Halogen Containing Patents (Class 568/645)
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Patent number: 4610996Abstract: Phenoxytriazolyl ketones and carbinols of the formula ##STR1## in which A represents the keto group or the CH(OH) grouping andR represents hydrogen, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, alkylcarbonyl, optionally substituted benzyl or optionally substituted phenoxymethyl,or addition products thereof with acids or metal salts, which possess fungicidal activity.Type: GrantFiled: April 11, 1984Date of Patent: September 9, 1986Assignee: Bayer AktiengesellschaftInventors: Udo Kraatz, Karl H. Buchel, Paul Reinecke, Wilhelm Brandes, Gerd Hanssler
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Patent number: 4578396Abstract: Hydroxyalkinyl-azolyl derivatives of the formula ##STR1## in which A is a nitrogen atom or the CH group,R is optionally substituted alkyl, cycloalkyl or phenyl,R.sup.1 is hydrogen, alkyl, alkenyl, alkinyl, or optionally substituted benzyl,R.sup.2 is hydrogen or methyl, andX is hydrogen, bromine or iodine,or addition products thereof with acids or metal salts exhibit fungicidal activity. Some intermediates therefor are also new.Type: GrantFiled: May 27, 1983Date of Patent: March 25, 1986Assignee: Bayer AktiengesellschaftInventors: Gerhard Jager, Klaus Bockmann, Karl H. Buchel, Wilhelm Brandes, Paul-Ernst Frohberger, Hans Scheinpflug
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Patent number: 4567184Abstract: Compounds of the structure ##STR1## and pharmaceutically acceptable salts thereof, wherein R.sub.1 and R.sub.2 are independently hydrogen, alkyl, carboxy, alkylcarboxy, arylcarboxy, alkyl carbalkoxy, alkanoyl, formyl, nitrile, amino, amino alkyl, alkylamine, carboxamide, halo, trihalomethyl, hydroxy, alkoxy, aryloxy, nitro, sulfonyl, sulfonamide, thio, alkylthio, or R.sub.1 and R.sub.2 can be taken together to form a phenyl ring;B is C or N, in which N can be in any position of the ring;X is O, S, NR.sub.4, CH.sub.2 Z, CH.dbd.N, CH.dbd.CH, C.tbd.C, CH.sub.2 ZCH.sub.2, C.dbd.O, C.dbd.CR or WC.dbd.O;Y is CHCH.sub.2, C.dbd.CH, C--CH.sub.2, CHCHR.sub.5, CHC(R.sub.5).sub.2 or CC(R.sub.5).sub.2 ;R.sub.3 is O, OH, OR.sub.4, SH, SR.sub.4, NH, HNR.sub.4 or N(R.sub.4).sub.2 ; andM is an integer from 0 to 10; wherein Z is O, S or NR.sub.4 ; R.sub.4 is H, alkyl or aryl;W is O, S or NR.sub.4 ; and R.sub.5 is H, alkyl or fluoro have antiinflammatory and antiallergic activities.Type: GrantFiled: September 9, 1983Date of Patent: January 28, 1986Assignee: USV Pharmaceutical CorporationInventors: John H. Musser, Utpal R. Chakraborty
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Patent number: 4551264Abstract: New polyhalogenoaromatic compounds of Formula I ##STR1## wherein Y and Z are each independently alkyl, alkoxy or alkanoyl each of 1 to 12 C atoms, --COOR.sup.1, --O--CO--R.sup.1, CN, NO.sub.2, NH.sub.2 or OH;Q is one or two identical or different radicals selected from Ph, Cy, 1,4-bicyclo[2,2,2]octylene or 1,3-dioxane-2,5-diyl;X.sup.1 to X.sup.4 are each independently H, F, Cl or Br;R.sup.1 is alkyl of 1 to 4 C atoms, Ph--R.sup.2 or Cy--R.sup.2 ;R.sup.2 is alkyl or alkoxy each of 1-12 C atoms or CN;Ph is 1,4-phenylene; and Cy is 1,4-cyclohexylene,can be used as components of liquid-crystal dielectrics.Type: GrantFiled: March 14, 1983Date of Patent: November 5, 1985Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Michael Romer, Georg Weber
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Patent number: 4495370Abstract: A process for the preparation of a 5-aryloxy-1-chloro-3,3-dimethyl-2-pentanone of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently is halogen, alkyl having 1 to 4 carbon atoms, alkoxy or alkylthio each having 1 to 2 carbon atoms, halogenoalkyl, halogenoalkoxy or halogenoalkylthio each having 1 to 2 carbon atoms and 1 to 5 halogen atoms, cyclohexyl, dialkylamino having 1 to 4 carbon atoms in each alkyl moiety, nitro, cyano, alkoxy-carbonyl having 1 to 4 carbon atoms in the alkyl moiety, phenyl or halophenyl, m and n each independently is an integer from 0 to 5, and m+n.ltoreq.5,comprising reacting 1,1,5-trichloro-3,3-dimethyl-1-pentene of the formula ##STR2## with a phenol of the formula ##STR3## in the presence of a base in a diluent, to produce a compound of the formula ##STR4## and subjecting such reaction product to acid hydrolysis.Type: GrantFiled: May 27, 1983Date of Patent: January 22, 1985Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Gerhard Jager
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Patent number: 4447651Abstract: 1,4-Bis-(4-chloro-2-methoxystyryl)-benzene is highly suitable for whitening polymeric substances, in which use it is distinguished, for example, by a good yield and a pleasant shade.Type: GrantFiled: April 22, 1982Date of Patent: May 8, 1984Assignee: Bayer AktiengesellschaftInventors: Carl-Wolfgang Schellhammer, Bernhard Wehling
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Patent number: 4414210Abstract: This invention relates to 2-hydroxyarylethyl-1,2,4-triazoles, their acid addition salts and metal salt complexes. This invention also relates to the method of preparation and use of these compounds. These compounds and salts thereof are highly active broad-spectrum systemic fungicides effective in controlling phytopathogenic fungi such as barley net blotch (Helminthosporium teres), grey mold (Botrytis fabae), bean powdery mildew (Erysiphe polygoni), grape downy mildew (Plasmopora viticola), rice blast (Piricularia oryzae), tomato late blight (Phytophthora infestans) and wheat stem rust (Puccinia graminis f. sp. tritici race 158-2).Type: GrantFiled: May 19, 1981Date of Patent: November 8, 1983Assignee: Rohm and Haas CompanyInventors: George A. Miller, Hak-Foon Chan
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Patent number: 4400293Abstract: Cyclohexylphenyl derivatives of the formula ##STR1## wherein X is --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --O--, --CH.sub.2 --S--, --O--CH.sub.2 -- or --S--CH.sub.2 --; R.sub.1 is alkyl of up to 8 carbon atoms; R.sub.2 is alkyl or alkoxy each of up to 8 carbon atoms, fluorine, chlorine, bromine or cyano; and R.sub.3 and R.sub.4 are both hydrogen or one is hydrogen and the other is fluorine, chlorine, bromine or cyano, with the proviso that R.sub.3 and R.sub.4 are both hydrogen when X is --CH.sub.2 --CH.sub.2 -- or R.sub.2 is fluorine, chlorine, bromine or cyano, are valuable liquid crystalline compounds.Type: GrantFiled: October 29, 1981Date of Patent: August 23, 1983Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Michael Romer, Joachim Krause, Ludwig Pohl
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Patent number: 4361494Abstract: New anisotropic compounds suitable for use in LC-display devices are disclosed and claimed. The new compounds are cyclohexyl cyclohexylmethyl ethers of formula (1): ##STR1## in which X and Y are respectively hydrogen, alkyl group with 1 to 12 C-atoms, alkoxy group with 1 to 12 C-atoms, monoalkylamino group with 1 to 12 C-atoms, nitrile group, nitro group, halogen, or cyclic radical of formula (1a) or (1b): ##STR2## in which R.sup.1 and R.sup.2 represent hydrogen alkyl group with 1 to 12 C-atoms, alkoxy group with 1 to 12 C-atoms, monoalkylamino group with 1 to 12 C-atoms, nitrile group, nitro group or halogen, and Z.sup.1 and Z.sup.2 represent simple covalent bonds or grounds of the formulas --COO--, --OOC--, --CH.sub.2 O-- or --OCH.sub.2, with the requirement that only one of the groups X, Y can be a cyclicradical or formula (1a) or (1b). Also disclosed and claimed are LC-mixtures containing these compounds and methods for their synthesis.Type: GrantFiled: December 17, 1980Date of Patent: November 30, 1982Assignee: BBC Brown, Boveri, & Company, LimitedInventors: Maged A. Osman, Laszlo Revesz
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Patent number: 4357078Abstract: Novel liquid crystal compounds exhibiting a low dielectric anisotropy have a structural formula: ##STR1## where R.sub.1 is an alkyl group, R.sub.2 is a group containing an alkyl group R and is either an alkyl group R, an alkoxy group OR, an alkylcarbonyloxy group OCOR or an alkoxycarbonyloxy group OCOOR, R.sub.1 and R containing up to 18 carbon atoms, ##STR2## is a trans-1,4-disubstituted cyclohexane ring ##STR3## or a 1,4-disubstituted bicyclo(2,2,2)octane ring ##STR4## and Ar is a 1,4 disubstituted benzene ring ##STR5## a 3-fluoro-1,4 disubstituted benzene ring ##STR6## or a 2,6 disubstituted naphthalene ring ##STR7## These compounds may be used in liquid crystal mixture compositions for use in a number of known electro-optic effects.The compounds may be prepared by routes in which the individual steps involved are known.Type: GrantFiled: January 27, 1981Date of Patent: November 2, 1982Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Neil Carr, George W. Gray, Stephen M. Kelly
