Halogen Patents (Class 562/472)
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Patent number: 4268687Abstract: The present invention provides a novel process for the production of methyl or ethyl ester of (3-trifluoromethylphenyl)-acetic acid. The process comprises the steps of:(a) converting (3-trifluoromethyl)-benzotrichloride to the corresponding benzoyl chloride,(b) cyanation of the benzoyl chloride to produce the corresponding benzoyl cyanide,(c) hydrolyzing the benzoyl cyanide to produce the corresponding keto-acid,(d) hydrogenating the keto-acid to produce (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid,(e) hydrogenating (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid in the presence of glacial acetic acid to produce the corresponding substituted acetic acid, and(f) esterifying the substituted acetic acid using an alcohol selected from the group consisting of methyl and ethyl to obtain the corresponding methyl or ethyl ester of (3-trifluoromethylphenyl)-acetic acid.Type: GrantFiled: November 7, 1979Date of Patent: May 19, 1981Assignee: Hooker Chemicals & Plastics Corp.Inventors: David Y. Tang, Arthur M. Foster
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Patent number: 4268675Abstract: The disclosed compounds, such as 3-[5-[1-(3,5-dichlorophenoxy) ethyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinone, are useful for preemergence control of weeds, such as jimsonweed.Type: GrantFiled: July 6, 1979Date of Patent: May 19, 1981Assignee: PPG Industries, Inc.Inventor: Jerome M. Lavanish
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Patent number: 4267055Abstract: Planar organic molecules, such as divinylbenzene or para-dioxin molecules, are adsorbed from mixtures of planar and non-planar molecules, such as commercial divinylbenzenes containing non-planar ethylvinylbenzene, or commercial 2,4,5-T herbicide containing non-planar 2,4,5-trichlorophenoxyacetic acid, by partially pyrolyzed, macroporous, resinous polymer particles.Type: GrantFiled: September 4, 1979Date of Patent: May 12, 1981Assignee: Rohm and Haas CompanyInventor: James W. Neely
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Patent number: 4251669Abstract: The present invention relates to new analogues which do not occur naturally of prostanoic acids of the formula I ##STR1## The compounds of the invention have spasmogenic, bronchodilatant and hypotensive properties. Therefore, they can be used as medicaments.This invention also relates to a process for preparing the compounds of the invention.Type: GrantFiled: January 19, 1978Date of Patent: February 17, 1981Assignee: Hoechst AktiengesellschaftInventors: Gerhard Beck, Wilhelm Bartmann, Ulrich Lerch, Bernward Schokens
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Patent number: 4247710Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR2## R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof.There are also disclosed processes and intermediate utilized to produce the end products.The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.Type: GrantFiled: September 6, 1979Date of Patent: January 27, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Kenneth E. Fahrenholtz, Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
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Patent number: 4241215Abstract: The disclosure relates to novel 4-cis-prostenoic acid derivatives, for example 16-(3-chlorophenoxy)-9.alpha.,11.alpha.,15-trihydroxy-17,18,19,20-tetranor -4-cis, 13-trans-prostadienoic acid, to chemical processes for their manufacture, to pharmaceutical and veterinary compositions containing them, and to the use of the compounds in a method of luteolysis, a method of inhibiting blood platelet aggregation, and a method of inhibiting gastric acid production.Type: GrantFiled: August 11, 1976Date of Patent: December 23, 1980Assignee: Imperial Chemical Industries LimitedInventor: Jean Bowler
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Patent number: 4238626Abstract: Novel 4-phenoxy-phenoxy-alkane-carboxylic acid derivatives of the formula I ##STR1## in which R.sub.1 stands for hydrogen, methylthio, cyclopentyl, cyclohexyl, phenyl, methylcyclohexyl, ethylcyclohexyl, or R.sub.1 and R.sub.3 together stand for a --CH.dbd.CH--CH.dbd.CH-- bridge or--unless at least one of the substituents R.sub.2 to R.sub.8 stands for hydrogen, or if R.sub.9 stands for a radical having at least 2 carbon atoms--for chlorine,R.sub.2 and R.sub.3, independent of one another, each stands for hydrogen, chlorine or alkyl of 1 to 4 carbon atoms,R.sub.4 stands for hydrogen, chlorine, alkyl of 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, methylcyclohexyl or R.sub.3 and R.sub.4 together stand for a --CH.dbd.CH--CH.dbd.CH-- bridge,R.sub.5, R.sub.6 and R.sub.7, independent of one another, each stands for hydrogen or alkyl of 1 to 4 carbon atoms,R.sub.8 stands for hydrogen, alkyl of 1 to 4 carbon atoms or allyl,R.sub.Type: GrantFiled: May 11, 1978Date of Patent: December 9, 1980Assignee: Hoechst AktiengesellschaftInventors: Helmut Nahm, Ernold Granzer
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Patent number: 4233054Abstract: New phenoxy-alkanecarboxylic acid derivatives which have a herbicidal action and which are effective in regulating plant growth are described. They correspond to the formula ##STR1## in which A is the cyano group, a carboxylic acid, a salt, ester, thioester or amide thereof,Q is a mono- to trisubstituted phenyl or pyrid-2-yl radical,R.sub.3 is hydrogen, halogen, cyano, nitro, alkyl or carbamoyl,R.sub.4 is alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, phenyl or benzyl, andX, Y and Z are each oxygen or sulfur.They can be used as selective herbicides in cereal and rice crops, or for reducing the vegetative growth, for example in soya-bean crops, and also for defoliation and desiccation in cotton or potato crops shortly before the harvesting thereof.Type: GrantFiled: March 12, 1979Date of Patent: November 11, 1980Assignee: Ciba-Geigy CorporationInventors: Henry Szczepanski, Otto Rohr, Georg Pissiotas, Beat Bohner, Hermann Rempfler
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Patent number: 4219663Abstract: 2,3-Dichloro-4-(2-thenoyl)phenoxyacetic acid (tienilic acid) is prepared by reacting (2,3-dichloro-4-carboxy)phenoxyacetic acid with thiophene in the presence of a dehydration agent. The (2,3-dichloro-4-carboxy)phenoxyacetic acid is a novel compound.Type: GrantFiled: June 28, 1978Date of Patent: August 26, 1980Assignee: SmithKline CorporationInventor: Jacqueline S. Laforest
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Patent number: 4218378Abstract: The present invention provides novel 11a-methano-TXA compounds and intermediates and processs for their preparation. Further provided are methods for using these novel TXA analogs as inhibitors of thromboxane synthetase, rendering these analogs useful for a variety of pharmacological purposes. These pharmacological uses include anti-inflammatory, anti-thromobitc, and anti-asthma indications.Type: GrantFiled: May 1, 1979Date of Patent: August 19, 1980Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4215044Abstract: 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: GrantFiled: April 23, 1979Date of Patent: July 29, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: William J. Middleton
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Patent number: 4207343Abstract: 1-Phenyl-3-(optionally substituted phenoxy)-propylamines, inhibitors of norepinephrine uptake.Type: GrantFiled: June 22, 1978Date of Patent: June 10, 1980Assignee: Eli Lilly and CompanyInventors: Edward R. Lavagnino, Lawrence J. McShane, Bryan B. Molloy
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Patent number: 4201727Abstract: Compounds represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are lower alkyl, R.sub.4 is lower alkoxy, R.sub.6 and R.sub.8 are methyl or trifluoro methyl, R.sub.9 is formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, lower alkenoxycarbonyl, lower alkynoxycarbonyl, carbamoyl, mono(lower alkyl)-carbamoyl, di(lower alkyl)carbamoyl or N-heterocyclylcarbonyl, R.sub.5, R.sub.7, R.sub.10, R.sub.11 R.sub.12 and R.sub.13 are hydrogen or fluorine with the proviso that at least one of R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 or R.sub.13 is fluorine or at least one of R.sub.6 or R.sub.8 is trifluoro methyl,or pharmaceutically acceptable salts thereof useful as antitumor agents are disclosed.Type: GrantFiled: May 10, 1979Date of Patent: May 6, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, Beverly A. Pawson
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Patent number: 4200587Abstract: 2-[p-(p-substituted phenoxy)phenoxy] propionyl oximes, processes for their preparation, herbicidal compositions containing these oximes and methods of use of the herbicidal compositions are disclosed.Type: GrantFiled: November 20, 1978Date of Patent: April 29, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Milos Suchy
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Patent number: 4199597Abstract: Omega-[4-(polyfluoro-2-hydroxy-2-propyl)-2,3,6-substituted-phenoxy and phenylthio]alkanoic acids and compounds related thereto having antihypertensive activity are preparable by reaction of the appropriate 2,3,6-substituted-4-(polyfluoro-2-hydroxy-2-propyl)phenol or thiophenol with an alkyl ester of a bromoalkanoic acid, followed by hydrolysis to the free acid.Type: GrantFiled: May 4, 1979Date of Patent: April 22, 1980Assignee: Schering CorporationInventors: Bernard R. Neustadt, Elijah H. Gold
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Patent number: 4198527Abstract: Novel esters of ether and thioether substituted cyclopropanecarboxylic acids, synthesis thereof, and intermediates therefor, such esters being useful as pesticides.Type: GrantFiled: September 15, 1978Date of Patent: April 15, 1980Assignee: Zoecon CorporationInventor: Clive A. Henrick
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Patent number: 4198418Abstract: Novel spiro[dibenz(b,f)oxepin-piperidine]s and methods of preparing same are described. These compounds are useful as analgetics, tranquilizers and anticonvulsants.Type: GrantFiled: January 10, 1979Date of Patent: April 15, 1980Assignee: American Hoechst CorporationInventors: Helen H. Ong, James A. Profitt
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Patent number: 4192669Abstract: Ethers, such as 2-[[4-[4-(trifluoromethoxy)phenoxy]phenoxy]]propanoic acid, methyl ester, useful for control of weeds.Type: GrantFiled: December 22, 1977Date of Patent: March 11, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventors: John B. Adams, Jr., Joel B. Wommack, Jr.
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Patent number: 4182905Abstract: Organic compounds having a substituent represented by the formula ##STR1## wherein M is alkali metal or ammonium are useful complexing agents for metal and/or alkaline earth metal ions.Type: GrantFiled: September 2, 1977Date of Patent: January 8, 1980Assignee: Monsanto CompanyInventor: Kent P. Lannert
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Patent number: 4182902Abstract: p-(p'-chlorobenzyl) phenoxyacetic acid.Type: GrantFiled: September 13, 1978Date of Patent: January 8, 1980Assignee: Siegfried AktiengesellschaftInventors: Kurt Thiele, Quazi Armed, Rudolf Adrian, Ulrich Jahn
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Patent number: 4175203Abstract: Novel interphenylene derivatives of 11,12-secoprostaglandins are prepared by the stepwise alkylation of the ethyl ester or the t-butyl ester of acetoacetic acid. One such method involves treatment of the t-butyl ester of acetoacetic acid with a strong base to form the anion followed by treatment with ethyl p-(3-bromopropyl)benzoate to produce ethyl 4-(4-tert-butoxycarbonyl-5-oxo-hexyl)benzoate, subsequently reacting the anion of the thus-formed benzoate with 1-chloro-4-acetoxynonane to produce ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxytridecyl)benzoate followed by decarboxylation and alkaline hydrolysis to produce the desired product 4-(4-acetyl-8-hydroxytridecyl)benzoic acid which is useful as a pharmaceutical in the treatment of patients with renal failure and in the prevention of transplant rejection.Type: GrantFiled: December 13, 1978Date of Patent: November 20, 1979Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., John B. Bicking
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Patent number: 4174458Abstract: The present invention relates to novel not naturally occurring analogues of prostanoic acids of the formula ##STR1## as well as a process for their preparation. The compounds of the invention have valuable pharmacological properties similar to those of the natural prostaglandins and therefore can be used as medicaments.Type: GrantFiled: May 3, 1978Date of Patent: November 13, 1979Assignee: Hoechst AktiengesellschaftInventors: Milos Babej, Wilhelm Bartmann, Gerhard Beck, Ulrich Lerch
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Patent number: 4173709Abstract: Dextrorotatory 2-phenoxypropionic acids are made by heating an alkali metal salt of dextrorotatory 2-chloropropionic acid with an alkali metal phenate in an inert organic solvent of high boiling point under reflux.Type: GrantFiled: February 8, 1977Date of Patent: November 6, 1979Assignee: Rhone-Poulenc S.A.Inventors: Jean Metivier, Michel Sauli
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Patent number: 4168385Abstract: This invention discloses .alpha.-aryloxy or .alpha.-arylthio para substituted phenyl acetic acid compounds that are useful in lowering sterol and triglyceride serum levels.Type: GrantFiled: February 17, 1977Date of Patent: September 18, 1979Assignee: American Cyanamid CompanyInventors: Ronald I. Trust, Francis J. McEvoy, Jay D. Albright
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Patent number: 4168386Abstract: The present invention relates to novel 9-deoxy-9-methylene-inter-phenylene-13,14-didehydro-16-phenyl-17,18,19,20- tetranor-PGF.sub.1 compounds. These compounds are useful pharmacological agents, and are useful for the same purposes as the corresponding PGE-type compounds.Type: GrantFiled: July 12, 1978Date of Patent: September 18, 1979Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4166912Abstract: The present invention relates to novel 9-deoxy-9-methylene-inter-phenylene-16-phenyl-PGF compounds.These compounds are useful pharmacological agents, and are useful for the same purposes as the corresponding PGE-type compounds.Type: GrantFiled: July 12, 1978Date of Patent: September 4, 1979Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4163661Abstract: Trifluoromethylphenoxy phenoxy crotonic acid derivatives of the formula ##STR1## wherein X represents hydrogen or halogen atom, and R represents an alkyl, haloalkyl, alkenyl haloalkenyl or alkynyl group are disclosed. These compounds disclose herbicidal activity.Type: GrantFiled: June 26, 1978Date of Patent: August 7, 1979Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Kazuo Jikihara, Shigekazu Itoh, Shuichi Takayama, Koichi Sato, Ichiro Kimura, Isao Chiyomaru
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Patent number: 4156011Abstract: The sulphur- and oxygen-containing diaryl compounds of the formula: ##STR1## in which A and B, which may be the same or different, represent O, S, SO or SO.sub.2,Alk is a C.sub.1 -C.sub.4 hydrocarbon radical with a straight or branched chain, R represents COOH, an esterified COOH group, a carboxylic amide group, OH, O-SO.sub.2 CH.sub.3, NH.sub.2, NHR.sub.1, NR.sub.1 R.sub.2, NHZOH, NHZNR.sub.1 R.sub.2, C(.dbd.NH)NH.sub.2, C(.dbd.NH)NHOH or 2-.DELTA..sup.2 -imidazolinyl, Z is a C.sub.2 -C.sub.4 hydrocarbon radical with a straight or branched chain, and R.sub.1 and R.sub.2 each represent a C.sub.1 -C.sub.Type: GrantFiled: April 5, 1977Date of Patent: May 22, 1979Assignee: Societe Anonyme dite: Laboratoire L. LafonInventors: Victor Lafon, Louis Lafon
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Patent number: 4153803Abstract: Compounds possessing pharmaceutical activity as substances able to lower the level of fatty substances in the blood possess the following general formula: ##STR1## wherein R represents hydrogen, halogen, hydroxy or alkyl or alkoxy containing from 1 to 4 carbon atoms;A.sup.1 and A.sup.2 which can be the same or different are hydrogen or alkyl containing from 1 to 9 carbon atoms such that A.sup.1 and A.sup.Type: GrantFiled: March 1, 1977Date of Patent: May 8, 1979Assignee: Siegfried AktiengesellschaftInventors: Kurt Thiele, Quazi Ahmed, Rudolf Adrian, Ulrich Jahn
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Patent number: 4148915Abstract: Bis (2-phenoxyalkane carboxylic acids) and their esters and salts, as well as a method for their preparation. These compounds are useful for the treatment of hyperlipemia and arteriosclerosis.Type: GrantFiled: November 8, 1976Date of Patent: April 10, 1979Assignee: Albert Rolland, S.A.Inventors: Germaine Thuillier, Sylviane S. J. Mignonac, Pierre A. R. Bessin
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Patent number: 4146385Abstract: The invention provides novel phenoxyalkylcarboxylic acids which are useful in therapy as metabolic regulators and in agriculture as selective herbicides.Type: GrantFiled: August 16, 1976Date of Patent: March 27, 1979Assignee: Societe de Recherches Industrielles S.O.R.I.Inventor: Bernard Majoie
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Patent number: 4140520Abstract: Phenoxy malonic acids and derivatives thereof represented by the general formula (I): ##STR1## wherein X is a 4-trifluoromethylphenoxy group or a 3,5-dichloropyridyl-2-oxy group; and R is a hydroxy group, an --O-- cation group or a (C.sub.1 - C.sub.4)alkoxy group, useful as a herbicide; a herbicidal composition containing the compound; and methods of controlling weeds using such materials.Type: GrantFiled: April 8, 1977Date of Patent: February 20, 1979Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Rikuo Nasu, Nobuyuki Sakashita
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Patent number: 4134753Abstract: Compounds of the formula ##STR1## exhibit, in the pre-emergence process and in the post-emergence process, a good herbicidal action against a number of dicotyledonous weeds, they are well tolerated in monocotyledonous crops, such as wheat, barley, rice, sorghum and maize, and are also selectively active in some dicotyledonous crops such as soy beans, groundnuts and the like.Type: GrantFiled: July 18, 1977Date of Patent: January 16, 1979Assignee: Hoechst AktiengesellschaftInventors: Gerhard Horlein, Hubert Schonowsky, Hermann Bieringer, Peter Langeluddeke
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Patent number: 4126636Abstract: P-chlorophenoxyisobutyric acid is dissolved in an aqueous solution of a surplus of ammonia. The resulting solution is reacted with an aqueous solution of a magnesium salt, which latter solution contains a large surplus of ammonium ions and gaseous ammonia.Type: GrantFiled: October 13, 1977Date of Patent: November 21, 1978Assignee: Paul Hauser - Chepharin, chemisch-pharmazeutische Industriegesellschaft in KlagenfurtInventor: Franz Stuckler
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Patent number: 4112224Abstract: The present specification; provides bicyclic nitrogen-containing 9,11,15-trideoxy-prostaglandin F analogs which are useful anti-inflammatory agents, anti-asthma agents, and platelet aggregation inhibitors, and a process for their preparation. Included are compounds of the following structural formulas: ##STR1## Especially described in the present specification are 9,11-trideoxy-9.alpha.,11.alpha.-azo-PGF-type; 9,11,15-trideoxy-11.alpha.,9.alpha.-epoxyimino-PGF-type; 9,11,15-trideoxy-9.alpha.,11.alpha.-epoxyimino-PGF-type; N,N'-dialkyl-9,11,15-trideoxy-9.alpha.11.alpha.-hydrazino-PGF-type; N,N'-bis(alkylcarbonyl)-9,11,15-trideoxy-9.alpha.,11.alpha.-hydrazino-PGF- type; N-alkyl-9,11,15-trideoxy-11.alpha.,9.alpha.-epoxyimino-PGF-type; N-(alkylcarbonyl)-9,11,15-trideoxy-11.alpha.,9.alpha.-epoxyimino-PGF-type; N-alkyl-9,11,15-trideoxy-9.alpha.,11.alpha.-epoxyimino-PGF-type; N-(alkylcarbonyl)-9,11,15-trideoxy-9.alpha.,11.alpha.-epoxyimino-PGF-type; 9,11,15-trideoxy-9.alpha.,11.alpha.Type: GrantFiled: June 30, 1977Date of Patent: September 5, 1978Assignee: The Upjohn CompanyInventor: Gordon L. Bundy