Nitrogen Attached Indirectly To The Piperazine Ring By Nonionic Bonding Patents (Class 544/402)
  • Patent number: 4314062
    Abstract: This invention relates to the manufacture of dicyanopiperazine. More particularly, it relates to inexpensive, ecologically desirable procedures based on the controlled reaction of piperazine with a cyanogen halide in water.
    Type: Grant
    Filed: April 15, 1980
    Date of Patent: February 2, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Richard B. Lund
  • Patent number: 4301186
    Abstract: This invention relates to new ammonium salts of .alpha.-ketocarboxylic acids, to their use for the production of amines in situ by photochemical decomposition and to photochemically hardenable coating compositions containing these ammonium salts.
    Type: Grant
    Filed: June 28, 1979
    Date of Patent: November 17, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder
  • Patent number: 4292321
    Abstract: Compounds of the formula ##STR1## where Q is defined hereinafter and X and Y are hydrogen, halogen, lower alkyl, nitro are useful as neuroleptics.
    Type: Grant
    Filed: January 10, 1980
    Date of Patent: September 29, 1981
    Assignee: Warner-Lambert Company
    Inventor: Ian C. Pattison
  • Patent number: 4274837
    Abstract: Fuel compositions for internal combustion engines are provided containing deposit control additives which maintain cleanliness of intake systems without contributing to combustion chamber deposits. The additives are hydrocarbylpoly(oxyalkylene) aminocarbamates comprising a hydrocarbyl-terminated poly(oxyalkylene) moiety composed of 2-5 carbon oxyalkylene units and one or more 9-30 carbon oxyalkylene groups. Certain additives also find use as dispersants in lubricating oils.
    Type: Grant
    Filed: July 2, 1979
    Date of Patent: June 23, 1981
    Assignee: Chevron Research Company
    Inventor: Jennifer E. Lilburn
  • Patent number: 4269837
    Abstract: Novel guanylamidines and the pharmaceutically acceptable acid addition salts thereof having activity as hypoglycemic agents are disclosed.
    Type: Grant
    Filed: February 19, 1980
    Date of Patent: May 26, 1981
    Assignee: Pfizer Inc.
    Inventors: David S. Watt, Jeffrey L. Ives
  • Patent number: 4264770
    Abstract: Compounds of general formula: ##STR1## particularly 1,4-bis-piperonylpiperazine, are obtained with high yields by reacting equimolar quantities of piperazine and of a chloride Ar--CH.sub.2 --Cl in the presence of water, under agitation, and in the presence of a cationic surfactant.
    Type: Grant
    Filed: April 27, 1979
    Date of Patent: April 28, 1981
    Assignee: Farmaceutici Geymonat Sud S.P.A.
    Inventors: Giancarlo Scapini, Gian P. Gardini, Armando Raimondi, Placido Poidomani
  • Patent number: 4259334
    Abstract: The invention relates to compounds having the formula: ##STR1## in which: the substituents R.sub.1, R.sub.2 and R.sub.3 represent independently from each other a hydrogen atom, a halogen atom, a trifluoromethyl radical, a saturated or unsaturated straight- or branched-chain C.sub.1-6 alkyl radical, a C.sub.1-6 alkoxy radical the alkyl moiety of which may be saturated or unsaturated and straight- or branched-chained, a benzyloxy radical or a hydroxy radical;the substituents R.sub.5, R.sub.6 and R.sub.7 represent independently from each other a hydrogen atom, a halogen atom, a trifluoromethyl radical, a straight- or branched-chain saturated or unsaturated C.sub.1-6 alkyl radical, a C.sub.1-6 alkoxy radical the alkyl moiety of which may be saturated or unsaturated and straight- or branched-chained, or a hydroxy radical;the substituent R.sub.4 represents a hydrogen atom, a C.sub.
    Type: Grant
    Filed: April 5, 1979
    Date of Patent: March 31, 1981
    Assignee: Laroche Navarron S.A.
    Inventors: Jean C. Pascal, Henri Pinhas
  • Patent number: 4256800
    Abstract: The antistatic composition for application to flat fibrous articles such as textiles, carpets, fabrics and the like which comprises a salt of a polymeric acid with an amine of the general formula ##STR1## wherein A=H, --OR.sub.2, ##STR2## R.sub.1 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.2 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.3 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.
