Benzene Ring Containing Patents (Class 568/425)
  • Patent number: 4605758
    Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: August 12, 1986
    Assignee: Syntex Pharmaceuticals International Ltd.
    Inventor: George C. Schloemer
  • Patent number: 4578522
    Abstract: This invention relates to a method of synthesis of certain substituted carboxylic acids useful in lowering serum triglyceride and total cholesterol levels in mammals (including man) represented by the general formula I:Ar.sup.1 --Ar.sup.2 (I)whereinAr.sup.1 is selected from ##STR1## Ar.sup.2 is selected from ##STR2## and R is selected from C.sub.1-5 alkyl, halogen, perhalo-C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, C.sub.1-4 acyl, C.sub.1-6 alkoxycarbonyl, amino or hydroxy.
    Type: Grant
    Filed: September 14, 1984
    Date of Patent: March 25, 1986
    Inventor: John F. Eaddy, III
  • Patent number: 4532363
    Abstract: There is a method for the production of 3-phenylpyrrole derivatives having the general formula ##STR1## wherein X is halogen, nitro or haloalkyl having 1 to 3 carbon atoms;n is 0, 1 or 2; andZ is hydrogen or halogen;which comprises reacting a compound having the general formula ##STR2## wherein X and n are as previously defined; andY is hydrogen or halogen;with ammonia or aqueous ammonia in an organic solvent.A compound having the general formula [I] is useful as fungicide or intermediate thereof.
    Type: Grant
    Filed: May 30, 1984
    Date of Patent: July 30, 1985
    Assignee: Nippon Soda Company Limited
    Inventors: Akiyoshi Ueda, Humiko Nagasaki, Yutaka Takakura, Shigeru Kojima
  • Patent number: 4518415
    Abstract: Compounds useful as plant growth regulators and fungicides and having the formula ##STR1## and stereoisomers thereof, wherein W is --CH.dbd. or .dbd.N--; Q is optionally substituted aryl, especially optionally substituted phenyl, or optionally substituted aralkyl or alkyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, are H, optionally substituted alkyl, cycloalkyl, aralkyl or phenyl; R.sup.7 and R.sup.8 are H, alkyl or optionally substituted phenyl; and acid addition salts and metal complexes thereof, and processes and intermediates for their preparation.
    Type: Grant
    Filed: January 21, 1983
    Date of Patent: May 21, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony F. Marchington, Timothy Lewis, John M. Clough, Paul A. Worthington, John Dalziel
  • Patent number: 4490374
    Abstract: The synthesis of substituted quinazolinones is described. The novel quinazolinones are renal vasodilators and thereby increase renal blood flow, and are useful as cardiovascular agents.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: December 25, 1984
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Victor T. Bandurco, Seymour D. Levine, Dennis M. Mulvey, Alfonso J. Tobia
  • Patent number: 4486218
    Abstract: 1-Vinyltriazole compounds of the formula ##STR1## wherein R.sup.1 is alkyl, substituted alkyl, cycloalkyl, aryl or substituted aryl;R.sup.2 is alkyl;R.sup.3 is alkyl, cycloalkyl, cycloalkenyl, substituted cycloalkenyl, alkenyl, aryl or substituted aryl; orR.sup.2 and R.sup.3, together with the carbon to which they are bonded, represent cycloalkenyl, substituted cycloalkenyl, cycloalkyl or substituted cycloalkyl;X is the group ##STR2## or, alternatively, X may represent a keto group provided that when X is a keto group, R.sup.1 is alkyl, substituted alkyl, cycloalkyl, or substituted cycloalkyl;R.sup.4 is hydrogen, alkyl, aralkyl, substituted aralkyl, acyl, carbamoyl or substituted carbamoyl;R.sup.5 is hydrogen, alkyl, aralkyl or substituted aralkyl;and acid addition salts and metal salt complexes thereof; are outstandingly effective plant growth regulants and as fungicides.
    Type: Grant
    Filed: August 20, 1981
    Date of Patent: December 4, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolf Reiser, Wilfried Draber, Karl H. Buchel, Klaus Lurssen, Paul-Ernst Frohberger, Volker Paul
  • Patent number: 4486607
    Abstract: The invention relates to a process for the production of 3 (alkyl phenyl) propanals; certain of which are known to be valuable in the perfumery industry. The process enables this group of chemicals to be produced more easily as compared to known processes for their production. In a preferred embodiment in one step of the process the alkylation of the 3 phenyl propanol is carried out under controlled conditions so as to favor the production of para isomer of the product.
    Type: Grant
    Filed: July 12, 1982
    Date of Patent: December 4, 1984
    Assignee: Bush Boake Allen Limited
    Inventor: David Webb
  • Patent number: 4471126
    Abstract: There is a method for the production of 3-phenylpyrrole derivatives having the general formula ##STR1## wherein X is halogen, nitro or haloalkyl having 1 to 3 carbon atoms;n is 0, 1 or 2; andZ is hydrogen or halogen;which comprises reacting a compound having the general formula ##STR2## wherein X and n are as previously defined; andY is hydrogen or halogen;with ammonia or aqueous ammonia in an organic solvent.A compound having the general formula [I] is useful as fungicide or intermediate thereof.
    Type: Grant
    Filed: April 18, 1983
    Date of Patent: September 11, 1984
    Assignee: Nippon Soda Company Limited
    Inventors: Akiyoshi Ueda, Humihiko Nagasaki, Yutaka Takakura, Shigeru Kojima
  • Patent number: 4439620
    Abstract: The invention relates to 2,4-dichloro-r-fluorobenzoyl halide (particularly the chloride) and methods for its production. Also included in the invention are intermediates useful for the production of said 2,4-dichloro-5-fluorobenzoyl halide (particularly the chloride).
    Type: Grant
    Filed: July 14, 1982
    Date of Patent: March 27, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Klauke, Klaus Grohe
  • Patent number: 4436662
    Abstract: The present invention relates to compounds of the formula ##STR1## wherein R.sub.1 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, hydroxy, lower alkoxy or acyloxy and R.sub.2 and R.sub.4 are hydrogen or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 taken together are oxo groups with the proviso that at least one oxo group is present; R is selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids and the esters and amides thereof, hydroxy C.sub.2 to C.sub.7 alkyl and amino C.sub.2 to C.sub.7 alkyl or mono- or di-lower alkyl amino C.sub.2 to C.sub.7 alkyl; R.sub.5 is halogen or hydrogen; and R.sub.6 is halogen with the proviso that when R.sub.1 or R.sub.3 is hydroxy, lower alkoxy or acyloxy, then R is lower alkyl or hydrogen and the N-oxides and the pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: March 31, 1983
    Date of Patent: March 13, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4435585
    Abstract: There is disclosed a novel process for preparing a number of cinnamaldehyde derivatives. These cinnamaldehyde derivatives can be reduced to dihydrocinnamaldehyde derivatives, a number of which are commercially important in the preparation of fragrances. The invention is also directed to a number of novel intermediates and their preparation.
    Type: Grant
    Filed: November 17, 1981
    Date of Patent: March 6, 1984
    Assignee: Givaudan Corporation
    Inventors: Yvo Crameri, Paul A. Ochsner, Peter Schudel
  • Patent number: 4395575
    Abstract: 9-Substituted, 4- or 6-fluorine substituted retinoic acid derivatives useful as antitumor agents and in the treatment of acne as well as a method for their manufacture are disclosed. Substituents at the 9-position include substituted phenyl, thienyl and furyl groups.
    Type: Grant
    Filed: March 3, 1982
    Date of Patent: July 26, 1983
    Assignee: Hoffmann-La Roche, Inc.
    Inventors: Ka-Kong Chan, Beverly A. Pawson
  • Patent number: 4379765
    Abstract: There are presented compounds of the formulas ##STR1## wherein R.sub.1 is hydrogen or lower alkyl; R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids, hydroxy C.sub.2 to C.sub.7 alkyl, C.sub.2 to C.sub.7 carboxylic acid esters and amides and the group COR.sub.11 wherein R.sub.11 is alkoxy, amino or mono- lower alkyl amino; R.sub.6 is nitro or halo and R.sub.5 is hydrogen or halo,and the pharmaceutically acceptable salts thereof.The pyrazolobenzazepines are useful as anxiolytic and sedative agents.Also provided are processes and intermediates in the production of the above pyrazolobenzazepines.
    Type: Grant
    Filed: July 23, 1981
    Date of Patent: April 12, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George F. Field, Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
  • Patent number: 4371547
    Abstract: 2-Benzylideneglutaraldehydes of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or a substituent selected from the group consisting of halo, lower-alkyl, phenyl, carboxy, lower-alkoxycarbonyl, phenoxycarbonyl, aminocarbonyl, hydroxysulfonyl, nitro, cyano, hydroxy, lower-alkoxy and phenoxy, a method of use thereof as disinfectants, disinfectant compositions comprising them, and 2,6-dialkoxy-3-(.alpha.-alkoxybenzyl)tetrahydropyrans of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are as defined above and R.sup.4 and R.sup.5 independently are alkyl of one to four carbon atoms, which are intermediates for their preparation are disclosed.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: February 1, 1983
    Assignee: Sterling Drug Inc.
    Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
  • Patent number: 4335136
    Abstract: 4,5-Diaryl-.alpha.-(polyfluoroalkyl)-1H-pyrrole-2-methanamines such as 4,5-bis(4-fluorophenyl)-.alpha..alpha.-bis-(trifluoromethyl)-1H-pyrrole-2- methanamine, useful in treatment of inflammation.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: June 15, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Saul C. Cherkofsky
  • Patent number: 4326055
    Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: April 20, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter Loeliger
  • Patent number: 4322563
    Abstract: Substituted biphenyl-2-carboxaldehydes are prepared in good yield by reacting palladium complexes of substituted benzaldehyde aniline Schiff bases with substituted phenylmagnesium bromides in the presence of at least six, preferably eight, molar equivalents of triphenylphosphine.
    Type: Grant
    Filed: February 11, 1981
    Date of Patent: March 30, 1982
    Assignee: Merck & Co., Inc.
    Inventor: William F. Hoffman
  • Patent number: 4315764
    Abstract: 1-Allyl-triazole derivatives of the formula ##STR1## in which R represents hydrogen, alkyl or optionally substituted aralkyl,R.sup.1 represents optionally substituted alkyl, cycloalkyl or optionally substituted aryl,R.sup.2 represents alkyl andR.sup.3 represents alkyl, cycloalkyl, optionally substituted cycloalkenyl, alkenyl or optionally substituted aryl, orR.sup.2 and R.sup.3, together with the carbon atom to which they are bonded, represent optionally substituted cycloalkenyl or cycloalkylX represent the group ##STR2## or the keto group, R.sup.4 represents hydrogen, alkyl, optionally substituted aralkyl, acyl or optionally substituted carbamoyl andR.sup.5 represents hydrogen, alkyl or optionally substituted aralkyl,or acid addition salts or metal salt complexes thereof are characterized by fungicidal and plant growth regulatory activity.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: February 16, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolf Reiser, Wilfried Draber, Karl H. Buchel, Klaus Lurssen, Paul-Ernst Frohberger, Volker Paul
  • Patent number: 4285777
    Abstract: A process for purification of impure benzaldehyde by which purified benzaldehyde is prepared which has improved color stability and improved olfactory characteristics. The process is comprised of the steps of treatment with hydrogen in the presence of a hydrogenation catalyst followed by distillation.The present invention is a new and novel process for the purification of benzaldehyde and, is in particular, a unique and novel process for the purification of benzaldehyde prepared by the oxidation of toluene with a gas containing molecular oxygen.
    Type: Grant
    Filed: February 28, 1980
    Date of Patent: August 25, 1981
    Assignee: Stamicarbon, B.V.
    Inventor: Cornelis Jongsma
  • Patent number: 4283569
    Abstract: Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 -C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.
    Type: Grant
    Filed: September 13, 1977
    Date of Patent: August 11, 1981
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4282251
    Abstract: Cinnamylalkyl-1-naphthylmethylamines, useful as antimycotic agents, and processes for their production.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: August 4, 1981
    Assignee: Sandoz Ltd.
    Inventor: Daniel Berney
  • Patent number: 4273940
    Abstract: It has been found that bis(2-benzylaminoethyl)-disulfides with the phenyl rings carrying various simple substituents, are highly effective anti-inflammatories and inhibit chemotaxis of human neutrophils.
    Type: Grant
    Filed: May 13, 1980
    Date of Patent: June 16, 1981
    Assignee: Abbott Laboratories
    Inventors: Fortuna Haviv, George W. Carter
  • Patent number: 4256641
    Abstract: The preparation of racemic and optically pure tryptophans is described. The D-enantiomers of the 6-substituted compounds possess a potent sweetening capability. Novel intermediates are also disclosed.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: March 17, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Andrew D. Batcho, Urs O. Hengartner, Willy Leimgruber, John W. Scott, Donald Valentine, Jr.
  • Patent number: 4252738
    Abstract: 1,2-Halohydrincarboxylic acid esters of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are identical or different and represent hydrogen, cyano and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxycarbonyl, acyloxy, alkoxy and aryloxy, and furthermoreR.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, or R.sup.1 and R.sup.3 and/or R.sup.2 and R.sup.4 can be linked, forming a ring with the carbon atoms to which they are bonded;R.sup.5 represents hydrogen and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxy and alkoxycarbonyl andX represents fluorine, chlorine, bromine and iodine; a process for preparing such 1,2-halohydrincarboxylic acid esters by reacting a cyclobutane-cis-1,2-diol of the formula ##STR2## with an orthoester of the formula ##STR3## wherein R.sup.1 -R.sup.5 have the previously ascribed significance and R.sup.6 -R.sup.
    Type: Grant
    Filed: March 17, 1978
    Date of Patent: February 24, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Willy Hartmann, Hans-Georg Heine
  • Patent number: 4247717
    Abstract: New organo-selenenyl aldehyde of formula C.sub.6 H.sub.5 -Se-CH.sub.2 -CHO and method for its preparation.The new compound is a useful starting material for the preparation of allylic alcohols, epoxydes or olefines.
    Type: Grant
    Filed: September 7, 1979
    Date of Patent: January 27, 1981
    Assignee: Firmenich SA
    Inventor: Martin Petrzilka
  • Patent number: 4219489
    Abstract: Method and compounds are provided for use in the synthesis of steroids wherein a polyolefin is provided having an initiating group having a chalcogen atom in juxtaposition to a double bond, so as to be capable of bond formation to close to form a ring and having a terminating group involving pi unsaturation (a double or triple bond) conjugated to an aromatic ring. Upon acid catalysis, sigma bonds are formed through the interaction of a carbocation formed at the carbon atom bonded to the chalcogen atom and the double bond intermediate the initiating group and the terminating group, which close to form rings of a steroid nucleus, the carbocation interacting with the pi unsaturation conjugated with the aromatic group and being captured by a nucleophile present in the acidic reaction medium. The resulting steroid product may then be modified in known ways to produce known steroids.
    Type: Grant
    Filed: September 5, 1978
    Date of Patent: August 26, 1980
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: William S. Johnson, Leonard A. Bunes
  • Patent number: 4215044
    Abstract: Process for preparing an organic compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3, which process comprises contacting and reacting in a reaction mixture which includes an inert solvent, at a temperature of -40.degree. C. to -100.degree. C., ROF and ##STR1## R is polyfluoroperhaloalkyl of 1-6 carbon atoms or FOCF.sub.2 ; R.sup.1 is hydrocarbyl of 1-6 carbon atoms;each R.sup.2 is selected from H, alkyl of 1-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, aryl, heteroaryl and such alkyl, cycloalkyl, aryl and heteroaryl substituted by halogen or alkoxy of 1-6 carbon atoms;R.sup.3 is selected from H, alkyl and haloalkyl of 1-16 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl and haloaryl, OSi(R.sup.1).sub.3, OH, NH.sub.2, alkoxy of 1-6 carbon atoms, aryloxy, NHR.sup.1 and NR.sup.1.sub.2 wherein R.sup.1 is alkyl of 1-6 carbon atoms, N-arylamino and nitrogen or sulfur heterocyclic of 4-5 carbon atoms;R.sup.3 and one R.sup.2 taken together is a diradical which with the C.dbd.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: July 29, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William J. Middleton
  • Patent number: 4202822
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: May 13, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner