Halogen Patents (Class 562/472)
  • Patent number: 4268687
    Abstract: 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: Grant
    Filed: November 7, 1979
    Date of Patent: May 19, 1981
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4268675
    Abstract: 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: Grant
    Filed: July 6, 1979
    Date of Patent: May 19, 1981
    Assignee: PPG Industries, Inc.
    Inventor: Jerome M. Lavanish
  • Patent number: 4267055
    Abstract: 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: Grant
    Filed: September 4, 1979
    Date of Patent: May 12, 1981
    Assignee: Rohm and Haas Company
    Inventor: James W. Neely
  • Patent number: 4251669
    Abstract: 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: Grant
    Filed: January 19, 1978
    Date of Patent: February 17, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Beck, Wilhelm Bartmann, Ulrich Lerch, Bernward Schokens
  • Patent number: 4247710
    Abstract: 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: Grant
    Filed: September 6, 1979
    Date of Patent: January 27, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kenneth E. Fahrenholtz, Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
  • Patent number: 4241215
    Abstract: 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: Grant
    Filed: August 11, 1976
    Date of Patent: December 23, 1980
    Assignee: Imperial Chemical Industries Limited
    Inventor: Jean Bowler
  • Patent number: 4238626
    Abstract: 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: Grant
    Filed: May 11, 1978
    Date of Patent: December 9, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Nahm, Ernold Granzer
  • Patent number: 4233054
    Abstract: 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: Grant
    Filed: March 12, 1979
    Date of Patent: November 11, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Henry Szczepanski, Otto Rohr, Georg Pissiotas, Beat Bohner, Hermann Rempfler
  • Patent number: 4219663
    Abstract: 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: Grant
    Filed: June 28, 1978
    Date of Patent: August 26, 1980
    Assignee: SmithKline Corporation
    Inventor: Jacqueline S. Laforest
  • Patent number: 4218378
    Abstract: 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: Grant
    Filed: May 1, 1979
    Date of Patent: August 19, 1980
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4215044
    Abstract: Process for preparing an organic compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3, which process comprises contacting and reacting in a reaction mixture which includes an inert solvent, at a temperature of -40.degree. C. to -100.degree. C., ROF and ##STR1## R is polyfluoroperhaloalkyl of 1-6 carbon atoms or FOCF.sub.2 ; R.sup.1 is hydrocarbyl of 1-6 carbon atoms;each R.sup.2 is selected from H, alkyl of 1-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, aryl, heteroaryl and such alkyl, cycloalkyl, aryl and heteroaryl substituted by halogen or alkoxy of 1-6 carbon atoms;R.sup.3 is selected from H, alkyl and haloalkyl of 1-16 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl and haloaryl, OSi(R.sup.1).sub.3, OH, NH.sub.2, alkoxy of 1-6 carbon atoms, aryloxy, NHR.sup.1 and NR.sup.1.sub.2 wherein R.sup.1 is alkyl of 1-6 carbon atoms, N-arylamino and nitrogen or sulfur heterocyclic of 4-5 carbon atoms;R.sup.3 and one R.sup.2 taken together is a diradical which with the C.dbd.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: July 29, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William J. Middleton
  • Patent number: 4207343
    Abstract: 1-Phenyl-3-(optionally substituted phenoxy)-propylamines, inhibitors of norepinephrine uptake.
    Type: Grant
    Filed: June 22, 1978
    Date of Patent: June 10, 1980
    Assignee: Eli Lilly and Company
    Inventors: Edward R. Lavagnino, Lawrence J. McShane, Bryan B. Molloy
  • Patent number: 4201727
    Abstract: 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: Grant
    Filed: May 10, 1979
    Date of Patent: May 6, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ka-Kong Chan, Beverly A. Pawson
  • Patent number: 4200587
    Abstract: 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: Grant
    Filed: November 20, 1978
    Date of Patent: April 29, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Milos Suchy
  • Patent number: 4199597
    Abstract: 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: Grant
    Filed: May 4, 1979
    Date of Patent: April 22, 1980
    Assignee: Schering Corporation
    Inventors: Bernard R. Neustadt, Elijah H. Gold
  • Patent number: 4198527
    Abstract: Novel esters of ether and thioether substituted cyclopropanecarboxylic acids, synthesis thereof, and intermediates therefor, such esters being useful as pesticides.
    Type: Grant
    Filed: September 15, 1978
    Date of Patent: April 15, 1980
    Assignee: Zoecon Corporation
    Inventor: Clive A. Henrick
  • Patent number: 4198418
    Abstract: 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: Grant
    Filed: January 10, 1979
    Date of Patent: April 15, 1980
    Assignee: American Hoechst Corporation
    Inventors: Helen H. Ong, James A. Profitt
  • Patent number: 4192669
    Abstract: Ethers, such as 2-[[4-[4-(trifluoromethoxy)phenoxy]phenoxy]]propanoic acid, methyl ester, useful for control of weeds.
    Type: Grant
    Filed: December 22, 1977
    Date of Patent: March 11, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John B. Adams, Jr., Joel B. Wommack, Jr.
  • Patent number: 4182905
    Abstract: 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: Grant
    Filed: September 2, 1977
    Date of Patent: January 8, 1980
    Assignee: Monsanto Company
    Inventor: Kent P. Lannert
  • Patent number: 4182902
    Abstract: p-(p'-chlorobenzyl) phenoxyacetic acid.
    Type: Grant
    Filed: September 13, 1978
    Date of Patent: January 8, 1980
    Assignee: Siegfried Aktiengesellschaft
    Inventors: Kurt Thiele, Quazi Armed, Rudolf Adrian, Ulrich Jahn
  • Patent number: 4175203
    Abstract: 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: Grant
    Filed: December 13, 1978
    Date of Patent: November 20, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., John B. Bicking
  • Patent number: 4174458
    Abstract: 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: Grant
    Filed: May 3, 1978
    Date of Patent: November 13, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Milos Babej, Wilhelm Bartmann, Gerhard Beck, Ulrich Lerch
  • Patent number: 4173709
    Abstract: 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: Grant
    Filed: February 8, 1977
    Date of Patent: November 6, 1979
    Assignee: Rhone-Poulenc S.A.
    Inventors: Jean Metivier, Michel Sauli
  • Patent number: 4168385
    Abstract: 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: Grant
    Filed: February 17, 1977
    Date of Patent: September 18, 1979
    Assignee: American Cyanamid Company
    Inventors: Ronald I. Trust, Francis J. McEvoy, Jay D. Albright
  • Patent number: 4168386
    Abstract: 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: Grant
    Filed: July 12, 1978
    Date of Patent: September 18, 1979
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4166912
    Abstract: 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: Grant
    Filed: July 12, 1978
    Date of Patent: September 4, 1979
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4163661
    Abstract: 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: Grant
    Filed: June 26, 1978
    Date of Patent: August 7, 1979
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Kazuo Jikihara, Shigekazu Itoh, Shuichi Takayama, Koichi Sato, Ichiro Kimura, Isao Chiyomaru
  • Patent number: 4156011
    Abstract: 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: Grant
    Filed: April 5, 1977
    Date of Patent: May 22, 1979
    Assignee: Societe Anonyme dite: Laboratoire L. Lafon
    Inventors: Victor Lafon, Louis Lafon
  • Patent number: 4153803
    Abstract: 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: Grant
    Filed: March 1, 1977
    Date of Patent: May 8, 1979
    Assignee: Siegfried Aktiengesellschaft
    Inventors: Kurt Thiele, Quazi Ahmed, Rudolf Adrian, Ulrich Jahn
  • Patent number: 4148915
    Abstract: 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: Grant
    Filed: November 8, 1976
    Date of Patent: April 10, 1979
    Assignee: Albert Rolland, S.A.
    Inventors: Germaine Thuillier, Sylviane S. J. Mignonac, Pierre A. R. Bessin
  • Patent number: 4146385
    Abstract: The invention provides novel phenoxyalkylcarboxylic acids which are useful in therapy as metabolic regulators and in agriculture as selective herbicides.
    Type: Grant
    Filed: August 16, 1976
    Date of Patent: March 27, 1979
    Assignee: Societe de Recherches Industrielles S.O.R.I.
    Inventor: Bernard Majoie
  • Patent number: 4140520
    Abstract: 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: Grant
    Filed: April 8, 1977
    Date of Patent: February 20, 1979
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Rikuo Nasu, Nobuyuki Sakashita
  • Patent number: 4134753
    Abstract: 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: Grant
    Filed: July 18, 1977
    Date of Patent: January 16, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Horlein, Hubert Schonowsky, Hermann Bieringer, Peter Langeluddeke
  • Patent number: 4126636
    Abstract: 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: Grant
    Filed: October 13, 1977
    Date of Patent: November 21, 1978
    Assignee: Paul Hauser - Chepharin, chemisch-pharmazeutische Industriegesellschaft in Klagenfurt
    Inventor: Franz Stuckler
  • Patent number: 4112224
    Abstract: 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: Grant
    Filed: June 30, 1977
    Date of Patent: September 5, 1978
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy