Oxy Patents (Class 562/463)
  • Patent number: 4675421
    Abstract: Compound of the general formula ##STR1## wherein R represents an ether protecting group useful as intermediates.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: June 23, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Barner, Josef Hubscher
  • Patent number: 4670581
    Abstract: New biphenyl compounds and a process for producing them are provided. These new compounds have an acyloxy group in the 2- or 4-position of the biphenyl and an acyl hydroxyalkyl, hydroxyalkenyl or vinyl group in the 4'-position of the biphenyl or, alternatively a hydroxyl group in the 2- or 4-position of the biphenyl and an acyl, hydroxyalkyl, hydroxyalkenyl or vinyl group in the 4'-position of the biphenyl. These compounds can be produced easily from 2- or 4-acyloxybiphenyl compounds.
    Type: Grant
    Filed: January 10, 1984
    Date of Patent: June 2, 1987
    Assignee: Sugai Chemical Industry Co., Ltd.
    Inventor: Teiichi Tanigaki
  • Patent number: 4670585
    Abstract: 2-Carboxydibenzoylmethanes of the following formula ##STR1## in which R.sub.1 and R.sub.2 are independently a substituent joined to any position of the benzene nucleus and represent a hydrogen atom, a halogen atom, a linear or branched alkyl or alkenyl group having from 1 to 18 carbon atoms, or a linear or branched, saturated or unsaturated alkoxy group having from 1 to 18 carbon atoms, m is an integer of from 1 to 4, and n is an integer of from 1 to 5 are prepared inexpensively with ease in high yield by a novel process characterized by reaction between phthalic anhydrides and acetophenones in the presence of bases.The 2-carboxydibenzoylmethanes are useful as an inhibitor of the root geotropic response of plants or a growth regulator for plants, or a stabilizer for halogen-containing resins.
    Type: Grant
    Filed: August 21, 1986
    Date of Patent: June 2, 1987
    Assignee: Kao Corporation
    Inventors: Kimihiko Hori, Koichi Nakamura, Naotake Takaishi
  • Patent number: 4667055
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 E.sub.4 and the slow reacting substance of anaphylaxis.As such, these compounds will be useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.
    Type: Grant
    Filed: March 20, 1985
    Date of Patent: May 19, 1987
    Assignee: Merck Frosst Canada, Inc.
    Inventors: John Gillard, Joshua Rokach, Patrice C. Belanger
  • Patent number: 4647413
    Abstract: Perfluoropolyether oligomers or block polymers, having a backbone with one or a plurality of perfluoropolyether segments each consisting essentially of (1) at least one perfluoroisopropyleneoxy unit, (2) a bis(perfluoromethyleneoxy-terminated) unit, and (3) a perfluoroethylidene unit terminating each segment, the backbone of the perfluoropolyether being terminated with COF and/or a functional or nonfunctional derivative thereof, said perfluoropolyethers being made by reacting a perfluoroaliphatic diacid fluoride with hexafluoropropylene epoxide to produce an acid fluoride-terminated perfluoropolyether adduct or oligomer which then can be photopolymerized to yield an acid fluoride-terminated perfluoropolyether block polymer. These oligomers and block polymers are useful as high temperature lubricants, hydraulic fluids, gaskets, adhesives and coatings as well as co-reactants wtih urethane in forming propellant binders.
    Type: Grant
    Filed: January 20, 1984
    Date of Patent: March 3, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Patricia M. Savu
  • Patent number: 4626597
    Abstract: 16-Fluoro-16,17-didehydro prostanoids, processes for their preparation, compositions containing them and methods of using them are disclosed. The compounds and compositions have pharmaceutical utility including, for example, luteolytic activity.
    Type: Grant
    Filed: August 22, 1984
    Date of Patent: December 2, 1986
    Assignee: Farmitalia Carlo Erba, S.p.A.
    Inventors: Franco Faustini, Roberto d'Alessio, Achille Panzeri, Enrico di Salle
  • Patent number: 4625047
    Abstract: The invention relates to novel substituted [2,3-dihydro-4-(3-oxo-1-cyclohexen-1-yl)phenoxy]-alkanoic acids their derivatives and their salts. The compounds are useful for the treatment and prevention of injury to the brain and of edema due to head trauma, stroke (particularly ischemic), arrested breathing, cardiac arrest, Reye's syndrome, cerebral thrombosis, cerebral embolism, cerebral hemorrhage, cerebral tumors, encephalomyelitis, spinal cord injury, hydrocephalus, post-operative brain injury trauma, edema due to cerebral infections and various brain concussions.