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Patent number: 4349487Abstract: Phenolic compounds are etherified by contacting at elevated temperature with a mixture of methyl trichloroacetate and either a primary alkyl halide or an aromatic halide containing strongly electron-withdrawing groups in the presence of an initiator.Type: GrantFiled: August 24, 1981Date of Patent: September 14, 1982Assignee: The Dow Chemical CompanyInventors: James M. Renga, Pen-Chung Wang
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Patent number: 4334111Abstract: Benzotrihalides are prepared by pyrolyzing a substituted phenyl trihaloacetate of the formula ##STR1## wherein each X is halo, nitro, alkyloxy, aryloxy, aralkyoxy, cyano, lower alkyl, haloalkyl, haloalkyloxy, alkenyl, haloalkenyl, carbamoyl, N,N-dialkylcarbamoyl, N,N-diarylcarbamoyl, or N,N-diaralkyloxy;Y is halo; andn is an integer of from 1 to 5. As an example, 4-chlorophenyl trichloroacetate is pyrolyzed at 550.degree. C. to 4-chlorobenzotrichloride.Type: GrantFiled: February 17, 1978Date of Patent: June 8, 1982Assignee: The Dow Chemical CompanyInventors: Ralph A. Davis, R. Garth Pews
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Patent number: 4317941Abstract: The present specification relates to novel 9-deoxy-9-methylene-trans-2,3-didehydro-PGF compounds with improved pharmacological properties. While these compounds are useful in inducing a wide variety of prostaglandin-like pharmacological effects, they are specifically useful as regulators of procreation and fertility.Type: GrantFiled: August 11, 1978Date of Patent: March 2, 1982Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4310700Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: January 12, 1982Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4306095Abstract: 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: GrantFiled: November 19, 1979Date of Patent: December 15, 1981Assignee: Imperial Chemical Industries LimitedInventor: Jean Bowler
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Patent number: 4291175Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 22, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4291174Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation inhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 22, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4289910Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 15, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4288630Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 8, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4288633Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 8, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4288632Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 8, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4288629Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation inhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: September 8, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4287125Abstract: Benzenoid ethers/thioethers are prepared by reacting an activated halobenzene with an anionic reactant, RA.sup.- M.sup.+, in the presence of at least one tertiary amine sequestering agent having formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: June 20, 1980Date of Patent: September 1, 1981Assignee: Rhone-Poulenc IndustriesInventor: Gerard Soula
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Patent number: 4282388Abstract: Novel benzyl ethers of cyclic 1,1-diols, of the formula ##STR1## wherein R.sup.1 is phenyl or substituted phenyl,R.sup.2 is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl or --CHX--R.sup.1,X is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, phenyl or substituted phenyl,Y and Y' are individually selected from hydrogen, alkyl, phenyl and substituted phenyl andA is saturated or unsaturated alkylene or substituted alkylene;have been found outstandingly effective as herbicides, particularly as selective herbicides.Type: GrantFiled: November 28, 1978Date of Patent: August 4, 1981Assignee: Bayer AktiengesellschaftInventors: Wilfried Draber, Wolf Reiser, Thomas Schmidt, Ludwig Eue, Robert R. Schmidt
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Patent number: 4244956Abstract: A method of treating inflammation and inhibiting prostaglandin synthesis employing substituted 2-(arylmethoxy)phenol compounds.Type: GrantFiled: November 26, 1979Date of Patent: January 13, 1981Assignee: Forsyth Dental Infirmary for ChildrenInventor: Floyd E. Dewhirst
