Alicyclic Acids Having An Element Other Than Oxygen, Carbon, Or Hydrogen Patents (Class 562/507)
  • Patent number: 4613691
    Abstract: Amino acids can be easily prepared by reducing unsaturated hydantoins to the corresponding saturated hydantoins by hydrogenating the unsaturated hydantoin using either Raney Nickel catalyst in the presence of more than a stoichiometric amount of caustic or by using zinc and hydrochloric acid followed by hydrolyzing the resultant composition with at least 3 molar equivalents of an alkali metal hydroxide to produce a racemate of an alpha amino acid. The amino acid in suitable derivative form can then be resolved particularly using a two-phase solvent system. The residual isomer of the amino acid remaining after the resolution process can then be racemized using either pyridoxal-5-phosphate or an aliphatic acid in combination with an aldehyde or a ketone. By these procedures, it is possible to obtain high yields of amino acids.
    Type: Grant
    Filed: July 8, 1985
    Date of Patent: September 23, 1986
    Assignee: Stauffer Chemical Company
    Inventors: Stanley B. Mirviss, Mark W. Empie
  • Patent number: 4613676
    Abstract: Compounds of the formula ##STR1## in which R.sub.1 represents hydrogen or acyl, X.sub.1 represents an optionally N-alkylated amino acid residue that is bonded N-terminally to R.sub.1 and C-terminally to X.sub.2, X.sub.2 represents an optionally N-alkylated amino acid residue that is bonded N-terminally to X.sub.1 and C-terminally to the group --NR.sub.2 --, R.sub.2 represents hydrogen or lower alkyl, R.sub.3 represents hydrogen, alkyl, cycloalkyl, aryl- lower alkyl or aryl, R.sub.4 represents hydroxy or etherified or esterified hydroxy, R.sub.5 represents alkyl, cycloalkyl, aryl-lower alkyl or aryl, and R.sub.6 represents free or substituted amino or substituted hydroxy, and salts of such compounds having salt-forming groups inhibit the blood pressure-increasing action of the enzyme renin and can be used as anti-hypertensives.
    Type: Grant
    Filed: November 14, 1984
    Date of Patent: September 23, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Fuhrer, Peter Buhlmayer, Vittorio Rasetti, Bernhard Riniker
  • Patent number: 4609673
    Abstract: The present invention provides carboxylic acid derivatives of the general formula: ##STR1## wherein R is a hydrogen atom, alkyl, a metal cation or an ammonium or alkylammonium ion, R.sub.1 is a hydrogen atom, a hydroxyl group or an alkyl, O-alkyl,O-benzyl or O-acyl radical, R.sub.2 is a hydrogen atom or an alkyl, aryl or aralkyl radical, n is 0, 1 or 2 and R.sub.
    Type: Grant
    Filed: December 18, 1984
    Date of Patent: September 2, 1986
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hermann Eggerer, Bernd Hagenbruch, Tran G. Nguyen, Karlheinz Stegmeier, Johannes Pill
  • Patent number: 4594188
    Abstract: An enkephalin-degrading aminopentidase enzyme is inhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salt thereof, wherein R.sub.1 and R.sub.2 are each independently hydrogen, alkyl, carboxyalkyl, halo substituted alkyl, hydroxyalkyl, aminoalkyl, mercaptoalkyl, alkylthioalkyl, (cycloalkyl)alkyl, (heteroaryl)alkyl, arylalkyl, carbamoylalkyl, guanidinylalkyl, or heteroaryl;R.sub.3 is hydroxy, alkoxy, (substituted alkyl)oxy, arylalkoxy, (heteroaryl)alkoxy or --NY.sub.1 Y.sub.2, wherein Y.sub.1 and Y.sub.2 are each independently hydrogen, alkyl, aryl, or arylalkyl or Y.sub.1 is hydrogen and Y.sub.2 is substituted alkyl or (heteroaryl)alkyl;A.sub.1 is glycyl, alanyl, leucyl, phenylalanyl, arginyl, sarcosyl, seryl, asparagyl, lysyl, glutamyl, histidyl, tryptophyl, cysteinyl, methionyl, threonyl, tyrosyl, leucyl, valyl, aspartyl, prolyl, norleucyl, norvalyl, or ##STR2## wherein n.sub.6 is an integer of 2 to 15; A.sub.2, A.sub.3, A.sub.4 and A.sub.
