Benzene Ring Bonded Directly To The Carbonyl Patents (Class 558/415)
  • Patent number: 6013836
    Abstract: This invention relates to N'-substituted-N,N'-disubstitutedhydrazines of formula I ##STR1## wherein X and X' are independently O, S, or NR; A' and B' are independently substituted or unsubstituted aryl or aromatic heterocycle; wherein F is alkyl, alkenyl, or aralkyl; and wherein E is a tertiary carbon containing organic radical having a total of at least four carbon and halogen atoms but not more than six halogen atoms, or a non-tertiary carbon containing non-haloalkyl organic or organometallic radical having at least five atoms other than hydrogen, oxygen and halogen which are useful as insecticides, compositions containing those compounds, methods of producing the compounds, and methods of their use. More particularly, the invention relates to insect growth regulating compounds and compositions, and methods of using such compounds and compositions. Compounds of the present invention are particularly suitable for controlling plant-destructive insects in crops of cultivated plants, ornamentals and forestry.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: January 11, 2000
    Assignee: Rohm and Haas Company
    Inventors: Adam Chi-Tung Hsu, Harold Ernest Aller, Dat Phat Le, Donald Wesley Hamp, Barry Weinstein, Raymond August Murphy
  • Patent number: 6011063
    Abstract: Ortho-substituted benzoylguanidines of the formula I ##STR1## in which R(1) to R(5) have the meanings given in the claims, are suitable as antiarrhythmic pharmaceuticals having a cardioprotective component for infarct prophylaxis and for infarct treatment and also for the treatment of angina pectoris. They also inhibit in a preventive manner the pathophysiological processes in the formation of ischemically induced damage, in particular in the illicitation of ischemically induced cardiac arrhythmias.
    Type: Grant
    Filed: June 3, 1997
    Date of Patent: January 4, 2000
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Weichert, Joachim Brendel, Heinz-Werner Kleemann, Hans Jochen Lang, Jan-Robert Schwark, Udo Albus, Wolfgang Scholz
  • Patent number: 5945450
    Abstract: Naphthalene derivatives represented by formula ?I!: ##STR1## (wherein A is a hydrogen atom, a hydroxy group, a C.sub.7 -C.sub.11 aralkyloxy group, or an alkoxy group composed of an oxy group and a C.sub.1 -C.sub.12 aliphatic or alicyclic, saturated or unsaturated hydrocarbon group where the allyl may be substituted with a C.sub.6 -C.sub.10 allyloxy group; Q represents O, S, CH.sub.2, O--CH.sub.2, S--CH.sub.2, CO, or CHOR.sup.1 ; L represents CO, CR.sup.2 R.sup.3 CO, CH.sub.2 CH.sub.2 CO, or CH.dbd.CHCO; D represents a hydrogen atom, NO.sub.2, NH.sub.2, CO.sub.2 R.sup.4, or a group having the following formula ?II!: ##STR2## (wherein G represents. a hydrogen atom, OH, SO.sub.2 NH.sub.2, CO.sub.2 R.sup.6, CN, or a tetrazol-5-yl group); E represents a hydrogen atom, OH, SO.sub.2 NH.sub.2, CO.sub.2 R.sup.5, CN, or a tetrazol-5-yl group; M represents a hydrogen atom, a C.sub.1 -C.sub.4 lower alkyl group, a nitro group, or a halogen atom; and R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.
    Type: Grant
    Filed: November 22, 1996
    Date of Patent: August 31, 1999
    Assignee: Teijin Limited
    Inventors: Kazuya Takenouchi, Katsushi Takahashi, Masaichi Hasegawa, Takahiro Takeuchi, Keiji Komoriya
  • Patent number: 5900432
    Abstract: Compounds of formula I: ##STR1## wherein, ring C, A--B, R.sup.1, n, R.sup.2, and R.sup.3 have any of the meanings given in the specification, and their pharmaceutically acceptable salts are useful in the treatment of urinery incontinence. Also disclosed are pharmaceutical compositions, processes for preparing the compounds of formula I and intermediates.
    Type: Grant
    Filed: October 12, 1995
    Date of Patent: May 4, 1999
    Assignee: Zeneca Limited
    Inventors: James Roy Empfield, Cyrus John Ohnmacht, Keith Russell, Diane Amy Trainor, Paul James Warwick, Jr.
  • Patent number: 5880156
    Abstract: Substituted benzoylguanidines, process for their preparation, their use as a pharmaceutical or diagnostic, and pharmaceutical containing them Benzoylguanidines of the formula I ##STR1## are described in which: R(1), R(2), R(3), R(4) are as defined in the specification, and pharmaceutically tolerated salts thereof.
