Chalcogen Attached Indirectly To The Five-membered Hetero Ring By Acyclic Nonionic Bonding Patents (Class 548/551)
  • Patent number: 5576444
    Abstract: Cyclic imino derivatives of the formulaB--X.sub.2 --X.sub.1 --A--Y--E (I)wherein A, B, E, X.sub.1, X.sub.2 and Y are as defined herein, the stereoisomers, tautomers, mixtures and addition salts thereof, pharmaceutical compositions containing these compounds and processes for preparing them. The cyclic imino derivatives are useful as inhibitors of cell-cell and cell-matrix interactions, e.g., thrombocyte aggregation.
    Type: Grant
    Filed: April 26, 1993
    Date of Patent: November 19, 1996
    Assignee: Dr. Karl Thomae GmbH
    Inventors: Frank Himmelsbach, Austel Volkhard, Helmut Pieper, Guenter Linz, Johannes Weisenberger, Thomas Mueller
  • Patent number: 5571832
    Abstract: Compounds comprising a pyrrolidinyl ring are disclosed for use in the treatment of cerebral ischemia.
    Type: Grant
    Filed: June 20, 1994
    Date of Patent: November 5, 1996
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Brian R. de Costa, Wayne D. Bowen, Xiao-Shu He, Lilian Radesca, Kenner C. Rice
  • Patent number: 5563250
    Abstract: The present invention provides cleavable conjugates whose linkers contain a labile bond that is cleavable under a variety of mild conditions, including weakly acidic. Since the agent may be bonded directly to the linker, cleavage can result in release of native agent. The invention also provides methods for producing cleavable conjugates. Preferred agents include drugs, toxins, biological response modifiers, radiodiagnostic compounds, radiotherapeutic compounds, and derivatives thereof. The targeting molecule employed in the invention may be an intact molecule, a fragment thereof, or a functional equivalent thereof. In a particularly preferred embodiment, the targeting molecule is a monoclonal antibody directed towards a tumor-associated antigen in man. The invention further provides methods for delivering to the cytoplasm of a target cell an agent free of its targeting molecule carrier.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: October 8, 1996
    Assignee: NeoRx Corporation
    Inventors: Mark D. Hylarides, Ananthachari Srinivasan, Jeffrey N. Fitzner, Vivekananda M. Vrudhula
  • Patent number: 5547979
    Abstract: Derivatives of 2-pyrrolidinones are described which inhibit the production of TNF and are useful in the treatment of disease states mediated or exacerbated by TNF production.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: August 20, 1996
    Assignee: SmithKline Beecham
    Inventors: Siegfried B. Christensen, IV, Klaus M. Esser, Philip L. Simon
  • Patent number: 5539111
    Abstract: An enzymatic process employing pancreatin or choelsterol esterase for resolution of racemates of 4-aryl-2-oxo-pyrrolidine-3-carboxylic acid esters of general formula I ##STR1## in which X represents a carbon-carbon bond or an oxygen atom,R.sub.1 means a hydrocarbon radical optionally substituted by hydroxy groups, oxo groups and/or halogen atoms and/or interrupted by nitrogen atoms with at most 16 carbon atoms,R.sub.2 symbolizes an alkyl group with up to 4 carbon atoms andR.sub.3 represents an alkyl group with at most 6 carbon atoms is described.
    Type: Grant
    Filed: February 18, 1993
    Date of Patent: July 23, 1996
    Assignee: Schering Aktiengesellschaft
    Inventors: Karl Petzoldt, Ralph Schmiechen, Kurt Hamp, Matthias Gottwald
  • Patent number: 5529999
    Abstract: This invention provides certain sulfonamidoquinoxaline derivatives and methods for using them in the treatment of susceptible neoplasms in mammals. Also provided are certain novel pharmaceutical formulations employing these sulfonamidoquinoxaline derivatives, in combination with a carrier, diluent or excipient.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: June 25, 1996
    Assignee: Eli Lilly and Company
    Inventors: James E. Ray, John E. Toth
  • Patent number: 5523415
    Abstract: An antibacterial aminooxypyrrolidinylthiocarbapenem I, its production from the corresponding carbapenem V and thiol VI, its pharmaceutical formulation, and its use for combating bacteria are presented. ##STR1## (wherein R is optionally substituted amino; R.sup.1 is hydrogen or 1C to 5C alkyl; R.sup.2 is hydrogen or a conventional hydroxy protective group; R.sup.3 is hydrogen or an imino protective group or imino substituent; R.sup.4 is 1C to 5C alkylene; and R.sup.5 is hydrogen or a conventional carboxy protective group; X is a leaving group; R.sup.6 is hydrogen or a thiol protective group; and wavy lines each shows a bond in R or S configuration).