    Type: Grant
    Filed: December 23, 1985
    Date of Patent: November 25, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Adolph M. Pietruszkiewicz, Otto W. Woltersdorf, Jr.
  • Patent number: 4596883
    Abstract: The invention relates to certain herbicidally active substituted diphenyl ether derivatives, herbicidal compositions of the same and the use thereof for preemergence and postemergence control of noxious plants, i.e., weeds.
    Type: Grant
    Filed: July 5, 1984
    Date of Patent: June 24, 1986
    Assignee: PPG Industries, Inc.
    Inventors: James A. Schwindeman, Horng-Jau Lin
  • Patent number: 4594443
    Abstract: Compounds of the formula (I): ##STR1## in which R.sub.1 represents alkyl containing from 1 to 18 carbon atoms, R.sub.2 represents hydrogen or alkyl containing from 1 to 8 carbon atoms and R represents hydrogen or alkyl containing from 1 to 8 carbon atoms, as well as the alkali metal, alkaline-earth metal or amine salts thereof, in which R represents hydrogen. Also, method of preparing same, compositions containing same and therapeutic treatment therewith.
    Type: Grant
    Filed: August 20, 1984
    Date of Patent: June 10, 1986
    Assignee: Roussel-Uclaf
    Inventors: Mario Bianchi, Fernando Barzaghi
  • Patent number: 4582857
    Abstract: P-oxybenzoic acid derivatives of formula (1) ##STR1## wherein R.sup.1 is hydrogen, or straight or branched alkyl of one to four carbon atoms;n is 1 or 2;X is ##STR2## and R.sup.2 is --OH or --NHCH.sub.2 COOH; and non-toxic pharmaceutically acceptable salts thereof.The compounds exhibit a hypolipemic effect. They may be prepared by methods known in themselves from the corresponding ester or acid halide compounds, wherein optionally the secondary alcohol group may be oxidized to a keto group.
    Type: Grant
    Filed: July 20, 1984
    Date of Patent: April 15, 1986
    Assignee: Klinge Pharma GmbH
    Inventors: Helmut Grill, Friedemann Reiter, Roland Loser, Michael Schliack, Klaus Seibel
  • Patent number: 4578505
    Abstract: This invention relates to novel allenic prostanoic acid derivatives having the following formula ##STR1## wherein R is hydrogen; or straight or branched chain alkyl of 1 to 6 carbon atoms, inclusivewherein R.sub.1 is hydrogen; or straight or branched chain alkyl of 1 to 6 carbon atoms, inclusive; or vinyl (--CH.dbd.CH.sub.2)wherein R.sub.2 is straight or branched chain alkyl of 1 to 6 carbon atoms; or cycloalkyl group containing 3 to 6 carbon atoms; or phenyl; or phenoxywherein R.sub.3 is hydrogen; or straight chain alkyl of 1 to 3 carbon atomswherein m is an integer of from 1 to 4, inclusive,wherein n is an integer of from 1 to 3, inclusive with the proviso that the sum of m and n does not exceed 5,wherein y is an integer of from 1 to 3.These compounds are useful by reason of their gastric antisecretory and cytoprotective activity.
    Type: Grant
    Filed: September 4, 1984
    Date of Patent: March 25, 1986
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Richard M. Weier
  • Patent number: 4567201
    Abstract: A diphenoxypropane derivative of the formula: ##STR1## wherein X is a halogen atom, Y is a hydrogen atom or a hydroxy group and Z is a tetrazolyl or carboxy group, has excellent antiasthmatic and antiinflammatory activities, and therefore the diphenoxypropane derivatives are useful as antiasthmatic or antiinflammatory agents.
