Nitrogen Attached Indirectly To The Piperazine Ring By Nonionic Bonding Patents (Class 544/402)
  • Patent number: 4668681
    Abstract: This invention relates to 2-(4-phenylpiperazinylethyl)anilines, to methods for preparing them and to their uses in medical therapy.These compounds have the following general formula ##STR1## wherein R.sub.1 represents one or more substituents selected from the group consisting of H, CH.sub.3, CF.sub.3, F, Cl, and OCH.sub.3 ; R.sub.2 and R.sub.3, which may be the same or different, and are selected from the group consisting of H and (C.sub.1 -C.sub.4) alkoxy, or R.sub.2 and R.sub.3 taken together can form a chain selected from the group consisting of --O-- (CH.sub.2).sub.n --O--, wherein n=1 or 2 and --O--CH.sub.2 --O--CH.sub.2 with the proviso that R.sub.1 is not meta CF.sub.3 when R.sub.2 =R.sub.3 =H, and pharmaceutically non-toxic salts thereof. The compounds of this invention are useful in the treatment of allergic and anaphylatic conditions and motion sickness.
    Type: Grant
    Filed: March 21, 1986
    Date of Patent: May 26, 1987
    Assignee: Societe Cortial, S.A.
    Inventors: Henri Pontagnier, Marie-H/e/ l/e/ ne Creuzet, Claude Feniou, Francoise Guichard, Gis/e/ le Prat
  • Patent number: 4656180
    Abstract: Diamine derivatives corresponding to the general formula IR.sup.1 R.sup.2 N--(CH.sub.2).sub.m --Q--A--NH--R--NH--B--Q'--(CH.sub.2).sub.n NR.sup.3 R.sup.4 (I)which have a highly selective action on histamine-H.sub.2 receptors and are therefore suitable for use as anti-ulcerative agents are described. Processes for the preparation of these compounds and pharmaceutical preparations containing these compounds are also described.
    Type: Grant
    Filed: March 5, 1985
    Date of Patent: April 7, 1987
    Assignee: Ludwig Heumann & Co., GmbH
    Inventors: Stefan Postius, Rolf Herter, Peter Morsdorf, Helmut Schickaneder, Istvan Szelenyi, Kurt H. Ahrens
  • Patent number: 4650906
    Abstract: Ethyleneamines are recovered from an aqueous solution of carbonates of ethyleneamines by distilling an aqueous solution of carbonates of ethyleneamines including ethylenediamine, in which the molar ratio of the carbon dioxide component to the ethyleneamines including ethylenediamine is 0.01 to 0.5, whereby ethylenediamine is distilled out together with water. The aqueous solution to be distilled is advantageously prepared by heating an aqueous solution of carbonates of ethyleneamines including ethylenediamine to effect decarboxylation.
    Type: Grant
    Filed: February 29, 1984
    Date of Patent: March 17, 1987
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Tsugio Murakami, Taizo Kawamoto
  • Patent number: 4645862
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.3 each is benzyl or substituted with up to 3 methoxy groups, R.sub.2 is a hydrogen atom and (alkylene) is lower alkyl and the compounds are useful for controlling viral infections.
    Type: Grant
    Filed: April 15, 1985
    Date of Patent: February 24, 1987
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Yoshiyuki Tahara, Yasuhiro Komatsu, Hiroyasu Koyama, Reiko Kubota, Teruhito Yamaguchi, Toshihiro Takahashi
  • Patent number: 4645837
    Abstract: In the transalkylation of tertiary amines, unexpected higher yields are achieved requiring substantially less catalyst and much shorter reaction times at lower reaction temperatures using a homogeneous catalyst in the presence of an alcohol solvent and carbon monoxide. The process may be exemplified by reacting triethylamine and tripropylamine in the presence of a homogeneous triosmiumdodecacarbonyl catalyst, ethanol, and carbon monoxide to prepare diethylpropylamine and ethyldipropylamine.
    Type: Grant
    Filed: November 5, 1984
    Date of Patent: February 24, 1987
    Assignee: SRI International
    Inventors: Richard M. Laine, Youval Shvo
  • Patent number: 4638003
    Abstract: N-substituted derivatives of 1-(4'-alkylthiophenyl)-2-amino-1,3-propanediol, their salts with pharmaceutically acceptable organic and inorganic acids, processes for preparing them, pharmaceutical compositions containing them and intermediates useful in the preparation thereof.The novel derivatives according to this invention are endowed with calcium antagonist activity and are useful as antiarrhythmic and vasodilating agents.
