignee: Hoechst AktiengesellschaftInventors: Gerhard J ahne, Irvin Winkler, Matthias Helsberg, Heinz H anel
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Patent number: 5614638Abstract: New nonionic radiographic contrast agents having the formula ##STR1## wherein Y is a single bond, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, ##STR2## --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 --, --O-- or ##STR3## R.sub.1, R.sub.1 ' and R.sub.2 are the same or different and are hydrogen, alkyl or hydroxyalkyl.Hydroxyalkyl refers to such alkyl groups having 1 or more hydroxy groups. Preferred hydroxyalkyl groups include: ##STR4## R.sub.3 and R.sub.4 are the same or different and are hydrogen, methyl or --CH.sub.2 CH.sub.2 OH; R.sub.5 is hydrogen, alkyl, --CH.sub.2 CH.sub.2 OH, CH.sub.2 OH or OH and R.sub.6 is alkyl, --CH.sub.2 CH.sub.2 OH, CH.sub.2 OH, OH or hydrogen and may be the same or different than R.sub.5 and m is zero or one, with the proviso that no methylene or methine carbon atom of the heterocyclic ring is attached to both a nitrogen and an oxygen atom with the additional proviso that when Y is a single bond, m is not zero.Type: GrantFiled: June 5, 1992Date of Patent: March 25, 1997Assignee: Bracco International B.V.Inventors: Ramachandran S. Ranganathan, Thangavel Arunchalam, Edmund R. Marinelli, Radhakrishna K. Pillai
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Patent number: 5609848Abstract: Haloaryl compounds are lithiated and thereafter metalated with one of the following organometallic groups: Sn(n--Bu).sub.3 or SnMe.sub.3. The resulting aryltin compound can be transmetalated in site-specific reaction with one of the following organometallic groups: HgX, Hg(OAc).sub.2, BX.sub.3, or BZ.sub.2, wherein X is Cl, Br, or I, and Z is alkyl or alkoxy. The metalated compounds are subsequently radiohalogenated via a demetalation reaction. A functional group suitable for conjugation to protein can be added subsequent or preferably prior to the radiohalogenation.Also compounds of the formula: R.sub.1 --Ar--R.sub.2, wherein R.sub.1 is either a radiohalogen or any one of the organometallic groups stated above, Ar is aromatic or heteroaromatic ring, and R.sub.2 is a short-chain substituent that does not activate the aromatic ring and that bears a functional group, or a precursor thereof, suitable for conjugation to protein under conditions that preserve the biological activity of the protein.Type: GrantFiled: September 23, 1991Date of Patent: March 11, 1997Assignee: NeoRx CorporationInventors: D. Scott Wilbur, Alan R. Fritzberg
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Patent number: 5585500Abstract: A method of producing optically active pyrrolidines of the general formula ##STR1## in which R.sup.1 is hydrogen or OH,R.sup.2 is a benzyl group which can have one or more alkyl-, alkoxy- and/or halogen substituents on the aromatic, and* is and/or can be an asymmetric center,by reducing the corresponding, enantiomerically pure pyrrolidinediones using activated alkali boron hydride.Type: GrantFiled: July 17, 1995Date of Patent: December 17, 1996Assignee: Degussa AktiengesellschaftInventors: Karlheinz Drauz, Matthias Kottenhahn, Michael Kraft, Michael Schwarm
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Patent number: 5554768Abstract: The present invention relates to succinimides of the formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are hydrogen, C.sub.1 -C.sub.24 -alkyl, C.sub.2 -C.sub.24 -alkenyl, C.sub.6 -C.sub.12 -cycloalkyl, C.sub.6 -C.sub.12 -cycloalkenyl, C.sub.6 -C.sub.12 -aryl, C.sub.1 -C.sub.24 -alkoxy, C.sub.1 -C.sub.24 -acyl, C.sub.1 -C.sub.24 -acyloxy, a hydroxyl, amino or sulfo group or a C.sub.1 -C.sub.24 -dialkylamino, C.sub.1 -C.sub.24 -acylamino, C.sub.1 -C.sub.24 -alkylsulfato, C.sub.1 -C.sub.24 -alkylsulfonato, C.sub.1 -C.sub.24 -alkylsulfito, C.sub.1 -C.sub.24 -alkylsulfinyl or C.sub.1 -C.sub.24 -alkoxycarbonyl radical, andR.sup.3 is a polyhydroxyalkyl radical of the formula ##STR2## in which R.sup.4 is --(CHOR.sup.7).sub.n --H,R.sup.5 is --(CHOR.sup.7).sub.m --H,R.sup.6 is --(CHOR.sup.7).sub.o --H where n+m+o is 2-6, andR.sup.7 is H or a carbohydrate attached in the form of a glycoside from the series comprising reducing sugars, a process for their preparation and their use.Type: GrantFiled: May 25, 1994Date of Patent: September 10, 1996Assignee: Hoechst AktiengesellschaftInventors: Reinhard D onges, Rudolf Ehrler, Rainer Helwerth
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Patent number: 5541341Abstract: The present invention relates to a new class of carbohydrate based nonionic surfactant, i.e., alkyl and alkenyl glycasuccinimide, and a process for their manufacture.Type: GrantFiled: March 24, 1995Date of Patent: July 30, 1996Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Robert Vermeer, Van Au, Bijan Harichian