    Type: Grant
    Filed: January 30, 1996
    Date of Patent: March 9, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Jochen Lang, Heinz-Werner Kleemann, Wolfgang Scholz, Udo Albus
  • Patent number: 5880147
    Abstract: Compounds of formula (I): ##STR1## wherein: R.sup.1 is alkyl; R.sup.2a, R.sup.2b, R.sup.2c and R.sup.2d are the same or different and each is hydrogen, optionally substituted alkyl, --(C.dbd.O)--B.sup.1 (wherein B.sup.1 is hydrogen or alkyl), nitro, --NR.sup.c R.sup.d (wherein R.sup.c is hydrogen or alkyl and Rd is alkyl), hydroxy, protected hydroxy group, alkoxy, cyano, alkylthio, alkylsulfinyl, alkylsulfonyl or halogen;R.sup.3 is alkyl; R.sup.4 is a group of the formula (II) ##STR2## wherein A.sup.1 is a single bond, alkylene or alkenylene; R.sup.5a and R.sup.5b are the same or different and each is hydrogen, alkyl or --A.sup.4 R.sup.5.sub.c wherein A is a single bond, alkylene or alkenylene and R.sup.5.sub.c is alkoxy; and n is 0, and pharmaceutically acceptable salts thereof. Such compounds have valuable inhibitory activity against acyl-CoA (cholesterol acyl transferase).
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: March 9, 1999
    Assignee: Sankyo Company, Limited
    Inventors: Akira Yoshida, Kozo Oda, Takashi Kasai, Kousei Shimada, Hiroshi Kogen, Ichiro Hayakawa, Sadao Ishihara, Teiichiro Koga, Eiichi Kitazawa, Taro Tokui
  • Patent number: 5874615
    Abstract: The present invention provides an improved method for the preparation of an insecticidal benzoylurea having the structural formula I ##STR1##
    Type: Grant
    Filed: March 17, 1998
    Date of Patent: February 23, 1999
    Inventors: Pieter Adriaan Verbrugge, Jannetje De Waal
  • Patent number: 5866610
    Abstract: Substituted benzoylguanidines, process for their preparation, their use as a pharmaceutical or diagnostic, and pharmaceutical containing them.Described are benzoylguanidines of the formula I ##STR1## where R(1) to R(3) are H, Hal, (cyclo)alkyl, N.sub.3, CN or OH, alkyloxy, phenyl, phenoxy or benzoyl, and their pharmacologically acceptable salts, but with the exception of the compounds benzoylguanidine, 4-chlorobenzoylguanidine, 3,4-dichlorobenzoylguanidine and 3- or 4-methylbenzoylguanidine.They are obtained by reacting a compound II ##STR2## with guanidine, L being a leaving group.
    Type: Grant
    Filed: July 18, 1996
    Date of Patent: February 2, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Jochen Lang, Andreas Weichert, Heinz-Werner Kleemann, Jan-Robert Schwark, Wolfgang Scholz, Udo Albus
  • Patent number: 5841001
    Abstract: The present invention provides an industrially advantageous process for the preparation of an optically active 2-halo-1-(substituted phenyl)ethanol useful as medicines, agricultural chemicals or as intermediates thereof; and a simple process for the preparation of an optically active substituted styrene oxide or 2-amino-1-(substituted phenyl)ethanol useful as medicines, agricultural chemicals or intermediates thereof. A 2-halo-1-(substituted phenyl)ethanol represented by the following general formula (I) is allowed to contact, in the presence of a carboxylic anhydride, with an enzyme stereoselectively catalyzing ester interchange to produce an optically active 2-halo-1-(substituted phenyl)ethanol: ##STR1## (wherein X represents a chlorine atom or a bromine atom, and R.sup.1, R.sup.2 and R.sup.3 may be the same or different and each represent a hydrogen atom, a halogen atom, a C.sub.1-5 alkyl group, a C.sub.1-5 haloalkyl group, a C.sub.
    Type: Grant
    Filed: February 28, 1997
    Date of Patent: November 24, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Ken Tanaka, Mari Yasuda, Makoto Ueda
  • Patent number: 5840761
    Abstract: Alkylbenzoylguanidines of the formula I ##STR1## in which A, R.sup.1, R.sup.2 and R.sup.3 have the given meanings, and their physiologically harmless salts exhibit antiarrhythmic properties and act as inhibitor of the cellular Na.sup.+ /H.sup.+ antiporter.
    Type: Grant
    Filed: August 30, 1995
    Date of Patent: November 24, 1998
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Rolf Gericke, Dieter Dorsch, Manfred Baumgarth, Klaus-Otto Minck, Norbert Beier
  • Patent number: 5731351
    Abstract: Alkyl-benzoylguanidines of the formula I ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 have the meanings given, and physiologically acceptable salts thereof show antiarrhythmic properties and act as inhibitors of the cellular Na.sup.+ /H.sup.+ antiporter.
    Type: Grant
    Filed: August 23, 1996
    Date of Patent: March 24, 1998
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Rolf Gericke, Manfred Baumgarth, Klaus-Otto Minck, Norbert Beier
  • Patent number: 5705703
    Abstract: Catechol derivatives of the formula ##STR1## wherein Ra, Rb and Rc have the significance given herein. the ester and ether derivatives thereof which are hydrolyzable under physiological conditions and the pharmaceutically acceptable salts thereof are described and possess valuable pharmacological properties. In particular, they inhibit the enzyme catechol-O-methyltransferase (COMT), a soluble, magnesium-dependent enzyme which catalyses the transference of the methyl group of S-adenosylmethionine to a catechol substrate, whereby the corresponding methyl ethers are formed. Suitable substrates which can be O-methylated by COMT and which can thus be deactivated are, for example, extraneuronal catecholamines and exogeneously-administered therapeutically active substances having a catechol structure.Formula Ia above embraces not only compounds which form part of the invention, but also known compounds: the compounds which form part of the invention can be prepared according to known methods.