    Type: Grant
    Filed: July 12, 1994
    Date of Patent: June 4, 1996
    Assignee: Shionogi Seiyaku Kabushiki Kaisha
    Inventors: Yuji Sendo, Makoto Kii
  • Patent number: 5510379
    Abstract: .beta.-Carboxy sulfonates of the formula ##STR1## wherein R.sub.1 is aryl, R.sub.3 and R.sub.4 are hydrogen or alkyl, Y is -O-, -S-, or -NR.sub.2 -, and R.sub.5 is alkyl or aryl are potent inhibitors of the enzyme acyl CoA:cholesterol acyltransferase (ACAT) and are thus useful for treating hypercholesterolemia and atherosclerosis.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: April 23, 1996
    Assignee: Warner-Lambert Company
    Inventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
  • Patent number: 5489693
    Abstract: Cyclic imino derivatives of the formula ##STR1## wherein X and R.sub.a to R.sub.g are as defined herein, useful for their inhibitory effects on aggregation, pharmaceutical compositions containing the compounds and processes for preparing them.
    Type: Grant
    Filed: April 26, 1993
    Date of Patent: February 6, 1996
    Inventors: Guenter Linz, Volkhard Austel, Frank Himmelsbach, Johannes Weisenberger, Thomas Mueller, Helmut Pieper, Elke Seewaldt-Becker
  • Patent number: 5475118
    Abstract: Disclosed are a 1-phenylpyrrolidone derivative having optical activity and represented by the formula (I) ##STR1## wherein R represents an optionally substituted optically active .alpha.-phenylethylamino group, a 1-phenylpyrrolidone derivative represented by the formula (I-a) ##STR2## and processes for preparing the 1-phenylpyrrolidone derivatives represented by the formulas (I) and (I-a), respectively.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: December 12, 1995
    Assignee: Taiho Pharmaceutical Co., Ltd.
    Inventors: Shingo Yano, Tomoyasu Ohno, Kazuo Ogawa, Tetsuhiko Shirasaka
  • Patent number: 5461158
    Abstract: This invention offers novel compounds of the formula [I] which are useful for treatment of various immune diseases such as immunodeficiency and autoimmune diseases caused by immuno disorders, and synthetic intermediates thereof represented by the formula [II], ##STR1## wherein X is oxygen or NR.sup.7 and the R.sub.1 -R.sub.7 groups are defined in the specification.
    Type: Grant
    Filed: June 2, 1994
    Date of Patent: October 24, 1995
    Assignee: Santen Pharmaceutical Co., Ltd.
    Inventors: Shiro Mita, Yoichi Kawashima, Katsuhiko Nakata
  • Patent number: 5458660
    Abstract: The present invention is directed to the use of cyclic amide compounds containing multiple polyether alcohol backbones as additives in fuel compositions having a major amount of a mixture of hydrocarbons in the gasoline boiling range and a minor amount of one or more cyclic amide compounds containing multiple polyether backbones. The invention is also directed to the use of these cyclic amide alkoxylate compounds for decreasing intake valve deposits, controlling octane requirement increases and reducing octane requirement. The invention is further directed to cyclic amide compounds containing multiple polyether backbones.
    Type: Grant
    Filed: September 19, 1994
    Date of Patent: October 17, 1995
    Assignee: Shell Oil Company
    Inventors: Jiang-Jen Lin, Pen-Chung Wang, Sarah L. Weaver
  • Patent number: 5457122
    Abstract: The phenylalkan(en)oic acids of the formula: ##STR1## as defined herein, possess an antagonistic activity on leukotriene B.sub.4.
    Type: Grant
    Filed: July 13, 1993
    Date of Patent: October 10, 1995
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Mitoshi Konno, Takahiko Nakae, Nobuyuki Hamanaka
  • Patent number: 5455348
    Abstract: The invention relates to cyclic imino derivatives of general formulaB--X.sub.5 --X.sub.4 --X.sub.3 --X.sub.2 --X.sub.1 --A--Y--E(I)whereinA, B, E, X.sub.2 to X.sub.5 and Y are defined as in claim 1, the stereoisomers, tautomers, mixtures and salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable pharmacological properties, preferably aggregation-inhibiting effects, pharmaceutical compositions which contain these compounds and processes for preparing them.
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: October 3, 1995
    Assignee: Karl Thomae
    Inventors: Volkhard Austel, Wolfgang Eisert, Frank Himmelsbach, Guenter Linz, Thomas Mueller, Helmut Pieper, Johannes Weisenberger
  • Patent number: 5453516
    Abstract: A process for preparing 5-membered ring heterocycles of the general formula I ##STR1## where R.sup.1 is methyl or hydroxyethyl,R.sup.2,R.sup.3,R.sup.4,R.sup.5 and R.sup.6 are hydrogen, C.sub.1 - to C.sub.12 -alkyl, C.sub.2 - to C.sub.12 -alkenyl, aryl, C.sub.3 - to C.sub.8 -cycloalkyl, C.sub.1 - to C.sub.12 -alkoxy, halogen, C.sub.2 - to C.sub.20 -alkoxycarbonylalkyl, C.sub.2 - to C.sub.20 -alkylcarbonyloxy, formyl, C.sub.2 - to C.sub.20 -formylalkyl, benzoyl or --CH(OR.sup.3)(OR.sup.5), or R.sup.3 and R.sup.5 together are a C.sub.2 - to C.sub.7 -alkylene chain which is unsubstituted or monosubstituted to pentasubstituted by R.sup.4 or a .dbd.CH--CH.dbd.CH--CH.dbd. unit which is unsubstituted or monosubstituted to tetrasubstituted by R.sup.4,X is oxygen or N--R.sup.4by reacting 5-membered ring heterocycles of the general formula II ##STR2## where R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and X have the abovementioned meanings and Y is hydrogen, acetyl or C.sub.2 - to C.sub.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: September 26, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Rolf Pinkos
  • Patent number: 5420298
    Abstract: The invention concerns pyrrolidine derivatives of the formula ##STR1## wherein Ar.sup.1 is optionally-substituted phenyl, naphthyl or a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;A is a direct link to the group X or A is (1-4C)alkylene;X is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene, pyridinediyl, pyrimidinediyl, thiophendiyl, furandiyl or thiazolediyl;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl;R.sup.2 is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, halogeno-(1-4C)alkyl, halogeno-(2-4C)alkenyl, halogeno-(2-4C)alkynyl, (1-4C)alkoxy-(2-4C)alkyl, hydroxy-(2-4C)alkyl, cyano-(1-4C)alkyl, carboxy-(1-4C)alkyl, carbamoyl-(1-4C)alkyl, (1-4C)alkoxycarbonyl-(1-4C)alkyl, N-(1-4C)alkylcarbamoyl-(1-4C)alkyl or N,N-di-(1-4C)alkylcarbamoyl-(1-4C)alkyl; andn is 1 or 2 and each R.sup.
    Type: Grant
    Filed: September 1, 1993
    Date of Patent: May 30, 1995
    Assignees: Zeneca Limited, Zeneca Pharma S.A.
    Inventors: Philip N. Edwards, Michael S. Large
  • Patent number: 5420154
    Abstract: Derivatives of 2-pyrrolidinones are described which inhibit the production of TNF and are useful in the treatment of disease states mediated or exacerbated by TNF production.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: May 30, 1995
    Assignee: SmithKline Beecham Corp.
    Inventors: Siegfried B. Christensen, IV, Klaus M. Esser, Philip L. Simon
  • Patent number: 5385948
    Abstract: A solvent for producing emulsifiable concentrates from agriculturally active chemicals which are insoluble in water comprises an alkoxyalkyl lactam such as butoxy propyl pyrrolidone. An agriculturally active chemical and the alkoxyalkyl lactam are admixed optionally with co-solvents, emulsifiers and surfactants to produce a stable emulsifiable concentrate. The concentrate is dilutable with water at the point of use to produce either macro or micro emulsions which are themselves stable to assure even application.
    Type: Grant
    Filed: February 16, 1993
    Date of Patent: January 31, 1995
    Assignee: ISP Investments Inc.
    Inventors: Ratan K. Chaudhuri, Kolazi S. Narayanan, Lowell R. Anderson
  • Patent number: 5378724
    Abstract: Pesticidal substituted 2-arylpyrroles of the formula ##STR1## in which n represents 0, 1 or 2,Ar represents optionally substituted aryl,R.sup.1 and R.sup.2 independently of one another represent hydrogen or halogen, but at least one of the two radicals R.sup.1 or R.sup.2 represents halogen,R.sup.3 represents hydrogen, halogen or optionally substituted alkyl,X.sup.1 and X.sup.2 independently represent hydrogen or halogen andR.sup.4 represents hydrogen or ##STR2## (R.sup.5 and R.sup.6 having various meanings). The compounds of the formulas ##STR3## are also new.
