Halogen In Acid Moiety Patents (Class 560/62)
  • Patent number: 4358409
    Abstract: Styryl-cyclopropane derivatives of the formula ##STR1## in which R.sup.9 represents independently of one another when n=2, halogen, cyano, nitro, or an optionally halogen-substituted alkyl, alkoxy, alkylthio or alkylenedioxy radical,n represents zero, 1, 2, 3, 4 or 5,R.sup.10 represents hydrogen or halogenandY represents acetyl, cyano or carbamoyl, are produced by reacting a benzylphosphonic acid ester of the formula ##STR2## in which R.sup.4 each independently represents alkyl or phenyl or together represent alkylene, with a formylcyclopropane derivative of the formula ##STR3## or by reacting an .alpha.-hydroxyphosphonic acid ester of the formula ##STR4## with an olefinating agent of the formula ##STR5## in which Z' represents a phosphorus-containing radical ##STR6## wherein R.sup.5 and R.sup.6 are identical or different and individually represent alkyl, phenyl, alkoxy or pehnoxy or R.sup.5 and R.sup.6 together represent alkanedioxy,R.sup.
    Type: Grant
    Filed: April 16, 1980
    Date of Patent: November 9, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hellmut Hoffmann, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
  • Patent number: 4356187
    Abstract: Novel esters of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of carbamoyl and R.sub.1 ' and R.sub.2 ', R.sub.1 ' and R.sub.2 ' are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 13 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms and --CN, R.sub.3 and R.sub.3 ' are individually selected from the group consisting of hydrogen, halogen, alkenyl of 2 to 3 carbon atoms and alkyl of 1 to 3 carbon atoms, Y' is selected from the group consisting of ##STR2## R.sub.4 ' and R.sub.5 ' are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, fluorine, bromine, chlorine and R.sub.4 ' and R.sub.
    Type: Grant
    Filed: April 17, 1980
    Date of Patent: October 26, 1982
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Andre Teche
  • Patent number: 4354034
    Abstract: This invention relates to dihalophenoxypropionic acids and their derivatives useful for desiccating cotton plants, to a process for preparing these compounds, to cotton desiccating compositions containing them and to a method of desiccating cotton using them.
    Type: Grant
    Filed: June 15, 1979
    Date of Patent: October 12, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventors: John E. Barton, David J. Collins, Donald W. Headford
  • Patent number: 4351950
    Abstract: Novel substituted arylene compounds and methods for their preparation and use are disclosed. These new compounds are useful as anti-arteriosclerotic agents.
    Type: Grant
    Filed: January 2, 1980
    Date of Patent: September 28, 1982
    Assignee: Warner-Lambert Company
    Inventor: Ila Sircar
  • Patent number: 4348534
    Abstract: 2-Aryloxy-2-halopropionic acid compounds are prepared by reacting 2-aryloxypropionic acid compounds with N-halocarboxylic acid imides in the presence of aliphatic halohydrocarbons as solvents, and of from 0.0001 to 0.001 mole of halogen per mole of N-halocarboxylic acid imide, from 0.005 to 0.05 per cent by weight of water, based on N-halocarboxylic acid imide, and from 0.0005 to 0.005 mole of azo-bis-isobutyronitrile and/or dibenzoyl peroxide, per mole of N-halocarboxylic acid imide.The end products obtainable by the process of the invention are valuable starting materials for the preparation of drugs, crop protection agents and dyes.
    Type: Grant
    Filed: June 17, 1981
    Date of Patent: September 7, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Husslein, Gerhard Hamprecht
  • Patent number: 4339587
    Abstract: Substituted 2-(trifluoroethoxy)benzamide, benzoic acid and benzoate compounds which are intermediates in the preparation of pharmaceutically active agents.
    Type: Grant
    Filed: June 8, 1981
    Date of Patent: July 13, 1982
    Assignee: Riker Laboratories, Inc.
    Inventor: Elden H. Banitt
  • Patent number: 4332960
    Abstract: Compounds of the formula ##STR1## where R.sub.1 is H or Hal and R.sub.2 is a variety of functional groups among which is hydroxy, alkoxy and (substituted) amino, are valuable grass herbicides.
    Type: Grant
    Filed: July 8, 1975
    Date of Patent: June 1, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Trosken, Gerhard Horlein, Ernst-Friedrich Schulze, Peter Langeluddeke
  • Patent number: 4332961
    Abstract: .alpha.-[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the "4-trifluoromethylphenoxy group" of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.
    Type: Grant
    Filed: April 15, 1977
    Date of Patent: June 1, 1982
    Assignee: Ishihara Sangyo Kaisha, Ltd.
    Inventors: Ryohei Takahashi, Kanichi Fujikawa, Isao Yokomichi, Sinzo Someya, Nobuyuki Sakashita
  • Patent number: 4329488
    Abstract: Propionic acid esters of the general formula ##STR1## wherein R.sub.1 is hydrogen, alkyl of from 1 to 6 carbon atoms or phenyl, R.sub.2 is alkyl of from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms, alkynyl of from 2 to 6 carbon atoms or phenyl, or R.sub.1 and R.sub.2 together with the carbon atom to which they are attached form a cycloalkane ring containing 4 to 10 carbon atoms which can be mono-, di- or trisubstituted with alkyl of from 1 to 3 carbon atoms, R.sub.3 represents a halogen, trifluoromethyl or nitro, and R.sub.4 and R.sub.5 each represent a hydrogen or halogen atom, processes for their manufacture, herbicidal compositions containing these compounds as the active ingredient and methods of use of the herbicidal compositions are disclosed.
    Type: Grant
    Filed: December 5, 1980
    Date of Patent: May 11, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Georg Frater, Jean Wenger
  • Patent number: 4327025
    Abstract: A process for the preparation of a styrylcyclopropane-1-carboxylic acid ester of the formula ##STR1## in which R is C.sub.1-4 -alkyl or an alcohol radical customary in pyrethroids,R.sup.1 is alkoxy or alkylthio, either of which may be optionally substituted by halogen,R.sup.2 is hydrogen or alkoxy, orR.sup.1 and R.sup.2 together are optionally halogen-substituted alkylenedioxy, andR.sup.3 is hydrogen or chlorine,comprising reacting an ester of the formula ##STR2## in which Hal is chlorine or bromine,with a base.The compounds are insecticidally active. Numerous syntheses of the starting materials, some involving new intermediates, are also shown.
    Type: Grant
    Filed: April 7, 1980
    Date of Patent: April 27, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Jautelat, Dieter Arlt, Reinhard Lantzsch, Rainer Fuchs, Hans-Jochem Riebel, Rolf Schroder, Horst Harnisch
  • Patent number: 4326882
    Abstract: This invention provides as new compositions of matter 2,4,5-trichlorophenoxy acetic acid (2,4,5-T) and (2-2,4,5-trichlorophenoxy) propionic acid (Silvex) including the hydrolyzable salts, aliphatic esters and amides of these acids, which compositions are free of chlorinated dibenzo-p-dioxins.
    Type: Grant
    Filed: April 26, 1979
    Date of Patent: April 27, 1982
    Assignee: PPG Industries, Inc.
    Inventors: Sidney B. Richter, William S. Grove
  • Patent number: 4325873
    Abstract: A process for the preparation of a styryl-cyclopropane-carboxylic acid ester of the formula ##STR1## in which R is C.sub.1-4 -alkyl or an alcohol radical customary in pyrethroids,R.sup.1 is alkoxy or alkylthio, either of which may be optionally substituted by halogen,R.sup.2 is hydrogen or alkoxy, orR.sup.1 and R.sup.2 together are optionally halogen-substituted alkylenedioxy, andR.sup.3 is hydrogen or chlorine, comprising reacting a compound of the formula ##STR2## with, respectively, one, two or three equivalents of a base at a temperature below 60.degree. C. The products are insecticidally active when R is the residue of a pyrethroid-type alcohol. Various syntheses are given for the starting materials which are new.
    Type: Grant
    Filed: April 7, 1980
    Date of Patent: April 20, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Jautelat, Dieter Arlt, Reinhard Lantzsch, Rainer Fuchs, Hans-Jochem Riebel, Rolf Schroder, Horst Harnisch
  • Patent number: 4316986
    Abstract: Carboxylic ester and acyl fluoride groups are interchanged in the presence of a metal fluoride catalyst or a metal fluoride/strong sulfonic acid catalyst combination to produce fluorinated mono- and diacyl fluorides.
    Type: Grant
    Filed: September 23, 1980
    Date of Patent: February 23, 1982
    Assignee: E. I. DuPont de Nemours & Company
    Inventors: David C. England, Robert L. Kraft, Carl G. Krespan
  • Patent number: 4314069
    Abstract: .alpha.-[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the "4-trifluoromethylphenoxy group" of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.
    Type: Grant
    Filed: April 15, 1977
    Date of Patent: February 2, 1982
    Assignee: Ishihara Sangyo Kaisha, Ltd.
