Sulfur, Bonded Directly To A Ring, In Same Side Chain As Ester Function Patents (Class 560/17)
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Patent number: 4681971Abstract: The invention relates to pyrrolinones of formula (1) ##STR1## wherein R.sub.1 is an alkyl group containing at least 2 carbon atoms, an aralkyl group, an isocyclic or heterocyclic aromatic radical and R is an alkyl or aryl group.The invention also relates to aminodicarboxylates of formula (2) ##STR2## wherein R.sub.1 is as defined in claim 1 and R and R' are the same or different and are alkyl or aryl.The aminodicarboxylates of formula (2) are prepared by condensing a disuccinate of the formulaR'OOCCH.sub.2 CH.sub.2 COORwith a nitrile of the formula R.sub.1 CN, in the presence of a strong base and zinc chloride.The pyrrolinones of formula (1) are obtained by reacting the aminodicarboxylates of formula (2) in the presence of a strong base in an organic solvent.The compounds of formulae (1) and (2) are valuable intermediates for pigments.Type: GrantFiled: November 1, 1985Date of Patent: July 21, 1987Assignee: Ciba-Geigy CorporationInventors: Johannes Pfenninger, Abul Iqbal, Alain C. Rochat
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Patent number: 4670577Abstract: A novel process for the preparation of pent-4-enoic acids of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, cyano and alkoxycarbonyl of 2 to 5 carbon atoms and Y is selected from the group consisting of hydrogen, cyano, alkoxycarbonyl 2 to 5 carbon atoms, acyl of an organic carboxylic acid of 2 to 7 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms and arylsulfonyl of 6 to 7 carbon atoms with the proviso that X and Y are not both hydrogen comprising reacting a compound of the formula ##STR2## wherein R is selected from the group consisting of acyloxy of an organic carboxylic acid of 1 to 7 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms and arylsulfonyl of 6 to 7 carbon atoms with an anion derivative of a compound of the formula ##STR3## wherein X.sub.1 and Y.sub.Type: GrantFiled: February 24, 1984Date of Patent: June 2, 1987Assignee: Roussel UclafInventors: Marc Julia, Therese Cuvigny
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Patent number: 4670470Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.Type: GrantFiled: August 29, 1985Date of Patent: June 2, 1987Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4661617Abstract: Substituted alkenoates and alkanoates, intermediates therefor, synthesis thereof, and their use for the control of pests.Type: GrantFiled: April 19, 1985Date of Patent: April 28, 1987Assignee: Sandoz Ltd.Inventor: Clive A. Henrick
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Patent number: 4661515Abstract: Novel compounds possessing both angiotensin enzyme inhibitory activity and diuretic activity are disclosed. The compounds are represented by the general formula ##STR1## in which X is ##STR2## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, and cycloalkyl, and may be the same or different; n is an integer from 0 to 4 inclusive; M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cyloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl, or M and R.sub.6 taken together with the nitrogen to which M is bonded and the carbon to which R.sub.Type: GrantFiled: January 17, 1986Date of Patent: April 28, 1987Assignee: USV Pharmaceutical CorporationInventors: Edward S. Neiss, John T. Suh, John J. Piwinski
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Patent number: 4659855Abstract: Certain novel aryl sulfonyl fluorides, their preparation, and their use in inhibiting serine proteases with chymotrypsin-like and elastase-like specificity.Type: GrantFiled: May 9, 1983Date of Patent: April 21, 1987Assignee: Georgia Tech Research CorporationInventor: James C. Powers
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Patent number: 4647585Abstract: Bicycloheptane substituted ether prostaglandin analogs are provided having the structural formula ##STR1## wherein X is O or ##STR2## and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombotic disease.Type: GrantFiled: November 8, 1984Date of Patent: March 3, 1987Assignee: E. R. Squibb & Sons, Inc.Inventors: Melanie J. Loots, Steven E. Hall, Peter W. Sprague
