Oxy Patents (Class 562/463)
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Patent number: 4675421Abstract: Compound of the general formula ##STR1## wherein R represents an ether protecting group useful as intermediates.Type: GrantFiled: August 23, 1985Date of Patent: June 23, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Richard Barner, Josef Hubscher
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Patent number: 4670581Abstract: 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: GrantFiled: January 10, 1984Date of Patent: June 2, 1987Assignee: Sugai Chemical Industry Co., Ltd.Inventor: Teiichi Tanigaki
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Patent number: 4670585Abstract: 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: GrantFiled: August 21, 1986Date of Patent: June 2, 1987Assignee: Kao CorporationInventors: Kimihiko Hori, Koichi Nakamura, Naotake Takaishi
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Patent number: 4667055Abstract: 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: GrantFiled: March 20, 1985Date of Patent: May 19, 1987Assignee: Merck Frosst Canada, Inc.Inventors: John Gillard, Joshua Rokach, Patrice C. Belanger
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Patent number: 4647413Abstract: 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: GrantFiled: January 20, 1984Date of Patent: March 3, 1987Assignee: Minnesota Mining and Manufacturing CompanyInventor: Patricia M. Savu
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Patent number: 4626597Abstract: 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: GrantFiled: August 22, 1984Date of Patent: December 2, 1986Assignee: Farmitalia Carlo Erba, S.p.A.Inventors: Franco Faustini, Roberto d'Alessio, Achille Panzeri, Enrico di Salle
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Patent number: 4625047Abstract: 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: GrantFiled: December 23, 1985Date of Patent: November 25, 1986Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Adolph M. Pietruszkiewicz, Otto W. Woltersdorf, Jr.
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Patent number: 4596883Abstract: 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: GrantFiled: July 5, 1984Date of Patent: June 24, 1986Assignee: PPG Industries, Inc.Inventors: James A. Schwindeman, Horng-Jau Lin
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Patent number: 4594443Abstract: 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: GrantFiled: August 20, 1984Date of Patent: June 10, 1986Assignee: Roussel-UclafInventors: Mario Bianchi, Fernando Barzaghi
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Patent number: 4582857Abstract: 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: GrantFiled: July 20, 1984Date of Patent: April 15, 1986Assignee: Klinge Pharma GmbHInventors: Helmut Grill, Friedemann Reiter, Roland Loser, Michael Schliack, Klaus Seibel
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Patent number: 4578505Abstract: 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: GrantFiled: September 4, 1984Date of Patent: March 25, 1986Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Richard M. Weier
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Patent number: 4567201Abstract: 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: GrantFiled: November 9, 1982Date of Patent: January 28, 1986Assignee: Takeda Chemical Industries, Ltd.Inventors: Akira Nohara, Yoshitaka Maki
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Patent number: 4562204Abstract: 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: GrantFiled: June 28, 1983Date of Patent: December 31, 1985Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Hirohisa Wakatsuka, Takashi Yamato, Shinsuke Hashimoto
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Patent number: 4560403Abstract: 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: GrantFiled: September 22, 1983Date of Patent: December 24, 1985Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
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Patent number: 4544565Abstract: 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: GrantFiled: March 29, 1984Date of Patent: October 1, 1985Assignee: General Foods CorporationInventor: Ronald E. Barnett
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Patent number: 4542233Abstract: 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: GrantFiled: July 20, 1983Date of Patent: September 17, 1985Assignee: Biaschim S.p.A.Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio
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Patent number: 4536592Abstract: The present invention encompasses 16-alkyl, 16-hydroxy-2-substituted prostaglandins which exhibit cytoprotective and antisecretory activity with greatly reduced diarrhea side effects.Type: GrantFiled: February 16, 1984Date of Patent: August 20, 1985Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Alan F. Gasiecki, Richard M. Weier
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Patent number: 4535183Abstract: 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: GrantFiled: December 18, 1981Date of Patent: August 13, 1985Assignee: Burroughs Wellcome Co.Inventor: Geoffrey Kneen
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Patent number: 4533732Abstract: 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: GrantFiled: September 30, 1983Date of Patent: August 6, 1985Assignees: Yamamoto Chemical Industrial Company, Limited, Osaka Municipal GovernmentInventors: Hiroshige Inoue, Kenichi Fukushima, Ikuzo Nishiguchi
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Patent number: 4528371Abstract: 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: GrantFiled: June 14, 1983Date of Patent: July 9, 1985Assignee: Smith Kline & French Laboratories LimitedInventors: William J. Coates, Brian H. Warrington
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Patent number: 4507498Abstract: 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: GrantFiled: January 24, 1983Date of Patent: March 26, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Matthew Carson, Ronald A. LeMahieu, William C. Nason
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Patent number: 4500731Abstract: 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: GrantFiled: October 20, 1982Date of Patent: February 19, 1985Assignee: Roussel UclafInventors: Mario Bianchi, Fernando Barzaghi
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Patent number: 4500544Abstract: 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: GrantFiled: August 27, 1982Date of Patent: February 19, 1985Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Tomoyoshi Hosokawa, Ikutoshi Matsuura, Hidenori Takahashi, Kunio Ando, Gakuzo Tamura
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Patent number: 4499295Abstract: 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: GrantFiled: May 9, 1983Date of Patent: February 12, 1985Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 4486605Abstract: 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: GrantFiled: January 7, 1983Date of Patent: December 4, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Haruhisa Harada, Hiroshi Maki
