Piperazines (i.e., Fully Hydrogenated 1,4-diazines) Patents (Class 544/358)
  • Patent number: 4504666
    Abstract: Disclosed is an improvement in process for oxidizing an aromatic amine to form an aromatic amine oxide wherein a reaction mixture of the aromatic amine and a peracid is formed and maintained under non-aqueous conditions at a temperature and for a time adequate until substantially all of the aromatic amine is formed into said aromatic amine oxide. The provision for eliminating water from the reaction mixture leads to near quantitative yields of aromatic amine oxide.
    Type: Grant
    Filed: June 4, 1982
    Date of Patent: March 12, 1985
    Assignee: Sherex Chemical Company, Inc.
    Inventors: Gary W. Earl, Howard M. Hickman
  • Patent number: 4503072
    Abstract: Compounds of general structural formula: ##STR1## wherein Q is: ##STR2## or pharmaceutically acceptable salts, C.sub.1-3 alkyl esters or .alpha.-monoglyceride when Q is a dihydroxy acid are useful as antihypercholesterolemic agents for the treatment of atherosclerosis, familial hypercholesterolemia, hyperlipemia and like diseases. They also have useful antifungal activity.
    Type: Grant
    Filed: June 18, 1984
    Date of Patent: March 5, 1985
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Ta-Jyh Lee, Robert L. Smith, Alvin K. Willard
  • Patent number: 4474783
    Abstract: A compound having the formula ##STR1## in which R is hydrogen or alkyl having 1 to 4 carbon atoms; R.sub.1 is hydrogen, alkyl having 1 to 5 carbon atoms, cycloalkylmethyl in which the cycloalkyl group has from 3 to 6 carbon atoms, 2-hydroxyethyl, alkoxycarbonyl in which the alkoxy group has 1 or 2 carbon atoms, 2-carboxypropyl, N-benzyl-2-carbamoyl propyl, phenyl, phenyl substituted by methoxy, trifluoromethyl or acetyl, benzyl, benzyl substituted by halogen, benzoyl, benzoyl substituted by three methoxy groups, 3,5-dimethoxy-4-acetoxy or 3,5-dimethoxy-4-ethoxycarbonyloxy, cinnamoyl, cinnamoyl in which the phenyl ring is substituted with trifluoromethyl or by one or more methoxy groups, phenoxyacetyl, phenoxyacetyl in which the phenyl ring is substituted with halogen or methoxy, and ##STR2## in which m is 2 or 3 and R.sub.2 and R.sub.
    Type: Grant
    Filed: September 25, 1981
    Date of Patent: October 2, 1984
    Assignee: Innothera
    Inventors: Max F. Robba, Michel E. Aurousseau
  • Patent number: 4469694
    Abstract: 2-(1-Piperazinyl)-2,4,6-cycloheptatrien-1-one derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions of the derivatives are disclosed. The derivatives exhibit dopamine-receptor stimulating activity in a mammal and are useful for treating hyperprolactinemia, galactorrhea, amenorrhea, impotence, Parkinsonism, diabetes, acromegaly, hypertension and other central nervous system disorders.
    Type: Grant
    Filed: February 25, 1980
    Date of Patent: September 4, 1984
    Assignee: Ayerst, McKenna & Harrison Inc.
    Inventors: Jehan F. Bagli, Tibor Bogri, Katherine Voith
  • Patent number: 4455401
    Abstract: Novel compounds have been discovered in which a bis compound of a polysubstituted 2-keto-1,4-diazacycloalkane ("2KDZC") provides a bridge between diisocyanate groups so as to form an oligomeric 2KDZC-urethane ("2K-U" oligomer) having from 2 to about 15 repeating units. The bis compound bridge itself consists essentially of two distally linked polysubstituted 2KDZC moieties, and the 2K-U oligomer formed consists essentially of two 2KDZC moieties linked through their N.sup.1 atoms, which moieties in turn are distally linked to urethane groups through the N.sup.4 atoms of the 2KDZC. Such 2K-U oligomers unexpectedly contain a self-limiting number of 2K-U repeating units which happens to provide 2K-U oligomers which are desirable and highly effective u-v light stabilizers in organic materials.
    Type: Grant
    Filed: May 6, 1982
    Date of Patent: June 19, 1984
    Assignee: The B. F. Goodrich Company
    Inventors: Pyong N. Son, John T. Lai
  • Patent number: 4452798
    Abstract: Certain substituted phenylpiperazine compounds useful as antihypertensive agents are described. Methods for their preparation and use are disclosed.
    Type: Grant
    Filed: June 22, 1982
    Date of Patent: June 5, 1984
    Assignee: Warner-Lambert Company
    Inventor: Donald R. Maxwell
  • Patent number: 4448962
    Abstract: This invention relates to new compounds of value as antibacterial agents. More particularly, it relates to quinoline carboxylic acid derivatives, the hydrates and the acid or alkali addition salts thereof.
    Type: Grant
    Filed: October 14, 1981
    Date of Patent: May 15, 1984
    Assignee: Kyorin Seiyaku Kabushiki Kaisha
    Inventors: Tsutomu Irikura, Seigo Suzue, Akira Ito, Hiroshi Koga
  • Patent number: 4407823
    Abstract: Phenylacetic acid derivatives of the formula ##STR1## wherein n is an integer of 2 to 5; ##STR2## R.sub.1 is hydrogen, halogen, trifluoromethyl, nitro or amino; R.sub.2 and R.sub.3 each independently is hydrogen or lower alkyl; or together form an ethylene group;X.sub.1 represents two hydrogen atoms or an oxo group; andY.sub.1 is cyano, hydroxyamidocarbonyl, carbamoyl, 5-tetrazolyl or carboxyl;and for derivatives wherein Y is carboxyl, salts thereof with physiologically compatible bases, esters thereof from physiologically acceptable alcohols and amides thereof from physiologically acceptable amines have valuable pharmacological activity, e.g., as antiinflammatory agents.
    Type: Grant
    Filed: November 5, 1979
    Date of Patent: October 4, 1983
    Assignee: Schering Aktiengesellschaft
    Inventors: Gerald Kirsch, Joachim-Friedrich Kapp, Clemens Rufer
  • Patent number: 4397855
    Abstract: New 4-(substituted-.alpha., .alpha.-dimethyl-1-piperazine pentanoic acids and derivatives which are useful as anti-arteriosclerotic agents are disclosed. These compounds elevate the high density lipoprotein fraction of cholesterol, and also lower the low density lipoprotein fraction of cholesterol.
    Type: Grant
    Filed: June 26, 1981
    Date of Patent: August 9, 1983
    Assignee: Warner-Lambert Company
    Inventor: Ila Sircar
  • Patent number: 4394159
    Abstract: This invention is directed to 2-chloro-6-nitro-aniline compounds of the formula ##STR1## wherein A represents hydrogen, a straight or branched alkyl radical having from 1 to 6 carbon atoms a cycloalkyl radical having from 3 to 6 carbon atoms, a chlorine-substituted or hydroxyl-sustituted alkyl radical having from 2 to 6 carbon atoms, or an allyl or trifluoroacetyl group,B represents hydrogen or a methyl, ethyl, n-propyl, or isopropyl group, orA and B represent together an alkylene radical optionally interrupted by oxygen, .dbd.NH or, .dbd.NCH.sub.3, and having up to 5 members, or the group .dbd.CH-N(CH.sub.3).sub.2,R represents hydrogen, fluorine, chlorine, or bromine or a trifluoromethyl, methyl, or methoxy group, and X represents oxygen or sulphur,and novel herbicidal compositions containing these compounds as active ingredients.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: July 19, 1983
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Wolfgang Buck, Richard Sehring, Gerbert Linden, Sigmund Lust
  • Patent number: 4348522
    Abstract: N-(Phosphonoacetyl)-L-aspartic acid (PALA) compounds, especially novel PALA compounds, and methods for their preparation in large amounts are disclosed. These methods include preparation of certain PALA compounds such as PALA dibenzyl ester, disodium PALA, and the cyclohexylamine salt of dibenzyl PALA.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: September 7, 1982
    Assignee: Starks Associates, Inc.
    Inventors: Robert J. Schultz, Fred W. Starks
  • Patent number: 4344946
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.1 ', which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 2 carbon atoms;R.sub.2 and R.sub.2 ', which may be identical to or different from each other, are each hydrogen or ##STR2## but other than both hydrogen at the same time, where A is alkylene of 1 to 2 carbon atoms,R.sub.5 is hydrogen, lower alkyl, lower alkylamino-lower alkyl, lower alkoxy-lower alkyl, hydroxycarbonyl-lower alkyl, cycloalkyl of 5 to 8 carbon atoms, lower alkyl-cycloalkyl of 5 to 8 carbon atoms, phenyl or morpholino;R.sub.6 is hydrogen, lower alkyl, lower alkylamino-lower alkyl or lower alkoxy-lower alkyl; orR.sub.5 and R.sub.