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Patent number: 5539126Abstract: A method is provided for preparing homochiral maleimide intermediates of the structure ##STR1## wherein R.sup.7, R.sup.8 and R.sup.9 are as defined herein by reacting a homochiral amine of the structure ##STR2## with maleic anhydride and a silylating agent. The maleimide intermediate is used in the enantio-selective preparation of thromboxane A.sub.2 receptor antagonists.Type: GrantFiled: April 20, 1994Date of Patent: July 23, 1996Assignee: Bristol-Myers Squibb CompanyInventors: Michael J. Humora, Richard H. Mueller, Janak Singh, Yadagiri Pendri
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Patent number: 5523417Abstract: This invention relates to novel pure hydrocarbyl succinylating agents, substantially pure derivatives thereof, to a method of preparation of pure substituted succinylating agents and their derivatives, and to the use of thereof as additives for fuels and lubricants. The hydrocarbyl substituted succinylating agents are pure because the real and apparent mole ratios of the succinyl groups to the hydrocarbyl groups in such agents are substantially the same. These are produced by reacting an olefin polymer such as poly(iso)butylene with maleic anhydride to form a hydrocarbyl substitued succinylating agent which is then cleaned by solvent extraction to remove any impurities therein before use in further reactions.Type: GrantFiled: December 3, 1993Date of Patent: June 4, 1996Assignee: BP Chemicals LimitedInventors: John R. Blackborow, Michael J. Clarke
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Patent number: 5514815Abstract: Novel succinimide derivatives of formula I!: ##STR1## wherein Ring A is tri-lower alkoxyphenyl, R.sup.1 and R.sup.2 combine each other to form a group of the formula:>N--R.sup.3or one of R.sup.1 and R.sup.2 is lower alkoxy, and the other is group of the formula: --NHR.sup.3, in which R.sup.3 is hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkoxy, substituted or unsubstituted amino, hydroxy or pyridylcarbonyl, or salts thereof, these compounds have excellent antithrombotic activity and are useful as antithrombotic drug, or synthetic intermediate for preparing other antithrombotic drug.Type: GrantFiled: March 18, 1993Date of Patent: May 7, 1996Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Tameo Iwasaki, Takashi Nishitani, Akio Ohtani, Masanori Inamasu
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Patent number: 5508434Abstract: Polysuccinimide of varying molecular weight has been prepared by heat polymerization of aspartic acid in the presence of a sulfur-containing dehydrating agent employing a variety of reaction mixtures and reaction conditions. Sulfur trioxide and heat decomposable sulfur trioxide precursor dehydrating agents are preferred for this purpose. The presence of an acid scavenger within the reaction mixture is desirable and leads to a relatively higher molecular weight polysuccinimide, while the absence of an acid scavenger results in a relatively lower molecular weight polysuccinimide.Type: GrantFiled: September 28, 1994Date of Patent: April 16, 1996Assignee: Donlar CorporationInventors: Daniel A. Batzel, James F. Kneller, Abdul R. Y. Meah
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Patent number: 5508437Abstract: Analogs of Tyrosine Sulfate or Tyrosine Phosphate containing peptides, the novel intermediate compounds used in the preparation of these analogs, as well as a method for suppressing appetite in subjects by administering to the subject an effective amount of CCK analog wherein one or more of any Tyrosine Sulfate present is substituted with a radical of the invention.Type: GrantFiled: December 17, 1993Date of Patent: April 16, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Waleed Danho, Jefferson W. Tilley, Joseph Triscari, Rolf Wagner
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Patent number: 5493031Abstract: N-hydroxysuccinimide monohydrate is precipitated from an aqueous solution of N-hydroxysuccinimide. N-hydroxysuccinimide monohydrate is a new compound that can be used to produce anhydrous N-hydroxysuccinimide which is substantially pure. It can also be used as a substitute for N-hydroxysuccinimide when the presence of water is not detrimental.Type: GrantFiled: June 16, 1994Date of Patent: February 20, 1996Assignee: PPG Industries, Inc.Inventor: Cheruthur Govindan
