Polycarboxylic Acid Patents (Class 560/54)
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Patent number: 5041638Abstract: An alkenoic acid derivative of the formula ##STR1## in which X and Y are identical or different and represent sulfur, sulfoxide, sulfone, an alkylene chain, --SCH.sub.2 --, or oxygen or a direct bond,W represents --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,o represents a number 1 to 5,A and B are identical or different and represent carboxyl, carboxymethylene, tetrazolyl or tetrazolylmethylene, or --CO.sub.2 R.sup.9 or --CH.sub.2 CO.sub.2 R.sup.9 or --CONR.sup.10 R.sup.11 or nitrilen represents a number 1 to 10,m represents a number 0 to 7,T and Z are identical or different and represent oxygen or a direct bond andR.sup.2, R.sup.3, R.sup.8 are identical or different and represent hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, trifluoromethoxy, cyano or nitro andR.sup.9 is lower alkyl and R.sup.10 and R.sup.11 are hydrogen, lower alkyl, alkylsulfonyl or arylsulfonyl or together are an alkylene chain to form a ringand pharmaceutically acceptable salts thereof.Type: GrantFiled: May 9, 1989Date of Patent: August 20, 1991Assignee: Bayer AktiengesellschaftInventors: Ulrich Rosentreter, Harold C. Kluender, Trevor S. Abram, Peter Norman, Steven R. Tudhope
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Patent number: 5039308Abstract: Additives which improve the low-temperature properties of distillate fuels are the reaction products of (1) diaminodiols, and (2) the product of benzophenone tetracarboxylic dianhydride and aminoalcohols and/or amines with long-chain hydrocarbyl groups attached.Type: GrantFiled: December 13, 1989Date of Patent: August 13, 1991Assignee: Mobil Oil CorporationInventors: David J. Baillargeon, Angeline B. Cardis, Dale B. Heck
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Patent number: 5039672Abstract: Certain spirocyclic heterocyclic compounds, and their pharmaceutically-acceptable salts, are inhibitors of the aldose reductase enzyme, and so are useful for the control of diabetic complications. Exemplary compounds include compounds of the formula ##STR1## wherein Y is ##STR2## X is --O-- or ##STR3## R.sub.1 and R.sub.2 are each independently H, alkyl C.sub.1 -C.sub.6,aryl or arylalkyl (C.sub.1 -C.sub.6);W.sub.1 and W.sub.2 are each independently hydrogen, halogen or nitro; andthe pharmaceutically acceptable base addition salts thereof.Type: GrantFiled: April 5, 1990Date of Patent: August 13, 1991Assignee: Pfizer Inc.Inventors: James F. Eggler, Eric R. Larson
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Patent number: 4997973Abstract: Benzyl carboxylates of the formula ##STR1## where R.sup.1 is alkyl,R.sup.2 is hydrogen, alkyl or alkoxy,R.sup.3 is hydrogen, halogen, cyano, aryl or aryloxy, the aromatic ring being unsubstituted or substituted, or R.sup.3 is heteroaryl, adamantyl, fluorenyl or cycloalkyl or cycloalkenyl, the radicals being unsubstituted or substituted,X is saturated or unsaturated, substituted or unsubstituted alkylene, andn is 0 or 1, and fungicides containing these compounds.Type: GrantFiled: March 14, 1989Date of Patent: March 5, 1991Assignee: BASF AktiengesellschaftInventors: Bernd Wenderoth, Siegbert Brand, Franz Schuetz, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
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Patent number: 4997591Abstract: The chiral smetic liquid-crystalline compounds of the general formula (I)M.sub.1.sup.* --B--M.sub.2.sup.* (I)solidify on cooling from the liquid-crystalline phase in glassy form, as a result of which they are suitable for materials for displaying and storing information. Such materials may be used in electro-optic data stores or display components which are based on the ferroelectric or electroclinic switching effect in a chiral or chirally doped, smetic liquid-crystalline phase.In the general formula, M.sub.1.sup.*, M.sub.2.sup.* stand for chiral smetogenic groups and --B-- is, as bridging link, a typical bivalent group.Type: GrantFiled: August 11, 1989Date of Patent: March 5, 1991Assignee: Hoechst AktiengesellschaftInventors: Gerd Heppke, Feodor Oestreicher
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Patent number: 4994610Abstract: Fluorinated benzoyl compounds of the formula: ##STR1## wherein Q is a lower alkyl group, a halogen atom, --CH.sub.2 CO.sub.2 R.sup.1 wherein R.sup.1 is a lower alkyl group, or ##STR2## wherein each of R.sup.2 and R.sup.3 is a lower alkyl group, are disclosed.Type: GrantFiled: December 5, 1989Date of Patent: February 19, 1991Assignee: Asahi Glass Company, Ltd.Inventors: Seisaku Kumai, Osamu Yokokoji, Akihiro Tamaoki
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Patent number: 4889947Abstract: Sunscreen compositions are described which contain certain substituted naphthalenylidenes which act as UV filters when incorporated in a carrier in amounts ranging from 0.1-50% by weight.Type: GrantFiled: July 28, 1988Date of Patent: December 26, 1989Assignee: ICI Americas Inc.Inventors: Charalambos J. Phalangas, Thomas P. Cleary
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Patent number: 4826982Abstract: Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen atom or lower alkyl group; the hydrates or the pharmaceutically acceptable acid addition or alkali salts thereof are useful as an antibacterial agent.Type: GrantFiled: September 2, 1986Date of Patent: May 2, 1989Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Kuniyoshi Masuzawa, Seigo Suzue, Keiji Hirai, Takayoshi Ishizaki
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Patent number: 4808338Abstract: Intermediate compounds of the formula ##STR1## wherein X is oxy, thio, sulfinyl or sulfonyl; R is halogen; C.sub.1 C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; trifluoromethyl or difluoromethyl; R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, or phenyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene; R.sup.3 hydrogen, C.sub.1 C.sub.4 alkyl, or phenyl with the proviso that R.sup.1 and R.sup.3 are not both phenyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, or phenyl; R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.Type: GrantFiled: February 1, 1988Date of Patent: February 28, 1989Assignee: Stauffer Chemical CompanyInventor: David L. Lee
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Patent number: 4803294Abstract: This invention relates to novel intermediate compounds which are useful for producing the halogenated protease inhibitors that are the subject matter of U.S. Pat. No. 4,469,885. In particular, the invention relates to novel methods and intermediates for making said protease inhibitors, the intermediate compounds being of the formula: ##STR1## wherein R.sub.1 is: (a) straight or branched chain lower alkyl having 1-6 carbon atoms; or(b) H;wherein R.sub.6 is:(a) straight or branched chain higher alkyl having 13-25 carbon atoms; or(b) straight or branched chain higher alkenyl having 13-25 carbon atoms;wherein R.sub.5 is:(a) straight or branched chain lower alkyl having 1-6 carbon atoms; or(b) benzyl;wherein R.sub.7 is:(a) straight or branched chain lower alkyl having 1-6 carbon atoms; or(b) H;wherein R.sub.2 is:(a) --Cl, --Br, or --I; or(b) --CF.sub.3.Type: GrantFiled: October 29, 1987Date of Patent: February 7, 1989Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 4800231Abstract: Novel keto-diesters are produced by a 2:1 condensation of lower alkyl esters of .alpha.,.beta.-ethylenically unsaturated carboxylic acids and aldehydes having two hydrogen atoms as portions of a formyl group, in the presence of a thiazolium salt as catalyst and a tertiary amine.Type: GrantFiled: March 23, 1988Date of Patent: January 24, 1989Assignee: Shell Oil CompanyInventor: Pen C. Wang
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Patent number: 4788320Abstract: The present invention is concerned with certain novel benzoylacetic acid ester derivatives (I) which are useful as a intermediates for synthesis of antibacterial agests. ##STR1## wherein R is a lower alkyl group, X is a halogen atom and Y is a chlorine or bromine atom.Type: GrantFiled: January 16, 1987Date of Patent: November 29, 1988Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Tsutomu Irikura, Seigo Suzue, Satoshi Murayama, Keiji Hirai, Takayoshi Ishizaki
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Patent number: 4762844Abstract: Alkyl-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids of the formula ##STR1## in which X.sup.1, X.sup.2 and X.sup.3 each independently is hydrogen, a nitro group, a halogen atom or an alkyl radical with 1 to 3 carbon atoms, with the proviso that at least one of them is an alkyl radical,or pharmaceutically acceptable salts or hydrates thereof, are antibacterially active and promote animal growth.Type: GrantFiled: November 5, 1985Date of Patent: August 9, 1988Assignee: Bayer AktiengesellschaftInventors: Klaus Grohe, Michael Schriewer, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4724263Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m --wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl or ethyl;R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.Type: GrantFiled: June 9, 1986Date of Patent: February 9, 1988Assignee: Stauffer Chemical CompanyInventor: Charles G. Carter
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Patent number: 4656305Abstract: The present invention provides chalcone derivatives of the general formulae: ##STR1## wherein R.sub.1 is a hydroxyl, carboxylic or sulphonic acid group or a carboxyalkoxy or sulphoalkoxy radical, R.sub.2 is an unsaturated, straight-chained or branched aliphatic hydrocarbonyloxy radical, R.sub.3 is a hydrogen atom, a hydroxyl group or an alkoxy radical, R.sub.4 is an alkyl, hydroxyalkyl, alkoxy, carboxyalkoxy, sulphoalkoxy or carboxyalkylcarbonyloxyalkyl radical or a carboxylic acid or sulphonic acid group and R.sub.5 is a hydrogen or halogen atom, with the proviso that compounds of general formula (IIa) always contain at least one carboxylic or sulphonic acid group; and the nontoxic inorganic and organic salts of those compounds containing at least one carboxylic acid or sulphonic acid group.The present invention also provides a process for the preparation of these chalcone derivatives, as well as pharmaceutical compositions containing them.Type: GrantFiled: October 18, 1985Date of Patent: April 7, 1987Assignee: Biorex Laboratories, LimitedInventors: Anthony E. Vanstone, Graham K. Maile, Lynn K. Nalbantoglu
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Patent number: 4654434Abstract: The invention relates to new 3-benzylidene-camphor derivatives of the formula: ##STR1## in which R.sub.1 denotes H or SO.sub.3.sup..crclbar. M.sup..sym., with M=H, an alkali metal or N.sup..sym. (R.sub.3).sub.4, with R.sub.3 =H or C.sub.1 -C.sub.4 alkyl or hydroxyalkyl; R.sub.2 denotes C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and n=0-4; and Z denotes ##STR2## in which R.sub.4 has the same meaning as R.sub.1 and can be identical or different, or alternatively ##STR3## in which R.sub.5 denotes H, optionally substituted aryl, C.sub.1 -C.sub.4 alkyl, --CN, --C00R7 or ##STR4## and R.sub.6 denotes --COOR.sub.8 or ##STR5## in which R.sub.7 and R.sub.8, which are identical or different, denote alkyl, alkenyl, cycloalkyl or aralkyl and R.sub.9 and R.sub.10, which are identical or different, denote H, alkyl, alkenyl or cycloalkyl; if R.sub.5 =H, alkyl or aryl, R.sub.6 can represent --COO.sup..crclbar. M.sup..sym.Type: GrantFiled: February 4, 1986Date of Patent: March 31, 1987Assignee: L'OrealInventors: Gerard Lang, Madeleine Leduc, Alain Malaval
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Patent number: 4545934Abstract: Process for the production of 4-substituted acetoacetic acid derivatives. An acetoacetic acid derivative having the formula: ##STR1## wherein R is alkoxy having 1 to 6 C atoms, phenoxy, --NR'.sub.2, wherein R' is alkyl having 1 to 6 C atoms or aryl, or NR'.sub.2, which is azetidine, pyrrolidine or piperidine, is treated with a secondary amine at an elevated temperature and in the presence of an organic solvent. The water formed is separated. The intermediate is converted into the corresponding 3-enamine carboxylic acid derivative. The derivative is converted by treatment with sodium amide in liquid ammonia into the corresponding sodium salt. The sodium salt is converted by treatment with a halogen compound having the formula R.sub.1 CH.sub.2 X or R.sub.1 R.sub.2 CHX, wherein R.sub.1 and R.sub.2 each are alkyl, alkenyl, alkinyl or aryl and X is chlorine, bromine or iodide, into the corresponding 4-substituted enamino derivative. The derivative is hydrolyzed into the 4-substituted acetoacetic acid derivative.Type: GrantFiled: March 21, 1984Date of Patent: October 8, 1985Assignee: Lonza Ltd.Inventors: Felix Previdoli, Leander Tenud
