Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Five Membered Hetero Ring (e.g., Pyrrole Carbonyl Halides, Pyrrole Carboxaldehyde, Etc.) Patents (Class 548/530)
  • Patent number: 4827004
    Abstract: Novel Isoprene Derivatives which have mucosa-protective and gastric acid secretion-inhibiting properties and are useful for combatting ulcers both by treating and as a prophylaxis against gastric and/or duodenal ulcers.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: May 2, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
  • Patent number: 4824956
    Abstract: Aliphatic, cycloaliphatic, aromatic or araliphatic halogen compounds are reductively dehalogenated by reaction with hydrocarbons in the presence of carbon in the liquid phase at from 100.degree. to 450.degree. C. with formation of hydrogen halides.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: April 25, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Toni Dockner, Herbert Krug, Heinz Nohe
  • Patent number: 4820818
    Abstract: The muscle relaxant (E)-3-(9-chloro-5,6-dihydro-11H-pyrrolo[2,1-b][3]benzazepin-11-ylidene-N,N -dimethyl-1-propanamine is prepared by the geometric stereoselective dehydration of the intermediate carbinol with acidic agents and organic bases and low temperatures.
    Type: Grant
    Filed: May 2, 1988
    Date of Patent: April 11, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Ruth V. Wattley, Gerard R. Kieczykowski
  • Patent number: 4812580
    Abstract: The invention relates to a process for the preparation of 4-phenylpyrrole derivatives of the formula I ##STR1## wherein R.sub.n, R.sub.1 and R.sub.2 are as defined in claim 1, which comprises reacting a phenacylamine of formula II ##STR2## with a compound of formula IIIT--CH.dbd.CH--R.sub.1 (III)to give an intermediate of formula IV ##STR3## and cyclizing said intermediate, in the presence of a base, to give the compound I. Important intermediates and novel final products are also described.
    Type: Grant
    Filed: September 4, 1987
    Date of Patent: March 14, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Pierre Martin
  • Patent number: 4810819
    Abstract: A new enantioselective process is described for preparing optically active alpha-arylalkanoic acids by:(a) halogenation on the aliphatic carbon atom alpha to the ketal group, of ketals of formula ##STR1## in which Ar represents an aryl, optionally substituted;R represents a C.sub.1 -C.sub.4 alkyl;R.sub.1 and R.sub.2, represents a hydroxy, a O.sup.- M.sup.+, OR.sub.3 or NR.sub.4 R.sub.5 group;the carbon atoms indicated by an asterisk both simultaneously are in (R) or (S) configuration.This reaction is diastereoselective, so that a mixture of alpha-haloketals is obtained in which one of the two epimers prevails, and generally strongly prevails, over the other.(b) rearrangement of the haloketals of formula ##STR2## in which X is Cl, Br or I to alpha-arylalkanoic acids in a single stage or in two successive stages, by way of esters of formula ##STR3## The compounds (A) and (C) are all new compounds. The rearrangement step (b) may be performed under new, inventive conditions.
    Type: Grant
    Filed: August 5, 1987
    Date of Patent: March 7, 1989
    Assignee: Zambon Spa
    Inventors: Claudio Giordano, Graziano Castaldi, Fulvio Uggeri, Silvia Cavicchioli
  • Patent number: 4801735
    Abstract: Compounds are described of the following formula ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, C.sub.1-12 alkyl or C.sub.2-12 alkenyl, at least one of R.sup.1 and R.sup.2 being C.sub.1-12 alkyl or C.sub.2-12 alkenyl; X.sup.1 and X.sup.2 are each hydrogen or a protecting group; and Y is(a) --(CH.dbd.CH).sub.n Z in which n is 1, 2 or 3 and Z is --CHO, --CH.sub.2 OH, --COR.sup.3, --(CH.sub.2).sub.m --COR.sup.3 or --(CH.sub.2).sub.p CH.dbd.CH(CH.sub.2).sub.q --COR.sup.3 in which m is an integer of 1 to 12, p is an integer of 1 to 4, q is an integer of 1 to 10 and R.sup.3 is (i) --OH or (ii) --NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are each hydrogen, C.sub.1-4 alkyl or optionally substituted phenyl, or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a morpholino, pyrrolidinyl or piperidino ring,(b) --CH.dbd.NR.sup.6 in which R.sup.6 is (i) --OH, (ii) C.sub.1-12 alkyl optionally substituted by --OH, --COOH or --NR.sup.7 R.sup.8 where R.sup.7 and R.sup.
