Alicyclic Acids Having An Element Other Than Oxygen, Carbon, Or Hydrogen Patents (Class 562/507)
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Patent number: 5047582Abstract: A process for oxidation of a tetrahydro compound of the formula ##STR1## wherein R and R' independently are H, alkyl, aryl or halo, to a glycol of the formula ##STR2## comprises treating the tetrahydro compound with hydrogen peroxide at an elevated temperature in the absence of a catalyst.The thus-formed glycol can be further oxidized in a butanetetracarboxylic acid of the formula ##STR3## with hydrogen peroxide in the presence of a catalyst selected from the group consisting of a manganese salt, an iron salt, a chromium salt, a cerium salt, a persulfate, a perborate, a silicate, tungstic acid or an ammonium or alkali metal salt or heteropolyacid thereof, or molybdic acid or an ammonium or alkali metal salt or heteropolyacid thereof.Type: GrantFiled: October 2, 1989Date of Patent: September 10, 1991Assignee: Ortec, Inc.Inventors: David L. Brotherton, Kwok W. Fung
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Patent number: 5030654Abstract: A series of novel spiro-substituted glutaramide derivatives have been prepared, including the pharmaceutically acceptable salts thereof and bioprecursors therefor, wherein the spiro-substituent completes a 5- or 6-membered carbocycyclic ring and is located at the carbon atom adjacent to the carbamoyl group. These particular compounds are inhibitors of the neutral endopeptidase E.C.3.4.24.11 enzyme and are therefore useful in therapy as diuretic agents for the treatment of hypertension, heart failure, renal insufficiency and other disorders. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: May 19, 1989Date of Patent: July 9, 1991Assignee: Pfizer Inc.Inventors: Ian T. Barnish, John C. Danilewicz, Keith James, Gillian M. R. Samuels, Nicholas K. Terrett, Michael T. Williams, Martin J. Wythes
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Patent number: 5026906Abstract: A new process of synthesis of optically active .alpha.-amino acids is described through nitrosation in a non-aqueous, aprotic system of the corresponding N-carbamyl derivatives followed by decomposition of the thus obtained N-nitroso derivatives in aqueous acidic medium. The process, which is of a general applicability, leads to a remarkable increase in the reaction yields, due to the suppression of the main side reaction leading to the corresponding .alpha.-hydroxy-acid. Some N-nitroso intermediates, which can be recovered from the process of the invention, are also described.Type: GrantFiled: February 28, 1990Date of Patent: June 25, 1991Assignee: Eniricerche S.p.A.Inventors: Sandro Di Gioacchino, Antonio Paolinelli, Luciano Re
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Patent number: 5025034Abstract: Prostaglandin analogues exhibiting activity at thromboxane receptor sites have been prepared.Type: GrantFiled: February 7, 1990Date of Patent: June 18, 1991Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 5025017Abstract: Seco-mevinic acid derivatives are provided which has the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R.sup.1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R.sup.2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR.sup.5 wherein R.sup.5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis. New intermediates for preparing the above seco-mevinic acid derivatives are also provided.Type: GrantFiled: September 28, 1989Date of Patent: June 18, 1991Assignee: E. R. Squibb & Sons, Inc.Inventor: Donald S. Karanewsky
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Patent number: 5017721Abstract: A new process for preparing oxalyl- and oxamyl-hydrazides which comprises contacting oxamide or diacetyloxamide with the corresponding hydrazine derivative of formulaR.sub.1 R.sub.2 N--NHR.sub.3wherein R.sub.1 represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl, aryl, or aryl-alkyl group, R.sub.2 is a hydrogen atom or an optionally substituted alkyl group, or R.sub.1 and R.sub.2 taken together with the adjacent nitrogen atom represent a saturated heterocyclic ring, and R.sub.3 is a hydrogen atom or an optionally substituted alkyl group.Type: GrantFiled: April 21, 1989Date of Patent: May 21, 1991Assignee: Enichim ANIC S.p.A.Inventors: Giuseppe Messina, Loreno Lorenzoni, Paolo Calaresu, Giovanni M. Sechi
