Polycyclo Ring System Having The Asymmetrical Triazine Ring As One Of The Cyclos Patents (Class 544/183)
  • Patent number: 5863915
    Abstract: Inhibitors for matrix metalloproteases, pharmaceutical compositions containing them, and a process for using them to treat a variety of physiological conditions. The compounds of the invention have the generalized formula ##STR1## wherein R.sup.1 represents C.sub.6 -C.sub.12 alkyl; C.sub.5 -C.sub.12 alkoxy; C.sub.5 -C.sub.12 alkylthio; a polyether of formula R.sup.2 O(C.sub.2 H.sub.4 O).sub.a -- in which a is 1 or 2 and R.sup.2 is C.sub.1 -C.sub.5 alkyl, phenyl, or benzyl; and substituted alkynyl of formula R.sup.3 (CH.sub.2).sub.b --C.tbd.C--; in which b is 1-10 and R.sup.3 is H--, HO--, or R.sup.4 O-- in which R.sup.4 is C.sub.1 -C.sub.3 alkyl, phenyl, or benzyl. The alkyl, phenyl, and benzyl portions of R.sup.1 may bear at least one pharmaceutically-acceptable substituent. The subscript n is 2-4. R.sup.
    Type: Grant
    Filed: May 15, 1997
    Date of Patent: January 26, 1999
    Assignee: Bayer Corporation
    Inventors: Harold C. E. Kluender, Brian R. Dixon, David R. Brittelli
  • Patent number: 5856325
    Abstract: Use of compounds of the formula I ##STR1## in which R.sub.1 signifies an amino, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino or a hydroxyl group, R.sub.2 and R.sub.3, which are the same or different, each hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, cyano, carboxyl, halogen-C.sub.1 -C.sub.6 -alkyl, cyano-C.sub.1 -C.sub.6 -alkyl, carboxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 - alkyl, hydroxyl, carboxy-C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkoxy or aminocarbonyl-C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylaminocarbonyl-C.sub.1 -C.sub.6 -alkoxy or di-C.sub.1 -C.sub.6 -alkylaminocarbonyl-C.sub.1 -C.sub.6 -alkoxy and n the number 0 or 1, their tautomers, as well as salts with non-toxic acids or bases, for the preparation of medicaments with PLA.sub.2 -inhibiting action, new compounds and process for their preparation.
    Type: Grant
    Filed: June 26, 1995
    Date of Patent: January 5, 1999
    Assignee: Boehringer Mannheim GmbH
    Inventors: Walter-Gunar Friebe, Werner Scheuer, Ulrich Tibes
  • Patent number: 5846969
    Abstract: A sulfonamide derivative or a sulfonic ester derivative represented by the following general formula (I): ##STR1## {G represents an aromatic 5- or 6-membered ring; L represents O or --N(R.sup.1)-- (R.sup.1 represents hydrogen or lower alkyl); and M represents ##STR2## rings A and B represent each an unsaturated 5- or 6-membered ring; Y represents O, S(O).sub.n, C(R.sup.3)(R.sup.4), C(O), N(R.sup.5), CH(R.sup.6)CH(R.sup.7), C(R.sup.8).dbd.C(R.sup.9), N(R.sup.10)C(O), N.dbd.C(R.sup.11), OCH(R.sup.12), S(O).sub.n CH(R.sup.13) or N(R.sup.14)CH(R.sup.15).
    Type: Grant
    Filed: June 11, 1997
    Date of Patent: December 8, 1998
    Assignee: Eisai Co., Ltd.
    Inventors: Hiroshi Yoshino, Norihiro Ueda, Jun Niijima, Toru Haneda, Yoshihiko Kotake, Kentaro Yoshimatsu, Tatsuo Watanabe, Takeshi Nagasu, Naoko Tsukahara, Nozomu Koyanagi, Kyosuke Kitoh
  • Patent number: 5786361
    Abstract: Compounds of the formula (I): ##STR1## are prepared by reaction of the phenylacetic acid derivatives substituted by the appropriate heterocycles, optionally in an activated form, with phenylglycinols. The compounds are suitable as active compounds in medicaments, in particular in medicaments having antiatherosclerotic activity.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: July 28, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ulrich Muller, Peter Eckenberg, Rudi Grutzmann, Hilmar Bischoff, Dirk Denzer, Ulrich Nielsch
  • Patent number: 5783576
    Abstract: New compounds of general formula (I) are provided: ##STR1## which are explained in the specification can be prepared by a variety of methods. The compounds may be used in pharmaceutical compositions.
    Type: Grant
    Filed: August 9, 1996
    Date of Patent: July 21, 1998
    Assignee: Boehringer Ingelheim KG
    Inventors: Otto Roos, Georg Speck, Walter Losel, Dietrich Arndts, Wolf-Dietrich Bechtel
  • Patent number: 5750522
    Abstract: This invention provides compounds having the formula ##STR1## wherein R is azacycle or azabicycle;R.sub.1 is alkyl;R.sub.2 and R.sub.3 are each, independently, hydrogen, alkyl, alkoxy, or thioalkyl;n is 0-5;or a pharmaceutically acceptable salt thereof, which are useful in treating symptoms of cholinergic insufficiency involving cognitive disorders.
    Type: Grant
    Filed: July 12, 1996
    Date of Patent: May 12, 1998
    Assignee: American Home Products Corporation
    Inventors: Annmarie Louise Sabb, William A. Kinney
  • Patent number: 5739326
    Abstract: Compounds of Formula I, and their N-oxides and agriculturally-suitable salts, are disclosed which are useful for controlling undesired vegetation ##STR1## wherein: X and Y are independently N or CH;Z is O, S(O).sub.n, NR.sup.7, C(.dbd.O), C(.dbd.S), C(.dbd.N--OR.sup.8), CH(OR.sup.9), or CR.sup.10 (R.sup.11);n is 0, 1 or 2; andR.sup.1 -R.sup.11 are as defined in the disclosure.Also disclosed are compositions containing the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I.
    Type: Grant
    Filed: December 3, 1996
    Date of Patent: April 14, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Thomas Paul Selby, Michael Peter Winters
  • Patent number: 5726126
    Abstract: There is provided a 1-(3-heterocyclylphenyl)-s-triazine-2, 4,6-oxo or thiotrione compound having the structural formula I ##STR1## Further provided are a composition and a method comprising that compound for the control of undesirable plant species.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: March 10, 1998
    Assignee: American Cyanamid Company
    Inventors: Alvin Donald Crews, Jr., Philip Mark Harrington, Gary Mitchell Karp, Mark Christopher Manfredi, Michael Anthony Guaciaro
  • Patent number: 5719151
    Abstract: Phthalazinedione compounds and pharmaceutical compositions are described. The compositions are useful in treating human or animal patients to alleviate or cure disease or disease symptoms caused by nuclear ADP-ribosyl and similar transferases.
    Type: Grant
    Filed: January 13, 1995
    Date of Patent: February 17, 1998
    Inventors: Sydney Shall, Manoochehr Tavassoli
  • Patent number: 5696130
    Abstract: Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 9, 1997
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventors: Todd K. Jones, David T. Winn, Mark E. Goldman, Lawrence G. Hamann, Lin Zhi, Luc J. Farmer, Robert L. Davis
  • Patent number: 5696127
    Abstract: Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 9, 1997
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventors: Todd K. Jones, Lin Zhi, James P. Edwards, Christopher M. Tegley, Sarah J. West
  • Patent number: 5693647
    Abstract: Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 2, 1997
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventors: Todd K. Jones, Lin Zhi, Christopher M. Tegley, David T. Winn, Lawrence G. Hamann, James P. Edwards, Sarah J. West
  • Patent number: 5693646
    Abstract: Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 2, 1997
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventors: Todd K. Jones, Christopher M. Tegley, Lin Zhi, James P. Edwards, Sarah J. West
  • Patent number: 5688808
    Abstract: Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: November 18, 1997
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventors: Todd K. Jones, David T. Winn, Lin Zhi, Lawrence G. Hamann, Christopher M. Tegley, Charlotte L. F. Pooley
  • Patent number: 5672702
    Abstract: Process of producing 3-amino-1,2,4-benzotriazine 1,4-dioxide by reacting benzofurazan-1 oxide with disodiumcyanamide under homogeneous conditions followed by allowing crystallization to occur in a buffered solution. In a preferred embodiment, the process comprises reacting benzofurazan-1 oxide with cyanamide and sodium hydroxide under homogeneous conditions followed by purification in a mixture of acetone and acetic acid.
    Type: Grant
    Filed: December 4, 1995
    Date of Patent: September 30, 1997
    Assignee: Sanofi
    Inventor: Richard E. Philion
  • Patent number: 5670503
    Abstract: New heterocyclic derivatives of the formula: ##STR1## wherein R.sup.1 is aryl which may have suitable substituent(s) or heterocyclic group which may have suitable substituent(s),R.sup.2 is aryl which may have suitable substituent(s) or heterocyclic group which may have suitable substituent(s),R.sup.3 is hydrogen or acyl,R.sup.4 is hydrogen, lower alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl-(lower)alkyl, carboxy(lower)alkyl, protected carboxy(lower)alkyl, ar(lower)alkyl which may have suitable substituent(s), ar(lower)alkenyl, bridged tricyclicalkyl, heterocyclic group which may have suitable substituent(s), acyl, or a group of the formula ##STR2## (in which A is lower alkylene), and R.sup.5 is hydrogen or lower alkyl,and a pharmaceutically acceptable salt thereof which are useful as a medicament.
    Type: Grant
    Filed: August 21, 1995
    Date of Patent: September 23, 1997
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Yoshio Kawai, Hitoshi Yamazaki, Hirokazu Tanaka, Teruo Oku
  • Patent number: 5658906
    Abstract: The present invention is directed to irreversible inhibitors of serine and cysteine proteases which most preferably contain a 1-oxytriazole or 1-oxyimidazole functionality. Methods for the use of the protease inhibitors are also described.
    Type: Grant
    Filed: January 26, 1996
    Date of Patent: August 19, 1997
    Assignee: Cephalon, Inc.
    Inventors: John P. Mallamo, Ron Bihovsky, Sankar Chatterjee, Rabindranath Tripathy
  • Patent number: 5633218
    Abstract: Compounds of Formula I, and their N-oxides and agriculturally-suitable salts, are disclosed which are useful for controlling undesired vegetation ##STR1## wherein: ##STR2## T is O or S; W is a single bond, O, S or NR.sup.6 ;X is N or CH;Y is N or CH;Z is N or CR.sup.7 provided that when Z is CR.sup.7, then Y is N;R.sup.6 is H, CH.sub.3 or OCH.sub.3 ;m is 1 or 2; andR.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.7 are as defined in the disclosure.Also disclosed are compositions containing the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: May 27, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Donna L. Spedding, Thomas M. Stevenson
  • Patent number: 5631253
    Abstract: Compounds having the formula (I): ##STR1## and stereoisomers thereof, wherein A is hydrogen, halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclylalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryloxy, optionally substituted heteroaryloxy, nitro, halo, cyano, --NR.sup.3 R.sup.4, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --S(O).sub.n R.sup.3 wherein n is 0, 1 or 2, (CH.sub.2).sub.m PO(OR.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: May 20, 1997
    Assignee: Zeneca Limited
    Inventors: Paul J. de Fraine, Anne Martin
  • Patent number: 5616537
    Abstract: A condensed heterocyclic derivative of the formula (I): ##STR1## (wherein R is a hydroxyl group, R.sup.3 or R.sup.4 is an alkoxy group, W is an oxygen atom, Yn is a hydrogen atom, Z is a methine group, and A is a 5- or 6-membered heterocyclic ring which may be substituted, and a herbicide, are presented. When used for paddy field treatment, upland soil treatment and foliage treatment, the condensed heterocyclic derivative of the present invention exhibits excellent herbicidal activities against gramineous and non-gramineous weeds without adversely affecting crop plants.
    Type: Grant
    Filed: March 1, 1994
    Date of Patent: April 1, 1997
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Sumio Yokota, Masafumi Matsuzawa, Nobuyuki Ohba, Toshihiro Nagata, Shigehiko Tachikawa, Takeshige Miyazawa, Katsutada Yanagisawa
  • Patent number: 5610157
    Abstract: N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives, their N-oxide forms and pharmaceutically acceptable salts having gastrointestinal motility stimulating properties, compositions containing these compounds as active ingredient and methods of treating warm-blooded animals suffering from the decreased peristalsis of the gastrointestinal system.
