Nitrogen In Acid Moiety Patents (Class 560/16)
  • Patent number: 5252745
    Abstract: Antimicrobial compounds of the formula ##STR1## wherein R.sup.1 is selected from the group consisting of H, an amine protective group, and a moiety of the formula ##STR2## wherein R.sup.2, R.sup.5, and R.sup.6 are independently selected from H and an amine protective group;R.sup.3 and R.sup.4 are independently selected from H, lower alkyl, aryl, arylalkyl, CH.sub.2 OR, CH.sub.2 SR or CH(CH.sub.3)OR;R=H, propargyl lower alkyl, arylalkyl or aryl;wherein R.sup.1 and R.sup.2 or R.sup.5 and R.sup.6 can be joined to form a ring; and wherein when R.sup.1 and R.sup.2 or R.sup.5 and R.sup.6 are both H, the compound is either in free base form or in salt form.
    Type: Grant
    Filed: May 21, 1991
    Date of Patent: October 12, 1993
    Assignee: Rohm and Haas Company
    Inventors: Margaret M. Bowers-Daines, Barry C. Lange
  • Patent number: 5237089
    Abstract: N-substituted 3,4,5,6-tetrahydrophthalimides and their intermediates of the general formula I ##STR1## where A is --NO.sub.2, --NH.sub.2 or ##STR2## corresponding to the compounds Ia, Ib and Ic, B is --CH.sub.2 --, --CH.sub.2 --CHR.sup.1 --, --CH.sub.2 --CHR.sup.1 --CH.sub.2 --, --CH.dbd., --CH.dbd.CR.sup.1 -- or --CH.dbd.CR.sup.1 --CH.dbd., R.sup.1 being --H, --Cl, --Br or --CH.sub.3, D is ##STR3## or .dbd.C<, depending on the terminal group B, X is --H, --Cl or --Br, Y is --H, C.sub.1 -C.sub.7 -alkyl, --Cl, --Br, --CN, --CONH.sub.2 or --CO.sub.2 R.sup.2, where R.sup.2 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.5 - or C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylmercapto-C.sub.2 -C.sub.4 -alkyl, propargyl, benzyl, .alpha.-phenylethyl, .alpha.-phenylpropyl, C.sub.2 -C.sub.4 -alkyl which is monosubstituted, disubstituted or trisubstituted by F or Cl, or CH.sub.3 -substituted or Cl-substituted allyl, and Z is --COOR.sup.2, --CONR.sup.3 R.sup.4, ##STR4## or --COR.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: August 17, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Plath, Karl Eicken, Norbert Goetz, Jochen Wild, Norbert Meyer, Bruno Wuerzer
  • Patent number: 5219886
    Abstract: Novel mercapto-acylamino acids of the formula ##STR1## wherein Q is hydrogen or R.sup.7 CO--;R.sup.1 is lower alkyl, cyclolower alkyl, aryl or heteroaryl;R.sup.2 is hydrogen; lower alkyl; cyclolower alkyl; lower alkyl substituted with hydroxy, lower alkoxy, mercapto, lower alkylthio, aryl or heteroaryl; aryl; or heteroaryl;R.sup.3 is --OR.sup.5 or --NR.sup.5 R.sup.6 ;R.sup.4 and R.sup.9 are independently --(CH.sub.2).sub.q R.sup.8, provided that when R.sup.4 and R.sup.9 are both hydrogen, R.sup.2 is biphenylyl, phenoxyphenyl, phenylthiophenyl, naphthyl, heteroaryl, or lower alkyl substituted with hydroxy, lower alkoxy, mercapto or lower alkylthio;R.sup.5 and R.sup.6 are independently selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl and aryl lower alkyl, or R.sup.5 and R.sup.6 together with the nitrogen to which they are attached form a 5-7 membered ring;R.sup.7 is hydrogen, lower alkyl or aryl;R.sup.
    Type: Grant
    Filed: October 1, 1991
    Date of Patent: June 15, 1993
    Assignee: Schering Corporation
    Inventors: Elizabeth M. Smith, Philip M. DeCapite, Bernard R. Neustadt
  • Patent number: 5220022
    Abstract: Disclosed are novel compounds of the formula ##STR1## wherein: R is ##STR2## where Ph is phenyl, or ##STR3## X is --NR.sub.5 R.sub.6 or --OR.sub.7 ; R.sub.1 and R.sub.2 are independently hydrogen, methyl, ethyl, cyclohexyl, ##STR4## butyl, or heptyl; R.sub.4 is o-phenylene or p-phenylene and R.sub.4 can be alkyl- halo- or alkoxy- substituted;R.sub.3 is hydrogen;R.sub.5, R.sub.6, and R.sub.7 are independently hydrogen, methyl, ethyl, tert-butyl, isobutyl, butyl, alkoxy, acyl, acylamino, aryl, amino, cyclohexyl, aminoalkyl and substituted or unsubstituted phenylamino;Y is sulfur and oxygen atom; and n is zero or 1; provided n=1 when Y is sulfur.
    Type: Grant
    Filed: January 28, 1991
    Date of Patent: June 15, 1993
    Assignee: International Paper Co.