    Type: Grant
    Filed: November 9, 1982
    Date of Patent: January 28, 1986
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akira Nohara, Yoshitaka Maki
  • Patent number: 4562204
    Abstract: Trans-.DELTA..sup.2 -prostaglandin D derivatives of the formula: ##STR1## wherein [A] is a group of the formula: ##STR2## X is ethylene or cis-vinylene, C.sub.13 -C.sub.14 -C.sub.15 is: (i) a group of the formula: ##STR3## when [A] is a group of the formula (II) or (III), or (ii) a group of the formula: ##STR4## when [A] is a group of the formula (IV), R is hydrogen or alkyl, R.sup.1 is a single bond or alkylene, R.sup.2 is alkyl, cycloalkyl, phenyl or phenoxy, the double bonds between C.sub.2 -C.sub.3 and between C.sub.13 -C.sub.14 are both E, the double bond between C.sub.9 -C.sub.10 is Z and the double bonds between C.sub.12 -C.sub.13 and between C.sub.14 -C.sub.15 are E, Z or a mixture thereof, provided that when R.sup.1 is a single bond, R.sup.2 does not represent a substituted or unsubstituted phenoxy group, and cyclodextrin clathrates and non-toxic salts thereof, possess anti-tumor activity.
    Type: Grant
    Filed: June 28, 1983
    Date of Patent: December 31, 1985
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Hirohisa Wakatsuka, Takashi Yamato, Shinsuke Hashimoto
  • Patent number: 4560403
    Abstract: As new compound is provided a cyclohexane derivative of the formula ##STR1## wherein R represents a hydrogen atom or an alkyl group, an alkylthioalkyl group or an unsubstituted or substituted phenyl group; and R.sup.1 represents an alkyl group, an unsubstituted or substituted benzyl group, a phenethyl group, a phenoxymethyl group, a 2-thienylmethyl group, an alkoxymethyl group or an alkylthiomethyl group, or a salt of said cyclohexane compound.This cyclohexane compound exhibits useful plant-growth regulating effects on crop-plants and also non-crop plants such as lawn and may be prepared by cyclization of an acetonylsuccinic acid dialkyl ester, followed by reaction with an organic acid chloride and by intermolecular rearrangement.
    Type: Grant
    Filed: September 22, 1983
    Date of Patent: December 24, 1985
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
  • Patent number: 4544565
    Abstract: Foodstuffs containing sweetness inhibitors having the general formula: ##STR1## wherein R.sub.7 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.3 alkyl, R.sub.8 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.3 alkyl and wherein R.sub.9 is the group ##STR2## wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 hydroxyalkyl, hydroxy and COOH; and the non-toxic salts thereof.
    Type: Grant
    Filed: March 29, 1984
    Date of Patent: October 1, 1985
    Assignee: General Foods Corporation
    Inventor: Ronald E. Barnett
  • Patent number: 4542233
    Abstract: Improvement in the process for preparing biaryl compounds via coupling of an arylamine with an arene in the presence of a nitrite, an acid and copper metal or a derivative thereof; the improvement is consisting in adding to the reaction mixture a trialkylorthoformate. The process may be used for preparing drugs such as Flurbiprofen and Xenbucin or intermediate compounds particularly useful for preparing Flurbiprofen, Flufenisal, Chlordimorin, Xenbucin, Xenysalate, Xenyhexenic acid and the like.
    Type: Grant
    Filed: July 20, 1983
    Date of Patent: September 17, 1985
    Assignee: Biaschim S.p.A.
    Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio
  • Patent number: 4536592
    Abstract: The present invention encompasses 16-alkyl, 16-hydroxy-2-substituted prostaglandins which exhibit cytoprotective and antisecretory activity with greatly reduced diarrhea side effects.
    Type: Grant
    Filed: February 16, 1984
    Date of Patent: August 20, 1985
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Alan F. Gasiecki, Richard M. Weier
  • Patent number: 4535183
    Abstract: This invention is directed to novel ether compounds of formula (I) ##STR1## which are of value in medicine in the palliation of haemoglobinopathies, in particular sickle-cell anemia, and also in the palliation of pulmonary dyefunction, protection from the effects of hypoxia and the radio-sensitization of tumours. The invention is also directed to methods for the preparation of the ether compounds, to pharmaceutical formulations containing them, the preparation of such formulations and the use of the compounds in human medicine. Also provided by the invention are intermediates of value in the preparation of the ether compounds, by the methods described, and the preparation of the intermediates.
