Amino Nitrogen Attached To Aryl Ring Or Ring System By An Acyclic Carbon Or Chain Patents (Class 564/336)
  • Patent number: 5231183
    Abstract: A process for producing an enyne derivative, and intermediate, which is useful for preparing compounds showing strong inhibiting activities against squalane.epoxidase of Eumycetes and strong anti-cholesterol activities. The process comprises reacting a compound of the formula:Z--CH.sub.2 --CH.dbd.CH--W [I]wherein W is a halogen atom, and Z is a leaving group, with an amine in the presence of a base, if necessary, to obtain a compound of the formula: ##STR1## then reacting an acetylene derivative to this compound in the presence of a palladium catalyst, to obtain a compound of the formula: ##STR2## and, if necessary, N-alkylating this compound.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: July 27, 1993
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • Patent number: 5225436
    Abstract: Certain aryl substituted naphthalene, benzoxepine, benzazepine and henzocycloheptene derivatives are disclosed. The compounds are useful in treating hyperproliferative skin disease, allergic reactions and inflammation.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: July 6, 1993
    Assignee: Schering Corporation
    Inventors: Neng-Yang Shih, Pietro Mangiaracina, Michael J. Green, Ashit K. Ganguly
  • Patent number: 5214129
    Abstract: A renin inhibiting compound of the formula: ##STR1## wherein A is a substituent; W is C.dbd.O or CHOH; U is CH.sub.2 or NR.sub.2, provided that when W is CHOH then U is CH.sub.2 ; R.sub.1 is loweralkyl, cycloalkylmethyl, benzyl, 4-methoxybenzyl, halobenzyl, (1-naphthyl)methyl, (2-naphthyl)methyl, (4-imidazoyl)methyl, .alpha.,.alpha.-dimethylbenzyl, 1-benzyloxyethyl, phenethyl, phenoxy, thiophenoxy or anilino; R.sub.2 is hydrogen or loweralkyl; R.sub.3 is loweralkyl, [(alkoxy)alkoxy]alkyl, (thioalkoxy)alkyl, loweralkenyl, benzyl or heterocyclic ring substituted methyl; R.sub.4 is loweralkyl, cycloalkylmethyl or benzyl; R.sub.5 is vinyl, formyl, hydroxymethyl or hydrogen; R.sub.7 is hydrogen or loweralkyl; R.sub.8 and R.sub.9 are independently selected from OH and NH.sub.2 ; and R.sub.6 is hydrogen, loweralkyl, vinyl or arylalkyl; provided that when R.sub.5 and R.sub.7 are both hydrogen and R.sub.8 and R.sub.9 are OH, the carbon bearing R.sub.5 is of the "R" configuration and the carbon bearing R.sub.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: May 25, 1993
    Assignee: Abbott Laboratories
    Inventors: Jay R. Luly, Jacob J. Plattner, Dale J. Kempf
  • Patent number: 5160648
    Abstract: Improved additives/detergents for lubricant and fuel compositions are obtained by condensing a hydroxyalkyl or hydroxyaryl compound with an amine compound. The condensates according to the present invention are produced by the acid catalyzed condensation of the amine reactant with the hydroxy reactant.
    Type: Grant
    Filed: June 13, 1991
    Date of Patent: November 3, 1992
    Assignee: The Lubrizol Corporation
    Inventor: Thomas F. Steckel
  • Patent number: 5141676
    Abstract: Organic-solvent soluble magnesium hydrides of the formulas(MgH.sub.2).sub.n. MgQ.sub.2 (II)(MgH.sub.2).sub.n. RMgX (III) ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamino, aralkyl, aryl or diarylamino group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine,--E D.fwdarw. is a chelating ligand,E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamino, diarylamino or alkoxy group, each with up to 19 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.
    Type: Grant
    Filed: April 17, 1991
    Date of Patent: August 25, 1992
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Borislav Bogdanovic, Manfred Schwickardi
  • Patent number: 5124334
    Abstract: The invention relates to benylalcohol phospholipase A.sub.2 inhibitors, pharmaceutical compositions containing them, and methods of treating phospholipase A.sub.2 -mediated conditions in mammals by administration of a therapeutically effective amount of such a benzylalcohol phospholipase A.sub.2 inhibitor.
    Type: Grant
    Filed: July 28, 1989
    Date of Patent: June 23, 1992
    Assignee: Du Pont Merck Pharmaceutical Company
    Inventor: Wendell W. Wilkerson
  • Patent number: 5091536
    Abstract: Organic-solvent soluble magnesium hydrides of the formulas ##STR1## are prepared by catalytically hydrogenating finely powdered magnesium, optionally in the presence of a magnesium halide, in an organic solvent in the presence of their MgH.sub.2 -free counterparts in whichQ is an alkyl, alkenyl, alkoxy, dialkylamide, aralkyl, aryl or diarylamide group, each with up to 18 carbon atoms,R is an alkenyl, aralkyl or aryl group, each with up to 18 carbon atoms,X is chlorine, bromine, or iodine,--E D.fwdarw. is a chelating ligand,E is --CH.sub.2, --N(R)-- or --O--,is an alkylene radical of the formula --(CH.sub.2).sub.p,D is a dialkylamide, diarylamide or alkoxy group, each with up to 18 carbon atoms,M is aluminum or boron,m is 1, 2, or 3, and1<n.ltoreq.50.