    Inventors: Ryohei Takahashi, Kanichi Fujikawa, Isao Yokomichi, Sinzo Someya, Nobuyuki Sakashita
  • Patent number: 4314086
    Abstract: Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.
    Type: Grant
    Filed: June 20, 1980
    Date of Patent: February 2, 1982
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Daniel Michelet
  • Patent number: 4309547
    Abstract: Process for the preparation of (phenoxy- or benzyl-)-phenoxypropionic acids by simultaneous addition of 2-chloropropionic acid (ester) and the double molar amount of an aqueous alkali hydroxide to a solution of a phenoxyphenol or benzylphenol in a solvent forming an azeotropic mixture with water, while continuously distilling off the water formed or introduced.
    Type: Grant
    Filed: May 30, 1980
    Date of Patent: January 5, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Koch, Hans J. Nestler
  • Patent number: 4309566
    Abstract: Novel substituted benzoyloxy compounds exhibit plant regulator activity, retarding or stimulating the growth of a variety of broadleaved plants, while leaving grasses unaffected. The preparation and plant regulator activity of the compounds is exemplified.
    Type: Grant
    Filed: November 5, 1979
    Date of Patent: January 5, 1982
    Assignee: FMC Corporation
    Inventors: Marvin J. Konz, Norman E. Krog
  • Patent number: 4309562
    Abstract: .alpha.[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the "4-trifluoromethylphenoxy group" of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.
    Type: Grant
    Filed: April 15, 1977
    Date of Patent: January 5, 1982
    Assignee: Ishihara Sangyo Kaisha, Ltd.
    Inventors: Ryohei Takahashi, Kanichi Fujikawa, Isao Yokomichi, Sinzo Someya, Nobuyuki Sakashita
  • Patent number: 4304936
    Abstract: 3-Phenoxy-.alpha.-phenoxy-alkancarboxylic acid derivatives of the formula ##STR1## are disclosed as possessing a surprising selective herbicidal activity. In the formula, Hal is a halogen atom, m is an integer 1, 2 or 3, Y is a hydrogen or halogen atom or the cyano group, Z is a halogen atom or the cyano group, R.sub.1 is hydrogen or C.sub.1 -C.sub.8 alkyl, and R is an acid function. Methods are disclosed for combatting weeds in mono- and dicotyledonous cultures such as cereals, corn, rice, soya and cotton, which comprise applying to the locus to be protected from weeds a dosage of from 0.1 to 10.0 kilograms per hectare of the above compounds.
    Type: Grant
    Filed: October 11, 1979
    Date of Patent: December 8, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Otto Rohr, Georg Pissiotas, Beat Bohner, Kurt Burdeska
  • Patent number: 4303796
    Abstract: Prostaglandin-type compounds with a phenoxy or substituted-phenoxy substituent at the C-16 position are disclosed, with processes for making them. These compounds are useful for a variety of pharmacological purposes, including anti-ulcer, inhibition of platelet aggregation, increase of nasal patency, labor inducement at term, and wound healing.
    Type: Grant
    Filed: December 19, 1973
    Date of Patent: December 1, 1981
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Patent number: 4301295
    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: August 20, 1980
    Date of Patent: November 17, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Nahm, Ernold Granzer
  • Patent number: 4293707
    Abstract: Trichlorophenoxy alkanoic acid including hydrolyzable salts, aliphatic esters and amides thereof said compounds being free of chlorinated dibenzo-p-dioxins are prepared by liquid phase alkaline condensation of 3-chlorophenol or 3,4-dichlorophenol with an alpha halo alkanoic acid, ester or amide followed by liquid phase chlorination of the condensation product.
    Type: Grant
    Filed: June 4, 1979
    Date of Patent: October 6, 1981
    Assignee: PPG Industries, Inc.
    Inventors: Sidney B. Richter, William S. Grove
  • Patent number: 4293434
    Abstract: The invention describes nematic compositions for electrooptical devices for modulation of the transmitted or incident light and for the rendition of numbers, symbols and images as orientation in the spectroscopy and gas chromatography.
    Type: Grant
    Filed: February 13, 1979
    Date of Patent: October 6, 1981
    Assignee: VEB Werk fur Fernsehelektronik Berlin im VEB Kombinat Mikroelektronik
    Inventors: Hans-Joachim Deutscher, Herrmann Schubert, Christina Seidel, Dietrich Demus, Horst Kresse
  • Patent number: 4291057
    Abstract: Novel esters of halo-4-alkenoic acid compounds having pesticidal activity and methods of their preparation.
    Type: Grant
    Filed: July 2, 1979
    Date of Patent: September 22, 1981
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4288630
    Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4278678
    Abstract: Novel substituted oxy-cyclohexylacetic acid derivatives as antihyperlipidemic agents are given. The compounds have the formula ##STR1## wherein n is 1 or 2; m is 0, 1 or 2; R.sub.1 represents a halogen atom, trifluoromethyl, a lower alkyl, a lower alkoxy, a lower alkylcarbonyl, dimethylphenylmethyl, cyclohexyl, phenyl, halogenophenyl, phenoxy or halogenophenoxy group, and two of R.sub.1 groups can be bonded to form an orthocondensed saturated alkylene ring; Hal represents a halogen atom; and R.sub.2 represents a hydrogen atom or a lower alkyl group.
    Type: Grant
    Filed: November 16, 1979
    Date of Patent: July 14, 1981
    Assignee: Kaken Chemical Co., Ltd.
    Inventors: Yasuhiko Hamazaki, Kenji Seri, Nobuo Ishiyama, Toshiyuki Yamamoto, Masao Sakasai, Reiko Sato
  • Patent number: 4277612
    Abstract: The present invention particularly relates to novel .omega.-aryl-9-deoxy-9-methylene-5,6-didehydro-PFG.sub.1 compounds and methods for their preparation in pharmacological use.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: July 7, 1981
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4276429
    Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
    Type: Grant
    Filed: April 28, 1978
    Date of Patent: June 30, 1981
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • Patent number: 4270948
    Abstract: .alpha.-[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the "4-trifluoromethylphenoxy group" of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.
    Type: Grant
    Filed: October 17, 1979
    Date of Patent: June 2, 1981
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryohei Takahashi, Kanichi Fujikawa, Isao Yokomichi, Sinzo Someya, Nobuyuki Sakashita
  • Patent number: 4263445
    Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
    Type: Grant
    Filed: April 28, 1978
    Date of Patent: April 21, 1981
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • Patent number: 4263040
    Abstract: A herbicidal composition which comprises a herbicidally effective amount of a phenoxyphenoxy derivative having the formula ##STR1## wherein X represents a halogen atom or CF.sub.3 ; Y represents a hydrogen atom or a halogen atom; and Z represents --COSR.sup.1 and R.sup.1 represents lower alkyl, phenyl, chlorophenyl, chlorobenzyl or methoxybenzyl; in combination with a suitable carrier is disclosed.
    Type: Grant
    Filed: January 25, 1979
    Date of Patent: April 21, 1981
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Kazuo Jikihara, Shigekazu Itoh, Shuichi Takayama, Koichi Sato, Ichiro Kimura, Isao Chiyomaru
  • Patent number: 4259250
    Abstract: The present invention provides novel thromboxane analogs and intermediates. Particularly, the present invention provides novel 11a-homo-PG intermediates for preparing 11a-methano TXA.sub.2 compounds.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4252980
    Abstract: (Phenoxy- or benzyl)-phenoxypropionic acid methyl esters are produced by esterification of the corresponding anhydrous alkali metal salts with half the molar amount of dimethyl sulfate at a temperature exceeding 120.degree. C.
    Type: Grant
    Filed: October 2, 1979
    Date of Patent: February 24, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Koch, Hilmar Mildenberger
  • Patent number: 4250324
    Abstract: Water-degradable compounds formed from amine-type compounds, aldehydes and aromatic carboxylic acids, the respective components reacting to form a complex ester which upon contact with water slowly degrades to release, at least, the original carboxylic acid.
    Type: Grant
    Filed: November 18, 1977
    Date of Patent: February 10, 1981
    Inventors: Marvin L. Beasley, Norman G. Rhode
  • Patent number: 4243817
    Abstract: This disclosure describes derivatives, analogs, and congeners of prostanoic acid having a terminal cyclic moiety in the .beta.-chain which possess the pharmacological activities associated with the prostaglandins.
    Type: Grant
    Filed: March 30, 1977
    Date of Patent: January 6, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
  • 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: 4235896
    Abstract: Compounds of the formula ##STR1## in which A is lower alkyl, or a substituted or unsubstituted phenyl, thienyl, furyl, indolyl or thiaindolyl radical, R, X.sub.4 and X.sub.5 are hydrogen or lower alkyl, Y is hydrogen, hydroxy, etherified hydroxy, substituted amino, or N-attached heterocyclyl, X.sub.0 is O or OCH.sub.2 CH.sub.2 O, R' represents hydrogen, lower alkyl or acetyl; and acid-addition salts thereof, are novel and useful in pharmacy as hypolipaemiant, hypocholosterolaemiant and cholagogic agents or in the preparation of such agents.
    Type: Grant
    Filed: October 28, 1977
    Date of Patent: November 25, 1980
    Assignee: Orchimed S.A.
    Inventor: Andre Mieville
  • Patent number: 4235736
    Abstract: A family of diphenylic esters are disclosed, which, within certain temperature ranges exhibit mesomorphic phases, either smectic or nematic, having the general formula: ##STR1## where R.sub.1 is C.sub.n H.sub.2n+1 O or C.sub.n H.sub.2n+1 in which n is an integer of from 1 to 10,R.sub.2 is C.sub.m H.sub.2m+1 in which m is an integer of from 1 to 10, andX is Br or CN.
    Type: Grant
    Filed: April 12, 1979
    Date of Patent: November 25, 1980
    Assignee: Thomson-CSF
    Inventors: Alain Beguin, Jean-Claude Dubois, Annie Zann
  • Patent number: 4227009
    Abstract: Phenoxyphenoxy-propionic acid derivatives of the formula ##STR1## exhibit an outstanding herbicidal activity against a wide variety of weed grasses and are well tolerated by dicotyledonous crop plants and various cereals.
    Type: Grant
    Filed: May 24, 1977
    Date of Patent: October 7, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Koch, Reinhard Handte, Gerhard Horlein, Heinrich Leditschke, Helmut Kocher, Peter Langeluddeke
  • Patent number: 4227015
    Abstract: 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. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.
    Type: Grant
    Filed: February 14, 1979
    Date of Patent: October 7, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Joseph C. Collins
  • Patent number: 4227019
    Abstract: 11-Substituted prostaglandins E.sub.1, E.sub.2 and F.sub.2.alpha. useful as cardiovascular agents and as agents for inducing labor in pregnant females and for the termination of pregnancy and a process for preparing these prostaglandins.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: October 7, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
  • Patent number: 4225533
    Abstract: Novel esters of ether and thioether substituted cyclopropanecarboxylic acids, synthesis thereof, and intermediates therefor, such esters being useful as pesticides.
    Type: Grant
    Filed: June 1, 1979
    Date of Patent: September 30, 1980
    Assignee: Zoecon Corporation
    Inventor: Clive A. Henrick
  • 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: 4216172
    Abstract: A process for the preparation of a cyclobutanone of the formula ##STR1## in which R.sup.1 to R.sup.6 each independently is a hydrogen, halogen, cyano, alkoxy, alkoxycarbonyl, carboxamido, dialkylphosphono, alkyl, cycloalkyl, aryl, aralkyl or alkenyl radical, or two of them together with the carbon atom to which each is linked form a ring,comprising reacting an N,N-disubstituted carboxylic acid amide of the formula ##STR2## in which R.sup.7 and R.sup.8 each independently is an alkyl, cycloalkyl, alkenyl, aryl or aralkyl radical or together form a ring, with an inorganic acid halide, and then reacting the product with a tertiary amine, an olefin of the formula ##STR3## and a Lewis acid, and subsequently hydrolyzing the mass. Preferably isobutyric acid dimethylamide is employed as the carboxylic acid amide, phosgene is employed as the inorganic acid halide, triethylamine is employed as the tertiary amine and zinc chloride or titanium tetrachloride is employed as the Lewis acid.
    Type: Grant
    Filed: March 13, 1978
    Date of Patent: August 5, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Georg Heine, Willy Hartmann
  • 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: 4201787
    Abstract: Isovaleric acid ester derivatives, process for producing thereof, and insecticides containing said derivatives of the general formula I: ##STR1## wherein A represents O, NH, or CH.sub.2,R.sub.1 represents, if A is O or NH, an alkyl, an alkenyl, a haloalkyl and a haloalkenyl radical with 2-6 carbon atoms, and a radical selected from those of the general formulae II, III, IV and V: ##STR2## in which n is an integer of 1-3, R.sub.3 represents hydrogen, methyl group or chlorine atom; andif A is CH.sub.2, R.sub.1 represents an alkyl, an alkenyl, a haloalkyl and a haloalkenyl radical with 1-5 carbon atoms, whileR.sub.1 --A represents a naphthyl group bonding to the main chain at the .beta.-position, andR.sub.2 represents hydrogen or a cyano group.
    Type: Grant
    Filed: November 30, 1977
    Date of Patent: May 6, 1980
    Assignee: Dainippon Jochugiku Kabushiki Kaisha
    Inventors: Yoshio Katsuda, Yoshihiro Minamite
  • 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