    Type: Grant
    Filed: December 18, 1981
    Date of Patent: August 13, 1985
    Assignee: Burroughs Wellcome Co.
    Inventor: Geoffrey Kneen
  • Patent number: 4533732
    Abstract: This invention relates to derivatives of 3-propionylsalicylic acid represented by the formula (1) ##STR1## wherein R represents a hydrogen atom, a lower alkyl group or a group ##STR2## (wherein R.sup.1 and R.sup.2 represent a lower alkyl group or R.sup.1 and R.sup.2, when taken together with the nitrogen atom to which they are attached, may form a heterocyclic ring with or without an intervening hetero atom, and n is an integer of 1 to 4), and X represents a hydrogen atom or a halogen atom, R being the group ##STR3## when X is a hydrogen atom. This invention also relates to processes for preparing the same.
    Type: Grant
    Filed: September 30, 1983
    Date of Patent: August 6, 1985
    Assignees: Yamamoto Chemical Industrial Company, Limited, Osaka Municipal Government
    Inventors: Hiroshige Inoue, Kenichi Fukushima, Ikuzo Nishiguchi
  • Patent number: 4528371
    Abstract: A process for preparing 6-(2-hydroxyphenyl)-3-pyridazinone which comprises reacting 2-hydroxyacetophenone with glyoxylic acid under alkaline conditions, adjusting the pH of the reaction mixture to give a mixture within a pH range of about pH 4.0-9.5 and which contains a weak base, and subsequently reacting with hydrazine.6-(2-Hydroxyphenyl)-3-pyridazinone is a useful intermediate in the preparation of anti-hypertensive agents.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: July 9, 1985
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: William J. Coates, Brian H. Warrington
  • Patent number: 4507498
    Abstract: Phenoxycarboxylic acids of the formula ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, Z and n are as hereinafter set forth, are as described. The compounds of formula I are antagonists of slow reacting substance of anaphylaxis (SRS-A), which renders them useful as agents for the treatment of allergic conditions.
    Type: Grant
    Filed: January 24, 1983
    Date of Patent: March 26, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Matthew Carson, Ronald A. LeMahieu, William C. Nason
  • Patent number: 4500731
    Abstract: A compound of the formula I: ##STR1## in which R.sub.1 and R.sub.2 in any position on the benzene ring are different from each other, and independently represent a hydroxy group or an alkoxy group containing from 1 to 8 carbon atoms, or else R.sub.1 and R.sub.2 together form an --OCH.sub.2 CH.sub.2 O-radical, and R represents a hydrogen atom or an alkyl group containing from 1 to 8 carbon atoms, as well as the alkali metal, alkaline earth metal, ammonium or amine salts of the said products of formula I in which R represents a hydrogen atom. These compounds have been found useful in the treatment of hyperchlorhydria, gastric and gastro-duodenal ulcers, gastritis, hiatal hernias, and gastric and gastro-duodenal ailments accompanied by gastric hyperacidity. Pharmaceutical compositions including these compounds are disclosed along with methods for their production.
    Type: Grant
    Filed: October 20, 1982
    Date of Patent: February 19, 1985
    Assignee: Roussel Uclaf
    Inventors: Mario Bianchi, Fernando Barzaghi
  • Patent number: 4500544
    Abstract: Ascochlorin derivatives of the formula: ##STR1## wherein R is a hydroxyl group, a lower alkoxy group, a pyridyl group, an amino group, a dialkylamino group, a phenoxyalkyl group which may have a substituent in the nucleus, or a phenyl group which may have a substituent in the nucleus; and n is an integer of 0 to 5, a process for preparing the same and a pharmaceutical composition containing the same are disclosed.The derivatives are useful to treat diabetes, improve lipid metabolism and control tumors.
    Type: Grant
    Filed: August 27, 1982
    Date of Patent: February 19, 1985
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Tomoyoshi Hosokawa, Ikutoshi Matsuura, Hidenori Takahashi, Kunio Ando, Gakuzo Tamura
  • Patent number: 4499295
    Abstract: This invention relates to methods of preventing or reducing the degradation of elastin and other proteins and thereby preventing or retarding the disease states caused by said degradation by administering compounds of the formula: ##STR1## or their pharmacologically acceptable salts.
