Carbonyl Containing (e.g., Ketone Containing, Etc.) Patents (Class 568/31)
  • Patent number: 5283349
    Abstract: A 2,6,7-trisubstituted-3-methylenebicyclo-[3.3.0]octane of formula (I) or an enantiomer thereof, or a mixture of these in an arbitrary ratio. The compound is a key intermediate for preparation of isocarbacyclins which are useful as medicines for the circulatory system such as an antithrombotic agent, an antilipidemic agent, a hypotensive agent or an antiarterosclerotic agent.
    Type: Grant
    Filed: September 11, 1986
    Date of Patent: February 1, 1994
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Kiyoshi Bannai, Seizi Kurozumi
  • Patent number: 5274172
    Abstract: There is disclosed a process for preparing granular esters in one step by the reaction of an alcohol with acid chloride in an aqueous alkaline medium with moderate shear agitation and optionally in the presence of a surfactant.
    Type: Grant
    Filed: June 24, 1992
    Date of Patent: December 28, 1993
    Assignee: Monsanto Company
    Inventors: Yueting Chou, David A. Martin
  • Patent number: 5272178
    Abstract: The present invention relates to compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and independently represent tert-alkyl, phenyl, or hydrogen; R.sup.3 represents hydrogen or alkyl; X represents O, S or (CH.sub.2).sub.m wherein m is 1 or 2; A represents O or S(O).sub.n wherein n is 0, 1, or 2; p is an integer from 0 to 4; and R represents alkyl; OH; OR.sup.4 wherein R.sup.4 is alkyl; or NR.sup.5 R.sup.6 wherein R.sup.5 is hydrogen or alkyl, and R.sup.6 is hydrogen, alkyl, heterocyclealkyl, substituted heterocyclealkyl, cycloalkyl, substituted cycloalkyl, phenyl, substituted phenyl, phenylalkyl, or substituted phenylalkyl, or NR.sup.5 R.sup.6 together form a heterocyclic ring which may optionally be substituted; or (CH.sub.2).sub.t COOR.sup.7 wherein t is an integer from 1 to 4 and R.sup.7 is hydrogen or alkyl; and the pharmaceutically acceptable salts thereof. The compounds are inhibitors or stimulators of superoxide generation.
    Type: Grant
    Filed: April 8, 1993
    Date of Patent: December 21, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 5260489
    Abstract: A process for purifying a halogenated aromatic sulfone or ketone compound comprises contacting the compound with a mixture containing a solvent having a normal boiling point less than about 225.degree. C. and water to form a second mixture, heating the second mixture at a temperature sufficient to substantially dissolve the halogenated compound to form a third mixture, cooling the third mixture to purify and recrystallize the compound, and recovering the purified, recrystallized compound. A second embodiment of the invention comprises repeating the purification process steps at least once to further purify the halogenated aromatic sulfone or ketone compound.
    Type: Grant
    Filed: September 30, 1992
    Date of Patent: November 9, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Rex L. Robsein, Jimmie J. Straw, Darryl R. Fahey
  • Patent number: 5237102
    Abstract: Provided is a novel process for readily producing .beta.-carotene in which a sulfone compound represented by the general formula (1), (2) or (3) is reacted with an alkali, ##STR1## wherein R represents a phenyl group which may be substituted, R' a protecting group of acetal type and X a halogen atom.
    Type: Grant
    Filed: August 31, 1992
    Date of Patent: August 17, 1993
    Assignee: Kuraray Company Ltd.
    Inventors: Toshiki Mori, Hiroshi Fujii, Takashi Onishi, Kazuo Yamamoto
  • Patent number: 5210258
    Abstract: Optically active naphthyl alpha-substituted alkyl ketones, are a class of ketones useful as intermediates in the production of optically active alpha-naphthylalkanoic acids which exhibit anti-inflammatory, analgesic and anti-pyretic activity.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: May 11, 1993
    Assignee: Syntex Pharmaceuticals International Ltd.