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Patent number: 4634728Abstract: Polyol carboxyalkylthioalkanoamidophenol compounds useful in the stabilization of organic materials normally susceptible to oxidative degradation are prepared by (A) reaction of an appropriate polythiol, which is a selected tetra-(mercapto alkanoic acid) ester of pentaerythritol or a selected tri-(mercapto alkanoic acid) ester of a selected 1,1,1-trimethylolalkane, with an appropriate alkenyl compound, which is a selected N-alkenoyl[4-amino(mono- or dialkyl)phenol] or (B), where the alkanol moiety is a sole methylene group, by reaction of pentaerythritol or an appropriate 1,1,1-trimethylolalkane with an appropriate mercapto-N(mono- or di-alkyl-4-hydroxyphenylalkamide) alkanoic acid. In a preferred embodiment, the compound is pentaerythritol tetrakis[3-mercapto-N-(3',5'-di-ti-butyl-4'-hydroxyphenyl propanamide) propionate].Type: GrantFiled: August 20, 1985Date of Patent: January 6, 1987Assignee: Mallinckrodt, Inc.Inventors: Neil Dunski, Ali A. Bazzi, Henry J. Buehler
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Patent number: 4634715Abstract: There are disclosed aza analogs of carboxyalkyl dipeptide derivatives and related compounds which are useful as converting enzyme inhibitors and as antihypertensives said compounds being represented by the general formula: ##STR1## wherein A and B can be joined together to form various ring structures.Type: GrantFiled: July 27, 1983Date of Patent: January 6, 1987Assignee: Merck & Co., Inc.Inventors: William J. Greenlee, Eugene D. Thorsett
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Patent number: 4633013Abstract: Disclosed is a process for the preparation of .alpha.-haloacetoacetic esters by the reaction of an alkali metal alkoxide with a 5-halo-4H-1,3-dioxin-4-one compound, the desired product being obtained as an alkali metal salt which may be converted to the corresponding free ester by treating with acid.Type: GrantFiled: June 11, 1984Date of Patent: December 30, 1986Assignee: Eastman Kodak CompanyInventor: Robert J. Clemens
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Patent number: 4629737Abstract: A compound of formula (I): ##STR1## or a pharmaceutically acceptable salt, ester or amide thereof, in which: W is an optionally substituted phenyl group of the formula ##STR2## wherein R.sup.1 is hydrogen or fluorine, R.sup.2 is hydrogen, C.sub.1-6 alkyl, halogen or trifluoromethyl; or W is a phenoxymethyl or benzofuran-2-yl group;R.sup.3 is C.sub.1-12 alkyl or phenyl C.sub.1-6 alkyl;A is hydrogen or methyl,X is carboxy, --Z--CO.sub.2 H, --Z--OH, T--Z--CO.sub.2 H,--Z--NR.sup.4 R.sup.5, --T--Y--OM, --T--Y--NR.sup.4 R.sup.5, or --T--R.sup.6, in the para- or meta-position with respect to the --(CH.sub.2).sub.n group,whereinR.sup.4 and R.sup.5 are each hydrogen or C.sub.1-6 alkyl,R.sup.6 is C.sub.1-6 alkyl,T is 0, S, --NH or --N--R.sup.7, in which R.sup.7 is C.sub.1-6 alkylZ is C.sub.1-10 straight or branched alkylene optionally containing a carbon-carbon double bond;Y is C.sub.2-10 straight or branched alkylene, provided that the hetero atoms in --T--Y--OM and --T--Y--NR.sup.4 R.sup.Type: GrantFiled: July 14, 1983Date of Patent: December 16, 1986Assignee: Beecham Group p.l.c.Inventor: Barrie C. C. Cantello
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Patent number: 4604417Abstract: There are disclosed polymerizable thioester synergists which have utility in enhancing the antioxidative activity of phenolic and amine stabilizers. The invention is also concerned with the thioesters themselves, their use in oxidizable organics, their combination with polymerizable and/or conventional antioxidants, and with polymers which contain these thioesters as physical admixtures or segmeric units of the polymer.Type: GrantFiled: December 10, 1984Date of Patent: August 5, 1986Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4596823Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo[2,2,1]hept-2Z-ene, bicyclo[2,2,1]heptane, 7-oxabicyclo[2,2,1]hept-2Z-ene, 7-oxabicyclo[2,2,1]heptane, bicyclo[2,2,2]oct-2Z-ene or bicyclo[2,2,2]octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group C(R.sup.2).dbd.NR, a 6,6-dimethyl-bicyclo[3,1,1]heptane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group C(R.sup.2).dbd.NR or at the 5-position by the group C(R.sup.2).dbd.NR and at the 6-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group C(R.sup.2).dbd.NR, or a 1-hydroxycyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group C(R.sup.2).dbd.NR, R.sup.1 is a 6-caboxyhex-2-enyl group or a modification thereof as defined herein, R.sup.Type: GrantFiled: February 12, 1982Date of Patent: June 24, 