Halogen Attached Directly Or Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/303)
  • Patent number: 4251663
    Abstract: 3-Trifluorothiomethyl-2-(3-loweralkylamino-2-R.sub.1 O-propoxy)pyridines, their pharmaceutically acceptable salts certain intermediates and their preparation are disclosed. These pyridines have pharmaceutical properties such as antihypertensive activity of rapid onset.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: February 17, 1981
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Gerald S. Ponticello
  • Patent number: 4249009
    Abstract: One process comprises the step of reacting an amount of 5-carboxy-2-pyridone directly with both a suitable chlorinating agent and a suitable fluorinating agent to selectively transform both the 5-carboxy group and the 2-positioned oxygen function of the ring. A second process comprises the steps of reacting an amount of 5-carboxy-2-pyridone with a suitable fluorinating agent to selectively transform the 5-carboxy group without altering the 2-positioned oxygen function of the ring and reacting the 5-trifluoromethyl-2-pyridone thereby formed with a suitable chlorinating agent to cause 2-chloro-5-trifluoromethylpyridine to form.
    Type: Grant
    Filed: January 29, 1979
    Date of Patent: February 3, 1981
    Assignee: Reilly Tar & Chemical Corp.
    Inventor: Thomas D. Bailey
  • Patent number: 4236009
    Abstract: 4a-Arylhexahydro-1H-2-pyrindines and 4a-aryloctahydroquinolines analgesic agonists and antagonists are prepared doubly alkylating a 4-aryltetrahydropyridine with an .alpha.,.omega.-dihaloalkane.
    Type: Grant
    Filed: June 21, 1979
    Date of Patent: November 25, 1980
    Assignee: Eli Lilly and Company
    Inventors: Dennis M. Zimmerman, Roger L. Robey
  • Patent number: 4234590
    Abstract: 3-Trifluoromethylthio-2-(3-loweralkylamino-2-R.sub.1 O-propoxy)pyridines, their pharmaceutically acceptable salts certain intermediates and their preparation are disclosed. These pyridines have pharmaceutical properties such as antihypertensive activity of rapid onset.
    Type: Grant
    Filed: February 5, 1979
    Date of Patent: November 18, 1980
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Gerald S. Ponticello
  • 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: 4230864
    Abstract: The chemical compound 5-trifluoromethyl-2-pyrone and a process for preparing a 5-trifluoromethyl-2-oxy compound of the formula ##STR1## wherein A is oxygen or nitrogen bearing a hydrogen, comprising the step of reacting an amount of the 5-carboxy precursor of the compound with a suitable fluorinating agent to selectively transform the 5-carboxy group without altering the oxygen function in the 2-position of the ring.
    Type: Grant
    Filed: January 29, 1979
    Date of Patent: October 28, 1980
    Assignee: Reilly Tar & Chemical Corp.
    Inventor: Thomas D. Bailey
  • Patent number: 4228085
    Abstract: The present invention relates to a novel organic compound, phenyl alpha,beta-epoxy-beta-(3-trifluoromethylphenyl)ethyl ketone. This compound may be produced by:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone, and(b) epoxidation of the substituted chalcone to produce the corresponding epoxide, phenyl alpha,beta-epoxy-beta-(3-trifluoromethylphenyl)ethyl ketone.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: October 14, 1980
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4218237
    Abstract: A sulfonanilide compounds having the formula (I): ##STR1## wherein X.sub.1 is hydrogen atom, a halogen atom, methyl group or trifluoromethyl group, X.sub.2 is hydrogen atom or a halogen atom, R.sub.1 is a (C.sub.1 -C.sub.4) alkyl group or a halo(C.sub.1 -C.sub.4) alkyl group, R.sub.2 is hydrogen atom, a (C.sub.1 -C.sub.4) alkyl group, trifluoromethyl group or nitro group, R.sub.3 is hydrogen atom, --SO.sub.2 R.sub.1 group (R.sub.1 is the same as defined above), a (C.sub.2 -C.sub.4) acyl group, a (C.sub.2 -C.sub.4) acylmethyl group, a (C.sub.1 -C.sub.4) alkyl group, a (C.sub.1 -C.sub.4) alkoxy (C.sub.1 -C.sub.4) alkyl group or a (C.sub.3 -C.sub.4) alkenyl group, R.sub.4 is hydrogen atom or a halogen atom, and n is an integer of 0 to 2; and a salt thereof, which is useful as a herbicidal component.
    Type: Grant
    Filed: November 17, 1978
    Date of Patent: August 19, 1980
    Assignee: Ishihara Sangyo Kaisha Limited
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Fumio Kimura, Rikuo Nasu, Nobuyuki Sakashita, Shigeyuki Nishimura
  • Patent number: 4218238
    Abstract: A class of 1-alkyl-3-phenylpyridinium salts are useful herbicides. The compounds bear a meta-substituent on the phenyl ring and optional 4- and 5-substituents.
    Type: Grant
    Filed: June 20, 1979
    Date of Patent: August 19, 1980
    Assignee: Eli Lilly and Company
    Inventors: Harold M. Taylor, Robert G. Suhr
  • Patent number: 4191831
    Abstract: Imidazolylethoxy derivatives of pyridin-5-methanols having the general formula ##STR1## and their acid addition salts are useful as antifungal and antibacterial agents.
    Type: Grant
    Filed: October 25, 1978
    Date of Patent: March 4, 1980
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Hans Hoehn
  • Patent number: 4190662
    Abstract: Compounds are prepared which correspond to the formula ##STR1## wherein X and Y represent OR', trichloromethyl, trifluoromethyl, dichloromethyl, dichlorofluoromethyl or chlorodifluoromethyl with the proviso that one of X or Y must be OR' and the other of X and Y is other than OR'; and R and R' each independently represent alkyl of 1 to 12 carbons or alkenyl of 3 or 4 carbon atoms. These compounds and compositions containing them have been found to be useful as agronomic fungicides, especially useful and valuable for the control of soil-borne plant disease organisms which attack the roots of plants.
    Type: Grant
    Filed: March 23, 1978
    Date of Patent: February 26, 1980
    Assignee: The Dow Chemical Company
    Inventors: Myk R. Fenstermacher, Robert L. Noveroske
  • Patent number: 4185106
    Abstract: A cosmetic composition comprising a content of an 1-hydroxy-2-pyridone of the general formula ##STR1## in which R.sub.1 stands for hydrogen, alkyl of 1 to 17 carbon atoms, alkenyl of 2 to 17 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, bicycloalkyl of 7 to 9 carbon atoms, cycloalkyl-alkyl of 1 to 4 alkyl carbon atoms, the cycloalkyl groups being optionally substituted by alkyl groups of 1 to 4 carbon atoms, aryl, aralkyl of 1 to 4 alkyl carbon atoms, aryl-alkenyl of 2 to 4 alkenyl carbon atoms, aryloxy-alkyl or arylthio-alkyl of 1 to 4 alkyl carbon atoms, benzhydryl, phenylsulfonyl-alkyl of 1 to 4 alkyl carbon atoms, furyl or furyl-alkenyl of 2 to 4 alkenyl carbon atoms, the aryl groups being optionally substituted by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms, by nitro, cyano or halogen atoms, R.sub.2 stands for hydrogen, alkyl of 1 to 4 carbon atoms, alkenyl or alkinyl of 2 to 4 carbon atoms, halogen atoms or benzyl, R.sub.
    Type: Grant
    Filed: August 15, 1975
    Date of Patent: January 22, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Walter Dittmar, Eberhard Futterer, Gerhard Lohaus
  • Patent number: 4174209
    Abstract: A class of 1-alkyl-3-phenylpyridinium salts are useful herbicides. The compounds bear a meta-substituent on the phenyl ring and optional 4- and 5-substituents.
    Type: Grant
    Filed: June 19, 1978
    Date of Patent: November 13, 1979
    Assignee: Eli Lilly and Company
    Inventors: Harold M. Taylor, Robert G. Suhr
  • Patent number: 4170704
    Abstract: Novel iodopropargyl pyridyl and picolinyl ethers and thioethers are effective antifungal agents. They find special utility in paint for protecting finished paint films from fungal attack.
    Type: Grant
    Filed: April 20, 1978
    Date of Patent: October 9, 1979
    Assignee: Givaudan Corporation
    Inventors: Harold A. Brandman, Joachim E. Freudewald, Milton Manowitz, Edward J. Nikawitz, Frederick H. Sharpell, Jr.