    Type: Grant
    Filed: April 13, 1995
    Date of Patent: March 11, 1997
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Georges H. P. Van Daele, Frans M. A. Van den Keybus
  • Patent number: 5565472
    Abstract: Compounds of the formula ##STR1## the pharmaceutically acceptable salts thereof wherein R.sup.2, R.sup.3, R.sup.4, m, X and Q are as defined below, and novel intermediates used in the synthesis of such compounds. The compounds of formula I are inhibitors of acyl coenzyme A: cholesterol acyltransferase (ACAT) and are useful as hypolipidemic and antiatherosclerosis agents.
    Type: Grant
    Filed: October 18, 1994
    Date of Patent: October 15, 1996
    Assignee: Pfizer Inc.
    Inventor: Ernest S. Hamanaka
  • Patent number: 5523379
    Abstract: A high molecular weight stabilizer compound formed as an ester of 3-(2H-benzotriazol-2-yl)-5-(1,1-dimethylethyl)-4-hydroxy-benzene-propanoic acid, or structural variants thereof, to impart improved resistance to the effects of ultraviolet radiation to polycarbonate comprising polymers, a process for the preparation of said compound, and articles of manufacture comprising said compound.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: June 4, 1996
    Assignee: General Electric Plastics
    Inventor: Niles R. Rosenquist
  • Patent number: 5519022
    Abstract: The invention concerns .alpha.,.alpha.-dialkylbenzyl derivatives of the formula I ##STR1## wherein Ar.sup.1 is phenyl or naphthyl, or a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;the phenylene group may optionally bear one or two substituents R.sup.3 ;each of R.sup.1 and R.sup.2, which may be the same or different is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, fluoro-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, provided that both of R.sup.1 and R.sup.2 are not methyl or fluoromethyl; andQ is cyano, amino, nitro, formyl, (1-4C)alkoxy, thiazolyl or (2-4C)alkanoyl;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.
    Type: Grant
    Filed: November 10, 1993
    Date of Patent: May 21, 1996
    Assignees: Imperial Chemical Industries Plc, ICI Pharma
    Inventors: Philip N. Edwards, David Waterson
  • Patent number: 5514795
    Abstract: The present invention relates to a process for the preparation of aminotriazine derivatives of the formula I ##STR1## by the solvolysis of compounds of the formula II ##STR2## in the presence of gaseous hydrogen chloride in an alcoholic medium. The compounds of formula I are useful as intermediates in the manufacture of insecticides.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 7, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Thomas Rapold, Marcel Senn
  • Patent number: 5498616
    Abstract: The present invention is directed to irreversible inhibitors of serine and cysteine proteases which most preferably contain a 1-oxytriazole or 1-oxyimidazole functionality. Methods for the use of the protease inhibitors are also described.
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: March 12, 1996
    Assignee: Cephalon, Inc.
    Inventors: John P. Mallamo, Ron Bihovsky, Sankar Chatterjee, Rabindranath Tripathy
  • Patent number: 5491126
    Abstract: This invention relates to substituted fused heterocyclic compounds of Formula I which have utility as herbicides: ##STR1##
    Type: Grant
    Filed: October 19, 1994
    Date of Patent: February 13, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Thomas P. Selby
  • Patent number: 5484918
    Abstract: A process for the preparation of an aqueous medium of nicotinaldehyde by the catalytic reduction of 3-cyanopyridine under hydrogen in the presence of Raney-nickel.
    Type: Grant
    Filed: February 9, 1994
    Date of Patent: January 16, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Urs Siegrist, Henry Szczepanski
  • Patent number: 5405843
    Abstract: Heterocyclic compounds useful as anticancer drug potentiaters having a potentiating effect on the incorporation of anticancer drugs into cancer cells are disclosed, the compounds each synthesized by, for example, reacting a epoxy compound obtained by reacting a heterocyclic compound with an epihalogenohydrin, with an amine derivative.