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Patent number: 5475021Abstract: The present invention includes N-substituted maleimides (1(H)-Pyrrole-2,5-dione (Maleimide) analogs and succinimides which act as potent nonsteroidal anti-inflammatory drugs and are capable of dual inactivation or selective inactivation of the cyclooxygenase and the peroxidase activities of prostaglandin endoperoxide synthase (PGHS).Type: GrantFiled: December 3, 1993Date of Patent: December 12, 1995Assignee: Vanderbilt UniversityInventors: Lawrence J. Marnett, Amit S. Kalgutkar
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Patent number: 5475106Abstract: Compounds of formula: ##STR1## in which R.sub.1 represents a hydrogen atom, an alkyl or alkoxycarbonyl radical or a phenyl radical, optionally substituted,R.sub.2 represents an alkoxy, optionally substituted cycloalkyloxy, cycloalkylalkyloxy, phenylalkyloxy, polyfluoroalkyloxy or cinnamyloxy radical or a radical --NR.sub.5 R.sub.6,R.sub.3 represents a phenylamino radical in which the phenyl ring is optionally substituted, an optionally substituted phenyl radical or a naphthyl, indolyl or quinolyl radical,R.sub.4 represents a substituted phenyl radical,R.sub.5 and R.sub.6, which may be identical or different, represent a hydrogen atom or an alkyl, optionally substituted phenyl, indanyl, cycloalkylalkyl, cycloalkyl or phenylalkyl radical, or alternatively R.sub.5 and R.sub.6, together with the nitrogen atom to which they are attached, form a heterocycle, their preparation and medicinal products containing them.Type: GrantFiled: October 8, 1992Date of Patent: December 12, 1995Assignee: Rhone-Poulenc Rorer S.A.Inventors: Jean-Dominique Bourzat, Marc Capet, Claude Cotrel, Claude Guyon, Franco Manfre, Gerard Roussel
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Patent number: 5463080Abstract: Compounds, useful as radiolabeling reagents, including a trihalogenated phenyl ring and having the formula ##STR1## wherein X.sub.1, X.sub.2 and X.sub.3 are halogens, one of which may be a radiohalogen, are disclosed. The invention further includes radiohalogenated proteins as well as processes for preparing such reagents and radiohalogenated proteins.Type: GrantFiled: August 27, 1992Date of Patent: October 31, 1995Assignee: Bracco International B.V.Inventors: Marc Ogan, Frank P. Tomasella, Jan-I Tu
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Patent number: 5453517Abstract: The invention relates to fluorescent and/or reactive derivatives of 1,2-bis-(2-aminophenoxyethane)-N,N,N',N'-tetraacetic acid (BAPTA) according to the formula: ##STR1## where at least one of W and X is a functional group, with or without a spacer, that terminates in an alcohol or phenol, a thiol, a haloacetamide, an alkyl halide, an amine or aniline, a carboxylic acid, an anhydride, an isocyanate, an isothiocyanate, a maleimide, or an activated ester. The BAPTA-like molecule may be further substituted, one or more times, by additional functional groups with or without spacers or by CH.sub.3, NO.sub.2, CF.sub.3, F, Cl, Br, I, or carboxylic acid derivatives or pharmaceutically acceptable salts thereof, or by indolyl or benzofuran fluorophores. The functional groups allow for subsequent covalent attachment of one or more oxygen heterocycle fluorophores (e.g. fluorescein, coumarin, rhodamine); or polymolecular assemblies (e.g.Type: GrantFiled: February 25, 1992Date of Patent: September 26, 1995Assignee: Molecular Probes, Inc.Inventors: Michael A. Kuhn, Richard P. Haugland
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Patent number: 5442086Abstract: Disclosed are certain poly-methine compounds having the formula ##STR1## wherein each R.sup.1 is independently selected from cyano; carboxy; alkenyloxycarbonyl; an unsubstituted or substituted alkoxycarbonyl, cycloalkoxycarbonyl or aryloxycarbonyl radical; an unsubstituted or substituted, carbocyclic or heterocyclic aryl radical; an unsubstituted or substituted alkanoyl, cycloalkanoyl or aroyl radical; an unsubstituted or substituted carbamoyl radical; or an unsubstituted or substituted alkylsulfonyl, cycloalkylsulfonyl or arylsulfonyl radical; each R.sup.2 is independently selected from cyano or an unsubstituted or substituted alkoxycarbonyl, cycloalkoxycarbonyl or aryloxycarbonyl radical; each A is independently selected from an unsubstituted or substituted 1,2-phenylene or 1,2-naphthylene radical; each Z is independently selected from --0-- or --S--; and L is an organic linking group bonded by non-oxo carbon atoms to each Z atom.Type: GrantFiled: September 19, 1994Date of Patent: August 15, 1995Assignee: Eastman Chemical CompanyInventors: James J. Krutak, Max A. Weaver, Clarence A. Coates, Jr., Samuel D. Hilbert, Terry A. Oldfield, William W. Parham, Wayne P. Pruett