    Type: Grant
    Filed: November 25, 1985
    Date of Patent: January 31, 1989
    Assignee: Lilly Industries Limited
    Inventors: Mark A. W. Finch, John R. Harris
  • Patent number: 4798901
    Abstract: Novel pyrrole derivatives of the formula ##STR1## wherein one of R.sub.2 and R.sub.3 is ##STR2## and the other of R.sub.2 and R.sub.3 as well as R.sub.4 and R.sub.5 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 18 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms, --CN, --CF.sub.3, --NO.sub.2, --COOAlk and Alk is alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, ##STR3## n is 0, 1 or 2, R', R.sub.1 ' and R.sub.2 ' are alkyl of 1 to 8 carbon atoms and R.sub.4 and R.sub.5 taken together with the carbon atoms to which they are attached may form an optionally further unsaturated carbon homocycle of up to 8 carbon atoms, Z is selected from the group consisting of hydrogen, --CN, --C.tbd.CH, --CF.sub.3 and alkyl of 1 to 3 carbon atoms, A is the residue of a pyrethrinoid acid, R.sub.
    Type: Grant
    Filed: December 2, 1987
    Date of Patent: January 17, 1989
    Assignee: Roussel Uclaf
    Inventors: Jean Tessier, Jean-Pierre Demoute, Laurent Taliani
  • Patent number: 4792568
    Abstract: This invention relates to new lipoxygenase inhibitors possessing anti-inflammatory and anti-allergic properties. The present new compounds are of the formula: ##STR1## and salts thereof; wherein, R is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, lower aralkyl, phenyl, naphthyl, or a nitrogen oxygen or sulfur heterocyclic; andY.sub.1 and Y are independently hydrogen, lower alkyl, hydroxy, lower alkoxy, aryloxy, lower aralkoxy, aryl, lower aralkyl, carboxy, lower carbalkoxy, lower carbaralkoxy, carbaryloxy, formyl, or alkyl, alkenyl or alkynyl containing up to 6 carbon atoms in the principal chain and up to a total of 10 carbon atoms;provided that when Y and Y.sub.1 are both hydrogen or when Y.sub.1 is hydrogen and Y is CHO, the R is other than hydrogen, unsubstituted phenyl, or lower alkyl.
    Type: Grant
    Filed: April 14, 1986
    Date of Patent: December 20, 1988
    Assignee: Rorer Pharmaceutical Corporation
    Inventor: Joseph Auerbach
  • Patent number: 4792555
    Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sup.1 is lower alkyl, lower alkoxycarbonyl lower alkyl, aralkoxycarbonyl, aralkoxycarbonyl lower alkyl or indol-2-yllower alkyl;R.sup.2 is hydrogen, lower alkyl or biphenylyl lower alkylcarbonyl; orR.sup.1 and R.sup.2 taken together form a 5- or 6-membered saturated heterocyclic ring;R.sup.3 is hydrogen or lower alkyl;R.sup.4 is alkyl of 10-20 carbon atoms, cycloalkyl of 10-20 carbon atoms or phenylalkyl of 10-16 carbon atoms; orR.sup.3 and R.sup.4 taken are decahydroisoquinolin-2-yl, 3,5-dimethylpiperazin-1-yl or 3,3,5-trimethylhexahydroazepin-1-yl;or a pharmaceutically acceptable salt thereof, and their use in the prevention and/or treatment of conditions such as allergic rhinitis, allergic bronchial asthma and other naso-bronchial obstructive air-passageway conditions, other immediate hypersensitivity reactions such as allergic conjunctivities and various inflammatory conditions.
    Type: Grant
    Filed: March 20, 1987
    Date of Patent: December 20, 1988
    Assignee: American Home Products Corporation
    Inventors: William H. McGregor, Joseph Y. Chang
  • Patent number: 4791133
    Abstract: This invention relates to leukotriene B.sub.4 antagonists having the structure ##STR1## and the pharmaceutically acceptable addition salts thereof; wherein R.sup.1 is lower alkyl having 1-10 carbon atoms; or lower alkenyl or alkynyl having 2-10 carbon atoms; or lower alkadienyl having 3-10 carbon atoms; or lower alkadiynyl or alkenynyl having 4-10 carbon atoms;wherein R.sup.2 and R.sup.3 are the same or different and represent hydrogen or lower alkyl having 1-6 carbon atoms;wherein X is CH.dbd.CH, S, or O;wherein Y is CH.dbd.CH or C.tbd.C;wherein Z is OR.sup.4 or NR.sup.5 R.sup.6, and wherein R.sup.4 represent H, lower alkyl having 1-6 carbon atoms, or a pharmaceutically acceptable cation, and wherein R.sup.5 and R.sup.6 act independently and represent H or lower alkyl having 1-6 carbon atoms, or R.sup.5 and R.sup.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: December 13, 1988
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • 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: 4781750
    Abstract: Enols, their geometric isomers, tautomers and halogen addition products having the formula ##STR1## as defined herein and compositions containing these compounds exhibit herbicidal activity.
    Type: Grant
    Filed: August 27, 1985
    Date of Patent: November 1, 1988
    Assignee: Rohm and Haas Company
    Inventor: John W. Ashmore
  • Patent number: 4767757
    Abstract: Novel fungicidally active acyloxythiophene-carboxamides of the formula ##STR1##
    Type: Grant
    Filed: March 19, 1987
    Date of Patent: August 30, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Daum, Gerd Hanssler
  • Patent number: 4751315
    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, clausenamide. 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: September 1, 1987
    Date of Patent: June 14, 1988
    Assignees: Bayer Aktiengesellschaft, Chinese Academy of Medical Sciences
    Inventor: Wolfgang Hartwig
  • Patent number: 4746350
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: Y is selected from phenyl, furyl, thienyl and pyrrolyl rings (each optionally substituted by group X), optionally branched alkylene or alkylenethio(oxy)alkylene;X which may be the same or different are independently selected from halogen, nitro, alkyl, substituted alkyl, hydroxy, alkoxy, carboxy, alkoxycarbonyl, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino and alkanoyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl and alkynyl;R.sup.3 is selected from alkyl; andR.sup.4 is selected from hydrogen, alkyl, and alkoxycarbonyl.
    Type: Grant
    Filed: April 14, 1986
    Date of Patent: May 24, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventor: Keith G. Watson
  • Patent number: 4740508
    Abstract: Compounds of the formula ##STR1## are disclosed. These compounds are useful as hypotensive agents due to their angiotensin converting enzyme inhibition activity and depending upon the definition of X may also be useful as analgesics due to their enkephalinase inhibition activity.
    Type: Grant
    Filed: April 22, 1985
    Date of Patent: April 26, 1988
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Harold N. Weller, III, Eric M. Gordon
  • Patent number: 4737513
    Abstract: Novel pyrrole derivatives of the formula ##STR1## wherein one of R.sub.2 and R.sub.3 is ##STR2## and the other of R.sub.2 and R.sub.3 as well as R.sub.4 and R.sub.5 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 18 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms, --CN, --CF.sub.3, --NO.sub.2, --COOAlk and Alk is alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, ##STR3## n is 0, 1 or 2, R', R.sub.1 ' and R.sub.2 ' are alkyl of 1 to 8 carbon atoms and R.sub.4 and R.sub.5 taken together with the carbon atoms to which they are attached may form an optionally further unsaturated carbon homocycle of up to 8 carbon atoms, Z is selected from the group consisting of hydrogen, --CN, --C.tbd.CH, --CF.sub.3 and alkyl of 1 to 3 carbon atoms, A is the residue of a pyrethrinoid acid, R.sub.
    Type: Grant
    Filed: August 13, 1985
    Date of Patent: April 12, 1988
    Assignee: Roussel Uclaf
    Inventors: Jean Tessier, Jean-Pierre Demoute, Laurent Taliani
  • 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: 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: 4709053
    Abstract: The invention relates to a process for the preparation of 4-phenylpyrrole derivatives of the formula I ##STR1## wherein R.sub.n, R.sub.1 and R.sub.2 are as defined in claim 1, which comprises reacting a phenacylamine of formula II ##STR2## with a compound of formula IIIT--CH.dbd.CH--R.sub.1 (III)to give an intermediate of formula IV ##STR3## and cyclizing said intermediate, in the presence of a base, to give the compound I.Important intermediates and novel final products are also described.
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: November 24, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Pierre Martin
  • Patent number: 4701465
    Abstract: The present invention relates to N-acylpyrrolidine derivatives of the general formula (I): ##STR1## wherein R.sup.1 is a hydrogen atom, a C.sub.1-4 alkyl group or the phenyl group, with the proviso that when R.sup.1 is a hydrogen atom, R.sup.2 is phenoxy group, benzoyl, the phenyl group, or a phenyl group which is mono-substituted by a halogen atom or a C.sub.1-4 alkoxy group, and that when R.sup.1 is a C.sub.1-4 alkyl group or the phenyl group, R.sup.2 is an aralkyl group of 7 to 10 carbon atoms, a C.sub.1-4 alkyl group, the phenyl group or a phenyl group mono-substituted by a halogen atom or a C.sub.1-4 alkoxy group; or R.sup.1 and R.sup.2 together form an unsubstituted benzylidene group or a benzylidene group which may be mono-substituted by a C.sub.1-4 alkoxy group; wherein n is an integer of 0 to 5; and pharmaceutical compositions thereof which are useful as anti-amnesic agents.