    Type: Grant
    Filed: January 18, 1978
    Date of Patent: March 17, 1981
    Assignee: Chemische Fabrik Stockhausen & Cie
    Inventors: Dolf Stockhausen, Reinmar Peppmoller
  • Patent number: 4246260
    Abstract: The invention relates to new substituted o-phenylenediamine derivatives of the general formula ##STR1## in which R represents optionally substituted alkyl, optionally substituted alkenyl or optionally substituted alkinyl,X represents O, S, SO or SO.sub.2 andR.sup.1 and R.sup.2 are different from one another and individually represent ##STR2## in which R.sup.3 and R.sup.4 are identical or different and represent alkyl andR.sup.5 represents hydrogen, optionally substituted alkyl or optionally substituted alkoxy, and salts thereof.Also included in the invention are (1) methods for preparing the above-described compounds, (2) compositions containing the above-described compounds and (3) methods for the treatment of helminthiasis.
    Type: Grant
    Filed: March 19, 1979
    Date of Patent: January 20, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Kolling, Ekkehard Niemers, Hartmund Wollweber, Herbert Thomas
  • Patent number: 4235914
    Abstract: Butyrophenone compounds having excellent psychotropic activity and represented by the formula: ##STR1## wherein Z is defined hereinbelow.
    Type: Grant
    Filed: October 17, 1978
    Date of Patent: November 25, 1980
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kikuo Sasajima, Keiichi Ono, Hisao Yamamoto
  • Patent number: 4233168
    Abstract: Lubricant compositions for internal combustion engines are provided containing dispersant additives which prevent sludge and varnish formation in the crankcase. The additives are oil-soluble poly(oxyalkylene) aminocarbamates comprising a hydrocarbyl-terminated poly(oxyalkylene) chain of 2-5 carbon oxyalkylene units.
    Type: Grant
    Filed: June 19, 1978
    Date of Patent: November 11, 1980
    Assignee: Chevron Research Company
    Inventors: Robert A. Lewis, Lewis R. Honnen
  • Patent number: 4216214
    Abstract: Novel derivatives of formula (I) and the pharmaceutically acceptable salts thereof. ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is a lower alkyl group, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached, form a saturated heterocyclic group optionally containing, in addition to the said nitrogen atom, a second hetero atom, a process for the preparation thereof, and their use as anti-histamine anti "H.sub.2 " agents.
    Type: Grant
    Filed: December 27, 1977
    Date of Patent: August 5, 1980
    Assignee: PRODESIN (Productos Esteve Internacional S.A.)
    Inventors: Antonio Esteve Subirana, Jose Esteve Soler
  • 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: 4209524
    Abstract: The invention provides new acetohydroxamic acid derivatives, having interesting properties on the central nervous system, of the formula: R.sub.1 R.sub.2 R.sub.3 C--CO--NHOH, in which R.sub.2 and R.sub.3 are each hydrogen or C.sub.1-6 alkyl, and R.sub.1 is C.sub.1-6 alkyl Z.sub.1 Z.sub.2 N (where Z.sub.1 and Z.sub.2 are each phenyl, substituted phenyl, or cycloalkyl), substituted hydantoinyl, benzhydroxylcarboxamido, Z.sub.3 CH.sub.2 --(where Z.sub.3 =optionally substituted aryl), Z.sub.4 --A-- (where Z.sub.4 is optionally substituted phenyl or naphthyl, and A is --NH--, --N(C.sub.1-4 alkyl)--, --N(C.sub.5-6 cycloalkyl)--, --NHCO--, --N(C.sub.1-4 alkyl(CO--, --N(C.sub.5-6 cycloalkyl)CO--, --CONH--, --CON(C.sub.1-4 alkyl)--, --CON(C.sub.5-6 cycloalkyl)-, --NHCONH--, --N(C.sub.5 H.sub.6)CONH--, or --N(substituted phenyl)CONH--, optionally substituted benzimidazolyl, or an optionally substituted tricyclic radical, and their metal and acid addition salts.