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Patent number: 5426190Abstract: Acylated derivatives of N-hydroxysuccinimide are produced from succinic anhydride, hydroxylamine, and acylating agent without purification of the intermediate N-hydroxysuccinimide.Type: GrantFiled: June 16, 1994Date of Patent: June 20, 1995Assignee: PPG Industries, Inc.Inventors: Cheruthur Govindan, Suresh B. Damle
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Patent number: 5420285Abstract: 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: March 4, 1993Date of Patent: May 30, 1995Assignee: Johnson Matthey, Inc.Inventors: David A. Schwartz, Michael J. Abrams, Christen M. Giandomenico, Jon A. Zubieta
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Patent number: 5410068Abstract: The invention pertains to compounds and methods for the reversible modification of natural products, biopolymers or synthons for natural products or biopolymers, such as nucleosides, nucleotides, and oligonucleosides. The modification enables one to perform a variety of chemistries on these compounds, yet can be removed to regenerate functional groups on the natural products, biopolymer or synthon of interest.Type: GrantFiled: October 23, 1989Date of Patent: April 25, 1995Assignee: PerSeptive Biosystems, Inc.Inventors: James M. Coull, Brian Gildea, Hubert Koester
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Patent number: 5405918Abstract: Novel polysulfide-containing polycitraconimides and polyitaconimides are disclosed. Further, a process for the sulfur-vulcanization of rubber using these novel compounds is also disclosed. Also, a sulfur-vulcanized rubber product and articles of manufacture embodying this product are disclosed. Finally, the use of the novel polysulfide-containing polycitraconimides and polyitaconimides as anti-reversion coagents in the sulfur-vulcanization of rubber is also disclosed.Type: GrantFiled: April 28, 1993Date of Patent: April 11, 1995Assignee: Akzo Nobel N.V.Inventors: Andreas H. Hogt, Auke G. Talma, Rudolf F. de Block
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Patent number: 5384055Abstract: A lubricant additive composition and method for production is disclosed comprising the adduct of an olefinic oligomer and an enophile, said olefinic oligomer comprising the product of the oligomerization of C.sub.2 to C.sub.24 alpha-olefin feedstock, or mixtures thereof, under oligomerization conditions in contact with a reduced valence state Group VIB metal catalyst on porous support. Maleic anhydride is a preferred enophile. The maleic anhydride adduct is reacted with polyamines such as tetraethylene pentamine to form the corresponding alkenyl bis-succinimide.Type: GrantFiled: November 16, 1992Date of Patent: January 24, 1995Assignee: Mobil Oil CorporationInventor: Henry Ashjian
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Patent number: 5362410Abstract: The incorporation of the heterocyclic saccharin functionality into the alkenylsuccinimide dispersant structures via the Mannich alkylaminoalkylation procedure provides a class of ashless non-phosphorus dispersants with multifunctional antiwear, antioxidant and corrosion inhibiting properties in lubricant compositions.Type: GrantFiled: September 13, 1993Date of Patent: November 8, 1994Assignee: Mobil Oil CorporationInventors: Abraham O. M. Okorodudu, Angeline B. Cardis
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Patent number: 5359085Abstract: A fulgimide derivative of the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 are independently alkyl cycloalkyl aryl etc.; R.sup.4 is thienyl, indolyl, furyl, etc.; X is a divalent organic residue; and R is amino, OH, etc., or a vinyl group, has a photochromic action and can be used for producing photochromic polymers and copolymers.Type: GrantFiled: July 27, 1990Date of Patent: October 25, 1994Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Osamu Iwamoto, Taizo Hara, Haruhiko Sugiyama
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Patent number: 5334321Abstract: Alkenyl or alkyl succinimide additives which are the reaction product of a high molecular weight alkenyl- or alkyl-substituted succinic anhydride and a polyalkylene polyamine having an average of greater than 4 nitrogen atoms per mole, wherein the reaction product is post-treated with a cyclic carbonate, are compatible with fluorocarbon engine seals and, for concentration levels at which fluorocarbon seal compatibility is achieved, possess improved dispersancy and/or detergency properties when employed in lubricating oils and fuels,Type: GrantFiled: March 9, 1993Date of Patent: August 2, 1994Assignee: Chevron Research and Technology Company, a Division of Chevron U.S.A. Inc.Inventors: James J. Harrison, William R. Ruhe, Jr.