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Patent number: 4990648Abstract: A process for production of an alkylthiobenzoate comprising reacting a cyclohexenone having the formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.6 alkyl; X is alkyl or unsubstituted alkyl; and Y is hydrogen, halogen or alkyl, with a mercaptan having the formula R.sub.2 SH in which R.sub.2 is C.sub.1 -C.sub.4 alkyl, preferably in the presence of an acid catalyst, to form a cyclohexadiene thioether, and dehydrogenating the thioether to produce a thioalkylbenzoate.The thioalkylbenzoate may be further converted by oxidation and/or hydrolysis to a corresponding thioalkyl, alkylsulfinyl or alkylsulfonyl benzoic acid.Type: GrantFiled: January 3, 1990Date of Patent: February 5, 1991Assignee: ICI Americas Inc.Inventor: Richard W. Brown
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Patent number: 4978759Abstract: The process described makes it possible to obtain optically pure 4-amino-3-hydroxycarboxylic acids by means of a series of stereoselective steps. The starting material is an alpha-amino acid in the L or D configuration, with which Meldrum's acid is reacted. The resulting pyrrolone derivative is reduced prior to opening of the pyrrolidine ring. The invention also relates to the new products obtained by the said process and to the pyrrolone derivatives obtained as intermediates.Type: GrantFiled: July 2, 1986Date of Patent: December 18, 1990Assignee: Sanofi, S.A. and Institut National de la Sante et de la Recherche MedicaleInventors: Patrick Jouin, Dino Nisato, Bertrand Castro
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Patent number: 4960931Abstract: A novel crystalline form of gabapentin and a novel processes for the small and large scale preparations of the anticonvulsant compound in a highly pure state is disclosed. This novel hydrate is produced by a cost effective process which provides an additional purification stage.Type: GrantFiled: October 6, 1989Date of Patent: October 2, 1990Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, Barbara J. Greenman
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Patent number: 4942254Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula. ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, NR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.Type: GrantFiled: January 29, 1988Date of Patent: July 17, 1990Assignee: Union Oil Company of CaliforniaInventor: Donald C. Young
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Patent number: 4936906Abstract: Agents for regulating plant growth containing an effective amount of at least one cyclohexanone derivative of the formula I ##STR1## where A, X, n, Y, Z and R have the meanings given in the disclosure, or salts of these compounds, and a process for regulating plant growth.Type: GrantFiled: July 2, 1986Date of Patent: June 26, 1990Assignee: BASF AktiengesellschaftInventors: Dieter Jahn, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Rainer Becker, Johann Jung, Wilhelm Rademacher
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Patent number: 4927964Abstract: An advantageous method of producing in large amounts on a commercial scale 2-substituted oxyimino-3-oxobutyric acids, which are useful as intermediates in the synthesis of e.g. aminothiazole cephalosporins, is characterized by reacting a tert-butyl 2-substituted oxyimino-3-oxobutyrate with a hydrogen halide in an anhydrous organic solvent.Type: GrantFiled: January 11, 1989Date of Patent: May 22, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Kenzo Naito, Yukio Ishibashi, Haruo Shinbo
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Patent number: 4925978Abstract: A new process of synthesis of optically active .alpha.-amino acids is described through nitrosation in a non-aqueous, aprotic system, of the corresponding N-carbamyl derivatives followed by decomposition of the thus obtained N-nitroso derivatives in aqueous acidic medium. The process, which is of a general applicability, leads to a remarkable increase in the reaction yields, due to the suppression of the main side reaction leading to the corresponding .alpha.-hydroxy-acid. Some N-nitroso intermediates, which can be recovered from the process of the invention, are also described.Type: GrantFiled: April 14, 1988Date of Patent: May 15, 1990Assignee: Eniricerche S.p.A.Inventors: Sandro Di Gioacchino, Antonio Paolinelli, Luciano Re
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Patent number: 4925970Abstract: A process for production of an alkylthiobenzoate comprising reacting a cyclohexenone having the formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.6 alkyl; X is alkyl or unsubstituted alkyl; and Y is hydrogen, halogen or alkyl, with a mercaptan having the formula R.sub.2 SH in which R.sub.2 is C.sub.1 -C.sub.4 alkyl, preferably in the presence of an acid catalyst, to form a cyclohexadiene thioether, and dehydrogenating the thioether to produce a thioalkylbenzoate.The thioalkylbenzoate may be further converted by oxidation and/or hydrolysis to a corresponding thioalkyl, alkylsulfinyl or alkylsulfonyl benzoic acid.Type: GrantFiled: December 22, 1988Date of Patent: May 15, 1990Inventor: Richard W. Brown
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Patent number: 4918223Abstract: N-acylated mercapto-.alpha.-amino acids of the general formula ##STR1## are prepared by reacting a nitrile of the general formulaR.sub.1 -CN (II)at a temperature between 0.degree. C. and 100.degree. C. in water or in a mixture of water and an organic solvent which is at least partially miscible with water, in the presence of a base with a mercapto-.alpha.-amino acid of the general formula ##STR2## and subsequently releasing the N-acylated mercapto-.alpha.-amino acid of general formula (I) with an acid. Mercapto-.alpha.-amino acids can be selectively acylated on the amino group in this manner in a relatively simple manner.Type: GrantFiled: August 9, 1988Date of Patent: April 17, 1990Assignee: Degussa AktiengesellschaftInventors: Hans-Peter Krimmer, Karlheinz Drauz
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Patent number: 4914232Abstract: An essentially single stage reaction has been discovered in which a disubstituted ethanolamine, that is, a 2,2'-substituted-2-aminoethanol, may be reacted with a haloform and a carbonyl containing compound selected from the group consisting of monoketones and benzaldehyde, in the presence of an alkali metal hydroxide, and optionally in the presence of a phase transfer catalyst, to produce an alkali metal hydroxyethylaminoacetate ("HEAA") which has N-adjacent C atoms on which there are a total of at least three substituents (hence "polysubstituted"), and one or both pairs of substituents on each N-adjacent C atom may be cyclized. The HEAA may be cyclized by the action of a mineral acid to produce a 2-morpholone hydrochloride which is characterized by having a total of at least three substituents on the N-adjacent C atoms of the ring. The 2-morpholone so produced may be reduced to a polysubstituted aminodiol.Type: GrantFiled: September 28, 1987Date of Patent: April 3, 1990Assignee: The B. F. Goodrich CompanyInventor: John Ta-Yuan Lai
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Patent number: 4908475Abstract: New compounds which have potent V.sub.2 -vasopressin antagonistic activity are prepared by a 1,6-cyclization using peptide bond formation. The structures of the compounds are characterized by a Pas.sup.1,6 or Tas.sup.1,6 cyclized unit. Also a chiral synthesis of the optically pure Pas intermediates is described.Type: GrantFiled: May 9, 1988Date of Patent: March 13, 1990Assignee: SmithKline Beckman CorporationInventors: James F. Callahan, William F. Huffman, Kenneth A. Newlander, Nelson C. F. Yim
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Patent number: 4906280Abstract: T-butylhydrazides of carboxylic acid anhydrides and carboxylic acid chlorides useful as plant growth regulants in the free acid form or their equivalent salts.Type: GrantFiled: October 14, 1987Date of Patent: March 6, 1990Assignee: Pennwalt CorporationInventors: Stanley R. Sandler, Shyam B. Advani
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Patent number: 4898930Abstract: Peptide ester and amide derivatives of the general formula I: ##STR1## in which X is H or an acyl, A and B are structurally defined amino acid residues, n is an integer of from 1 to 3, R.sup.1 is H or a lower alkyl and either R.sup.2 or C is a defined optionally modified amino acid residue and the other is a lower alkoxyl, an amino group or a direct chemical bond, are converted under physiologic conditions, by enzymic hydrolysis in pathologically altered tissues and subsequent spontaneous cyclization, into pharmacodynamically active spirocyclic peptide derivatives of the general formula III: ##STR2## in which R.sup.3 and R.sup.4 are H atoms, optionally substituted alkyl groups or jointly an aliphatic chain forming preferably a 2,5- piperazinedione ring, and hence can act as pro-farmaca (drug precursors) of prolonged biological effect.Type: GrantFiled: June 12, 1987Date of Patent: February 6, 1990Assignee: Spofa, spojene podniky proInventors: Evzen Kasafirek, Miroslav Rybak, Ivan Krejci, Antonin Sturc, Alena Roubalova, Jiri Vanzura, Evzen Krepela, Michal Bartik