    Inventors: Bruce M. Resnick, Allan J. Wexler
  • Patent number: 5214181
    Abstract: This invention relates to novel compounds of the formula [I], which are useful for treatment of various diseases such as immunodeficiency and autoimmune diseases caused by immune disorders, processes for preparing the compounds and compositions containing the compounds as active ingredients.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: May 25, 1993
    Assignee: Santen Pharmaceutical Co., Ltd.
    Inventors: Takakazu Morita, Shiro Mita, Yoichi Kawashima
  • Patent number: 5214201
    Abstract: This invention relates to certain salts of leukotriene antagonists and the use of a particular amine to form these salts as a means for selectively crystallizing optical isomers of the leukotriene antagonists disclosed herein.
    Type: Grant
    Filed: December 12, 1991
    Date of Patent: May 25, 1993
    Assignee: SmithKline Beecham Corporation
    Inventor: Robert J. Mills
  • Patent number: 5209930
    Abstract: Antimicrobial compounds of the formula ##STR1## wherein R.sup.1 is selected from the group consisting of H, lower (C.sub.1 -C.sub.4)alkyl, alkyl aryl, CH.sub.2 OR, CH.sub.2 SR, and CH(CH.sub.3)OR; andR, R.sup.2, and R.sup.3 are independently selected from H, (C.sub.1 -C.sub.4)alkyl, aryl, arylalkyl, alkaryl, and halopropargyl.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: May 11, 1993
    Assignee: Rohm and Haas Company
    Inventors: Margaret M. Bowers-Daines, Barry C. Lange
  • Patent number: 5198569
    Abstract: The asymmetric hydrogenation of aliphatic .alpha.-keto esters in the presence of rhodium catalysts which contain as chiral ligand a diphosphine of formula IV(R.sub.3).sub.2 P--Q--P(R.sub.3)hd 2 (IV)wherein R.sub.3 is phenyl, C.sub.1 -C.sub.6 alkylphenyl or C.sub.1 -C.sub.6 alkoxyphenyl, and Q is [2,2,1]-bicyloheptan-1,2-ylene or [2,2,1]-bicyclohept-4,5-en-1,2-ylene, gives the corresponding (R)- or(S)-.alpha.-hydroxycarboxylic acid esters in high rates of chemical conversion and in high enantiomer excesses.
    Type: Grant
    Filed: September 11, 1991
    Date of Patent: March 30, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Ulrich Pittelkow, Felix Spindler
  • Patent number: 5196563
    Abstract: Novel N-phenyl-N-carboxythioureas of the formula I ##STR1## in which R.sub.1 and R.sub.2 each represents C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.7 cycloalkyl or C.sub.5 -C.sub.6 cycloalkenyl,R.sub.3 represents hydrogen, halogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy or C.sub.1 -C.sub.10 alkylthio,R.sub.4 represents C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl or phenyl-C.sub.1-C.sub.7 alkyl; C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl or phenyl-C.sub.1 -C.sub.7 alkyl each mono- or poly-substituted by halogen or interrupted one or several times by oxygen and/or sulphur; C.sub.3 -C.sub.8 cycloalkyl; or C.sub.3 -C.sub.8 cycloalkyl mono- or poly-substituted by halogen or by C.sub.1 -C.sub.5 alkyl, andR.sub.5 represents C.sub.1 -C.sub.10 alkyl; phenyl-C.sub.1 -C.sub.7 alkyl; C.sub.1 -C.sub.10 alkyl or phenyl-C.sub.1 -C.sub.7 alkyl each mono- or poly-substituted by halogen or interrupted one or several times by oxygen and/or sulphur; C.
    Type: Grant
    Filed: November 14, 1989
    Date of Patent: March 23, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Jozef Drabek, Josef Ehrenfreund
  • Patent number: 5192357
    Abstract: The invention provides compounds of formula I ##STR1## wherein W, D, R.sup.1, R.sup.2, R.sup.3, x, m, n and p are as defined in the description. The compound have valuable pesticidal activity especially against fungi, insects, nematodes, acarids and weeds.
    Type: Grant
    Filed: July 8, 1988
    Date of Patent: March 9, 1993
    Assignee: Schering Agrochemicals Limited
    Inventors: Geoffrey R. Cliff, Ian C. Richards
  • Patent number: 5192803
    Abstract: Novel substituted 2-phenoxyphenoxyethylcarbamic esters of the formula I ##STR1## where R.sub.1 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl, R.sub.2 is C.sub.1 -C.sub.4 alkyl or a radical of the formula ##STR2## --C(CH.sub.3).sub.2 --CN or --N(R.sub.9)--COO--C.sub.1 -C.sub.4 alkyl, R.sub.3 and R.sub.4 independently of one another are hydrogen or methyl, R.sub.5 is fluorine or chlorine, R.sub.6 is either identical to the substituents given in the case of R.sub.5 or is hydrogen, R.sub.7 and R.sub.8 independently of one another are hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or nitro, R.sub.9 is C.sub.1 -C.sub.4 alkyl and n is zero, one or two, their preparation, their use in pest control, and pesticides containing these carbamic esters as active substance, are described. The preferred field of application is the control of pests on animals and plants, in partcular of eggs and larvae of phytophagous harmful insects and harmful mites.
