And Chalcogen Bonded Directly To A Ring Carbon Of The Five Membered Hetero Ring Which Is Not Adjacent To The Ring Nitrogen (e.g., 2,4 Pyrrolidinediones, Etc.) Patents (Class 548/544)
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Patent number: 4935440Abstract: 3-[.omega.-(3,5-Di-t-butyl-4-hydroxyphenyl)alkanoyl]-pyrroles and their de-oxy analogs, for example, 3-(3,5-di-t-butyl-4-hydroxybenzyl)pyrrole, 2-chloro-4-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole, 3-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole and 3-[2-(3,5-di-t-butyl-4-hydroxyphenyl)-1-oxoethyl]pyrrole, have high pharmacological potency as anti-inflammatory, analgesic and antipyretic agents.Type: GrantFiled: February 21, 1989Date of Patent: June 19, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Robert Greenhouse, John Young, D. V. Krishna Murthy
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Patent number: 4925868Abstract: The present invention relates to a compound of the formula: ##STR1## wherein X is sulfur or optionally substituted imino group; Y is a bond, oxygen, phenylene, phenyleneoxy, or oxyphenyleneoxy; R.sup.1 is hydrogen or optionally substituted hydrocarbon residue; R.sup.2 is optionally substituted hydrocarbon residue; and R.sup.1 may form, together with the imino-nitrogen atom as X, a nitrogen-containing 5- to 7-membered ring, production and use thereof.The compound (I) of the present invention has an anti-oxidation activity and activities of preventing or improving functional disorders due to biologically active oxygen species, thus being useful as a pharmaceutical agent for prophylaxis and therapy of disorders in the circulatory system.Type: GrantFiled: August 12, 1987Date of Patent: May 15, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Minoru Hirata
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Patent number: 4913721Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein V is an oxygen or a sulphur atom; X and Y, which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, haloalkyl, alkoxy, haloalkoxy, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted amino, acylamino, nitro, nitrile, --CO.sub.2 R.sup.3, --CONR.sup.4 R.sup.5, or --COR.sup.6 groups; or the groups X and Y, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; and Z is optionally substituted methylene, optionally substituted amino, oxygen or sulphur and when Z is a substituted methylene group, the substituent may join the 2-position of the phenyl ring to form a non-aromatic fused ring; R.sup.1 and R.Type: GrantFiled: October 31, 1988Date of Patent: April 3, 1990Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey
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Patent number: 4886908Abstract: (R)-4-amino-3-hydroxybutyric acid is prepared from the hydrochloride of the methyl ester or ethyl ester of (2S, 4R)-4-hydroxyproline via the intermediary stages of the corresponding, non-isolated (R)-4-hydroxy-1-pyrroline-2-carboxylic acid ester and the isolated (R)-4-hydroxy-2-pyrrolidone. The (R)-4-amino-3-hydroxybutyric acid which is useful for pharmacological purposes is obtainable in a high yield according to this method.Type: GrantFiled: February 29, 1988Date of Patent: December 12, 1989Assignee: Degussa AktiengesellschaftInventor: Johannes Haeusler
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Patent number: 4880940Abstract: 4-Alkoxy-3-pyrrolin-2-on-1-yl acetic acid alkyl esters are intermediate products for the production of cerebrally-active pharmaceutical products. The advantageous process for production of the new intermediate products is described.Type: GrantFiled: July 22, 1988Date of Patent: November 14, 1989Assignee: Lonza Ltd.Inventors: Thomas Muel, Leander Tenud, Laurent Duc, John McGarrity
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Patent number: 4879393Abstract: 4-Benzyloxy-3-pyrrolin-2-on-1-yl acetamide is an advantageous intermediate product for the production of pharmaceutically effective 4-hydroxypyrrolidin-2-1-yl acetamide. Processes for the production of the intermediate product as well as the active substance are described.Type: GrantFiled: April 14, 1988Date of Patent: November 7, 1989Assignee: Lonza Ltd.Inventor: Thomas Meul
