Halogen, Bonded Directly To Carbon, Containing Patents (Class 564/442)
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Patent number: 4613619Abstract: The invention concerns novel anti-arrhythmic amino-alcohol derivatives, characterized by the general formula (1) ##STR1## or pharmaceutically acceptable salts thereof, wherein R.sub.1, R.sub.2 and R.sub.3 each independently represent hydrogen, alkyl having 1-6 carbon atoms, alkoxy having 1-6 carbon atoms, acyloxy having 1-6 carbon atoms, hydroxy, halogen or optionally alkyl-substituted amino;R.sub.4 represents hydrogen, hydroxy or alkyl having 1-6 carbon atoms,R.sub.5 represents hydrogen or alkyl having 1-6 carbon atoms,R.sub.6 represents hydrogen, acyl having 1-18 carbon atoms or alkyl having 1-6 carbon atoms,R.sub.7 and R.sub.8 each independently represent hydrogen or alkyl having 1-6 carbon atoms,X represents a direct bond or an oxygen atom, andn and m each independently are integers having a value of 1 or 2, whereby the sum of n and m is 2 or 3.Type: GrantFiled: February 22, 1985Date of Patent: September 23, 1986Assignee: AKZO N.V.Inventors: Thomas Sleigh, David S. Savage, John K. Clark
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Patent number: 4604243Abstract: An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.Type: GrantFiled: July 25, 1985Date of Patent: August 5, 1986Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4599450Abstract: Acid nitro dyestuffs are prepared by treating aminonitrodiphenylaminesulfonic acids with an oxidizing agent in an aqueous medium, the oxidizing agent employed being a manganese-(VI) or manganese-(VII) compound and the reaction being carried out at a pH higher than 5 and at a temperature between 20.degree. and 100.degree. C. The dyestuffs thus obtainable dye even fresh full-grained chrome leather in full shades.Type: GrantFiled: May 10, 1984Date of Patent: July 8, 1986Assignee: Hoechst AktiengesellschaftInventor: Hasso Hertel
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Patent number: 4593101Abstract: 1,2,3,4-Tetrahydro-4-quinolinone of formula: ##STR1## are prepared from a 3-anilinopropionic acid of formula: ##STR2## which is treated successively with phosgene, phosgene in the presence of dimethylformamide, a Lewis acid or a strong acid, and a base. In the formula (I) and (II), R denotes a hydrogen atom, a halogen atom or an alkyl (1 to 4 carbon atoms) or alkoxy (1 to 4 carbon atoms) radical, and R.sub.1 denotes a hydrogen atom or an alkyl radical (1 to 4 carbon atoms). The compounds of formula I are useful as intermediates in the production of known drugs.Type: GrantFiled: September 20, 1984Date of Patent: June 3, 1986Assignee: Rhone-Poulenc SanteInventors: Michel Arnaud, Jean-Pierre Corbet
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Patent number: 4591359Abstract: Acid nitrodyestuffs are prepared by treating aminonitrodiphenylaminesulfonic acids with an oxidizing agent in an aqueous medium, the oxidizing agent being hypochlorous acid or its alkali metal or alkaline earth metal salts and the reaction taking place at above pH 4 and at a temperature between 0.degree. and 100.degree. C. The dyestuffs thus obtainable dye even fresh full chrome grained leather in deep shades.Type: GrantFiled: August 23, 1984Date of Patent: May 27, 1986Assignee: Hoechst AktiengesellschaftInventor: Hasso Hertel
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Patent number: 4582935Abstract: Disclosing a process for making meta-aminobenzotrifluoride comprising:reacting meta-nitrobenzotrichloride with hydrogen fluoride in the presence of ammonium ions under a pressure of at least about 35 psig and at a temperature of at least about 55.degree. C. for sufficient time in the presence of water and a metal catalyst to form meta-aminobenzotrifluoride, wherein the amount of water added is at least one mole percent of the meta-nitrobenzotrichloride.Type: GrantFiled: December 21, 1984Date of Patent: April 15, 1986Assignee: Olin CorporationInventor: Max M. Boudakian