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Patent number: 4898977Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonisation of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.Type: GrantFiled: August 13, 1987Date of Patent: February 6, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst
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Patent number: 4889656Abstract: Perfluoro(cycloaliphatic methyleneoxyalkylene) compositions are provided. These compositions comprise perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluoride compounds having (a) a perfluorocycloaliphatic moiety which can have up to two perfluoroalkyl substituents and a perfluoroalkylene substituent, and (b) a perfluoromethyleneoxyalkylene carbonyl fluoride radical, the methylene group of the radical being bonded to a ring carbon atom or the perfluoroalkylene substituent of the moiety and the alkylene group of the perfluoromethyleneoxyalkylene carbonyl fluoride being a perfluoro(methyl)methylene group, a perfluoroisopropyleneoxy(methyl)methylene group, or a poly(perfluoroisopropyleneoxy)perfluoro(methyl)methylene group having up to about 10 perfluoroisopropyleneoxy units.Type: GrantFiled: October 30, 1987Date of Patent: December 26, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventors: Richard M. Flynn, Patricia M. Savu
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Patent number: 4831184Abstract: This invention relates to new chemical compounds having valuable pharmaceutical activity. It particularly relates to stereoisomeric compounds possessing hypotensive activity, i.e., angiotensin converting enzyme inhibitory (ACEI) activity and having the structure ##STR1## wherein R and R.sub.9 are independently hydroxy, lower alkoxy, lower alkenoxy, di(lower alkyl)amino-lower alkoxy, hydroxy-lower alkoxy, acylamino-lower alkoxy, acryloxy-lower alkoxy, aryloxy, aryloxyl-lower alkoxy, amino, lower alkylamino, di-lower alkylamino, hydroxyamino, or aryl-lower alkylamino;R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.7 and R.sub.8 are independently hydrogen, alkyl, alkenyl or alkynyl containing up to 20 carbon atoms, aryl or aryl-lower alkyl having from 7 to 12 carbon atoms, heterocyclic or heterocyclic-lower alkyl having from 6 to 12 carbon atoms, cycloalkyl or cycloalkyl-alkyl containing up to 20 carbon atoms in the cycloalkyl group, provided that each of R.sub.1 and R.sub.2 and R.sub.4 and R.sub.Type: GrantFiled: February 14, 1983Date of Patent: May 16, 1989Assignee: Rorer Pharmaceutical CorporationInventors: Raymond D. Youssefyeh, Jerry W. Skiles, John T. Suh, Howard Jones
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Patent number: 4820729Abstract: Compounds of the formula ##STR1## wherein R and R.sub.9 are independently hydroxy or lower alkoxy,R.sub.1 and R.sub.2 are hydrogen or lower alkyl, aryl-lower alkyl having from 7 to 12 carbon atoms, or heterocyclic-lower alkyl having from 6 to 12 carbon atoms,R.sub.3, R.sub.4, R.sub.5, R.sub.7 and R.sub.8 are hygrogen or lower alkyl,R.sub.6 is cycloalkly having from 3 to 20 carbon atoms, aryl or aryl-lower alkyl, and the aryl group contains from 6 to 10 carbon atoms, and their pharmaceutically acceptable, nontoxic acid addition salts and where R or R.sub.9 or both are hydroxy, their pharmaceutically acceptable, nontoxic basic salts possess antihypertensive activity.Type: GrantFiled: March 30, 1981Date of Patent: April 11, 1989Assignee: Rorer Pharmaceutical CorporationInventors: Raymond D. Youssefyeh, Jerry W. Skiles, John T. Suh, Howard Jones
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Patent number: 4814485Abstract: The invention relates to new (4S)-4-aminobutanoic acid derivatives of general formula: ##STR1## in which: R represents an N-protective group,R.sub.1 represents hydrogen, an alkali metal atom such as lithium, sodium or potassium or a liabile group,R.sub.2 represents a group of formula: ##STR2## in which W represents hydrogen, a hydroxy group or an alkyl radical containing from 1 to 4 carbon atoms or an alkoxy radical containing from 1 to 4 carbon atoms, and to a process for the preparation of the said derivatives.The 4-aminobutanoic acid derivatives according to the invention are useful as synthesis intermediates for the preparation of peptides derived from statin analogues.Type: GrantFiled: December 2, 1986Date of Patent: March 21, 1989Assignee: SanofiInventors: Marcel Descamps, Dino Nisato, Walter Verstraeten
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Patent number: 4803268Abstract: The present invention relates to a novel, optimized process for the preparation of cyclohexanedionecarboxylic acid derivatives of formula I which can be carried out in a single vessel affording a very good yield, which process comprises heating a reactive carboxylic acid derivative of formula III ##STR1## wherein X is a halide, an alkylsulfonic or arylsulfonic acid radical or the molecular radical ##STR2## which is necessary to form an anhydride and R.sub.1 is alkyl or cycloalkyl, with an alkali metal cyanide or copper cyanide, in an inert organic solvent, to give a mixture, then adding in succession to said mixture, at a temperature in the range from 0.degree. C.Type: GrantFiled: January 29, 1987Date of Patent: February 7, 1989Assignee: Ciba-Geigy CorporationInventors: Hans-Georg Brunner, Urs Muller
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Patent number: 4794197Abstract: All-cis-1,3,5-Triamino-2,4,6-trihydroxycyclohexane derivatives corresponding to the general formula I ##STR1## wherein the symbols R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are identical or different and represent hydrogen atoms, alkyl groups or --CO-alkyl groups wherein the alkyl in the alkyl or --CO-alkyl group has 1 to 18 carbon atoms and the alkyl and --CO-alkyl groups may contain, independently of one another, one or more identical or different functional groups, and at least one of the groups R.sub.1 to R.sub.6 is one of the above mentioned unsubstituted or substituted alkyl groups or --CO-alkyl groups, and their salts with pharmacologically conventionally used inorganic or organic acids and their quaternary ammonium salts, processes for their preparation and their use, and pharmaceutical preparations containing these compounds.Type: GrantFiled: January 31, 1986Date of Patent: December 27, 1988Inventors: Walter Schneider, Isidor Erni, Hans K. Hegetschweiler
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Patent number: 4788332Abstract: Sweeteners of the formula: ##STR1## and food-acceptable salts thereof, where the substituents are disclosed herein.Type: GrantFiled: January 19, 1988Date of Patent: November 29, 1988Assignee: General Foods CorporationInventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
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Patent number: 4780129Abstract: Cyclohexenone derivatves of the formula ##STR1## where R.sup.1 is alkyl, R.sup.2 is alkyl, unsubstituted or substituted alkenyl or alkynyl, A is alkoxycarbonyl, carboxyl, cyano or trifluoromethyl, B is hydrogen or methyl, X is straight-chain, branched or cyclic alkylene, Z is hydrogen or alkoxycarbonyl and n is 0 or 1, and salts thereof, and their use for combatting unwanted plant growth.Type: GrantFiled: February 13, 1987Date of Patent: October 25, 1988Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Dieter Jahn, Ulrich Schirmer, Michael Keil, Bruno Wuerzer, Norbert Meyer
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Patent number: 4764366Abstract: Novel lower alkyl esters of iodo-trans-2-methylcyclohexanecarboxylic acid are useful to attract the Mediterranean Fruit Fly, "Medfly," for prolonged periods of time. The esters are competitive in attraction with the current "standard" attractant, Trimedlure, but are much more persistent. The esters may be economically produced and possess the dual properties required for effective use in Medfly control programs.Type: GrantFiled: April 27, 1987Date of Patent: August 16, 1988Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Terrence P. McGovern, Roy T. Cunningham
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Patent number: 4762548Abstract: Herbicidally active thiolcarbamates are employed in combination with a certain amide extender compound, the latter in sufficient quantity to minimize soil degradation and to prolong the soil life of the former. As a result, the herbicidal effectiveness of the thiolcarbamate herbicide is significantly enhanced and prolonged, rendering a single application or multiple applications of the herbicide effective over a longer period of time. Such herbicidal compositions can optionally contain a non-phytotoxic antidotally effective amount of thiolcarbamate herbicide antidote.Type: GrantFiled: August 12, 1985Date of Patent: August 9, 1988Assignee: Stauffer Chemical Co.Inventors: Reed A. Gray, Ferenc M. Pallos