    Type: Grant
    Filed: January 21, 1997
    Date of Patent: January 6, 1998
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Karl Bernauer, Janos Borgulya, Hans Bruderer, Mose Da Prada, Gerhard Zurcher
  • Patent number: 5679712
    Abstract: Benzoylguanidines of the formula I ##STR1## are described in which: R(1), R(2), R(3), R(4), R(5) are as defined in the specification, and pharmaceutically tolerated salts thereof.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: October 21, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jan-Robert Schwark, Heinz-Werner Kleemann, Hans-Jochen Lang, Andreas Weichert, Wolfgang Scholz, Udo Albus
  • Patent number: 5672750
    Abstract: The present invention is directed to a process for preparing an aromatic amide. More specifically, the process involves reacting carbon monoxide, an amine and an aromatic chloride in the presence of an iodide or bromide salt, a catalyst, and a base.
    Type: Grant
    Filed: May 31, 1996
    Date of Patent: September 30, 1997
    Assignee: Eastman Chemical Company
    Inventor: Robert James Perry
  • Patent number: 5656619
    Abstract: Abstract of the Disclosure: 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: June 6, 1995
    Date of Patent: August 12, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5637771
    Abstract: A method of lowering cholesterol which comprises administering to a host requiring such treatment an effective amount of a compound of the formula ##STR1## wherein one of R.sup.1 and R.sup.2 is C.sub.1-7 -alkyl and the other is C.sub.1-7 -alkyl or C.sub.2-6 -alkenyl-methyl;L is C.sub.1-11 -alkylene or C.sub.2-11 -alkenylene optionally bonded to the phenyl group via an O atom or L is 1,4-phenylene;n is 0 or, when L contains an O atom, n is 0 or 1;Q is C.sub.1-7 -alkyl, C.sub.2-10 -alkenyl or a group of formula ##STR2## wherein R is H, halogen, CF.sub.3, CN or NO.sub.2 ; R.sup.3 and R.sup.4 are H, C.sub.1-4 -alkyl or halogen; andR.sup.5 is H or, when R is H, R.sup.5 is H or halogen;or a pharmaceutically acceptable acid addition salt thereof, as well as certain compounds of formula I, are described.
    Type: Grant
    Filed: November 8, 1995
    Date of Patent: June 10, 1997
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Johannes Aebi, Philipe Guerry, Synese Jolidon, Olivier Morand
  • Patent number: 5629346
    Abstract: Certain N-acetonylbenzamides exhibit low toxicity to plants are particularly useful for control of fungi, especially Phycomycetes.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 13, 1997
    Assignee: Rohm and Haas Company
    Inventors: H. Edwin Carley, Ashok K. Sharma, Colin Swithenbank
  • Patent number: 5616799
    Abstract: A process for the preparation of glycoloylanilide of the formula (G) ##STR1## is recited that involves reacting a nitrobenzene with hydrogen and, if desired, with a carbonyl compound, in the presence of a noble metal catalyst and a solvent, reacting the compound produced with chloroacetyl chloride, reacting the resulting product with a benzyl alcohol and with a base, or reacting the resulting compound with an O-benzylglycoloyl chloride, and debenzylating the resulting benzylglycoloylanilide product by reacting with hydrogen in the presence of a noble metal catalyst. The invention also relates to a process for the preparation of O-benzylglycoloylanilide.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: April 1, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegfried Planker, Theodor Papenfuhs
  • Patent number: 5610191
    Abstract: Thioamides of the formula I ##STR1## where A, B, R' are hydrogen, cyano, alkyl, alkoxy or halogen,X is .dbd.CHCH.sub.3 or .dbd.N--OCH.sub.3,R.sup.1, R.sup.2 are hydrogen or alky1,Y is a group ##STR2## R is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted aryl or unsubstituted or substituted hetaryl,and pesticides containing these compounds.
    Type: Grant
    Filed: November 22, 1995
    Date of Patent: March 11, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Wingert, Hubert Sauter, Herbert Bayer, Klaus Oberdorf, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5607953
    Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydroben or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.
    Type: Grant
    Filed: November 23, 1994
    Date of Patent: March 4, 1997
    Assignee: Eisai Co., Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • Patent number: 5571842
    Abstract: Perfluoroalkyl-substituted benzoylguanidines, a process for their preparation, their use as a medicament or diagnostic agent, and a medicament containing themA description is given of perfluoroalkyl-substituted benzoylguanidines of the formula I ##STR1## where R(1) is (C.sub.1 -C.sub.6)-perfluoroalkyl-SO.sub.m ; R(2) and R(3) are H, halogen, alk(yl)(oxy), phenoxy; R(4) and R(5) are H, alkyl, Hal, CN, OR(7), NR(8)R(9), --(CH.sub.2).sub.n --(CF.sub.2).sub.o --CF.sub.3 and of the pharmacologically acceptable salts thereof; the compounds I are obtained by reacting a compound II ##STR2## with guanidine, L being a leaving group which is able readily to undergo nucleophilic substitution.
