Sulfur, Bonded Directly To A Ring, In Same Side Chain As Ester Function Patents (Class 560/17)
  • Patent number: 4681971
    Abstract: 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: Grant
    Filed: November 1, 1985
    Date of Patent: July 21, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Johannes Pfenninger, Abul Iqbal, Alain C. Rochat
  • Patent number: 4670577
    Abstract: 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: Grant
    Filed: February 24, 1984
    Date of Patent: June 2, 1987
    Assignee: Roussel Uclaf
    Inventors: Marc Julia, Therese Cuvigny
  • Patent number: 4670470
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: June 2, 1987
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4661617
    Abstract: Substituted alkenoates and alkanoates, intermediates therefor, synthesis thereof, and their use for the control of pests.
    Type: Grant
    Filed: April 19, 1985
    Date of Patent: April 28, 1987
    Assignee: Sandoz Ltd.
    Inventor: Clive A. Henrick
  • Patent number: 4661515
    Abstract: 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: Grant
    Filed: January 17, 1986
    Date of Patent: April 28, 1987
    Assignee: USV Pharmaceutical Corporation
    Inventors: Edward S. Neiss, John T. Suh, John J. Piwinski
  • Patent number: 4659855
    Abstract: Certain novel aryl sulfonyl fluorides, their preparation, and their use in inhibiting serine proteases with chymotrypsin-like and elastase-like specificity.
    Type: Grant
    Filed: May 9, 1983
    Date of Patent: April 21, 1987
    Assignee: Georgia Tech Research Corporation
    Inventor: James C. Powers
  • Patent number: 4647585
    Abstract: 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: Grant
    Filed: November 8, 1984
    Date of Patent: March 3, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Melanie J. Loots, Steven E. Hall, Peter W. Sprague
  • Patent number: 4634728
    Abstract: 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: Grant
    Filed: August 20, 1985
    Date of Patent: January 6, 1987
    Assignee: Mallinckrodt, Inc.
    Inventors: Neil Dunski, Ali A. Bazzi, Henry J. Buehler
  • Patent number: 4634715
    Abstract: 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: Grant
    Filed: July 27, 1983
    Date of Patent: January 6, 1987
    Assignee: Merck & Co., Inc.
    Inventors: William J. Greenlee, Eugene D. Thorsett
  • Patent number: 4633013
    Abstract: 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: Grant
    Filed: June 11, 1984
    Date of Patent: December 30, 1986
    Assignee: Eastman Kodak Company
    Inventor: Robert J. Clemens
  • Patent number: 4629737
    Abstract: 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: Grant
    Filed: July 14, 1983
    Date of Patent: December 16, 1986
    Assignee: Beecham Group p.l.c.
    Inventor: Barrie C. C. Cantello
  • Patent number: 4604417
    Abstract: 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: Grant
    Filed: December 10, 1984
    Date of Patent: August 5, 1986
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Kirkwood S. Cottman
  • Patent number: 4596823
    Abstract: 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: Grant
    Filed: February 12, 1982
    Date of Patent: June 24, 1986
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4595687
    Abstract: 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: Grant
    Filed: July 18, 1984
    Date of Patent: June 17, 1986
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Douglas W. Beight, Gary A. Flynn
  • Patent number: 4582913
    Abstract: 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: Grant
    Filed: June 11, 1984
    Date of Patent: April 15, 1986
    Assignee: Eastman Kodak Company
    Inventor: Robert J. Clemens
  • Patent number: 4559379
    Abstract: 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: Grant
    Filed: February 5, 1985
    Date of Patent: December 17, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: John D. Spivack, Stephen D. Pastor
  • Patent number: 4558071
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: February 25, 1983
    Date of Patent: December 10, 1985
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4555405
    Abstract: 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: Grant
    Filed: June 30, 1983
    Date of Patent: November 26, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: Manfred Boger, Jozef Drabek
  • Patent number: 4552695
    Abstract: 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: Grant
    Filed: April 16, 1984
    Date of Patent: November 12, 1985
    Assignee: Shionogi & Co., Ltd.
    Inventors: Kikuo Igarashi, Tsunetoshi Honma
  • Patent number: 4542233
    Abstract: Improvement in the process for preparing biaryl compounds via coupling of an arylamine with an arene in the presence of a nitrite, an acid and copper metal or a derivative thereof; the improvement is consisting in adding to the reaction mixture a trialkylorthoformate. The process may be used for preparing drugs such as Flurbiprofen and Xenbucin or intermediate compounds particularly useful for preparing Flurbiprofen, Flufenisal, Chlordimorin, Xenbucin, Xenysalate, Xenyhexenic acid and the like.
    Type: Grant
    Filed: July 20, 1983
    Date of Patent: September 17, 1985
    Assignee: Biaschim S.p.A.
    Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio
  • Patent number: 4540732
    Abstract: 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: Grant
    Filed: October 31, 1983
    Date of Patent: September 10, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: John D. Spivack, Stephen D. Pastor, Paul Odorisio
  • Patent number: 4539159
    Abstract: 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: Grant
    Filed: April 23, 1984
    Date of Patent: September 3, 1985
    Assignee: The Dow Chemical Company
    Inventor: Mark R. Johnson
  • Patent number: 4537621
    Abstract: 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: Grant
    Filed: March 31, 1983
    Date of Patent: August 27, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Adolf Parg, Hans Ziegler, Bruno Wuerzer
  • Patent number: 4533676
    Abstract: 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: Grant
    Filed: April 22, 1983
    Date of Patent: August 6, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Erich Klauke, Ingeborg Hammann
  • Patent number: 4532031
    Abstract: 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: Grant
    Filed: April 21, 1983
    Date of Patent: July 30, 1985
    Assignee: American Cyanamid Company
    Inventors: Samuel S. Wang, Michael J. Scanlon
  • Patent number: 4506083
    Abstract: 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: Grant
    Filed: June 28, 1982
    Date of Patent: March 19, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Vratislav Kvita, Hans Zweifel, Martin Roth, Louis Felder
  • Patent number: 4497959
    Abstract: 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: Grant
    Filed: February 3, 1983
    Date of Patent: February 5, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: John D. Spivack, Stephen D. Pastor
  • Patent number: 4496720
    Abstract: 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: Grant
    Filed: March 7, 1983
    Date of Patent: January 29, 1985
    Assignee: Gist-Brocades N.V.
    Inventors: Cornelis A. Bruynes, Theodorus K. Jurriens
  • Patent number: 4487953
    Abstract: 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: Grant
    Filed: December 6, 1982
    Date of Patent: December 11, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger
  • Patent number: 4481148
    Abstract: 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: Grant
    Filed: March 16, 1981
    Date of Patent: November 6, 1984
    Assignee: The B. F. Goodrich Company
    Inventor: Changkiu K. Riew
  • Patent number: 4473701
    Abstract: 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: Grant
    Filed: January 22, 1982
    Date of Patent: September 25, 1984
    Assignee: FMC Corporation
    Inventors: Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
  • Patent number: 4466977
    Abstract: 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: Grant
    Filed: November 4, 1982
    Date of Patent: August 21, 1984
    Assignee: The Upjohn Company
    Inventors: Moses W. McMillan, Jacob Szmuszkovicz
  • Patent number: 4458091
    Abstract: 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: Grant
    Filed: September 30, 1982
    Date of Patent: July 3, 1984
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4456766
    Abstract: 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: Grant
    Filed: September 16, 1982
    Date of Patent: June 26, 1984
    Assignee: Degussa Aktiengesellschaft
    Inventors: Franz Effenberger, Thomas Beisswenger
  • Patent number: 4454339
    Abstract: 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: Grant
    Filed: July 6, 1982
    Date of Patent: June 12, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
  • Patent number: 4454338
    Abstract: 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: Grant
    Filed: September 9, 1981
    Date of Patent: June 12, 1984
    Assignee: Torii & Co., Ltd.
    Inventors: Setsuro Fujii, Toshiyuki Okutome, Toyoo Nakayama, Takashi Yaegashi, Masateru Kurumi
  • Patent number: 4450172
    Abstract: 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: Grant
    Filed: March 10, 1982
    Date of Patent: May 22, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Sung-eun Yoo
  • Patent number: 4446264
    Abstract: 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: Grant
    Filed: April 15, 1982
    Date of Patent: May 1, 1984
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Kirkwood S. Cottman
  • Patent number: 4443248
    Abstract: 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: Grant
    Filed: April 12, 1982
    Date of Patent: April 17, 1984
    Assignee: Velsicol Chemical Corporation
    Inventor: Takeo Hokama
  • Patent number: 4432885
    Abstract: 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: Grant
    Filed: December 9, 1981
    Date of Patent: February 21, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Petrzilka, Kuno Schleich
  • Patent number: 4430345
    Abstract: 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: Grant
    Filed: September 30, 1982
    Date of Patent: February 7, 1984
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4425360
    Abstract: 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: Grant
    Filed: September 8, 1981
    Date of Patent: January 10, 1984
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hans P. Wolff, Ruth Heerdt, Manfred Hubner, deceased, Hans Kuhnle, Felix H. Schmidt
  • Patent number: 4423063
    Abstract: 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: Grant
    Filed: March 5, 1982
    Date of Patent: December 27, 1983
    Assignee: Merck & Co., Inc.
    Inventors: Clarence S. Rooney, Haydn W. R. Williams, Edward J. Gragoe, Jr., Arthur A. Patchett
  • Patent number: 4420628
    Abstract: 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: Grant
    Filed: February 8, 1982
    Date of Patent: December 13, 1983
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Hirozumi Inoue, Tomiki Hashiyama
  • Patent number: 4406902
    Abstract: 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: Grant
    Filed: July 23, 1981
    Date of Patent: September 27, 1983
    Assignee: Merck & Co., Inc.
    Inventors: Wallace T. Ashton, Louis Barash, Jeannette E. Brown, Donald W. Graham
  • Patent number: 4395566
    Abstract: 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: Grant
    Filed: March 8, 1982
    Date of Patent: July 26, 1983
    Assignee: American Hoechst Corporation
    Inventors: James H. Covill, Michael G. Kelly, Thomas F. Leahy
  • Patent number: 4389416
    Abstract: 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: Grant
    Filed: October 9, 1981
    Date of Patent: June 21, 1983
    Assignee: Abbott Laboratories
    Inventor: Jacob J. Plattner
  • Patent number: RE32215
    Abstract: 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: Grant
    Filed: February 23, 1983
    Date of Patent: July 22, 1986
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Robert J. Theissen
  • Patent number: RE32216
    Abstract: 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: Grant
    Filed: February 23, 1983
    Date of Patent: July 29, 1986
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Robert J. Theissen
  • Patent number: RE32243
    Abstract: 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: Grant
    Filed: February 23, 1983
    Date of Patent: September 9, 1986
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Robert J. Theissen