    Type: Grant
    Filed: May 9, 1983
    Date of Patent: February 12, 1985
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 4486605
    Abstract: A method for producing an aromatic carbonyl compound represented by the formula (B)-1 or (B)-2: ##STR1## comprising decomposing a hydroperoxide represented by the formula (A)-1 or (A)-2: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are defined in the specification, in an inert gas atmosphere in the presence of an aqueous layer containing an iron salt, a copper salt and an acid is disclosed. Novel m-(2-hydroxy-2-propyl)acetophenone and m-isopropenylacetophenone which are useful as an intermediate for the preparation of medicines are also disclosed. A method for producing m-isopropenylacetophenone comprising dehydrating m-(2-hydroxy-2-propyl)acetophenone in the presence of an acid catalyst is further disclosed.
    Type: Grant
    Filed: January 7, 1983
    Date of Patent: December 4, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Haruhisa Harada, Hiroshi Maki
  • Patent number: 4456768
    Abstract: Prostaglandin and prostacyclin compounds which are fluorine substituted in any one or more of the following positions 4,4; 7,7; 10,10; and 5.
    Type: Grant
    Filed: May 1, 1981
    Date of Patent: June 26, 1984
    Assignee: The University of Chicago
    Inventor: Josef Fried
  • Patent number: 4454350
    Abstract: A process for the acylation of halo- or trihalomethylbenzenes, wherein a halo- or trihalomethylbenzene is reacted with a carboxylic acid, a precursor or a derivative thereof in the presence of boron trifluoride in an amount such that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having a phytosanitary (e.g., herbicidal) or pharmaceutical activity.
    Type: Grant
    Filed: June 28, 1982
    Date of Patent: June 12, 1984
    Assignee: Rhone-Poulenc Specialities Chimiques
    Inventor: Michel Desbois
  • Patent number: 4452994
    Abstract: An improved process for isolating organic compounds from crude product or reaction mixtures by dissolving said crude product or reaction mixture in a suitable solvent, contacting the resulting solution with a lithium salt to form a solid metal salt complex, separating, and thereafter recovering a pure product by decomposing the lithium salt complex.
    Type: Grant
    Filed: March 2, 1981
    Date of Patent: June 5, 1984
    Assignee: G. D. Searle & Co.
    Inventors: John B. Hill, Robert A. Erickson
  • Patent number: 4450292
    Abstract: A compound of the formula (I) ##STR1## in which the three methoxy radicals are in the 3,4,5, or 2,4,6 or 2,4,5 or 2,3,5 or 2,3,6 positions, in which either A and B together represent a double bond or else A represents a hydrogen atom and B represents a hydroxy radical, and in which R represents a hydrogen atom or an alkyl containing 1 to 5 carbon atoms, in the various possible stereoisomeric forms, as well as the alkali metal, alkaline-earth metal, or amine salts thereof in which R represents a hydrogen atom, methods of producing the same, pharmaceutical compositions containing the same and treatment of various gastric ailments are disclosed.
    Type: Grant
    Filed: April 14, 1982
    Date of Patent: May 22, 1984
    Assignee: Roussel Uclaf
    Inventors: Yani Christidis, Robert Fournex
  • Patent number: 4440943
    Abstract: 3,7-Substituted phenoxiodinin-5-ium compounds are effective against a variety of aerobic and anaerobic bacteria as well as fungi. The compounds of this invention may be prepared by the direct iodination of a suitably substituted diphenyl ether with iodosyl sulfate in concentrated sulfuric acid. The resulting bisulfate anion may be exchanged with a desired anion by standard metathetic processes.