    Type: Grant
    Filed: October 1, 1993
    Date of Patent: January 3, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Uhr, Albrecht Marhold, Stefan Bohm, Christoph Erdelen, Ulrike Wachendorff-Neumann, Wilhelm Stendel
  • Patent number: 5371238
    Abstract: A process for producing an azacycloalkane derivative represented by the following general formula (II): ##STR1## wherein m is an integer of from 1 to 3, n.sub.2 is an integer of from 2 to 10, andR represents an alkyl group having 3 to 12 carbon atoms,characterized by reacting a 1-(n-alkenyl)-azacycloalkan-2-one represented by the following general formula (I): ##STR2## wherein m is an integer of from 1 to 3, and n.sub.1 is an integer of from 0 to 8,with an alkyl mercaptan in the presence of a radical initiator in an organic solvent, treating the reaction mixture thus obtained with a reducing agent in a water-containing organic solvent, and then purifying the treated mixture by distillation.
    Type: Grant
    Filed: April 23, 1993
    Date of Patent: December 6, 1994
    Assignee: Hisamitsu Pharmaceutical Co., Inc.
    Inventors: Masaru Saita, Hisataka Inoue, Terumi Hachiya, Shigenori Yahiro, Kanji Noda
  • Patent number: 5312929
    Abstract: A herbicidal 2-oxo-3-pyrroline derivative having the formula: ##STR1## wherein X is a hydrogen atom or a halogen atom, Z is an oxygen atom or a group of the formula .dbd.N--OR.sup.1 (wherein R.sup.1 is a hydrogen atom, an alkyl group, a benzyl group or a phenyl group which is substituted by halogen atoms); and R is a hydrogen atom, an alkyl group, a benzyl group, a chloro-substituted benzyl group, a benzylidene methyl group, a group of the formula ##STR2## wherein Y is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group or an alkoxy group, and n is an integer of from 1 to 3, or a group of the formula ER.sup.2 wherein E is an oxygen atom, a sulfur atom or a group of the formula >N--R.sup.3, wherein R.sup.3 is a hydrogen atom, an alkyl group or an alkenyl group, and R.sup.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: May 17, 1994
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuyuki Ohba, Toshihiro Nagata, Akira Takeuchi, Shigehiko Tachikawa, Yasunori Ogawa
  • Patent number: 5302724
    Abstract: This invention provides certain sulfonamide compounds, formulations and method of use of certain sulfonamide compounds in treating susceptible neoplasms.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: April 12, 1994
    Assignee: Eli Lilly and Company
    Inventors: J. Jeffry Howbert, Fariborz Mohamadi, Michael M. Spees
  • Patent number: 5298628
    Abstract: Stereoselective process for the production of (4R)- or (4S)-4-aryl-2-pyrrolidinones as well as intermediate products and the stereoselective process for the production of the optically active intermediate compounds.
    Type: Grant
    Filed: July 1, 1992
    Date of Patent: March 29, 1994
    Assignee: Schering Aktiengesellschaft
    Inventors: Johann H. Mulzer, Ralf H. Zuhse
  • Patent number: 5272170
    Abstract: The present invention relates to new tetralones having the formula I: ##STR1## wherein: R.sup.1 and R.sup.2 represent hydrogen, halogen, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, trifluoromethyl, pentafluoroethyl, ethynyl, trimethylsilylethynyl, C.sub.1-4 alkylcarbonylamino being the amino optionally substituted by a C.sub.1-4 alkyl group; R.sup.3 is hydrogen or C.sub.1-4 alkyl, and R.sup.4 is C.sub.1-4 alkyl, or R.sup.3 and R.sup.4 together form a C.sub.2-5 polymethylene chain; either R.sup.5 represents hydroxyl, acetoxy or formyloxy and R.sup.6 and R.sup.7 are both hydrogen, or R.sup.5 together with R.sup.6 form a carbonyl group and R.sup.7 is hydrogen, or R.sup.5 and R.sup.7 together form a bond and R.sup.6 is hydrogen; R.sup.8 is, among others, 1,2-dihydro-2-oxo-1-pyridyl, 2,3-dihydro-1-oxo-1H-isoindol-2-yl, 2-oxo-1-pyrrolidinyl, 2-oxo-1-pyperidinyl. The invention also relates to a procedure for their preparation and to pharmaceutical compositions containing them.
    Type: Grant
    Filed: January 22, 1993
    Date of Patent: December 21, 1993
    Assignee: J. Uriach & Cia., S.A.
    Inventors: Carmen Almansa, Carmen Torres, Concepcion Gonzalez, Elena Carceller, Javier Bartroli
  • Patent number: 5270339
    Abstract: 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: Grant
    Filed: December 3, 1992
    Date of Patent: December 14, 1993
    Assignee: Kanagafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Kozo Yamamoto, Yoshihide Fuse, Hideyuki Kishida, Naoko Yasuhara, Toshiaki Miwa, Ikuo Katsumi, Takayoshi Hidaka
  • Patent number: 5256795
    Abstract: Novel pyrrolidinone derivatives of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, X and m have the meanings defined in the specification, useful as herbicides and nematicides.