    Type: Grant
    Filed: February 9, 1988
    Date of Patent: February 25, 1992
    Assignee: Studiengesellschaft Kohle mbh
    Inventors: Borislav Bogdanovic, Manfred Schwickardi
  • Patent number: 5091575
    Abstract: A renin inhibiting compound of the formula: ##STR1## wherein A is a substituent; W is C.dbd.O or CHOH; U is CH.sub.2 or NR.sup.2, provided that when W is CHOH then U is CH.sub.2 ; R.sub.1 is loweralkyl, cycloalkylmethyl, benzyl, 4-methoxybenzyl, halobenzyl, (1-naphthyl)methyl, (2-naphthyl)methyl, (4-imidazoyl)methyl, .alpha.,.alpha.-dimethylbenzyl, 1-benzyloxyethyl; phenethyl, phenoxy, thiophenoxy or anilino; R.sub.2 is hydrogen or loweralkyl; R.sub.3 is loweralkyl, [(alkoxy)alkoxy]alkyl, (thioalkoxy)alkyl; lowerakenyl, benzyl or heterocyclic ring substituted methyl; R.sub.4 is loweralkyl, cycloalkylmethyl or benzyl; R.sub.5 is vinyl, formyl, hydroxymethyl or hydrogen; R.sub.7 is hydrogen or loweralkyl; R.sub.8 and R.sub.9 are independently selected from OH and NH.sub.2 ; and R.sub.6 is hydrogen, loweralkyl, vinyl or arylalkyl; provided that when R.sub.5 and R.sub.7 are both hydrogen and R.sub.8 and R.sub.9 are OH, the carbon bearing R.sub.5 is of the "R" configuration and the carbon bearing R.sub.
    Type: Grant
    Filed: June 10, 1991
    Date of Patent: February 25, 1992
    Assignee: Abbott Laboratories
    Inventors: Jay R. Luly, Jacob J. Plattner, Dale J. Kempf
  • Patent number: 5089639
    Abstract: N-Cycloalkylalkylamines of formula I: ##STR1## in which: R1 is phenyl which is optionally mono-, di- or trisubstituted by halogens or lower alkyl, haloalkyl or lower alkoxy radicals, or is an aromatic heterocyclic radical having 5 to 7 chain members, in which the hetero atom is nitrogen, oxygen or sulphur,R2 is lower alkyl,R3 is hydrogen or lower alkyl,m has the value of 1 or 2,R4 is cycloalkyl --CH(CH2)n, in which a carbon atom may carry a radical Rx, which is lower alkyl or phenyl; and in which n has the values from 2 to 5,R5 is phenyl, which can be mono-, di- or trisubstituted by halogens or by lower alkoxy radicals, andQ represents an ethylene-1,2-diyl group --CH.dbd.
    Type: Grant
    Filed: January 24, 1991
    Date of Patent: February 18, 1992
    Assignee: Jouveinal S.A.
    Inventors: Gilbert G. Aubard, Alain P. Calvet, Jean-Pierre Defaux, Claude J. Gouret, Agnes M. Grouhel, Henry L. Jacobelli, Jean-Louis Junien, Xavier B. Pascaud, Francois F. Roman, James P. Hudspeth, Yuan Lin
  • Patent number: 5086074
    Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable salt thereof, wherein R.sup.2 is selected from hydroxy and lower alkoxy, R.sup.5 is lower alkyl, and R.sup.11 and R.sup.12 are independently selected from hydrogen, halo, hydroxy, methoxy, and lower alkyl, are selective .alpha..sub.2 adrenergic receptor antagonists useful in the treatment of glaucoma.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: February 4, 1992
    Assignee: Abbott Laboratories
    Inventors: John F. DeBernardis, Robert E. Zelle, Fatima Z. Basha
  • Patent number: 5068432
    Abstract: A process for producing the optically pure (+)- or (-) isomer of a phenyl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: February 1, 1991
    Date of Patent: November 26, 1991
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5045567
    Abstract: Propanolamine derivatives of the formula ##STR1## wherein R.sup.1 is hydrogen or a group of formula ##STR2## n is the number 0 or 1; R.sup.2 and R.sup.5 are phenyl, m-halophenyl, m-trifluoromethylphenyl, thienyl or pyridyl;R.sup.3 is hydrogen or methyl;R.sup.4 is hydrogen, --CH.sub.2 COOH, --CH.sub.2 COO--C.sub.1-4 -alkyl, --(CH.sub.2).sub.2 O--C.sub.1-4 -alkyl or --(CH.sub.2).sub.2 O(CH.sub.2).sub.1-4 --C.sub.6 H.sub.5 ;and a physiologically compatible salt thereof.The invention also relates to processes for the preparation of these propanolamine derivatives, pharmaceutical preparations and feedstuffs containing them, and methods of using the propanolamine derivatives.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: September 3, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Frank Kienzle
  • Patent number: 5043466
    Abstract: The preparation of compounds having the formula I ##STR1## where R.sup.1 is --CN, --CO--N(CH.sub.3).sub.2 or --CS--N(CH.sub.3).sub.2 and R.sup.2 is hydrogen, methyl or a removable protecting group is carried out by condensing a compound having the formula ##STR2## where M is lithium, sodium, potassium or halomagnesium and R.sup.3 is methyl or a removable protecting group in a solvent comprising 80-100% of one or more hydrocarbons and 0-20% of one or more ethers.The solvent enables less inconvenient reaction temperatures to be used and higher yields to be obtained. Compounds (I) are new per se where R.sup.1 is --CS--N(CH.sub.3).sub.2. Compounds (I) are chemical intermediates for preparing N,N-dimethyl-2-(1-hydroxycyclohexyl)-2-(4-hydroxyphenyl or 4-methoxyphenyl) ethylamine and pharmaceutically acceptable salts thereof. These end products are antidepressants.