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Patent number: 4879390Abstract: Purified Clausenamide of the formula ##STR1## is obtained by extraction of leaves of Clausena lansium followed by purification, Reduction products, ethers, etc. can be produced. The compounds are effective in treating hypoxia and amnesia.Type: GrantFiled: April 27, 1988Date of Patent: November 7, 1989Assignees: Chinese Academy of Medical Sciences, Bayer AktiengesellschaftInventors: Yen-rong Chen, Ming-he Yang, Liang Huang, Geng-tao Liu, Ulrich Benz
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Patent number: 4877884Abstract: 4-Benzyloxy-3-pyrrolin-2-on-1-yl acetamide is an advantageous intermediate product for the production of pharmaceutically effective 4-hydroxypyrrolidin-2-1-yl acetamide. Processes for the production of the intermediate product as well as the active substance are described.Type: GrantFiled: April 11, 1989Date of Patent: October 31, 1989Assignee: Lonza Ltd.Inventor: Thomas Meul
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Patent number: 4877887Abstract: The invention relates to novel alkoxy substituted maleimides of the formula ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, phenyl or phenylalkyl, and the organic radicals may furthermore carry inert substituents, and R.sup.2 and R.sup.3 are each C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.1 -C.sub.4 -haloalkyl or C.sub.2 -C.sub.4 -haloalkenyl, and alkoxy-substituted maleic anhydrides of the formula II ##STR2## where R.sup.2 is C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.1 -C.sub.4 -haloalkyl or C.sub.2 -C.sub.4 -haloalkenyl and Z is hydrogen, halogen or a radical OR.sup.3, where R.sup.3 is C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.1 -C.sub.4 -haloalkyl or C.sub.2 -C.sub.4 -haloalkenyl.The invention further relates to processes for preparing such maleimides I and the corresponding maleic anhydrides II and their use as graft monomers in graft polymers based on polyphenylene ethers.Type: GrantFiled: May 2, 1988Date of Patent: October 31, 1989Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Wolfgang Rohr
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Patent number: 4874874Abstract: A process for the preparation of a 3-sulphenylmaleimide of the formula ##STR1## in which R.sup.1 is alkyl, or optionally substituted cycloalkyl or aralkyl, andR.sup.2 is optionally substituted alkyl, cycloalkyl, aryl or aralkyl,comprising reacting a 3-sulphenylsuccinimide of the formula ##STR2## with an equimolar amount of hydrogen peroxide in the presence of a lower alkanecarboxylic acid. The compounds are fungicidal and those are new where R.sup.2 is not alkyl, or where R.sup.1 is not alkyl while R.sup.2 is optionally substituted phenyl.Type: GrantFiled: October 26, 1987Date of Patent: October 17, 1989Assignee: Bayer AktiengesellschaftInventors: Engelbert Kule, Alfons Adler
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Patent number: 4871856Abstract: Compounds having the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.n --wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2-5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are carbonyl; and R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.m --wherein m is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 - C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.Type: GrantFiled: November 7, 1988Date of Patent: October 3, 1989Assignee: Stauffer Chemical CompanyInventor: Jeff K. Curtis
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Patent number: 4871857Abstract: Compounds having the formula ##STR1## wherein R is halogen; C.sub.1-C.sub.2 alkyl; C.sub.1-C.sub.2 alkoxy; nitro; cyano; C.sub.1-C.sub.2 haloalkyl; or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1-C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2-5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 aklyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are carbonyl; and R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.m -- wherein m is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.Type: GrantFiled: November 7, 1988Date of Patent: October 3, 1989Assignee: Stuaffer Chemical CompanyInventor: Jeff K. Curtis