    Type: Grant
    Filed: June 24, 1991
    Date of Patent: March 9, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Friedrich Karrer
  • Patent number: 5191119
    Abstract: Methods are provided for substituting aromatic carboxylic acids and derivatives thereof and amino substituted aromatic carboxylic acids and derivatives thereof, by forming imides and imide-amides, respectively, by acylation with aliphatic carboxylic acids, substituting at least one nitrogen atom under mild basic conditions with an aliphatic compound having as alkylating agent a displaceable functionality and removing undesired acyl groups, as appropriate.
    Type: Grant
    Filed: July 5, 1990
    Date of Patent: March 2, 1993
    Assignee: Cook Imaging Corp.
    Inventors: Milos Sovak, Ramachandran Ranganathan
  • Patent number: 5189063
    Abstract: Pesticidal substituted acrylic esters of the formula ##STR1## in which R.sup.1 represents alkyl, or represents unsubstituted or substituted aralkyl,R.sup.2 represents dialkylamino, or represents a radical --Z--R.sup.3,R.sup.3 represents alkyl, or represents unsubstituted or substituted aralkyl,Z represents oxygen or sulphur,A represents ##STR2## where n represents a number from 0 to 6,R.sup.4 and R.sup.5 in each case independently of one another represent alkyl, or together represent an alkylene chain having 2 to 7 carbon atoms, andR.sup.6 represents alkyl, or represents a radical ##STR3## where R.sup.7 represents alkyl, alkoxy or dialkylamino,B represents the group CH--R.sup.8 or, whereR.sup.9 represents unsubstituted or substituted alkyl, alkenyl, alkynyl, aralkyl, aryl or hetaryl, andR and Q independently of one another represent hydrogen, alkyl, halogenoalkyl or alkoxy.
    Type: Grant
    Filed: August 17, 1990
    Date of Patent: February 23, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Alexander Klausener, Herbert Gayer, Wolfgang Kramer, Dieter Berg, Wilhelm Brandes, Gerd Hanssler, Ulrike Wachendorff-Neumann
  • Patent number: 5187183
    Abstract: The invention relates to novel S-nitroso derivatives of ACE inhibitors and to pharmaceutical compositions comprising the S-nitrosothiol derivatives of the invention together with a pharmaceutically acceptable carrier.The invention also relates to methods for treating various pathophysiological conditions including acute myocardial infarction, left ventricular dysfunction without overt heart failure, hypertension, pulmonary hypertension, congestive heart failure, angina pectoris, vascular thrombosis, Raynauds syndrome, scleroderma, toxemia of pregnancy, acute renal failure, diabetic nephropathy, and renal artery stenosis, and to methods of inhibiting ACE and effecting vasodilation comprising administering the S-nitrosothiol derivatives of the ACE inhibitors of the invention to an animal.
    Type: Grant
    Filed: June 14, 1991
    Date of Patent: February 16, 1993
    Assignee: Brigham & Women's Hospital
    Inventors: Joseph Loscalzo, John Cooke
  • Patent number: 5185368
    Abstract: Compounds of the formula ##STR1## in which R is alkyl having up to 4 carbon atoms, n has an average value of at least 9, X is a radical of the formula --C(.dbd.O)--(NH--SO.sub.2).sub.m -- in which m is 0 or 1 and, if m is 1, the carbonyl group may be bonded to the oxygen atom or to the nitrogen atom, and each of the radicals A.sub.1, A.sub.2 and A.sub.3, independently of the others, is hydrogen or an acyl radical, and salts of salt-forming compounds of formula I, as well as metal complexes of compounds of formula I, in which A.sub.1, A.sub.2 and A.sub.3, are hydrogen can be used as metal chelators and as auxiliaries in diagnosis.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: February 9, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinrich Peter, Theophile Moerker
  • Patent number: 5180418
    Abstract: Cycloalkanecarboxylic acid derivatives of formula I ##STR1## wherein W is ##STR2## and A is CO--R.sub.3 or CN; R.sub.1 is hydrogen or fluorine; R.sub.2 is halogen or cyano; R.sub.3 is chlorine, X--R.sub.5, amino, C.sub.1 -C.sub.4 alkylamino, d-C.sub.1 -C.sub.4 alkylamino, C.sub.2 -C.sub.4 haloalkylamino, di-C.sub.2 -C.sub.4 haloalkylamino, C.sub.1 -C.sub.4 hydroxyalkylamino, di-C.sub.1 -C.sub.4 hydroxyalkylamino, C.sub.3 -C.sub.4 alkenylamino, diallylamino, --N-pyrrolidino, --N-piperidino, --N-morpholino, --N-thiomorpholino, --N-piperidazino, the group --O--N.dbd.C--(R.sub.9)R.sub.10 or the group --N--R.sub.6 (OR.sub.6); each of R.sub.4 and R.sub.14, independently of the other, is hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 alkyl or trifluoromethyl; R.sub.5 is hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl, halo-C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.10 alkylthio-C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 alkylamino-C.sub.1 -C.sub.4 alkyl, cyano-C.sub.1 -C.sub.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: January 19, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Georg Pissiotas, Hans Moser, Hans-Georg Brunner, Eginhard Steiner
  • Patent number: 5177109
    Abstract: Compounds, compositions and methods are described for treating a CNS disorder such as a cognitive disorder, epilepsy, depression, Parkinson's disease, Alzheimer's disease, a neurodegenerative disease or neurotoxic injury. Compound of interest are 2-amino-4,5-methyleneadipic acid compounds and derivatives defined by the formula I: ##STR1## wherein R.sup.1 is selected from hydrido, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, ##STR2## with each of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein each of X and Y is independently selected from hydroxyl, alkoxy, alkylthio, amino and ##STR3## with each of R.sup.6 and R.sup.7 being independently selected from hydrido, alkyl, cycloalkyl, aryl and aralkyl; wherein any of R.sup.1 through R.sup.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: January 5, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Roberto Pellicciari, Benedetto Natalini, Maura Marinozzi, Alexis A. Cordi, Joseph B. Monahan, Thomas H. Lanthorn
  • Patent number: 5175153
    Abstract: The present invention is novel substituted .alpha.-amino acids, pharmaceutical compositions, method of use, and preparations therefore having utility for treating disorders which benefit from blockade of aspartate and glutamate receptors.