    Type: Grant
    Filed: January 26, 1990
    Date of Patent: August 27, 1991
    Assignee: John Wyeth & Bro., Limited
    Inventor: Robin G. Shepard
  • Patent number: 5034419
    Abstract: N-Cycloalkylalkylamines of formula I: ##STR1## in which: R1 is phenyl which is optionally mono-, di- or trisubstituted by halogens or lower alkyl, haloalkyl or lower alkoxy radicals, or is an aromatic heterocyclic radical having 5 to 7 chain members, in which the hetero atom is nitrogen, oxygen or sulphur,R2 is lower alkyl,R3 is hydrogen or lower alkyl,m has the value of 1 or 2,R4 is cycloalkyl --CH(CH2)n, in which a carbon atom may carry a radical Rx, which is lower alkyl or phenyl; and in which n has the values from 2 to 5,R5 is phenyl, which can be mono-, di- or trisubstituted by halogens or by lower alkoxy radicals, andQ represents an ethylene-1,2-diyl group --CH.dbd.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: July 23, 1991
    Assignee: L'Oreal
    Inventors: Gilbert G. Aubard, Alain P. Calvet, Jean-Pierre DeFaux, Claude J. Gouret, Agnes M. Grouhel, Henry L. Jacobelli, Jean-Louis Junien, Xavier Pascaud, Francois F. Roman, James P. Hudspeth, Yuan Lin
  • Patent number: 5026872
    Abstract: Novel aromatic ether ketone diamine compounds and methods for their preparation are disclosed which comprise from about 3 to 8 aromatic rings interspersed with ether and ketone linkages. The novel ether ketone diamine compounds are useful as monomeric starting materials for the preparation of useful intermediates and useful thermoplastic and high temperature resistant polymers. In preferred embodiments, the novel ether ketone diamines are useful as curing agents for epoxy resin compositions and composite materials.
    Type: Grant
    Filed: February 1, 1984
    Date of Patent: June 25, 1991
    Assignee: American Cyanamid
    Inventor: Dalip K. Kohli
  • Patent number: 4990633
    Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
  • Patent number: 4983630
    Abstract: There are provided new 2,2-difluorocyclopropylethane derivatives of general formula I ##STR1## in which A, B and R.sup.1-5 have the meanings given in the description and processes for their preparation. The compounds of the invention can be used as pesticides, especially against insects and mites.
    Type: Grant
    Filed: November 28, 1988
    Date of Patent: January 8, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Peter Wegner, Hartmut Joppien, Gunter Homberger, Arnim Kohn
  • Patent number: 4980354
    Abstract: The invention relates to tetrahydronaphthalene and indane derivatives with the general formula I: ##STR1## wherein R.sup.1 represents zero to four substituents, which may be the same or different and are selected from OH, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and unsubstituted or C.sub.1 -C.sub.4 alkyl substituted amino;R.sup.2 represents C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl and C.sub.1 -C.sub.4 alkynyl which may be substituted by halogen;R.sup.3 and R.sup.4 represent independently H, C.sub.1 -C.sub.4 alkyl or form together with the nitrogen atom a 5- or 6-membered ring;n has the value 0 or 1;ALK is an aliphatic hydrocarbon with 1-8 carbon atoms and their pharmaceutically acceptable salts.These new compounds are typical monoamine reuptake blockers with additional .alpha..sub.2 antagonist activity and show strong anti-depressant activity without being sedative.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: December 25, 1990
    Assignee: Akzo N.V.
    Inventors: James Cairns, Duncan R. Rae
  • Patent number: 4968832
    Abstract: Novel antihypertensive and coronary dilating asymmetric diesters of 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylic acid (or the stereoisomers or pharmaceutically acceptable acid addition salts thereof) have the general formula (I): ##STR1## wherein Ph is phenyl, Ar is 2-nitrophenyl, 3-nitrophenyl, 2,3-dichlorophenyl or benzofurazan-4-yl, A is a straight or branched chain alkylene radical having from 2 to 6 carbon atoms, R is a straight or branched chain alkyl radical having from 1 to 6 carbon atoms, optionally mono-substituted by an alkoxy substituent having from 1 to 6 carbon atoms, R.sub.1 is hydrogen, hydroxy or an alkyl radical having from 1 to 4 carbon atoms, and R.sub.2 is hydrogen or methyl. The subject diesters are facilely prepared from the aldehydes ArCHO and esters of acetoacetic and 3-aminocrotonic acids.