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Patent number: 4868313Abstract: The invention relates to 4-hydroxy pyrrolidone derivatives which help restore learning and memory difficulties associated with ageing. A compound of the invention is 2-(4-hydroxy-2-oxo-1-pyrrolidineacetamido)acetamide.Type: GrantFiled: January 23, 1989Date of Patent: September 19, 1989Assignee: I.S.F. Societa Per AzioniInventors: Mario Pinza, Carlo Farina, Silvano Banfi, Ugo Pfeiffer
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Patent number: 4855451Abstract: 4-Benzyloxy-3-pyrrolin-2-one is a new valuable intermediate product for the production of tetramic acid. Processes are described for the production of such intermediate as well as the production of tetramic acid.Type: GrantFiled: June 10, 1987Date of Patent: August 8, 1989Assignee: Lonza Ltd.Inventor: Thomas Meul
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Patent number: 4849528Abstract: 4-Benzyloxy-3-pyrrolin-2-on-1-yl acetamide is an advantageous intermediate product for the production of pharmaceutically effective 4-hydroxypyrrolidin-2-1-yl acetamide. Processes for the production of the intermediate product as well as the active substance are described.Type: GrantFiled: June 10, 1987Date of Patent: July 18, 1989Assignee: Lonza Ltd.Inventor: Thomas Meul
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Patent number: 4843166Abstract: 4-Benzyloxy-3-pyrrolin-2-on-1-yl acetamide is an advantageous intermediate product for the production of pharmaceutically effective 4-hydroxypyrrolidin-2-1-yl acetamide. Processes for the production of the intermediate product as well as the active substance are described.Type: GrantFiled: April 14, 1988Date of Patent: June 27, 1989Assignee: Lonza Ltd.Inventor: Thomas Meul
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Patent number: 4824966Abstract: Process for the production of 4-hydroxy-2-oxo-pyrrolidin-1-yl acetamide. A 4-(C.sub.1 -C.sub.2)-alkoxy-3-pyrrolin-2-on-1-yl-acetic acid (C.sub.1 -C.sub.4)-alkyl ester of the formula: ##STR1## wherein R.sub.1 is alkyl having 1 or 2 C atoms and R.sub.2 is alkyl having 1 to 4 C atoms, is reacted with either trichloromethylsilane in the presence of an alkali iodide or in an acid anhydrous medium to a 2,4-dioxo-pyrrolidin-1-yl-acetic acid (C.sub.1 -C.sub.4)-alkyl ester. The latter is optionally isolated and then hydrogenated with sodium borohydride to a 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetic acid (C.sub.1 -C.sub.4)-alkyl ester. Finally, the 4-hydroxy-2-oxo-pyrrolidin-1-yl-acetic acid (C.sub.1 -C.sub.4)-alkyl ester is converted by amidation with ammonia to the desired end product.Type: GrantFiled: May 4, 1988Date of Patent: April 25, 1989Assignee: Lonza Ltd.Inventors: Thomas Meul, John McGarrity
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Patent number: 4824861Abstract: The invention relates to 4-hydroxy pyrrolidone derivatives which help restore learning and memory difficulties associated with ageing. A compound of the invention is 2-(4-hydroxy-2-oxo-1-pyrrolidineacetamido)acetamide.Type: GrantFiled: December 11, 1987Date of Patent: April 25, 1989Assignee: ISF Societa Per AzioniInventors: Mario Pinza, Carlo Farina, Silvano Banfi, Ugo Pfeiffer
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Patent number: 4812578Abstract: 4-Benzyloxy-3-pyrrolin-2-one is a new valuable intermediate product for the production of tetramic acid. Processes are described for the production of such intermediate as well as the production of tetramic acid.Type: GrantFiled: April 28, 1988Date of Patent: March 14, 1989Assignee: Lonza Ltd.Inventor: Thomas Meul
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Patent number: 4806604Abstract: The present invention discloses a new class of calcium chelating compounds which have a decreased affinity for calcium following illumination. These new compounds contain a photolabile nitrobenzyl derivative coupled to a tetracarboxylate Ca.sup.2+ chelating parent compound having the octacoordinate chelating groups characteristic of EGTA or BAPTA. However unlike EGTA or BAPTA-like compounds, in which the two halves of the chelator are linked by a simple 1,2-ethanediyl moiety, the compounds of the present invention modify the stereochemical conformation of this linkage by adding bulky substituents or incorporating the linkage into a carbocyclic or heterocyclic ring. In a first form, the new compounds are comprised of a BAPTA-like chelator coupled to a single 2-nitrobenzyl derivative, which in turn is a photochemical precursor of a 2-nitrosobenzophenone.Type: GrantFiled: May 13, 1987Date of Patent: February 21, 1989Assignee: Regents of the University of CaliforniaInventors: Roger Yonchien Tsien, Stephen R. Adams
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Patent number: 4802913Abstract: 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: August 5, 1986Date of Patent: February 7, 1989Assignee: Imperial Chemical Industries PLCInventors: John Clough, Christopher R. A. Godfrey
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Patent number: 4797496Abstract: Process for preparing pyrrolidinone derivatives of (1) ##STR1## in which R is hydrogen, alkyl or acyl characterized in that a compound of (2) ##STR2## wherein R.sup.1 is hydrogen and R.sup.2 is benzyl or substituted benzyl, or R.sup.1 and R.sup.2 can together form a group ##STR3## where R.sup.4 and R.sup.5 are independently hydrogen, alkyl, phenyl or optionally substituted aryl or together are 1,4-butylene or 1,5-pentylene; R.sup.3 is hydrogen or straight or branched alkyl of 1 to 4 carbon atoms; and X is alkyl subjected to N-deprotection and the deprotected intermediate is cyclized intramolecularly.The deprotected intermediates can be isolated as acid-addition salts.Type: GrantFiled: March 8, 1988Date of Patent: January 10, 1989Assignee: I.S.F. Societa Per AzioniInventors: Mario Pinza, Ugo C. Pfeiffer
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Patent number: 4788294Abstract: Process for the production of 4-alkoxy-3-pyrrolin-2-ones, which are preferred intermediate products for the production of cerebrally-active pharmaceutical products.Type: GrantFiled: March 14, 1988Date of Patent: November 29, 1988Assignee: Lonza Ltd.Inventors: Laurent Duc, John McGarrity, Thomas Meul
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Patent number: 4785109Abstract: These is described a process for producing sulfonylureas of the formula ##STR1## wherein G is an unsubstituted or substituted furanyl, thienyl, pyrrolyl, pyridinyl or phenyl radical,X is alkyl, haloalkyl, alkoxy, alkylthio, halogen, haloalkoxy, alkylamino or dialkylamino,Y is alkyl, alkoxy or haloalkoxy,Z is a nitrogen atom or the methyne group --CH.dbd..This novel process comprises reacting a sulfonamide of the formulaG--SO.sub.2 --NH.sub.2,in the presence of a base, with a chloroformic acid ester of the formulaCl--CO--Q--T,or a sulfonyl chloride of the formulaG--SO.sub.2 Cl,in the presence of a base, with a urethane of the formulaH.sub.2 N--CO--Q--T;and converting the formed carbamate of the formulaG--SO.sub.2 --NH--CO--Q--Tby reaction with an amine of the formula ##STR2## into the sulfonylurea of the above formula. There are also described novel sulfonylcarbamates of the above formula as intermediates.Type: GrantFiled: January 30, 1987Date of Patent: November 15, 1988Assignee: Ciba-Geigy CorporationInventors: Willy Meyer, Werner Fory, Werner Topfl
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Patent number: 4760077Abstract: There is described the use of pyrrothine derivatives of the general formula I ##STR1## wherein R.sub.1 and R.sub.3 signify hydrogen or methyl, R.sub.2 hydrogen, methyl or an acyl group with 1 to 5 carbon atoms and X and Y signify hydrogen, an equivalent of a physiolgically acceptable cation or together a single bond, for the inhibition of the allergen-induced degranulation of peripheral leukocytes.Type: GrantFiled: May 15, 1986Date of Patent: July 26, 1988Assignee: Boehringer Mannheim GmbHInventors: Peter Stahl, Hans Seidel, Herbert Von der Eltz, Otto-Henning Wilhelms, Androniki Roesch
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Patent number: 4747965Abstract: Disclosed are additives which are useful as dispersants in lubricating oils, gasolines, marine crankcase oils and hydraulic oils. In particular, disclosed are multiply adducted alkenyl or alkyl succinimides which contain carbamate functionalities.Type: GrantFiled: August 15, 1986Date of Patent: May 31, 1988Assignee: Chevron Research CompanyInventors: Robert H. Wollenberg, Frank Plavac
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Patent number: 4746446Abstract: Disclosed are additives which are useful as dispersants in lubricating oils, gasolines, marine crankcase oils and hydraulic oils. In particular, disclosed are polyamino alkenyl or alkyl succinimides which contain carbamate functionalities.Type: GrantFiled: August 27, 1987Date of Patent: May 24, 1988Assignee: Chevron Research CompanyInventors: Robert H. Wollenberg, Frank Plavac, Timothy R. Erdman
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Patent number: 4739076Abstract: An amino blocking reagent, 1-isopropyl-3-ethoxy-4-nitro-2-oxo-3-pyrroline has been obtained. The new reagent is water soluble. It has yielded an N-protected glycine active ester with solubiity appropriate for reaction with both peptides and proteins. N-hydroxysuccinimide esters of N-i-NOPY- and N-c-NOPY-glycines were prepared. The N-hydroxysuccinimide active esters were produced by treatment with dicyclohexylcarbodimide (DCC) and N-hydroxysuccinimide in tetrahydrofuran (THF). The new reagents for glycine attachment are stable crystalline compounds. These active esters were used to attach glycine residues to a dipeptide and a protein by the salt-coupling procedure.Type: GrantFiled: March 15, 1985Date of Patent: April 19, 1988Inventor: Philip L. Southwick
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Patent number: 4731455Abstract: A process for the preparation of a C(3)-C(4)-transconfigurated .gamma.-butyrolactam of the formula (I) ##STR1## in which R.sup.1 represents hydrogen or alkyl, aryl or aralkyl with in each case up to 10 carbon atoms andR.sup.2 and R.sup.3 are identical or different and represent hydrogen, alkyl, aryl, aralkyl, alkoxy, aryloxy or aralkoxy with in each case up to 10 carbon atoms, acyl with up to 18 carbon atoms, trifluoromethyl, trifluoromethoxy, nitro, hydroxyl, halogen, amino, carboxyl, sulpho, dialkylamino with up to 4 carbon atoms in the alkyl groups or acylamino with up to 18 carbon atoms,in the form of their isomers, isomer mixtures, racemates or optical antipodes, comprising oxidizing a compound of the formula (II) ##STR2## in which R.sup.1, R.sup.2 and R.sup.3 have the above-mentioned meanings, in an inert organic solvent in the presence of a base. Such .gamma.-butyrolactams have an antiamnesic action.Type: GrantFiled: October 1, 1986Date of Patent: March 15, 1988Assignees: Bayer Aktiengesellschaft, Chinese Academy of Medical SciencesInventor: Wolfgang Hartwig
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Patent number: 4731369Abstract: Amides and esters of 2-[N-(hydroxypiperidinoalkyl) and (hydroxypyrrolidinoalkyl) aminosulfonyl]-6-nitrobenzoic acids are disclosed to have activity in increasing the sensitivity of hypoxic tumor cells to therapeutic radiation. Also disclosed are methods of preparing such compounds, pharmaceutical compositions including such compounds and methods of treating patients in need of therapeutic radiation with effective amounts of such compounds.Type: GrantFiled: June 26, 1987Date of Patent: March 15, 1988Assignee: Merck & Co. Inc.Inventors: Edward L. Engelhardt, Walfred S. Saari
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Patent number: 4731456Abstract: A new synthetic route to clausenamide having the formula ##STR1## has been found. It has been found that a compound of the formula ##STR2## can be oxidized to provide the stereochemically correctly configured product, clasuenamide. A number of new compounds useful in the total synthesis of clausenamide have also been found. These compounds have the general formula ##STR3## wherein R is ##STR4## and CH.sub.2 OH.Type: GrantFiled: October 3, 1986Date of Patent: March 15, 1988Assignees: Bayer Aktiengesellschaft, Chinese Academy of Medical SciencesInventor: Wolfgang Hartwig
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Patent number: 4731454Abstract: A method for producing a lactam having the formula: ##STR1## wherein R.sup.1 is a hydrogen atom, or a straight chain or branched chain alkyl group having from 1 to 5 carbon atoms, and R.sup.2 is an organic group having at least 2 carbon atoms, and connected at both ends to the cyclic acid imide group, which comprises reducing a cyclic acid imide having the formula: ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, or its precursor, with hydrogen by means of a cobalt-based catalyst comprising (a) cobalt and (b) at least one modifier component selected from the group consisting of molybdenum, tungsten and rhenium.Type: GrantFiled: May 29, 1987Date of Patent: March 15, 1988Assignee: Mitsubishi Chemical Industries LimitedInventors: Masayuki Otake, Isamu Fukushima
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Patent number: 4709052Abstract: 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: May 16, 1984Date of Patent: November 24, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroki Tomioka, Tadashi Ooishi, Junya Takahashi, Mitsuru Sasaki, Naonori Hirata
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Patent number: 4692532Abstract: Substituted (4-hydroxyphenylthioalkyl) derivatives of the formula ##STR1## are prepared by the reaction of the appropriate ring and hydroxybenzene thiol compounds and are useful stabilizers of organic materials.Type: GrantFiled: November 23, 1984Date of Patent: September 8, 1987Assignee: Ciba-Geigy CorporationInventors: John D. Spivack, Ramanathan Ravichandran, Stephen D. Pastor
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Patent number: 4686296Abstract: A process for producing oxiracetam (4-hydroxy-2-oxo-1-pyrrolidineacetamide) useful as an agent for improving brain metabolism, under mild conditions and in a single process is provided, this process comprises reacting glycinamide with a butyric acid ester expressed by the formula ##STR1## wherein A represents a halogen atom or an epoxy group, B represents hydroxyl group, but when A is an epoxy group, A and B together form an epoxy group, and R represents an alkyl group.Type: GrantFiled: July 22, 1986Date of Patent: August 11, 1987Assignee: Denki Kagaku Kogyo Kabushiki KaishaInventors: Shinobu Iriuchijima, Hirohiko Kobayashi, Kyoji Aoki, Takeshi Oda, Masayuki Shinoyama, Yoshifumi Nosaka
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Patent number: 4680414Abstract: The invention relates to novel substituted-3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones, their analogs and their salts. These compounds are synthesized by methods selected from a number of synthetic routes depending on the particular structure, choice of intermediate or preferred reaction sequence. The compounds are useful for the treatment and prevention of injury to the brain and of edema due to head trauma, stroke (particularly ischemic), arrested breathing, cardiac arrest, Reye's syndrome, cerebral thrombosis, cerebral embolism, cerebral hemorrhage, cerebral tumors, encephalomyelitis, spinal cord injury, hydrocephalus, post-operative brain injury trauma, edema due to cerebral infections and various brain concussions.Type: GrantFiled: February 20, 1986Date of Patent: July 14, 1987Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
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Patent number: 4678826Abstract: Substituted-(aminoxy)-pyrrolidine-2,5-dione derivatives of the formula ##STR1## are prepared by the reaction of the appropriate maleimide and hydroxylamine compounds and are useful as stabilizers for organic polymers.Type: GrantFiled: January 24, 1986Date of Patent: July 7, 1987Assignee: Ciba-Geigy CorporationInventors: Stephen D. Pastor, Edward T. Hessell
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Patent number: 4677114Abstract: Novel derivatives of substituted pyrrolizine diones and the pharmaceutically acceptable salts and esters thereof, have therapeutic utility for reducing amnesia induced by electroconvulsive shock and for treating senility.Type: GrantFiled: November 22, 1985Date of Patent: June 30, 1987Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, Anthony J. Thomas