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Patent number: 5329022Abstract: The present invention relates to an improved synthesis method for the making of citraconimides wherein a citraconic anhydride is reacted with 0.5 to 2.0 equivalents of at least one amine salt. This process may be carried out in a solvent and generally leads to excellent yields of the citraconimides with high selectivity and easy purification. The present inventional so relates to a process for the production of citraconic anhydride from itaconic anhydride with an amine or phosphine catalyst and in a cosolvent.Type: GrantFiled: January 16, 1992Date of Patent: July 12, 1994Assignee: Akzo America Inc.Inventors: Auke G. Talma, Hendrika P. M. Hooft, Anna G. van de Bovenkamp-Bouwman
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Patent number: 5324709Abstract: A tetrahydrofuran derivative represented by the following general formula [I]: ##STR1## wherein A represents direct bonding or a group represented by --B--CHR.sup.1 --(wherein B represents oxygen atom, sulfur atom or imino group; R.sup.1 represents hydrogen atom or an alkyl group); R represents hydrogen atom, halogen atom, hydroxyl group, an alkoxy group, benzyloxy group, an alkylsulfonyloxy group or a group represented by --O--COR.sup.2 (wherein R.sup.2 represents an alkyl group, a haloalkyl group, an alkenyl group, a cycloalkyl group, phenyl group, benzyl group, an alkoxy group, an alkylamino group or a dialkylamino group; X represents halogen atom; Y represents hydrogen atom or halogen atom) and the herbicide containing the same as the effective ingredient. The compounds of the present invention have exceedingly high herbicidal activity, and furthermore, the compounds are superior to the known similar compounds in terms of safety on crops. Thus, the compounds are useful as herbicides.Type: GrantFiled: November 20, 1992Date of Patent: June 28, 1994Assignee: Mitsubishi Kasei CorporationInventors: Natsume Bunji, Kyomura Nobuo, Suzuki Seiichi, Takahashi Yoji, Jikihara Tetsuo
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Patent number: 5319101Abstract: Reactive multifunctional imide monomers have been discovered from which radiation curable oligomers and polymers may be derived. The reactive imide monomers have at least one functional group which is polymerizable under free radical or ionic polymerization conditions with other similar functional groups. However, the same functional group and reaction product derived therefrom is substantially not subject to cleavage by oxidation or hydrolysis. The reactive imide monomer also contains at least one other functional group which remains intact under the above-described polymerization conditions to form a part of a side chain of the resultant polymer and will cross-link or cure by 2+2 cyclo-addition with other like functional groups upon irradiation.Type: GrantFiled: June 30, 1992Date of Patent: June 7, 1994Assignee: The B. F. Goodrich CompanyInventors: Carl J. Long, II, William F. Masler, III, William R. Wilber, Gary L. Julian
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Patent number: 5302740Abstract: Disclosed are certain poly-methine compounds having the formula ##STR1## wherein each R.sup.1 is independently selected from cyano; carboxy; alkenyloxycarbonyl; an unsubstituted or substituted alkoxycarbonyl, cycloalkoxycarbonyl or aryloxycarbonyl radical; an unsubstituted or substituted, carbocyclic or heterocyclic aryl radical; an unsubstituted or substituted alkanoyl, cycloalkanoyl or aroyl radical; an unsubstituted or substituted carbamoyl radical; or an unsubstituted or substituted alkylsulfonyl, cycloalkylsulfonyl or arylsulfonyl radical; each R.sup.2 is independently selected from cyano or an unsubstituted or substituted alkoxycarbonyl, cycloalkoxycarbonyl or aryloxycarbonyl radical; each A is independently selected from an unsubstituted or substituted 1,2-phenylene or 1,2-naphthylene radical; each Z is independently selected from --O-- or --S--; and L is an organic linking group bonded by non-oxo carbon atoms to each Z atom.Type: GrantFiled: October 30, 1992Date of Patent: April 12, 1994Assignee: Eastman Kodak CompanyInventors: James J. Krutak, Max A. Weaver, Clarence A. Coates, Jr., Samuel D. Hilbert, Terry A. Oldfield, William W. Parham, Wayne P. Pruett
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Patent number: 5283165Abstract: Pyrrolinone dyes, and photographic materials containing them, which dyes have the formula: ##STR1## wherein; E.sup.1 represents an electron withdrawing group;R.sup.1 represents an aryl group of 6 to 14 carbon atoms or an alkyl group of from 1 to 12 carbon atoms;R.sup.2 represents an alkyl or alkylthio group of 1 to 20 carbon atoms, or an alkenyl group of 2 to 20 carbon atoms, or an aryl, aralkyl, heterocyclic or cycloalkyl group any of which have 5 to 14 carbon atoms, or R2 represents a hydroxy, cyano, chloro, nitro or hydrogen;M.sup.+ is a cation;each L represents a methine group;m is 0, 1, 2, or 3; and D is a moiety in conjugation with the oxygen of the pyrollinone ring.The dyes are particularly useful as solid particle filter dye dispersions in photographic elements.Type: GrantFiled: December 23, 1992Date of Patent: February 1, 1994Assignee: Eastman Kodak CompanyInventors: Donald R. Diehl, Margaret J. Helber, Louis J. Rossi
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Patent number: 5281698Abstract: The present invention is a process for preparing an activated ester of polyethylene glycol or a polyoxyethylated polyol. After the activated ester is prepared, it can be reacted with a protein to form a polymer/protein conjugate. Conjugation with a polymer can reduce the protein's immunogenicity, increase its solubility, and increase its circulating in vivo half-life. Preferred proteins are IL-2, CSFs, and interferons.Type: GrantFiled: July 23, 1991Date of Patent: January 25, 1994Assignee: Cetus Oncology CorporationInventor: Danute E. Nitecki
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Patent number: 5270339Abstract: There are described a phenoxybenzene derivative having the formula (I): ##STR1## wherein R.sup.1 is hydrogen atom; an alkyl group having 1 to 3 carbon atoms; --OR.sup.6 or a halogen atom,R.sup.2 is hydrogen atom, nitro group or amino group,R.sup.3 is hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 5 carbon atoms, allyl group, vinyl group or --(CH.sub.2)n.sup.1 R.sup.7R.sup.4 is hydrogen atom, an alkyl group having 1 to 3 carbon atoms or --(CH.sub.2)n.sup.3 R.sup.25R.sup.5 hydrogen atom; an alkyl group having 1 to 3 carbon atoms; or phenyl group,X is ##STR2## wherein Y is oxygen atom or sulfur atom; or --CHR.sup.27 -- and line means a single bond or a double bond provided that n is 2 in case that the line means a single bond and n is 1 in case that the line means a double bond, ora pharmacologically acceptable salt thereof,a cognition enhancer comprising the same as an effective ingredient andan antidepressant comprising the same as an effective ingredient.Type: GrantFiled: December 3, 1992Date of Patent: December 14, 1993Assignee: Kanagafuchi Kagaku Kogyo Kabushiki KaishaInventors: Kozo Yamamoto, Yoshihide Fuse, Hideyuki Kishida, Naoko Yasuhara, Toshiaki Miwa, Ikuo Katsumi, Takayoshi Hidaka
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Patent number: 5256791Abstract: This invention relates to novel processes for preparing compounds of the formulae ##STR1## wherein R and X defined as below. Compounds of the formulae VII are useful as intermediates in the syntheses of azabicyclo quinoline carboxylic acids having antibacterial activity. This invention also relates to certain novel intermediates in the syntheses such antibiotics.Type: GrantFiled: March 2, 1992Date of Patent: October 26, 1993Assignee: Pfizer Inc.Inventor: Tamim F. Braish