    Type: Grant
    Filed: August 28, 1980
    Date of Patent: August 17, 1982
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Ernest Cullen, Genus Possanza, Patrick B. Stewart
  • Patent number: 4342767
    Abstract: Substances isolated after cultivation of a microorganism belonging to the genus Aspergillus in a culture medium comprise compounds which have structures: ##STR1## Together with salts and esters of the carboxylic acid, these compounds form a class of highly active hypocholesteremic and hypolipemic medicaments.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: August 3, 1982
    Assignee: Merck & Co., Inc.
    Inventors: George Albers-Schonberg, Richard L. Monaghan, Alfred W. Alberts, Carl H. Hoffman
  • Patent number: 4340540
    Abstract: To prepare basic dyestuffs of the general formula ##STR1## in which A and B independently of one another represent a hetero-aromatic radical or a radical of the general formula ##STR2## compounds of the general formulaA--CH.sub.2 --BA and B have the abovementioned meaning,are oxidized with oxygen in the presence of a nucleophilic compound of the general formulaD--Hand in the presence of catalytic amounts of benzoquinones substituted by halogen or cyano or of phenanthrenequinones substituted by nitro, and in the presence of catalytic amounts of nitrogen oxides--with the exception of dinitrogen monoxide--or of substances which produce such nitrogen oxides under the reaction conditions.
    Type: Grant
    Filed: June 26, 1980
    Date of Patent: July 20, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventor: Karl H. Hermann
  • Patent number: 4324724
    Abstract: A process for the manufacture of polyalkylenepolyamines by reacting a primary or secondary amine with a compound of the formula ##STR1## where X is --Cl, --Br, or --OSO.sub.3 H and R.sup.1 and R.sup.2 are H or saturated alkyl of 1 to 4 carbon atoms, and with at least the stoichiometric amount, based on the compound of the formula I, of an aqueous solution, of from 15 to 45 percent strength, of an alkali metal hydroxide or alkaline earth metal hydroxide, at from 60.degree. to 200.degree. C., cooling the reaction mixture to a temperature at which 2 aqueous phases form, and separating off the upper phase, containing polyalkylenepolyamnines. The rate of reaction can be increased by adding catalytic amounts of compounds which initiate the polymerization of alkyleneimines.
    Type: Grant
    Filed: October 2, 1978
    Date of Patent: April 13, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Mueller, Klaus Wulz, Karl-Heinz Beyer, Werner Streit
  • Patent number: 4322437
    Abstract: The present invention relates to a compound of formula I, ##STR1## wherein A is straight chain alkylene of 2 to 4 carbon atoms, or straight chain alkenylene of 2 to 4 carbon atoms,n is 1, 2 or 3,R is hydrogen or halogen of atomic number from 9 to 35, andeither (i) R.sub.1 is a group of formula II, ##STR2## wherein R.sub.2 and R.sub.3, independently, are hydrogen or alkyl of 1 to 4 carbon atoms, andR.sub.4 is alkyl of 1 to 4 carbon atoms, alkoxyalkyl of 2 to 5 carbon atoms, alkylthioalkyl of 2 to 5 carbon atoms, phenylalkyl or phenoxyalkyl or phenylthioalkyl, wherein the alkyl moiety has from 1 to 3 carbon atoms, or phenyl, the phenyl ring of each of the last four radicals being unsubstituted or mono-substituted by, or disubstituted independently by, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, hydroxy or halogen of atomic number from 9 to 35, andR.sub.5 is hydrogen,or (ii) R.sub.1 and R.sub.
    Type: Grant
    Filed: May 10, 1977
    Date of Patent: March 30, 1982
    Assignee: Sandoz Ltd.
    Inventors: Richard Berthold, Trevor G. Payne
  • Patent number: 4322530
    Abstract: A process for alkylating a polyamine by contacting, in a liquid media, a polyamine, an olefinic compound, carbon monoxide, and a hydrogen source in the presence of a catalytic amount of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, rhodium carbonyls and ligands thereof at a temperature of from about 50.degree. C. to 250.degree. C. and at a pressure of from about 30 to about 300 atmospheres.