1986Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4595687Abstract: Sparsomycin derivatives of the formula ##STR1## wherein X and Y are each independently an oxo or an imino group; n is 0 or the integer 1 or 2; R.sub.1 is a hydrogen or 1 to 4 carbon alkyl group; R.sub.2 is a hydrogen, a 1 to 4 carbon alkyl, a 2 to 5 carbon acyl or a benzoyl group; and R is a 1 to 6 carbon alkyl, 3 to 8 carbon alkenyl, cyanomethyl carboxymethyl, carbalkoxymethyl wherein the alkoxy moiety is a 1 to 4 carbon alkoxy group, nitromethyl, alkylcarbonylmethyl wherein the alkyl moiety is a 1 to 4 carbon alkyl group, pyridyl, furanyl, or furfuryl group or a phenyl or benzyl group optionally substituted by a methylenedioxy or one to two halogen, 1 to 4 carbon alkyl, 1 to 4 carbon alkoxy, 1 to 4 carbon alkylthio, hydroxy, nitro or cyano groups or a pharmaceutically acceptable acid addition salt thereof. Also described are their use as antiprotozoals and antibacterials.Type: GrantFiled: July 18, 1984Date of Patent: June 17, 1986Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Douglas W. Beight, Gary A. Flynn
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Patent number: 4582913Abstract: Disclosed are novel 5-halo-4H-1,3-dioxin-4-ones and their preparation by treating a compound having the formula ##STR1## with X.sub.2 or SO.sub.2 X.sub.2 wherein X is Cl or Br.Type: GrantFiled: June 11, 1984Date of Patent: April 15, 1986Assignee: Eastman Kodak CompanyInventor: Robert J. Clemens
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Patent number: 4559379Abstract: The title compounds correspond to the formula ##STR1## where n is 1 and are characterized in that at least one of A, X or Y contains a group of formula ##STR2## these compounds being useful as stabilizers for organic polymers and lubricating oils to counteract the degradative effects of heat, light and air.Type: GrantFiled: February 5, 1985Date of Patent: December 17, 1985Assignee: Ciba Geigy CorporationInventors: John D. Spivack, Stephen D. Pastor
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Patent number: 4558071Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.Type: GrantFiled: February 25, 1983Date of Patent: December 10, 1985Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4555405Abstract: Novel substituted N-alkyl-N-sulfenyl-carbamic acid-[2-(4-phenoxyphenoxy)- and 2-(4-phenylthiophenoxy)-ethyl] esters of the formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 -alkyl, R.sub.2 is phenyl, phenyl substituted by 1 or 2 halogen atoms or by 1 or 2 C.sub.1 -C.sub.4 -alkyl groups or is --C(CH.sub.3).sub.2 --C.tbd.N, R.sub.3 is halogen, C.sub.1 -C.sub.4 -alkyl, or C.sub.1 -C.sub.4 -alkyl substituted by up to 3 halogen atoms, A is oxygen or sulfur, and n is zero, 1 or 2; processes for producing this compound; and compositions for use in the control of pests, particularly the control of pests which infest plants and animals. The novel compounds are especially effective as ovicides against insects which damage plants.Type: GrantFiled: June 30, 1983Date of Patent: November 26, 1985Assignee: Ciba Geigy CorporationInventors: Manfred Boger, Jozef Drabek
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Patent number: 4552695Abstract: New route to diltiazem hydrochloride of the formula: ##STR1## in which the starting cinnamyl alcohols are epoxidized by a special asymmetric synthesis followed by a series of stereospecific reactions; no optical resolution is required at any stage.Type: GrantFiled: April 16, 1984Date of Patent: November 12, 1985Assignee: Shionogi & Co., Ltd.Inventors: Kikuo Igarashi, Tsunetoshi Honma
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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: 4540732Abstract: The title compounds correspond to the formula ##STR1## and are useful as stabilizers for organic polymers and lubricating oils to counteract the degradative effects of heat, light and air.Type: GrantFiled: October 31, 1983Date of Patent: September 10, 1985Assignee: Ciba-Geigy CorporationInventors: John D. Spivack, Stephen D. Pastor, Paul Odorisio
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Patent number: 4539159Abstract: An improved process for preparing derivatives of mercaptophenols containing nitrile, carbonyl, sulphone or ester groups characterized by reacting the components in a polar solvent with an amine catalyst. The catalyst can be removed from the product by co-distillation with the solvent to leave a relatively pure product free of contaminant without the need for further purification steps. The preferred amine catalysts are tertiary amines.Type: GrantFiled: April 23, 1984Date of Patent: September 3, 1985Assignee: The Dow Chemical CompanyInventor: Mark R. Johnson