    Type: Grant
    Filed: March 15, 1982
    Date of Patent: April 3, 1984
    Assignee: The Dow Chemical Company
    Inventor: Edward E. Flagg
  • Patent number: 4421927
    Abstract: The present invention relates to a new cinnamoyl-cinnamic acid derivative selected from the group constituted by:(i) the m-cinnamoyl-cinnamic acid derivatives of formula ##STR1## in which: X.sub.o,X.sub.1,X.sub.2,X.sub.3,X.sub.4, which are identical or different, each represent an atom of hydrogen, a halogen, a lower alkyl group, a lower alkoxy group, the group NRR' (where R and R' identical or different, each represent an atom of hydrogen or a lower alkyl group), the group NO.sub.2, CF.sub.3 or OH;R.sub.1 represents an atom of hydrogen or a lower alkyl group;R.sub.2 represents an atom of hydrogen or the methyl group;Y represents a group OH, OR.sub.3 (where R.sub.3 is a lower alkyl group), NRR' (where R and R' are defined as hereinabove) or the group O(CH.sub.2).sub.n NR.sub.4 R.sub.5 (where n is an integer of value 1 to 5--and preferably 2 or 3)--; and R.sub.4 and R.sub.
    Type: Grant
    Filed: October 22, 1981
    Date of Patent: December 20, 1983
    Assignee: Societe de Recherches Industrielles (S.O.R.I.)
    Inventor: Francois Picart
  • Patent number: 4415746
    Abstract: This disclosure describes novel 16-aryloxy-17,18,19,20-tetranoprostanoic acids and derivatives thereof useful as bronchodilators and as hypotensive and contraceptive agents.
    Type: Grant
    Filed: October 5, 1981
    Date of Patent: November 15, 1983
    Assignee: American Cyanamid Company
    Inventors: Charles V. Grudzinskas, Martin J. Weiss
  • Patent number: 4410720
    Abstract: 11-Unsubstituted 16-fluoro-prostaglandin E.sub.2 useful as blood pressure lowering agents.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: October 18, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
  • Patent number: 4410537
    Abstract: This invention is directed to novel ether compounds of formula (I) ##STR1## which are of value in medicine in the palliation of haemoglobinopathies, in particular sickle-cell anaemia, and also in the palliation of pulmonary dysfunction, protection from the effects of hypoxia and the radio-sensitization of tumors. The invention is also directed to methods for the preparation of the ether compounds, to pharmaceutical formulations containing them, the preparation of such formulations and the use of the compounds in human medicine. Also provided by the invention are intermediates of value in the preparation of the ether compounds, by the methods described, and the preparation of the intermediates.
    Type: Grant
    Filed: June 9, 1981
    Date of Patent: October 18, 1983
    Assignee: Burroughts Wellcome Co.
    Inventor: Geoffrey Kneen
  • Patent number: 4403100
    Abstract: The present invention provides novel (11R)-11-deoxy-11-alkyl-6-oxo-prostaglandins which are useful for curing and preventing duodenal ulcers and for preventing or treating gastrointestinal cell damage caused by the use of other pharmacological agents.
    Type: Grant
    Filed: October 30, 1981
    Date of Patent: September 6, 1983
    Assignee: The Upjohn Company
    Inventor: Douglas R. Morton, Jr.
  • Patent number: 4384137
    Abstract: The invention relates to a process for preparation of hydroxyarylglyoxylic acids starting from hydroxyarylglycolic acids, by catalytic oxidation in an aqueous alkaline medium to pH higher than, or equal to, 11.5, through oxygen or oxygen-containing gas, characterized in that it is carried out in homogeneous phase at a temperature lower than, or equal to, 30.degree. C., and in the presence of cupric ions, and in that at the end of the reaction, the desired acid is isolated from the reactional medium through acidification to pH of about 0.5.The sodium parahydroxyphenylglyoxylate is obtained when acidification is stopped at pH=5, at the end of the reaction.
    Type: Grant
    Filed: April 20, 1982
    Date of Patent: May 17, 1983
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Schouteeten, Yani Christidis, Jean-Claude Vallejos
  • Patent number: 4374293
    Abstract: Allylbenzene is converted to indene by means of a tungsten-containing catalyst.
    Type: Grant
    Filed: August 14, 1981
    Date of Patent: February 15, 1983
    Assignee: The Standard Oil Co.