    Type: Grant
    Filed: September 9, 1993
    Date of Patent: April 11, 1995
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Nobuyuki Fukazawa, Makoto Odate, Tsuneji Suzuki, Kengo Otsuka, Takashi Tsuruo, Wakao Sato
  • Patent number: 5399560
    Abstract: The mechanism of the inhibition of advanced glycosylation by aminoguanidine and other hydrazine type compounds was investigated using a solution of one or two molecules of aminoguanidine or other hydrazine type compound incubated with an Amadori product (1-propylamine-1-deoxy-D-fructose) under physiological conditions. This inhibition was found to proceed through the reactive intermediate 1-propylamino-1, 4-dideoxyosone to form the corresponding triazine and the dehydrazone of 1,4-dideoxyglucosone, respectively.The triazine and dehydrazone products are useful as macrophage stimulants to activate a macrophage to effect removal of advanced glycosylation endproducts (AGEs). Additionally, they can be used in a variety of investigative methods in an effort to measure the extent of nonenzymatic glycosylation of a protein sample wherein aminoguanidine or other hydrazine-type compound is or was present during the glycosylation process.
    Type: Grant
    Filed: October 1, 1992
    Date of Patent: March 21, 1995
    Assignee: The Rockefeller University
    Inventors: Anthony Cerami, Hauh-Jyun C. Chen
  • Patent number: 5384403
    Abstract: The present invention relates to a process for the preparation of aminotriazine derivatives of the formula I ##STR1## by the solvolysis of compounds of the formula II ##STR2## in the presence of gaseous hydrogen chloride in an alcoholic medium. The compounds of formula I are useful as intermediates in the manufacture of insecticides.
    Type: Grant
    Filed: February 9, 1994
    Date of Patent: January 24, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Thomas Rapold, Marcel Senn
  • Patent number: 5324833
    Abstract: Compounds of the formula I, ##STR1## in which 'R.sub.1 is an amino protective group, and n stands for 1 or 2, R.sub.1 denotes hydrogen or an amino protective group, R.sub.2 denotes hydrogen or a carboxyl protective group and R.sub.3 denotes triphenylmethyl, 4-monomethoxy-trityl or 4,4'-dimethoxy-trityl, and reactive carboxylic acid derivatives of such compounds of the formula I in which R.sub.2 stands for hydrogen, are described.These compounds can be used as starting materials for the preparation of peptides. They are more suitable for this than are analogous compounds of the formula I in which R.sub.3 denotes hydrogen or one of the carbamoyl protective groups hitherto customary.
    Type: Grant
    Filed: April 13, 1990
    Date of Patent: June 28, 1994
    Assignee: Novabiochem AG
    Inventors: Peter Sieber, Bernhard Riniker
  • Patent number: 5304556
    Abstract: Benzamide derivatives of the following formula (I) ##STR1## [wherein R.sup.1 : ##STR2## B, D: hydrogen atom, etc. E: pyridyl group, etc.n: integer from 0 to 2R.sup.2 : R.sup.3 R.sup.4 N-- etc.(R.sup.3,R.sup.4 : optionally substituted C.sub.6 -C.sub.14 aryl group, etc.)A; ##STR3## --CH.sub.2 --, --N.dbd.N--, --CH.dbd.N--, --N.dbd.CH--, --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --].Optical antipodes thereof or pharmaceutically acceptable salts thereof, show excellent PAF antagonism and are effective for therapy and prophylaxis of diseases caused by PAF (bronchial asthma, nephritis, shocks, cardiac infarction, cerebral hemorrhage, ulcer, DIC, autoimmune diseases, thrombosis, etc.).