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Patent number: 4456768Abstract: 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: GrantFiled: May 1, 1981Date of Patent: June 26, 1984Assignee: The University of ChicagoInventor: Josef Fried
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Patent number: 4454350Abstract: 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: GrantFiled: June 28, 1982Date of Patent: June 12, 1984Assignee: Rhone-Poulenc Specialities ChimiquesInventor: Michel Desbois
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Patent number: 4452994Abstract: 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: GrantFiled: March 2, 1981Date of Patent: June 5, 1984Assignee: G. D. Searle & Co.Inventors: John B. Hill, Robert A. Erickson
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Patent number: 4450292Abstract: 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: GrantFiled: April 14, 1982Date of Patent: May 22, 1984Assignee: Roussel UclafInventors: Yani Christidis, Robert Fournex
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Patent number: 4440943Abstract: 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: GrantFiled: March 15, 1982Date of Patent: April 3, 1984Assignee: The Dow Chemical CompanyInventor: Edward E. Flagg
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Patent number: 4421927Abstract: 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: GrantFiled: October 22, 1981Date of Patent: December 20, 1983Assignee: Societe de Recherches Industrielles (S.O.R.I.)Inventor: Francois Picart
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Patent number: 4415746Abstract: 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: GrantFiled: October 5, 1981Date of Patent: November 15, 1983Assignee: American Cyanamid CompanyInventors: Charles V. Grudzinskas, Martin J. Weiss
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Patent number: 4410720Abstract: 11-Unsubstituted 16-fluoro-prostaglandin E.sub.2 useful as blood pressure lowering agents.Type: GrantFiled: October 26, 1981Date of Patent: October 18, 1983Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
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Patent number: 4410537Abstract: 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: GrantFiled: June 9, 1981Date of Patent: October 18, 1983Assignee: Burroughts Wellcome Co.Inventor: Geoffrey Kneen
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Patent number: 4403100Abstract: 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: GrantFiled: October 30, 1981Date of Patent: September 6, 1983Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
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Patent number: 4384137Abstract: 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: GrantFiled: April 20, 1982Date of Patent: May 17, 1983Assignee: Societe Francaise HoechstInventors: Alain Schouteeten, Yani Christidis, Jean-Claude Vallejos
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Patent number: 4374293Abstract: Allylbenzene is converted to indene by means of a tungsten-containing catalyst.Type: GrantFiled: August 14, 1981Date of Patent: February 15, 1983Assignee: The Standard Oil Co.Inventors: J. D. Burrington, R. K. Grasselli, C. T. Kartisek
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Patent number: 4371547Abstract: 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: GrantFiled: August 21, 1981Date of Patent: February 1, 1983Assignee: Sterling Drug Inc.Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
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Patent number: 4351846Abstract: 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: GrantFiled: May 8, 1981Date of Patent: September 28, 1982Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Kimiichiro Matsumoto, Hajimu Miyake, Hisashi Suga
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Patent number: 4346228Abstract: 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: GrantFiled: April 15, 1976Date of Patent: August 24, 1982Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4334089Abstract: 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: GrantFiled: June 29, 1981Date of Patent: June 8, 1982Assignee: Byk Gulden Lomberg Chemische Fabrik GesellschaftInventors: Ekkehard Krass, Horst Wolf
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Patent number: 4328355Abstract: 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: GrantFiled: September 10, 1979Date of Patent: May 4, 1982Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Raphael Pappo
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Patent number: 4324902Abstract: 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: GrantFiled: April 16, 1981Date of Patent: April 13, 1982Assignee: G. D. Searle & Co.Inventors: Masateru Miyano, Clifford R. Dorn
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Patent number: 4324730Abstract: 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: GrantFiled: October 8, 1980Date of Patent: April 13, 1982Assignee: The University of ChicagoInventor: Josef Fried
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Patent number: 4321275Abstract: 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: GrantFiled: May 30, 1974Date of Patent: March 23, 1982Assignee: Imperial Chemical Industries LimitedInventors: Jean Bowler, Neville S. Crossley
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Patent number: 4320143Abstract: 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: GrantFiled: February 2, 1979Date of Patent: March 16, 1982Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Renato Pellegata, Carmelo Gandolfi
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Patent number: 4304728Abstract: 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: GrantFiled: March 27, 1980Date of Patent: December 8, 1981Assignee: Lilly Industries LimitedInventors: Barry P. Clark, William J. Ross, Alec Todd
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Patent number: 4304907Abstract: 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: GrantFiled: May 10, 1972Date of Patent: December 8, 1981Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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Patent number: 4301294Abstract: 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: GrantFiled: December 19, 1980Date of Patent: November 17, 1981Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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Patent number: 4293705Abstract: Novel optically active 13,14-dehydro-11-deoxy-prostaglandins having a phenyl or substituted-phenyl group on the lower side chain are disclosed.Type: GrantFiled: February 19, 1980Date of Patent: October 6, 1981Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Carmelo Gandolfi, Renato Pellegata, Franco Faustini, Angelo Fumagalli