  • Patent number: 4154834
    Abstract: The compounds are substituted isocytosines which are histamine H.sub.2 -antagonists. Two specific compounds of the present inventon are 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-py rimidone and 2-[2-(3-bromo-2-pyridylmethylthio)ethylamino]-5-(4-pyridylmethyl)-4-pyrimi done.
    Type: Grant
    Filed: December 16, 1977
    Date of Patent: May 15, 1979
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Thomas H. Brown, Graham J. Durant, Charon R. Ganellin
  • Patent number: 4153235
    Abstract: Compounds possessing hypoglycemic, hypotensive, anti-inflammatory, anticoagulant and diuretic acitivity are represented by compounds of the following formula ##STR1## wherein Y is thienyl, cycloalkyl of from 5 to 7 carbon atoms, phenyl or substituted phenyl in which case the substituents on the substituted phenyl are selected from halogen, such as fluorine, chlorine, bromine or iodine, lower alkyl of from 1 to 4 carbon atoms and lower alkoxy of from 1 to 4 carbon atoms; Z is hydrogen or hydroxy; R is hydrogen, lower alkyl of from 1 to 4 carbon atoms, phenyl or benzyl; R.sup.1 is hydrogen, lower alkyl of from 1 to 4 carbon atoms or halogen, such as chlorine, fluorine, bromine or iodine; m is from 3 to 6; and n is from 3 to 11. Pharmaceutical compositions of these compounds and their use are also disclosed.
    Type: Grant
    Filed: February 14, 1978
    Date of Patent: May 8, 1979
    Assignee: Richardson-Merrell Inc.
    Inventors: Johann M. Grisar, Thomas R. Blohm, Edward M. Roberts
  • Patent number: 4152136
    Abstract: A class of 3-phenyl-4(1H)-pyridones and pyridinethiones are broad-spectrum herbicides. The new compounds are characterized by a small substituent on the nitrogen, and usually bear a 5-substituent chosen from a class described herein. The phenyl ring may be substituted. The compounds are effective herbicides when applied both before and after the emergence of weeds, and are particularly useful for the control of weeds in cotton and rice cropland.
    Type: Grant
    Filed: June 27, 1977
    Date of Patent: May 1, 1979
    Assignee: Eli Lilly and Company
    Inventor: Harold M. Taylor
  • Patent number: 4144239
    Abstract: An industrially advantageous process for the manufacture of vitamin B6 (pyridoxin) from 2-methyl-3-hydroxy-4,5-bis-(halomethyl)-pyridine, wherein the starting compound is first converted in the conventional manner to the corresponding pure acetoxy compound which is reacted with an alkali metal acetate, alkaline earth metal acetate or tertiary ammonium acetate to give pyridoxin triacetate, from which pyridoxin can be liberated by hydrolysis or trans-esterification.
    Type: Grant
    Filed: April 14, 1978
    Date of Patent: March 13, 1979
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Boell, Horst Koenig
  • Patent number: 4138488
    Abstract: Disclosed herein are substituted diphenylmethyl picolinic acids, pharmaceutically acceptable salts, amides and esters thereof. The compounds disclosed are useful as topical anti-acne agents.
    Type: Grant
    Filed: January 10, 1977
    Date of Patent: February 6, 1979
    Assignee: Schering Corporation
    Inventors: Margaret H. Sherlock, Heide Roebke
  • Patent number: 4128552
    Abstract: Diphenylbutyltetrahydropyridines of the following formula: ##STR1## are disclosed, in which X is hydrogen, halogen such as fluorine, chlorine or bromine, trifluoromethyl, alkoxy, nitro, amino, lower alkyl of 1 to 6 carbon atoms, aryl or substituted aryl and n is 0, 1 or 2. These compounds are useful as antipsychotics.
    Type: Grant
    Filed: September 26, 1977
    Date of Patent: December 5, 1978
    Assignee: Warner-Lambert Company
    Inventors: Lawrence D. Wise, Patrick F. Flynn, Glenn C. Morrison
  • Patent number: 4127582
    Abstract: A novel method for the preparation of alkyl halopyridinyloxyalkanoate compounds is disclosed, which comprises reacting a halopyridine with an alkyl alpha-hydroxy alkanoate in the presence of an alkali metal carbonate promoter.The ester products prepared from this method are useful as herbicides.
    Type: Grant
    Filed: December 27, 1976
    Date of Patent: November 28, 1978
    Assignee: The Dow Chemical Company
    Inventor: Leo R. Morris