    Type: Grant
    Filed: August 1, 1984
    Date of Patent: January 20, 1987
    Assignee: Zambon S.p.A.
    Inventors: Dario Chiarino, Angelo Carenzi, Davide Della Bella, Mario Fantucci
  • Patent number: 4634770
    Abstract: This invention relates to novel isoquinolinesulfonamide derivatives of Formula (I): ##STR1## wherein A is a C.sub.0-10 alkylene group or a C.sub.0-10 alkylene group having a C.sub.1-10 alkyl group, a phenyl group, a substituted phenyl group or a phenylalkyl group; R.sub.1 and R.sub.2 each is a hydrogen atom; or R.sub.1 and R.sub.2 are linked directly to form an ethylene group unsubstituted or substituted with a C.sub.1-4 alkyl group;R.sub.3 and R.sub.4 each is a hydrogen atom, a C.sub.1-6 alkyl group or linked directly to form a C.sub.2-6 alkylene group; and the pharmaceutically acceptable acid addition salt thereof, and to a process for preparing them. The isoquinoline derivatives possess a relaxatory action for vascular smooth muscle and action for increasing blood flow and are useful as a vasodilator and a hypotensor.
    Type: Grant
    Filed: November 4, 1983
    Date of Patent: January 6, 1987
    Assignees: Asahi Kasei Kogyo Kabushiki Kaisha, Hiroyoshi Hidaka
    Inventors: Hiroyoshi Hidaka, Takanori Sone
  • Patent number: 4632940
    Abstract: N-substituted derivatives of 1-(4'-alkylsulfonylphenyl)-2-amino-1,3-propanediol, their salts with pharmaceutically acceptable organic and inorganic acids, processes for preparing them, pharmaceutical compositions containing them and intermediates useful in the preparation thereof.The novel derivatives according to this invention are endowed with local anesthetic activity.
    Type: Grant
    Filed: August 3, 1984
    Date of Patent: December 30, 1986
    Assignee: Zambon S.p.A.
    Inventors: Dario Chiarino, Angelo Carenzi, Davide Della Bella, Mario Fantucci
  • Patent number: 4625030
    Abstract: The present invention concerns a potentiated nickel catalyst and its use for the catalytic amination of lower aliphatic alkane derivatives.
    Type: Grant
    Filed: May 23, 1984
    Date of Patent: November 25, 1986
    Assignee: Union Carbide Corporation
    Inventor: Donald C. Best
  • Patent number: 4620006
    Abstract: Novel 1-(cyanoalkyl)-4-guanylpiperazine acid salts are prepared by reacting novel 1-(cyanoalkyl)piperazines with cyanamide in the presence of an acid. The novel 1-(cyanoalkyl)-4-guanylpiperazine acid salts are advantageously employed to prepare 1-(cyanoalkyl)-4-(2-pyrimidyl)piperazines by reacting them with malonaldehyde in an acidic medium.
    Type: Grant
    Filed: August 11, 1982
    Date of Patent: October 28, 1986
    Assignee: Eastman Kodak Company
    Inventors: Louise O. Sandefur, Wojciech Slusarek, Burton D. Wilson, Cataldo A. Maggiulli
  • Patent number: 4620005
    Abstract: Phenyl tetrahydronaphthylcarboxylate of the formula: ##STR1## wherein A is a direct bond, or a lower alkylene, vinylene or imino group; B is a direct bond, a lower alkylene or --NH-lower alkylene group, or an --OCH.sub.2 CO-- residual group; and R is a lower alkyl group, with the proviso that A and B are not direct bonds simultaneously, and A, B and R are not a lower alkylene group, a direct bond and a methyl group, respectively, at the same time, are effectively useful as chymotrypsin inhibitors.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: October 28, 1986
    Assignee: Kowa Co., Ltd.
    Inventors: Setsuro Fujii, Eizou Hattori, Mitsuteru Hirata, Hisashi Kunieda, Koichiro Watanabe, Hiroshi Ishihama
  • Patent number: 4620002
    Abstract: Novel 2-pyrimidyl alkanesulfonates are prepared by reacting a 2-hydroxypyrimidine acid salt with an alkanesulfonyl chloride in the presence of an acid acceptor. The novel 2-pyrimidyl alkanesulfonates are advantageously employed to prepare 1-(cyanoalkyl)-4-(2-pyrimidyl)piperazines by reacting them with a novel 1-(cyanoalkyl)piperazine in the presence of an acid acceptor.
    Type: Grant
    Filed: August 11, 1982
    Date of Patent: October 28, 1986
    Assignee: Eastman Kodak Company
    Inventors: Louise O. Sandefur, Wojciech Slusarek, Burton D. Wilson, Cataldo A. Maggiulli
  • Patent number: 4602091
    Abstract: Piperazine is substantially selectively converted to ethylenediamine and N-aminoethylpiperazine by catalytically reductively aminating piperazine in the presence of added hydrogen, ammonia and (optionally) water under reductive amination conditions selected to provide a piperazine conversion of not more than about 30%.
    Type: Grant
    Filed: January 25, 1984
    Date of Patent: July 22, 1986
    Assignee: Texaco Inc.
    Inventor: Michael E. Brennan
  • Patent number: 4599335
    Abstract: Diamine derivatives of the formula ##STR1## where R.sup.1 is unsubstituted or substituted alkyl, unsubstituted or substituted aryl or aralkyl, bicycloalkyl, alkoxy, acyl or halogen, n is 0, 1, 2 or 3, R.sup.2 is alkyl, alkenyl or alkoxy, A is unsubstituted or substituted alkylene or unsubstituted or substituted cycloalkylene, R.sup.3, R.sup.4 and R.sup.5 are each unsubstituted or substituted alkyl, alkenyl, alkynyl or unsubstituted or substituted benzyl, or R.sup.3 and R.sup.4, together with A and the two nitrogen atoms bonded to A, form an unsubstituted or substituted piperazine or perhydrodiazepine ring, or R.sup.4 and R.sup.5, together with the nitrogen atom, form an unsubstituted or substituted heterocyclic ring, R.sup.6 is alkyl, alkenyl, alkynyl or unsubstituted or substituted aralkyl or aryloxyalkyl, and Z is an anion of an acid, and fungicides containing these compounds.
    Type: Grant
    Filed: July 31, 1985
    Date of Patent: July 8, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Ernst Buschmann, Norbert Meyer, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4594195
    Abstract: Compounds of formula (I) ##STR1## and acid addition salts thereof, wherein R.sup.1 is hydrogen, hydroxy, alkoxy, aryloxy, aralkoxy, heteroaryloxy or heteroaralkoxy; andone of R.sup.2, R.sup.3 and R.sup.4 is hydrogen and the others are the same or different and each is hydrogen, alkyl, aryl, aralkyl, heteroaryl or heteroaralkyl; orR.sup.2 is hydrogen and ##STR2## is mono- or bi-cyclic amino, inhibit enterotoxin-induced secretion into the small intestine and are, therefore, useful in treating enterotoxin induced diarrhoea in humans and scours in animals.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: June 10, 1986
    Assignee: Beecham Group p.l.c.
    Inventors: Peter M. Newsome, Noel A. Mullan, John P. Marshall
  • Patent number: 4585796
    Abstract: The tertiary amines of the formula ##STR1## wherein n represents a whole number of 1 to 5;X.sup.1 represents phenyl or phenyl mono-, di- or tri-substituted by R.sup.1, R.sup.2 and R.sup.3 ;X.sup.2 represents hydrogen, lower-alkyl, phenyl or phenyl mono-, di- or tri-substituted by R.sup.1, R.sup.2 and R.sup.3 ;Y represents hydrogen, lower-alkyl, hydroxymethyl, carboxy or lower-alkoxycarbonyl;Z represents a group of the formula ##STR2## R.sup.1, R.sup.2 and R.sup.3 represent hydrogen, halogen, hydroxy, benzyloxy, lower-alkyl, lower-alkoxy, hydroxymethyl, amino, acylamino, lower-alkoxybenzylamino, nitro, carbamoyl, trifluoromethyl or lower-alkylsulphonylmethyl;R.sup.4, R.sup.5 and R.sup.51 represent hydrogen, lower-alkyl, lower-alkoxy, lower alkanoyl, carboxy, cyano, hydroxy, hydroxy-lower-alkyl, acyloxy or a group --C(R.sup.6).dbd.C(R.sup.7)COOR.sup.8, --SO.sub.2 R.sup.9, --C(O)R.sup.9 or --CH.sub.2 R.sup.10, with the proviso that R.sup.4 does not represent hydrogen when R.sup.
    Type: Grant
    Filed: August 1, 1983
    Date of Patent: April 29, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Leo Alig, Marcel Muller
  • Patent number: 4582937
    Abstract: Ethyleneamines are efficiently recovered from an aqueous solution thereof by extracting them from the aqueous solution into an organic phase with an extractant selected from carbonyl group-containing organic solvents, benzyl alcohol, carboxylic acids and salts thereof, alkylphosphoric acids and salts thereof, and mixed solvents containing at least one of these extractants. The ethyleneamines in the organic phase is recovered preferably from the organic phase to the aqueous phase by incorporating an acid therein, followed by phase separation.
    Type: Grant
    Filed: April 12, 1985
    Date of Patent: April 15, 1986
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Yoichi Hiraga, Tsugio Murakami, Hiroyuki Saito, Osamu Fujii
  • Patent number: 4582904
    Abstract: Synthesis of organic amines by condensation of organic hydroxy compound with ammonia or a primary or secondary amine in the presence of a rare earth metal hydrogen phosphate catalyst.
    Type: Grant
    Filed: January 6, 1984
    Date of Patent: April 15, 1986
    Assignee: Air Products and Chemicals, Inc.
    Inventors: James E. Wells, Victoria Eskinazi
  • Patent number: 4578517
    Abstract: A process for preparing polyalkylene polyamine compounds is disclosed wherein ammonia or a primary or secondary amine and an alkanolamine compound are reacted in the presence of an effective amount of a Group IIIB metal acid phosphate at a temperature from about 175.degree. to 400.degree. C. under a pressure sufficient to maintain a substantial amount of the ammonia or amine in the reaction zone. The polyalkylene polyamines thus formed are recovered from the reaction mixture.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: March 25, 1986
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Thomas A. Johnson, Michael E. Ford
  • Patent number: 4567257
    Abstract: Disclosed is a novel class of amidinium salts having the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 when taken individually are independently selected from lower-alkyl, aralkyl and cycloalkyl, and, when taken together with the respective nitrogen atoms to which they are attached, R.sub.1 together with R.sub.2, and R.sub.3 together with R.sub.4 independently represent heterocyclic groups having 5 to 7 ring atoms, R.sub.5, R.sub.6, R.sub.7, and R.sub.8 are independently selected from hydrogen, lower-alkyl, aryl, aralkyl, and cycloalkyl.The amidinium salts are very active catalysts for converting organic isocyanates to products containing isocyanurate and carbodiimide linkages.
    Type: Grant
    Filed: January 16, 1984
    Date of Patent: January 28, 1986
    Assignee: The Upjohn Company
    Inventor: Dale F. Regelman
  • Patent number: 4567174
    Abstract: A bis(1-substituted biguanide) derivative of the formula:R.sup.3 R.sup.4 N.C(:NR.sup.5)NH.C(NR.sup.9)NR.sup.1 --X--NR.sup.2.C(:NR.sup.9)NH.C(:NR.sup.6)--NR.sup.7 R.sup.8 Vor a tautomeric form thereof, wherein R.sup.1, R.sup.2 and R.sup.9, which may be the same or different, are each hydrogen, a 1-16C alkyl radical, a 3-16C cycloalkyl radical, a (3-12C cycloalkyl)-(1-4C alkyl) radical, an optionally substituted phenyl or naphthyl radical, an optionally substituted phenyl(1-4C)alkyl or naphthyl(1-4C)alkyl radical or an optionally substituted diphenylmethyl radical, provided that at least one of R.sup.1, R.sup.2 and R.sup.9 is other than hydrogen; R.sup.3, R.sup.4, R.sup.7 and R.sup.8, which may be the same or different are each hydrogen, or an alkyl, cycloalkyl, (cycloalkyl)alkyl, phenyl, naphthyl, phenylalkyl, naphthylalkyl, or diphenylmethyl radical as defined above, or a 2-16 alkoxyalkyl radical, or R.sup.3, R.sup.4 and the nitrogen atom to which they are attached, or R.sup.7 and R.sup.
    Type: Grant
    Filed: May 7, 1984
    Date of Patent: January 28, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventors: Philip N. Edwards, Michael S. Large
  • Patent number: 4552961
    Abstract: Predominantly linearly extended polyalkylene polyamines are produced, in increased conversion rates, by reacting alkylenediamines with alkylene glycols or alkanolamines using a phosphorus amide catalyst in place of phosphorus acid or acid derivative catalysts.
    Type: Grant
    Filed: May 3, 1984
    Date of Patent: November 12, 1985
    Assignee: Union Carbide Corporation
    Inventor: William B. Herdle
  • Patent number: 4544755
    Abstract: Phthalimides of the formula I ##STR1## where R is a substituent and the ring A can be further substituted, are cleaved by a process in which a compound of the formula I is treated with an alkanolamine.The compounds prepared according to the invention are useful intermediates for the preparation of dyes, drugs and plastics.
    Type: Grant
    Filed: May 23, 1984
    Date of Patent: October 1, 1985
    Assignee: Basf Aktiengesellschaft
    Inventors: Helmut Hagen, Rolf-Dieter Kohler
  • Patent number: 4540523
    Abstract: Cationic styryl dyestuffs of the formula ##STR1## in which A.sup.1 is an alkyleneoxy or alkyleneamino radical,D.sup.1 is a direct bond or divalent radical,An is an anion, andthe terminal phenyl ring is unsubstituted or substituted by CN, alkyl or alkoxy. The compounds are suitable for dyeing, enscribing and printing paper for dyeing and printing synthetic fibres, especially made of polyacrylonitrile, acid-modified polyesters or polyamides.
    Type: Grant
    Filed: October 17, 1980
    Date of Patent: September 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hermann Beecken
  • Patent number: 4539319
    Abstract: Compounds of formula (I) ##STR1## and acid addition salts thereof, whereinR.sup.1 is hydrogen, hydroxy, alkoxy, aryloxy, aralkoxy, heteroaryloxy or heteroaralkoxy;andone of R.sup.2, R.sup.3 and R.sup.4 is hydrogen and the others are the same or different and each is hydrogen, alkyl, aryl, aralkyl, heteroaryl or heteroaralkyl;orR.sup.2 is hydrogen and ##STR2## is mono- or bi-cyclic amino, inhibit enterotoxin-induced secretion into the small intestine and are, therefore, useful in treating enterotoxin induced diarrhoea in humans and scours in animals.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: September 3, 1985
    Assignee: Beecham Group p.l.c.
    Inventors: Peter M. Newsome, Noel A. Mullan, John P. Marshall
  • Patent number: 4517366
    Abstract: Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.
    Type: Grant
    Filed: April 16, 1984
    Date of Patent: May 14, 1985
    Assignee: Bristol-Myers Company
    Inventors: Ronnie R. Crenshaw, Aldo A. Algieri
  • Patent number: 4515947
    Abstract: Novel cyanoalkylpiperazines are prepared by reacting piperazine with a haloalkylnitrile in the presence of an acid acceptor. The novel cyanoalkylpiperazines are advantageously employed to prepare 1-(cyanoalkyl)-4-(2-pyrimidyl)piperazines by reacting them with halopyrimidines in the presence of an acid acceptor.
    Type: Grant
    Filed: August 11, 1982
    Date of Patent: May 7, 1985
    Assignee: Eastman Kodak Company
    Inventors: Louise O. Sandefur, Wojciech Slusarek, Burton D. Wilson, Cataldo A. Maggiulli
  • Patent number: 4507318
    Abstract: The present invention concerns new derivatives of 1-aryl 2-aminomethyl cyclopropane carboxylates (Z), their preparation and their use as useful drugs for the treatment of various pains.The new derivatives of the present invention have the general formula I ##STR1## in which: R represents a hydrogen or halogen atom, a C.sub.1 to C.sub.4 lower alkyl group, a C.sub.1 to C.sub.4 lower alkoxy group, or a nitro, amino, sulfamoyl or hydroxy group;n represents the values 1, 2 or 3;(R).sub.n may together with the benzene ring also form the naphthyl group;R.sub.1 represents a linear or branched C.sub.1 to C.sub.5 alkyl or alkenyl group or an aryl or benzyl group;R.sub.2 and R.sub.3 represent a hydrogen atom, a linear or branched C.sub.1 to C.sub.5 alkyl, alkenyl, alkynyl, hydroxyalkyl, alkoxyalkyl, carboxyalkyl or dialkylaminoalkyl group or an aryl, arylalkyl or cycloalkyl group;R.sub.2 and R.sub.3 possibly also forming a heterocycle of 5 or 6 members with the adjacent nitrogen atom,provided however that when R.sub.
    Type: Grant
    Filed: June 22, 1982
    Date of Patent: March 26, 1985
    Assignee: Pierre Fabre S.A.
    Inventors: Henri Cousse, Gilbert Mouzin, Bernard Bonnaud, Marie Charveron, Francois Fauran
  • Patent number: 4487987
    Abstract: A method of eliminating color-causing impurities in mixtures of aminoethylpiperazine, polyoxypropylenediamines and alkylphenols by treatment with N,N-diethylhydroxylamine is described. These alkylphenols such as nonylphenol are used in epoxy resins in the automotive and electronics industry. Discoloration of the phenol and subsequent resin occurs if the phenol is not treated with N,N-diethylhydroxylamine. Quantities on the order of 20 to 500 ppm are effective. The decolorization reaction may be conducted at a temperature in the range from about 25.degree. to 50.degree. C.
    Type: Grant
    Filed: June 9, 1983
    Date of Patent: December 11, 1984
    Assignee: Texaco Inc.
    Inventors: James H. Paslean, Charles S. Steele
  • Patent number: 4469693
    Abstract: 2-(4-Substituted alkyl-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: 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: 4446076
    Abstract: Method of preparing antimicrobial compounds of the formula: ##STR1## comprising the following steps: (1) halogenating allyl halide to form 1,2,3-trihalopropane; (2) dehydrohalogenating the 1,2,3-trihalopropane to form 2,3-dihalo-1-propene;(3) treating the 2,3-dihalo-1-propene with a Grignard reagent of the formula R--MgHal, where R is as defined above, followed by treatment with magnesium, to form 3-(R-substituted)-2-magnesiumhalide)-1-propene;(4) treating the 3-(R-substituted)-2-(magnesiumhalide)-1-propene with cyanogen to form 3-(R-substituted)-2-cyano-1-propene; and(5) brominating the 3-(R-substituted)-2-cyano-1-propene to form the desired product.
    Type: Grant
    Filed: December 22, 1981
    Date of Patent: May 1, 1984
    Assignee: Merck & Co., Inc.
    Inventor: Marshall R. Angeles
  • Patent number: 4442122
    Abstract: Antimicrobial compounds of the formula: ##STR1## where R is C.sub.3-12 alkyl, straight or branched chain C.sub.3 -C.sub.8 cycloalkyl; C.sub.3-8 cycloalkylC.sub.1-3 alkyl; or saturated heterocyclic radical selected from the group consisting of pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, isoxazolidinyl, oxazolidinyl, isothiazolidinyl, pyrazolidinyl, imidazolidinyl, piperazinyl, and piperidinyl.
    Type: Grant
    Filed: December 22, 1981
    Date of Patent: April 10, 1984
    Assignee: Merck & Co., Inc.
    Inventors: John E. Engelhart, Marshall R. Angeles, Michael J. D'Errico
  • Patent number: 4436908
    Abstract: Compounds of the formula (I):R.sub.2 N--(CH.sub.2).sub.n --NH--SO.sub.2 R.sup.1 (I)and salts thereof wherein NR.sub.2 represents a piperidyl, pyrrolidyl, or N-methylpiperazyl group any of which may be substituted by one or two methyl groups; R.sup.1 is a 1-naphthyl group substituted by one or two moieties selected from fluorine, chlorine, bromine, methoxyl, ethoxyl, hydroxyl, acetoxyl, nitro, cyano, amino optionally substituted by one or two C.sub.1-6 alkyl groups, methyl, ethyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, acetamido or carboxamido; and n is 2 or 3, pharmaceutical compositions containing them and a process for their preparation.
    Type: Grant
    Filed: March 12, 1982
    Date of Patent: March 13, 1984
    Assignee: Johann A. Wuelfing
    Inventor: Ljerka Jozic
  • Patent number: 4429127
    Abstract: This invention relates to a new compound of value as antibacterial agent. More particularly, it relates to a quinoline carboxylic acid derivative and the acid addition salts thereof.
    Type: Grant
    Filed: February 17, 1982
    Date of Patent: January 31, 1984
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Tsutomu Irikura, Hiroshi Koga, Akira Ito
  • Patent number: 4426521
    Abstract: Novel cyanoguanidine derivatives, and acid addition salts thereof useful as medicines which have pharmacological actions such as anti-secretory effect, local anesthesia action and the like; and process for the preparation thereof.
    Type: Grant
    Filed: January 28, 1982
    Date of Patent: January 17, 1984
    Assignee: Eisai Co., Ltd.
    Inventors: Satoru Tanaka, Katsutoshi Shimada, Kazunori Hashimoto, Kiichi Ema, Koichiro Ueda
  • Patent number: 4419363
    Abstract: Novel 1-aryloxy-3-amidoamidoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. Representative of the compounds disclosed is 1-(o-cyanophenoxy)-3-.beta.-(2-thenamidoacetamido)ethylaminopropan-2-ol.
    Type: Grant
    Filed: June 4, 1982
    Date of Patent: December 6, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventor: Leslie H. Smith
  • Patent number: 4418209
    Abstract: This invention describes a new class of 1-amidino-3-phenylthiourea and N'-phenylamidinothiourea compounds wherein the phenyl group is ortho substituted, and processes for their preparation. The phenylamidinothiourea compounds may be incorporated into pharmaceutical preparations which are useful for producing anti-ulcerogenic, antisecretory, antispasmodic, antihypertensive, anti-arrhythmic, anesthetic, antidiarrheal and antiparasitic action.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: November 29, 1983
    Assignee: William H. Rorer, Inc.
    Inventors: George H. Douglas, Julius Diamond, William L. Studt, Stuart A. Dodson
  • Patent number: 4411904
    Abstract: Compounds of the formula ##STR1## where X and Y are hydrogen, halogen, lower alkyl, nitro are useful as neuroleptics.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: October 25, 1983
    Assignee: Warner-Lambert Company
    Inventor: Ian C. Pattison
  • Patent number: 4374779
    Abstract: The disclosed [[2-(substituted amino)-2-phenylethyl]nitrosoamino]acetonitrile derivatives and the ring closed oxadiazolium salts thereof as well as their pharmaceutically acceptable acid addition salts are antihypertensive agents useful in the treatment of hypertension.
    Type: Grant
    Filed: November 16, 1981
    Date of Patent: February 22, 1983
    Assignee: American Home Products Corporation
    Inventor: Reinhardt P. Stein
  • Patent number: 4369206
    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: July 2, 1979
    Date of Patent: January 18, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wofram Mayer, Hans Rudolph, Eckhard de Cleur, Manfred Schonfelder
  • Patent number: 4364954
    Abstract: Compounds of the formula ##STR1## where X and Y are hydrogen, halogen, lower alkyl, nitro are useful as neuroleptics.
    Type: Grant
    Filed: May 29, 1981
    Date of Patent: December 21, 1982
    Assignee: Warner-Lambert Company
    Inventor: Ian C. Pattison
  • Patent number: 4340756
    Abstract: Novel halophenyl and loweralkyl substituted halophenyl 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.
    Type: Grant
    Filed: February 4, 1981
    Date of Patent: July 20, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Richard A. Dybas, Nathaniel Grier, Bruce E. Witzel
  • Patent number: 4333929
    Abstract: A compound of formula (II) or a pharmaceutically acceptable acid addition salt thereof ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and each represents C.sub.1-6 alkyl; R.sup.5 represents hydrogen or C.sub.1-6 alkyl; R.sup.6 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.5 and R.sup.6 together represent the remaining members of a 5- or 6-membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl, carboxy or C.sub.1-6 alkoxycarbonyl; and R.sup.7 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.
    Type: Grant
    Filed: January 19, 1981
    Date of Patent: June 8, 1982
    Assignee: Beecham Group Limited
    Inventor: Barrie C. C. Cantello
  • Patent number: 4334085
    Abstract: A transamination process for producing Mannich products comprising reacting a polyamine with a substantially formaldehyde-free mononitrogen Mannich adduct.
    Type: Grant
    Filed: September 14, 1978
    Date of Patent: June 8, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventors: Robert J. Basalay, John H. Udelhofen
  • Patent number: 4329240
    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: January 5, 1981
    Date of Patent: May 11, 1982
    Assignee: Chevron Research Company
    Inventor: Jennifer E. Lilburn
  • 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: 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