    Type: Grant
    Filed: May 20, 1985
    Date of Patent: June 10, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Norma G. Delaney, Eric M. Gordon
  • Patent number: 4584013
    Abstract: 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 alkylthio,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: Grant
    Filed: May 14, 1984
    Date of Patent: April 22, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: 4584014
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, alkyl, cycloalkyl, phenylalkyl, alkoxyalkyl, alkoxyaryl, aryl or an agronomically acceptable cation; R.sup.2 and R.sup.3 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted phenylalkyl, carboxy, alkoxycarbonyl or phenyl group; X is hydrogen, fluoro, bromo, chloro or iodo atom; Y is a hydrogen, fluoro, bromo, chloro, iodo, alkyl, cycloalkyl, carboxy, alkoxycarbonyl, phenylalkyl, alkenyl and alkynyl group, wherein the alkyl, cycloalkyl, phenylalkyl and phenyl group may have up to three optional substituents; and B is hydrogen, carboxy, alkoxycarbonyl, methylene (--CH.sub.2 R.sup.4) or CZZ.sup.1 Z.sup.2 group wherein R.sup.4 is an alkyl or alkenyl group and Z, Z.sup.1 and Z.sup.2 are each independently a hydrogen, fluoro, bromo, chloro or iodo atom, provided that Z, Z.sup.1, Z.sup.2, X and Y are not all hydrogens.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: April 22, 1986
    Assignee: Rohm and Haas Company
    Inventor: Dennis R. Patterson
  • Patent number: 4571345
    Abstract: Compounds of the formula: ##STR1## wherein n is 0 or 1, R is lower alkyl (substituted or unsubstituted), R' is H or lower alkyl, and R" is a branched alkyl, alkyl-cycloalkyl, cycloalkyl, polycycloalkyl (poly=2 or more, fused or non-fused), phenyl or alkyl-substituted phenyl, and physiologically acceptable cationic and acid addition salts thereof, which compounds are potent sweeteners. These derivatives of gem-diaminoalkanes are many times sweeter than sugar and are free from undesirable flavor qualities. Furthermore, they possess an unanticipated high degree of solubility compared with known synthetic sweeteners. In addition, the compounds possess high stability so that they can be used in all types of beverages and in conventional food processing. Sweetening compositions and sweetened edible compositions of these compounds are also provided.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: February 18, 1986
    Assignee: Cumberland Packing Corp.
    Inventors: Michael S. Verlander, William D. Fuller, Murray Goodman
  • Patent number: 4570014
    Abstract: Novel plant growth regulant composition comprising as an active ingredient at least one cycloalkanecarboxylic acid compound of the formula ##STR1## in which R is hydroxyl, alkoxy, aralkoxy, amino, alkylamino, dialkylamino or the radicalO.sup..crclbar. M.sup..sym.whereinM.sup..sym. is one alkali metal ion equivalent or alkaline earth metal ion equivalent, or an ammonium, alkylammonium, dialkylammonium, trialkylammonium or tetraalkylammonium ion,R.sup.1 is amino or the radical ##STR2## wherein R.sup.2 is hydrogen, alkyl or aryl, orR.sup.1 is the radical --N.sup..sym. H.sub.3 X.sup..crclbar.,wherein X.sup.63 is chloride, bromide or iodide, and n is 1, 2, 3, 4 or 5,in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.
    Type: Grant
    Filed: December 15, 1981
    Date of Patent: February 11, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Schroder, Klaus Lurssen
  • Patent number: 4560403
    Abstract: 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: Grant
    Filed: September 22, 1983
    Date of Patent: December 24, 1985
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
  • Patent number: 4552569
    Abstract: Amide carboxylate salts of certain diamines are provided. These compounds give excellent results when tested in lubricants as, among other things, friction reducing additives.