    Type: Grant
    Filed: April 16, 1986
    Date of Patent: October 20, 1987
    Assignee: Suntory Limited
    Inventors: Takaharu Tanaka, Masayuki Saitoh, Masaki Hashimoto, Naoki Higuchi
  • Patent number: 4691026
    Abstract: A compound represented by the following formula: ##STR1## wherein R is a C.sub.3 -C.sub.24 olefinically unsaturated organic radical having functionality which renders the nitrogen atom electron deficient, the olefinic unsaturation functionality being polymerizable,R.sup.1 is hydrogen or a C.sub.1 -C.sub.4 alkyl radical, orR and R.sup.1 together with the nitrogen atom can form an olefinically unsaturated 5 to 7-member ring which has functionality that renders the nitrogen atom electron deficient and the olefinic unsaturation functionality is polymerizable,R.sup.2 and R.sup.3 are hydrogen, a C.sub.1 -C.sub.4 alkyl or acyl radical, orR.sup.2 and R.sup.3 together are a C.sub.2 -C.sub.4 alkylene group,R.sup.4 is hydrogen or a C.sub.1 -C.sub.4 alkyl, acyl, ester, amide or acid group, andn is an integer from 1 to 10, provided n is not 1 when R is (meth)acryloyl, R.sup.2 and R.sup.3 are methyl and R.sup.1 and R.sup.4 are hydrogen.Under acidic conditions the above compounds having R.sup.
    Type: Grant
    Filed: July 30, 1985
    Date of Patent: September 1, 1987
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Robert K. Pinschmidt, Jr., Dale D. Dixon, William F. Burgoyne, Jr.
  • Patent number: 4686233
    Abstract: Pesticidal water-soluble aminoacid sulfenylated carbamates useful as broad spectrum insecticides and miticides, particularly useful as systemic insecticides.
    Type: Grant
    Filed: May 1, 1986
    Date of Patent: August 11, 1987
    Assignee: Union Carbide Corporation
    Inventors: Chennupati K. Rao, Themistocles D. D'Silva
  • Patent number: 4684660
    Abstract: Compounds having the formula ##STR1## and alkyl esters and salts thereof. R.sub.1 is hydrogen, alkanoyl or ##STR2## R.sub.2 is hydrogen, alkyl, or phenylalkyl; n is 0 or 1; andA.sub.1 and A.sub.2 each is an .alpha.-amino or .alpha.-imino acid residue joined through a peptide bond, have useful hypotensive activity.
    Type: Grant
    Filed: May 1, 1980
    Date of Patent: August 4, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Miquel A. Ondetti, Josip Pluscec
  • Patent number: 4684662
    Abstract: The invention relates to compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and represent alkyl or aryl or together form a C chain and R.sup.3 denotes alkyl or aryl, a process for their preparation and their use.
    Type: Grant
    Filed: January 5, 1984
    Date of Patent: August 4, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rainer Henning, Hansjorg Urbach
  • Patent number: 4677120
    Abstract: Esters and amides of 13-cis-retinoic acid are disclosed which are used for the treatment of acne and skin diseases.
    Type: Grant
    Filed: July 31, 1985
    Date of Patent: June 30, 1987
    Assignee: Molecular Design International
    Inventors: Harlie A. Parish, William P. Purcell
  • Patent number: 4652582
    Abstract: Antiinflammatory 2-halo-4,5-diarylpyrroles are provided. These pyrroles have the formula: ##STR1## wherein Y.sub.1 is F, Cl, Br, or I;Y.sub.2 is H, Cl, or Br;R.sub.1 is H, CH.sub.3, C.sub.2 H.sub.5, acetyl, or ##STR2## where R.sub.4 is methyl, ethyl, t-butyl, or benzyl; R.sub.2 is pyridyl or ##STR3## R.sub.3 is pyridyl or ##STR4## X and X' are independently H, F, Cl, Br, OR.sub.5, or R.sub.5 S(O).sub.n where n is 0, 1 or 2 and R.sub.5 is C.sub.1 -C.sub.2 alkyl; provided that one of R.sub.2 or R.sub.3 must be ##STR5## or a pharmaceutically suitable salt thereof. Intermediates to the above pyrroles are provided where R.sub.1 in the above formula is replaced by R.sup.1 which is benzenesulfonyl or 4-toluenesulfonyl.