    Type: Grant
    Filed: July 22, 1992
    Date of Patent: October 26, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Negele, Bernd Baasner, Heinz-Jurgen Bertram, Jurgen Hartwig
  • Patent number: 5218124
    Abstract: There are disclosed compounds of the formulaA(CH.sub.2).sub.n O--BwhereinA is a group having the formula ##STR1## wherein X is --N-- or ##STR2## Z is ##STR3## R.sup.1 is hydrogen, lower alkyl or phenyl; R.sup.2 is hydrogen or lower alkyl; orR.sup.1 and R.sup.2 taken together form a benzene ring, with the proviso that when X is --N--, Z is other than ##STR4## R.sup.3 is hydrogen or lower alkyl; n is 1-2;B is ##STR5## wherein Y is OR.sup.5 or N(OH)R.sup.8 ;R.sup.4 and R.sup.5 are each, independently, hydrogen or lower alkyl;R.sup.6 is hydrogen, halo or nitro;R.sup.7 is ##STR6## R.sup.
    Type: Grant
    Filed: June 1, 1992
    Date of Patent: June 8, 1993
    Assignee: American Home Products Corporation
    Inventors: Amedeo A. Failli, Anthony F. Kreft, III, John H. Musser, Annette L. Banker, James A. Nelson, Uresh S. Shah, Dennis M. Kubrak
  • Patent number: 5206386
    Abstract: N-substituted cyclic lactam esters are made from biologically active organic acids and N-haloalkyl substituted cyclic lactam, preferably N-chloromethyl pyrrolidone. Such esters provide slow release of the organic acids in situ through slow hydrolysis of the ester to release the organic acid and the N-alkyl substituted cyclic lactam. The esters are useable for delivering a large variety of biologically active organic acids in slow release fashion to target organisms and promote effective long term therapeutic treatment. In particular, an ester made from acetyl salicyclic acid and chloromethyl pyrrolidone provides a vehicle for dermal penetration and slow release of aspirin for long term treatment.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: April 27, 1993
    Assignee: ISP Investments Inc.
    Inventors: Kolazi S. Narayanan, Paul D. Taylor
  • Patent number: 5192759
    Abstract: 1,2,3,4-tetrahydronaphthlamines of formula (1) ##STR1## wherein R is H or OCH.sub.3 ; ##STR2## is either at 1 or 2 position R.sub.1 is H;R.sub.2 is selected from:L-prolyl, optionally N-substituted with acetyl or carbobenzoxy,L-pyroglutamyl,(pyrrolidin-2-one-1-yl)acetyl,3-carboxy-2-hydroxypropyl:or R.sub.1 and R.sub.2 taken together with the nitrogen atom form the ring ##STR3## wherein n=1,2,3 and R.sub.3 -H, OH are nootropic substances potent enhancers of learning processes and memory.Orally or parenterally administrable pharmaceutical compositions in unit dosage form comprise between about 100 and about 500 mg of a compound of formula (1).
    Type: Grant
    Filed: December 18, 1991
    Date of Patent: March 9, 1993
    Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.
    Inventors: Fabio Giannessi, Orlando Ghirardi, Domenico Misiti, Maria O. Tinti, Roberto Cozzolino
  • Patent number: 5175311
    Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: December 29, 1992
    Assignee: Research Corporation Technologies, Inc.
    Inventor: Michael F. Doyle
  • Patent number: 5145865
    Abstract: Phenylcarboxylic acid derivatives having a hetero ring in the substituent of the formula: ##STR1## wherein R.sup.1 is halogen, alkyl, cycloalkyl, hydroxy, alkoxy, phenoxy which has a substituent selected from halogen and alkyl, carboxyl, alkylsulfonyloxy, phenylsulfonyloxy optionally substituted by halogen, alkylsulfonyloxyalkoxy, amino, alkanoylamino, benzoylamino, alkenyloxy, phenylalkoxyalkoxy, hydroxyalkoxy, phenylalkoxy having optionally 1 to 3 substituents selected from halogen, alkyl and alkoxy, halogenoalkyl, cycloalkyloxy optionally substituted by hydroxy, alkoxy substituted by cycloalkyl having optionally hydroxy substituent, imidazolylalkyl or imidazolylalkoxy; k is 0 or 1 to 3; or (R.sup.1).sub.k is alkylenedioxy; A is alkylene or alkylenoxy; l is 0 or 1; B is methylene or carbonyl; m is 0 or 1; D is alkylene; E is alkylene or alkenylene; n is 0 or 1; and R.sup.