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Patent number: 4223169Abstract: A process is disclosed for the essentially complete bromination of bisphenoxyethane and bisphenoxypropane, and their substitution products, with minimal cleavage of the phenoxy-to-alkylene linkages, characterized by reacting the bisphenoxyalkane reactant with a stoichiometric excess of bromine chloride in the presence of a Lewis acid catalyst and a chemically inert organic solvent adapted to dissolve all of such reactants and the catalyst. Optionally, the bisphenoxyalkane reactant and the resulting product of the process may have alkyl and chlorine substituents in either or both phenyl groups.Type: GrantFiled: February 3, 1978Date of Patent: September 16, 1980Assignee: Ferro CorporationInventor: Henry J. Barda
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4199531Abstract: A novel method for producing hydroquinone and quinone derivatives by a regio- and stereo-specific coupling reaction of hydroquinone derivative having a terminal activated (poly)prenyl side chain with a prenyl derivative. This method can provide in good yield various hydroquinone and quinone derivatives having any prenyl length of the side chain.Type: GrantFiled: October 11, 1977Date of Patent: April 22, 1980Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Kaneyoshi Kato
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Patent number: 4194054Abstract: A process for the preparation of a substituted fluorobenzene of the formula ##STR1## in which R is alkyl, alkoxy, halogen, amino, acylamido, carboxyl, benzyloxy, aryloxy, or benzyloxy or aryloxy carrying at least one alkyl, alkoxy, halogen or halogenoalkyl substituent,R.sup.1 each independently is alkyl or halogen, andn is an integer from 0 to 4, comprising reacting an N-aryl-N',N'-dialkyl-triazene of the formula ##STR2## in which Alkyl is alkyl with 1 to 4 carbon atoms, with about a 5 to 25-fold molar excess of anhydrous hydrofluoric acid at a temperature between about -20.degree. and +150.degree. C.Type: GrantFiled: November 7, 1977Date of Patent: March 18, 1980Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Hans Klusacek, Arthur Wenz
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Patent number: 4189610Abstract: Dehydrohalogenation-rearrangement of 1,1-bis(4-oxy-substituted aryl)-2-haloethanes to yield 4,4'-dioxysubstituted stilbenes is effected by heating an acidic reaction medium comprising the 1,1-bis(4-oxy-substituted aryl)-2-haloethane dissolved in a solution of an aliphatic carboxylic acid and a carboxylic acid salt. The process is particularly directed to the preparation of 4,4'-dihydroxystilbene from 1,1-bis(4-hydroxyphenyl)-2-chloroethane.Type: GrantFiled: October 31, 1977Date of Patent: February 19, 1980Assignee: Monsanto CompanyInventor: James P. Coleman
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Patent number: 4182911Abstract: Novel optically-active (S)- 1-aryloxy-2,3-epoxy-propane derivatives, a process for their manufacture, various intermediates used in the preparation thereof, and a process for using them for the manufacture of optically-active (S)-1-aryloxy-3-amino-2-propanol derivatives useful as .beta.-adrenergic blocking agents.Type: GrantFiled: December 20, 1977Date of Patent: January 8, 1980Assignee: Imperial Chemical Industries LimitedInventor: Howard Tucker
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Patent number: 4172839Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.2 series.Type: GrantFiled: December 8, 1977Date of Patent: October 30, 1979Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4170597Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the E.sub.2 series.Type: GrantFiled: December 8, 1977Date of Patent: October 9, 1979Assignee: American Cyanamid CompanyInventor: Allan Wissner
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Patent number: 4168388Abstract: Trifluoromethylphenols are prepared by hydrogenation of the corresponding trifluoromethylbenzylethers.Type: GrantFiled: March 23, 1978Date of Patent: September 18, 1979Assignee: Eli Lilly and CompanyInventors: Edward R. Lavagnino, Bryan B. Molloy, Paul Pranc