    Type: Grant
    Filed: January 9, 1985
    Date of Patent: March 24, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Wendell W. Wilkerson
  • Patent number: 4626545
    Abstract: Compounds of the formula ##STR1## and their use as angiotensin converting enzyme inhibitors and antihypertensives are disclosed.
    Type: Grant
    Filed: August 27, 1984
    Date of Patent: December 2, 1986
    Assignee: Merck & Co., Inc.
    Inventor: David Taub
  • Patent number: 4608201
    Abstract: A process for preparing a lactam imide involves reacting together a lactam, a non-volatile carboxyl group-containing material, and an anhydride of a volatile carboxylic acid with the proviso that an appreciable amount of non-volatile carboxyl group-containing material and volatile carboxylic acid which is generated as the anhydride reacts are both present in the reaction mixture at the same time.
    Type: Grant
    Filed: May 21, 1984
    Date of Patent: August 26, 1986
    Assignee: PPG Industries, Inc.
    Inventor: Gregory J. McCollum
  • Patent number: 4594343
    Abstract: Novel 1-[(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl]-.alpha.,.alpha.-diaryl-pyrrolidine, piperidine and homopiperidineacetamides and acetonitriles having the formula: ##STR1## wherein; n is zero, one or two;X is oxygen or sulfur;Z is ##STR2## p is 0 to 5 inclusive with the proviso that when Z is ##STR3## p is at least one; Y is aminocarbonyl or cyano;Ar.sup.1 and Ar.sup.2 are 2, 3 or 4-pyrido, phenyl or substituted phenyl;R is hydrogen or loweralkyl;R.sup.1, R.sup.2 and R.sup.3 are hydrogen, cycloalkyl, loweralkyl, phenyl, substituted phenyl, phenylloweralkyl, and R.sup.2 and R.sup.3 taken with the adjacent nitrogen may form a heterocyclic residue, and diastereoisomers when possible and pharmaceutical salts; and the method and pharmaceutical compositions for treating cardiac arrhythmias therewith are disclosed.
    Type: Grant
    Filed: October 19, 1984
    Date of Patent: June 10, 1986
    Inventors: James R. Shanklin, Jr., James M. Wilkinson, II
  • Patent number: 4594429
    Abstract: The present invention relates to a novel process for producing 3-chloro-1-formyl-4-phenylpyrroles having the general formula [I] as a useful fungicidal agent in agriculture and horticulture which is manufactured from the starting material of 3-phenyl-2,2,4-trichlorobutanal having the general formula [IV] as set forth in the following reaction formulae:By means of obtaining a pyrroline derivative having the general formula [III] as the intermediate compound, its production operation is greatly simplified and its yield rate is raised in comparison with the conventional processes. ##STR1## where X denotes the same or different kinds of substituent(s) being chosen from the group consisting of halo, nitro, and trifluoromethyl and n denotes zero or an integer of 1 or 2.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: June 10, 1986
    Assignee: Nippon Soda Co. Ltd.
    Inventors: Akiyoshi Ueda, Fumihiko Nagasaki, Yutaka Takakura, Shigeru Kojima
  • Patent number: 4575489
    Abstract: Novel peptide B-52653 having the formula: ##STR1## which is produced by cultivating a microorganism belonging to the genus Streptomyces and being capable of producing B-52653 in a culture medium, whereby B-52653 is elaborated and accumulated in the cultured broth and is recovered.B-52653 is useful as a germicide or disinfectant, and a possibility of the present substance as an antifibrotic agent is suggested.
    Type: Grant
    Filed: September 8, 1981
    Date of Patent: March 11, 1986
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Eiji Higashide, Satoshi Horii
  • Patent number: 4569689
    Abstract: Aniline derivatives of the formula ##STR1## where R.sup.1 is alkoxy, alkylthio, unsubstituted or substituted cycloalkoxy or the radical --NR.sup.2 R.sup.3, X is --CH.sub.2 --, --CH(OH)-- or --CO--, A is an unsubstituted or substituted alkylene chain, B is unsubstituted or substituted methylene or dimethylene, Z is hydrogen, halogen, alkyl, alkoxy, haloalkyl or haloalkoxy, and n is 1, 2 or 3, are used for controlling undesirable plant growth.
    Type: Grant
    Filed: June 14, 1984
    Date of Patent: February 11, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Schirmer, Norbert Goetz, Bruno Wuerzer
  • Patent number: 4565877
    Abstract: A naphthalene derivative of the formula: ##STR1## wherein R.sup.1 is hydrogen and R.sup.2 is lower alkyl or phenyl-lower alkyl; or R.sup.1 and R.sup.2 are combined together to form lower alkylene; X is halogen; and the absolute configuration at the asymmetric carbon atom shown by the asterisk is either (S)- or (R)-configuration, and a method of preparation thereof are disclosed. Said naphthalene derivative is useful as a chiral reagent for determining the optical purity of an optically active compound containing within its molecule at least one functional group selected from hydroxy, amino and imino groups.
    Type: Grant
    Filed: October 11, 1983
    Date of Patent: January 21, 1986
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Hiroshi Wada, Kazuhiro Ishii, Nobuchika Tsumagari, Masaaki Matsuo, Mikio Matsumoto
  • Patent number: 4559357
    Abstract: Compounds of the formula ##STR1## and of the isomeric formulae ##STR2## wherein R is alkyl or halogen, R.sub.1 is hydrogen, optionally substituted alkyl or optionally substituted alkenyl, R.sub.2 is hydrogen or methyl, R.sub.3 is hydrogen, alkyl or alkenyl, and X is oxygen or sulfur, including their acid salts, are insecticidally and acaricidally active.
    Type: Grant
    Filed: June 6, 1983
    Date of Patent: December 17, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean-Claude Gehret, Walter Traber
  • Patent number: 4558127
    Abstract: 5-Fluorouracil nitroxyl derivatives of the general formula: ##STR1## wherein R.sub.1 =R.sub.2 =X, ##STR2## or R.sub.1 =X, R.sub.2 =H, or R.sub.1 =H, R.sub.2 =X,or R.sub.1 =Na, R.sub.2 =X,possessing an antitumor activity.
    Type: Grant
    Filed: October 17, 1984
    Date of Patent: December 10, 1985
    Inventors: Nikolai M. Emanuel, Albina N. Rozenberg, Valery A. Golubev, Gennady N. Bogdanov, Ljubov S. Vasilieva, Nina P. Konovalova
  • Patent number: 4550205
    Abstract: The invention relates to new diphenyl ethers of the general formula ##STR1## wherein X is a hydrogen atom, a halogen atom, a nitro group, an optionally halogenated alkyl, alkoxy or alkylthio group having 1-6 carbon atoms, or an alkanoyl group having 1-4 carbon atoms;Y is a nitrogen atom or a group of the formula CH or CCl;Z is a hydrogen atom, a halogen atom, a nitro group, an optionally halogenated alkyl group having 1-4 carbon atoms, or an alkanoyl group having 1-4 carbon atoms; n is 0-2;R.sub.1 is a hydrogen atom, or an alkyl or alkanoyl group having 1-4 carbon atoms;R.sub.2 and R.sub.3 are equal or different and represent hydrogen atoms or alkyl groups having 1-4 carbon atoms; andA is a group of the general formula ##STR2## wherein R.sub.4 is a hydrogen atom, an alkyl group having 1-6 carbon atoms, or a cation of an alkali metal, alkaline earth metal or an alkylated or non-alkylated ammonium group, andR.sub.5 and R.sub.
    Type: Grant
    Filed: November 4, 1982
    Date of Patent: October 29, 1985
    Assignee: Duphar International Research B.V.
    Inventors: Gerard B. Paerels, Cornelis W. Raven
  • Patent number: 4511725
    Abstract: N-acyl-2,5-dimethylpyrroles and a process for their preparation. The process involves heating a mixture of acetonylacetone and an amide. The ensuing reaction is a condensation reaction with water being split out.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: April 16, 1985
    Assignee: Borg-Warner Chemicals, Inc.
    Inventors: Ingenuin Hechenbleikner, William P. Enlow
  • Patent number: 4507292
    Abstract: Aryl N-oxalyl-N-methyl-carbamates of the general formula ##STR1## in which X represents an alkoxy, alkenoxy, alkinoxy, aryloxy, alkylthio, alkenylthio, alkinylthio or arylthio radical, each of which may be optionally substituted, or represents a radical of the general formula --N R.sup.3 R.sup.4, wherein R.sup.3 and R.sup.4 are identical or different and represent a hydrogen atom or an alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl or aryl radical, each of which may be optionally substituted,or the radicals R.sup.3 and R.sup.4, together with the N atom to which they are bonded, form an optionally substituted heterocyclic ring, andR.sup.1 represents an aryl radical which is optionally substituted,are novel and find use as pesticides, especially for combating insects, acarids and nematodes.