    Inventor: George C. Schloemer
  • Patent number: 5206440
    Abstract: A process for production of fluorinated sulfones from fluorinated organic sulfides by oxidation of the sulfides with an oxidizing reagent made from fluorine, water and acetonitrile. The sulfones are useful as second order nonlinear optical dyes.
    Type: Grant
    Filed: July 28, 1992
    Date of Patent: April 27, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Richard Beckerbauer, Shlomo Rozen
  • Patent number: 5200535
    Abstract: The invention provides cyclohexanone derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5; each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group; R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrogen atom or an alkyl group; R.sup.6 and R.sup.7 together represent a single carbon-carbon bond or an epoxy group; and R.sup.8 represents a hydrogen atom or a hydroxyl group; with the proviso that when R.sup.6 and R.sup.7 together represent an epoxy group then R.sup.8 represents a hydrogen atom; and a process for their preparation. Compounds of formula I are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: April 6, 1993
    Assignee: Shell Research Limited
    Inventor: Paul H. Briner
  • Patent number: 5185468
    Abstract: Provided is a novel process for readily producing .beta.-carotene by reacting a sulfone compound represented by the general formula (1), (2) or (3) with an alkali, ##STR1## wherein R represents a phenyl group which may be substituted, R' a protecting group of acetal type and X a halogen atom.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: February 9, 1993
    Assignee: Kuraray Company Ltd.
    Inventors: Toshiki Mori, Hiroshi Fujii, Takashi Onishi, Kazuo Yamamoto
  • Patent number: 5169988
    Abstract: The invention relates to novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof with herbicidal and plant growth regulating properties.The novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof are of the formula I ##STR1## wherein A is a 2- to 7-membered alkylene bridge, or a 3- to 7-membered alkenylene bridge which may be mono- or polyunsaturated,n is 0, 1 or 2,R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; or is C.sub.3 -C.sub.6 cycloalkyl; or phenyl, benzyl or phenylethyl, the phenyl ring of each of which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, cyano or nitro,X is oxygen or a radical --NOR.sub.3, andR.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.
    Type: Grant
    Filed: April 8, 1992
    Date of Patent: December 8, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans Tobler
  • Patent number: 5166441
    Abstract: The present invention related to novel compounds useful in the manufacture of astaxanthin and to processes for their preparation. The novel intermediates have the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are C.sub.1-6 -alkyl which may be branched or phenyl, and ##STR2## wherein R' is alkyl, alkoxy, NO.sub.2, NH.sub.2 or halogen.
    Type: Grant
    Filed: December 9, 1991
    Date of Patent: November 24, 1992
    Assignee: NeuroSearch A/S
    Inventor: Peter Moldt
  • Patent number: 5157150
    Abstract: A process for the preparation of 2-(chloro, bromo or nitro)-4-(alkylsulfonyl)benzoic acid and to intermediates used in the process.
    Type: Grant
    Filed: January 15, 1991
    Date of Patent: October 20, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Richard W. Brown
  • Patent number: 5152826
    Abstract: An herbicide compound of 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; orR.sup.1 and R.sup.2 together are alkylene having 2 to 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; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 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.n --wherein n 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.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: October 6, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Christopher G. Knudsen
  • Patent number: 5132462
    Abstract: The invention relates to novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof with herbicidal and plant growth regulating properties.The novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof are of the formula I ##STR1## wherein A is a 2- to 7-membered alkylene bridge, or a 3- to 7-membered alkenylene bridge which may be mono- or polyunsaturated,n is 0, 1 or 2,R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; or is C.sub.3 -C.sub.6 cycloalkyl; or phenyl, benzyl or phenylethyl, the phenyl ring of each of which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, cyano or nitro,X is oxygen or a radical --NOR.sub.3, andR.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: July 21, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans Tobler
  • Patent number: 5131945
    Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: July 21, 1992
    Assignee: Shell Research Limited
    Inventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
  • Patent number: 5128479
    Abstract: Oxidized diphenylheteroalkanes of the formula I ##STR1## where R.sup.1 to R.sup.6 and A have the meanings specified in the description, and the preparation thereof are described. The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: July 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5116869
    Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: May 26, 1992
    Assignee: Teijin Limited
    Inventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
  • Patent number: 5110343
    Abstract: The invention relates to a herbicidal composition having an inert carrier and an effective amount of a compound having the formula ##STR1## wherein X is the same or different substituent selected from the group consisting of halogen, nitro, C.sub.1-6 alkyl, halo C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio and C.sub.1-6 alkylsulfonyl;n is 1, 2, 3 or 4;R.sup.1 is C.sub.1-6 alkyl which is substituted by cyano, halogen, hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulfonyl or tetrahydropyranyloxy; C.sub.1-6 alkylthio, phenylthio, pyridyl or tetrahydropyranyl;R.sup.2 is C.sub.1-6 alkyl;l is 0, 1 or 2.
    Type: Grant
    Filed: May 24, 1990
    Date of Patent: May 5, 1992
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Akiyoshi Ueda, Haruhito Ohishi, Toshio Aihara, Hisao Ishikawa, Kazuyuki Tomida, Hideo Hosaka
  • Patent number: 5107029
    Abstract: This invention concerns a process for preparing diketones and keto-acids by reacting a dicarboxylic acid and an aromatic compound in the presence of an alkylsulfonic acid such as methanesulfonic acid and an organic anhydride compound such as methanesulfonic anhydride or trifluoroacetic anhydride. The diketones and keto-acids can be used to prepare polyketones which are useful as molding plastics, coatings, films, fibers, and the like.
    Type: Grant
    Filed: July 23, 1990
    Date of Patent: April 21, 1992
    Assignee: Eastman Kodak Company
    Inventors: Theodore R. Walker, Jr., Winston J. Jackson, Jr., Jean C. Fleischer
  • Patent number: 5106407
    Abstract: The present invention discloses the antimicrobial utility of certain iodonium ylide compounds. The particular iodonium ylide compounds are phenyl iodonium ylides having an ortho substituent that stabilizes the positive charge on the polyvalent iodine by a nonbonded electrostatic interaction. The polyvalent iodine is further stabilized by a cyclic 1,3-dicarbonyl anion.
    Type: Grant
    Filed: December 4, 1989
    Date of Patent: April 21, 1992
    Assignee: The Dow Chemical Company
    Inventors: Attila G. Relenyi, Gerald F. Koser, Richard W. Walter, Jr., William J. Kruper, Jr., Ravi B. Shankar, Anthony P. Zelinko
  • Patent number: 5100460
    Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.
    Type: Grant
    Filed: July 13, 1989
    Date of Patent: March 31, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Philippe Desbordes, Michel Euvrard
  • Patent number: 5101065
    Abstract: A process for the preparation of 2-(hydrogen, halogen or lower alkyl)-3-(hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, --OCH.sub.2 CH.sub.2 OCH.sub.3, --OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, --OCH.sub.2 CH.sub.2 SCH.sub.3 or --OCH.sub.2 CH.sub.2 SC.sub.2 H.sub.5)-4-(alkythio or alkylsulfonyl)-acetophenones.
    Type: Grant
    Filed: February 4, 1991
    Date of Patent: March 31, 1992
    Assignee: Imperial Chemical Industries plc
    Inventor: Richard W. Brown
  • Patent number: 5097068
    Abstract: Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4-trisubstituted benzoyl)-1,3-cyclohexandediones. The intermediate benzoic acids of this invention have the following structural formula ##STR1## wherein R.sup.6 is chlorine, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or hydroxy; n is the integer 0 or 2; and R.sup.7 is C.sub.1 -C.sub.4 alkyl.
    Type: Grant
    Filed: December 7, 1989
    Date of Patent: March 17, 1992
    Assignee: ICI Americas, Inc.