    Type: Grant
    Filed: February 22, 1980
    Date of Patent: March 30, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz
  • Patent number: 4316841
    Abstract: Process for production of polyalkylene polyamines, preferably non-cyclic polyalkylene polyamines, by reforming of other polyalkylene polyamines. The reforming process is effected by reacting the polyalkylene polyamine starting material in the presence of a phosphate, preferably a boron phosphate, catalyst at elevated temperature and pressure and in the presence of sufficient water and sufficient catalyst, for a reaction period and under reaction conditions otherwise adapted to bring about the desired reforming reaction.
    Type: Grant
    Filed: December 8, 1980
    Date of Patent: February 23, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael E. Ford, Thomas A. Johnson
  • Patent number: 4316840
    Abstract: Process for production of polyalkylene polyamines, preferably non-cyclic polyalkylene polyamines, by reforming of other polyalkylene polyamines. The reforming process is effected by reacting the polyalkylene polyamine starting material in the presence of a metal nitrate or sulfate, preferably a sulfate, catalyst at elevated temperature and pressure and in the presence of sufficient water and sufficient catalyst, for a reaction period and under reaction conditions otherwise adapted to bring about the desired reforming reaction.
    Type: Grant
    Filed: November 25, 1980
    Date of Patent: February 23, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael E. Ford, Thomas A. Johnson
  • Patent number: 4310429
    Abstract: Novel .alpha.-aminoacetamides are powerful stabilizers for organic materials subject to oxygen and heat degradation, and particularly for synthetic natural rubber and synthetic ester lubricants. A wide range of substituents on the amine and amide N atoms, and also on the saturated carbon atom, yields an array of stabilizers having a wide range of compatibility in compositions comprising various synthetic resinous compounds to be stabilized.Novel syntheses are provided utilizing at least one amine nucleophilic agent, a dichlorocarbene ion generating agent, and an alkoxide ion generating agent, which together in the presence of aqueous alkali and an onium salt, yield novel .alpha.-aminoacetamides in which a wide choice of substituents may be introduced. The nucleophilic agent may be a primary or secondary amine, or one of each. The dichlorocarbene ion generating agent is a haloform. The alkoxide ion generating agent may be a ketone, an aldehyde, or a cyanohydrin which reacts with the haloform. An .alpha.
    Type: Grant
    Filed: June 19, 1978
    Date of Patent: January 12, 1982
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4306071
    Abstract: 1,4-Bis(2'-haloethyl)-1,4-diazabicyclo[2.2.1]-heptane derivatives, such as diperchlorate, dichloride, diacetate, dibenzoate, diascorbate, disalicylate, ditartrate, disaccharin, dihydrogen dimaleate, together with ethyl sulfonate and periodate.
    Type: Grant
    Filed: November 14, 1979
    Date of Patent: December 15, 1981
    Assignee: The United States of America as represented by the Department of Health & Human Services
    Inventors: George R. Pettit, Donald P. Gieschen, William E. Pettit
  • Patent number: 4284829
    Abstract: Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 14 C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.
    Type: Grant
    Filed: December 22, 1978
    Date of Patent: August 18, 1981
    Assignee: Pfizer Inc.
    Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4273937
    Abstract: Organic amine compositions which are substantially free of nitrosamine contaminants are provided which comprise an organic amine and an inhibiting amount of an inhibitor additive selected from the group consisting of 1,4-naphthoquinone, 1,4-naphthohydroquinone, alkyl-derivatives of said quinones, and mixtures of the same.
    Type: Grant
    Filed: December 19, 1979
    Date of Patent: June 16, 1981
    Assignee: Union Carbide Corporation
    Inventors: Mary L. Gum, Nancye D. Kearns
  • Patent number: 4271053
    Abstract: This invention relates to quaternary ammonium graft copolymers comprised of polymeric units characterized by the general formula: ##STR1## wherein n, y and z represent the relative molar equivalent fractions of each of the respective polymeric units in the graft copolymer, the sum of n, y and z being 1.0, the value of n varying from 0.00 to 0.99, the value of y varying from 0.00 to 0.99 and the value of z varying from 0.01 to 0.
    Type: Grant
    Filed: June 29, 1979
    Date of Patent: June 2, 1981
    Assignee: Union Carbide Corporation
    Inventors: Donald R. Kelsey, Russell L. Kreeger
  • Patent number: 4242344
    Abstract: Piperazinyl-imidazo[1,2-a]pyrazines, derived from reactions between halo-imidazo[1,2-a]pyrazines with piperazine derivatives, are found to be active anorexic, antidepressant, antihypertensive, analgesic, antiarrhythmic, and/or anti-smoking agents.
    Type: Grant
    Filed: September 7, 1979
    Date of Patent: December 30, 1980
    Assignee: Merck & Co., Inc.
    Inventor: William C. Lumma
  • Patent number: 4234730
    Abstract: Covers a process for preparing a mixture of piperazine and ethylenediamine by the hydrogenation reaction of monoethanolamine and ammonia utilizing a nickel-copper-chromium catalyst. The improvement of the invention involves predetermining the ratio of ethylenediamine to piperazine in the product mix by varying the hydrogen feed rate. Increasing said feed rate causes said ratio to decrease.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: November 18, 1980
    Assignee: Texaco Development Corp.
    Inventors: Thomas T. McConnell, Thomas H. Cour
  • Patent number: 4221919
    Abstract: Antiinflammatory substituted phenylacetic acids of low toxicity are prepared by reaction of a salt of an alkyl 3 chloro-4-hydroxyphenylacetate with a substituted benzyl halide in the presence of an inert organic solvent at elevated temperatures.
    Type: Grant
    Filed: April 24, 1979
    Date of Patent: September 9, 1980
    Assignee: SPOFA, United Pharmaceutical Works
    Inventors: Jaroslava Grimova, Oldrich Nemecek, Miroslav Kuchar, Bohumila Brunova
  • Patent number: 4216326
    Abstract: N-{3- and 4-[R.sub.1 -(phenyl)-C(.dbd.X)]-phenyl-lower-alkyl}amines, useful as anti-inflammatory agents, are prepared either by reduction of 3- or 4-[R.sub.1 -(phenyl)-CO]-phenyl-lower-alkanoylamines, which are also useful as anti-inflammatory agents; by benzoylating a phenyl-lower-alkylamine; by reaction of a 3- or 4-lithiophenyl-lower-alkylamine with a R.sub.1 -(phenyl)-carboxaldehyde, a R.sub.1 -(phenyl)-lower-alkyl ketone or a R.sub.1 -(phenyl)-carbonitrile or by transformations involving manipulations of a carbonyl or carbinol group.
    Type: Grant
    Filed: May 3, 1978
    Date of Patent: August 5, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Bernard L. Zenitz
  • Patent number: 4215070
    Abstract: N-(Phosphonoacetyl)-L-aspartic acid (PALA) compounds, especially novel PALA compounds, and methods for their preparation in large amounts are disclosed. These methods include preparation of certain PALA compounds such as PALA dibenzyl ester, disodium PALA, and the cyclohexylamine salt of dibenzyl PALA.
    Type: Grant
    Filed: October 25, 1978
    Date of Patent: July 29, 1980
    Assignee: Starks Associates, Inc.
    Inventors: Robert J. Schultz, Fred W. Starks
  • Patent number: 4212709
    Abstract: An acidic nickel electroplating bath containing brighteners and levelling agents, wherein the levelling agents are compounds of the formula I ##STR1## where N is a hetero-aromatic nitrogen base, R, R.sup.1 and R.sup.2 are hydrogen or alkyl, R.sup.3 is arylene, X is SO.sub.3.sup.-, Y is a neutralizing cation, n is from 1 to 3 and m is from 1 to 2.5.
    Type: Grant
    Filed: May 11, 1979
    Date of Patent: July 15, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Patsch, Dieter Schneider, Guenther Gotsmann, Albert Hettche
  • Patent number: 4166827
    Abstract: Antimicrobial compounds are disclosed having the formula:Z--B--Y--B--Zwherein B is carbamylguanidino or thiocarbamylguanidino; Y is an alkylene group which contains one to three nitrogen atoms or which contains two nitrogens as part of a cyclic structure; and Z can represent a number of groups such as alkyl, cycloalkyl, aryl and aralkyl.
    Type: Grant
    Filed: June 22, 1978
    Date of Patent: September 4, 1979
    Assignee: Cooper Laboratories, Inc.
    Inventor: Julius Diamond
  • Patent number: 4156779
    Abstract: What is disclosed is the method of making a monoenamine having a free hydroxy group which comprises reacting a lactone or a carboxylic acid containing an hydroxy group with an amine selected from the group consisting of 2-methyl piperazine, 1-(2-aminoethyl)-piperazine, 4-aminomethyl-piperidine, or 2,3-dimethyl-3-(gamma-aminopropyl)-piperidine to form the corresponding secondary amine containing an hydroxy group and then reacting said secondary amine with an aliphatic aldehyde or cyclic ketone to form said monoenamine.
    Type: Grant
    Filed: April 21, 1978
    Date of Patent: May 29, 1979
    Assignee: Schering Aktiengesellschaft
    Inventors: Christian Burba, Hans-Guenter Volland
  • Patent number: 4153794
    Abstract: Novel N-benzylpiperazine derivatives of the general formula ##STR1## wherein R.sup.1 and R.sup.2 are same or different and each stands for a hydrogen atom or an acyl group; R.sup.3 stands for a hydrogen atom, a carbamoyl group, an acyl group which is unsubstituted or substituted by mercapto or morpholino, or an alkyl group which is unsubstituted or substituted by hydroxy, aryl or aminocarbonyl represented by the formula ##STR2## wherein each of R.sup.4 and R.sup.5 is a hydrogen atom, a lower alkyl group having 1 to 3 carbon atoms or a cyclohexyl group, or R.sup.4 and R.sup.5 form a morpholino or piperidino ring together with the nitrogen atom adjacent thereto, and X stands for a halogen atom, and pharmaceutically acceptable acid addition salts thereof. These compounds and salts thereof have respiratory tract fluid secretion stimulatory properties and are useful as medicines such as respiratory tract fluid secretion stimulators.
    Type: Grant
    Filed: March 1, 1978
    Date of Patent: May 8, 1979
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Toshihiro Ishiguro, Yasushi Sanno
  • Patent number: 4146560
    Abstract: Covers a process for preparing polyamines from the corresponding polynitriles via a pelleted cobalt-copper-chromium hydrogenation catalyst which comprises contacting a polynitrile with hydrogen in presence of said catalyst and a stabilizing agent comprising a polyamine or a hydroxyl-amine whereby catalyst pellet disintegration is inhibited by the presence of said stabilizing agent.
    Type: Grant
    Filed: November 28, 1977
    Date of Patent: March 27, 1979
    Assignee: Texaco Development Corp.
    Inventors: John M. Larkin, Philip H. Moss
  • Patent number: 4123462
    Abstract: The present invention concerns a new nickel-rhenium catalyst and method of preparing said catalyst. The invention also relates to the catalytic amination of lower aliphatic alkane derivatives such as alkanemono-ols, alkanediols and alcoholamines utilizing the new nickel-rhenium catalyst.
    Type: Grant
    Filed: January 7, 1976
    Date of Patent: October 31, 1978
    Assignee: Union Carbide Corporation
    Inventor: Donald C. Best
  • Patent number: 4113726
    Abstract: Compounds are provided having the structure ##STR1## wherein n is 1 or 2, n.sup.1 is 0, 1 or 2 and n.sup.2 is 0, 1, 2 or 3, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be the same or different and can be hydrogen, lower alkyl, halolower alkyl, acyl, lower alkoxy-carbonyl ##STR2## amido ##STR3## or lower alkoxyalkylene, R can be lower alkoxy, lower alkyl or cycloalkyl, R.sub.8 can be hydrogen, lower alkyl, cycloalkyl, hydroxy, dialkylaminoalkyl or R.sub.9 O(CH.sub.2)q-. X is a single bond or a straight or branched bivalent aliphatic radical and Y is ##STR4## These compounds are useful in the treatment of hypertension.
    Type: Grant
    Filed: February 28, 1974
    Date of Patent: September 12, 1978
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Frederic Peter Hauck, Christopher Michael Cimarusti
  • Patent number: RE31717
    Abstract: This invention is directed to 2-chloro-6-nitro-aniline compounds of the formula ##STR1## wherein A represents hydrogen, a straight or branched alkyl radical having from 1 to 6 carbon atoms a cycloalkyl radical having from 3 to 6 carbon atoms, a chlorine-substituted or hydroxyl-substituted alkyl radical having from 2 to 6 carbon atoms, or an allyl or trifluoroacetyl group,B represents hydrogen or a methyl, ethyl, n-propyl, or isopropyl group, orA and B represent together an alkylene radical optionally interrupted by oxygen, .dbd.NH or, .dbd.NCH.sub.3, and having up to 5 members, or the group.dbd.CH--N(CH.sub.3).sub.2,R represents hydrogen, fluorine, chlorine, or bromine or a trifluoromethyl, methyl, or methoxy group, and X represents oxygen or sulphur,and novel herbicidal compositions containing these compounds as active ingredients.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: October 30, 1984
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Wolfgang Buck, Richard Sehring, Gerbert Linden, Sigmund Lust