    Type: Grant
    Filed: May 11, 1995
    Date of Patent: November 5, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz-Werner Kleemann, Hans-Jochen Lang, Jan-Robert Schwark, Andreas Weichert, Wolfgang Scholz, Udo Albus
  • Patent number: 5550280
    Abstract: Compounds of the formula ##STR1## wherein X is O or S;Y is O or S;R.sup.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 alkynyloxy, mono-, di- or tri-halomethyl, trifluoromethoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.3 -C.sub.4 branched alkylthio, nitro, or cyano;R.sup.3 is hydrogen, halogen, methyl, mono-, di- or tri-halomethyl;R.sup.4 isa) C.sub.3 -C.sub.8 cycloalkyl substituted by one or more C.sub.1 -C.sub.4 alkyl, preferably one or two methyl;orb) ##STR2## wherein R.sup.6 and R.sup.7 are independently, hydrogen or linear or branched, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, or C.sub.2 -C.sub.4 alkynyl, and R.sup.8 is C.sub.3 -C.sub.8 cycloalkyl substituted by one or more C.sub.1 -C.sub.4 alkyl; andR.sup.5 is an acyclic or cyclic side chain as defined herein.
    Type: Grant
    Filed: November 30, 1994
    Date of Patent: August 27, 1996
    Assignee: Uniroyal Chemical Ltd./ Uniroyal Chemical Ltee
    Inventors: Dong Dao-Cong, William A. Harrison
  • Patent number: 5495048
    Abstract: A method of lowering cholesterol which comprises administering to a host requiring such treatment an effective amount of a compound of the formula ##STR1## wherein one of R.sup.1 and R.sup.2 is C.sub.1-7 -alkyl and the other is C.sub.1-7 -alkyl or C.sub.2-6 -alkenyl-methyl;L is C.sub.1-11 -alkylene or C.sub.2-11 -alkenylene optionally bonded to the phenyl group via an O atom or L is 1,4-phenylene;n is 0 or, when L contains an O atom, n is 0 or 1;Q is C.sub.1-7 -alkyl, C.sub.2-10 -alkenyl or a group of formula ##STR2## wherein R is H, halogen, CF.sub.3, CN or NO.sub.2 ; R.sup.3 and R.sup.4 are H, C.sub.1-4 -alkyl or halogen; andR.sup.5 is H or, when R is H, R.sup.5 is H or halogen;or a pharmaceutically acceptable acid addition salt thereof, as well as certain compounds of formula I, are described.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: February 27, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Johannes Aebi, Philipe Guerry, Synese Jolidon, Olivier Morand
  • Patent number: 5484551
    Abstract: Compounds containing a 4-[(E)-alk-2-enoyloxy]benzoate group and liquid crystalline mixtures which contain such compounds and the use of such compounds and, respectively, mixtures in electro-optical indicating devices.The compounds are of the formula ##STR1## wherein R.sup.1 is alkyl with 1 to 12 carbon atoms;X.sup.1, X.sup.3 each independently are halogen or hydrogen; andX.sup.2 is halogen or cyano.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: January 16, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Stephen Kelly, Martin Schadt
  • Patent number: 5482969
    Abstract: Compounds of formula I: ##STR1## wherein, ring C, A-B, R.sup.1, n, R.sup.2, and R.sup.3 have any of the meanings given in the specification, and their pharmaceutically acceptable salts are useful in the treatment of urinary incontinence. Also disclosed are pharmaceutical compositions, processes for preparing the compounds of formula I and intermediates.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: January 9, 1996
    Assignee: Zeneca Limited
    Inventors: James R. Empfield, Cyrus J. Ohnmacht, Keith Russell, Diane A. Trainor, Paul J. Warwick, Jr.
  • Patent number: 5478835
    Abstract: Disclosed is a tricyclic compound represented by the formula (I): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently represents hydrogen, C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, amino, C1-6 alkylamino, halogenated C1-6 alkyl, halogenated C1-6 alkoxy, halogen, nitro, cyano, carboxy, C1-6 alkoxycarbonyl, hydroxymethyl, CR.sup.9 R.sup.10 CO.sub.2 R.sup.11 (wherein each of R.sup.9, R.sup.10 and R.sup.11 independently represents hydrogen or C1-6 alkyl) or CONR.sup.12 R.sup.13 (wherein each of R.sup.12 and R.sup.13 independently represents hydrogen or C1-6-alkyl); R.sup.5 represents hydrogen or C1-6 alkyl; each of R.sup.6, R.sup.7 and R.sup.8 independently represents hydrogen, C1-6 alkyl, hydroxy, C1-6 alkoxy, C1-6 alkanoyloxy, C1-6 alkylthio, thiocyanato or halogen; X represents CH or N; Y.sup.1 -Y.sup.2 represents CH.sub.2 -O, CH.sub.2 -S(O).sub.n, (wherein n represents 0, 1, or 2), CH.sub.2 CH.sub.2, CH.dbd.CH or CON(R.sup.14) (wherein R.sup.