    Type: Grant
    Filed: April 19, 1990
    Date of Patent: September 8, 1992
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Setsuro Fujii, deceased, by Shinichiro Fujii, administrator, by Kaoruko Takada, administrator, Hiroyuki Kawamura, Shinichi Watanabe
  • Patent number: 5114466
    Abstract: 1-(3-Substituted benzyl)-3-halogeno-4-(1-halogenoalkyl)-2-pyrrolidinones of the general formula (I): ##STR1## where X represents a hydrogen atom or halogen atom, Y and Z each represents a chlorine atom or bromine atom, and R represents an alkyl group with 2 to 4 carbon atoms, are herbicides useful in rice paddy fields to control weeds therein, especially Echinochloa crusgalli and can be produced subjecting the corresponding 3-dihalogeno compounds to dehalogenation to remove one of the halogen atoms or by cyclizing a 2,2-dihalogenoacetamide derivative represented by the general formula (II) under the presence of an appropriate catalyst; ##STR2## in which X, Y, Z and R respectively have the same meanings as described above.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: May 19, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Kengo Oda, Koichi Moriyasu, Masao Hayashi, Makoto Nishida, Masami Oyamada, Akie Fujiwara, Junko Watanabe
  • Patent number: 5103007
    Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: April 7, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
  • Patent number: 5091407
    Abstract: Fungicidally active compounds of the formula ##STR1## and steroisomers thereof, wherein A is the group .dbd.CW--or a nitrogen atom, B is the group .dbd.CX--or a nitrogen atom, D is the group .dbd.CY--or a nitrogen atom, and E is the group .dbd.CZ--or a nitrogen atom, wherein W, X, Y and Z, which may be the same or different, are, for example, hydrogen, halogen, nitro, nitrile, or other defined groups and wherein R.sup.1 and R.sup.2 are alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted aralkyl, cycloalkyl groups, or optionally substituted heteroaromatic, and V is oxygen or sulfur.
    Type: Grant
    Filed: November 24, 1989
    Date of Patent: February 25, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Paul deFraine, Brian K. Snell, Kevin Beautement, Vivienne M. Anthony, John M. Clough
  • Patent number: 5081245
    Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: January 14, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
  • Patent number: 5061804
    Abstract: 3-thio pyrrolidines are intermediates for carbapenams.
    Type: Grant
    Filed: March 6, 1990
    Date of Patent: October 29, 1991
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masayoshi Murata, Hideo Tsutsumi, Keiji Matsuda, Hohji Hattori, Takashi Nakajima
  • Patent number: 5037822
    Abstract: The invention relates to the products of formula ##STR1## in which R represents the radical ##STR2## in which R.sub.1 at any position on the benzene ring represents a linear, branched or cyclic alkyl, alkenyl or alkynyl containing up to 8 carbon atoms, or the radical ##STR3## in which R.sub.2 and R.sub.3, which may be identical or different, represent a hydrogen atom or a linear alkyl, alkenyl or alkynyl containing up to 8 carbon atoms or form, together with the nitrogen atom to which they are attached, a carbonaceous heterocyclic radical optionally containing another hetero form, or the radical OR', R' representing hydrogen, a linear, branched or cyclic alkyl radical containing up to 8 carbon atoms or an aryl radical containing up to 14 carbon atoms, or the radical SR.sub.4 or S(O)R.sub.5, R.sub.4 and R.sub.5 representing a linear, branched or cyclic alkyl, alkenyl or alkynyl containing up to 8 carbon atoms, or R represents naphthyl optionally substituted with a radical R'.sub.1, R'.sub.
    Type: Grant
    Filed: February 21, 1990
    Date of Patent: August 6, 1991
    Assignee: Roussel-Uclaf
    Inventors: Emilio Toja, Fernando Barzaghi, Giulio Galliani
  • Patent number: 5034143
    Abstract: The present invention deals with the certain novel lactam based lubricating components which are guerbet alcohol derived ether containing lactam compounds. These materials are useful as lubricating oils where outstanding liquidity, resistance to oxidation, and minimal variation in viscosity as a function of temperature is required. This combination of properties make these compounds excellent candidates as additives to synthetic lubricating oil and extreme pressure additives.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: July 23, 1991
    Assignee: LCE Partnership
    Inventor: Anthony J. O'Lenick, Jr.
  • Patent number: 5021568
    Abstract: The present invention relates to organic chemistry. Lactam-1-acetic acid carbalkoxymethyl esters have the following general formula: ##STR1## wherein with R=H, n=1 or 3; with R=phenyl, n=1; R.sup.1 is an alkyl. A method for preparing said compounds comprises reacting lactams of the general formula: ##STR2## wherein with R=H, n=1 or 3, with R=phenyl n=1, with an alkali in a medium of aprotic solvents at a temperature of from 70.degree. to 130.degree. C., followed by the addition of an alkyl ester of a monohalcacetic acid to the resulting mixture and isolation of the desired product.The compounds according to the present invention are intermediate products in the synthesis of known biologically active substances.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: June 4, 1991
    Inventors: Alexandr G. Shipov, Evgenia P. Kramarova, Natalia A. Orlova, Jury I. Baukov, Kristap M. Ziemelis
  • Patent number: 5006157
    Abstract: A cyclic amide compound of the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom, a lower alkyl group, a haloalkyl group, a lower alkoxy group, a haloalkoxy group, a lower alkylthio group or a nitro group; Y is a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a phenyl group, an alkoxy group, a cycloalkoxy group, a cycloalkylalkoxy group, an alkenyloxy group, an alkynyloxy group, a benzyloxy group, a phenoxy group, a haloalkoxy group, a lower alkoxy-lower alkoxy group, a cyanoalkoxy group, an alkylthio group, an alkenylthio group, an alkynylthio group, a benzylthio group, a phenylthio group, ##STR2## (wherein W is an oxygen atom or a sulfur atom, R.sup.3 is a hydrogen atom or an alkyl group and R.sup.4 is an alkyl group), ##STR3## (wherein each of R.sup.5 and R.sup.6 is a hydrogen atom or a lower alkyl group, an alkylsulfonyl group, ##STR4## (wherein R.sup.5 and R.sup.
    Type: Grant
    Filed: November 28, 1989
    Date of Patent: April 9, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuyuki Ohba, Atsuhiko Ikeda, Kenji Matsunari, Yuji Yamada, Michiya Hirata, Yasuo Nakamura, Akira Takeuchi, Hiroyuki Karino
  • Patent number: 4997955
    Abstract: 1,1-disubstituted ethylene compounds of the general formula I ##STR1## where Z is COOR.sup.2, CN or COR.sup.3, R.sup.1 is an aliphatic, cycloalophatic, araliphatic, aromatic or heterocyclic radical which may be further substituted by functional groups which are inert under the reaction conditions, R.sup.2 is an aliphatic, cycloaliphatic or araliphatic radical of 1 to 15 carbon atoms and R.sup.3 is an aliphatic, cycloaliphatic or araliphatic radical of 1 to 15 carbon atoms which may be substituted by groups which are inert under the reaction conditions, and R.sup.1 together with R.sup.2 or R.sup.1 together with R.sup.3 may furthermore form an alkylene chain of 2 to 10 carbon atoms which may be substituted by groups which are inert under the reaction conditions, are prepared from a formyl compound of the general formula II ##STR2## where Z, R.sup.1, R.sup.2 and R.sup.3 have the above meanings, by a process in which the reaction is carried out in the presence of formaldehyde or paraformaldehyde and(a) a C.sub.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: March 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Joerg Liebe, Werner Bertleff
  • Patent number: 4988817
    Abstract: A process is provided for obtaining quaternary ammonium or phosphonium substituted carbonic acid esters. The first step involves reacting the hydroxyl predecessor compound of the ester with phosgene in an aprotic organic solvent to obtain a solution of chloroformate/hydrogen chloride complex. In a second step, the chloroformate/hydrogen chloride complex in solution is admixed with a salt whose conjugate anion, normally a phenol sulfonate, has structure L. During the admixing step, pH is maintained no lower than 6 until all reactants have been combined to form the product ester. Thereupon, pH is lowered to less than 5.5 to stabilize product against hydrolysis.
    Type: Grant
    Filed: November 16, 1988
    Date of Patent: January 29, 1991
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Stephen A. Madison, Jeffrey Bonn, Eddie N. Gutierrez
  • Patent number: 4985561
    Abstract: A process is described for obtaining sulfophenyl quaternary ammonium or phosphonium substituted carbonic acid esters. These esters are prepared through sulfonation with sulfur trioxide of aromatic chloroformates followed by reaction of the sulfonated aromatic chloroformate with quaternary ammonium or phosphonium substituted alcohols. The resultant sulfophenyl esters are useful as bleach precursors in combination with peroxygen compounds such as sodium perborate or percarbonate.
    Type: Grant
    Filed: August 29, 1989
    Date of Patent: January 15, 1991
    Assignee: Lever Brothers Company, Division of Conopco, Inc.