    Type: Grant
    Filed: January 27, 1983
    Date of Patent: March 26, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Heywang, Engelbert Kuhle, Wolfgang Behrenz, Ingeborg Hammann, Bernhard Homeyer
  • Patent number: 4500542
    Abstract: The invention relates to novel dioxaheterocyclic compounds of the formula I ##STR1## in which R.sub.1 represents an unsubstituted or substituted aromatic or heteroaromatic radical or an unsubstituted or lower alkylated, mono- or bi-cyclic cycloaliphatic hydrocarbon radical or an .alpha.-branched aliphatic hydrocarbon radical, each of R.sub.2 and R.sub.3, independently of the other, represents hydrogen or lower alkyl, and each of R.sub.4 and R.sub.5, independently of the other, represents hydrogen, lower alkyl or halogen, and A represents the radical --O--R.sub.6, wherein R.sub.6 represents hydrogen or an unsubstituted or substituted aliphatic or araliphatic hydrocarbon radical or A represents the radical ##STR2## in which each of R.sub.7 and R.sub.8, independently of the other, represents hydrogen or lower alkyl, or R.sub.7 and R.sub.
    Type: Grant
    Filed: November 8, 1983
    Date of Patent: February 19, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Ernst Habicht, Paul Zbinden
  • Patent number: 4466980
    Abstract: A novel compound selected from the group consisting of 7-(or 6- or 4-)thiaprostaglandin E.sub.1 derivatives of the formula (I). ##STR1## wherein A represents --CH.sub.2 -- or ##STR2## in which n is 0, 1 or 2, provided that only one A cut of three is ##STR3## R.sup.1 -R.sup.7 and G are as defined in the specification, the 15-epimers of said thiaprostaglandin E.sub.1 derivatives, the enatiomers of said thiaprostaglandin E.sub.1 derivatives or their 15-epimers, and mixtures of these compounds.A 7-thiaprostaglandin E.sub.1 derivative and/or its optical isomer may be prepared by reacting a 2-organo-2-cyclopentenone (II) with an organic copper-lithium compound (III) to effect conjugation reaction. A 6-thiaprostaglandin E.sub.1 derivative and/or its optical isomer may be prepared by subjecting an .alpha.,.beta.-unsaturated ketone (IV) and a thiol (V) to the Michael addition reaction.
    Type: Grant
    Filed: October 30, 1981
    Date of Patent: August 21, 1984
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Takeshi Toru, Takeo Oba, Noriaki Okamura, Kenzo Watanabe, Kiyoshi Bannai, Atsuo Hazato, Seizi Kurozumi, Fukuyoshi Kamimoto, Akira Ohtsu
  • Patent number: 4459305
    Abstract: The present invention relates to a cyclopropanecarboxylic acid ester derivative of the general formula I: ##STR1## in which R.sub.1 stands for a hydrogen atom, a methyl group, a halogen atom or a halomethyl group, R.sub.1 ' stands for a halomethyl or haloethyl group, R.sub.2 and R.sub.2 ' are the same or different, each standing for methyl group, a halogen atom or a halomethyl group, provided that if R.sub.1 is a hydrogen atom, R.sub.1 ' is a halomethyl group, and R.sub.2 and R.sub.2 ' are each a methyl group, and R stands for a group of the formula II, III, IV, V or VI: ##STR2## in which R.sub.3 stands for a hydrogen atom or a methyl group, R.sub.4 stands for an allyl, propargyl, benzyl or 2,4-pentadienyl group, X stands for an oxygen or sulfur atom, or a --CH.dbd.CH-- group, R.sub.5 stands for a hydrogen atom, or a cyano, ethynyl, propynyl or trifluoromethyl group, R.sub.6 stands for a hydrogen or halogen atom or a methyl or trifluoromethyl group, n is an integer of 1 to 4, R.sub.
    Type: Grant
    Filed: December 4, 1981
    Date of Patent: July 10, 1984
    Assignee: Dainippon Sochugiku Kabushiki Kaisha
    Inventors: Yoshio Katsuda, Yoshihiro Minamite
  • Patent number: 4456565
    Abstract: Acyl cyanides of the general formula ##STR1## in which R represents alkyl or substituted alkyl of from 1 to 8 carbon atoms; cycloalkyl or substituted cycloalkyl with 3 to 12 carbon atoms; aryl or substituted aryl; or an optionally substituted 5-membered or 6-membered heterocyclic radical which can additionally also be fused with a benzene ring, are prepared by reacting the corresponding carboxylic acid anhydride in the liquid phase with anhydrous hydrocyanic acid, at a temperature of between 50.degree. to 250.degree. C.