    Inventor: David L. Lee
  • Patent number: 5095150
    Abstract: A formylated alkylbenzenesulfonyl halide compound represented by the following general formula (I): ##STR1## wherein R.sub.1 is an alkyl group having 1 to 5 carbon atoms; R.sub.2 and R.sub.3 are each a member selected from the group consisting of a hydrogen atom and alkyl groups having 1 to 5 carbon atoms; X is a halogen atom; the sulfonyl halide group is present at the ortho or para position while the formyl group at the para or ortho position relative to the group R.sub.1 when R.sub.2 and R.sub.3 are both a hydrogen atom, while the sulfonyl halide group and the formyl group are present at the para positions relative to the groups R.sub.1 and R.sub.2, respectively, when R.sub.2 is an alkyl group and R.sub.3 is a hydrogen atom, or the sulfonylhalide group and the formyl group are present at the para positions relative to the groups R.sub.1 and R.sub.2, respectively, when R.sub.2 and R.sub.
    Type: Grant
    Filed: March 25, 1991
    Date of Patent: March 10, 1992
    Assignee: Agency of Industrial Science & Technology
    Inventors: Yoshie Souma, Jun Iyoda, Hirosi Sano
  • Patent number: 5094685
    Abstract: A substituted benzoyl derivative having the formula: ##STR1## wherein X.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, cyano, nitro or halogen; X.sub.2 is --L--OR.sub.1 (wherein L is C.sub.1 -C.sub.4 alkylene or C.sub.1 -C.sub.4 alkylidene, and R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl), --L--O--L--OR.sub.1 (wherein L and R.sub.1 are as defined above), --L--S(O).sub.n --R.sub.2 (wherein L is as defined above, R.sub.2 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl, and n is an integer of 0, 1 or 2), --L--O--COR.sub.2 (wherein L and R.sub.2 are as defined above), --L--NR.sub.1 R.sub.3 (wherein L and R.sub.1 are as defined above, and R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl), --COOR.sub.1 (wherein R.sub.1 is as defined above) or --COO--L--O--R.sub.1 (wherein L and R.sub.1 are as defined above), provided that when X.sub.
    Type: Grant
    Filed: June 13, 1990
    Date of Patent: March 10, 1992
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Masatoshi Baba, Takuya Kakuta, Norio Tanaka, Eiichi Oya, Takashi Ikai, Tsutomu Nawamaki, Shigeomi Watanabe, Koichi Suzuki
  • Patent number: 5092919
    Abstract: Herbicidal compounds of the structural formula ##STR1## wherein 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; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.4 is hydroxy, hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are carbonyl (.dbd.O) with the proviso that R.sup.1, R.sup.2, R.sup.5 and R.sup.6 are C.sub.1 -C.sub.4 alkyl; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, or C.sub.1 -C.sub.4 alkylsulfonyl, with the proviso that when R.sup.6 is C.sub.1 -C.sub.4 alkylthio or C.sub.1 -C.sub.4 alkylsulfonyl, the R.sub.3 and R.sup.4 are not together carbonyl; R.sup.7 is methyl or ethyl; and R.sup.8 is (1) halogen; (2) nitro; or (3) R.sup.b SO.sub.n -- wherein n is the integer 0 or 2, and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; and its salts.
    Type: Grant
    Filed: January 15, 1991
    Date of Patent: March 3, 1992
    Assignee: Imperial Chemical Industries plc
    Inventor: Nhan H. Nguyen
  • Patent number: 5089647
    Abstract: This invention provides a novel method for the preparation of optically active arylalykylsulfone derivatives, having a chiral center in the alkyl moiety in either the (R)- or the (S)-configuration. These optically active sulfones find use in the stereospecific synthesis of steroid or vitamin D compounds having chiral center at either carbon 24 or carbon 25 of the side chain. The method comprises the steps of reacting an optically active sulfinate ester having a chiral center at sulfur with a racemic alkyl Grignard reagent to obtain a mixture of diastereomeric sulfoxides, separating the mixture of diastereomeric sulfoxides, and oxidizing separately each of the diastereomers to obtain the desired optically active sulfone.
    Type: Grant
    Filed: April 11, 1990
    Date of Patent: February 18, 1992
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman
  • Patent number: 5087743
    Abstract: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: January 23, 1990
    Date of Patent: February 11, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5085688
    Abstract: Herbicidal compounds of the formula ##STR1## wherein R.sub.3 is methoxy or ethoxy; andR.sub.4 is bromine, methylsulfonyl or ethylsulfonyland their salts.
    Type: Grant
    Filed: November 1, 1990
    Date of Patent: February 4, 1992
    Assignee: ICI Americas Inc.
    Inventors: William J. Michaely, Gary W. Kraatz
  • Patent number: 5084478
    Abstract: A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl;wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent or each is hydrogen or alkyl, alkoxy or dialkylamino, provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent;wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkylwherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --;and wherein R.sup.9 is alkyl of up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: January 28, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, Howard Tucker
  • Patent number: 5075339
    Abstract: The invention relates to benzylketone phospholipase A.sub.2 inhibitors, pharmaceutical compositions containing them, and methods of treating phospholipase A.sub.2 -mediated conditions in mammals by administration of a therapeutically effective amount of such a benzylketone phospholipase A.sub.2 inhibitor. These compounds are also intermediates in the synthesis of other PLA.sub.2 inhibitors.
    Type: Grant
    Filed: June 1, 1990
    Date of Patent: December 24, 1991
    Assignee: Du Pont Merck Pharmaceutical Company
    Inventor: Wendell W. Wilkerson
  • Patent number: 5055605
    Abstract: The process of the present invention relates to the preparation of precursor trisubstituted benzoic acid intermediates having the structural formula ##STR1## wherein R is --COOR.sup.a wherein R.sup.a is C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.4 alkyl; formyl or C(O)R.sup.b wherein R.sup.b is C.sub.1 -C.sub.4 alkyl;R.sup.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy or trifluoromethyl;R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl --OCH.sub.2 CH.sub.2 OCH.sub.3, --OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 or a substituted methyl group andR.sup.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl.
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: October 8, 1991
    Assignee: Imperial Chemical Industries plc
    Inventor: Charles N. Ludvik
  • Patent number: 5041681
    Abstract: Process for the preparation of herbicidally active substituted cyclohexan-1,3,5-triones which comprises either(a) reacting a compound of formula (II) ##STR1## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are, for example, hydrogen or C.sub.1 -C.sub.4 alkyl with a compound of formula (III):R.sup.1 COCN (III)wherein R.sup.1 is optionally substituted aryl in the presence of a base and a Lewis acid; or(b) reacting a compound of formula (VI) ##STR2## with a compound of formula (X) ##STR3## in the presence of a Lewis acid; or (c) where R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same, reacting a compound of formula (XI) ##STR4## with a compound of formula R.sup.2 X' in the presence of a base, wherein X' is a leaving group.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: August 20, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventor: Glynn Mitchell
  • Patent number: 5041600
    Abstract: Arylcyclobutenealkyl diethers of oligomers containing a plurality of aromatic rings at least two of which are joined by a sulfone moiety, are self-curing at temperatures above about 150.degree. C. The cured products exhibit good properties of strength and toughness.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: August 20, 1991
    Assignee: Shell Oil Company
    Inventor: Pui K. Wong
  • Patent number: 5015775
    Abstract: Alkyl aryl sulfones of the formula R--SO.sub.2 --AR--Y.sub.n, wherein Ar is an aryl compound, Y is a substituent on the aryl compound and R is alkyl or cycloalkyl, and liquid mixtures of positional isomers of the same are prepared by reacting an aryl compound of the formula Ar--Y.sub.n, with an alkyl sulfonic acid of the formula R--SO.sub.3 H and a phosphorus reagent, preferably under heat. Particularly good yields and pure products are obtained using phosphorus pentoxide. Alkyl aryl sulfones produced by this method are a liquid mixture preferably containing at least two positional isomers, wherein no isomer is present in an amount of more than about 50% of the isomer mixture.
    Type: Grant
    Filed: March 31, 1988
    Date of Patent: May 14, 1991
    Assignee: Atochem North America, Inc.
    Inventors: James L. Reilly, Gordon R. Leader
  • Patent number: 4997473
    Abstract: Compunds of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, nitro, C.sub.1 C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio or C.sub.1 C.sub.2 alkylsulfonyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.2 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.2 alkyl; R.sup.3 is hydrogen or C.sub.1 -C.sub.2 alkyl; and R.sup.4 and R.sup.5 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.n - wherein n 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.4 alkyl; (11) R.sup.3 C(O)- wherein R.sup.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.
    Type: Grant
    Filed: August 24, 1989
    Date of Patent: March 5, 1991
    Assignee: ICI Americas Inc.
    Inventor: Nhan H. Nguyen
  • Patent number: 4980509
    Abstract: An aromatic polycyclic compound has the formula ##STR1## wherein R represents --SO.sub.3 H, SO.sub.2 NHR.sub.3, ##STR2## --SO.sub.2 R.sub.3, --SOR.sub.3 or --SR.sub.3, R.sub.3 represents lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aminoalkyl, carboxyalkyl, aminocarboxyalkyl or alkoxyalkyl,R' represents hydrogen, lower alkyl, lower alkoxy, hydroxy, C.sub.1 -C.sub.4 acyloxy or amino,R" represents hydrogen, lower alkyl or lower alkoxy, orR' and R", taken together, form an oxo, methano or hydroxyimino radical,R.sub.1 represents hydrogen or lower alkyl,n is 0 or 1,when n=1, R.sub.2 represents hydrogen or lower alkyl, or R.sub.1 and R.sub.2, taken together form a vinylene radical, andAr represents an aromatic radical selected from ##STR3## wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 represent hydrogen or lower alkyl, at least one of R.sub.4 and/or R.sub.5 being other than hydrogen, and at least two of R.sub.8 -R.sub.
    Type: Grant
    Filed: July 1, 1988
    Date of Patent: December 25, 1990
    Assignee: Societe Anonyme dite: L'Oreal
    Inventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle
  • Patent number: 4957538
    Abstract: Herbicidal compounds of the structural formula ##STR1## wherein X is oxygen or sulfur; R is chlorine or bromine; 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; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydroxy, hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are carbonyl (.dbd.0) with the proviso that R.sup.1 , R.sup.2, R.sup.5 and R.sup.6 are all C.sub.1 -C.sub.4 alkyl; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, or C.sub.1 -C.sub.4 alkylsulfonyl, with the proviso that when R.sup.6 is C.sub.1 -C.sub.4 alkylthio or C.sub.1 -C.sub.4 alkylsulfonyl, then R.sup.3 and R.sup.4 are not together carbonyl; R.sup.7 is methyl or ethyl; and R.sup.8 is (1) halogen; (2) nitro; or (3) R.sup. b SO.sub.n --wherein n is the integer 0 or 2; and R.sup.b is (a) C.sub.1 -C.sub.3 alkyl; and their salts.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: September 18, 1990
    Assignee: ICI Americas Inc.
    Inventor: William J. Michaely
  • Patent number: 4956109
    Abstract: Herein disclosed is a lubricating oil comprising at least one member selected from the group consisting of esterified products obtained by reacting: (A) a compound selected from the group consisting of alcohols represented by the following general formula (I), alcohols represented by the following general formula (II) and hydrogenated derivatives thereof; with (B) a fatty acid having not less than 6 carbon atoms or a mixture of the fatty acid with a rosin selected from the group consisting of rosin, hydrogenated rosins, disproportionated rosins and polymerized rosins: ##STR1## in the general formulas (I) and (II), X.sub.1 and X.sub.2 each independently represents a hydrogen atom or a methyl group and n is an integer ranging from 0 to 10. The lubricating oil is used as rolling mill oils, hydraulic oils cutting-grinding oils, lubricating oils for metal plastic working and those for internal combustion engines.
    Type: Grant
    Filed: May 26, 1989
    Date of Patent: September 11, 1990
    Assignees: The Nisshin Oil Mills, Ltd., Nippon Steel Corporation
    Inventors: Keiichi Tanikawa, Higaki Yuzo
  • Patent number: 4954165
    Abstract: An herbicidally effective benzoyl derivative having the formula: ##STR1## wherein X.sub.1 is C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.5 is hydrogen or fluorine;Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.1 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.3 alkyl;n is an integer of 0, 1 or 2 is discosed.In addition, the herbicidally effective benzoyl derivative having the formula: ##STR2## wherein: X.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy halogen;X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.5 is hydrogen or fluorine;Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.1 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.3 alkyl;n is an integer of 0, 1 or 2;L is C.sub.1 -C.sub.4 alkylene is disclosed.
    Type: Grant
    Filed: October 18, 1988
    Date of Patent: September 4, 1990
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Masatoshi Baba, Takuya Kakuta, Norio Tanaka, Eiichi Oya, Takashi Ikai, Tsutomu Nawamaki, Shigeomi Watanabe, Koichi Suzuki
  • Patent number: 4946992
    Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formulas HO[--CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H or HO[--CH.sub.2 C(CH.sub.2 X--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H are prepared from halogenated neopentyl glycols or oxetanes and thiols of the formula R.sub.f --E--SH, amines of the formuls R.sub.f --E--NH--R, alcohols of the formula R.sub.f --E--OH or perfluoro-amides, wherein R.sub.f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms.The polymeric reaction products of said fluorinated diols, and optionally other diols with isocyanates to prepare polyurethanes; with amines and isocyanated to prepare polyureas/polyurethanes; with acids or derivatives to prepare polyesters or polycarbonates are disclosed. These include polymeric, random or block urethane, and/or urea, and/or ester compositions containing the residue of at least one R.sub.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: August 7, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert A. Falk, Kirtland P. Clark, Athanasios Karydas, Michael Jacobson
  • Patent number: 4937388
    Abstract: The invention provides insecticidally active compounds of formula I: ##STR1## wherein A is selected from oxygen and a group of formula S(O).sub.n, where n represents 0, 1 or 2; W represents one or two substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy, or W represents a bidentate group linking adjacent carbon atoms, selected from alkylene and alkylenedioxy; Y represents a substituted aryl group where each substituent is selected from halo, alkyl, aryl, aralkyl, aryloxy and arylamino; Z represents a fluoroalkyl group of up to two carbon atoms; and either X' represents hydrogen and X is selected from hydrogen, halo, hydroxy, alkoxy and acyloxy, or X and X' together represent a second bond between the adjacent carbon atoms.The invention also provides processes and intermediates useful for the preparation of the compounds of formula I, insecticidal compositions comprising the compounds of formula I, and methods of combating and controlling pests therewith.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: June 26, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr
  • Patent number: 4937386
    Abstract: The present invention relates to 4,4,5-trimethyl-2-(2-nitro-4-methylsulfonylbenzoyl) cyclohexane-1,3-dione which is useful as herbicide.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: June 26, 1990
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Akiyoshi Ueda, Hideo Hosaka
  • Patent number: 4922014
    Abstract: Process for the preparation of oxethylmercaptobenzaldehydes and their oxidation products of the formula (I) ##STR1## in which R denotes a hydrogen, fluorine, chlorine, bromine or iodine atom, m denotes the number 0 or 2, n denotes the number 1 or 2, and p denotes the number 0 or 1, with the proviso that p is 0 if m is 0, and the side-chain --S(0).sub.m --CH.sub.2 --CH.sub.2 --OH is in the ortho and/or para position to the aldehyde or carboxyl group, can be prepared by condensing 1 mole of a halobenzaldehyde of the general formula (II) ##STR2## in which R, X, Y and Z represent hydrogen, fluorine, chlorine, bromine or iodine atoms, with the proviso that R, X, Y and Z can be in total 1, 2 or 3 halogen atoms, where R is a halogen atom if R, X, Y and Z together represent 3 halogen atoms, in aqueous medium with about 1.0 to 1.5 moles of mercaptoethanol (per halogen atom to be exchanged) in the presence of the acid-binding agents at or about 70.degree. C. about 150.degree. C.
    Type: Grant
    Filed: September 20, 1988
    Date of Patent: May 1, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Theodor Papenfuhs
  • Patent number: 4909835
    Abstract: The invention relates to novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof with herbicidal and plant growth regulating properties.The novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof are of the formula I ##STR1## wherein A is a 2- or 7-membered alkylene bridge, or a 3- to 7-membered alkenylene bridge which may be mono- or polyunsaturated,n is 0, 1 or 2,R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; or is C.sub.3 -C.sub.6 cycloalkyl; or phenyl, benzyl or phenylethyl, the phenyl ring of each of which may be substituted by ahlogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, cyano or nitro,X is oxygen or a radical --NOR.sub.3, andR.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.
    Type: Grant
    Filed: February 24, 1988
    Date of Patent: March 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans Tobler
  • Patent number: 4898981
    Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formula HO[--CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H prepared from halogenated neopentyl glycols and thiols of the formula R.sub.f --E--SH, or amines of the formula R.sub.f --E--NH--R wherein R.sub.f is a hydrophonic, olephobic fluoroaliphatic group of up to 20 carbon atoms, E is alkylene of up to 10 carbon atoms, optionally interrupted by up to three groups including --NR, --O, --S--, --SO.sub.2 --, --O.sub.2 C, CONR, and --SO.sub.2 NR, and X is S,SO.sub.2 or NR.sub.2, where R is independently hydrogen, alkyl, or hydroxyalkyl of 1 to 6 carbon atoms are described.The polymeric reaction products of said fluorinated diols, and optionally other diols with isocyanates to prepare polyurethanes; with amines and isocyanates, to prepare polyureas/polyurethanes; with acids or derivatives, to prepare polyesters or polycarbonates are disclosed.
    Type: Grant
    Filed: June 20, 1988
    Date of Patent: February 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert A. Falk, Kirtland P. Clark, Athanasios Karydas
  • Patent number: 4883887
    Abstract: A process for producing carotenoids and carotenoid intermediates via reduction of sulfonyl polyenes with a dithionite in the presence of ammonia or an aliphatic amine, including novel intermediates in this process, which carotenoids are known coloring agents for foodstuffs, animal feeds, pharmaceuticals, etc.
    Type: Grant
    Filed: July 1, 1988
    Date of Patent: November 28, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kurt Bernhard, Stephan Jaggli, Paul Kreienbuhl, Ulrich Schwieter
  • Patent number: 4877899
    Abstract: Sulfur-substituted alkenyl compounds, synthesis thereof, intermediates therefor, and the use of the compounds to control pests.
    Type: Grant
    Filed: November 23, 1983
    Date of Patent: October 31, 1989
    Assignee: Sandoz Ltd.
    Inventors: Robert L. Carney, Thomas L. Brown
  • Patent number: 4869748
    Abstract: Herbicidal compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n - wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;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;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; andR.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.n - wherein n 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.4 alkyl; (11) R.sup.e C(O)- wherein R.sup.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: September 26, 1989
    Assignee: ICI Americas Inc.
    Inventor: Christopher G. Knudsen
  • Patent number: 4867784
    Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2, A, m, n, x and y have the meanings given in the disclosure, a process for their manufacture, herbicidal and plant growth-regulating agents containing the novel active ingredients, and processes for combating unwanted plant growth and for regulating plant growth.
    Type: Grant
    Filed: January 14, 1987
    Date of Patent: September 19, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Keil, Wolfgang Spiegler, Dieter Jahn, Dieter Kolassa, Ulrich Schirmer, Bruno Wuerzer, Norbert Meyer, Wilhelm Rademacher, Johann Jung