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: December 26, 1995
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Toshiaki Kumazawa, Masashi Yanase, Hiroyuki Harakawa, Hiroyuki Obase, Shoji Oda, Shiro Shirakura, Koji Yamada, Kazuhiro Kubo
  • Patent number: 5466712
    Abstract: The compound of the formula (I) or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants ##STR1##
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: November 14, 1995
    Assignee: American Home Products Corporation
    Inventors: John A. Butera, Schuyler A. Antane, Bradford H. Hirth
  • Patent number: 5464867
    Abstract: The compound of the formula (I) or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.
    Type: Grant
    Filed: November 16, 1994
    Date of Patent: November 7, 1995
    Assignee: American Home Products Corporation
    Inventors: Madelene M. Antane, John A. Butera, Bradford H. Hirth, Schuyler A. Antane
  • Patent number: 5463135
    Abstract: Fluorinated benzils and a process for their preparation A process for the preparation of fluorinated benzils of the formula (1) ##STR1## in which X.sub.1 -X.sub.6, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen, fluorine, chlorine or bromine atoms, or alkyl(C.sub.1 -C.sub.10), phenyl or naphthyl groups which may be substituted, or are groups reducing the electron density, at least one of the substituents X.sub.1 -X.sub.6 being a fluorine atom, by reacting 1 mol of a benzil of the formula (1), in which X.sub.1 -X.sub.6 and R.sub.1 and R.sub.2 have the abovementioned meanings, with the proviso that at least one of the substituents X.sub.1 -X.sub.6 is a chlorine atom, with about 0.8 to about 2.5 mol of potassium fluoride, rubidium fluoride, cesium fluoride or tetraalkyl (C.sub.1 -C.sub.18)-ammonium fluoride per chlorine atom to be exchanged, at temperatures of from about 100.degree. C. to about 280.degree. C.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: October 31, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Kanschik-Conradsen, Theodor Papenfuhs
  • 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: 5434186
    Abstract: Compounds of the formula ##STR1## wherein X is O or CH.sub.2 ; Y is O, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, or --OCH.sub.2 C.sub.6 H.sub.4 --;Z is --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--;f, h, k, m and t, independently, are 0 or 1;n is an integer from 1 to 12;R.sup.1 is hydrogen, lower alkyl, lower alkenyl, cycloalkyl, or aralkyl; and A is B or --O--B, wherein B is a mono-, di- or tricyclic aromatic or heteroaromatic moiety substituted by the group --COR.sup.2, --(O).sub.t --(W).sub.s --COR.sup.2 or --(CH.dbd.CH).sub.p COR.sup.2 and which may also contain up to 4 additional substituents selected, independently, from the group consisting of halogen, cyano, lower alkyl, lower alkoxy, sulfonamido, alkanoyl, aroyl, --(Q).sub.k --(W).sub.s' --E or --(Q).sub.k --(W).sub.s" --C.sub.6 H.sub.4 --(W).sub.s'" --E, provided that no more than one of said substituents is --(Q).sub.k --(W).sub.s' --E or --(Q).sub.k --(W).sub.s" --C.sub.6 H.sub.4 --(W).sub.s'" --E, and wherein E is COR.sup.
    Type: Grant
    Filed: September 28, 1993
    Date of Patent: July 18, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Ferdinand K. Lee, Keith A. Yagaloff
  • Patent number: 5430172
    Abstract: A process for preparing 4-alkanoylaryl benzyl ethers of the general formula I ##STR1## where R is hydrogen, halogen, cyano; alkyl, alkoxy;X is CH.sub.2, CH--CH.sub.3, CH--CH.sub.2 --CH.sub.3, CH--OCH.sub.3 or N--OCH.sub.3 ;Y is oxygen, sulfur, direct linkage or nitrogen;m is 0, 1, 2 or 3;R.sup.1 is hydrogen; alkyl, alkenyl, alkynyl or alkoxy;R.sup.2 is cyano, halogen, alkyl, alkoxy or haloalkyl;R.sup.3 is alkyl; haloalkyl; cycloalkyl; or an unsubstituted or substituted mono- to trinuclear aromatic system,comprises reacting an aryl benzyl ether of the general formula II ##STR2## where X, Y, R, R.sup.1, R.sup.2 and m have the abovementioned meanings, with a carbonyl halide or with a carboxylic anhydride or with a carboxylic sulfonic anhydride in the presence of an acid and in the presence or absence of a diluent.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: July 4, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Wassilios Grammenos, Wolfgang Siegel, Klaus Oberdorf, Bernd Mueller, Hubert Sauter, Reinhard Doetzer
  • Patent number: 5414125
    Abstract: A diamino-alpha-alkylstilbene useful as an epoxy resin curing agent is represented by the following Formula I: ##STR1## wherein R is independently hydrogen, a C.sub.1 -C.sub.10 hydrocarbyl(oxy) group or a halogen, nitro, nitrile, phenyl or --CO--R.sup.1 group wherein R.sup.1 is independently hydrogen or a C.sub.1 -C.sub.3 hydrocarbyl group; each R.sup.4 is independently hydrogen or a C.sub.1 -C.sub.10 hydrocarbyl group; and Y is a ##STR2## group wherein n=0 or 1.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: May 9, 1995
    Assignee: The Dow Chemical Company
    Inventors: Robert E. Hefner, Jr., Jimmy D. Earls
  • Patent number: 5412079
    Abstract: Disclosed is a liquid crystal monomer compound represented by formula (1): ##STR1## wherein n is an integer of from 2 to 18, X is direct bond, --(C.dbd.O)--O--, --(C.dbd.O)--NH-- or --N.dbd.N--, R.sup.1 is hydrogen or a lower alkyl group, and R.sup.2 is hydrogen, a cyano group or a methoxy group, as well as a liquid crystal polymer derived therefrom.
    Type: Grant
    Filed: March 25, 1994
    Date of Patent: May 2, 1995
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Junji Furukawa, Hiroshi Okamoto, Yoshio Onouchi, Takushi Andoh, Satoshi Urano
  • Patent number: 5380719
    Abstract: Angiotensin II inhibition is exhibited by ##STR1## wherein: X is --CH.sub.2 -- or O;R is hydrogen, alkyl, aryl, cycloalkyl, aralkyl, or cycloalkylalkyl;R.sup.1 and R.sup.2 are each independently O or absent;R.sup.3 is hydrogen, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, aralkyl, cycloalkylalkyl, halo, haloalkyl, or haloalkoxy;R.sup.4 is hydrogen, alkyl, alkenyl, alkoxy, aryl, cycloalkyl, aralkyl, cycloalkylalkyl, --R.sup.8 --OH, or --R.sup.8 CO.sub.2 R.sup.9 ;and the remaining symbols are as defined in the specification.
    Type: Grant
    Filed: April 28, 1992
    Date of Patent: January 10, 1995
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Kyoung S. Kim
  • Patent number: 5360924
    Abstract: Process for preparing aromatic olefins of the formula (1) ##STR1## in which R.sup.1 -R.sup.3 are hydrogen, alkyl (C.sub.1 -C.sub.8) , alkoxy-(C.sub.1 -C.sub.5), phenyl, fluorine, chlorine, bromine, --OH, --NO.sub.2, --CN, --CHO, --COalkyl(C.sub.1 -C.sub.4) , --COphenyl, --COOalkyl (C.sub.1 -C.sub.4) , --OCOalkyl(C.sub.1 -C.sub.4), --NHCOalkyl(C.sub.1 -C.sub.4) , --CF.sub.3, --NH.sub.2, --NH--alkyl(C.sub.1 -C.sub.4) or --N(alkyl(C.sub.1 -C.sub.4)).sub.2 and R.sup.4 is hydrogen, alkyl(C.sub.1 -C.sub.8), phenyl, fluorine, chlorine, bromine, --OH, --NO.sub.2, --CN, --CHO or --OCOalkyl (C.sub.1 -C.sub.4) , and X is, inter alia, alkenyl(C.sub.2 -C.sub.12) or cycloalkenyl(C.sub.4 -C.sub.8) or the group ##STR2## in which R.sup.5 and R.sup.6 are, independently of one another, hydrogen or methyl, and Y is --phenyl, --CN, --COOH, --COOalkyl(C.sub.1 -C.sub.12), --COOphenyl, ##STR3## --CON (phenyl).sub.2, --COalkyl(C.sub.1 -C.sub.12), --COphenyl, --Oalkyl(C.sub.1 -C.sub.12) , --Ophenyl or the radical ##STR4## in which R.
    Type: Grant
    Filed: January 6, 1994
    Date of Patent: November 1, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Matthias Beller, Hartmut Fischer, Heinz Strutz
  • Patent number: 5359126
    Abstract: Preparing cyclohexanediones of the formula ##STR1## an aldehyde is reacted with a ketene to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the cyclohexanedione give the productwherein:R is selected, e.g.
    Type: Grant
    Filed: February 7, 1994
    Date of Patent: October 25, 1994
    Assignee: Eastman Chemical Company
    Inventor: Charles A. McCombs
  • Patent number: 5326784
    Abstract: New cycloalkylalkylamines which are sigma-receptor ligands of formule (I) ##STR1## in which: R.sub.1 is H or lower alkyl; X and Y are H, OH, lower alkyl, lower alkoxy, halogen or nitrile; V.sub.1 and V.sub.2 together form a double bond attached to an oxygen atom or to a hydroxyimino radical, or are linked as an ethylenedioxy chain; A represents a valency bond, an oxygen atom, a methylene or an ethylene group; m is equal to 0, 1 or 2; n has the value of an integer from 1 to 5. Psychotropic drug which is also useful in gastroenterology.