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Patent number: 4760175Abstract: This invention relates to novel sweeteners of the formula: ##STR1## wherein A is hydroxyalkyl containing 1-3 carbon atomsA' is hydrogen or alkyl containing 1-3 carbon atoms;Y is --(CHR.sub.2).sub.n --R.sub.1 or --CHR.sub.3 R.sub.4 ;R.sub.1 is cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl containing up to 7 ring carbon atoms and up to a total of 12 carbon atoms;R.sub.2 is H or alkyl containing 1-4 carbon atoms;R.sub.3 and R.sub.4 are each cycloalkyl containing 3-4 ring carbon atoms;n=0 or 1; andm=0 or 1;and food-acceptable salts thereof.Type: GrantFiled: May 6, 1985Date of Patent: July 26, 1988Assignee: General Foods CorporationInventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
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Patent number: 4748160Abstract: There are described compounds of formula I,ZCHRCON(--N.dbd.CR.sub.4 R.sub.5)CHR.sub.6 (CH.sub.2).sub.n COY Iwhere the substituents are defined in the disclosure.There are also described methods for making the compounds, formulations containing them and their use, e.g. as antihypertensives.Type: GrantFiled: November 14, 1985Date of Patent: May 31, 1988Assignee: Fisons plcInventors: Colin Bennion, David P. Marriott, Anthony R. Cook, David H. Robinson
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Patent number: 4748274Abstract: The present invention relates to compounds which are 4-hydroxy-4-alkenylcyclohexanecarboxylic acid derivatives possessing leukotriene antagonist activity. The compounds are useful in the treatment of allergic diseases, particularly in the treatment of human asthma. They are prepared by the reaction of an appropriate oxaspiro compound with a mercaptoalkanoic acid derivative.Type: GrantFiled: November 7, 1986Date of Patent: May 31, 1988Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Robert J. Cregge, Nelsen L. Lentz
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Patent number: 4736055Abstract: Oxime sulfonates of formula I ##STR1## wherein Y is a polymerizable unsaturated group or epoxide group or an --OH, --NHR.sup.5, --COOH, COOR.sup.6, --COCl, --CH.sub.2 Hal, --SO.sub.2 Cl or --NCO group, Z is an (x+y)-valent connecting member, R.sup.1 and R.sup.2 are monovalent organic radicals, m is 0 or 1, x is 1 or 2 and y is 1 or 2, can be converted into polymers which can be thermally or photochemically dissociated to form free sulfonic acid groups. Said polymers can therefore be used as photoresists which can be developed with aqueous alkalis.Type: GrantFiled: April 11, 1986Date of Patent: April 5, 1988Assignee: Ciba-Geigy CorporationInventors: Kurt Dietliker, Werner Rutsch, Godwin Berner, Max Hunziker, Christopher G. Demmer
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Patent number: 4736043Abstract: The present invention provides a process for the preparation of 4-hydroxyindole derivatives of the general formula: ##STR1## in which R.sub.1 is a hydrogen atom or an alkyl radical containing up to 6 carbon atoms and R.sub.2 is a hydrogen atom or an alkyl radical containing up to 6 carbon atoms, wherein a compound of the general formula: ##STR2## in which R.sub.2 has the same meaning as above, is reacted with a compound of the general formula:R.sub.3 --CH.sub.2 --CO--COOR.sub.1 (III)in which R.sub.1 has the same meaning as above and R.sub.3 is a reactive residue, to give a 2-(2-imino-6-oxocyclohexylidene)-propionic acid derivative of the general formula: ##STR3## in which R.sub.1, R.sub.2 and R.sub.3 have the same meanings as above, which is then cyclized in known manner to give a compound of the general formula: ##STR4## in which R.sub.1 and R.sub.2 have the same meaning as above, which is subsequently dehydrated.Type: GrantFiled: November 2, 1982Date of Patent: April 5, 1988Assignee: Boehringer Manneheim GmbHInventors: Helmut Michel, Roland Ofenloch
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Patent number: 4733003Abstract: Compounds of formula (I): ##STR1## [wherein X represents a hydrogen atom or a 2-methylbutyryl group, Y represents a hydrogen atom or a methyl group and R.sup.1 and R.sup.2 are the same or different and each represents an oxygen atom or a group of formula .dbd.N--OR.sup.3 (wherein R.sup.3 represents a hydrogen atom or an alkyl group)], the free hydroxy-carboxylic acids corresponding thereto and salts and esters of said acids may be prepared by oxidizing and, if necessary, oximating a corresponding ML-236A, ML-236B, MB-530A or MB-530B compound, and these compounds have valuable antihypercholesteraemic activity.Type: GrantFiled: May 6, 1986Date of Patent: March 22, 1988Assignee: Sankyo Company LimitedInventors: Junya Ide, Shigeki Muramatsu, Yoshio Tsujita, Msao Kuroda