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: April 19, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Akihiro Yamamoto, Shuji Morita, Yoshio Hayashi, Noboru Yamada, Toshihito Kitamura
  • Patent number: 5280009
    Abstract: Pyrimidine derivatives of the Formula Ia or Ib ##STR1## where the substituents have the following meanings: R.sup.1 is hydrogen or alkyl;A is a substituted or unsubstituted bi- or tricyclic carbo- or heterocyclic radical which may contain one or several double bonds;R.sup.5 is H or alkyl;X is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or haloalkylthio; and addition salts thereof with organic or inorganic acids and the use of said pyrimidine derivative to control undesirable plant growth.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: January 18, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Hamprecht, Klaus Ditrich, Karl-Otto Westphalen, Matthias Gerber, Helmut Walter
  • Patent number: 5262418
    Abstract: Piperidine derivatives of formula ##STR1## wherein A is a radical of formula--CH.sub.2 --CH.sub.2 -- (a-1),--CH.sub.2 --CH.sub.2 --CH.sub.2 -- (a-2), or--CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 -- (a-3),wherein one or two hydrogen atoms in said radicals (a-1) to (a-3) may be replaced by a C.sub.1-6 alkyl radical;R.sup.1 is hydrogen or halo; R.sup.2 is hydrogen, amino, mono or di(C.sub.1-6 alkyl)amino or C.sub.1-6 alkylcarbonylamino; R.sup.3 is hydrogen or C.sub.1-6 alkyl; L is C.sub.3-6 cycloalkyl, C.sub.5-6 cycloalkanone, C.sub.3-6 alkenyl optionally substituted with aryl, or L is a radical of formula--Alk--R.sup.4 (b-1),--Alk--X--R.sup.5 (b-2),--Alk--Y--C(.dbd.O)--R.sup.7 (b-3), or--Alk--Y--C(.dbd.O)--NR.sup.9 R.sup.10 (b-4),the N-oxide forms, addition salts and stereochemically isomeric forms thereof, said compounds having gastrointestinal motility stimulating properties.
    Type: Grant
    Filed: November 17, 1992
    Date of Patent: November 16, 1993
    Assignee: Tanssen Pharmaceutica N.V.
    Inventors: Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Michel A. J. De Cleyn
  • Patent number: 5240938
    Abstract: Substituted heterocycles attached through a methylene bridge to novel substituted phenyl derivatives of the Formula I are useful as angiotensin II antagonists.
    Type: Grant
    Filed: August 13, 1991
    Date of Patent: August 31, 1993
    Assignee: Merck & Co., Inc.
    Inventors: William J. Greenlee, Arthur A. Patchett, David Hangauer, Thomas F. Walsh, Kenneth J. Fitch, Ralph A. Rivero, Daljit S. Dhanoa
  • Patent number: 5234925
    Abstract: 2-Aza-2-desamino analogues of 5,8-dideazafolic acid, which analogues have the formula ##STR1## wherein X is an aryl or heteroaryl moiety;R.sup.1 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, or C.sub.3 -C.sub.4 alkynyl; andR.sup.2 is OH, an L-.alpha.-amino acid, or a peptide comprising L-.alpha.-amino acids.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: August 10, 1993
    Assignee: Dana-Farber Cancer Institute, Inc.
    Inventor: Andre Rosowsky
  • Patent number: 5185335
    Abstract: Piperidine derivatives of formula ##STR1## wherein A is a radical of formula ##STR2## wherein one or two hydrogen atoms in said radicals (a-1) to (a-3) may be replaced by a C.sub.1-6 alkyl radical;R.sup.1 is hydrogen or halo; R.sup.2 is hydrogen, amino, mono or di(C.sub.1-6 alkyl)amino or C.sub.1-6 alkylcarbonylamino; R.sup.3 is hydrogen or C.sub.1-6 alkyl; L is C.sub.3-6 cycloalkyl, C.sub.5-6 cycloalkanone, C.sub.3-6 alkenyl optionally substituted with aryl, or L is a radical of formula ##STR3## the N-oxide forms, addition salts and stereochemically isomeric forms thereof, said compounds having gastrointestinal motility stimulating properties. Pharmaceutical compositions containing these compounds as active ingredient, and a method of preparing said compounds and pharmaceutical compositions.
    Type: Grant
    Filed: February 4, 1991
    Date of Patent: February 9, 1993
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Michel A. J. De Cleyn
  • Patent number: 5175287
    Abstract: A method of using 1,2,4-benzotriazine oxides, some of which are novel compounds, as radiosensitizers and selective cytotoxic agents is disclosed. These compounds are shown to specifically radiosensitize hypoxic tumor cells. Some are additionally disclosed to be useful as specific cytotoxic agents for these cells. They also show an unexpected ability to radiosensitize aerobic cells following or preceding a hypoxic incubation of the cells with the drug. This provides a basis for selective radiosensitization of tumors compared to normal cells. A novel method for preparing the 1,2,4-benzotriazine oxides is also disclosed.