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Patent number: 4537621Abstract: Diphenyl ethers of the formula ##STR1## where Z.sup.1, Z.sup.2, and Z.sup.3 and R have the meanings given in the description, are used for controlling undesirable plant growth.Type: GrantFiled: March 31, 1983Date of Patent: August 27, 1985Assignee: BASF AktiengesellschaftInventors: Adolf Parg, Hans Ziegler, Bruno Wuerzer
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Patent number: 4533676Abstract: A 2,5-dihalogenobenzoyl-(thio)urea of the formula ##STR1## in which X represents sulphur or oxygen,X.sup.1 and X.sup.2 are identical or different and represent fluorine, chlorine, bromine or iodine,R.sup.1 represents hydrogen, halogen, or optionally substituted radicals from the series comprising alkyl, alkoxy and alkylthio,R.sup.2 represents hydrogen, halogen, cyano, nitro or optionally substituted radicals from the series comprising alkyl, alkylthio, alkylsulphonyl, alkoxy, aryloxy, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl and alkoxycarbonylalkylthio,R.sup.1 and R.sup.2 together represent an optionally substituted alkylenedioxy radical or represent --CF.sub.2 --O--CF.sub.2 --O--,R.sup.3 represents hydrogen, halogen, or an optionally substituted alkyl, alkoxy or aryloxy radical, andR.sup.4 represents hydrogen, halogen, or optionally substituted radicals from the series comprising alkyl, alkylthio and alkoxy, with the exception of those cases in which X represents oxygen, X.sup.1 and X.sup.Type: GrantFiled: April 22, 1983Date of Patent: August 6, 1985Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Erich Klauke, Ingeborg Hammann
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Patent number: 4532031Abstract: A process for the recovery of mineral values by froth flotation in an aqueous medium employing a novel frother. Frothers prepared by Michael addition between alpha, beta-unsaturated ethylenic compounds and either alcohols, amines or mercaptans or by the condensation of HCN, aldehydes/ketones with either alcohols, amines or mercaptans have been found to be effective in the froth flotation system and capable of reducing the required collector consumption.Type: GrantFiled: April 21, 1983Date of Patent: July 30, 1985Assignee: American Cyanamid CompanyInventors: Samuel S. Wang, Michael J. Scanlon
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Patent number: 4506083Abstract: Thioxanthonecarboxylic acid esters, thioesters or amides of the formula I ##STR1## in which X and Z are hydrogen or one of the substituents defined in more detail in claim 1 and Y is --OR.sub.1, --SR.sub.1 or --N(R.sub.1)(R.sub.2), in which R.sub.1 is C.sub.1-24 alkyl and R.sub.2 is H or R.sub.1, are suitable, if desired together with amines, as initiators for the photopolymerization of ethylenically unsaturated compounds or for photochemical crosslinking of polyolefines. They are also used an sensitizers for photocrosslinkable polymers. They can be prepared by methods known per se, for example by cyclization of phenylthio-phthalic, -isophthalic or -terephthalic acids, which can be correspondingly substituted, and subsequent reaction with suitable alcohols, thiols or amines.Type: GrantFiled: June 28, 1982Date of Patent: March 19, 1985Assignee: Ciba-Geigy CorporationInventors: Vratislav Kvita, Hans Zweifel, Martin Roth, Louis Felder
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Patent number: 4497959Abstract: Substituted succinic anhydride or succinate stabilizers of the formula I or II ##STR1## where R.sub.1 and R.sub.2 are independently alkyl, cycloalkyl, phenyl or aralkyl, R.sub.3 is hydrogen or methyl, R.sub.4 is hydrogen, lower alkyl or phenyl, R.sub.5 is hydrogen, alkyl, alkylthio, arylthio or the structure ##STR2## and R.sub.6 and R.sub.7 are independently hydrogen, alkyl; aryl or substituted aryl are useful as stabilizers for polymeric substrates, particularly polyolefins and rubber.Type: GrantFiled: February 3, 1983Date of Patent: February 5, 1985Assignee: Ciba-Geigy CorporationInventors: John D. Spivack, Stephen D. Pastor
