Oxy, Bonded Directly To A Ring, In Same Side Chain As Carboxyl, Or Salt Thereof Patents (Class 562/471)
  • Patent number: 4291050
    Abstract: This invention relates to a new class of chemical compounds which can be described generally as 6,7-disubstituted-2 or 2,2-substituted-5-substituted-1-indanones. These compounds are effective diuretic and saluretic agents.
    Type: Grant
    Filed: June 21, 1979
    Date of Patent: September 22, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Otto W. Woltersdorf, Jr., Edward J. Cragoe, 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: 4277619
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-inter-phenylene-13,14-dihydro-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: July 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4273784
    Abstract: The present invention concerns prostaglandins having a cyclopropane ring in the 2,3 position.
    Type: Grant
    Filed: March 28, 1979
    Date of Patent: June 16, 1981
    Assignee: Sandoz Ltd.
    Inventor: Pietro Bollinger
  • Patent number: 4267317
    Abstract: A phenoxyalkene derivative having the formula ##STR1## wherein R represents a hydrogen atom, ##STR2## and Y and Z are the same or different and respectively represent a hydrogen atom, trifluoromethyl group, a halogen atom, a lower alkyl group, nitro group or cyano group; R.sub.1 represents a hydrogen atom or a lower alkyl group and R.sub.2 represents carboxyl, hydroxymethyl, allyloxycarbonyl, a lower alkoxycarbonyl, a lower haloalkoxycarbonyl, a S-lower alkylthiocarbonyl, carbamoyl, a N-lower alkylcarbamoyl or a N-phenylcarbamoyl group is produced by reacting a phenol compound having the formula ##STR3## with a dihalogen compound having the formula ##STR4## wherein R, R.sub.1 and R.sub.2 are defined above and X.sub.1 represents a halogen atom and X.sub.2 and X.sub.
    Type: Grant
    Filed: October 12, 1979
    Date of Patent: May 12, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Wataro Koike, Tadashi Sasuga, Chihiro Yazawa
  • Patent number: 4259523
    Abstract: This invention provides new mono-deuterated prostaglandins having prolonged uterotonic activity.
    Type: Grant
    Filed: May 11, 1979
    Date of Patent: March 31, 1981
    Assignee: Sandoz Ltd.
    Inventors: Pietro Bollingen, Manfred Krieger
  • Patent number: 4254262
    Abstract: A phenoxycarboxylic acid derivative having the formula ##STR1## wherein R represents ##STR2## and X.sub.1 represents a hydrogen atom, a halogen atom, a lower alkyl group, trifluoromethyl group, nitro group or cyano group and X.sub.2 represents a hydrogen atom, a halogen atom, a lower alkyl group, nitro group or cyano group, R' represents ##STR3## and R.sub.1 and R.sub.2 are the same and different and respectively represent hydrogen atom or a lower alkyl group, is produced by reacting a phenol compound having the formula ##STR4## with a halogen compound havingX--R'wherein X represents a halogen atom in the presence of a base. The reaction is carried out in the presence of a quarternary ammonium salt or a quaternary phosphonium salt in a nonpolar solvent.
    Type: Grant
    Filed: October 12, 1979
    Date of Patent: March 3, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Wataro Koike, Tadashi Sasuga, Chihiro Yazawa
  • Patent number: 4252624
    Abstract: m-(.alpha.-Bromoethyl)diphenyl ether is prepared by a free radical bromination of m-ethyldiphenyl ether.
    Type: Grant
    Filed: April 24, 1979
    Date of Patent: February 24, 1981
    Assignee: Eli Lilly and Company
    Inventor: Erwin A. Stephan
  • 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: 4229363
    Abstract: New 4-hydroxy-3-(substitutedmethyl)benzeneacetic acids have been prepared which are useful as starting materials in the preparation of cephalosporin and penicillin derivatives.
    Type: Grant
    Filed: September 7, 1978
    Date of Patent: October 21, 1980
    Assignee: Yeda Research and Development Co., Ltd.
    Inventors: Abraham Nudelman, Abraham Patchornik
  • Patent number: 4221725
    Abstract: Radiolabeled steroid derivatives having the formula ##STR1## wherein St is des-hydroxy steroid moiety of (i) a hydroxy steroid intended for radioimmunoassay or (ii) a hydroxy containing derivative of a steroid intended for radioimmunoassay, said derivative having a strong affinity for the antibodies of the steroid intended for radioimmunoassay; R is hydrogen or alkyl of 1 to 3 carbon atoms; n is 0, 1, 2, 3 or 4 and the asterisk (*) indicates tagging with a radioisotope, are useful as tracers in radioimmunoassays.