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Patent number: 4664827Abstract: Disclosed herein are additives which are useful as dispersants and detergents in lubricating oils and fuels.Type: GrantFiled: September 12, 1986Date of Patent: May 12, 1987Assignee: Chevron Research CompanyInventor: Thomas F. Buckley
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Patent number: 4663319Abstract: Novel thioketene derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen atom, an alkyl group, a lower alkenyl group, a phenyl group or a group of the formula: --B--Y;Y is a nitrogen-containing monocyclic heterocyclic group or a substituted or unsubstituted phenyl group;B is a straight or branched lower alkylene group;R.sup.2 and R.sup.3 are both a lower alkyl group or are combined together to form a group of the formula: --CH.sub.2 CH.sub.2 -- or --CH.dbd.CH--;R.sup.4 is hydrogen atom, a lower alkyl group or a (lower alkoxy)carbonyl group;A is a group of the formula: --(CH.sub.2).sub.n -- or --CH(COOR.sup.5)--;n is an integer of 0, 1 or 2 andR.sup.5 is a lower alkyl group,are disclosed. The compound (I) is useful as an agent for treating and protecting various liver diseases.Type: GrantFiled: January 7, 1985Date of Patent: May 5, 1987Assignee: Tanabe Seiysku Co., Ltd.Inventors: Ikuo Iijima, Koichi Homma, Yutaka Saiga, Yuzo Matsuoka, Mamoru Matsumoto
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Patent number: 4650878Abstract: 2-(2-Oxo-1-pyrrolidinyl)acetic acids of the formula ##STR1## wherein R.sup.2 is hydrogen or lower alkyl and R.sup.11 is hydrogen, lower alkanoyl or another group readily cleavable by means of ammonia, are described. The compounds of formula III of the invention are useful to prepare the compound of formula I of the invention which are useful as medicaments, for example, in the form of pharmaceutical preparations.Type: GrantFiled: June 25, 1984Date of Patent: March 17, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Werner Aschwanden, Emilio Kyburz
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Patent number: 4638060Abstract: Antibacterial activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.Type: GrantFiled: April 29, 1985Date of Patent: January 20, 1987Assignee: E. R. Squibb & Sons, Inc.Inventors: Joseph E. Sundeen, William H. Koster, Robert Zahler
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Patent number: 4629797Abstract: A process for preparing compounds (1) ##STR1## where Y is NR.sup.1 R.sup.2 or OR, R.sup.1 and R.sup.2 are hydrogen or C.sub.1-3 alkyl, and R is C.sub.1-3 alkyl, which comprises protecting the hydroxy group of a compound (2) ##STR2## cyclising the product under basic conditions and removing the protecting group.Type: GrantFiled: March 29, 1985Date of Patent: December 16, 1986Assignee: I.S.F. Societa per AzioniInventors: Mario Pinza, Ugo C. Pfeiffer
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Patent number: 4608185Abstract: Disclosed herein are additives which are useful as dispersants and detergents in lubricating oils and fuels.Type: GrantFiled: December 31, 1985Date of Patent: August 26, 1986Assignee: Chevron Research CompanyInventor: Thomas F. Buckley
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Patent number: 4605664Abstract: The invention relates to novel substituted-3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones, their analogs and their salts. These compounds are synthesized by methods selected from a number of synthetic routes depending on the particular structure, choice of intermediate or preferred reaction sequence. The compounds are useful for the treatment and prevention of injury to the brain and of edema due to head trauma, stroke (particularly ischemic), arrested breathing, cardiac arrest, Reye's syndrome, cerebral thrombosis, cerebral embolism, cerebral hemorrhage, cerebral tumors, encephalomyelitis, spinal cord injury, hydrocephalus, post-operative brain injury trauma, edema due to cerebral infections and various brain concussions.Type: GrantFiled: May 1, 1984Date of Patent: August 12, 1986Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