    Type: Grant
    Filed: October 14, 1988
    Date of Patent: December 29, 1992
    Assignee: Warner-Lambert Company
    Inventors: Christopher F. Bigge, James T. Drummond, Vlad E. Gregor, Graham Johnson, Michael R. Pavia
  • Patent number: 5173506
    Abstract: Novel N-(mercaptoalkyl)urea or carbamates of the formulae I and II ##STR1## wherein A is a monocyclic or bicyclic arylene or heteroarylene;Q is hydrogen or R.sub.9 CO--;Y is --O--, --S-- or --NR.sub.8 --;R.sub.1 is lower alkyl, cyclolower alkyl, aryl or heteroaryl;R.sub.2 and R.sub.8 are independently hydrogen; lower alkyl; cyclolower alkyl; lower alkyl substituted with hydroxy, lower alkoxy, mercapto, lower alkylthio, aryl or heteroaryl; aryl; or heteroaryl;R.sub.3 is --OR.sub.5 or --NR.sub.5 R.sub.6 ;R.sub.4 is --(CH.sub.2).sub.q R.sub.7 ; or R.sub.2 and R.sub.4 and the carbons to which they are attached complete a 5-, 6- or 7-membered carbocyclic ring;R.sub.5 and R.sub.6 are independently selected from the group consisting of hydrogen, lower alkyl, hydroxy lower alkyl, lower alkoxy lower alkyl and aryl lower alkyl, or R.sub.5 and R.sub.6 together with the nitrogen to which they are attached form a 5-, 6- or 7-membered ring;R.sub.
    Type: Grant
    Filed: August 16, 1990
    Date of Patent: December 22, 1992
    Assignee: Schering Corporation
    Inventors: Bernard R. Neustadt, Alan Bronnenkant
  • Patent number: 5164526
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each represent hydrogen, alkyl, alkenyl, cycloalkyl, aryl or aralkyl are produced by a new environmentally acceptable process.
    Type: Grant
    Filed: October 2, 1990
    Date of Patent: November 17, 1992
    Assignee: Biochemie Gesellschaft m.b.H.
    Inventor: Ingolf Macher
  • Patent number: 5155100
    Abstract: The invention relates to the N-phosphonomethyl-biaryl substituted dipeptide derivatives of formula I ##STR1## wherein A represents a direct bond, lower alkylene, phenylene or cyclohexylene; m represents 1 or zero, provided that m represents 1 when A is a direct bond; R.sub.2 represents hydrogen, hydroxy, lower alkyl, aryl-lower alkyl, C.sub.5 -C.sub.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: October 13, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Mark D. Erion, Stephane De Lombaert
  • Patent number: 5145874
    Abstract: Provided are cyclic hydrocarbons of Formula I ##STR1## with an aminoalkyl sidechain that are useful for treating phospholipase A2 mediated conditions, diabetes, and obesity.
    Type: Grant
    Filed: February 25, 1991
    Date of Patent: September 8, 1992
    Assignee: The Upjohn Company
    Inventors: Roy A. Johnson, Gordon L. Bundy, Gilbert A. Youngdale, Douglas R. Morton, Donald P. Wallach, deceased, by Vera M. Wallach, legal representative
  • Patent number: 5138071
    Abstract: A process for preparing dipeptides with N-terminal non-proteinogenous amino acids of the formula ##STR1## in which R.sup.1 to R.sup.6 have the meaning stated in the description, from compounds of the formula ##STR2## is described.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: August 11, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Schoellkopf, Ulrich Groth, Meinolf Lange
  • Patent number: 5112868
    Abstract: The present invention is novel selected hydroxamic acid derivatives of acyl residues of selected NSAIDS, i.e. having 5-lipoxygenase and cyclooxygenase inhibiting properties, pharmaceutical compositions for treating conditions advantageously affected by the inhibition and methods for treating these conditions in mammals, including humans suffering therefor.
    Type: Grant
    Filed: May 2, 1990
    Date of Patent: May 12, 1992
    Assignee: Warner-Lambert Company
    Inventors: Wiaczeslaw A. Cetenko, David T. Connor, Daniel L. Flynn, Jagadish C. Sircar
  • Patent number: 5106870
    Abstract: This invention relates to several thromboxane A.sub.2 inhibiting 7-[3-.alpha.-[1-[[(phenylamino)-thioxomethyl]hydrazono]ethyl]-bicyclo[2.2. 1]-heptenoic acids, pharmaceutical compositions employing them and methods of their use.
    Type: Grant
    Filed: September 10, 1990
    Date of Patent: April 21, 1992
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 5096925
    Abstract: Disclosed are compounds of the formula ##STR1## wherein X and Y independently represent hydroxymethyl; cyano; carboxy; functionally modified carboxy selected from esterified carboxy, carbamoyl, and N-substituted carbamoyl; 5-tetrazolyl; 2-oxazolyl, 4,5-dihydro-2-oxazolyl, 2-imidazoly or 4,5-dihydro-2-imidazolyl or any said grouping substituted by lower alkyl; R and R.sub.o independently represent hydrogen, lower alkyl, (C.sub.3 -C.sub.7)-cycloalkyl-lower alkyl, or aryl-lower alkyl in which aryl represents phenyl, pyridyl, thienyl, furyl, biphenyl or naphthyl, each unsubstituted or mono- or di-substituted by halogen, lower alkyl, hydroxy, acyloxy, lower alkoxy, trifluoromethyl or cyano; A represents straight chain (C.sub.2 -C.sub.5)-alkylene; or A represents straight chain (C.sub.2 -C.sub.
    Type: Grant
    Filed: April 11, 1990
    Date of Patent: March 17, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Gary M. Ksander
  • Patent number: 5095114
    Abstract: The invention relates to a process for the enantiomer-selective preparation of .gamma.-keto-.delta.-amino acid derivatives of the formula I ##STR1## characterized in that a compound of the formula II ##STR2## is converted, using a trialkylchlorosilane, into a compound of the formula III ##STR3## this compound is then reacted with a diazoacetate of the formula N.sub.2 CH.sub.2 COOR.sup.4 (R.sup.4 .noteq.H) to give a cyclopropane compound of the formula IV ##STR4## and then the compound IV is converted, by ring-opening and removal of the silyl groups, and where appropriate saponification, into the compound of the formula I, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 having the meanings indicated in claim 1.
    Type: Grant
    Filed: June 19, 1990
    Date of Patent: March 10, 1992
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Hans-Eckart Radunz, Hans U. Reissig
  • Patent number: 5091414
    Abstract: A compound of Formula (I):(I) R.sup.1 (CA.dbd.CA.sup.1).sub.x --C(.dbd.X)NR.sup.2 R.sup.3where R.sup.1 is alkyl optionally substituted by a group selected from alkoxy, alkenyl, alkynyl, alkenyloxy, alkynyloxy, aryl, aryloxy, arylalkoxy and cycloalkyl fused to an aryl ring; x=1 or 2; X=O or S; each A and A.sup.1 is independently hydrogen, alkyl or haloalkyl; R.sup.2 is alkyl, alkenyl or cycloalkyl any of which may be substituted by halo, alkenyl, alkyl, cycloalkyl, alkynyl, dioxalanylalkyl or alkoxy; and R.sup.3 is selected from groups (A) to (D):(A) --Y=X.sup.1 --(R.sup.4).sub.a where X.sup.1 is O or S, Y is phosphorus or carbon, R.sup.4 is hydrogen, alkyl, alkoxy, acyl or CO.sub.2 R.sup.5 where R.sup.5 is alkyl or aryl, and a is 1 or 2(B) --S(R.sup.6)(O).sub.bwhere R.sup.6 is alkyl, aryl, aryloxy, alkoxy, thioalkoxy, thioaryl, alkythio, alkoxythio or arylthio and b is 0, 1 or 2(C) --S(O).sub.c NR.sup.7 R.sup.8where c is 0, 1 or 2, R.sup.7 is --COR.sup.9 or --CO.sub.2 R.sup.9 where R.sup.
    Type: Grant
    Filed: November 29, 1990
    Date of Patent: February 25, 1992
    Assignee: Burroughs Wellcome Co.
    Inventors: Malcolm H. Black, Robert J. Blade, Robert J. Peek
  • Patent number: 5077309
    Abstract: Novel compounds have the formula (I) ##STR1## where ##STR2## represents one of the divalent cyclic groups ##STR3## the letters a and b indicating in each case the points of attachment of the substituents R.sup.1 and CV(R.sup.2)-NV'R, respectively; R.sup.1 is a group --(CH.sub.2).sub.b --(A).sub.a --(CH.sub.2).sub.c --B--CH.sub.2 --CO.sub.2 R' in which A and B are each separately oxygen or sulphur, a is 0, b is 0 and c is an integer from 3 to 10, or a is 1, b is 0 or an integer from 1 to 7 and c is an integer from 2 to 9 with the sum of b and c being from 2 to 9, and CO.sub.2 R' is a carboxy group or an amide, ester or salt derivative thereof; V and V' either each separately is hydrogen or together are the second bond of a carbon-nitrogen double bond; R.sup.2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by an aromatic group directly or through an oxygen or sulphur atom; and R is a group --OR.sup.3, --OR.sup.4, --D--R.sup.3, --N.dbd. R.sup.5 or --NW.G.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: December 31, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 5066823
    Abstract: A process for the preparation of 5-acylamino-2,4,6-triiodo or tribromo-benzoic acid derivatives of formula (I), wherein X is I or Br, R is H or a variously substituted alkyl, or a group of formula (II), wherein X has the above meanings; Y is hydroxy, alkoxy, hydroxyalkoxy, alkylamino or hydroxyalkylamino; Z may be the same as COY or it is hydroxylalkylaminocarbonyl provided that at least one of the two acyl or R groups is hydroxy-substituted, which process comprises the rearrangement of the corresponding 5-(alkylaminocarbonyl-alkoxy)-2,4,6-trioodo ro tribromo-benzoic acid derivatives, in the presence of bases.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: November 19, 1991
    Assignee: Bracco Industria Chemica S.p.A.
    Inventors: Ernest Felder, Carlo Musu, Luciano Fumagalli, Fulvio Uggeri
  • Patent number: 5043469
    Abstract: Process for the introduction of functional or functionalizable substituents para to the amino group in 2-aminophenols and 3-aminophenols. The process proceeds in one step, with substitution occurring selectively at the position para to the amino group. Consequently, the reaction is surprisingly straightforward, with very little or no contamination by isomeric by-products. The process comprises reaction of (a) an aminophenol having an open para position to the amino function, with (b) an unhindered non-enolizable aldehyde, and (c) a thiol or sulfinic acid which acts as a nucleophile. In preferred embodiments, the process is conducted at a temperature of from about 50.degree. C. to about 100.degree. C., and in the presence of a polar solvent. The reaction is promoted by an acid having sufficient acidity to protonate the amino group of the aminophenol. Preferably, the acid promoter is a mineral acid, and it is present in an amount at least substantially equivalent to the amount of aminophenol reactant.
    Type: Grant
    Filed: April 13, 1990
    Date of Patent: August 27, 1991
    Assignee: Eastman Kodak Company
    Inventors: Philip T. S. Lau, Danny R. Thompson
  • Patent number: 5034537
    Abstract: This invention relates to (R)-.alpha.-methyl-4-halobenzenemethanamine salts of epimers of acids of the formula ##STR1## and the use of these salts to separate these epimers. These acids are leukotriene antagonists.
    Type: Grant
    Filed: February 8, 1990
    Date of Patent: July 23, 1991
    Assignee: SmithKline Beecham Corporation
    Inventor: James S. Frazee
  • Patent number: 5030653
    Abstract: Certain N-2,6-dialkyl- or N-2,6-dialkoxyphenyl-N'-arylalkylurea compounds are potent inhibitors of the enzyme acyl CoA:cholesterol acyltransferase (ACAT), and are thus useful agents for the treatment of hypercholesterolemia or atherosclerosis.
    Type: Grant
    Filed: October 23, 1990
    Date of Patent: July 9, 1991
    Assignee: Warner-Lambert Company
    Inventor: Bharat K. Trivedi
  • Patent number: 5028256
    Abstract: A composition for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides contains as active ingredient an acylamine derivative of the formula I ##STR1## wherein X is oxygen, sulfur, --SO-- or --SO.sub.2 --,Q is an alkyl, alkenyl, alkinyl group, which may be interrupted by oxygen sulfur sulfonyl or sulfonyl, or a test 1,3-dioxolan-2-yl-alkyl, 1,3-dioxolan-4-alkyl, 2,2-dialkyl-1,3-dioxolan-4-ylalkyl, 1,3-dioxan-2-ylalkyl, 2-benzopyranylalkyl, alkoxycarbonyl alkenyloxycarbonyl or tetrahydrofurylalkyl, or the groupQ--X represents also a halogenoalkyl radical,n is 1, 2 or 3,Z is hydrogen, halogen, alkyl or dioxymethylene, alkoxy, alkenyloxy or alkinyloxy, A is a C.sub.1 -C.sub.8 -hydrocarbon radical which may be straight-chained, branched or cyclic and which is unsubstituted or substituted by alkoxy, alkylthio, cyano or halogen,R is halogenoalkyl or halogenoalkenyl,R.sub.1 is hydrogen, a C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl or C.sub.3 -C.sub.
    Type: Grant
    Filed: December 22, 1988
    Date of Patent: July 2, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Henry Martin
  • Patent number: 5026896
    Abstract: Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4-trisubstituted benzoyl)-1,3-cyclohexanediones are described.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: June 25, 1991
    Assignee: ICI Americas Inc.
    Inventor: William J. Michaely
  • Patent number: 5021430
    Abstract: Disclosed are compound of the formula ##STR1## wherein X and Y independently represent hydroxymethyl; cyano; carboxy; functionally modified carboxy selected from esterified carboxy, carbamoyl, and N-substituted carbamoyl; 5-tetrazolyl; 2-oxazolyl, 4,5-dihydro-2-oxazolyl, or each said grouping substituted by lower alkyl; R and R.sub.o independently represent lower alkyl, (C.sub.3 -C.sub.7)-cycloalkyl-lower alkyl, or aryl-lower alkyl; A represents methylene; or A represents methylene substituted by lower alkyl, by lower alkylthio-lower alkyl, by aryl-lower alkylthio-lower alkyl, by arylthio-lower alkyl, by hydroxy-lower alkyl, by acyloxy-lower alkyl, by lower alkoxy-lower alkyl, by aryl-lower alkyloxy-lower alkyl, by aryloxy-lower alkyl, by amino-lower alkyl, by acylamino-lower alkyl, by guanidino-lower alkyl, by (C.sub.3 -C.sub.7)-cycloalkyl, by (C.sub.3 -C.sub.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: June 4, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Gary M. Ksander
  • Patent number: 5017583
    Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are leukotriene antagonists. These compounds inhibit SRS-A and leukotriene synthesis and are antagonists of SRS-A and are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.
    Type: Grant
    Filed: February 23, 1988
    Date of Patent: May 21, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
  • Patent number: 5013861
    Abstract: Compounds of the formula ##STR1## are disclosed. These compounds are useful as intermediates in the preparation of pharmaceutically active products.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: May 7, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Harold N. Weller, III, Eric M. Gordon
  • Patent number: 5010097
    Abstract: Novel compounds of the formula (I), a process for their preparation and their use as collagenase inhibitors are described: ##STR1## in which, R.sub.1 is hydrogen, alkyl, or optionally substituted aryl;R.sub.2 is hydrogen, or acyl such as ##STR2## where Z is optionally substituted aryl; R.sub.3 is C.sub.3-6 alkyl;R.sub.4 is hydrogen, alkyl, --CH.sub.2 --R.sub.10 where R.sub.10 is optionally substituted phenyl or heteroaryl, or a group ##STR3## where R.sub.11 is hydrogen, alkyl, or --CH.sub.2 --Ph where Ph is optionally substituted phenyl, and R.sub.12 is hydrogen or alkyl; andR.sub.5 is hydrogen, alkyl, or a group ##STR4## where R.sub.13 is hydrogen, or alkyl, and R.sub.14 is hydroxy, alkoxy, or --NR.sub.6 R.sub.7, where each of R.sub.6 and R.sub.7 is hydrogen or alkyl, or R.sub.6 and R.sub.7 together with the nitrogen atom to which they are bonded form a 5-, 6- or 7-membered ring with an optional oxygen or sulphur atom in the ring or an optional further nitrogen atom optionally substituted by alkyl.
    Type: Grant
    Filed: December 20, 1988
    Date of Patent: April 23, 1991
    Assignee: Beecham Pharmaceuticals
    Inventors: Roger E. Markwell, Stephen A. Smith, Ian Hughes, Laramie M. Gaster
  • Patent number: 5002964
    Abstract: The invention relates to novel nitroso compounds having the formula: ##STR1## wherein, R is hydroxy, NH.sub.2, NHR.sup.4, NR.sup.4 R.sup.5 or C.sub.1 -C.sub.7 alkoxy, wherein R.sup.4 and R.sup.5 are C.sub.1 -C.sub.4 alkyl, aryl, or C.sub.1 -C.sub.4 alkyl substituted by aryl;R.sup.1 is hydrogen, C.sub.1 -C.sub.7 alkyl or C.sub.1 -C.sub.7 alkyl substituted by phenyl, amino, guanidino, NHR.sup.6 or NR.sup.6 R.sup.7, wherein R.sup.6 and R.sup.7 are methyl, or C.sub.1 -C.sub.4 acyl;R.sup.3 is hydrogen, C.sub.1 -C.sub.7 alkyl or C.sub.1 -C.sub.7 alkyl substituted by phenyl;n is 0 to 2;A is hydrogen,lower C.sub.1 -C.sub.7 alkyl,lower C.sub.2 -C.sub.7 alkylene,lower C.sub.2 -C.sub.7 alkylene substituted by hydroxy, C.sub.1 -C.sub.4 alkyl, aryl, ora C.sub.4 -C.sub.7 ring which may be fused to a benzene ring;B is hyrogen,lower C.sub.1 -C.sub.7 alkyl,phenyl,lower C.sub.1 -C.sub.7 substituted by phenyl, hydroxy, guanidino, amino, imidazoyl, indolyl, mercapto, mercapto substituted by lower C.sub.1 -C.sub.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: March 26, 1991
    Assignee: Brigham & Women's Hospital
    Inventor: Joseph Loscalzo
  • Patent number: 5001156
    Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 [OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: March 19, 1991
    Assignee: L'Oreal
    Inventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
  • Patent number: 4997980
    Abstract: Disclosed are novel compounds of the formula: ##STR1## wherein: X=--NR.sub.5 R.sub.6, or --OR.sub.7 ;R.sub.1 and R.sub.2 are independently hydrogen, substituted or unsubstituted alkyl, haloalkyl, hydroxyalkyl alkoxyalkyl, alkylaminoalkyl or arylalkyl having up to 18 carbons, cycloalkyl; phenyl or naphthyl; alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituents;R.sub.3 is hydrogen, benzyl, alkoxybenzyl, halobenzyl or alkylbenzyl, provided that if neither R.sub.1 nor R.sub.2 is hydrogen, then R.sub.3 is hydrogen;R.sub.4 is a divalent aromatic group which is substituted or unsubstituted;R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl or phenylalkyl having up to 12 carbons; a cycloalkyl substitutent; phenyl or naphthyl; an alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituent;Furthermore, either R.sub.1 and R.sub.3 or R.sub.1 and R.sub.
    Type: Grant
    Filed: April 17, 1989
    Date of Patent: March 5, 1991
    Assignee: Anitec Image Corporation
    Inventors: Bruce M. Resnick, Allan J. Wexler
  • Patent number: 4994619
    Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.
    Type: Grant
    Filed: June 16, 1988
    Date of Patent: February 19, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
  • Patent number: 4992581
    Abstract: This invention relates to several novel methods of manufacturing thromboxane A.sub.2 inhibiting 7-[3-.alpha.-[1-[[(phenylamino)-thioxomethyl]hydrazono]ethyl]-bicyclo[2.2. 1]-heptenoic acids.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: February 12, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • 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: 4981873
    Abstract: The present invention concerns compounds of the formula: ##STR1## where R.sub.1 is an alkyl or alkenyl radical containing up to 6 carbon atoms, a cycloalkyl radical containing 3 to 7 carbon atoms, an aralkyl, aralkenyl or aryl radical in which the aryl radical or moiety can be substituted one or more times by halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, hydroxyl, trifluoromethyl, cyano, nitro, amino, C.sub.1 -C.sub.6 -alkylamino, C.sub.2 -C.sub.12 -dialkylamino, C.sub.1 -C.sub.6 -acylamino, C.sub.1 -C.sub.16 -acyl, C.sub.1 -C.sub.6 -alkylsulphenyl, -sulphinyl or -sulphonyl or by azido, R.sub.2 is hydrogen atom or a C.sub.1 -C.sub.6 -alkyl, aralkyl, aralkenyl or acyl radical, A and B are saturated or unsaturated alkylene chains containing up to 10 carbon atoms which can be substituted one or more times by C.sub.1 -C.sub.
    Type: Grant
    Filed: June 23, 1989
    Date of Patent: January 1, 1991
    Assignee: Boehringer Mannheim GmbH
    Inventors: Ernst-Christian Witte, Karlheinz Stegmeier, Liesel Doerge, Robert A. Slater
  • Patent number: 4973604
    Abstract: This invention relates to several thromboxane A.sub.2 inhibiting 7-[3-.alpha.-[1-[[(phenylamino)-thioxomethyl]hydrazono]ethyl]-bicyclo[2.2. 1]-heptenoic acids, pharmaceutical compositions employing them and methods of their use.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: November 27, 1990
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 4971994
    Abstract: Novel N-phenyl-N-carbonylthioureas of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.10 alkyl, phenyl-C.sub.1 -C.sub.7 alkyl; C.sub.1 -C.sub.10 alkyl or phenyl-C.sub.1 -C.sub.7 alkyl each of which is monohalogenated or polyhalogenated or interrupted once or more than once by oxygen and/or sulfur; C.sub.3 -C.sub.8 cycloalkyl; C hd 3-C.sub.8 cycloalkyl which is monosubstituted or polysubstituted by halogen or C.sub.1 -C.sub.5 alkyl; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, phenyl, phenyl-C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.8 cycloalkyl; C.sub.1 14 C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl or phenyl-C.sub.1 -C.sub.7 alkyl each of which is monohalogenated or polyhalogenated or interrupted once or more than once by oxygen and/or sulfur; C.sub.3 -C.sub.8 cycloalkyl; phenyl or C.sub.3 -C.sub.8 cycloalkyl each of which is monosubstituted or polysubstituted by halogen or C.
    Type: Grant
    Filed: April 11, 1989
    Date of Patent: November 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Jozef Drabek, Manfred Boger, Josef Ehrenfreund
  • Patent number: 4968829
    Abstract: Substituted phenoxy, phenylthio and anilino compounds, intermediates therefor, synthesis thereof, and their use for the control of pests.
    Type: Grant
    Filed: June 19, 1989
    Date of Patent: November 6, 1990
    Assignee: Sandoz Ltd.
    Inventor: Clive A. Henrick
  • Patent number: RE33574
    Abstract: Novel compounds which are 2,6-di-tertiary-butylphenols substituted in the 4 position by an acylaminophenyl group, which acylaminophenyl group is substituted by a moiety which includes a carboxyl group, are useful as inhibitors of leukotriene biosynthesis and as antiallergic agents.
    Type: Grant
    Filed: January 24, 1990
    Date of Patent: April 23, 1991
    Assignee: Riker Laboratories, Inc.
    Inventors: Alan R. Kirk, Robert A. Scherrer