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)
  • Patent number: 4935440
    Abstract: 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: Grant
    Filed: February 21, 1989
    Date of Patent: June 19, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Robert Greenhouse, John Young, D. V. Krishna Murthy
  • Patent number: 4925868
    Abstract: 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: Grant
    Filed: August 12, 1987
    Date of Patent: May 15, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Minoru Hirata
  • Patent number: 4913721
    Abstract: 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: Grant
    Filed: October 31, 1988
    Date of Patent: April 3, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey
  • Patent number: 4886908
    Abstract: (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: Grant
    Filed: February 29, 1988
    Date of Patent: December 12, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventor: Johannes Haeusler
  • Patent number: 4880940
    Abstract: 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: Grant
    Filed: July 22, 1988
    Date of Patent: November 14, 1989
    Assignee: Lonza Ltd.
    Inventors: Thomas Muel, Leander Tenud, Laurent Duc, John McGarrity
  • Patent number: 4879393
    Abstract: 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: Grant
    Filed: April 14, 1988
    Date of Patent: November 7, 1989
    Assignee: Lonza Ltd.
    Inventor: Thomas Meul
  • Patent number: 4879390
    Abstract: 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: Grant
    Filed: April 27, 1988
    Date of Patent: November 7, 1989
    Assignees: Chinese Academy of Medical Sciences, Bayer Aktiengesellschaft
    Inventors: Yen-rong Chen, Ming-he Yang, Liang Huang, Geng-tao Liu, Ulrich Benz
  • Patent number: 4877884
    Abstract: 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: Grant
    Filed: April 11, 1989
    Date of Patent: October 31, 1989
    Assignee: Lonza Ltd.
    Inventor: Thomas Meul
  • Patent number: 4877887
    Abstract: 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: Grant
    Filed: May 2, 1988
    Date of Patent: October 31, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Wolfgang Rohr
  • Patent number: 4874874
    Abstract: 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: Grant
    Filed: October 26, 1987
    Date of Patent: October 17, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Engelbert Kule, Alfons Adler
  • Patent number: 4871856
    Abstract: 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: Grant
    Filed: November 7, 1988
    Date of Patent: October 3, 1989
    Assignee: Stauffer Chemical Company
    Inventor: Jeff K. Curtis
  • Patent number: 4871857
    Abstract: 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: Grant
    Filed: November 7, 1988
    Date of Patent: October 3, 1989
    Assignee: Stuaffer Chemical Company
    Inventor: Jeff K. Curtis
  • Patent number: 4868313
    Abstract: 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: Grant
    Filed: January 23, 1989
    Date of Patent: September 19, 1989
    Assignee: I.S.F. Societa Per Azioni
    Inventors: Mario Pinza, Carlo Farina, Silvano Banfi, Ugo Pfeiffer
  • Patent number: 4855451
    Abstract: 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: Grant
    Filed: June 10, 1987
    Date of Patent: August 8, 1989
    Assignee: Lonza Ltd.
    Inventor: Thomas Meul
  • Patent number: 4849528
    Abstract: 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: Grant
    Filed: June 10, 1987
    Date of Patent: July 18, 1989
    Assignee: Lonza Ltd.
    Inventor: Thomas Meul
  • Patent number: 4843166
    Abstract: 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: Grant
    Filed: April 14, 1988
    Date of Patent: June 27, 1989
    Assignee: Lonza Ltd.
    Inventor: Thomas Meul
  • Patent number: 4824966
    Abstract: 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: Grant
    Filed: May 4, 1988
    Date of Patent: April 25, 1989
    Assignee: Lonza Ltd.
    Inventors: Thomas Meul, John McGarrity
  • Patent number: 4824861
    Abstract: 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: Grant
    Filed: December 11, 1987
    Date of Patent: April 25, 1989
    Assignee: ISF Societa Per Azioni
    Inventors: Mario Pinza, Carlo Farina, Silvano Banfi, Ugo Pfeiffer
  • Patent number: 4812578
    Abstract: 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: Grant
    Filed: April 28, 1988
    Date of Patent: March 14, 1989
    Assignee: Lonza Ltd.
    Inventor: Thomas Meul
  • Patent number: 4806604
    Abstract: 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: Grant
    Filed: May 13, 1987
    Date of Patent: February 21, 1989
    Assignee: Regents of the University of California
    Inventors: Roger Yonchien Tsien, Stephen R. Adams
  • Patent number: 4802913
    Abstract: 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: Grant
    Filed: August 5, 1986
    Date of Patent: February 7, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: John Clough, Christopher R. A. Godfrey
  • Patent number: 4797496
    Abstract: 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: Grant
    Filed: March 8, 1988
    Date of Patent: January 10, 1989
    Assignee: I.S.F. Societa Per Azioni
    Inventors: Mario Pinza, Ugo C. Pfeiffer
  • Patent number: 4788294
    Abstract: 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: Grant
    Filed: March 14, 1988
    Date of Patent: November 29, 1988
    Assignee: Lonza Ltd.
    Inventors: Laurent Duc, John McGarrity, Thomas Meul
  • Patent number: 4785109
    Abstract: 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: Grant
    Filed: January 30, 1987
    Date of Patent: November 15, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Meyer, Werner Fory, Werner Topfl
  • Patent number: 4760077
    Abstract: 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: Grant
    Filed: May 15, 1986
    Date of Patent: July 26, 1988
    Assignee: Boehringer Mannheim GmbH
    Inventors: Peter Stahl, Hans Seidel, Herbert Von der Eltz, Otto-Henning Wilhelms, Androniki Roesch
  • Patent number: 4747965
    Abstract: 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: Grant
    Filed: August 15, 1986
    Date of Patent: May 31, 1988
    Assignee: Chevron Research Company
    Inventors: Robert H. Wollenberg, Frank Plavac
  • Patent number: 4746446
    Abstract: 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: Grant
    Filed: August 27, 1987
    Date of Patent: May 24, 1988
    Assignee: Chevron Research Company
    Inventors: Robert H. Wollenberg, Frank Plavac, Timothy R. Erdman
  • Patent number: 4739076
    Abstract: 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: Grant
    Filed: March 15, 1985
    Date of Patent: April 19, 1988
    Inventor: Philip L. Southwick
  • Patent number: 4731455
    Abstract: 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: Grant
    Filed: October 1, 1986
    Date of Patent: March 15, 1988
    Assignees: Bayer Aktiengesellschaft, Chinese Academy of Medical Sciences
    Inventor: Wolfgang Hartwig
  • Patent number: 4731369
    Abstract: 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: Grant
    Filed: June 26, 1987
    Date of Patent: March 15, 1988
    Assignee: Merck & Co. Inc.
    Inventors: Edward L. Engelhardt, Walfred S. Saari
  • Patent number: 4731456
    Abstract: 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: Grant
    Filed: October 3, 1986
    Date of Patent: March 15, 1988
    Assignees: Bayer Aktiengesellschaft, Chinese Academy of Medical Sciences
    Inventor: Wolfgang Hartwig
  • Patent number: 4731454
    Abstract: 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: Grant
    Filed: May 29, 1987
    Date of Patent: March 15, 1988
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Masayuki Otake, Isamu Fukushima
  • Patent number: 4709052
    Abstract: 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: Grant
    Filed: May 16, 1984
    Date of Patent: November 24, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroki Tomioka, Tadashi Ooishi, Junya Takahashi, Mitsuru Sasaki, Naonori Hirata
  • Patent number: 4692532
    Abstract: 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: Grant
    Filed: November 23, 1984
    Date of Patent: September 8, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: John D. Spivack, Ramanathan Ravichandran, Stephen D. Pastor
  • Patent number: 4686296
    Abstract: 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: Grant
    Filed: July 22, 1986
    Date of Patent: August 11, 1987
    Assignee: Denki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Shinobu Iriuchijima, Hirohiko Kobayashi, Kyoji Aoki, Takeshi Oda, Masayuki Shinoyama, Yoshifumi Nosaka
  • Patent number: 4680414
    Abstract: 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: Grant
    Filed: February 20, 1986
    Date of Patent: July 14, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
  • Patent number: 4678826
    Abstract: 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: Grant
    Filed: January 24, 1986
    Date of Patent: July 7, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, Edward T. Hessell
  • Patent number: 4677114
    Abstract: 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: Grant
    Filed: November 22, 1985
    Date of Patent: June 30, 1987
    Assignee: Warner-Lambert Company
    Inventors: Donald E. Butler, Anthony J. Thomas
  • Patent number: 4664827
    Abstract: Disclosed herein are additives which are useful as dispersants and detergents in lubricating oils and fuels.
    Type: Grant
    Filed: September 12, 1986
    Date of Patent: May 12, 1987
    Assignee: Chevron Research Company
    Inventor: Thomas F. Buckley
  • Patent number: 4663319
    Abstract: 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: Grant
    Filed: January 7, 1985
    Date of Patent: May 5, 1987
    Assignee: Tanabe Seiysku Co., Ltd.
    Inventors: Ikuo Iijima, Koichi Homma, Yutaka Saiga, Yuzo Matsuoka, Mamoru Matsumoto
  • Patent number: 4650878
    Abstract: 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: Grant
    Filed: June 25, 1984
    Date of Patent: March 17, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Aschwanden, Emilio Kyburz
  • Patent number: 4638060
    Abstract: Antibacterial activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: April 29, 1985
    Date of Patent: January 20, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joseph E. Sundeen, William H. Koster, Robert Zahler
  • Patent number: 4629797
    Abstract: 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: Grant
    Filed: March 29, 1985
    Date of Patent: December 16, 1986
    Assignee: I.S.F. Societa per Azioni
    Inventors: Mario Pinza, Ugo C. Pfeiffer
  • Patent number: 4608185
    Abstract: Disclosed herein are additives which are useful as dispersants and detergents in lubricating oils and fuels.
    Type: Grant
    Filed: December 31, 1985
    Date of Patent: August 26, 1986
    Assignee: Chevron Research Company
    Inventor: Thomas F. Buckley
  • Patent number: 4605664
    Abstract: 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: Grant
    Filed: May 1, 1984
    Date of Patent: August 12, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
  • Patent number: 4605663
    Abstract: 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: Grant
    Filed: May 1, 1984
    Date of Patent: August 12, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
  • Patent number: 4596821
    Abstract: 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: Grant
    Filed: May 1, 1984
    Date of Patent: June 24, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Otto W. Woltersdorf, Jr.
  • Patent number: 4585881
    Abstract: 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: Grant
    Filed: February 29, 1984
    Date of Patent: April 29, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Bruno Wuerzer
  • Patent number: 4476308
    Abstract: 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: Grant
    Filed: June 20, 1983
    Date of Patent: October 9, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Aschwanden, Emilio Kyburz
  • Patent number: 4463177
    Abstract: 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: Grant
    Filed: November 26, 1982
    Date of Patent: July 31, 1984
    Assignee: John Wyeth & Brother Limited
    Inventor: Robin G. Shepherd