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Patent number: 4709056Abstract: 4,4-dihalohexahydrophthalic anhydrides of the formula ##STR1## where Y is chlorine or fluorine, are prepared by the reaction of hydrogen fluoride with 4-chlorotetrahydrophthalic anhydride.The 4,4-dihalohexahydrophthalic anhydrides of this invention can be dehydrohalogenated by reaction with basic alumina to prepare a mixture of 4-fluorotetrahydrophthalic anhydride isomers of the formula ##STR2## The 4-fluorotetrahydrophthalic anhydrides can then be dehydrogenated by reaction with a dehydrogenation catalyst to prepare 4-fluorophthalic anhydride.Type: GrantFiled: May 2, 1984Date of Patent: November 24, 1987Assignee: Occidental Chemical CorporationInventors: Byron R. Cotter, Henry C. Lin, Joseph A. Pawlak
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Patent number: 4708954Abstract: Pharmaceutical compositions containing an oxaluric acid derivative of the formula: ##STR1## wherein each of R.sub.1 and R.sub.2, which may be the same or different, is hydrogen; an alkyl group or a cycloalkyl group; or R.sub.1 and R.sub.2 are joined to form a heterocyclic ring with the nitrogen atom to which they are both attached; and R.sub.3 is hydrogen or an alkyl group. These compounds have excellent hypoglycemic effects with low toxcicity and safety.Type: GrantFiled: February 7, 1986Date of Patent: November 24, 1987Assignee: Nippon Zoki Pharmaceutical Co., Ltd.Inventors: Kazuharu Ienaga, Ko Nakamura, Akira Ishii
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Patent number: 4703037Abstract: Compounds of the formula ##STR1## and their pharmaceutically acceptable salts, wherein the substituents are as defined herein, having antihypertensive activity.Type: GrantFiled: February 18, 1986Date of Patent: October 27, 1987Assignee: Rorer Pharmaceutical CorporationInventors: Fu-chih Huang, John T. Suh, Jerry W. Skiles
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Patent number: 4701552Abstract: This invention relates to novel sweeteners of the formula: ##STR1## wherein A is hydrogen, alkyl containing 1-3 carbon atoms, hydroxyalkyl containing 1-3 carbon atoms, alkoxymethyl wherein the alkoxy contains 1-3 carbon atoms or --CO.sub.2 R in which R is alkyl containing 1-3 carbon atoms;A' is hydrogen or alkyl containing 1-3 carbon atoms;A and A' taken together with the carbon atom to which they are attached form cycloalkyl containing 3-4 carbon atoms;Y is --(CHR.sub.2).sub.n -R.sub.1 or --CHR.sub.3 R.sub.4 ;R.sub.1 is alkyl-substituted cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl containing at least one alkyl in the .beta.-position of the ring, up to 7 ring carbon atoms and up to a total of 12 carbon atoms;R.sub.2 is H or alkyl containing 1-4 carbon atoms;R.sub.3 and R.sub.4 are each cycloalkyl containing 3-4 ring carbon atoms;n=0 or 1; andm=0 or 1;and food-acceptable salts thereof.Type: GrantFiled: March 21, 1986Date of Patent: October 20, 1987Assignee: General Foods CorporationInventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
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Patent number: 4698442Abstract: .alpha.-amino acids having a substituted .omega.-guanidino group are disclosed herein.Type: GrantFiled: June 13, 1986Date of Patent: October 6, 1987Assignee: Syntex (U.S.A.) Inc.Inventors: John J. Nestor, Brian H. Vickery
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Patent number: 4694103Abstract: A novel, one-pot procedure for the preparation of N-acryloyl-.alpha.-amino acids involves the steps of:(i) reacting a ketone, an ammonium salt, and a cyanide salt in water, optionally in the presence of ammonium hydroxide and a co-solvent, to form an aminonitrile;(ii) acryloylating the aminonitrile in aqueous media to afford an acrylamidonitrile; and(iii) hydrolyzing with aqueous acid the acrylamidonitrile to provide the N-acryloyl-.alpha.-amino acid.Type: GrantFiled: May 19, 1986Date of Patent: September 15, 1987Assignee: Minnesota Mining and Manufacturing CompanyInventors: Larry R. Krepski, Howell K. Smith, II, Jerald K. Rasmussen, Steven M. Heilmann