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Patent number: 4496720Abstract: A novel process for the preparation of thioethers comprising reacting a silylated thiol of the formulaR--S--SiR.sub.1 R.sub.2 R.sub.3 Iwherein R is an organic group and R.sub.1, R.sub.2 and R.sub.3 are individually selected from the group consisting of alkyl of 1 to 4 carbon atoms with an organic halide, sulfate or sulfonate in the presence of hexamethylphosphoric triamide as a solvent or co-solvent preferably under neutral conditions in aprotic solvents at a temperature between 0.degree. and 150.degree. C.Type: GrantFiled: March 7, 1983Date of Patent: January 29, 1985Assignee: Gist-Brocades N.V.Inventors: Cornelis A. Bruynes, Theodorus K. Jurriens
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Patent number: 4487953Abstract: Compounds of Formula (I) ##STR1## wherein the 9-bromine atom can be in the .alpha.- or .beta.-position,R.sub.1 is CH.sub.2 OH or C(O)OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is C(O)NHR.sub.3 wherein R.sub.3 is an acid residue or R.sub.2 ; andA is --CH.sub.2 --CH.sub.2 -- or cis --CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 --, trans --CH.dbd.CH--, or --C.tbd.C--;W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D and E together are a direct bond; orD is straight-chain, branched, or cyclic alkylene of 1-10 carbon atoms, optionally substituted by fluorine atoms; andE is oxygen, sulfur, a direct bond --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 are different from each other and each is hydrogen, chlorine, or C.sub.1 -C.sub.4 -alkyl;R.sub.4 is a free or functionally modified hydroxy group;R.sub.Type: GrantFiled: December 6, 1982Date of Patent: December 11, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger
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Patent number: 4481148Abstract: Hydroxyl-containing liquid polymers having an aliphatic polymeric backbone and sulfide linkages near the terminal portions of the polymer molecule are prepared by polymerizing (1) at least one of selected vinylidene monomers having at least one terminal CH.sub.2 .dbd.C< group per monomer molecule, together with (2) at least one hydroxyl-containing disulfide in the presence of (3) ultraviolet radiation.Type: GrantFiled: March 16, 1981Date of Patent: November 6, 1984Assignee: The B. F. Goodrich CompanyInventor: Changkiu K. Riew
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Patent number: 4473701Abstract: Processes for producing a (1.alpha., 4.alpha., 5.alpha.)-6,6-dimethyl-4-halo-substituted-methyl-3-oxabicyclo[3.1.0]hexan- 2-one and its novel intermediates from known and inexpensive starting materials are described and exemplified.Type: GrantFiled: January 22, 1982Date of Patent: September 25, 1984Assignee: FMC CorporationInventors: Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
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Patent number: 4466977Abstract: Cis- and trans-N-[2-amino(oxy- or thia group-substituted-cycloaliphatic)]benzeneacetamide and -benzamide compounds, e.g., 3,4-dichloro-N-[4,4-dimethoxy-2-(1-pyrrolidinyl)cyclohexyl]-N-methylbenzen eacetamide, and salts thereof, are provided. These compounds have analgesic properties. Processes for their preparation are disclosed. Pharmaceutical compositions and methods of use are also provided.Type: GrantFiled: November 4, 1982Date of Patent: August 21, 1984Assignee: The Upjohn CompanyInventors: Moses W. McMillan, Jacob Szmuszkovicz
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Patent number: 4458091Abstract: Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.Type: GrantFiled: September 30, 1982Date of Patent: July 3, 1984Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4456766Abstract: The subject matter of the invention is a process for the production of N-acetyl-2,3-dehydroaminocarboxylic acid esters by reaction of the corresponding 2-azido-carboxylic acid esters with a mixture of one part by volume of acetic anhydride and 1.5 to 5 parts by volume of acetic acid in the presence of rhenium VII sulfide and/or oxide and at a temperature between 50.degree. and 150.degree. C., in a given case, in the simultaneous presence of dry hydrogen chloride.Type: GrantFiled: September 16, 1982Date of Patent: June 26, 1984Assignee: Degussa AktiengesellschaftInventors: Franz Effenberger, Thomas Beisswenger