    Type: Grant
    Filed: January 22, 1985
    Date of Patent: November 12, 1985
    Assignee: Mobil Oil Corporation
    Inventor: Andrew G. Horodysky
  • Patent number: 4546198
    Abstract: Stereoisomerically-enriched esters are prepared by treating a non-symmetrical ketene with a racemic or chiral tertiary-base-substituted alkylcarbinol. Optional hydrolysis of the esters gives the corresponding optically-active carboxylic acids corresponding to the non-symmetrical ketene.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: October 8, 1985
    Assignee: Shell Oil Company
    Inventor: Donald W. Stoutamire
  • Patent number: 4537964
    Abstract: Trans-(.+-.)-1-permissibly-substituted-2,6-dioxodecahydroquinoline or enantiomers thereof, intermediates for preparing tautomeric trans-(.+-.)-5-permissibly substituted octahydro-1H(and 2H)pyrazolo[3,4-g]quinolines, 4aR,8aR or 4aS,8aS enantiomers thereof, for preparing trans-(.+-.)-5-permissibly substituted-octahydropyrazolo (or oxazolo)[4,5-g]quinoline, 4aR,8aR or 4aS,8aS enantiomers thereof or for preparing trans-(.+-.)-6-permissibly-substituted octahydropyrimido[4,5-g]quinolines, a 5aR,9aR or 5aS,9aS enantiomer thereof said racemic intermediates being comprised of stereoisomers of the following formulas ##STR1## wherein R is H, alkyl or C.sub.1-3 straight-chain alkyl.
    Type: Grant
    Filed: August 3, 1984
    Date of Patent: August 27, 1985
    Assignee: Eli Lilly and Company
    Inventor: John M. Schaus
  • Patent number: 4535167
    Abstract: Chiral N-protected, N-substituted .alpha.-amino acids are described. These compounds are prepared by condensation of an N-protected .alpha.-amino acid with an aldehyde followed by the selective reductive cleavage of an oxazolidinone intermediate.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: August 13, 1985
    Assignee: Merck & Co. Inc.
    Inventor: Roger M. Freidinger
  • Patent number: 4529721
    Abstract: A compound of the formula: ##STR1## wherein u represents hydrogen, carboxamido, N-hydroxycarboxamido, carboxy, azido, an aryl, an acylamino, a protected carboxy or an N-alkoxycarboxamido, or, together with v, can represent --S-- or --CH.sub.2 S--; v represents hydrogen, halogen, cyano or an alkylthio, or, together with u, can represent --S-- or --CH.sub.2 S--, or, together with w, can represent --(CH.sub.2).sub.3 CO--; w represents hydrogen, carboamoyl, cyano, carboxy, an N-alkylcarbamoyl, an alkyl, an aryl, a protected carboxy or a heterocycle, or, together with v, can represents --(CH.sub.2).sub.
    Type: Grant
    Filed: September 21, 1983
    Date of Patent: July 16, 1985
    Assignee: Shionogi & Co., Ltd.
    Inventors: Wataru Nagata, Mitsuru Yoshioka, Yasuhiro Nishitani, Tsutomu Aoki, Toshiro Konoike, Tadatoshi Kubota
  • Patent number: 4528397
    Abstract: An aminocarboxylic acid derivative represented by the formula ##STR1## wherein R.sub.1 and R.sub.2, independently from each other, represent a hydrogen atom or an alkyl group which may have a substituent, and Y represents --NH-- or --S--, provided that when Y represents --NH--, at least one of R.sub.1 and R.sub.2 represents an alkyl group which may have a substituent. These compounds have excellent inhibitory activity on dipeptidase in animals, and are useful for administration in combination with carbapenem antibiotics.
    Type: Grant
    Filed: March 29, 1983
    Date of Patent: July 9, 1985
    Assignee: Sanraku-Ocean Co., Ltd.
    Inventors: Norio Shibamoto, Takeo Yoshioka, Yasuo Fukagawa, Tomoyuki Ishikura
  • Patent number: 4525294
    Abstract: The present invention relates to the preparation of mixtures of sterically hindered substituted N-secondary amino acids or their alkali metal salts by a one-step reductive condensation of an amino acid or its alkali metal salt containing a primary amino group and a ketone to thereby form a mono-substituted amino acid or alkali metal salt thereof, followed by preparing the corresponding sterically hindered tertiary amino acids or alkali metal salt thereof by reacting the mono-substituted amino acids or alkali metal salt thereof with an unhindered aldehyde under reducing conditions in the presence of a hydrogenating catalyst. The novel mixtures of the sterically hindered mono-substituted amino acids and the tertiary amino acids and their alkali metal salts are useful promoters for alkaline salts in "hot pot" acid gas scrubbing processes.
    Type: Grant
    Filed: April 14, 1983
    Date of Patent: June 25, 1985
    Assignee: Exxon Research and Engineering Co.