    Type: Grant
    Filed: August 4, 1978
    Date of Patent: June 24, 1980
    Assignee: Laboratoire L. Lafon
    Inventor: Louis Lafon
  • Patent number: 4209523
    Abstract: The invention provides new acetohydroxamic acid derivatives, having interesting properties on the central nervous system, of the formula: R.sub.1 R.sub.2 R.sub.3 C--CO--NHOH, in which R.sub.2 and R.sub.3 are each hydrogen or C.sub.1-6 alkyl, and R.sub.1 is C.sub.1-6 alkyl Z.sub.1 Z.sub.2 N (where Z.sub.1 and Z.sub.2 are each phenyl, substituted phenyl, or cycloalkyl), substituted hydantoinyl, benzhydroxylcarboxamido, Z.sub.3 CH.sub.2 -- (where Z.sub.3 =optionally substituted aryl), Z.sub.4 --A-- (where Z.sub.4 is optionally substituted phenyl or naphthyl, and A is --NH--, --N(C.sub.1-4 alkyl)--, --N(C.sub.5-6 cycloalkyl)--, --NHCO--, --N(C.sub.1-4 alkyl)CO--, --N(C.sub.5-6 cycloalkyl)CO--, --CONH--, --CON(C.sub.1-4 alkyl)--, --CON(C.sub.5-6 cycloalkyl)--, --NHCONH--, --N(C.sub.5 H.sub.6)CONH--, or --N(substituted phenyl)CONH--, optionally substituted benzimidazolyl, or an optionally substituted tricyclic radical, and their metal and acid addition salts.
    Type: Grant
    Filed: August 4, 1978
    Date of Patent: June 24, 1980
    Assignee: Laboratoire L. Lafon
    Inventor: Louis Lafon
  • Patent number: 4191537
    Abstract: Fuel compositions for internal combustion engines are provided which contain deposit control additives which maintain cleanliness of intake systems without contributing to combustion chamber deposits. The additives are poly(oxyalkylene) aminocarbamates comprising a hydrocarbyl-terminated poly(oxyalkylene) moiety composed of 2-5 carbon oxyalkylene units.
    Type: Grant
    Filed: June 19, 1978
    Date of Patent: March 4, 1980
    Assignee: Chevron Research Company
    Inventors: Robert A. Lewis, Lewis R. Honnen
  • Patent number: 4185037
    Abstract: The subject of the invention is a process for the manufacture of polycondensation products of hydroxymethylphosphonium compounds and an amine, characterized in that (a) 1 mol of a tetrakis-(hydroxymethyl)-phosphonium compound is condensed with 0.02 to 0.3 mol, preferably 0.02 to 0.25 mol, of an amine at 100.degree. to 150.degree. C., optionally in the presence of an inert organic solvent, if appropriate free hydroxyl groups are at least partially etherified with at least one alkanol with 1 to 4 carbon atoms and if appropriate the salts of the polycondensation products are converted into the corresponding hydroxides.The condensation products are used for flameproofing organic fiber material, especially textiles.
    Type: Grant
    Filed: November 24, 1978
    Date of Patent: January 22, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann Nachbur, Arthur Maeder
  • Patent number: 4183933
    Abstract: 2,3,4,7,8,9-Substituted octahydropyrazinopyrimidinones and acid addition salts thereof. A process for the preparation of said compounds. A pharmaceutical composition comprising such a compound and a conventional carrier. A process for the preparation of said composition. Method of medical treatment of human beings and animals using such compounds.
    Type: Grant
    Filed: August 30, 1978
    Date of Patent: January 15, 1980
    Assignee: AB Ferrosan
    Inventors: Anders K. K. Bjork, Aina L. Abramo, Sven E. H. Hernestam, Bengt E. S. Kjellberg
  • Patent number: 4172707
    Abstract: Mannich condensation products useful in gasoline as carburetor detergents; the condensation compositions having the formula ##STR1## wherein Z is an alkyl- and hydroxy-substituted benzyl group wherein the alkyl has 20 to 1000 carbon atoms; n is 2; x, y, and c are each 0 or 1; x+y=0 or 1; with the proviso that when x is 0 and y is 0, then c is 0; when x is 1 and y is 0, then c is 1 and when x is 0 and y is 1, then c is 1.
    Type: Grant
    Filed: July 20, 1978
    Date of Patent: October 30, 1979
    Assignee: E. I. Du Pont de Nemours & Company
    Inventor: Bruce H. Garth
  • Patent number: 4172094
    Abstract: Novel diphenyl and loweralkyl substituted diphenyl polyamines are useful antimicrobial agents, as well as algae inhibitors. They are especially useful because of their low toxicity, and as such are advantageously included as the active agent in surgical scrubs, antibacterial soaps, as preservatives in cosmetic preparations, and the like. They also can be used for topical treatment of dermatological conditions having a bacterial origin or implication such as Acne vulgaris.