    Inventors: J. D. Burrington, R. K. Grasselli, C. T. Kartisek
  • Patent number: 4371547
    Abstract: 2-Benzylideneglutaraldehydes of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or a substituent selected from the group consisting of halo, lower-alkyl, phenyl, carboxy, lower-alkoxycarbonyl, phenoxycarbonyl, aminocarbonyl, hydroxysulfonyl, nitro, cyano, hydroxy, lower-alkoxy and phenoxy, a method of use thereof as disinfectants, disinfectant compositions comprising them, and 2,6-dialkoxy-3-(.alpha.-alkoxybenzyl)tetrahydropyrans of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are as defined above and R.sup.4 and R.sup.5 independently are alkyl of one to four carbon atoms, which are intermediates for their preparation are disclosed.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: February 1, 1983
    Assignee: Sterling Drug Inc.
    Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
  • Patent number: 4351846
    Abstract: Prostaglandin analogues of the formula: ##STR1## [wherein R.sup.1 represents hydrogen or alkyl of 1 to 12 carbon atoms, R.sup.2 represents a single bond or alkylene of from 1 to 5 carbon atoms, R.sup.3 represents hydrogen, alkyl or alkoxy of 1 to 8 carbon atoms, cycloalkyl or cycloalkyloxy of 4 to 7 carbon atoms unsubstituted or substituted by alkyl of 1 to 8 carbon atoms, or phenyl or phenoxy unsubstituted or substituted by halogen, trifluoromethyl or alkyl of 1 to 4 carbon atoms, one of R.sup.4 and R.sup.5 represents hydrogen and the other represents hydroxy or R.sup.4 and R.sup.5 together represent oxo, R.sup.6 represents hydrogen or a hydroxy-protecting group which may be removed under acidic conditions, the double bond between the carbon atoms in positions 13 and 14 is trans, the wavy line attached to the carbon atom in position 15 represents .alpha.- or .beta.- configuration or a mixture thereof and, when one of R.sup.4 and R.sup.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: September 28, 1982
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Kimiichiro Matsumoto, Hajimu Miyake, Hisashi Suga
  • Patent number: 4346228
    Abstract: 11-Oxoprostaglandin derivatives of the formula ##STR1## wherein R.sub.2 is a hydrogen atom or alkyl of 1-5 carbon atoms,R.sub.3 is alkyl of 1-5 carbon atoms, alkylaryl, cycloalkyl of 5-6 ring carbon atoms and a total of 5-10 carbon atoms; benzodioxol-2-yl, phenyl, naphthyl or phenyl or naphthyl substituted by phenyl, halogen, alkyl of 1-4 carbon atoms, chloromethyl, fluoromethyl, carboxyl or hydroxy;A is --CH.sub.2 --CH.sub.2 --, cis--CH.dbd.CH--, or trans--CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH--,D and E collectively are a direct bond or D is alkylene of 1-5 carbon atoms and E is an oxygen or sulfur atom; esters thereof; readily cleavable 9,15 and 9,15 ethers thereof; methanesulfonylamides thereof, and physiologically acceptable salts thereof with bases; possess the activity of the corresponding natural prostaglandins with a surprisingly longer duration of effectiveness, greater selectivity, and better effects, and can be produced, e.g.
    Type: Grant
    Filed: April 15, 1976
    Date of Patent: August 24, 1982
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Eckehard Schillinger
  • Patent number: 4334089
    Abstract: Substituted oxocarboxylic acids of the formula I ##STR1## wherein R.sup.1 denotes a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group, a lower alkoxy group or a trifluoromethyl group,R.sup.2 denotes a hydrogen atom or a halogen atom and n denotes an integer from 3 to 8,and their salts display a hypoglycaemic action in warm-blooded animals. Processes for the preparation of the new compounds and of the intermediate products required for their preparation, as well as of the corresponding medicaments are described.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: June 8, 1982
    Assignee: Byk Gulden Lomberg Chemische Fabrik Gesellschaft
    Inventors: Ekkehard Krass, Horst Wolf
  • Patent number: 4328355
    Abstract: A compound of the formula ##STR1## wherein R is hydrogen or lower alkyl having 1-7 carbon atoms; R', R", and R'" are each individually hydrogen or methyl; n is 0-3; and Ar is phenyl, halosubstituted phenyl, lower alkyl substituted phenyl wherein the lower alkyl contains 1-4 carbon atoms, lower alkoxy substituted phenyl wherein the lower alkoxy contains 1-4 carbon atoms, p-biphenyl, or trifluoromethyl substituted phenyl. Compounds of the present invention are useful as antifertility agents.