    Inventors: Stephen A. Madison, Leonora M. Ilardi, Hans Cerfontain
  • Patent number: 4956006
    Abstract: Substituted 1-phenyl pyrrolidones of the formula ##STR1## in which R.sup.1 is halogen, trifluoromethyl, cyano, CH.sub.3, CF.sub.2 CHF.sub.2, OCF.sub.2 CHF.sub.2, OCHF.sub.2, OCF.sub.3, SCH.sub.3, S(O)CH.sub.3, SO.sub.2 CH.sub.3, methoxyiminomethyl, methoxyimino-1-ethyl, benzoyloxyiminomethyl, benzoyloxyimino-1-ethyl, pyridyloxy, or pyridyloxy substituted with halogen and/or trifluoromethyl; R.sup.2 halogen, cyano, carboxy, carbalkoxy or carbalkoxy substituted with halogen, trifluoromethyl or phenyl; R.sup.3 is C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.4 alkenyl; X is H or halogen; Y is H or halogen; Z is O or S; and m and n are zero or 1; are useful as herbicidal agents.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: September 11, 1990
    Assignee: ICI Americas Inc.
    Inventor: Frank X. Woolard
  • Patent number: 4946845
    Abstract: Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: ##STR1## wherein: R.sup.1 and R.sup.2 are the same and are lower alkoxy or optionally substituted phenoxy,R.sup.3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2 or R.sup.3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(O).sub.n R wherein R is lower alkyl; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or optionally substituted heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2;at least one of X or Y is C(O)W and the other X or Y is different and is hydrogen, C(O)W or R.sup.
    Type: Grant
    Filed: November 25, 1988
    Date of Patent: August 7, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: D. V. Krishna Murthy, Michael C. Venuti, John M. Young
  • Patent number: 4946967
    Abstract: The invention relates to 5-oxo-3-pyrrolidinecarboxylic acid derivatives having the structural formula ##STR1## wherein X is selected from the group of ##STR2## R.sub.2 and R.sub.3 are each H or CH.sub.3, and R.sub.1 is H or a hydrocarbon radical having from 1 to 20 carbon atoms, which derivative compounds are suitable as monomers which can be homopolymerized or copolymerized to yield high molecular weight materials having many useful properties and applications, among which is their ability to form complexes with water insoluble molecules which are normally not complexible with similar type polymers.
    Type: Grant
    Filed: November 3, 1988
    Date of Patent: August 7, 1990
    Assignee: GAF Chemicals Corporation
    Inventors: Robert B. Login, John J. Merianos, Gary Dandreaux, Jenn S. Shih
  • Patent number: 4943584
    Abstract: Novel (p-phenoxyphenoxy)-methyl-five-membered heeroaromatic radicals of the formula ##STR1## where the substituents have the following meanings: R.sup.1, R.sup.2, R.sup.3 hydrogen, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.10 -cycloalkyl, nitro or cyano,R.sup.4 hydrogen or C.sub.1 -C.sub.4 -alkyl, and a five-membered heteroaromatic ring, and their use for combating pests.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: July 24, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Theobald, Christoph Kuenast, Peter Hofmeister, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Wolfgang Krieg, Joachim Leyendecker, Uwe Kardorff
  • Patent number: 4943640
    Abstract: The invention is a process for the preparation of a 5-(1-alkylcarbonyloxy)alkylpyrrolidin-2-one which comprises contacting a N-alkylcarbonyl-5-alkylcarbonylpyrrolidin-2-one with hydrogen in the presence of a catalytic amount of a hydrogenation catalyst under conditions such that a 5-(1-alkylcarbonyloxy)alkylpyrrolidin-2-one is prepared.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: July 24, 1990
    Assignee: The Dow Chemical Company
    Inventors: Edmund P. Woo, Michael J. Mullins
  • Patent number: 4931563
    Abstract: A process is provided for obtaining sulfophenyl quarternary ammonium or phosphonium substituted carbonic acid esters. The important step in this process involves reacting a phenyl quaternary ammonium or phosphonium substituted carbonic ester with oleum that contains from 0.5 to 33% sulfur trioxide. Amounts in excess of 33% sulfur trioxide lead to increased reaction times and, eventually, unacceptable product conversons.
    Type: Grant
    Filed: November 16, 1988
    Date of Patent: June 5, 1990
    Assignee: Lever Brothers Company
    Inventors: Stephen A. Madison, Leonora M. Ilardi
  • Patent number: 4904679
    Abstract: Pyrrolophenylalkanolamines of the formula ##STR1## R.sup.1 and R.sup.2 represent hydrogen or various radicals, R.sup.3 represents hydrogen, acyl or trialkylsilyl,R.sup.4 represents hydrogen or alkyl,R.sup.5 represents hydrogen, or, together with R.sup.3, represents ##STR2## wherein R.sup.7 represents hydrogen or alkyl, andR.sup.6 represents branched or cyfclic alkyl, which is optionally substituted,and salts thereof promote the yield of animals. Many new intermediates are also shown.
    Type: Grant
    Filed: April 22, 1988
    Date of Patent: February 27, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmund Wollweber, Jurgen Stoltefuss, Friedrich Berschauer, Ann de Jong, Martin Scheer