    Type: Grant
    Filed: September 18, 1989
    Date of Patent: December 29, 1992
    Assignee: S R I International
    Inventors: William W. Lee, J. Martin Brown, Edward W. Grange, Abelardo P. Martinez, Michael Tracy, Daniel J. Pollart
  • Patent number: 5151427
    Abstract: Novel anthelmintics are described which, as active ingredient, contain a compound of the formula I ##STR1## or in its hydrogenated form the formula (Ia) ##STR2## in which R.sub.1 and R.sub.2 independently of one another are C.sub.1 -C.sub.6 alkyl, allyl, C.sub.3 -C.sub.6 cycloalkyl, benzyl or phenyl; R.sub.3 is an unsubstituted or substituted heteroaromatic 6-membered ring which contains 1, 2 or 3 nitrogen atoms or a benzo-fused, unsubstituted or substituted heteroaromatic 6-membered ring which contains 1 to 3 nitrogen atoms, and R.sub.4 and R.sub.5 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogeno-C.sub.1 -C.sub.3 alkyl, including their tautomeric forms and physiologically tolerable salts. The preparation, formulation and use of these active ingredients are also described.
    Type: Grant
    Filed: November 28, 1990
    Date of Patent: September 29, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Louis-Pierre Molleyres
  • Patent number: 5126343
    Abstract: A compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein n is 0 or 1; andAr is an aromatic amide moiety, which compound exhibits prokinetic activity and is a 5-HT3 antagonist.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: June 30, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Daniel L. Zabrowski, Daniel L. Flynn
  • Patent number: 5114938
    Abstract: For controlling parasitic protozoa and fish parasites, the novel substituted hexahydro-1,2,4-triazinediones of the formula ##STR1## in which R.sup.1 represents a heteroaromatic radical which is bonded via carbon and is optionally substituted,X represents O, S, SO, SO.sub.2 or --CR.sup.5 (CN)--,R.sup.2 represents one or more identical or different radicals from the group consisting of hydrogen, halogen, nitro, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, alkylthio and halogenoalkylthio,R.sup.3 and R.sup.4, independently of one another, represent hydrogen, optionally substituted alkyl, alkenyl, alkinyl or aralkyl, andR.sup.5 represents hydrogen or alkyl, excepting compounds in which X represents --CR.sup.5 (CN)--andR.sup.1 represents thienyl.
    Type: Grant
    Filed: January 2, 1990
    Date of Patent: May 19, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Lindner, Axel Haberkorn
  • Patent number: 5112817
    Abstract: Novel heterocyclic compounds, which are represented by the following general formula, useful as anticancer drug potentiaters having a potentiating effect on the incorporation of anticancer drugs into cancer cells, the compounds each synthesized by, for example, reacting a epoxy compound obtained by reacting a heterocyclic compound with an epihalogenohydrin, with an amine derivative.
    Type: Grant
    Filed: October 6, 1992
    Date of Patent: May 12, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Nobuyuki Fukazawa, Makoto Odate, Tsuneji Suzuki, Kengo Otsuka, Takashi Tsuruo, Wakao Sato
  • Patent number: 5110347
    Abstract: The invention relates to certain substituted fused compounds of Formula I ##STR1## which are useful as herbicides, and their agriculturally suitable compositions, as well as methods for their use as general or selective preemergent or postemergent herbicides or as plant growth regulants.
    Type: Grant
    Filed: November 26, 1990
    Date of Patent: May 5, 1992
    Assignee: E. I Du Pont de Nemours and Company
    Inventor: Thomas Selby
  • Patent number: 5021478
    Abstract: Compounds containing both a UV-absorbing moiety and a 1-hydrocarbyloxy hindered amine moiety are effective stabilizers for protecting polymer compositions against the deleterious effects of actinic light. The UV-absorbing moieties include the substituted 2H-benzotriazoles, s-triazines, acrylates, benzophenones, oxanilides and oxamides.
    Type: Grant
    Filed: February 14, 1990
    Date of Patent: June 4, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Ramanathan Ravichandran, James P. Galbo
  • Patent number: 4994448
    Abstract: The new compounds of the general Formula I ##STR1## (wherein R.sub.1 stands for C.sub.1-4 alkyl or aralkyl; andR.sub.2 represents hydroxy; orR.sub.1 and R.sub.2 together form a valency bond;R.sub.3 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, amino, alkylthio or a group of the Formula --NR.sub.7 R.sub.8 in which R.sub.7 and R.sub.8 may be the same or different and stand for hydrogen, C.sub.1-4 alkyl, phenyl-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkyl or di-(C.sub.1-4 alkyl)-amino-C.sub.1-4 alkyl or together with the nitrogen atom they are attached to form a 6-membered heterocyclic ring which may optionally contain a further nitrogen, oxygen or sulfur atom; orR.sub.2 and R.sub.3 together form an oxo (.dbd.O) or thixo (.dbd.S) group;R.sub.4 represents hydrogen, C.sub.1-4 alkyl or phenyl which may optionally bear one or two halogen or nitro substituent(s);Z is a group of the Formula (a) or (b) ##STR2## A.sup.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: February 19, 1991
    Assignee: Egis Gyogyszergyar
    Inventors: Andras Messmer, Gyorgy Hajos, Zsuzsa Juhasz nee Riedl, Pal Benko, Laszlo Pallos, Lujza Petocz, Eniko Szirt nee Kiszelly, Gabor Gigler, Istvan Gyertyan, Maria Hegedus
  • Patent number: 4959367
    Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein X is N or CH;R.sub.1 and R.sub.2 are the same or different and are hydrogen, halogen, CF.sub.3, C.sub.1-6 alkyl, C.sub.1-7 acyl, C.sub.1-7 acylamino, or amino, aminocarbonyl or aminosulphonyl, optionally substituted by one or two C.sub.1-6 alkyl or C.sub.3-8 cycloalkyl groups, or by C.sub.4-5 polymethylene or by phenyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkylsuphinyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, hydroxy or nitro; or R.sub.1 and R.sub.2 taken together are methylenedioxy or ethylenedioxy;Z is a group of formula (a), (b) or (c) ##STR2## wherein n is 2 or 3; p is 1 or 2; q is 1 to 3; r is 1 to 3; andR.sub.3 or R.sub.4 is C.sub.1-4 alkyl;having 5-HT.sub.3 receptor antagonist activity, a process for their preparation and their use as pharmaceuticals.
    Type: Grant
    Filed: November 2, 1988
    Date of Patent: September 25, 1990
    Assignee: Beecham Group P.L.C.
    Inventor: Francis D. King
  • Patent number: 4939251
    Abstract: Novel 1-azaspiro[4.4] lactams are produced by reaction of at least one hydroxy-containing primary amino compound with a 4-ketodiacid compound or a 1,6-dioxaspiro[4.4]lactone. Molar excesses of amion compound result in production of spirodilactams, while limited molar quantities of amino compound results in production of a spirolactam-lactone which reacts further with hydroxy-containing primary amino compound or with hydroxy-free primary amino compound to produce a spirodilactam. Certain of the spirolactams are useful as precursors for glycidyloxy derivatives which react with epoxy curing agents to form insoluble thermoset resins while others are useful as curing agents and yet others are converted to glycidyloxy derivatives useful as reactive diluents in epoxy resin applications.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: July 3, 1990
    Assignee: Shell Oil Company
    Inventor: Pen C. Wang
  • Patent number: 4931438
    Abstract: This invention relates to derivatives of acrylic acid useful as fungicides, to processes for preparing them, to fungicidal compositions containing them, and to methods of using them to combat fungi, especially fungal infections in plants.
    Type: Grant
    Filed: June 22, 1989
    Date of Patent: June 5, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey
  • Patent number: 4931439
    Abstract: Novel substituted N-amino-1,2,4-triazinones of formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.2 haloalkyl, phenyl, benzyl, phenethyl, phenproptyl, phenbutyl or phenpentyl, or a phenyl, benzyl, phenethyl, phenpropyl, phenbutyl or phenpentyl radical that is mono- or di-substituted by halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.2 haloalkyl, methoxy and/or by ethoxy,R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, or is phenyl that is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, halogen or by C.sub.1 -C.sub.12 haloalkyl, or R.sub.1 and R.sub.2 together form a saturated or unsaturated 3- to 7-membered carbocycle,R.sub.3 is hydrogen or C.sub.1 -C.sub.6 alkyl andZ is --N.dbd.CH-- or --NH--CH.sub.
    Type: Grant
    Filed: October 11, 1988
    Date of Patent: June 5, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Haukur Kristinsson