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Patent number: 4454339Abstract: 9-Fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.-position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.Type: GrantFiled: July 6, 1982Date of Patent: June 12, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4454338Abstract: Amidino compounds represented by the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and antithrombin agents. Having strong anti-C1 (C1r, C1s) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula ##STR2## with 6-amidino-2-naphthol and, if necessary, can be transformed into pharmaceuticlly acceptable acid addition salts thereof.Type: GrantFiled: September 9, 1981Date of Patent: June 12, 1984Assignee: Torii & Co., Ltd.Inventors: Setsuro Fujii, Toshiyuki Okutome, Toyoo Nakayama, Takashi Yaegashi, Masateru Kurumi
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Patent number: 4450172Abstract: Polyhalohydroxyisopropyl phenylalka(e)noic acid esters of alkylaminohydroxypropyloxyphenylalkyl alcohols, such as 2-(4-((2-hydroxy-3-(1-methylethylamino)-phenyl)ethyl 3-(4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethylethyl))benzene propanoate, are useful as antihypertensive agents. Preferred compounds give vasodilatory activity and reduced tachycardia.Type: GrantFiled: March 10, 1982Date of Patent: May 22, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Sung-eun Yoo
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Patent number: 4446264Abstract: Compounds prepared by reacting maleic anhydride, maleic acid or their esters with thiols; which exhibit a synergistic effect when combined with a phenolic antioxidant in the stabilization of organic materials such as natural and synthetic polymers, rubbers, lubricants and oil, etc. are disclosed.Type: GrantFiled: April 15, 1982Date of Patent: May 1, 1984Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4443248Abstract: This invention discloses novel herbicidal compounds of the formula ##STR1## wherein X is selected from the group consisting of halogen, nitro, cyano and trifluoromethyl; Y is selected from the group consisting of hydrogen, halogen, nitro and cyano; R.sup.1 is alkyl; R.sup.2 is selected the group consisting of hydrogen and alkyl; and R.sup.3 is selected from the group consisting of hydroxy, alkoxy, alkylthio, amino, alkylamino and dialkylamino and further herbicidal compositions and methods using said compounds.Type: GrantFiled: April 12, 1982Date of Patent: April 17, 1984Assignee: Velsicol Chemical CorporationInventor: Takeo Hokama
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Patent number: 4432885Abstract: Decalins of the formula ##STR1## wherein ring A is aromatic or a trans-1,4-disubstituted cyclohexane ring; R.sup.2 is methyl, --CH.sub.2 R', --OR', --CO--R', --CN, --COOH, --CO--OR', --CO--SR' or --O--CO--R'; R.sup.1 is hydrogen, methyl, --CH.sub.2 R, --OR or --CH.sub.2 OR, or when R.sup.2 is methyl, --CH.sub.2 R', --OR' or --CO--R', R.sup.1 also can be --CN, --COOH, --CO--OR, --CO--SR or --O--CO--R; R and R' each are alkyl; and R.sup.1 and R.sup.2 each have up to 12 carbon atoms and together have at most 14 carbon atoms,their racemates and optically active antipodes, are described. Liquid crystalline mixtures comprising Compound I as well as their use in electro-optical devices also are disclosed.Type: GrantFiled: December 9, 1981Date of Patent: February 21, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Kuno Schleich
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Patent number: 4430345Abstract: Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.Type: GrantFiled: September 30, 1982Date of Patent: February 7, 1984Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4425360Abstract: The present invention provides pyruvic acid oximes of the general formula: ##STR1## wherein R is a hydrogen atom, a C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.6 alkoxy, cinnamyloxy, phenylamino, phenyl-N-alkylamino or phenylthio radical or an aryl or aryloxy radical, the aryl moiety of which can be substituted one or more times by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen, hydroxyl, trifluoromethyl, amino, acetylamino, nitrile, nitro or methylenedioxy, A is a straight-chained or branched, saturated or unsaturated aliphatic hydrocarbon chain containing up to 10 carbon atoms, which can be substituted one or more times by halogen or hydroxyl, and R.sub.1 is a C.sub.1 -C.sub.8 alkyl radical, which can be substituted one or more times by halogen, hydroxyl, nitrile, phenyl or carboxyl, or is a nitrile or formyl group, with the proviso that when R--A-- is a methyl or ethyl radical, R.sub.1 is not a methyl radical or a nitrile group and when R--A-- is a benzyl radical, R.sub.Type: GrantFiled: September 8, 1981Date of Patent: January 10, 1984Assignee: Boehringer Mannheim GmbHInventors: Hans P. Wolff, Ruth Heerdt, Manfred Hubner, deceased, Hans Kuhnle, Felix H. Schmidt
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Patent number: 4423063Abstract: 2,4-Dioxo-4-substituted-1-butanoic acid derivatives of the formula: ##STR1## where R is hydrogen or C.sub.1-4 alkyl; andL is a lipophilic group consisting essentially of ##STR2## where R' is (a) hydrogen; (b) C.sub.1-3 alkyl; (c) benzyl; (d) pyridyl C.sub.1-3 alkyl or (e) (3,4-dihydro-3-hydroxy-2H-1,5-benzodioxepin-3-yl) methyl; provided that positions 2 and 6 of the substituted phenyl moiety may not be substituted; or ##STR3## where R' has the same meaning as above; or a pharmaceutically acceptable salt thereof; useful in treating urinary tract, especially renal calcium oxalate lithiasis.Type: GrantFiled: March 5, 1982Date of Patent: December 27, 1983Assignee: Merck & Co., Inc.Inventors: Clarence S. Rooney, Haydn W. R. Williams, Edward J. Gragoe, Jr., Arthur A. Patchett
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Patent number: 4420628Abstract: A threo-2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionic ester of the formula: ##STR1## wherein R is an ester residue, is prepared by condensing a trans-3-(4-methoxyphenyl)glycidic ester of the formula: ##STR2## wherein R is the same as defined above, with 2-nitrothiophenol in the presence of a Lewis acid.Type: GrantFiled: February 8, 1982Date of Patent: December 13, 1983Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Hirozumi Inoue, Tomiki Hashiyama
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Patent number: 4406902Abstract: Novel chemical compounds are provided which selectively inhibit the metabolism of dipeptidase (E.C.3.4.13.11) and therefore are useful in combination with antibacterial products. These chemical compounds are Z-2-(2,2-dimethylcyclo-propanecarboxamido)-.omega.-pyridylthio-2-alkenoic acids (and related arylthio and heterocyclylthio analogs).Type: GrantFiled: July 23, 1981Date of Patent: September 27, 1983Assignee: Merck & Co., Inc.Inventors: Wallace T. Ashton, Louis Barash, Jeannette E. Brown, Donald W. Graham
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Patent number: 4395566Abstract: An improved process for exterifying carboxyaromatics is disclosed wherein an anhydride of a carboxyaromatic, such as pyromellitic dianhydride, is reacted with a fluorinated alcohol and an epoxide to give a mixed ester capable of imparting oil and/or water repellency to textiles. The improvement comprises utilizing the epoxide as the reaction medium to reduce reaction times and waste water treatment requirements.Type: GrantFiled: March 8, 1982Date of Patent: July 26, 1983Assignee: American Hoechst CorporationInventors: James H. Covill, Michael G. Kelly, Thomas F. Leahy
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Patent number: 4389416Abstract: Described are compounds of the formula ##STR1## wherein R is hydrogen, loweralkyl, aminomethyl or halo; R.sub.1 is carboxy, carboxyloweralkyl, aminocarbonyl, hydroxymethyl, anilinomethyl, or aminomethyl; A is oxygen, CH.sub.2, Sulfur or a single bond; X is oxygen, CH.sub.2, sulfur or sulfoxide; and Y is hydrogen, loweralkyl or halo and may be the same or different, and pharmaceutically acceptable salts thereof.The compounds are effective as diuretic agents.Type: GrantFiled: October 9, 1981Date of Patent: June 21, 1983Assignee: Abbott LaboratoriesInventor: Jacob J. Plattner
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Patent number: RE32215Abstract: 2-nitro-5-(substituted-phenoxy)benzoic acids and esters, salts, amides, and acyl halides thereof comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: February 23, 1983Date of Patent: July 22, 1986Assignee: Rhone-Poulenc AgrochimieInventor: Robert J. Theissen
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Patent number: RE32216Abstract: 2-Nitro-5-(substituted-phenoxy)benzoic acids and esters, salts, amides, and acyl halides thereof comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: February 23, 1983Date of Patent: July 29, 1986Assignee: Rhone-Poulenc AgrochimieInventor: Robert J. Theissen
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Patent number: RE32243Abstract: 2-Nitro-5-(substituted-phenoxy)benzoic acids and esters, salts, amides, and acyl halides thereof comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: February 23, 1983Date of Patent: September 9, 1986Assignee: Rhone-Poulenc AgrochimieInventor: Robert J. Theissen