    Inventors: Guido Sartori, Warren A. Thaler
  • Patent number: 4525305
    Abstract: Fluorochemical aliphatic carboxylic acids, and water dispersible salts thereof, having fluoroaliphatic radicals and urylene and/or carbamato radicals, are used to impart oil and water repellency to fibrous substrates such as tanned leather.
    Type: Grant
    Filed: October 25, 1982
    Date of Patent: June 25, 1985
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Kalyanji U. Patel
  • Patent number: 4515982
    Abstract: Organic materials which contain from 0.001 to 10% by weight of an aminoreductone I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are H, methyl or ethyl and R.sup.4 is the radical of a naturally occurring .alpha.- or .beta.-aminoacid or of a C.sub.1 -C.sub.10 -alkyl ester thereof or, in the case of an .alpha.-aminoacid, a lactone having a 2--OH group in the cyclohexenone ring, or R.sup.4 is C.sub.1 -C.sub.20 -alkyl which is unsubstituted or substituted by --OH, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -acyloxy, or is --(CH.sub.2 --CH.sub.2 --O).sub.n H, which may be etherified with a C.sub.1 -C.sub.4 -alkanol or esterified with a C.sub.1 -C.sub.4 -fatty acid, and where n is from 2 to 10, or a mineral salt thereof.Novel compounds Ia differ from I in having the radical R.sup.4a, where R.sup.4a is R.sup.4 with the exception of methyl. Compounds I are prepared by reacting the corresponding 2,3-dihydroxycyclohex-2-en-1-one with an amine HN(R.sup.3)R.sup.4 or a mineral acid salt thereof.
    Type: Grant
    Filed: December 15, 1982
    Date of Patent: May 7, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Lechtken, Gerhard Mueller, Klaus Schmieder
  • Patent number: 4511482
    Abstract: Amide carboxylate salts of certain diamines are provided. These compounds give excellent results when tested in lubricants as, among other things, friction reducing additives.
    Type: Grant
    Filed: June 29, 1983
    Date of Patent: April 16, 1985
    Assignee: Mobil Oil Corporation
    Inventor: Andrew G. Horodysky
  • Patent number: 4504671
    Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: March 12, 1985
    Assignee: PPG Industries, Inc.
    Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
  • Patent number: 4459423
    Abstract: A process for producing efficiently and economically without using strong acids nor strong bases, .alpha.-amino acids from .alpha.-amino acid amides by hydrolyzing .alpha.-amino acid amides in an aqueous medium in the presence of ammonia. If necessary, the resultant hydrolyzate liquid from which .alpha.-amino acid has been removed may be reused.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: July 10, 1984
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masaharu Doya, Takako Uchiyama
  • Patent number: 4455263
    Abstract: Mono- and di-2-hydroxyethane sulfonate derivatives and 2-aminoethane sulfonate derivatives of C.sub.21 -cycloaliphatic dicarboxylic acid having the general formula ##STR1## where x and y are integers from 3 to 9, x and y together equal 12, R is ##STR2## and M.sup.+ is an alkali metal, ammonium or amine cation, are disclosed as emulsion polymerization emulsifiers.
    Type: Grant
    Filed: March 15, 1983
    Date of Patent: June 19, 1984
    Assignee: Westvaco Corporation
    Inventor: John W. Noble
  • Patent number: 4436910
    Abstract: Aqueous solutions of sodium salts of .alpha.-aminocarboxylic acids practically free of foreign salts are produced by saponifying the corresponding hydantoin at a temperature between 110.degree. C. and 180.degree. C. with a mixture, in each case based on the hydantoin, of 1 equivalent of sodium hydroxide and 2 equivalents of calcium oxide or hydroxide, separating off the precipitated calcium carbonate after the end of the saponification and concentrating the aqueous sodium salt solution remaining to drive off the ammonia contained therein.
    Type: Grant
    Filed: February 10, 1982
    Date of Patent: March 13, 1984
    Assignee: Degussa Aktiengesellschaft
    Inventors: Axel Kleemann, Bernd Lehmann, Jurgen Martens
  • Patent number: 4432907
    Abstract: Species-linked diamine triacetic acids of the formula ##STR1## wherein T is an organic species containing at least one amine, hydroxyl, or thio functional group, L is the residue of at least one of those functional groups and R is a two or more atom long covalent bridge, are disclosed. Methods for their preparation, for the preparation of metal chelates from them and for the use of the chelates are also disclosed. In a preferred embodiment, the metal ions employed in the formation of the chelates are rare earth metal ions capable of forming fluorescent chelates which can in turn be employed in fluoroassay techniques.
    Type: Grant
    Filed: May 5, 1981
    Date of Patent: February 21, 1984
    Assignee: Analytical Radiation Corporation
    Inventors: Irwin Wieder, Robert H. Wollenberg
  • 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: 4423029
    Abstract: (S)-3-amino-4-[(S,S)-1-(1-hydroxyethyl)alkylamino]-4-oxo-butyric acid compounds are non-nutritive sweeteners having favorable chemical and physiological properties.
    Type: Grant
    Filed: June 25, 1981
    Date of Patent: December 27, 1983
    Assignee: The Procter & Gamble Company
    Inventor: George P. Rizzi
  • Patent number: 4388312
    Abstract: New quinone derivatives of the formula: ##STR1## wherein R.sup.1 is methyl or methoxy, or two of R.sup.1 combine to represent --CH.dbd.CH--CH.dbd.CH--, R is amino which may be substituted or --OR.sup.4 wherein R.sup.4 is hydrogen, C.sub.1-4 alkyl or --CH.sub.2 --CH.dbd.C(CH.sub.3 --CH.sub.2 --.sub.m H (wherein m is an integer of 1 to 10), and n is an integer of 1 to 10 when R is amino which may be substituted, or n is an integer of 2 to 10 when R is --OR.sup.4, and their hydroquinone forms, have useful physiological activities such as blood-pressure decreasing and antiallergic activities.
    Type: Grant
    Filed: August 26, 1980
    Date of Patent: June 14, 1983
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Mitsuru Shiraishi, Kaneyoshi Kato
  • Patent number: 4386103
    Abstract: Dichloroamino acid derivatives other than .alpha.-dichloroamino acids are prepared from chlorination of corresponding amino acids, and are found to be potent germicidal and fungicidal agents.
    Type: Grant
    Filed: January 30, 1981
    Date of Patent: May 31, 1983
    Assignee: Merck & Co., Inc.
    Inventors: Stefano A. Pogany, Takeru Higuchi
  • Patent number: 4381297
    Abstract: Compounds of the formula ##STR1## wherein X is an imino acid or ester are disclosed as useful hypotensive agents due to their angiotensin converting enzyme inhibition activity.
    Type: Grant
    Filed: May 4, 1981
    Date of Patent: April 26, 1983
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Donald S. Karanewsky, Edward W. Petrillo, Jr.
  • Patent number: 4375554
    Abstract: A process for preparing an amidinecarboxylic acid which comprises reacting, in water, an alkoxyiminoacetic acid ester represented by the formula ##STR1## (wherein R.sup.1 and R.sup.2 individually represent an alkyl group of 1 to 4 carbon atoms) with an amine represented by the formulaR.sup.3 --NH.sub.2(wherein R.sup.3 represents a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, an alkenyl group of 2 to 4 carbon atoms, a cycloalkyl group of 5 to 7 carbon atoms or a benzyl group).
    Type: Grant
    Filed: November 5, 1981
    Date of Patent: March 1, 1983
    Assignee: UBE Industries Ltd.
    Inventors: Kiyoshi Fukui, Kiyomi Okimoto
  • Patent number: 4371706
    Abstract: Alkali metal aminoalkanoate is prepared by contacting in the presence of an alkali metal carboxylate a reaction mixture in which there is at least one alkali metal hydroxide, at least one lactam, and water. Arylene sulfide polymer is prepared by contacting at polymerization conditions a reaction mixture that contains at least one alkali metal aminoalkanoate prepared as described above; at least one polyhalo-substituted aromatic compound; at least one organic amide as solvent and H.sub.2 S. In an embodiment of the polymerization the organic amide used as solvent can be the same as the lactam from which the alkali metal aminoalkanoate was produced.
    Type: Grant
    Filed: October 22, 1981
    Date of Patent: February 1, 1983
    Assignee: Phillips Petroleum Company
    Inventors: James T. Edmonds, Jr., Lacey E. Scoggins
  • Patent number: 4370488
    Abstract: The invention includes novel alkali metal complex compounds (and processes for their preparation) which are useful, inter alia for the hydrogenation of alkali metals at room temperature or below room temperature to form hydrides or nitrides.
    Type: Grant
    Filed: June 18, 1981
    Date of Patent: January 25, 1983
    Assignee: Studiengesellschaft Kohle mbH
    Inventor: Borislav Bogdanovic
  • Patent number: 4352751
    Abstract: Species-linked diamine triacetic acids of the formula ##STR1## wherein T is an organic species containing at least one amine, hydroxyl, or thiol functional group, L is the residue of at least one of those functional groups and R is a two or more atom long covalent bridge, are disclosed. Methods for their preparation, for the preparation of metal chelates from them and for the use of the chelates are also disclosed. In a preferred embodiment, the metal ions employed in the formation of the chelates are rare earth metal ions capable of forming fluorescent chelates which can in turn be employed in fluoroassay techniques.
    Type: Grant
    Filed: September 10, 1979
    Date of Patent: October 5, 1982
    Assignee: Analytical Radiation Corporation
    Inventors: Irwin Wieder, Robert H. Wollenberg
  • Patent number: 4347379
    Abstract: Numerous alpha-carboxylic acids are prepared in a liquid medium by the reaction of an organic compound having at least one reactive hydroxyl or thiol group, with a monoketone, and a haloform, in the presence of a phase transfer catalyst and an alkali metal hydroxide. The term "alpha-alkoxycarboxylic acids" includes alpha-phenoxycarboxylic acids, alpha-thioalkoxycarboxylic acids and alpha-thiophenoxycarboxylic acids. Specific substituents on the beta carbon atom of an alpha-alkoxycarboxylic (or "2-alkoxycarboxylic") acid reaction product formed in this novel synthesis, are introduced by appropriate choice of the ketone reactant; alkoxy and phenoxy substituents on the alpha carbon atom of a 2-alkoxycarboxylic acid are introduced by appropriate choice of the organic compound having a hydroxyl or thiol group. De-alkoxylation of the 2-alkoxycarboxylic acid yields alpha-beta monoolefinically unsaturated carboxylic acids which are necessarily alpha substituted, and may also be beta-substituted.
    Type: Grant
    Filed: March 10, 1980
    Date of Patent: August 31, 1982
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4338461
    Abstract: A novel process for producing D-2-amino-2-(1,4-cyclohexadienyl)-acetic acid useful as an intermediate compound for producing 6-aminopenicillanic acid or 7-aminocephalosporanic acid is disclosed.
    Type: Grant
    Filed: March 19, 1981
    Date of Patent: July 6, 1982
    Assignee: Nippon Kasei Chemical Co., Ltd.
    Inventors: Kunio Unuma, Hiroyasu Saito, Jihei Inomata, Saburo Takizawa
  • Patent number: 4337262
    Abstract: Hydantoins of formula (I) ##STR1## have biological properties related to those of naturally occurring prostaglandins and may be used in medicine, for example in the treatment of thrombosis.
    Type: Grant
    Filed: November 30, 1978
    Date of Patent: June 29, 1982
    Assignee: Burroughs Wellcome Co.
    Inventors: Norman Whittaker, Albert G. Caldwell
  • Patent number: 4334087
    Abstract: A novel process for the manufacture of .alpha.-ketocarboxylic acids which comprises the reaction of oximinohalide with cyanide ion to form oximinonitrile which is reacted with hydroxide ion to form oximinoacid and hydrolysis thereof to the .alpha.-ketoacid.
    Type: Grant
    Filed: September 11, 1980
    Date of Patent: June 8, 1982
    Assignee: Zoecon Corporation
    Inventors: Ted A. Baer, Jeffrey N. Labovitz
  • Patent number: 4324886
    Abstract: Alkali metal aminoalkanoate is prepared by contacting in the presence of an alkali metal carboxylate a reaction mixture in which there is at least one alkali metal hydroxide, at least one lactam, and water. Arylene sulfide polymer is prepared by contacting at polymerization conditions a reaction mixture that contains at least one alkali metal aminoalkanoate prepared as described above; at least one polyhalo-substituted aromatic compound; at least one organic amide as solvent and H.sub.2 S. In an embodiment of the polymerization the organic amide used as solvent can be the same as the lactam from which the alkali metal aminoalkanoate was produced.
    Type: Grant
    Filed: May 6, 1980
    Date of Patent: April 13, 1982
    Assignee: Phillips Petroleum Company
    Inventors: James T. Edmonds, Jr., Lacey E. Scoggins
  • Patent number: 4322550
    Abstract: Various mercaptoalkanoic acids are recovered from an aqueous medium or water in which they are contained by a liquid-liquid solvent extraction operation employing at least one of an alkanoic acid ester and an alkylene glycol ether. In one embodiment, thioglycolic acid has been extracted with ethyl acetate. In another embodiment, it has been recovered with ethylene glycol monoethyl ether acetate. In a further embodiment, it has been recovered with diethylene glycol diethyl ether.
    Type: Grant
    Filed: October 3, 1980
    Date of Patent: March 30, 1982
    Assignee: Phillips Petroleum Company
    Inventor: James B. Kimble
  • Patent number: 4315031
    Abstract: This invention relates to thiosubstituted cyclic amino acids, to a process for their preparation and to pharmaceutical compositions containing them together with an inert non toxic pharmaceutical carrier.
    Type: Grant
    Filed: August 28, 1978
    Date of Patent: February 9, 1982
    Assignee: Science Union et Cie
    Inventors: Michel Vincent, Georges Remond, Jacques Bure
  • Patent number: 4297489
    Abstract: Certain 7-acylamido-3-(1-carboxy-loweralkyl-tetrazol-5-ylthiomethyl)-3-cephem-4-ca rboxylic acids and their salts and easily hydrolyzed esters of the 4-carboxyl group were synthesized and found to be potent antibacterial agents which exhibited good aqueous solubility. In a preferred embodiment the 7-substituent was 2'-aminomethylphenylacetamido.
    Type: Grant
    Filed: June 27, 1975
    Date of Patent: October 27, 1981
    Assignee: Bristol-Myers Company
    Inventors: William J. Gottstein, Murray A. Kaplan, Alphonse P. Granatek
  • Patent number: 4281119
    Abstract: An apparatus and process useful in direct fluorination of a variety of compositions, as well as the fluorinated compositions themselves, are disclosed.The apparatus comprises a cryogenic zone reactor, such as a packed column reactor, suitably divided into a plurality of independently controllable cryogenic temperature zones. Means are also provided to introduce a reactant to be fluorinated as well as to introduce a mixture of fluorine gas and an inert gas.New fluorinated compounds are also disclosed. These include: perfluoro-2-methoxyethyl ether; perfluoro-1,4-dioxane; perfluoro-2,5-diketohexane; perfluorohexamethylethane; and monohydropentadecafluoroadamantane.Additionally, new syntheses for trifluoroacetic acid, a commercially significant bulk chemical, are disclosed. One synthesis comprises producing perfluoroethyl acetate by direct fluorination using a cryogenic zone reactor, followed by hydrolysis of perfluoroethyl acetate. Two moles of the acid are produced for each mole of ester.
    Type: Grant
    Filed: June 23, 1976
    Date of Patent: July 28, 1981
    Assignee: Massachusetts Institute of Technology
    Inventors: Richard J. Lagow, James L. Adcock, Norma J. Maraschin
  • Patent number: 4275220
    Abstract: A process for preparing .alpha.-amino acids or ester thereof having an .alpha.-vinyl substituent and certain intermediates are disclosed.
    Type: Grant
    Filed: August 6, 1979
    Date of Patent: June 23, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Arthur A. Patchett, William J. Greenlee
  • Patent number: 4265819
    Abstract: A process for the preparation of a dihalogenovinylcyclopropanecarboxylic acid or an ester thereof, of the formula ##STR1## in which Hal each independently is fluorine, chlorine or bromine,R.sup.1 and R.sup.2 each independently is hydrogen or C.sub.1-4 -alkyl, or R.sup.1 and R.sup.2 together with the adjacent carbon atom form a cycloaliphatic ring with up to 7 carbon atoms, andR.sup.3 is hydrogen, C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl,which comprises reacting a 3-chloro-2-(2',2'-dihalovinyl)propanecarboxylic acid ester of the formula ##STR2## in which R.sup.4 is C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl,with a base. The propane carboxylic acid esters are new and may be formed in situ by reacting a 3-(2',2'-dihalovinyl)-.gamma.-butyrolactone of the formula ##STR3## with a chlorinating agent and then with an alcohol of the formula R.sup.4 --OH.
    Type: Grant
    Filed: September 13, 1979
    Date of Patent: May 5, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventor: Reinhard Lantzsch
  • Patent number: 4259250
    Abstract: The present invention provides novel thromboxane analogs and intermediates. Particularly, the present invention provides novel 11a-homo-PG intermediates for preparing 11a-methano TXA.sub.2 compounds.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4256761
    Abstract: Compounds of the structure: ##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,n is an integer from 0 to 4 inclusive,M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycyclo-alkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, dialkylamino-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, or fused heteroaryl-cycloalkyl-alkyl,Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is hydrogen, alkanoyl, carboxylalkanoyl, hydroxyalkanoyl, amino-alkanoyl, cyano, amidino, carbalkoxy, ZS, or ##STR2## wherein Z is hydrogen, alkyl, hyroxyalkyl, aminoalkyl or the radical ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.
    Type: Grant
    Filed: July 13, 1979
    Date of Patent: March 17, 1981
    Assignee: USV Pharmaceutical Corporation
    Inventors: John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
  • Patent number: 4250183
    Abstract: N-substituted .omega.-aminoalkanoyl-.omega.-aminoalkanoic acids and their pharmacologically-acceptable salts (with a base) are useful, e.g., in pharmaceutical-composition form for the treatment or prophylaxis of diseases which are based on inadequate performance of the pancreas, the bile and/or the liver. The compounds are prepared, e.g., by reacting an N-(mono- or di-substituted) .omega.-amino-alkanoic acid with an N-(unsubstituted or monosubstituted) .omega.-aminoalkanoic acid.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: February 10, 1981
    Assignee: BYK Gulden Lomberg Chemische Fabrik GmbH
    Inventor: Walter Krastinat
  • Patent number: 4243678
    Abstract: Compounds of the formula ##STR1## wherein R is (a) optionally-substituted and optionally-hydrogenated biphenylyl, (b) optionally-substituted and optionally-hydrogenated bicyclic aryl having from 8 to 12 ring carbon atoms or (c) a radical of the formula ##STR2## R.sup.1 is aliphatic hydrocarbyl, alicyclic hydrocarbyl or optionally-substituted phenyl;R.sup.2 is --H or lower aliphatic hydrocarbyl;R.sup.3 is --H, lower alkyl, cycloalkyl, optionally-substituted phenyl or, with R.sup.4, alkylene;R.sup.4 is lower alkyl, cycloalkyl, optionally-substituted phenyl, optionally-(nuclearly)-substituted phenalkyl or, with R.sup.3, alkylene;or R.sup.2,R.sup.3 and R.sup.4, together with the carbon to which each is bound, are adamantyl; andn is 3, 4 or 5;and salts thereof with a base are pharmacologically active. Esters thereof are valuable intermediates for the preparation of the pharmacologically-active compounds. Physiologically-acceptable embodiments are administered, e.g.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: January 6, 1981
    Assignee: Byk Gulden Lomberg Chemische Fabrik GmbH
    Inventor: Walter Krastinat
  • Patent number: 4240823
    Abstract: Compounds of the formula: ##STR1## in which R.sub.1 is hydrogen, optionally halogenated alkyl, optionally halogenated cycloalkyl, optionally halogenated alkenyl, optionally halogenated aralkenyl or aryloxyalkenyl mono or bicyclic aryl (optionally substituted by halogen, alkyl, trifluoromethyl, nitro, cyano, amino, hydroxyl, alkoxy, aminosulphonyl or alkylcarbonyloxy), or monocyclic or bicyclic heterocyclic of 5-11 chain members and having one or two hetero-atoms (optionally substituted), and R.sub.2 is a carboxylic acid group or a salt or ester thereof, is found to have plant growth regulating activity.
    Type: Grant
    Filed: March 1, 1977
    Date of Patent: December 23, 1980
    Assignee: Philagro S.A.
    Inventors: Claude Clapot, Jean Vial, Jacqueline Mourier, Jean C. Boch
  • Patent number: RE30885
    Abstract: Carboxylic acid terminated diamides and alkali metal, ammonium or amine salts thereof are provided which are derived from the reaction of organic polycarboxylic acids and polyoxyalkylene diamines. The diamides have lubricating properties and are especially useful in aqueous metal working fluids.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: March 23, 1982
    Assignee: Cincinnati Milacron Inc.
    Inventor: Walter E. Rieder