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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: 4518612Abstract: There are described compounds of formula I, ##STR1## in which Ra, Rb, Rc, Rd, Re, Rf and Rg, which may be the same or different, each represent hydrogen, amino, hydroxy, alkoxy, alkenyloxy, halogen, acyl, alkenyl, alkyl, or alkoxy substituted by phenyl,Rh is hydrogen, alkyl or --COOH.X is a hydrocarbon chain containing from 2 to 10 carbon atoms and optionally substituted by a hydroxy group,A has no significance or represents Y, OY, or SY and Y represents a C 1 to 4 hydrocarbon chain which is optionally substituted by alkyl C 1 to 4,E and G, which may be the same or different, each represent --O--, --S-- or --CH.sub.2 --, provided that at least one of E and G is --O-- or --S--,L, together with the carbon atoms to which it is attached, forms a benzene, furan, thiophene, pyrrole, or pyran-2-one ring,and pharmaceutically acceptable derivatives thereof.Type: GrantFiled: December 21, 1983Date of Patent: May 21, 1985Assignee: Fisons plcInventors: John R. Bantick, John Fuher, David N. Hardern, Thomas B. Lee
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Patent number: 4371547Abstract: 2-Benzylideneglutaraldehydes of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or a substituent selected from the group consisting of halo, lower-alkyl, phenyl, carboxy, lower-alkoxycarbonyl, phenoxycarbonyl, aminocarbonyl, hydroxysulfonyl, nitro, cyano, hydroxy, lower-alkoxy and phenoxy, a method of use thereof as disinfectants, disinfectant compositions comprising them, and 2,6-dialkoxy-3-(.alpha.-alkoxybenzyl)tetrahydropyrans of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are as defined above and R.sup.4 and R.sup.5 independently are alkyl of one to four carbon atoms, which are intermediates for their preparation are disclosed.Type: GrantFiled: August 21, 1981Date of Patent: February 1, 1983Assignee: Sterling Drug Inc.Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
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Patent number: 4316045Abstract: A process for the catalytic preparation of aryl carboxylates is provided in which an arylmetallo carboxylate is contacted in liquid medium with an organic peracid in the presence of a catalytic amount of an aryl iodide, to form the desired aryl carboxylate.Type: GrantFiled: August 29, 1980Date of Patent: February 16, 1982Assignee: The Halcon SD Group, Inc.Inventor: Lawrence C. Costa
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Patent number: 4316046Abstract: A process for the preparation of aryl carboxylates is provided in which an arylmetallo carboxylate is contacted with an aryliodoso carboxylate in liquid medium to form the desired aryl carboxylate. Promoters can be employed to increase the rate of reaction and improve selectivity to the aryl carboxylate.Type: GrantFiled: August 29, 1980Date of Patent: February 16, 1982Assignee: The Halcon SD Group, Inc.Inventor: Lawrence C. Costa
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Patent number: 4313956Abstract: Novel, transient prodrug forms of the phenolic dihydroxy sympathomimetic amines have (i) the structural formula (I): ##STR1## wherein X is O, S or NR.sup.5 ; n is 1 or 2; R.sup.1 is the monodehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 1, and the didehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 2; R.sup.Type: GrantFiled: December 28, 1979Date of Patent: February 2, 1982Assignee: INTERx Research Corp.Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4311706Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.Type: GrantFiled: January 22, 1980Date of Patent: January 19, 1982Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4308394Abstract: Compounds added to initiate photopolymerization of monomers to produce polymeric coatings include compounds of the formula ##STR1## wherein Ar is phenyl or naphthyl,R is hydrogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, halogen, dialkylamino with 1-4 carbon atoms in each alkyl group, carboxyl, or alkoxycarbonyl with 1-4 carbon atoms in the alkoxy group,X is alkyl having 3 to 6 carbon atoms or alkyl having 6 to 72 carbon atoms interrupted by at least one member selected from the group consisting of ##STR2## and the precursor of X being a polyol having 3 to 6 hydroxyls and having a hydroxyl number of from 100 to 1850,R.sub.1 is hydrogen or methyl,n is a number with a value from about 2 to about 5, andn+m is a number with a value from about 3 to about 6.Type: GrantFiled: June 8, 1979Date of Patent: December 29, 1981Assignee: Bayer AktiengesellschaftInventors: Karl-Ernst Shuster, Hans Rudolph, Wolfram Mayer, Hans J. Rosenkranz
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Patent number: 4301186Abstract: This invention relates to new ammonium salts of .alpha.-ketocarboxylic acids, to their use for the production of amines in situ by photochemical decomposition and to photochemically hardenable coating compositions containing these ammonium salts.Type: GrantFiled: June 28, 1979Date of Patent: November 17, 1981Assignee: Bayer AktiengesellschaftInventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder
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Patent number: 4283414Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.Type: GrantFiled: June 8, 1979Date of Patent: August 11, 1981Assignee: ICI Australia LimitedInventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
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Patent number: 4266074Abstract: Substituted acetate compounds represented by the formula ##STR1## which are useful as pesticides and pesticidal composition containing the substituted acetate compounds as active ingredients, as well as processes for preparing the compounds and the compositions are disclosed.Type: GrantFiled: July 16, 1975Date of Patent: May 5, 1981Assignee: Sumitomo Chemical Company LimitedInventors: Keimei Fujimoto, Nobuo Ohno, Yoshitoshi Okuno, Toshio Mizutani, Isao Ohno, Masachika Hirano, Nobushige Itaya, Takashi Matsuo
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Patent number: 4263212Abstract: The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.Type: GrantFiled: February 14, 1980Date of Patent: April 21, 1981Assignee: Rikagaku KenkyushoInventors: Pangbu Hong, Hiroshi Yamazaki
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Patent number: 4249021Abstract: Substituted 1-oxo-2,2-disubstituted-5-indanacetic acids and their salts, esters and amides are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity.Type: GrantFiled: February 26, 1979Date of Patent: February 3, 1981Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Haydn W. R. Williams, Otto W. Woltersdorf, Jr.
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Patent number: 4216172Abstract: A process for the preparation of a cyclobutanone of the formula ##STR1## in which R.sup.1 to R.sup.6 each independently is a hydrogen, halogen, cyano, alkoxy, alkoxycarbonyl, carboxamido, dialkylphosphono, alkyl, cycloalkyl, aryl, aralkyl or alkenyl radical, or two of them together with the carbon atom to which each is linked form a ring,comprising reacting an N,N-disubstituted carboxylic acid amide of the formula ##STR2## in which R.sup.7 and R.sup.8 each independently is an alkyl, cycloalkyl, alkenyl, aryl or aralkyl radical or together form a ring, with an inorganic acid halide, and then reacting the product with a tertiary amine, an olefin of the formula ##STR3## and a Lewis acid, and subsequently hydrolyzing the mass. Preferably isobutyric acid dimethylamide is employed as the carboxylic acid amide, phosgene is employed as the inorganic acid halide, triethylamine is employed as the tertiary amine and zinc chloride or titanium tetrachloride is employed as the Lewis acid.Type: GrantFiled: March 13, 1978Date of Patent: August 5, 1980Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Heine, Willy Hartmann
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Patent number: 4216218Abstract: Novel 4-aryloxy- and 4-arylthio-3-phenylpiperidines and related compounds, physiologically acceptable salts thereof and intermediates therefor possessing analgesic, antidepressant properties, and a process for the preparation of such compounds, derivatives and intermediates are described.Type: GrantFiled: February 23, 1979Date of Patent: August 5, 1980Assignee: American Hoechst CorporationInventors: Solomon S. Klioze, Frederick J. Ehrgott
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Patent number: 4091111Abstract: A novel substituted-arylacetic acid ester of the formula, ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen or a halogen atom, a C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.1 -C.sub.4 alkoxy, cyano, nitro, methylthio, C.sub.1 -C.sub.4 alkanoyl, C.sub.1 -C.sub.4 alkanoyloxy, or C.sub.1 -C.sub.4 alkoxycarbonyl group, or R.sub.1 and R.sub.2, taken together, may form methylenedioxy, a C.sub.3 -C.sub.5 alkylene or butadienylene (--CH.dbd.CH--CH.dbd.CH--) ring; R.sub.3 is a C.sub.2 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, propargyl, C.sub.3 -C.sub.6 cycloalkyl or cyclopropylmethyl group; R.sub.4 is hydrogen or a halogen atom, methyl or ethyl group; R.sub.5 is allyl, propargyl, 3-butenyl, 3-butynyl, phenyl or benzyl group; and A is oxygen or sulfur atom or --CH.dbd.CH-- group, which possesses various useful insecticidal and acaricidal activities and can be prepared by reacting a substituted-arylacetic acid of the formula; ##STR2## wherein R.sub.1, R.sub.2, R.sub.Type: GrantFiled: October 1, 1976Date of Patent: May 23, 1978Assignee: Sumitomo Chemical Company LimitedInventors: Nobuo Ohno, Isao Ohno, Toshio Nishioka, Hisami Takeda, Kiyoshi Kasamatsu
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Patent number: 4075240Abstract: Novel polymers formed from the reaction of tetracarboxylic dianhydrides and hydrazines or hydrazides which may be cross-linkable by further reaction with a hydrazine or a hydrazide are disclosed.Type: GrantFiled: November 4, 1975Date of Patent: February 21, 1978Assignee: PPG Industries, IncInventors: Karl F. Schimmel, Marco Wismer
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Patent number: 4069241Abstract: Tricyclic aromatic compounds of the formula ##STR1## including those wherein: A. R.sub.1 is H, R.sub.2 is carbomethoxy, and R.sub.3 is methyl;B. R.sub.1 is acetyl, R.sub.2 is carbomethoxy, and R.sub.3 is methyl;C. R.sub.1 and R.sub.3 are methyl and R.sub.2 is carbomethoxy;D. R.sub.1, R.sub.2, and R.sub.3 are hydrogen; andE. R.sub.1 and R.sub.3 are methyl and R.sub.2 is hydrogenAre intermediates for the total synthesis of steroids.Type: GrantFiled: May 26, 1976Date of Patent: January 17, 1978Assignee: The United States of America as represented by the Department of Health, Education and WelfareInventors: Ulrich Weiss, Kenner C. Rice
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Patent number: 4060528Abstract: Compounds of the class of aroyl-substituted phenylacetic acids and corresponding esters, amides and hydroxamic acids, useful as anti-inflammatory agents and certain novel precursors therefor.Type: GrantFiled: December 10, 1976Date of Patent: November 29, 1977Assignee: Janssen Pharmaceutica N.V.Inventors: Paul Adriaan Jan Janssen, Georges Henri Paul Van Daele, Jozef Martin Boey
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Patent number: 4046814Abstract: A method for preparing diketone starting materials useful in synthesizing tetraketone precursors for high temperature resistant polyquinoxaline resins. Dicarboxylic acid derivatives that contain no alpha hydrogens are contacted in the presence of a strong base with an active-hydrogen compound of the type R -- CH.sub.2 -- X where R is an aryl, substituted aryl, heterocyclic or substituted heterocyclic radical and X is a nitrile group or a carboxylic acid functional group. A reaction intermediate is formed having the formula: ##STR1## wherein R and X are as defined in regard to the active-hydrogen compound and R' is the same as R. The reaction intermediate is hydrolyzed and decarboxylated to form the diketone. The diketones produced by the instant invention have the formula: ##STR2## where R and R' are the same as in the reaction intermediate.Type: GrantFiled: December 18, 1975Date of Patent: September 6, 1977Assignee: Wright State UniversityInventors: Frank W. Harris, Bruce A. Reinhardt
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Patent number: RE33109Abstract: The present invention provides chalcone derivatives of the general formulae: ##STR1## wherein R.sub.1 is a hydroxyl, carboxylic or sulphonic acid group or a carboxyalkoxy or sulphoalkoxy radical, R.sub.2 is an unsaturated, straight-chained or branched aliphatic hydroxycarbonyloxy radical, R.sub.3 is a hydrogen atom, a hydroxyl group or an alkoxy radical, R.sub.4 is an alkyl, hydroxyalkyl, alkoxy, carboxyalkoxy, sulphoalkoxy or carboxyalkylcarbonyloxyalkyl radical or a carboxylic acid or sulphonic acid group and R.sub.5 is a hydrogen or halogen atom, with the proviso that compounds of general formula (IIa) always contain at least one carboxylic or sulphonic acid group; and the nontoxic inorganic and organic salts of those compounds containing at least one carboxylic acid or sulphonic acid group.The present invention also provides a process for the preparation of these chalcone derivatives, as well as pharmaceutical compositions containing them.Type: GrantFiled: April 8, 1988Date of Patent: November 7, 1989Assignee: Biorex Laboratories LimitedInventors: Anthony E. Vanstone, Graham K. Maile, Lynn K. Nalbantoglu