    Type: Grant
    Filed: December 3, 1976
    Date of Patent: October 23, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Richard A. Dybas, Nathaniel Grier, Bruce E. Witzel
  • Patent number: 4160648
    Abstract: Fuel compositions for internal combustion engines are provided which contain deposit control additives which maintain cleanliness of intake systems without contributing to combustion chamber deposits. The additives are polyloxyalkylene carbamates comprising a hydroxy- or hydrocarbyloxy-terminated polyloxyalkylene chain of 2-5 carbon oxyalkylene units bonded through an oxycarbonyl group to a nitrogen atom of a polyamine having from 2 to 10 amine nitrogens and from 2 to 40 carbons with a carbon:nitrogen ratio between about 1:1 and 10:1.
    Type: Grant
    Filed: May 27, 1977
    Date of Patent: July 10, 1979
    Assignee: Chevron Research Company
    Inventors: Robert A. Lewis, Lewis R. Honnen
  • 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: 4152459
    Abstract: Cis- and trans-N-(2-aminocycloaliphatic)benzamide compounds of the formula ##STR1## e.g., N-methyl-N-[2-(N-pyrrolidinyl)cyclohexyl]-3,4-dichlorobenzamide, and their parmaceutically acceptable salts, have been found to have potent analgesic activity, and compositions containing these compounds useful in pharmaceutical dosage unit form for alleviating pain in warm blooded animals, as well as methods for alleviating pain in animals with these compositions. Processes for preparing the compounds are also disclosed.
    Type: Grant
    Filed: May 10, 1978
    Date of Patent: May 1, 1979
    Assignee: The Upjohn Company
    Inventor: Jacob Szmuszkovicz
  • Patent number: 4148897
    Abstract: Novel 1,2-dihydronaphthalene derivatives of the formula ##STR1## wherein R.sup.1 and R.sup.2, independently of each other, are hydrogen, nitro, amino, halogen, or hydroxyl which may be protected, and R.sup.3 is a piperazinyl or morpholino group which may be substituted by lower alkyl, aralkyl, carboxylic acid-derived acyl, lower alkoxycarbonyl-lower alkyl or cycloaminocarbonyl-lower alkyl, and its salts have excellent pharmacological activities such as vasodilator and cerebral blood flow increasing activities.
    Type: Grant
    Filed: April 20, 1977
    Date of Patent: April 10, 1979
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshikazu Oka, Katsumi Itoh, Akio Miyake, Minoru Hirata
  • Patent number: 4145435
    Abstract: Cis- and trans-N-(2-aminocycloaliphatic)-2-arylacetamide derivative compounds of the formula ##STR1## e.g., N-?2-(N', N'-dimethylamino)cyclohexyl!-N-methyl-2-(4-bromophenyl)acetamide and trans-N-methyl-N-?2-(1-pyrrolidinyl)cyclohexyl!acetamide, 2-(3,4-dichlorophenyl) and their pharmaceutically acceptable salts, have been found to have potent analgesic activity, and the preferred compounds have in addition only low to moderate apparent physical dependence liability, compared to morphine and methadone. As analgesics they would be useful also as antitussives. Processes for preparation of these compounds are also disclosed. This invention also includes compositions containing these compounds useful in pharmaceutical dosage unit form for alleviating pain in humans and animals, as well as methods for alleviating pain in animals and humans with these compositions.
    Type: Grant
    Filed: November 12, 1976
    Date of Patent: March 20, 1979
    Assignee: The Upjohn Company
    Inventor: Jacob Szmuszkovicz
  • Patent number: 4134889
    Abstract: Manufacture of glycinonitriles by reacting amines with carbonyl compounds and hydrogen cyanide under specific reaction conditions in respect of the temperature, reaction time and hydrogen cyanide concentration.The glycinonitriles obtainable by the process of the invention are antioxidants and valuable starting materials for the manufacture of dyes, fungicides, bactericides, textile auxiliaries and inhibitors for use in antifreezes.
    Type: Grant
    Filed: May 2, 1977
    Date of Patent: January 16, 1979
    Assignee: BASF Aktiengesellschaft
    Inventors: Harry Distler, Erwin Hartert, Helmut Schlecht
  • 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: 4121911
    Abstract: Mannich condensation products useful in gasoline as carburetor detergents; the condensation compositions having the formula ##STR1## wherein Z is an alkyl - and hydroxy - substituted benzyl group wherein the alkyl has 20 to 1000 carbon atoms, n is 2 or 3; R is an alkyl of 1 to 20 carbon atoms; a, x and c are each 0 or 1; and b is 0 to 5; with the provisos that when a = 0, then b is at least 1 and c = 1; when a = 1 and x = 0, then b and c = 0; and when a = 1 and x = 1, then c = 1.
    Type: Grant
    Filed: June 6, 1977
    Date of Patent: October 24, 1978
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Bruce Hollis Garth
  • Patent number: 4110328
    Abstract: Antimicrobial compounds are disclosed having the formula:Z--B--Y--B--Z .rHAwherein B is carbamylguanidino or thiocarbamylguanidino, Y is a nitrogen-containing alkylene group having the structural formula: ##STR1## WHEREIN: N = 2-4m = 2-4p = 1,2q = 2-4x = 0-3y = 0-2x = 0 when y .noteq. 0 and y = 0 when x .noteq. 0,And R is hydrogen or a C.sub.1 -C.sub.8 hydrocarbon radical selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, and aralkyl radicals, R' and R" are each hydrogen or C.sub.1 -C.sub.4 alkyl and may be the same or different and Z is selected from the group consisting of C.sub.1 -C.sub.12 alkyl, di(C.sub.1 -C.sub.10 alkylamino)-C.sub.10 -C.sub.2 having a total carbon content of C.sub.4 -C.sub.12 ; C.sub.3 -C.sub.12 alkenyl; C.sub.3 -C.sub.12 alkynyl; C.sub.3 -C.sub.12 cycloalkyl, C.sub.4 -C.sub.12 cycloalkylalkyl; C.sub.6 -C.sub.12 cycloalkenyl, C.sub.7 -C.sub.14 cycloalkenylalkyl, C.sub.7 -C.sub.12 polycycloalkyl, C.sub.8 -C.sub.14 polycycloalkylalkyl, C.sub.7 -C.sub.
    Type: Grant
    Filed: October 26, 1976
    Date of Patent: August 29, 1978
    Assignee: Cooper Laboratories, Inc.
    Inventor: Julius Diamond
  • Patent number: 4105664
    Abstract: Dibenz[b,f]oxepins of the formula ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as hereinafter described. The foregoing compounds exhibit strong central depressant and neuroleptic properties, and are useful, for example, in the treatment of acute or chronic schizophrenia and also as tranquilizers.
    Type: Grant
    Filed: March 18, 1977
    Date of Patent: August 8, 1978
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Max Gerecke, Emilio Kyburz, Jean-Pierre Kaplan
  • Patent number: 4103087
    Abstract: An improved process is disclosed for selectively producing a di-(N,N-disubstituted amino) alkane compound which includes contacting an (N,N-disubstituted) amino alkanol compound with an (N,N-disubstituted) amine compound in the presence of a catalytically effective amount of an aluminum phosphate catalyst at a temperature of from about 240.degree. C to 320.degree. C under a pressure sufficient to maintain the mixture substantially in liquid phase and recovering from the resultant reaction mixture the di-(N,N-disubstituted amino) alkane compound.According to a preferred embodiment, N-(2-hydroxyethyl) morpholine is contacted with morpholine in the presence of a catalytically effective amount of a heterogeneous aluminum phosphate catalyst at temperatures of from about 260.degree. C to about 300.degree. C in liquid phase to selectively produce the corresponding N,N'-dimorpholino ethane (DMORE).
    Type: Grant
    Filed: April 1, 1977
    Date of Patent: July 25, 1978
    Assignee: Texaco Development Corporation
    Inventor: Michael E. Brennan
  • Patent number: 4101659
    Abstract: Benzhydryl derivatives of guanidine (Formula I) having blood sugar lowering activity; pharmaceutical hypoglycemic compositions thereof and methods of administering same to hyperglycemic individuals.
    Type: Grant
    Filed: August 29, 1977
    Date of Patent: July 18, 1978
    Assignee: McNeil Laboratories, Incorporated
    Inventor: Chris Royce Rasmussen
  • Patent number: 4101671
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or aliphatic or aromatic carboxylic acyl,R.sub.2 is hydrogen, chlorine or bromine,R.sub.3 is fluorine, alkyl of 1 to 4 carbon atoms, trifluoromethyl, cyano, carbamoyl, carboxyl, carbalkoxy, alkoxy, acetyl, 1-hydroxyethyl or ##STR2## where R.sub.6 and R.sub.7 are each alkyl, cycloalkyl, hydroxy-cycloalkyl or, together with each other and the nitrogen atom to which they are attached, pyrrolidino, piperidino or morpholino, andR.sub.4 and R.sub.5 are each hydrogen, alkyl of 1 to 5 carbon atoms, mono- or di-hydroxy (alkyl of 1 to 5 carbon atoms), alkenyl of 2 to 4 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, mono- or di-hydroxy (cycloalkyl of 5 to 7 carbon atoms), benzyl, morpholinocarbonylmethyl or, together with each other and the nitrogen atom to which they are attached, pyrrolidino, piperidino, hexamethyleneimino, morpholino, N-methyl-piperazino or camphidino,Provided, however, that when R.sub.3 is carboxyl or carbalkoxy, R.sub.4 and R.sub.
    Type: Grant
    Filed: March 24, 1977
    Date of Patent: July 18, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Johannes Keck, Klaus-Reinhold Noll, Helmut Pieper, Gerd Kruger, Sigfrid Puschmann
  • Patent number: 4098791
    Abstract: An improved multistep process for the production of intermediates for hypotensive compounds, which intermediates are of the formula V: ##STR1## wherein R.sub.1 and R.sub.2 are lower alkyl of 1 to 4 carbon atoms, inclusive, alkenyl of 3 or 4 carbon atoms, cycloalkyl from 3 to 7 carbon atoms, phenylalkyl in which the alkyl group is defined as above, or the group ##STR2## is a heterocyclic moiety of 4 to 8 ring members, e.g., azetidinyl, piperidino, pyrrolidinyl, hexahydroazepinyl, or heptamethyleneimino, each of which can be substituted by one or two methyl groups, N-alkylpiperazino, wherein alkyl is defined as above, morpholino, or thiomorpholino, and wherein R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms, inclusive, starts with the corresponding secondary amine I ##STR3## wherein R.sub.1 and R.sub.2 have the significance of above.
    Type: Grant
    Filed: July 29, 1977
    Date of Patent: July 4, 1978
    Assignee: The Upjohn Company
    Inventors: Thomas A. Hylton, Muniraj D. Pillai
  • Patent number: 4098904
    Abstract: Cis- and trans-N-(2-aminocycloaliphatic)benzamide compounds of the formula ##STR1## E.G., N-methyl-N[2-(N-pyrrolidinyl)cyclohexyl[3,4-dichlorobenzamide, and their pharmaceutically acceptable salts, have been found to have potent analgesic activity, and compositions containing these compounds useful in pharmaceutical dosage unit form for alleviating pain in warm blooded animals, as well as methods for alleviating pain in animals with these compositions. Processes for preparing the compounds are also disclosed.
    Type: Grant
    Filed: November 12, 1976
    Date of Patent: July 4, 1978
    Assignee: The Upjohn Company
    Inventor: Jacob Szmuszkovicz
  • Patent number: 4091220
    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 track fluid secretion stimulators.
    Type: Grant
    Filed: May 3, 1977
    Date of Patent: May 23, 1978
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Toshihiro Ishiguro, Yasushi Sanno
  • Patent number: RE29628
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or aliphatic or aromatic carboxylic acyl,R.sub.2 is hydrogen, chlorine or bromine,R.sub.3 is fluorine, alkyl of 1 to 4 carbon atoms, trifluoromethyl, cyano, carbamoyl, carboxyl, carbalkoxy, alkoxy, acetyl, 1-hydroxyethyl or ##STR2## where R.sub.6 and R.sub.7 are each alkyl, cycloalkyl, hydroxy-cycloalkyl or, together with each other and the nitrogen atom to which they are attached, pyrrolidino, piperidino or morpholino, andR.sub.4 and R.sub.
    Type: Grant
    Filed: December 2, 1976
    Date of Patent: May 9, 1978
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Johannes Keck, Klaus-Reinhold Noll, Helmut Pieper, Gerd Kruger, Sigfrid Puschmann