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Patent number: 4558129Abstract: Novel compounds of the general formula: ##STR1## and the pharmaceutically acceptable esters and acid addition salts thereof, wherein:R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are each independently hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl; orR.sup.2 and R.sup.3 together form --OCH.sub.2 O--; andR.sup.10 and R.sup.11 are each independently hydrogen or lower alkyl.These compounds combine .beta.-blockade and calcium entry blockade properties in the same compound and therefore are useful in therapy in the treatment of cardiovascular diseases, including hypertension, arrhythmias and variant and exercise induced angina.Type: GrantFiled: May 18, 1983Date of Patent: December 10, 1985Assignee: Syntex (U.S.A.) Inc.Inventors: Arthur F. Kluge, Robin D. Clark, Arthur M. Strosberg
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Patent number: 4551264Abstract: New polyhalogenoaromatic compounds of Formula I ##STR1## wherein Y and Z are each independently alkyl, alkoxy or alkanoyl each of 1 to 12 C atoms, --COOR.sup.1, --O--CO--R.sup.1, CN, NO.sub.2, NH.sub.2 or OH;Q is one or two identical or different radicals selected from Ph, Cy, 1,4-bicyclo[2,2,2]octylene or 1,3-dioxane-2,5-diyl;X.sup.1 to X.sup.4 are each independently H, F, Cl or Br;R.sup.1 is alkyl of 1 to 4 C atoms, Ph--R.sup.2 or Cy--R.sup.2 ;R.sup.2 is alkyl or alkoxy each of 1-12 C atoms or CN;Ph is 1,4-phenylene; and Cy is 1,4-cyclohexylene,can be used as components of liquid-crystal dielectrics.Type: GrantFiled: March 14, 1983Date of Patent: November 5, 1985Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Michael Romer, Georg Weber
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Patent number: 4543426Abstract: A compound of the formula: ##STR1## where X and Y are independently chlorine or trifluoromethyl.Type: GrantFiled: January 9, 1984Date of Patent: September 24, 1985Assignee: GAF CorporationInventor: Kou-Chang Liu
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Patent number: 4543425Abstract: 1,3-diamino-4-(2',2',2'-trifluoroethoxy)-benzene, as well as its acid addition salts, are used as new compounds to serve as coupler substance in hair dyeing compositions and yields with known developer substances 1,4-diaminobenzene and 2,5-diaminobenzylalcohol to stable blue tones without any red fraction. Moreover, the new compounds lead to exceptional black tones and ash tones.Type: GrantFiled: August 5, 1983Date of Patent: September 24, 1985Assignee: Wella AGInventors: Eugen Konrad, Hans J. Braun, Herbert Mager, Friedrich Noser, Max Bracher
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Patent number: 4540522Abstract: This invention pertains to processes for the preparation of nuclear substituted benzylic halides such as ortho-amino benzyl chlorides by reaction of substituted benzyl sulfoxides with nonoxidizing acid halides.Type: GrantFiled: October 7, 1983Date of Patent: September 10, 1985Assignee: Monsanto CompanyInventors: John P. Chupp, Terry M. Balthazor
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Patent number: 4536341Abstract: Dihalo and haloalkyl, haloalkoxy or haloalkylthio-substituted anilines and aniline derivatives, e.g. isocyanates that are useful in the preparation of acyl ureas having insecticidal activity.Type: GrantFiled: August 3, 1983Date of Patent: August 20, 1985Assignee: The Dow Chemical CompanyInventors: Raymond H. Rigterink, Ronald J. Sbragia
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Substituted benzotrifluoride compounds as chemical intermediates and a process for their preparation
Patent number: 4532353Abstract: This invention pertains to two substituted benzotrifluoride compounds useful as chemical intermediates for a new class of 2-haloacetanilide herbicides and a process for making these intermediates. The process generally involves nitration and reduction of the corresponding benzotrifluoride compound.Type: GrantFiled: June 16, 1983Date of Patent: July 30, 1985Assignee: Monsanto Co.Inventors: John P. Chupp, Audrey Y. Ku, Thomas E. Neumann, Thomas E. Nickson -
Patent number: 4532352Abstract: A process is disclosed for the separation of p-fluoroaniline from a mixture, containing aniline and p-fluoroaniline, by contacting the mixture with a mineral acid in the presence of an organic solvent. The corresponding salt of p-fluoro-aniline is insoluble and can easily be isolated by conventional means such as filtration. If desired, the isolated salt can be converted to p-fluoroaniline by reaction with a base.Type: GrantFiled: October 24, 1983Date of Patent: July 30, 1985Assignee: Mallinckrodt, Inc.Inventor: Jerry R. Patton
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Patent number: 4521629Abstract: The invention relates to a method for the preparation of certain substituted bis-arylpentadienones which are useful and valuable intermediates for the preparation of insecticidal amidinohydrazones. The invention further relates to pentadienone substituted amidimohydrazone insecticides and fire ant control agents.Type: GrantFiled: June 29, 1984Date of Patent: June 4, 1985Assignee: American Cyanamid CompanyInventors: Nicholas A. Cortese, Jr., William H. Gastrock
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Patent number: 4518804Abstract: Novel N-aroyl N'-phenyl urea compounds having halogen substituents in the 2- and 5-position of the phenyl radical possess exceptional insecticidal activity.Type: GrantFiled: August 3, 1983Date of Patent: May 21, 1985Assignee: The Dow Chemical CompanyInventors: Raymond H. Rigterink, Barat Bisabri-Ershadi
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Patent number: 4503248Abstract: A class of polyamides comprising recurring units having substituted-quaterphenylene radicals is disclosed. The polymers comprise recurring units of the formula ##STR1## wherein each of A and B is a divalent radical, except that B can represent a single bond; R and R.sup.1 are each hydrogen, alkyl, aryl, alkaryl or aralkyl; and c is zero or one; and wherein, when c is one, at least one of A and B is a substituted-quaterphenylene radical having the formula ##STR2## where each U is a substituent other than hydrogen, each W is hydrogen or a substituent other than hydrogen, each p is an integer from 1 to 3, each X is hydrogen or a substituent other than hydrogen and each r is an integer from 1 to 4, the U, W.sub.p and X.sub.r substitution being sufficient to provide the radical with a non-coplanar molecular configuration; and wherein, when c is zero, A is a substituted-quaterphenylene radical as aforedescribed.Type: GrantFiled: May 27, 1983Date of Patent: March 5, 1985Assignee: Polaroid CorporationInventors: Russell A. Gaudiana, Palaiyur S. Kalyanaraman
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Patent number: 4491584Abstract: Certain compounds in which a carbon atom of a pyrrolidine or piperidine ring is bonded directly or through a methylene group to the nitrogen of a phenyl-substituted urea, and their pharmaceutically acceptable salts, are active antiarrhythmic agents.Type: GrantFiled: November 19, 1981Date of Patent: January 1, 1985Assignee: Riker LaboratoriesInventor: Elden H. Banitt
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Patent number: 4484940Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom and R is a C.sub.1 -C.sub.8 alkyl group except isopropyl, which is useful as a herbicide.Type: GrantFiled: March 23, 1982Date of Patent: November 27, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
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Patent number: 4484941Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom and R is a C.sub.3 -C.sub.4 alkenyl group or a C.sub.3 -C.sub.4 alkynyl group, which is useful as a herbicide.Type: GrantFiled: March 23, 1982Date of Patent: November 27, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
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Patent number: 4484008Abstract: This invention relates to an improvement in the process of isolating certain diphenyl ethers from an aprotic organic solvent by the addition of a diphenyl ether phase forming amount of water to a reaction mixture comprising a liquid phase of the diphenyl ether dissolved in the solvent.Type: GrantFiled: September 30, 1982Date of Patent: November 20, 1984Assignee: PPG Industries, Inc.Inventors: James A. Cook, Jr., James A. Manner
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Patent number: 4480140Abstract: Phenols alkylated in the ortho and/or para positions are produced in good yields and in the absence of isomers from phenolic compounds having at least two alkylateable ortho-ortho or ortho-para positions open. The phenolic compound is first partially chlorinated or brominated and the desired halogenated phenol having at least one open position ortho or para is reacted with an aldehyde having one to four carbon atoms and a secondary non-aromatic amine. The reaction is conducted in the liquid phase with a stoichiometric amount of the phenolic compound and stoichiometric or excess of stoichiometric amounts of the aldehyde and the amine. The reaction is performed at a temperature of from about 0.degree. C. to about 100.degree. C. to produce an aminoalkylated halogenated phenolic compound. This aminoalkylated halogenated phenolic compound is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 100.degree. C. to about 175.degree. C.Type: GrantFiled: March 16, 1983Date of Patent: October 30, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4475001Abstract: Ortho- or para-monoalkylated phenols or 2,4- or 2,6-dialkylphenols can be produced from phenolic compounds in good yields and in the absence of isomers. The starting phenol which has at least two available ortho or para positions unsubstituted is converted to a t-alkylated phenol having at least one ortho or para position unsubstituted. The desired t-alkylated phenolic compound is reacted with an aldehyde having one to four carbon atoms and a secondary aliphatic or alicyclic amine. The reaction is conducted in the liquid phase with a stoichiometric amount of the phenolic compound and stoichiometric or excess of stoichiometric amounts of the aldehyde and the secondary amine. The reaction is conducted at a temperature in the range of about 0.degree. C., to about 100.degree. C. and the reaction produces an aminoalkylated t-alkylated phenol. The aminoalkylated phenol is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 100.degree. C. to about 175.degree. C.Type: GrantFiled: March 17, 1983Date of Patent: October 2, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4456768Abstract: Prostaglandin and prostacyclin compounds which are fluorine substituted in any one or more of the following positions 4,4; 7,7; 10,10; and 5.Type: GrantFiled: May 1, 1981Date of Patent: June 26, 1984Assignee: The University of ChicagoInventor: Josef Fried
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Patent number: 4454350Abstract: A process for the acylation of halo- or trihalomethylbenzenes, wherein a halo- or trihalomethylbenzene is reacted with a carboxylic acid, a precursor or a derivative thereof in the presence of boron trifluoride in an amount such that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having a phytosanitary (e.g., herbicidal) or pharmaceutical activity.Type: GrantFiled: June 28, 1982Date of Patent: June 12, 1984Assignee: Rhone-Poulenc Specialities ChimiquesInventor: Michel Desbois
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Patent number: 4443449Abstract: Compounds of formula I ##STR1## in which R.sub.1 is H or C.sub.1-3 alkyl; R.sub.2 is H or C.sub.1-3 alkyl; R.sub.3 and/or R.sub.4 are H, C.sub.1-3 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-7 cycloalkyl or R.sub.3 and R.sub.4 together with the nitrogen atom form a heterocyclic ring system; R.sub.5 and/or R.sub.6 are H, halo, CF.sub.3, or C.sub.1-3 alkyl (with the proviso that R.sub.5 and R.sub.6 cannot both be H or methyl) or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring and R.sub.7 and/or R.sub.8 are H or C.sub.1-3 alkyl show therapeutic activity in the treatment of depression. Pharmaceutical compositions and processes for preparing compounds of formula I are disclosed.Type: GrantFiled: April 5, 1982Date of Patent: April 17, 1984Assignee: The Boots Company LimitedInventors: James E. Jeffery, Eric C. Wilmshurst
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Patent number: 4431671Abstract: Substituted N-(p-aminophenyl)-N'-benzoylureas of the formula ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl or propargyl; R.sub.2 and R.sub.3 are each hydrogen or halogen; R.sub.4 is methyl or halogen; and R.sub.5 is hydrogen or halogen. Processes for producing these compounds and their use for combating pests, particularly their use as insecticides, are described.Type: GrantFiled: December 3, 1981Date of Patent: February 14, 1984Assignee: Ciba-Geigy CorporationInventor: Josef Ehrenfreund
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Patent number: 4431822Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom, which is useful as a herbicide.Type: GrantFiled: March 23, 1982Date of Patent: February 14, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiromichi Oshio, Katsuzo Kamoshita
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Patent number: 4409386Abstract: An acid extraction process for separating 3,4-dichloroaniline from 2,3-dichloroaniline and 2,5-dichloroaniline is disclosed. The process involves selectively forming 3,4-dichloroaniline hydrochloride, since it has a higher basicity than the other dichloroaniline isomers, in a multiple stage extraction unit. An aqueous solution of 3,4-dichloroaniline hydrochloride is removed from the multiple stage extraction unit and neutralized with a base to form an immiscible mixture of an aqueous salt solution and 3,4-dichloroaniline which are separated by decantation.Type: GrantFiled: August 6, 1982Date of Patent: October 11, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: Tzu-Ching Chang
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Patent number: 4408043Abstract: Fluorinated compounds of the formula ##STR1## are disclosed. The cationic amine compounds are useful as surfactants.Type: GrantFiled: March 8, 1982Date of Patent: October 4, 1983Assignee: Nalco Chemical CompanyInventors: Virgil L. Seale, James R. Stanford, James E. Briscoe, Glenn S. Penny
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Patent number: 4405640Abstract: Insecticides of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each selected from methyl, halomethyl, and halo; X is oxygen, sulphur, sulphonyl or a group NR.sup.4 where R.sup.4 represents hydrogen, lower alkyl or lower carboxylic acyl; R.sup.3 is lower alkyl, lower alkenyl or benzyl; m has the value zero or one, and n has a value from one to four.Type: GrantFiled: December 1, 1980Date of Patent: September 20, 1983Assignee: Imperial Chemical Industries PLCInventor: Nazim Punja
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Patent number: 4404069Abstract: Various substituted ortho-alkyl anilines are prepared by electrolytic desulfurization of various benzyl sulfides, sulfoxides and sulfones, e.g. 2-methyl-6-trifluoromethylaniline is prepared from 2-amino-3-trifluoromethylbenzyl sulfides, sulfoxides and sulfones. The processes are conducted in concentrated aqueous quaternary ammonium hydroxide, as well as in aprotic media. The substituted anilines obtained are useful as intermediates for herbicide compounds.Type: GrantFiled: March 17, 1982Date of Patent: September 13, 1983Assignee: Monsanto CompanyInventors: Richard D. Goodin, John P. Chupp, Terry M. Balthazor, James P. Coleman
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Patent number: 4404402Abstract: There are provided novel substituted aniline intermediates, useful in the synthesis of certain substituted N-nitroanilines or salts thereof which may be used to elicit several desirable and advantageous biological responses in plants.Type: GrantFiled: March 4, 1982Date of Patent: September 13, 1983Assignee: American Cyanamid CompanyInventors: David W. Ladner, Barrington Cross
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Patent number: 4394521Abstract: Process for the production of 2,6-dichloro-5-hydroxy-anils having the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is an alkyl radical having 1 to 4 carbon atoms, by the conversion of 2,4-dichloro-3-aminophenol with a ketone. The reaction is conducted at a temperature of 0.degree. to 50.degree. C.Type: GrantFiled: April 28, 1981Date of Patent: July 19, 1983Assignee: Lonza-Werke G.m.b.H.Inventor: Reinhard Sappelt
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Patent number: 4380670Abstract: An aminobenzene is produced by reacting a chlorobenzene with ammonia in the presence of a copper type catalyst, namely by reacting ammonia with 3,5-diaminochlorobenzene to produce 1,3,5-triaminobenzene at a temperature of 150.degree. to 250.degree. C. at a molar ratio of ammonia of 2 to 10 to 3,5-diaminochlorobenzene in the presence of a copper compound catalyst.Type: GrantFiled: April 3, 1981Date of Patent: April 19, 1983Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Itaru Shigehara, Mikio Miyaji
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Patent number: 4377711Abstract: Disclosed are aromatic bromopolyfluoroalkyl ethers of the formula: ##STR1## where n is equal to 1 or 2 and R represents at least one moiety selected from the group consisting of hydrogen, the alkyl radicals having from 1 to 12 carbon atoms, the phenyl radical, the alkoxy radicals having from 1 to 12 carbon atoms, the phenyloxy radical, and the radicals NO.sub.2, CN, Cl, F, Br, I, CF.sub.3, and CONR.sub.1 R.sub.2 and NR.sub.1 R.sub.2 where R.sub.1 and R.sub.2 are identical or different and represent each a hydrogen or an alkyl radical having from 1 to 6 carbon atoms. Also disclosed is a method for preparation of these ethers. These compounds are useful as intermediates in producing products exhibiting phytosanitary or pharmaceutical activity.Type: GrantFiled: November 4, 1981Date of Patent: March 22, 1983Assignee: Rhone-Poulenc IndustriesInventors: Isabelle Rico, Claude Wakselman
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Patent number: 4365093Abstract: Novel ethynylbenzene compounds and their derivatives which are useful for the treatment for the relief of inflammation, pain and fever.Type: GrantFiled: November 23, 1976Date of Patent: December 21, 1982Assignee: William H. Rorer, Inc.Inventor: Julius Diamond
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Patent number: 4363766Abstract: A process for the preparation of sulfur-containing N-benzyl-amino acids of the formula ##STR1## wherein X and Y, which may be identical to or different from each other, are each hydrogen or halogen;R.sub.1 is hydrogen or alkyl of 1 to 4 carbon atoms;R.sub.2 is hydrogen, alkyl of 1 to 3 carbon atoms, carboxy-lower alkyl or acyl;R.sub.3 is hydrogen or acyl; andn is 1 or 2;which comprises the steps of converting anthranilic acid or a halogenated anthranilic acid into the corresponding aldehyde, reacting the aldehyde with a compound of the formula ##STR2## wherein R.sub.1, R.sub.2 and n have the meanings previously defined, to form the corresponding Schiff's base, reducing the said Schiff's base, and recovering the reaction product.Type: GrantFiled: April 17, 1979Date of Patent: December 14, 1982Assignee: Boehringer Ingelheim GmbHInventor: Bernard Bellegarde
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Patent number: 4343951Abstract: A process for the preparation of fluoroaniline compounds comprises the steps of(A) reacting an ammonium fluorophthalamate or a fluorophthalamic acid of the formula ##STR1## where n is 1 or 2 with an alkali or an alkali earth metal hypochlorite to form the corresponding fluoroanthranilic acid; and(B) decarboxylating the fluoroanthranilic acid by reaction with a mineral acid to form the corresponding fluoroaniline of the formula ##STR2## where n is as previously defined.Type: GrantFiled: December 29, 1980Date of Patent: August 10, 1982Assignee: Hooker Chemicals & Plastics Corp.Inventors: Michael J. Fifolt, Arthur M. Foster
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Patent number: 4335124Abstract: The compounds are 4-phenyl-4-lower alkyl-substituted-3-buten-2-ones, and -2-halo-1,3-butadienes, e.g., 2-(p-biphenylyl)-2-penten-4-one, and are useful as pharmaceuticals.Type: GrantFiled: October 14, 1980Date of Patent: June 15, 1982Assignee: Sandoz, Inc.Inventor: Eugene E. Galantay
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Patent number: 4333952Abstract: Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen, halogen or C.sub.1-4 alkoxy;X is oxygen; NR.sup.3 in which R.sup.3 is hydrogen, C.sub.1-4 alkyl, or -Y-R.sup.2 ; --C.dbd.O; or --CHOH;Y is --CH.sub.2 --CHOH, and when X is --C.dbd.O it may also be --CH.dbd.CH--; andR.sup.2 is C.sub.1-4 alkyl, one carbon atom of which is di- or tri-halogenated;or salts thereof, are useful in promoting growth of ruminants. Processes for their production, veterinary formulations and treatments are described.Type: GrantFiled: June 30, 1980Date of Patent: June 8, 1982Assignee: Beecham Group LimitedInventor: Brian G. McDonald
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Patent number: 4327018Abstract: New azo dyes are disclosed which are free from sulphonic acid groups and which are optionally quaternized in the coupling component, and mixtures of such dyes, which dyes correspond to the formula ##STR1## wherein X represents chlorine, optionally substituted phenyloxy, phenylmercapto, alkylmercapto, naphthyloxy, naphthylmercapto, or a heterocyclic radical which is bound by way of --O--, --NH-- or --S--, X.sub.1 represents hydrogen, cyano, lower alkoxy, carboxy, optionally branched and/or substituted alkyl having 1 to 12 carbon atoms, optionally branched and/or substituted lower alkenyl, optionally substituted cycloalkyl, aralkyl having 7 to 10 carbon atoms, aryl, carbamoyl, or a heterocyclic radical, W represents hydrogen, a cyano group, an optionally branched and/or substituted lower alkyl group, an optionally substituted cycloalkyl group, an aralkyl group (having 7 to 10 carbon atoms), an aryl group or the radicals ##STR2## wherein R.sub.1 and R.sub.2 represent lower alkyl, R.sub.Type: GrantFiled: September 17, 1979Date of Patent: April 27, 1982Assignee: Ciba-Geigy CorporationInventors: Hans W. Liechti, Kurt Burdeska, Jurgen Markert
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Patent number: 4327036Abstract: Process for nuclear chlorination of non-phenolic aromatic compounds, said process comprising contacting and reacting a non-phenolic aromatic compound having a net Hammett .sigma. value of about -0.1 to about 2.0 with chlorine monoxide in the presence of at least one-half an equivalent amount, based on the chlorine monoxide, of an acid having a pK.sub.a no greater than that of trichloroacetic acid, provided, however, when the net Hammett .sigma. value is about 0.7 to about 2.0, the acid has a pK.sub.a no greater than that of trifluoroacetic acid.Type: GrantFiled: May 8, 1980Date of Patent: April 27, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank D. Marsh
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Patent number: 4326077Abstract: Novel N-haloacetylphenylamino carbonyl oximes represented by the formula ##STR1## wherein Ar is phenyl or substituted phenyl; R.sup.1 is halomethyl; R.sup.2 and R.sup.3 are each independently hydrogen, alkyl, phenyl, benzyl, substituted phenyl or benzyl, haloalkyl, cyanoalkyl, alkoxyalkyl, alkylthioalkyl or thiocyanoalkyl; R.sup.4 is hydrogen or alkyl; n is 0 or 1; m is 0 or 1; R is hydrogen, alkyl, alkenyl, alkynyl, alkylthioalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, phenyl, benzyl, substituted phenyl or benzyl, or R is acyl of the formula ##STR2## wherein R.sup.5 is hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, acetonyl, or the group --NR'R" wherein R' and R" are independently hydrogen, alkyl or phenyl; with the proviso that R.sup.2 and R.sup.3 may be joined together to form a carbocyclic ring or a heterocyclic ring; or R and R.sup.2 may be joined together to form a heterocyclic ring; or R and R.sup.3 may be joined together to form a heterocyclic ring.Type: GrantFiled: September 22, 1980Date of Patent: April 20, 1982Assignee: Chevron Research CompanyInventors: William L. Schinski, David C. K. Chan, Irene C. Huang
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Patent number: 4310694Abstract: Novel substituted N-(p-aminophenyl)-N'-benzoyl ureas of the formula ##STR1## wherein each of R.sub.1 and R.sub.2 independently is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.5 alkenyl, each of R.sub.3 and R.sub.4 independently is chlorine or bromine, and each of R.sub.5 and R.sub.6 independently is hydrogen, fluorine or chlorine, with the proviso that R.sub.5 and R.sub.6 are not both simultaneously hydrogen, processes for the manufacture of these compounds and compositions containing them for use in pest control, especially for controlling insects harmful to plants and animals. The novel compounds inhibit feeding damage and have in particular a pronounced ovolarvicidal and ovicidal action against plant-destructive insects.Type: GrantFiled: January 14, 1981Date of Patent: January 12, 1982Assignee: Ciba-Geigy CorporationInventor: Josef Ehrenfreund
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Patent number: 4310693Abstract: o-Aminophenol derivatives are described represented by the formula (I) ##STR1## wherein R represents --NH.sub.2 or --NH--CO--R.sup.6 ; R.sup.1 and R.sup.2 which may be the same or different, each can represent an alkyl group or an aromatic group, or R.sup.1 and R.sup.2 together can form a ring; or R.sup.1, R.sup.2 and R.sup.3 together can form a ring ; R.sup.3 represents hydrogen, an alkyl group or an aromatic group; R.sup.4 can represent an alkyl group or an aromatic group; R.sup.5 can represent an alkyl group, an alkoxy group, an alkylthio group, an arylthio group, a halogen atom or an acylamino group; and n is 0, 1 or 2; R.sup.6 represents an alkyl group or an aromatic group; and R.sup.4 and R.sup.5 together can form a heterocyclic ring, R.sup.1 and R.sup.4 together can form a heterocyclic ring, or R.sup.1 and R.sup.5 together can form a ring; and R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5.sub.n have a total of 7 or more carbon atoms.Type: GrantFiled: July 18, 1980Date of Patent: January 12, 1982Assignee: Fuji Photo Film Co., Ltd.Inventors: Shinsaku Fujita, Koichi Koyama, Yoshio Inagaki
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Patent number: 4305959Abstract: This disclosure describes novel 4-(polyfluoroalkylamino)phenyl compounds useful as hypolipidemic and antiatherosclerotic agents.Type: GrantFiled: November 13, 1979Date of Patent: December 15, 1981Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4292239Abstract: Dyestuffs of the formula ##STR1## wherein R.sub.1 represents hydrogen, alkyl or aralkyl,R.sub.2 represents R.sub.1 or aryl,A represents C.sub.2 -C.sub.6 -alkylene,X represents R.sub.2 or acyl,n represents 1-7,m represents 1 or 2 andthe rings B and D can contain customary radicals,with the proviso that n is at least 2 if X represents acyl,give, when mixed with emulsifiers, dyestuff preparations which are in the liquid or dissolved form under dyeing conditions. The use of additional dispersing agents, protective colloids, levelling agents and carriers when dyeing polyester fibres thereby becomes superfluous.Type: GrantFiled: August 13, 1979Date of Patent: September 29, 1981Assignee: Bayer AktiengesellschaftInventors: Winfried Kruckenberg, Karl H. Schundehutte
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Patent number: 4288622Abstract: Diphenylamine of the formula ##STR1## wherein R.sub.1 and R.sub.4 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms, lower alkoxy having 1-6 carbon atoms, amino, lower alkyl amino wherein the alkyl moiety has 1-6 carbon atoms, acylamino, lower carbamylalkyl amino wherein the alkyl moiety has 1-6 carbon atoms, lower hydroxyalkyl amino wherein the alkyl moiety has 1-6 carbon atoms, lower carbalkoxy amino wherein the alkoxy moiety has 1-6 carbon atoms and ureido;R.sub.2 and R.sub.3 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms, lower alkoxy having 1-6 carbon atoms, acylamino and ureido;R.sub.5 and R.sub.8 each independently represent a member selected from the group consisting of hydrogen, halogen, lower alkyl having 1-6 carbon atoms and lower alkoxy having 1-6 carbon atoms; andR.sub.6 and R.sub.Type: GrantFiled: November 12, 1976Date of Patent: September 8, 1981Assignee: L'OrealInventors: Gregoire Kalopissis, Andree Bugaut, Francoise Estradier
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Patent number: 4268458Abstract: In a process for the preparation of an N-alkylated aromatic amine by contacting an aromatic amine with an aliphatic or cycloaliphatic alcohol at an elevated temperature and under increased pressure, in the presence of catalysts, the improvement wherein the reaction is carried out in the presence of a phosphorus oxyhalide.Type: GrantFiled: April 16, 1980Date of Patent: May 19, 1981Assignee: Bayer AktiengesellschaftInventors: Werner Schulte-Huermann, Heinz P. Hemmerich