    Type: Grant
    Filed: September 10, 1979
    Date of Patent: May 4, 1982
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Raphael Pappo
  • Patent number: 4324902
    Abstract: 7-[5-oxo-3-hydroxy-2-(3-substituted)-3-hydroxypropyl)-1-cyclopentene]-hepta noic acids having the following general formula ##STR1## wherein X is oxygen or hydroxyl, R.sub.1 and R.sub.3 are independently hydrogen or methyl, and R.sub.2 is --(CH.sub.2)n-Y where n is an integer from 0 through 4 inclusive, and Y is phenyl, or a cycloalkyl group having 4 to 6 carbon atoms. Said acids as well as certain derivatives thereof are useful as nasal decongestants, inhibitors of gastric secretion, inhibitors of platelet aggregation, blood additives, smooth muscle stimulators, hypotensive agents, labor inducers, and in controlling ovulation.
    Type: Grant
    Filed: April 16, 1981
    Date of Patent: April 13, 1982
    Assignee: G. D. Searle & Co.
    Inventors: Masateru Miyano, Clifford R. Dorn
  • Patent number: 4324730
    Abstract: Prostaglandin and prostacyclin compounds which are fluorine substituted in any one or more of the following positions, 4,4; 7,7; 10,10; and 5.
    Type: Grant
    Filed: October 8, 1980
    Date of Patent: April 13, 1982
    Assignee: The University of Chicago
    Inventor: Josef Fried
  • Patent number: 4321275
    Abstract: The disclosure relates to novel 17,18,19,20-tetranor-prostanoic acid derivatives having prostaglandin-type properties, to a method for their manufacture, and also to pharmaceutical or veterinary compositions containing said novel derivatives and a method of inducing luteolysis in an animal host by use of said novel derivatives.
    Type: Grant
    Filed: May 30, 1974
    Date of Patent: March 23, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventors: Jean Bowler, Neville S. Crossley
  • Patent number: 4320143
    Abstract: Fluoro-prostaglandin compounds are disclosed, such as, for instance, 18,19,20-trinor-17-cyclohexyl-13-14-dehydro-16(S,R)-fluoro-PGF.sub.2.alpha ..The fluoro-prostaglandins of the present invention have the same therapeutical uses as natural prostaglandins, but have the advantage of being resistant to the enzyme 15-prostaglandin dehydrogenase, and also exhibit a more selective therapeutical action. Certain of the compounds of the present invention exhibit very favorable luteolytic and antiulcer activity.
    Type: Grant
    Filed: February 2, 1979
    Date of Patent: March 16, 1982
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Renato Pellegata, Carmelo Gandolfi
  • Patent number: 4304728
    Abstract: Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or R.sup.6, where R.sup.5 is hydrogen or C.sub.1-8 alkyl and R.sup.6 is phenyl or naphthyl, the phenyl or naphthyl group being optionally substituted by one or more group selected from halogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy, hydroxy, benzyloxy, nitro, trifluoromethyl, carboxyl, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, N(R.sup.5).sub.2, NHCOR.sup.5 and SR.sup.5 ; R.sup.2 is R.sup.6 or --CH.dbd.CH--R.sup.6 when R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano or 5-tetrazolyl, or R.sup.2 is --CH.dbd.CH--R.sup.6 when R.sup.1 is R.sup.6 ; R.sup.3 is hydrogen, C.sub.1-6 alkyl, halogen, hydroxy or --OCH.sub.2 R.sup.6 ; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. The compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: December 8, 1981
    Assignee: Lilly Industries Limited
    Inventors: Barry P. Clark, William J. Ross, Alec Todd
  • Patent number: 4304907
    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: May 10, 1972
    Date of Patent: December 8, 1981
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Patent number: 4301294
    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, 1980
    Date of Patent: November 17, 1981
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Patent number: 4293705
    Abstract: Novel optically active 13,14-dehydro-11-deoxy-prostaglandins having a phenyl or substituted-phenyl group on the lower side chain are disclosed.
    Type: Grant
    Filed: February 19, 1980
    Date of Patent: October 6, 1981
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Carmelo Gandolfi, Renato Pellegata, Franco Faustini, Angelo Fumagalli