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Patent number: 5235067Abstract: A continuous process has been found for producing hydroxyacylated alkenyl-substituted mono- and bis- succinimides. The Mannich phenol coupled compositions are produced continuously as well. In the imidization reaction, an alkenyl succinic anhydride is contacted with a polyamine to form mono- and bis- polyamino alkenyl succinimides in continuous stirred tank reactor for a residence time of 1 to 3 hours. The reaction product is then, optionally Mannich base coupled. Finally, in the amidization, the mono- and bis- polyamino alkenyl succinimide is contacted with an acylating agent such as hydroxyacetic acid. Contacting is carried out in a continuous stirred tank reactor for a residence time of 3 to 6 hours. A hydroxyacylated alkenyl-substituted mono- and bis- succinimide product free of haze is produced in the absence of filtering, by reducing water continuously in all three reactors to a concentration of 0.4 wt %.Type: GrantFiled: November 3, 1989Date of Patent: August 10, 1993Assignee: Texaco Inc.Inventors: Billy R. Allen, Bobby R. Martin, John A. Lemen, Leonard A. Matthews
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Patent number: 5229393Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.Type: GrantFiled: April 6, 1992Date of Patent: July 20, 1993Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey
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Patent number: 5221318Abstract: Herbicidal N-aryl-substituted nitrogen-containing heterocycles of the formula ##STR1## in which Het represents a heterocycle of the formula ##STR2## R.sup.1 represents hydrogen or halogen and R.sup.2 represents halogen, hydroxyl or represents a radical --Z.sup.2 --R.sup.8,whereX.sup.1 represents oxygen, represents a --CH.sub.2 -- group, represents a ##STR3## group or represents a ##STR4## group, X.sup.2 represents nitrogen or a CH group,Z.sup.1 represents oxygen or sulphur,Z.sup.2 represents oxygen or sulphur,R.sup.3 and R.sup.4 independently of one another in each case represent hydrogen or alkyl,R.sup.5 and R.sup.6 either independently of one another in each case represent hydrogen or alkyl or together represent a double-linked alkanediyl radicalR.sup.7 represents hydrogen, alkyl or represents optionally substituted aryl andR.sup.8 represents in each case optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl.Type: GrantFiled: August 19, 1991Date of Patent: June 22, 1993Assignee: Bayer AktiengesellschaftInventors: Reiner Fischer, Uta Jensen-Korte, Franz Kunisch, Albrecht Marhold, Pieter Ooms, Otto Schallner, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 5217982Abstract: This invention relates to compounds which are derivatives of cyclopentane which are useful as antihypertensive agents, to pharmaceutical compositions including such compounds, and to their use in treating hypertension.Type: GrantFiled: November 15, 1990Date of Patent: June 8, 1993Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Cynthia A. Fink, Alfred P. Spada
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Patent number: 5214191Abstract: 2-Phenylalkanoate esters which are useful as inhibitors of human leukocyte elastase.Type: GrantFiled: May 22, 1990Date of Patent: May 25, 1993Assignee: Cortech, Inc.Inventors: Gary P. Kirschenheuter, Lyle W. Spruce, John C. Cheronis
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Patent number: 5208348Abstract: A mercaptan compound of the formula ##STR1## wherein R.sup.3 is a hydrogen atom or a lower alkyl group, or a salt thereof.Type: GrantFiled: July 14, 1992Date of Patent: May 4, 1993Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Tameo Iwasaki, Kazuhiko Kondo, Hiroshi Horikawa, Totaro Yamaguchi, Tadahiro Matsushita
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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: 5198133Abstract: Preconditioned automatic transmission fluids are made by using a preblend formed by heating an alkenyl succinimide or succinamide dispersant with a phosphorus ester and water to partially hydrolyze the ester and then mixing the preblend and other additives with a base oil.Type: GrantFiled: June 22, 1992Date of Patent: March 30, 1993Assignee: Ethyl Petroleum Additives, Inc.Inventor: Andrew G. Papay
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Patent number: 5182036Abstract: Borated hydroxyalkyl esters of alkyl- or alkenylsuccinimide-derived dithiocarbamic acids, have been found to be effective multifunctional additives in lubricant and fuel applications.Type: GrantFiled: September 27, 1991Date of Patent: January 26, 1993Assignee: Mobil Oil Corp.Inventors: Abraham O. M. Okorodudu, Angeline B. Cardis