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Patent number: 4693745Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,R is C.sub.3 -C.sub.6 cycloalkyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.6 aralkyl, wherein the phenyl nucleus is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro or cyano; one of R.sub.3 and R.sub.4 is methoxy; orR.sub.3 and R.sub.Type: GrantFiled: October 9, 1985Date of Patent: September 15, 1987Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4678496Abstract: As new compound is provided a cyclohexane derivative of the formula ##STR1## wherein R represents a hydrogen atom or an alkyl group, an alkylthioalkyl group or an unsubstituted or substituted phenyl group; and R.sup.1 represents an alkyl group, an unsubstituted or substituted benzyl group, a phenethyl group, a phenoxymethyl group, a 2-thienylmethyl group, an alkoxymethyl group or an alkylthiomethyl group, or a salt of said cyclohexane compound.This cyclohexane compound exhibits useful plant-growth regulating effects on crop-plants and also non-crop plants such as lawn and may be prepared by cyclization of an acetonylsuccinic acid dialkyl ester, followed by reaction with an organic acid chloride and by intermolecular rearrangement.Type: GrantFiled: August 1, 1985Date of Patent: July 7, 1987Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
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Patent number: 4665225Abstract: A C.sub.21 amino acid is disclosed as a useful reactant for preparing polyamide resins.Type: GrantFiled: September 12, 1985Date of Patent: May 12, 1987Assignee: Union Camp CorporationInventor: Charles R. Frihart
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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: 4622422Abstract: The present invention is directed to 2-hydroxy-4-alkylidenecyclohexanealkanoic acids having a mercaptoalkanoic acid substituent at the 3-position. Esters and amides corresponding to the acids referred to above are also encompassed by the present invention. These compounds are useful in the treatment of bronchial asthma and they are obtained by the reaction of an appropriate 2,3-epoxy-4-alkylidenecyclohexanealkanoate with a mercapto alkanoic acid ester in the presence of a tertiary amine. The indicated process gives the esters of the present invention which can be hydrolyzed to the corresponding free acids by standard procedures. The compounds described can be subjected to other known reactions to give the other compounds of the present invention.Type: GrantFiled: August 23, 1985Date of Patent: November 11, 1986Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Robert J. Cregge, Jeffrey S. Sabol
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Patent number: 4619944Abstract: Provided are antihypertensive compounds of the formula ##STR1## wherein 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, or cycloalkyl, and may be the same or different,m is an integer from 0 to 2 inclusive,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-cycloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl.Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is alkyl, aryl, aralkyl, cycloalkyl, cycloalkyl-alkyl, heterocyclic, --CO--SR, --CS--SR, ##STR2## CH.sub.2 CO.sub.2 R, --CHM--CO.sub.2 R, --CH.sub.2 --CO--SR, --CN, ##STR3## --CO--NH--CH.sub.2 CO.sub.2 R, ##STR4## or --CO--CO.sub.Type: GrantFiled: February 19, 1985Date of Patent: October 28, 1986Assignee: USV Pharmaceutical CorporationInventors: Raymond D. Youssefyeh, Howard Jones
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Patent number: 4618360Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,B is hydroxyl, an --NHOR.sub.1 radical or a metal or ammonium salt thereofR is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkoxy or C.sub.2 -C.sub.4 alkythio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 alkynyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.Type: GrantFiled: November 19, 1984Date of Patent: October 21, 1986Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: RE32952Abstract: A novel, one-pot procedure for the preparation of N-acryloyl-.alpha.-amino acids involves the steps of:(i) reacting a ketone, an ammonium salt, and a cyanide salt in water, optionally in the presence of ammonium hydroxide and a co-solvent, to form an aminonitrile;(ii) acryloylating the aminonitrile in aqueous media to afford an acrylamidonitrile; and(iii) hydrolyzing with aqueous acid the acrylamidonitrile to provide the N-acryloyl-.alpha.-amino acid.Type: GrantFiled: December 30, 1987Date of Patent: June 13, 1989Assignee: Minnesota Mining and Manufacturing CompanyInventors: Larry R. Krepski, Howell K. Smith, II, Jerald K. Rasmussen, Steven M. Heilmann