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Patent number: 4165436Abstract: The present specification relates to novel 9-deoxy-9-methylene-trans-2,3-didehydro-PGF compounds with improved pharmacological properties. While these compounds are useful in inducing a wide variety of prostaglandin-like pharmacological effects, they are specifically useful as regulators of procreation and fertility.Type: GrantFiled: April 5, 1978Date of Patent: August 21, 1979Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4163865Abstract: An improvement in a process for the preparation of a pinacol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent optionally substituted aliphatic, cycloaliphatic, araliphatic or an aromatic hydrocarbon radical by reducing a ketone of the formula ##STR2## wherein R.sup.1 and R.sup.2 have the abovementioned meanings with a base metal, the improvement comprising carrying out the reduction in the presence of an organic halogen compound and in the presence of a phosphoric acid amide, phosphoric acid ester and/or carboxylic acid amide.Type: GrantFiled: April 3, 1978Date of Patent: August 7, 1979Assignee: Bayer AktiengesellschaftInventors: Heinrich Wolfers, Hans Rudolph, Hans-Jurgen Rosenkranz
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Patent number: 4153719Abstract: Beta-diketones substituted by an aryl-aliphatic group in which the aliphatic chain is interrupted by a cyclic group, and useful as anti-viral agents, are prepared by interacting the appropriate aryl-aliphatic halide with an alkali metal salt of a beta-diketone.Type: GrantFiled: September 6, 1977Date of Patent: May 8, 1979Assignee: Sterling Drug Inc.Inventor: Guy D. Diana
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Patent number: 4145561Abstract: The present invention relates to novel 2-decarboxy-2-hydroxymethyl-9-deoxy-9-methylene-16-phenyl-PGF compounds. These compounds are useful pharmacological agents, and are useful for the same purposes as the corresponding PGE-type compounds.Type: GrantFiled: July 12, 1978Date of Patent: March 20, 1979Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4144351Abstract: New 1,3-disubstituted propanol-(2) derivatives and their nicotinic acid esters of the general formula ##STR1## and their therapeutically acceptable salts, processes for preparing the same and the use thereof and pharmaceutical preparations containing the same for the treatment of hyperlipemia.Type: GrantFiled: November 9, 1977Date of Patent: March 13, 1979Assignee: Klinge Pharma GmbH & Co.Inventors: Helmut Grill, Rainer H. Zschocke, Josef Wagner, Gernot Hofrichter, P. Stefan Janiak
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Patent number: 4144276Abstract: This invention comprises certain analogs PGE or 11-deoxy-PGE compounds in which the carbonyl at C-9 is replaced by methylene. 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: GrantFiled: May 8, 1978Date of Patent: March 13, 1979Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4140863Abstract: The present invention relates to certain 9,11-dideoxy-PGF-type compounds wherein the C-9 and C-11 carbon atoms are substituted by halogen. In particular, 9,11-chloro-, 9,11-bromo-, and 9,11-iodo-9,11-dideoxy-PGF compounds are disclosed.These compounds are particularly useful for numerous pharmacological purposes, based on their ability to stimulate mammalian smooth muscle tissue.Type: GrantFiled: June 17, 1977Date of Patent: February 20, 1979Assignee: The Upjohn CompanyInventor: Roy A. Johnson
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Patent number: 4130591Abstract: This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol and the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes 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: GrantFiled: February 24, 1978Date of Patent: December 19, 1978Assignee: The Upjohn CompanyInventor: Herman W. Smith
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Patent number: 4127733Abstract: This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes 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: GrantFiled: August 5, 1977Date of Patent: November 28, 1978Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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Patent number: RE31624Abstract: A method of treating inflammation and inhibiting prostaglandin synthesis employing substituted 2-(arylmethoxy)phenol compounds.Type: GrantFiled: December 22, 1982Date of Patent: July 3, 1984Assignee: Forsyth Dental Infirmary for ChildrenInventor: Floyd E. Dewhirst