    Type: Grant
    Filed: July 14, 1983
    Date of Patent: June 26, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Herbert Schwarz
  • Patent number: 4455264
    Abstract: Acyl cyanides of the formula ##STR1## in which R represents an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted cycloalkyl group having 3 to 12 carbon atoms or an optionally substituted aryl group, or an optionally substituted 5-membered or 6-membered heterocyclic radical which additionally can be fused to a benzene ring,are obtained in high yields by reacting carboxylic acid anhydrides of the formula R--CO--O--CO--R (II) with trimethylsilyl cyanide, (CH.sub.3).sub.3 Si--CN (III), if appropriate in the presence of a catalyst and, if appropriate, in the presence of a diluent, at a temperature between 50.degree. and 250.degree. C. The acyl cyanides can be used as intermediate products, for example, for the preparation of certain herbicidally active compounds of the triazinone series.
    Type: Grant
    Filed: October 22, 1982
    Date of Patent: June 19, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Eckart Kranz
  • Patent number: 4431834
    Abstract: This invention relates to certain bicyclic derivatives which are indane and tetralin compounds and which have herbicidal properties, to processes for their preparation, to herbicidal compositions containing them and to a method of using them as herbicides.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: February 14, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventor: David Cartwright
  • Patent number: 4393218
    Abstract: A process for preparing 2,2-dialkyl-4-methyl-5,5-dialkyl-3-formyl-.DELTA..sup.3 -pyrrolines by reacting the corresponding dialkyl substituted di-tert-propargylamines with water at a pH equal to or less than 3.0. Preferably, an inorganic mercury compound is used as a catalyst.
    Type: Grant
    Filed: December 7, 1981
    Date of Patent: July 12, 1983
    Assignee: Anic, S.p.A.
    Inventors: Silvestro Costanzi, Francesco Tessarolo, Maurizio Brunelli
  • Patent number: 4393225
    Abstract: AI-77 compounds, pharmaceutically acceptable salts thereof, and a process for the preparation thereof are described, said compounds having the formulae ##STR1## wherein: X is NR.sub.6 or O; Y is NHR.sub.5 or combine with Z to provide a link for bonding C and C; Z is H or combines with Y to provide a link for bonding C and C; R.sub.1, R.sub.3 and R.sub.5 are each H, R', --CH.sub.2 R, or --COR; R.sub.6 is H or R; R.sub.7 is H, R or CH.sub.2 R; R is a hydrocarbon group consisting of a saturated or unsaturated straight or branched aliphatic group of C.sub.1 to C.sub.17, an aromatic group of C.sub.6 to C.sub.10, a cage type group of C.sub.7 to C.sub.10, a monocyclic aliphatic group of C.sub.3 to C.sub.8, an aromatic-aliphatic group of C.sub.7 to C.sub.15, a heterocyclic hydrocarbon of C.sub.1 to C.sub.9, wherein the above hydrocarbons can be substituted with one or more groups selected from halogen, oxo, carboxyl, hydroxyl, a saturated or unsaturated straight or branched aliphatic group of C.sub.1 to C.sub.
    Type: Grant
    Filed: July 11, 1980
    Date of Patent: July 12, 1983
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hiroshi Hayashi, Yukiji Shimojima, Takashi Shirai, Torao Ishida, Mitsuru Shibukawa
  • Patent number: 4383112
    Abstract: Chiral Schiff bases according to the general formula: ##STR1## and transition metal complexes thereof, wherein C.sup.* is an asymmetric carbon atom, R.sup.1 and R.sup.2, which may be the same or different are alkyl, aralkyl, aryl or alkaryl, R.sup.3 is hydrogen, alkyl, aralkyl, aryl or alkaryl, R.sup.4 and R.sup.5, which may be the same or different, are hydrogen or lower alkyl or, where n is 1, may with the cyclic ring to which CR.sup.4 R.sup.
    Type: Grant
    Filed: July 8, 1980
    Date of Patent: May 10, 1983
    Assignee: Imperial Chemical Industries Limited
    Inventors: Dale A. Laidler, David J. Milner
  • Patent number: 4379928
    Abstract: Alkyl amides have been synthesized from cyclic anhydrides, carboxyl acids and their esters by contacting them with an amine carbamic acid salt.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: April 12, 1983
    Assignee: Union Carbide Corporation
    Inventor: Spyros Theodoropulos
  • Patent number: 4349690
    Abstract: The present invention provides novel 9-deoxy-9-methylene-6-keto-PGE derivatives which are useful for platelet aggregation inhibition and gastric cyctoprotection.
    Type: Grant
    Filed: April 23, 1981
    Date of Patent: September 14, 1982
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy