Benzene Ring In A Substituent E Patents (Class 564/218)
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Patent number: 4872902Abstract: The invention relates to the novel cyclohexanediones of formula I ##STR1## in which R is hydrogen or C.sub.1 -C.sub.6 -alkyl,A is R.sub.2, OR.sub.3 or NR.sub.3 R.sub.4,R.sub.2 is C.sub.1 -C.sub.6 -alkyl that is unsubstituted or is mono-substituted by C.sub.1 -C.sub.4 -alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, or is phenyl or benzyl each of which is unsubstituted or is mono-, di- or tri-substituted by R.sub.5,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 and R.sub.4 are, in addition, together with the nitrogen atom to which they are bonded, a pyrrolidine, morpholine or piperidine radical,B is one of the radicals ##STR2## m is 0, 1, 2 or 3, R.sub.5 is halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.Type: GrantFiled: February 8, 1988Date of Patent: October 10, 1989Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4873338Abstract: Compounds corresponding to Formula I ##STR1## wherein R.sup.1 denotes an acyl group andX denotes hydrogen, halogen, alkoxy, aroxy, SO.sub.3 H or a heterocyclic group attached through --O-- or --N<are prepared form a compound corresponding to Formula II ##STR2## wherein X has the meaning already indicated and Q denotes the group required for completing a dicarbonimide ringby reduction of the said compound to the amino compound and acylation into a compound corresponding to Formula III ##STR3## wherein X, Q and R.sup.1 have the meanings indicatedfollowed by conversion of the compound corresponding to Formula III into a compound corresponding to Formula I by hydrazinolytic or hydrolytic decomposition of the dicarbonimide ring.Type: GrantFiled: November 23, 1987Date of Patent: October 10, 1989Assignee: Agfa-Gevaert AktiengesellschaftInventors: Heinz Wiesen, Erich Wolff
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Patent number: 4871858Abstract: An amine is reached with dimethyformamioe in the presence of a solid catalyst to produce a formamide corresponding to the amine. The solid catalyst includes an oxide of metals belonging to Groups III, IV and V of the Periodic Table.Type: GrantFiled: December 7, 1987Date of Patent: October 3, 1989Assignee: Japan Tobacco Inc.Inventors: Hajime Matsushita, Makoto Shibagaki, Kyoko Takahashi
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Patent number: 4855498Abstract: Disclosed are platinum (IV) chelates derived from substituted amides. The chelates result from the reaction under mild conditions of potassium chloroplatinate (II) and the appropriate amide. The chelate transdichloro-cis-bis(dimethylacetamide-C,O) was prepared, fully characterized and exemplified in preparation of the antihistamine diphenhydramine hydrochloride.Type: GrantFiled: February 22, 1988Date of Patent: August 8, 1989Assignee: University of DelawareInventors: Rosette M. Roat, Seymour Yolles
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Patent number: 4835272Abstract: A process for formation of a base, which comprises reacting an acetylide compound with a salt. The acetylide compound has the following formula:(R--C.tbd.C--).sub.n Mwherein R is a monovalent group selected from the group consisting of an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aralkyl group, an aryl group and a heterocyclic group, each of which may have one or more substituent groups; M is an n-valent transition metal atom; and n is 1, 2 or 3. The salt is composed of an anion having an affinity for the transition metal (M) (the affinity of the anion for the transition metal is more than that of the acetylide anion (R--C.tbd.C.crclbar.)), and a cation derived from one selected from the group consisting of an alkali metal, an alkaline earth metal, ammonia and an organic base. A light-sensitive material containing the acetylide compound and the salt is also disclosed.Type: GrantFiled: July 16, 1987Date of Patent: May 30, 1989Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Shunichi Ishikawa, Ken Kawata
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Patent number: 4826982Abstract: Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen atom or lower alkyl group; the hydrates or the pharmaceutically acceptable acid addition or alkali salts thereof are useful as an antibacterial agent.Type: GrantFiled: September 2, 1986Date of Patent: May 2, 1989Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Kuniyoshi Masuzawa, Seigo Suzue, Keiji Hirai, Takayoshi Ishizaki
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Patent number: 4801408Abstract: 3-Amino-4-fluoro-6-halophenylthioacetic acids of the formula: ##STR1## and 5-substituted acetanilides of the formula: ##STR2## which are intermediary compounds for the synthesis of herbicidally effective 2-substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones of the formula: ##STR3## through the corresponding acid of the formula: ##STR4## (wherein X is a chlorine atom or a bromine atom, R is a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a C.sub.3 -C.sub.6 alkenyl group, a C.sub.3 -C.sub.6 alkynyl group, a C.sub.2 -C.sub.6 haloalkyl group, a C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.4)alkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl group or a phenyl group and Z is --NO.sub.2, --NH.sub.2, --SCH.sub.2 COOH, --SO.sub.2 Cl, --SO.sub.3 H or --SH).Type: GrantFiled: June 25, 1987Date of Patent: January 31, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Eiki Nagano, Ryo Yoshida, Hiroshi Matsumoto, Shunichi Hashimoto, Katsuzo Kamoshita
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Patent number: 4778911Abstract: A process for the preparation of 3-(acyl)amino-4-alkoxy-phenyl-.beta.-hydroxyethyl-sulfone (sulfates) of the formula (1) ##STR1## in which R.sub.1 is alkyl having 1-4 carbon atoms and R.sub.2 is hydrogen or one of the groupings ##STR2## with the proviso that n=1 if R.sub.2 =H and n=0 if R.sub.2 =acyl, by converting 2-alkoxyacylanilines of the formula (2) ##STR3## in which R.sub.1 and R.sub.2 have the meanings given, in a known manner to the corresponding sulfochlorides substituted in the p-position relative to the alkoxy group, reducing the sulfochlorides with an alkali metal sulfite or ammonium sulfite in an aqueous medium at pH 7.0-8.5 and at -5 to +40.degree. C. to give the corresponding sulfinates, alkoxylating the latter with ethylene oxide in an aqueous medium at pH 6.0-8.5 and 40.degree.-80.degree. C. to give the 3-acylamino-4-alkoxyphenyl-.beta.-hydroxyethyl-sulfones of the formula (1) (with R.sub.Type: GrantFiled: June 18, 1987Date of Patent: October 18, 1988Assignee: Hoechst AktiengesellschaftInventors: Peter Hess, Folker Kohlhaas, Theodor Papenfuhs
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Patent number: 4766243Abstract: A process for the electrophilic ring fluorination of aromatic compounds which comprises reacting a fluorinating agent from the group consisting of CF.sub.3 OF and CF.sub.2 (OF).sub.2 with an aromatic compound of the formula ##STR1## where X is selected from the group consisting of ##STR2## and ##STR3## and Y is selected from the group consisting of --H, --CF.sub.3, --CN, --NO.sub.2, --Cl, and CH.sub.3.Type: GrantFiled: August 10, 1984Date of Patent: August 23, 1988Assignee: Occidental Chemical CorporationInventor: Michael J. Fifolt
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Patent number: 4760183Abstract: A process for the preparation of aromatic dialkylamines of the formula (1) ##STR1## in which R denotes an alkyl-C.sub.1 -C.sub.6 group, X and Y each denote a hydrogen, fluorine or chlorine atom or a hydroxyl, alkyl-C.sub.1 -C.sub.4, alkoxy-C.sub.1 -C.sub.4, carboxyl, carbalkoxy-C.sub.1 -C.sub.5, alkyl-C.sub.1 -C.sub.4 --CO--NH--, ##STR2## sulfonic acid, alkyl-C.sub.1 -C.sub.4 sulfonate, sulfamoyl, alkyl-C.sub.1 -C.sub.4 -sulfonyl, hydroxy-alkylene-C.sub.1 -C.sub.4 -sulfonyl, phenylsulfonyl, hydroxyphenylsulfonyl, alkyl-C.sub.1 -C.sub.4 -phenylsulfonyl or alkoxy-C.sub.1 -C.sub.4 -phenylsulfonyl group, wherein compounds of the formula (2) ##STR3## in which R.sub.Type: GrantFiled: August 5, 1986Date of Patent: July 26, 1988Assignee: Hoechst AktiengesellschaftInventors: Theodor Papenfuhs, Walter Kuhn
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Patent number: 4752615Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole, thiophanate and/or cyclic imide fungicides.Type: GrantFiled: November 13, 1986Date of Patent: June 21, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Toshiro Kato, Hiroshi Noguchi, Yukio Oguri, Shigeo Yamamoto, Katsuzo Kamoshita
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Patent number: 4749812Abstract: An N-(3-chloro-4-isopropylphenyl)carboxamide derivative represented by the general formula ##STR1## wherein R represents a 1-methylbutyl, 1-methylcyclopropyl or cyclopropyl group. This derivative is useful as a selective herbicide, and can be produced by reacting 3-chloro-4-isopropylaniline with a carboxylic acid halide derivative of the general formula ##STR2## wherein R is as defined above and X represents halogen, or with a carboxyilc acid anhydride of the general formula ##STR3## wherein R is as defined above.Type: GrantFiled: May 21, 1986Date of Patent: June 7, 1988Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tetsuo Takematsu, Mitihihiko Nakaya, Koichi Moriyasu
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Patent number: 4745219Abstract: This invention pertains to chemical intermediates for a new class of 2-haloacetanilide herbicides and a process for preparation of these intermediates. The process generally involves nitration of substituted benzotrifluoride compounds.Type: GrantFiled: August 8, 1986Date of Patent: May 17, 1988Assignee: Monsanto CompanyInventors: Thomas E. Nickson, John P. Chupp, Thomas E. Neumann
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Patent number: 4709049Abstract: 3-Amino-4-fluoro-6-halophenylthioacetic acids of the formula: ##STR1## and 5-substituted acetanilides of the formula: ##STR2## , which are intermediary compounds for the synthesis of herbicidally effective 2-substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones of the formula: ##STR3## through the corresponding acid of the formula: ##STR4## (wherein X is a chlorine atom or a bromine atom, R is a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a C.sub.3 -C.sub.6 alkenyl group, a C.sub.3 -C.sub.6 alkynyl group, a C.sub.2 -C.sub.6 haloalkyl group, a C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.4)alkyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl group or a phenyl group and Z is --NO.sub.2, --NH.sub.2, --SCH.sub.2 COOH, --SO.sub.2 Cl, --SO.sub.3 H or --SH).Type: GrantFiled: June 17, 1985Date of Patent: November 24, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Eiki Nagano, Ryo Yoshida, Hiroshi Matsumoto, Shunichi Hashimoto, Katsuzo Kamoshita
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Patent number: 4677228Abstract: This invention relates to a Friedel-Crafts acylation process using trichlorobenzene as solvent.Type: GrantFiled: February 7, 1986Date of Patent: June 30, 1987Assignee: Smith Kline & French Laboratories, Ltd.Inventor: Brian M. Adger
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Patent number: 4661632Abstract: Halogenopropargylformamides of the formula ##STR1## in which R is hydrogen, alkyl, halogenoalkyl, cycloalkyl, halogenoalkyl, cycloalkyl, alkenyl, alkinyl, halogenoalkinyl, optionally substituted aralkyl and optionally substituted aryl, andHal is halogen.which possess fungicidal and bactericidal properties.Type: GrantFiled: October 31, 1985Date of Patent: April 28, 1987Assignee: Bayer AktiengesellschaftInventors: Siegfried Oeckl, Paul Reinecke, Wilhelm Brandes, Karl-Heinz Kuck, Wilfried Paulus, Hermann Genth
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Patent number: 4652633Abstract: Compounds useful for dyeing nylon, wool, and leather, having the formula: ##STR1## wherein X.sup.1 is chlorine, bromine, methyl or trifluoromethyl, Y.sup.3 is chlorine or bromine, and K.sup.1 is a radical of the formula ##STR2## where R.sup.3 is C.sub.2 to C.sub.4 hydroxyalkyl, methoxyethyl or methoxypropyl.Type: GrantFiled: February 15, 1985Date of Patent: March 24, 1987Assignee: BASF AktiengesellschaftInventor: Gunther Lamm
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Patent number: 4600797Abstract: Process for the preparation of a nitroaminobenzene by nitrating an aminobenzene which is protected at the nitrogen wherein the nitration is carried out by the simultaneous combination of nitric acid and the aminobenzene to be nitrated, in the presence of inert solvents such as methylene chloride.Type: GrantFiled: February 18, 1983Date of Patent: July 15, 1986Assignee: Bayer AktiengesellschaftInventor: Willi Schossler
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Patent number: 4590281Abstract: Provided is a process for preparing an aldehyde or aldehydes represented by the following formula (III), characterized in that a diaryliodonium salt represented by the following formula (I) is reacted with an unsaturated alcohol represented by the following formula (II) in a solvent containing a base in the presence of a transition metal catalyst at a temperature in the range of room temperature to 100.degree. C.:[Ar.sub.1 --I.sup..sym. --Ar.sub.2 ] X.sup..crclbar. (I)CHR.sub.1 .dbd.CR.sub.2 --CH.sub.2 OH (II)Ar.sub.3 --CHR.sub.1 --CHR.sub.2 --CHO (III)wherein Ar.sub.1 and Ar.sub.2, which may be alike or different, are each an aryl group which may have a substituent group or groups, X.sup..crclbar. is a counter ion which is inert to the above reaction, Ar.sub.3 is the same aryl group as Ar.sub.1 or Ar.sub.2, and R.sub.1 and R.sub.2 are each hydrogen atom or an alkyl group of C.sub.1 to C.sub.12.Type: GrantFiled: March 7, 1984Date of Patent: May 20, 1986Assignee: Nippon Petrochemicals CompanyInventors: Yasuo Yamazaki, Takehiko Suzuki
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Patent number: 4567198Abstract: Novel analgesic and enkephalinase inhibiting compositions comprising an analgesically and enkephalinase inhibitory effective amount of at least one compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and acetyl, n is 1 or 2 and when n is 1, R.sub.2 is selected from the group consisting of phenyl, p-chlorophenyl, m-trifluoromethylphenyl and thiazolyl and when n is 2, R.sub.2 is selected from the group consisting of phenyl and p-chlorophenyl and their salts with non-toxic, pharmaceutically acceptable acids and bases and an inert pharmaceutical carrier and novel method of relieving pain and inhibiting enkephalinase activity in warm-blooded animals and novel amides.Type: GrantFiled: February 6, 1984Date of Patent: January 28, 1986Assignee: Roussel UclafInventors: Francoise Delevallee, Roger Deraedt, Odile Le Martret
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Patent number: 4556737Abstract: This invention provides novel sulfonium compounds, processes for the preparation of the sulfonium compounds, and pharmacological composition containing the sulfonium compound. The compounds of this invention are useful for treating allergy.Type: GrantFiled: February 27, 1984Date of Patent: December 3, 1985Assignee: Taiho Pharmaceutical Company LimitedInventors: Akihide Koda, Mikio Hori, Naosuke Matsuura, Mitsugi Yasumoto, Ichiro Yamawaki, Shuichi Ueda, Yukio Tada
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Patent number: 4552981Abstract: The present invention is directed to a process for preparing 5-nitro-acet-2,4-xylidine comprising:(a) dissolving acet-2,4-xylidine in an aqueous sulfuric acid solution, said aqueous solution containing from 86 to 92% by weight of sulfuric acid, the weight ratio of sulfuric acid to acet-2,4-xylidine being from 3.5:1 to 6.5:1;(b) nitrating the resultant solution at a temperature of from 0.degree. to 15.degree. C. in a mixed acid containing nitric acid, sulfuric acid, and from 10 to 25% by weight water; and(c) recovering 5-nitro-acet-2,4-xylidine.Type: GrantFiled: November 27, 1981Date of Patent: November 12, 1985Assignee: Mobay Chemical CorporationInventors: Karl W. Thiem, Daniel P. Vanderpool
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Patent number: 4545995Abstract: The novel unsaturated arylalkyl ammonium salts described herein are useful as antiarrhythmic agents. A method of treating arrhythmia by increasing the refractoriness of cardiac tissue is provided, as well as pharmaceutical formulations containing such ammonium salts.Type: GrantFiled: July 12, 1983Date of Patent: October 8, 1985Assignee: Schering A.G.Inventors: William C. Lumma, Jr., Ronald A. Wohl
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Patent number: 4545996Abstract: The present invention relates, by way of new industrial products, to the N-(4-acetylaminophenacyl)-alkylamines of the general formula ##STR1## in which R is isopropyl or tert.-butyl, and their addition salts. These new products are useful in therapy, especially as antidepressants for the CNS.Type: GrantFiled: October 12, 1984Date of Patent: October 8, 1985Assignee: Laboratoire L. LafonInventor: Louis Lafon
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Patent number: 4543424Abstract: In the process of preparing substituted formamides by the catalytic oxidation of substituted tertiary amines, in which a metal halide catalyst is used in conjunction with an alkali metal halide corrosion inhibitor, pitting of equipment can be inhibited by including in the reaction medium a primary alkylamine, urea or a substituted urea, or thiourea or a substituted thiourea.Type: GrantFiled: April 9, 1984Date of Patent: September 24, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harold E. Bellis
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Patent number: 4540815Abstract: Process for the preparation of pure 3-acetylaminoanilines of the general formula (1) ##STR1## in which R denotes a hydrogen atom or an alkoxy group with 1-4 carbon atoms, by reduction of 1,3-dinitrobenzene in an alkanol with 1-4 carbon atoms to the 1,3-diaminobenzene or by reaction of 2,4-dinitrochlorobenzene with sodium hydroxide in an alkanol with 1-4 carbon atoms and subsequent reduction to the 2,4-diaminoalkoxybenzene, and in each case subsequent monoacetylation in the alkanol mentioned to give the 1-amino-3-acetylamino-benzene or the 2-amino-4-acetylamino-alkoxy-benzene and isolation of the compound of the above formula (1) obtained in the alkanolic solution, which optionally contains water, which comprises carrying out the isolation by precipitation of the compound of the above formula (1), in the form of the hydrohalide, from the alkanolic solution by means of hydrogen halide or aqueous hydrogen halide acid and subsequent filtration.Type: GrantFiled: November 16, 1984Date of Patent: September 10, 1985Assignee: Hoechst AktiengesellschaftInventors: Theodor Papenfuhs, Manfred Hintzmann
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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: 4540816Abstract: Process for preparing ring-substituted N-alkylanilines of the formula (1) ##STR1## in which R.sub.1 and R.sub.2 each denote methyl or ethyl, in a single vessel, which comprises acylating m-nitroaniline in an excess of an aliphatic carbonyl compound of the formula (2) ##STR2## in which R.sub.1 is as defined above, with an acylating agent which contains the --CO--R.sub.2 acyl radical--which is transferred-- and reductively alkylating the resulting compound of the formula (3) ##STR3## in which R.sub.2 is as defined above, at temperatures of 120.degree.-160.degree. C. under a hydrogen pressure of 20-150 bar without intermediate isolation through the presence of an acid reaction promoter and of a nickel catalyst.Type: GrantFiled: May 10, 1984Date of Patent: September 10, 1985Assignee: Hoechst AktiengesellschaftInventors: Karl Sommer, Rudolf Schickfluss
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Patent number: 4540817Abstract: A process for the preparation of 5-amino-2,4-dimethylacetanilide by reduction of 5-nitro-2,4-dimethylacetanilide with hydrogen is disclosed characterized in that a crude mixture containing 5-nitro-2,4-dimethylacetanilide in admixture with at least one of its position isomers is hydrogenated in a water-miscible organic solvent which optionally contains water. The 5-amino-2,4-dimethylacetanilide is separated off from the reaction mixture by means of crystallization employing a mixture of water-miscible organic solvent and water.Type: GrantFiled: July 25, 1983Date of Patent: September 10, 1985Assignee: Bayer AktiengesellschaftInventors: Horst Behre, Heinz U. Blank, Alfred Seyberlich, Ferdinand Hagedorn
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Patent number: 4537991Abstract: The present disclosure is concerned with a process of reacting a solid aromatic amine with liquid acetic anhydride to yield a solid amide. The amine is in a flowable particulate form and it is subject to sufficient agitation during the reaction to prevent agglomeration. The amide is recovered as a flowable particulate by evaporation of the acetic acid by product and any excess acetic anhydride.Type: GrantFiled: November 30, 1983Date of Patent: August 27, 1985Assignee: Mobay Chemical CorporationInventors: Ellis Margaret D., Richard L. Ferencz, Dietmar Kalz
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Patent number: 4430262Abstract: Isocyanates and derivatives thereof are prepared by oxidative conversion of compounds having at least one group ##STR1## wherein X represents OY or ##STR2## wherein Y is H, a metal ion or group NR.sup.3 R.sup.4 R.sup.5 R.sup.6 wherein each of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 which may be the same or different, is H, alkyl or (substituted) (alk)aryl and Z is a (substituted) alkyl or aryl group. Phenyl isocyanate and derivatives thereof are preferably prepared electrochemically from the corresponding oxamides and oxanilides.Type: GrantFiled: March 11, 1982Date of Patent: February 7, 1984Assignee: Shell Oil CompanyInventors: Rainer Engels, Jan H. H. Meurs
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Patent number: 4401603Abstract: An improved process for preparation of arylisocyanide dichloride by chlorinating N-arylformamide in the presence of thionyl chloride wherein the improvement comprises preparing the N-arylformamide by formylation of an arylamine having 6 to 12 aryl carbon atoms with a formylating agent in an inert solvent.removing excess formylating agent and by-products of the formylation thereby leaving the N-arylformamide in the form of a solution or suspension in the inert solvent and chlorinating the N-arylformamide in solution or suspension with a chlorinating agent in the presence of thionyl chloride.Type: GrantFiled: July 1, 1982Date of Patent: August 30, 1983Assignee: Cassella AktiengesellschaftInventors: Dieter Ferchland, Ulrich Kussmaul, Manfred Langer, Rolf Muller
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Patent number: 4385069Abstract: N-allenyl-acetanilides of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl or halogen,R.sup.2 represents hydrogen or alkyl,R.sup.3 represents hydrogen or alkyl,R.sup.4 represents hydrogen or alkyl,R.sup.5 represents hydrogen or alkyl andR.sup.6 represents furyl, tetrahydrofuryl, thiophenyl or tetrahydrothiophenyl; isoxazolyl which is optionally substituted by alkyl; alkyl, alkenyl or alkynyl, in each case optionally substituted by cyano or thiocyano; dihalogenoalkyl; or the grouping --CH.sub.2 --Az, --CH.sub.2 --OR.sup.7, --OR.sup.7 --SR.sup.7, --CH.sub.2 --OSO.sub.2 R.sup.7, --COOR.sup.7 or ##STR2## wherein R.sup.7 represents an optionally substituted alkyl, alkenyl, alkynyl or alkoxyalkyl radical and Az represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl.which possess fungicidal properties.Type: GrantFiled: March 31, 1980Date of Patent: May 24, 1983Assignee: Bayer AktiengesellschaftInventors: Jorg Stetter, Winfried Lunkenheimer, Wilhelm Brandes
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Patent number: 4377587Abstract: The invention relates to novel microbicides of the general formula I ##STR1## wherein R is hydrogen or methyl, Ar is a phenyl or .alpha.-naphthyl group which is substituted by NH.sub.2 or NO.sub.2 and further radicals, W is a cyano, ester, alkenyl or alkynyl group, and B is alkyl, alkenyl, cyclopropyl, 2-furyl, 2-tetrahydrofuryl, .beta.-(alkoxy)ethyl, triazolylmethyl, methylsulfonylmethyl, alkoxymethyl, alkenyloxymethyl, alkynyloxymethyl, alkylthiomethyl, alkenylthiomethyl, alkynylthiomethyl, --OSO.sub.2 -alkyl, --OSO.sub.2 NH(alkyl) or --N(alkyl).sub.2. The invention also describes plant protection compositions which contain these compounds, a process for the production of the novel compounds and compositions, and a method of controlling phytopathogenic microorganisms which comprises the use thereof.Type: GrantFiled: July 21, 1981Date of Patent: March 22, 1983Assignee: Ciba-Geigy CorporationInventors: Adolf Hubele, Wolfgang Eckhardt, Peter Riebli
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Patent number: 4370497Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.Type: GrantFiled: August 7, 1980Date of Patent: January 25, 1983Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
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Patent number: 4364956Abstract: Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or 5-tetrazolylaminocarbonyl, where R.sup.5 is hydrogen or C.sub.1-6 alkyl; R.sup.2 is hydrogen or C.sub.1-6 alkyl; R.sup.3 is a group of the formulaR.sup.6 --(Z).sub.m --where m is O or 1, Z is O, S, SO, SO.sub.2 or CO, and R.sup.6 phenyl optionally substituted by one or more group selected from halogen, C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.1-4 alkoxy, benzyloxy, hydroxy, nitro, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, amino and NHR.sup.7 where R.sup.7 is C.sub.2-6 acyl; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. These compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.Type: GrantFiled: September 17, 1981Date of Patent: December 21, 1982Assignee: Lilly Industries LimitedInventors: Barry P. Clark, William J. Ross, Alec Todd
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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: 4361440Abstract: Compounds of the general structural formula, ##STR1## in which R.sup.1 is C.sub.1 to C.sub.4 lower alkyl, cycloalkyl or alkylamino and R.sup.2 is H or lower N-alkylcarbamyl are made from corresponding m-aminophenylacetylenic compounds by conventional methods and are useful as selective herbicides.Type: GrantFiled: August 31, 1981Date of Patent: November 30, 1982Assignee: Gulf Oil CorporationInventors: Edward T. Sabourin, Charles M. Selwitz
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Patent number: 4341902Abstract: The present invention is directed to a process for preparing 5-nitro-acet-2,4-xylidine comprising(a) dissolving acet-2,4-xylidine in an aqueous sulfuric acid solution,(b) nitrating the resultant solution with a mixture of nitric acid and sulfuric acid,(c) adding the resultant nitration mixture to an aqueous sulfuric acid solution containing from 25 to 45% by weight of sulfuric acid, while maintaining the temperature at from 20.degree. to 50.degree. C. to thereby produce a slurry containing sulfuric acid in a concentration of from 30 to 50% by weight based solely on the weight of water and sulfuric acid, the total amount of sulfuric acid in said slurry being such that the molar ratio of sulfuric acid to the nitro-acet-2,4-xylidine isomers is from 53:1 to 10:1, and(d) recovering 5-nitro-acet-2,4-xylidine.Type: GrantFiled: June 26, 1981Date of Patent: July 27, 1982Assignee: Mobay Chemical CorporationInventors: Karl W. Thiem, Daniel P. Vanderpool
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Patent number: 4339618Abstract: The invention relates to a process for the production of nitroaryl compounds which are at least monosubstituted, by nitration of aryl compounds which are at least monosubstituted, which process comprises carrying out the nitration in a two-phase system which consists of an inorganic phase consisting of sulfuric acid having a concentration of at least 80% and an organic phase consisting of an inert organic liquid in which the nitration product is almost insoluble in the presence of sulfuric acid, at a temperature in the range from -30.degree. to 100.degree. C., with nitric acid as nitrating agent.The novel process can be generally employed for aryl compounds which are at least monosubstituted. The corresponding nitroaryl compounds are obtained in high yield and isomeric purity.Type: GrantFiled: June 17, 1980Date of Patent: July 13, 1982Assignee: Ciba-Geigy AGInventor: Manfred Rosner