    Type: Grant
    Filed: July 29, 1993
    Date of Patent: July 5, 1994
    Assignee: Institut de Recherche Jouveinal
    Inventors: Jean-Louis Junien, Alain Calvet, Henri Jacobelli, Francois Roman
  • Patent number: 5310760
    Abstract: Certain 3,4-disubstituted anilines and pharmaceutically acceptable salts thereof are provided which mimic IL-1 activity by inducing IL-2 synthesis and subsequent IL-2 receptor expression. Specifically, the invention provides compounds of Formula I and acid addition salts thereof: ##STR1## wherein Y is ##STR2## NHSO.sub.2 or SO.sub.2 NH where R.sup.4 is H; Z is --O--, --NH--, --NR--, --S--, or other heteroatoms capable of hydrogen bonding with R.sup.4 to give a preferred conformation;R is alkyl;R.sup.1 is --NH.sub.2 or --NHCH.sub.3 ;R.sup.2 is H, alkyl, cycloalkyl, aralkyl, substituted or unsubstituted aryl, or a substituted or unsubstituted nitrogen heterocyclic group having 4 to 5 nuclear carbon atoms; andR.sup.3 is a lipophilic moiety.
    Type: Grant
    Filed: July 9, 1993
    Date of Patent: May 10, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: William N. Washburn, Lee H. Latimer, Barbara B. Lussier, Carl R. Illig, Alexander L. Weis
  • Patent number: 5306695
    Abstract: Compounds of the formula I ##STR1## in which n is 0-6, R.sup.1 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, phenyl or halogenated phenyl,R.sup.2 is Hal, CN, alkyl, haloalkyl, alkoxy, haloalkoxy, thioalkyl, R.sup.a SO.sub.2 --, R.sup.a SO.sub.2 O--, R.sup.a SO.sub.2 NR.sup.6, R.sup.a and R.sup.b being alkyl or haloalkyl, and R.sup.3 is H, Hal, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio, and R.sup.4 is haloalkyl, are suitable as selective herbicides and as growth regulators. To prepare them, a cyclohexanedione can be reacted a) with a 4-oxy-substituted benzoyl chloride and the resulting enol ether can be rearranged, or b) with a benzoyl cyanide. The benzoyl chloride or benzoyl cyanide required can be obtained from correspondingly substituted toluenes via the carboxylic acid.
    Type: Grant
    Filed: March 4, 1992
    Date of Patent: April 26, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Herbert Stark, Klaus Bauer, Hermann Bieringer
  • Patent number: 5304573
    Abstract: The present invention relates to a hydrazone derivative represented by the general formula (I) shown below: ##STR1## wherein the substituents are as defined in the specification, processes for preparing the derivative, and uses of the derivative as an insecticide.The hydrazone derivative has a marked insecticidal effect on insect pests, especially against LEPIDOPTERA and COLEOPTERA.
    Type: Grant
    Filed: November 13, 1991
    Date of Patent: April 19, 1994
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Tomokazu Hino, Nobuharu Andoh, Hiroshi Hamaguchi, Atsushi Kanaoka
  • Patent number: 5304572
    Abstract: Novel N-acetonylbenzamides and their use in controlling phytopathogenic fungi.
    Type: Grant
    Filed: December 1, 1992
    Date of Patent: April 19, 1994
    Assignee: Rohm and Haas Company
    Inventors: Enrique L. Michelotti, David H. Young
  • Patent number: 5279764
    Abstract: The invention relates to dihalogenobenzene derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --(Z.sup.2 --A.sup.3).sub.n --R.sup.2wherein R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and n are as defined in the specification.
    Type: Grant
    Filed: November 23, 1992
    Date of Patent: January 18, 1994
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Georg Weber, Ulrich Finkenzeller, Andreas Wachtler, Thomas Geelhaar, David Coates, Ian C. Sage, Simon Greenfield
  • Patent number: 5260486
    Abstract: Herein is disclosed a process for producing a .beta.-ketoalcohol by the oxidative ring-opening reaction of a 1,3-dioxane derivative, said .beta.-ketoalcohol being able to be a substrate for asymmetric reaction.
    Type: Grant
    Filed: August 4, 1992
    Date of Patent: November 9, 1993
    Assignee: Ajinomoto Co., Inc.
    Inventors: Kazuhiro Watanabe, Eiji Nakanishi, Takayuki Suzuki, Kunisuke Izawa
  • Patent number: 5239084
    Abstract: Antimycotically-active compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are hydrogen, C.sub.1-7 -alkyl or C.sub.2-7 -alkenyl or together are a straight chain C.sub.2-4 -alkylene; R.sup.3 and R.sup.4 each independently are hydrogen or C.sub.1-7 -alkyl; R.sup.5 and R.sup.6 each independently are hydrogen, halogen, trifluoromethyl, nitro, cyano, C.sub.1-7 -alkoxy or C.sub.1-7 -alkyl; and Q is an unsubstituted or substituted phenyl or naphthyl group, wherein the substituents are at least one of halogen, trifluoromethyl, cyano, nitro, C.sub.1-7 -alkyl, C.sub.1-7 -alkoxy; C.sub.2-10 -alkenyl; or a substituted or unsubstituted C.sub.1-10 -alkyl group wherein said substituents are at least one hydroxy group; andpharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: September 10, 1992
    Date of Patent: August 24, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Philippe Guerry, Synese Jolidon
  • Patent number: 5236952
    Abstract: Catechol derivatives of the formula ##STR1## wherein Ra, Rb and Rc have the significance given herein, the ester and ether derivatives thereof which are hydrolyzable under physiological conditions and the pharmaceutically acceptable salts thereof are described and possess valuable pharmacological properties. In particular, they inhibit the enzyme catechol-O-methyltransferase (COMT), a soluble, magnesium-dependent enzyme which catalyses the transference of the methyl group of S-adensoylmethionine to a catechol substrate, whereby the corresponding methyl ethers are formed. Suitable substrates which can be O-methylated by COMT and which can thus be deactivated are, for example, extraneuornal catecholamines and exogeneously-administered therapeutically active substances having a catechol structure.Formula Ia above embraces not only compounds which form part of the invention, but also known compounds; the compounds which form part of the invention can be prepared according to known methods.