    Type: Grant
    Filed: January 17, 1979
    Date of Patent: September 9, 1980
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jack Bernstein, Ravi K. Varma, B. Richard Vogt, Frank L. Weisenborn
  • 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: 4214086
    Abstract: A process for producing hydroxydiaryl ethers of the formula ##STR1## wherein R respesents an alkyl group having 1 to 4 carbon atoms or chlorine, n represents 0, 1, 2, 3 or 4, and X represents a phenyl group of the formula II ##STR2## or a 2-pyridinyl group or a 4-pyridinyl group of the formulae ##STR3## wherein R.sub.1, R.sub.2 and R.sub.3 each represent hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkyl group which has 1 to 4 carbon atoms and which is mono- or disubstituted by halogen, phenyl, halogen, carboxyl, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl group, trifluoromethyl, nitro, cyano or benzoyl, R.sub.4 and R.sub.5 each represent hydrogen, an alkyl group having 1 to 4 carbon atoms or phenyl, and R.sub.6 has all the meanings given, with the exception of halogen, for R.sub.1, R.sub.2 and R.sub.3 is disclosed.
    Type: Grant
    Filed: May 9, 1979
    Date of Patent: July 22, 1980
    Assignee: Ciba-Geigy Corporation
    Inventor: Hansjakob Fah
  • 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: 4204001
    Abstract: The disclosure relates to .omega.-aryl substituted .omega.-nor prostaglandin analogues bearing an oxygenated function at C-10, such as a hydroxy radical, or a 9,10- or 10,11-epoxide. A typical compound is 16-(3-chlorophenoxy)-9.alpha.,10.beta.,11.alpha.,15.alpha.-tetrahydroxy-17 ,18,19,20-tetranor-5-cis,13-trans-prostadienoic acid. Also disclosed are chemical processes for the manufacture of said compounds, pharmaceutical and veterinary compositions containing said compounds, and a method of achieving luteolysis in mammals by the use of such compounds.
    Type: Grant
    Filed: May 30, 1978
    Date of Patent: May 20, 1980
    Assignee: Imperial Chemical Industries Limited
    Inventors: Jean Bowler, Graham E. Robinson
  • 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: 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: 4198430
    Abstract: Optionally active 13,14-dehydro-11-deoxy prostaglandins useful in inhibiting gastric secretions and as anti-asmthmatic agents are disclosed.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: April 15, 1980
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Carmelo Gandolfi, Renato Pellegate, Franco Faustini, Angelo Fumagalli
  • 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: 4198525
    Abstract: The present invention relates to two novel compounds, the pharmacologically acceptable salts thereof and their preparation and use as pharmacological agents. These novel compounds are11-deoxy-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-PGE.sub.1 and11-deoxy-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-13,14-dihydro-PGE.sub.1.
    Type: Grant
    Filed: January 15, 1979
    Date of Patent: April 15, 1980
    Assignee: The Upjohn Company
    Inventor: Douglas R. Morton, 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: 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: 4175209
    Abstract: A process, and intermediates for the preparation of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid are described. The acid possesses antiinflammatory and analgesic activity.
    Type: Grant
    Filed: September 5, 1978
    Date of Patent: November 20, 1979
    Assignee: American Hoechst Corporation
    Inventors: Arthur R. McFadden, Richard C. Allen, Thomas B. K. Lee
  • Patent number: 4174306
    Abstract: Detergent compositions containing self-requestering surfactants the molecules of which contain both a hydrophilic structure and a lipophilic structure are disclosed. The compositions comprise at least 5% by weight, of hydrosoluble salts having the formula ##STR1## in which R is alkyl, arylalkyl or alkylaryl of from 6 to 18 carbon atoms;at least one of the groups represented by Z is a --CH.sub.2 --COO.sup.- Me.sup.+ carboxymethylene group in which Me.sup.+ represents an ion selected from sodium, potassium and ammonium ions and from quaternary onium cations, and combinations thereof, and the remaining Z groups, which may be the same or different, represent H or a carboxymethylene as defined above.
    Type: Grant
    Filed: February 27, 1978
    Date of Patent: November 13, 1979
    Assignee: Montedison S.p.A.
    Inventors: Salvatore Gafa, Fulvio Burzio
  • 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: 4163107
    Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is of the cis configuration. 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: May 8, 1978
    Date of Patent: July 31, 1979
    Assignee: The Upjohn Company
    Inventor: Ernest W. Yankee
  • Patent number: 4160106
    Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is of the cis configuration. 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: May 8, 1978
    Date of Patent: July 3, 1979
    Assignee: The Upjohn Company
    Inventor: Ernest W. Yankee
  • 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: 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: 4118420
    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: March 25, 1976
    Date of Patent: October 3, 1978
    Assignee: Monsanto Company
    Inventor: Kent P. Lannert
  • 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