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Patent number: 4329363Abstract: The present application discloses a method of correcting an imbalance of immune homeostasis caused by cytostatic treatment or radiotherapy by administering to a patient in need of such treatment an effective amount of a novel substituted mercapto acid amide and pharmaceutical compositions containing such novel substituted mercapto acid amides.Type: GrantFiled: January 16, 1980Date of Patent: May 11, 1982Assignee: Merck & Co., Inc.Inventors: Conrad P. Dorn, Howard Jones
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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: 4322553Abstract: The disclosure herein relates to a new process for the preparation of N-(halomethyl)acylamides by reacting the corresponding N-(alkoxymethyl)acylamide with thionyl chloride or thionyl bromide in the presence of a Lewis Acid catalyst.Type: GrantFiled: February 2, 1981Date of Patent: March 30, 1982Assignee: Monsanto CompanyInventor: John P. Chupp
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Patent number: 4311858Abstract: The disclosure herein relates to a new process for the preparation of N-(halomethyl) acylamides by reacting the corresponding N-(alkoxymethyl) acetamide with a hydrogen halide.Type: GrantFiled: December 1, 1980Date of Patent: January 19, 1982Assignee: Monsanto CompanyInventor: John P. Chupp
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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: 4301083Abstract: Polyoxyalkylene compounds having at least four oxyalkylene units and one or two terminal hydroxyl groups are etherified by reacting same with organic primary chlorides or bromides in the presence of an aqueous, at least 30% by weight solution of sodium or potassium hydroxide to produce the corresponding etherified polyoxyalkylene derivatives. The molar ratio of the organohalide to the hydroxyl group(s) of the polyoxyalkylene compound is at least 1.2, and the molar ratio of the alkali metal hydroxide to such hydroxyl group(s) is at least 1.Type: GrantFiled: January 2, 1980Date of Patent: November 17, 1981Assignee: Kuraray Co., Ltd.Inventors: Noriaki Yoshimura, Masuhiko Tamura
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Patent number: 4292446Abstract: N-formyl anilino aromatic compounds containing two electronegative groups in the benzene ring, their manufacture from formanilides and aromatic halogen compounds and their use as intermediates for the manufacture of the corresponding diphenylamine compounds. The compounds are useful as pesticides.Type: GrantFiled: July 14, 1980Date of Patent: September 29, 1981Assignee: Imperial Chemical Industries LimitedInventor: Norman Riley
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Patent number: 4281193Abstract: Substituted formamides are prepared by the catalytic oxidation of substituted tertiary amines, in which the catalyst is a metal halide used in conjunction with an alkali metal halide or ammonium halide.Type: GrantFiled: July 16, 1980Date of Patent: July 28, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harold E. Bellis
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Patent number: 4275201Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester.Type: GrantFiled: February 14, 1979Date of Patent: June 23, 1981Assignee: Sterling Drug Inc.Inventor: Joseph C. Collins
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Patent number: T103402Abstract: Couplers of good reactivity contain an aryloxy coupling-off group having in an ortho position a polarizable carbonyl, sulfonyl or phosphinyl substituent group which is free of photographic dye groups and photographic reagent groups.Type: GrantFiled: February 3, 1983Date of Patent: September 6, 1983Inventor: Philip T. S. Lau