    Type: Grant
    Filed: June 28, 1988
    Date of Patent: November 6, 1990
    Assignee: Recordati S.A., Chemical and Pharmaceutical Company
    Inventors: Giorgio Bianchi, Dante Nardi, Amedeo Leonardo, Gabriel Kraziani
  • Patent number: 4960938
    Abstract: 2-Chlorobenzylamine is prepared from 2-chlorobenzylchloride in a two-step process. In the first step, 2-chlorobenzylchloride is reacted with alkali metal phthalimide, preferably formed in situ from potassium carbonate and phthalimide, to form the novel intermediate 2-chlorobenzylphthalimide. In the second step, the phthalimide ring of the 2-chlorobenzylphthalimide is cleaved to form 2-chlorobenzylamine. The first step is preferably carried out in an unreactive solvent at 60.degree. C. to reflux temperature, for example, for 1 to 10 hours. The solvent is very preferably dimethylformamide which is advantageously recovered and used again as solvent in the conversion of 2-chlorobenzylchloride to 2-chlorobenzylphthalimide. The second step consists essentially, for example, of hydrazinolysis or hydrolysis.
    Type: Grant
    Filed: November 2, 1988
    Date of Patent: October 2, 1990
    Assignee: Occidental Chemical Corporation
    Inventors: Neil J. O'Reilly, Stanley A. Sojka, Henry C. Lin
  • Patent number: 4959366
    Abstract: A series of [N-alkyl-N-(nitro-, alkylsulphonamido, or amino-phenalkyl)amino]-alkyl, alkoxy or alkylthio phenyl derivatives having utility as anti-arrhythmic agents.
    Type: Grant
    Filed: April 29, 1987
    Date of Patent: September 25, 1990
    Assignee: Pfizer Inc.
    Inventors: Peter E. Cross, Geoffrey N. Thomas, John E. Arrowsmith
  • Patent number: 4948794
    Abstract: Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein R.sup.1 is C.sub.1-12 -alkyl, which may optionally be substituted by hydroxy, formyl, carboxy, carboxylic esters, amides or amines, C.sub.3-8 -cycloalkyl, aryl, aralkyl; and wherein R.sup.6 is, hydrogen, halogen, CN, CF.sub.3, NO.sub.2, or OR', wherein R' is C.sub.1-4 -alkyl and R.sup.5, R.sup.7 and R.sup.8 is hydrogen, provided R.sup.6 is not CF.sub.3, OCH.sub.3, NO.sub.2, C.sup.1 or Br when R.sup.1 is CH.sub.3 ; orR.sup.6 and R.sup.7 independently are NO.sub.2, halogen, CN, CF.sub.3, or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.5 and R.sup.8 are each hydrogen; orR.sup.5 and R.sup.6 together form a further fused aromatic ring, which may be substituted with halogen, NO.sub.2, CN, CF.sub.3 or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.7 and R.sup.8 independently are hydrogen, halogen, CN, CF.sub.3, NO.sub.2 or OR', wherein R' is C.sub.1-4 -alkyl; orR.sup.7 and R.sup.
    Type: Grant
    Filed: November 8, 1988
    Date of Patent: August 14, 1990
    Assignee: A/S Ferrosan
    Inventors: Tage Honore, Poul Jacobsen, Flemming E. Nielsen, Lars Naerum
  • Patent number: 4914241
    Abstract: Diamines of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, alkyl, aryl, alkoxy, aralkyl or cycloalkyl and X is a group of the formula(CR.sup.4 R.sup.5).sub.m (II)where R.sup.4 and R.sup.5 have the meanings given above for R.sup.1 and m is from 1 to 12, are prepared by a process in which a diamine of the formula ##STR2## where R.sup.1, R.sup.2 and X are the groups described above, is reacted with an olefin of the formula ##STR3## where R.sup.6 and R.sup.9 are each hydrogen or alkyl which is straight-chain in the .alpha.-position, in the presence of a zeolite as a catalyst.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: April 3, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Hesse, Wolfgang Hoelderich, Matthias Schwarzmann
  • Patent number: 4897425
    Abstract: Cyclohexylamines of the formula ##STR1## where X is a single bond or an alkylene chain, Y is hydrogen or an aryl, cyclohexyl, 4-cyclohexylcyclohexyl, perhydro-1- or 2-naphthyl or piperidyl radical, R.sup.1 and R.sup.2 are hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkenyl or arylalkyl, or R.sup.1 and R.sup.2 together form an alkylene group and, togehter with the N atom, form a ring, and acid addition salts thereof, with the exception of compounds in which X is a single bond, Y is cyclohexyl, R.sup.1 and R.sup.2 are hydrogen or methyl, and the compounds in which X is C.sub.6 -, C.sub.7 - and C.sub.8 -alkyl, Y is hydrogen and R.sup.1 and R.sup.2 together with the N atom whose substituents they are form a 2,6-dimethylmorpholine radical, and fungicides containing such cyclohexylamines.
    Type: Grant
    Filed: November 16, 1987
    Date of Patent: January 30, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Zipperer, Ernst Buschmann, Norbert Goetz, Ulrich Schirmer, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4891424
    Abstract: 4-Aralkyl-2-nitro-2'-hydroxy-3',5'-dialkyl (or cumyl)-azobenzenes are made by coupling the corresponding diazotized 4-aralkyl-o-nitroaniline with the corresponding phenol. These azobenzene intermediates are used to prepare the corresponding 2H-benzotriazole UV absorber stabilizers substituted on the 5-position of the benzo ring by an aralkyl group, preferably alpha,alpha-dimethylbenzyl.
    Type: Grant
    Filed: April 1, 1988
    Date of Patent: January 2, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Roland A. E. Winter
  • Patent number: 4888447
    Abstract: A process is described for selectively preparing alkoxylated tertiary amine compounds, such as aminated ethoxylated amines, at ambient pressure by reacting an oxyalkylated alcohol with a secondary amine in the presence of a reductive amination catalyst at above ambient temperature using, as a reductive amination catalyst, a combination of Raney nickel and molybdenum.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: December 19, 1989
    Assignee: Ethyl Corporation
    Inventor: Kim R. Smith
  • Patent number: 4886883
    Abstract: Novel substituted triazolo[1,5-a]pyrimidine-2-sulfonamides, e.g., 5,7-dimethyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulf onamide and their agriculturally acceptable salt are prepared. These compounds and compositions containing them are useful for the control of unwanted vegetation. Novel substituted triazolo[1,5-a]pyrimidine-2-sulfonyl chlorides and substituted anilines and their use as intermediates are also described.
    Type: Grant
    Filed: October 21, 1988
    Date of Patent: December 12, 1989
    Assignee: The Dow Chemical Company
    Inventors: William A. Kleschick, Robert J. Ehr, Mark J. Costales, Ben C. Gerwick, III, Richard W. Meikle, deceased, William T. Monte, Norman R. Pearson
  • Patent number: 4849530
    Abstract: The invention relates to novel crystalline salts of aryloxypropanolamines with diphenylacetic acid, a process for their preparation and the use of these salts for the preparation of chemically pure aryloxy-propanolamines or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: July 18, 1989
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: Gerhard Zol, Gerhard Pfarrhofer
  • Patent number: 4820734
    Abstract: The novel phenethylamine derivatives of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each signify hydrogen, halogen, trifluoromethyl, lower alkoxy, lower alkyl, hydroxy or nitro, with the proviso that at least one of R.sup.1 and R.sup.2 is different from hydrogen, R.sup.3 and R.sup.4 each signify lower alkyl, n signifies the number 1, 2, 3 or 4 and B signifies the group --CO-- or --CHOH--, and their pharmaceutically acceptable acid addition salts have interesting analgesic and antidepressant properties. These substances can be manufactured according to various methods which are known per se and can be used as medicaments in the form of pharmaceutical preparation.
    Type: Grant
    Filed: November 4, 1987
    Date of Patent: April 11, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Karl Bernauer, Hans Bruderer
  • Patent number: 4814507
    Abstract: A novel sulfone compound represented by the general formula (I) ##STR1## wherein R.sup.1 is cyclohexyl, phenyl; or a phenyl substituted with a group selected from nitro, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are respectively hydrogen, halogen, cyano or carbonyl, wherein R.sup.1 and R.sup.2 may form an o-phenylene or an o-phenylene substituted with at least one group selected from nitro C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; X is oxygen or methylkene; Y is -(CH.sub.2).sub.n --, wherein n is an integer of 0, 5 or 6, or ##STR2## wherein m is an integer 1-3; R.sup.6 is hydrogen, C.sub.1 -C.sub.3 alkyl, .omega.-alkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms, or .omega.-dialkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms; R.sup.7 is hydrogen or C.sub.1 -C.sub.3 alkyl; and R.sup.6 and R.sup.7 may form a ring together with N, or ##STR3## wherein R.sup.8 is hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: September 14, 1987
    Date of Patent: March 21, 1989
    Assignee: Mitsubishi Chemical Industries, Limited
    Inventors: Akihiro Tobe, Shinichiro Fujimori, Tomoshi Yamazaki, Mamoru Sugano, Ryoji Kikumoto, Issei Nitta
  • Patent number: 4804670
    Abstract: Substituted hexatriene derivatives of the formula I ##STR1## where R.sup.1 has the meaning given in the description, and their preparation, are described. The compounds may be used to treat acne and psoriasis.
    Type: Grant
    Filed: September 3, 1985
    Date of Patent: February 14, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Joachim Paust, Klaus Schmieder, Axel Nuerrenbach
  • Patent number: 4769483
    Abstract: The invention relates to cycloalkyl substituted 4-aminophenyl derivatives of formula (I) ##STR1## wherein R is C.sub.1 -C.sub.4 alkyl:n is an integer of 1 to 5; and either(a) A is ##STR2## and B is --O--, --NH-- or --CH.sub.2 --; or (b) A is --CH.sub.2 -- and B is --O--, --NH--, --CH.sub.2 -- or ##STR3## or (c) A is --O-- and B is ##STR4## or --CH.sub.2 --; or (d) A is --NH-- and B is ##STR5## or --CH.sub.2 -- and their pharmaceutically acceptable salts.The scope of the invention includes also a process for preparing the said compounds of formula (I) and pharmaceutical compositions containing same.The compounds of the invention show aromatase inhibiting activity and can be useful, e.g., in treating hormone-dependent tumors and prostatic hypertrophy or hyperplasia.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: September 6, 1988
    Assignee: Farmitalia Carlo Erba, S.p.A.
    Inventors: Paolo Lombardi, Angelo Crugnola, Enrico di Salle
  • Patent number: 4767784
    Abstract: The invention relates to novel crystalline salts of aryloxypropanolamines with diphenylacetic acid, a process for their preparation and the use of these salts for the preparation of chemically pure aryloxy-propanolamines or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: November 28, 1986
    Date of Patent: August 30, 1988
    Inventors: Gerhard Zolss, Gerhard Pfarrhofer
  • Patent number: 4734500
    Abstract: A novel sulfone compound represented by the general formula (I) ##STR1## wherein R.sup.1 is cyclohexyl, phenyl; or a phenyl substituted with a group selected from nitro, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are respectively hydrogen, halogen, cyano or carbonyl, wherein R.sup.1 and R.sup.2 may form an o-phenylene or an o-phenylene substituted with at least one group selected from nitro C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; X is oxygen or methylene; Y is --(CH.sub.2).sub.n --, wherein n is an integer of 0, 5 or 6, or ##STR2## wherein m is an integer 1-3; R.sup.6 is hydrogen, C.sub.1 -C.sub.3 alkyl, .omega.-alkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms, or .omega.-dialkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms; R.sup.7 is hydrogen or C.sub.1 -C.sub.3 alkyl; and R.sup.6 and R.sup.7 may form a ring together with N, or ##STR3## wherein R.sup.8 is hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: March 11, 1986
    Date of Patent: March 29, 1988
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Akihiro Tobe, Shinichiro Fujimori, Tomoshi Yamazaki, Mamoru Sugano, Ryoji Kikumoto, Issei Nitta
  • Patent number: 4717492
    Abstract: A product of reaction suitable for use as a lubricant additive made by reacting a preformed Mannich base with a reactive hydrocarbyl amine, thiol or dithiophosphoric acid having at least one reactive hydrogen.
    Type: Grant
    Filed: December 27, 1985
    Date of Patent: January 5, 1988
    Assignee: Mobil Oil Corporation
    Inventor: Sheldon Chibnik
  • Patent number: 4661601
    Abstract: New compounds having the formula 1 ##STR1## wherein W is hydrogen, halogen, n-alkyl, --NHCOR.sup.1, --COR.sup.1, or phenoxyacetylamino optionally substituted by one or two C.sub.1-12 straight- or branched chain alkyl, X is a substituent in the coupling position and is selected from hydrogen, chlorine, bromine, --SR.sup.11 or a nitrogen-containing heterocyclic residue attached at a ring nitrogen atom, and Y is a group having the formula 2 ##STR2## wherein Q is selected from the residues: --COOR.sup.4 or --CONR.sup.4 R.sup.5, --OM, --NR.sup.7 R.sup.8, --PO(OR.sup.9)[O].sub.x R.sup.10 with X=0 or 1, --SO.sub.2 OH, --SO.sub.2 NR.sup.4 R.sup.5 or CN. The groups R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, M, k and n are defined hereinafter.These compounds are used as black color couplers in photographic materials.
    Type: Grant
    Filed: April 3, 1985
    Date of Patent: April 28, 1987
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4541954
    Abstract: A novel process for preparing 6-chloro-N-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine comprising cyclizing N-methyl-N-[2-(2'-chlorophenyl)ethyl]-2-chloroethylamine hydrochloride in a solution of trichlorobenzene and aluminum chloride.
    Type: Grant
    Filed: September 5, 1984
    Date of Patent: September 17, 1985
    Assignee: SmithKline Beckman Corporation
    Inventors: Stanley J. Borowski, Thomas A. Post
  • Patent number: 4536601
    Abstract: Optically active N-substituted phenylalaninols of the formula (I): ##STR1## wherein R is isopropyl, 1-ethylpropyl, cyclopentyl, cyclohexyl, cycloheptyl, 4-methylbenzyl, 4-methoxybenzyl, or 3,4-methylenedioxybenzyl; and acid addition salts thereof which are useful as a resolving agent, and a process for preparing D-3-acetylthio-2-methylpropionic acid which comprises reacting DL-3-acetylthio-2-methylpropionic acid with an optically active N-substituted phenylalaninol of the formula (I) to form diastereomeric salts, subjecting the formed diastereomeric salts to a fractional crystallization from a solvent to separate the D-acid salt from the L-acid salt, and then decomposing the D-acid salt with a mineral acid to give D-3-acetylthio-2-methylpropionic acid.
    Type: Grant
    Filed: September 23, 1983
    Date of Patent: August 20, 1985
    Assignee: Dainippon Pharmaceutical Co., Ltd.
    Inventors: Masatoshi Tukamoto, Tadahiro Sawayama
  • Patent number: 4535186
    Abstract: This invention provides a group of hydroxycycloalkanephenethyl amine antidepressant derivatives of the following structural formula: ##STR1## in which A is a moiety of the formula ##STR2## where the dotted line represents optional unsaturation;R.sub.1 is hydrogen or alkyl;R.sub.2 is alkyl;R.sub.4 is hydrogen, alkyl, formyl or alkanoyl;R.sub.5 and R.sub.6 are, independently, hydrogen, hydroxyl, alkyl, alkoxy, alkanoyloxy, cyano, nitro, alkylmercapto, amino, alkylamino, dialkylamino, alkanamido, halo, trifluoromethyl or, taken together, methylenedioxy;R.sub.7 is hydrogen or alkyl; andn is 0, 1, 2, 3 or 4;or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: October 26, 1983
    Date of Patent: August 13, 1985
    Assignee: American Home Products Corporation
    Inventors: G. E. Morris Husbands, John P. Yardley, Eric A. Muth
  • Patent number: 4535162
    Abstract: A process is herein described for catalytically reducing nitroaromatic compounds by displacement of hydrogen from carbon monoxide and water or from synthesis gas to nitroaromatic compounds, the catalytic reduction being catalyzed by complexes of rhodium, iridium, ruthenium and osmium; said process is characterized in that the CO+H.sub.2 O system or the (CO+H.sub.2)+H.sub.2 O system is caused to react with a nitroaromatic compound of formula:Ar--(NO.sub.2).sub.x (I)wherein Ar is an aryl or hetero-aryl group, also substituted by inert groups; x is an integer from 1 to 3, in the presence of a complex catalyst of formula:[MChel(L).sub.2 ].sup.+ X.sup.- (II)or of a catalyst composed by carbonyl compounds and chelants of formula:Mz(CO).sub.y +nChel (III)wherein M=Rh, Ir, Ru, Os; "Chel" is a bidentate or tridentate aromatic nitrogen chelating compound; "L" is a molecule of carbon monoxide or of an olefin or half a molecule of a diolefin; X.sup.- is an anion selected from Cl.sup.-, Br.sup.-, I.sup.-, PF.sub.6.sup.
    Type: Grant
    Filed: June 16, 1983
    Date of Patent: August 13, 1985
    Assignee: Montedison S.p.A.
    Inventors: Giovanni Mestroni, Grazia Zassinovich, Enzo Alessio
  • Patent number: 4526893
    Abstract: Compounds of the structure ##STR1## wherein X, R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are as herein defined, effective as .beta.-blockers and hypotensive agents, are described.
    Type: Grant
    Filed: December 16, 1983
    Date of Patent: July 2, 1985
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Toshihiro Takahashi, Noriyoshi Sueda, Masahiro Tsuji, Yoshiyuki Tahara, Hiroyasu Koyama, Yoshikuni Suzuki, Masao Nagase, Toshiji Sugai
  • Patent number: 4496736
    Abstract: Carboxylic acids and N-t.-alkylamines can be prepared simultaneously by the alkaline pressure hydrolysis of N-t.-alkyl carboxylic acid amides. A 5 to 50% strength by weight aqueous solution of an alkali metal hydroxide is employed for this purpose in an amount of 1.0 to 1.3 mols per mol of the amide. The process is carried out at 200.degree. to 350.degree. C.
    Type: Grant
    Filed: June 3, 1982
    Date of Patent: January 29, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Bonse, Gerhard Marzolph, Heinz U. Blank
  • Patent number: 4473586
    Abstract: Disclosed herein are 1-aminoalkyl-3,4-dihydronaphthalenes represented by the formula ##STR1## wherein n is 1 or 2; R, R.sub.1, and R.sub.2 are independently selected from hydrogen, hydroxy, loweralkoxy of 1 to 3 carbon atoms, loweralkenyloxy of 1 to 3 carbon atoms, thiomethyl, halo, or ##STR2## wherein R.sub.5 and R.sub.6 are independently selected from hydrogen, loweracyl of 1 to 4 carbon atoms or sulfonyl of the formula ##STR3## wherein R.sub.7 is loweralkyl of 1 to 4 carbon atoms; or R and R.sub.1, or R.sub.1 and R.sub.2 can be taken together to form a methylenedioxy or ethylenedioxy bridge; with the proviso that at least one of R, R.sub.1 or R.sub.2 must be other than hydrogen; and R.sub.3 and R.sub.4 are independently selected from hydrogen; loweralkyl of 1 to 4 carbon atoms; halo-substituted loweralkyl of 1 to 4 carbon atoms; arylalkyl of the formula ##STR4## wherein m is 0, 1 or 2, p is 0 or 1, R.sub.8 is hydrogen or loweralkyl of 1 to 4 carbon atoms and R.sub.9 and R.sub.
    Type: Grant
    Filed: May 3, 1982
    Date of Patent: September 25, 1984
    Assignee: Abbott Laboratories
    Inventors: John F. Debernardis, David L. Arendsen, Martin Winn
  • Patent number: 4454157
    Abstract: The invention relates to a pharmaceutical composition comprising a tetracyclononane derivative of the formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are hydrogen atoms or alkyl radicals and A is CH.sub.2 CH.sub.2 or CH--R.sup.4 in which R.sup.4 is a hydrogen atom or an alkyl, cyclohexyl, phenylalkyl or optionally-substituted phenyl radical, or a salt thereof. The majority of compounds of the formula II are novel and they are included within the scope of the invention, as are processes for their manufacture. Typical of the compounds disclosed is 8-(1-amino-ethyl)tetracyclo[4,3,0,0.sup.2,4,0.sup.3,7 ]nonane.
    Type: Grant
    Filed: August 17, 1982
    Date of Patent: June 12, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventor: Douglas L. Swallow
  • Patent number: 4429158
    Abstract: Disclosed ar novel polyamine compounds having the general formula ##STR1## wherein R, R.sup.1, R.sup.2 and R.sup.3 are each independently selected from hydrogen and alkyl groups which may be substituted, the preparation of such compounds and their use as curing agents for epoxy resins.
    Type: Grant
    Filed: September 14, 1981
    Date of Patent: January 31, 1984
    Assignee: Eastman Kodak Company
    Inventors: Raymond H. Good, Paul McBride
  • Patent number: 4417896
    Abstract: Novel compounds of the general formula ##STR1## wherein Z represents a substituted lower alkyl radical; each of R.sub.1 and R.sub.2 is hydrogen atom, a lower alkyl or a substituted lower alkyl identical with or different from Z and the functional groups NO.sub.2 and NR.sub.1 R.sub.2 can occupy all ring positions in relation to OZ, with the exception that if Z is .beta.-hydroxyethyl, --NO.sub.2 is in the 4 position and --N(R.sub.1)(R.sub.2) is in the 2 position then either R.sub.1 or R.sub.2 is other than hydrogen.The novel compounds are for dyeing human hair in a variety of yellow shades. The compounds of formula (I) may be used as aqueous or water-alcohol solutions to form dye compositions for dyeing human hair.
    Type: Grant
    Filed: April 6, 1982
    Date of Patent: November 29, 1983
    Assignee: Societe Anonyme dite: L'Oreal
    Inventors: Andree Bugaut, Patrick Andrillon
  • Patent number: 4402975
    Abstract: A compound represented by the following formula ##STR1## wherein R.sup.1 represents a hydrogen atom, an acyl group or an alkoxycarbonyl group; X.sup.1 represents an alkylene group having 3 to 6 carbon atoms, a 1,4-cyclohexylene group, or a 1,4-phenylene group, the alkylene group may be substituted by an alkyl group having 1 to 6 carbon atoms, and the 1,4-phenylene group may be substituted by 1 or 2 substituents selected from halogen atoms and alkoxy groups having 1 to 6 carbon atoms; R.sup.2 represents a hydrogen atom or a hydroxyl group and R.sup.3 represents hydrogen atom, or R.sup.2 and R.sup.3 together may form an oxo group (.dbd.O), and when X.sup.1 is other than the 1,4-phenylene group, R.sup.2 represents a hydrogen atom and R.sup.3 represents a bond between the carbon atoms to which R.sup.3 is bonded and that carbon atom of X.sup.1 which is adjacent to said carbon atom; X.sup.
    Type: Grant
    Filed: July 17, 1981
    Date of Patent: September 6, 1983
    Assignee: Teijin Limited
    Inventors: Toru Takeshita, Kenji Hoshina, Akira Ohtsu, Tatsuyuki Naruchi
  • Patent number: 4357352
    Abstract: The invention relates to a pharmaceutical composition comprising a tetracyclononane derivative of the formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are hydrogen atoms or alkyl radicals and A is CH.sub.2 CH.sub.2 or CH--R.sup.4 in which R.sup.4 is a hydrogen atom or an alkyl, cyclohexyl, phenylalkyl or optionally-substituted phenyl radical, or a salt thereof. The majority of compounds of the formula II are novel and they are included within the scope of the invention, as are processes for their manufacture. Typical of the compounds disclosed is 8-(1-amino-ethyl)tetracyclo-[4,3,0,0.sup.2,4,0.sup.3,7 ]nonane.
    Type: Grant
    Filed: December 4, 1978
    Date of Patent: November 2, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventor: Douglas L. Swallow
  • Patent number: 4349690
    Abstract: The present invention provides novel 9-deoxy-9-methylene-6-keto-PGE derivatives which are useful for platelet aggregation inhibition and gastric cyctoprotection.
    Type: Grant
    Filed: April 23, 1981
    Date of Patent: September 14, 1982
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4337061
    Abstract: Novel compounds of the general formula ##STR1## wherein Z represents a substituted lower alkyl radical; each of R.sub.1 and R.sub.2 is hydrogen atom, a lower alkyl or a substituted lower alkyl identical with or different from Z and the functional groups NO.sub.2 and NR.sub.1 R.sub.2 can occupy all ring positions in relation to OZ, with the exception that if Z is .beta.-hydroxyethyl, --NO.sub.2 is in the 4 position and --N(R.sub.1)(R.sub.2) is in the 2 position then either R.sub.1 or R.sub.2 is other than hydrogen.The novel compounds are for dyeing human hair in a variety of yellow shades. The compounds of formula (I) may be used as aqueous or water-alcohol solutions to form dye compositions for dyeing human hair.
    Type: Grant
    Filed: May 3, 1976
    Date of Patent: June 29, 1982
    Assignee: Societe Anonyme dite: L'OREAL
    Inventors: Andree Bugaut, Patrick Andrillon