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Patent number: 4605663Abstract: The invention relates to novel substituted-3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones, their analogs and their salts. These compounds are synthesized by methods selected from a number of synthetic routes depending on the particular structure, choice of intermediate or preferred reaction sequence. The compounds are useful for the treatment and prevention of injury to the brain and of edema due to head trauma, stroke (particularly ischemic), arrested breathing, cardiac arrest, Reye's syndrome, cerebral thrombosis, cerebral embolism, cerebral hemorrhage, cerebral tumors, encephalomyelitis, spinal cord injury, hydrocephalus, post-operative brain injury trauma, edema due to cerebral infections and various brain concussions.Type: GrantFiled: May 1, 1984Date of Patent: August 12, 1986Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
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Patent number: 4596821Abstract: The invention relates to novel substituted-3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones, their analogs and their salts. These compounds are synthesized by methods selected from a number of synthetic routes depending on the particular structure, choice of intermediate or preferred reaction sequence. The compounds are useful for the treatment and prevention of injury to the brain and of edema due to head trauma, stroke (particularly ischemic), arrested breathing, cardiac arrest, Reye's syndrome, cerebral thrombosis, cerebral embolism, cerebral hemorrhage, cerebral tumors, encephalomyelitis, spinal cord injury, hydrocephalus, post-operative brain injury trauma, edema due to cerebral infections and various brain concussions.Type: GrantFiled: May 1, 1984Date of Patent: June 24, 1986Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
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Patent number: 4585881Abstract: 2,5-Dihydro-5-aryliminopyrrole derivatives of the formula ##STR1## where R.sup.1 is hydrogen or alkyl, R.sup.2 and R.sup.3 are each alkyl, and Ar is unsubstituted or substituted aryl, are used for controlling undesirable plant growth.Type: GrantFiled: February 29, 1984Date of Patent: April 29, 1986Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Bruno Wuerzer
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Patent number: 4476308Abstract: Pyrrolidine derivatives of the formula ##STR1## wherein R.sup.1 is hydrogen or lower alkanoyl, R.sup.2 is hydrogen or lower alkyl and R.sup.3 is hydrogen, lower alkyl or a group of the formula --(CH.sub.2).sub.n --NR.sup.4 R.sup.5, wherein n is a whole number of 2 to 4 and R.sup.4 and R.sup.5 each, independently, are hydrogen or lower alkyl, or R.sup.4 and R.sup.5 taken together with the nitrogen atom are a pyrrolidinyl, piperidinyl, piperazinyl or morpholinyl group which is optionally substituted by one or two lower alkyl groups, enantiomers thereof, and acid addition salts of compounds of formula I and their enantiomers which are basic, are useful in the control or prevention of cerebral insufficiency or in the improvement of intellectual capacity. The compounds of formula I of the invention can be prepared starting from starting materials hereinafter described, and are useful as medicaments, for example, in the form of pharmaceutical preparations.Type: GrantFiled: June 20, 1983Date of Patent: October 9, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Werner Aschwanden, Emilio Kyburz
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Patent number: 4463177Abstract: m-Hydroxyphenyl substituted compounds of formula ##STR1## where R is an organic radical and R.sup.1 is hydroen or an organic radical are prepared by dehydrohalogenating a compound of formula ##STR2## (where X is chlorine or bromine, and R and R.sup.1 have the above meanings). Preferred novel starting materials of formula (II) are of the formula ##STR3## (where R.sup.1 and X are as above, n is 2,3 or 4, R.sup.2 is hydrogen or lower alkyl and R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl(lower)alkyl or aryl(lower)alkyl).Type: GrantFiled: November 26, 1982Date of Patent: July 31, 1984Assignee: John Wyeth & Brother LimitedInventor: Robin G. Shepherd