    Type: Grant
    Filed: April 16, 1991
    Date of Patent: August 17, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Karl Bernauer, Janos Borgulya, Hans Bruderer, Mose DaPrada, Gerhard Zurcher
  • Patent number: 5237099
    Abstract: The present invention relates to methods for controlling insect populations and for protecting living plants from insect attack by applying to said plants or to the soil in which they are growing an insecticidally-effective amount of a substituted benzoic acid 1 or 2-alkyl or 2-cycloalkylhydrazide.Novel substituted benzoic acid 1 and 2-alkyl and 2-cycloalkylhydrazides effective as insecticides or intermediates for the preparation of insecticidal diacylhydrazides also are presented.
    Type: Grant
    Filed: June 8, 1990
    Date of Patent: August 17, 1993
    Assignee: American Cyanamid Company
    Inventors: Roger W. Addor, David G. Kuhn, Donald P. Wright, Jr.
  • Patent number: 5229507
    Abstract: Compounds of the formula I ##STR1## in which R is the group --OC.sub.m H.sub.2mn R.sub.1 and M is two H or is Cu or Ni, R.sub.1 is --OH, --Cl, --Br, C.sub.1 -C.sub.30 alkoxy or --OC(O)R.sub.2, m is an integer from 2 to 6 and n is a number from 1 to 20, and R.sub.2 is C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl, cyclopentyl, cyclohexyl or C.sub.6 -C.sub.10 aryl or C.sub.6 -C.sub.10 arylmethyl which is unsubstituted or substituted by C.sub.1 -C.sub.18 alkyl.The compounds are dyes and IR absorbers and can be used for optical information storage systems employing diode lasers.
    Type: Grant
    Filed: November 16, 1990
    Date of Patent: July 20, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Marcus Baumann, Hanspeter Stricker, Walter Fischer, Jurgen Vogt, Jin Mizuguchi
  • Patent number: 5223529
    Abstract: Compounds of formula: ##STR1## in which R.sub.1 is (a) a phenyl radical or a substituted phenyl radical, (b) a chain --CH(R.sub.8)--COOR.sub.4, (c) a chain --CH.sub.2 --CO--NR.sub.5 R.sub.6 or (d) a phenylalkyl radical, R.sub.2 is a methylene or ethylene radical or a radical --CH(R.sub.7)--, R.sub.3 is a 1- or 2-naphthyl radical, 2- or 3-indolyl or phenylamino radical in which the phenyl ring is optionally substituted on the understanding that, when R.sub.3 is 1- or 2-naphthyl or 2- or 3-indolyl radical, R.sub.7 cannot represent a benzyl, alkylthioalkyl or phenyl radical, as well as, when R.sub.2 is a radical --CH(R.sub.7)--, their racemates and their stereoisomers, and medicinal products containing them.
    Type: Grant
    Filed: May 11, 1990
    Date of Patent: June 29, 1993
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Dominique Bourzat, Marc Capet, Claude Cotrel, Claude Guyon, Gerard Roussel, Franco Manfre
  • Patent number: 5220022
    Abstract: Disclosed are novel compounds of the formula ##STR1## wherein: R is ##STR2## where Ph is phenyl, or ##STR3## X is --NR.sub.5 R.sub.6 or --OR.sub.7 ; R.sub.1 and R.sub.2 are independently hydrogen, methyl, ethyl, cyclohexyl, ##STR4## butyl, or heptyl; R.sub.4 is o-phenylene or p-phenylene and R.sub.4 can be alkyl- halo- or alkoxy- substituted;R.sub.3 is hydrogen;R.sub.5, R.sub.6, and R.sub.7 are independently hydrogen, methyl, ethyl, tert-butyl, isobutyl, butyl, alkoxy, acyl, acylamino, aryl, amino, cyclohexyl, aminoalkyl and substituted or unsubstituted phenylamino;Y is sulfur and oxygen atom; and n is zero or 1; provided n=1 when Y is sulfur.
    Type: Grant
    Filed: January 28, 1991
    Date of Patent: June 15, 1993
    Assignee: International Paper Co.
    Inventors: Bruce M. Resnick, Allan J. Wexler