Pteridines (including Hydrogenated) Patents (Class 544/257)
  • Patent number: 5807854
    Abstract: Compounds of general formula I and their salts and solvates are antifungal agents and as such are useful in the treatment of various fungal infections. Pharmaceutical compositions including these compounds and processes for their preparation are also provided.
    Type: Grant
    Filed: March 31, 1997
    Date of Patent: September 15, 1998
    Assignee: J. Uriah & Cia. S.A.
    Inventors: Javier Bartroli, Enric Turmo, Manuel Anguita
  • Patent number: 5792767
    Abstract: The present invention relates to a compound of the formula ##STR1## and the pharmaceutically acceptable salts thereof wherein W is a bicyclic heterocyclic ring system. The compounds are .alpha.-1 adrenergic antagonists and are useful in the treatment of BPH; also disclosed are .alpha.-1 antagonist compositions and a method for antagonizing .alpha.-1 receptors and treating BPH.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: August 11, 1998
    Assignee: Abbott Laboratories
    Inventors: Michael D. Meyer, Robert J. Altenbach, Fatima Z. Basha, William A. Carroll, Irene Drizin, James F. Kerwin, Jr., Suzanne A. Lebold, Edmund L. Lee, John K. Pratt, Kevin B. Sippy, Karin R. Tietje, Diane M. Yamamoto
  • Patent number: 5777117
    Abstract: Disclosed is a process for preparing compounds having a straight or branched aliphatic hydrocarbon structure of formula I: ##STR1## In formula I, n is an integer from one to four and m is an integer from four to twenty. Independently, R.sub.1 and R.sub.2 are hydrogen, a straight or branched chain alkyl, alkenyl or alkynyl of up to twenty carbon atoms in length or --(CH.sub.2).sub.w R.sub.5. If R.sub.1 or R.sub.2 is --(CH.sub.2).sub.w R.sub.5, w may be an integer from one to twenty and R.sub.5 may be an hydroxyl, halo, C.sub.1-8 alkoxyl group or a substituted or unsubstituted carbocycle or heterocycle. Alternatively, R.sub.1 and R.sub.2 may jointly form a substituted or unsubstituted, saturated or unsaturated heterocycle having from four to eight carbon atoms, N being a hetero atom of the resulting heterocyle. R.sub.3 may be either hydrogen or C.sub.1-3. In the compounds, a total sum of carbon atoms comprising R.sub.1 or R.sub.2, (CH.sub.2).sub.n and (CH.sub.2).sub.m does not exceed forty. R.sub.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 7, 1998
    Assignee: Cell Therapeutics, Inc.
    Inventors: J. Peter Klein, Gail E. Underiner, Anil M. Kumar
  • Patent number: 5756502
    Abstract: Novel quinazolinone derivatives with good binding affinity for the CCK-A and CCK-B receptors, pharmaceutical compositions containing them, methods of using them and a novel process for their preparation are taught. The compounds are useful agents to suppress appetite, reduce gastric acid secretion, and the like.
    Type: Grant
    Filed: July 10, 1995
    Date of Patent: May 26, 1998
    Assignee: Warner-Lambert Company
    Inventor: Janak Khimchand Padia
  • Patent number: 5703235
    Abstract: Disclosed are compounds of the formula: ##STR1## or the pharmaceutically acceptable acid addition salts thereof, wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are the same or different and represent hydrogen, C.sub.1 -C.sub.6 alkyl, halogen, hydroxy, amino, cyano, nitro, trifluoromethyl, trifluoromethoxy, C.sub.1 -C.sub.6 alkoxy, --O.sub.2 CR', --NHCOR', --COR', --SO.sub.m R', where R' is C.sub.1 -C.sub.6 alkyl and wherein m is 0, 1 or 2; orR.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 independently represent --CONR'R", or --NR'R" where R' and R" independently represent hydrogen or C.sub.1 -C.sub.6 alkyl;R.sub.10 is hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: March 21, 1996
    Date of Patent: December 30, 1997
    Assignee: Neurogen Corporation
    Inventors: Jun Yuan, Xi Chen
  • Patent number: 5696264
    Abstract: Disclosed are novel folic acid-alkaline phosphatase conjugates useful in a competitive immunoassay for folic acid in a biological fluid such as serum. A preferred conjugate involves a folate hapten bound to (N-Succinimidyl?4-iodoacetyl!aminobenzoate) through a 1,12-diamino-4,9-dioxadodecanyl spacer arm.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: December 9, 1997
    Assignee: Bayer Corporation
    Inventors: James P. Albarella, Linda M. Anderson-Mauser, Frank Thomas Hartl, Gary M. Johnson
  • Patent number: 5693641
    Abstract: This invention is directed to bicyclic pyrimidine derivatives which are useful as anti-coagulants. This invention is also directed to pharmaceutical compositions containing the compounds of the invention, and methods of using the compounds to treat disease-states characterized by thrombotic activity.
    Type: Grant
    Filed: August 16, 1996
    Date of Patent: December 2, 1997
    Assignee: Berlex Laboratories Inc.
    Inventors: Brad O. Buckman, Raju Mohan, Michael M. Morrissey
  • Patent number: 5665719
    Abstract: Compounds of the formula ##STR1## X is --O--, --NH-- and --NR.sup.8 --; Y is --CH.sub.2 --, --CHR.sup.8 -- and --C(R.sup.8).sub.2 --; R.sup.1 is camphor-10-yl, C.sub.1-5 alkoxyl, styryl, hydroxystyryl, furyl, unsubstituted or substituted thienyl, naphthyl, indolyl, tetrahydronaphthyl, unsubstituted, mono- or di-substituted pyridyl, pyrazinyl, unsubstituted or substituted cyclohexyl where the substituent is R.sup.4, and unsubstituted or substituted phenyl where the substituents on phenyl are R.sup.5, R.sup.6 and R.sup.7 ; R.sup.2 is hydrogen, C.sub.1-5 alkoxy, C.sub.1-5 alkyl, amino, C.sub.1-5 alkylcarbonylamino, nitro or halogen; R.sup.3 is hydrogen, C.sub.1-5 alkoxycarbonyl, cyano or carbamoyl; R.sup.4 is one to two of hydrogen, oxo, hydroxy, C.sub.1-5 alkoxy, C.sub.1-5 alkoxycarbonylamino-C.sub.1-5 alkyl and amino-C.sub.1-5 alkyl; R.sup.5, R.sup.6 are each independently selected from hydrogen, halogen, C.sub.1-5 alkyl, hydroxyl and C.sub.1-5 alkoxy; R.sup.7 is ##STR2## W is CO or SO.sub.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: September 9, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Mark G. Bock, Ben E. Evans, Peter D. Williams, Roger M. Freidinger, Douglas J. Pettibone, Doug W. Hobbs, Paul S. Anderson
  • Patent number: 5641783
    Abstract: Disclosed are compounds having a straight or branched aliphatic hydrocarbon structure of formula I: ##STR1## In formula I, n is an integer from one to four and m is an integer from four to twenty. Independently, R.sub.1 and R.sub.2 are hydrogen, a straight or branched chain alkyl, alkenyl or alkynyl of up to twenty carbon atoms in length or --(CH.sub.2).sub.w R.sub.5. If R.sub.1 or R.sub.2 is --(CH.sub.2).sub.w R.sub.5, w may be an integer from one to twenty and R.sub.5 may be an hydroxyl, halo, C.sub.1-8 alkoxyl group or a substituted or unsubstituted carbocycle or heterocycle. Alternatively, R.sub.1 and R.sub.2 may jointly form a substituted or unsubstituted, saturated or unsaturated heterocycle having from four to eight carbon atoms, N being a hetero atom of the resulting heterocycle. R.sub.3 may be either hydrogen or C.sub.1-3. In the compounds, a total sum of carbon atoms comprising R.sub.1 or R.sub.2, (CH.sub.2).sub.n and (CH.sub.2).sub.m does not exceed forty. R.sub.
    Type: Grant
    Filed: September 8, 1994
    Date of Patent: June 24, 1997
    Assignee: Cell Therapeutics, Inc.
    Inventors: J. Peter Klein, Gail E. Underiner, Anil M. Kumar
  • Patent number: 5620978
    Abstract: Disclosed is a method of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma or hypoglycemia. The method comprises administering to an animal a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof; wherein n is zero or 1; R.sup.4, R.sup.5, R.sup.6 are independently hydrogen, nitro, amino, halo, haloalkyl, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, azido, acylamino, alkylsulfonyl, aryl, substituted aryl, heteroaryl, alkoxy, trialkylsilyl-substituted alkoxy, aryloxy, substituted aryloxy, heteroaryloxy, a heterocyclic group, a heterocyclicoxy group, aralkoxy, or haloalkoxy; and R.sup.c and R.sup.d are defined in the specification. These compounds have high binding to the glycine site of the NMDA receptor.
    Type: Grant
    Filed: January 3, 1995
    Date of Patent: April 15, 1997
    Assignees: State of Oregon, acting by and through The Oregon State Board of Higher Education, acting for and on behalf of The Oregon Health Sciences University and The University of Oregon, Eugene Oregon, The Regents of the University of California, ACEA Pharmaceuticals, Inc.
    Inventors: Sui X. Cai, John F. W. Keana, Eckard Weber
  • Patent number: 5606017
    Abstract: Provided are drug/ligand compounds of Formula (I): ##STR1## in which D is a drug moiety;n is an integer from 1 to 10;p is an integer from 1 to 6;Y is O or NH.sub.2.sup.+ Cl.sup.- ;z is 0 or 1;q is about 1 to about 10;X is a ligand; and,A is a Michael Addition Adduct.In a preferred embodiment, the ligand is an immunoglobulin, preferably a chimeric antibody or fragment thereof. Also provided are formulations comprising as an active ingredient a compound of Formula (I), intermediates useful for preparing the compounds of Formula (I), processes for preparing the compounds of Formula (I), and methods for using the compounds of the invention.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: February 25, 1997
    Assignee: Bristol-Myers Squibb Company
    Inventors: David Willner, Pamela A. Trail, H. Dalton King, Sandra J. Hofstead, Robert S. Greenfield, Gary R. Braslawsky
  • Patent number: 5595992
    Abstract: Substituted pyridines and pyrimidines, processes for their preparation and their use as pesticides and fungicides.The invention relates to compounds of the formula ##STR1## in which A is N or CH, R is H, halogen, alkyl or cycloalkyl, R.sup.2 and R.sup.3 are H, halogen or an aliphatic radical or together form a ring, X is O, NH Or S(O).sub.q where q=0, 1 or 2, R.sup.4.sub.q is 0-4 radicals selected from the series consisting of halogen, optionally substituted alkyl or alkoxy, cycloalkyl and optionally substituted phenyl, n=0-2, m=1-3 and Y is optionally substituted methylene or imino.The invention furthermore relates to a process for their preparation and for their use as pesticides, in particular as insecticides, acaricides and fungicides. The compounds are furthermore suitable for controlling nematodes, helminths and molluscs, and for controlling endoparasites and ectoparasites in the field of veterinary medicine.
    Type: Grant
    Filed: September 12, 1994
    Date of Patent: January 21, 1997
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventors: Rainer Preuss, Wolfgang Schaper, Martin M arkl, Harald Jakobi, Peter Braun, Werner Knauf, Burkhard Sachse, Anna Waltersdorfer, Manfred Kern, Peter L ummen, Werner Bonin
  • Patent number: 5571811
    Abstract: The invention is concerned with the compounds having the formula ##STR1## the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein Y is CH or N; R.sup.1, R.sup.2 and R.sup.3 each independently are hydrogen or C.sub.1-4 alkyl; R.sup.4 and R.sup.5 each independently are hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkyloxy, hydroxy, trifluoromethyl, trifluoromethyloxy or difluoromethyloxy; R.sup.6 is C.sub.1-4 alkyl; or phenyl optionally substituted with halo, C.sub.1-4 alkylcarbonylamino, C.sub.1-4 alkyloxy, C.sub.1-4 alkyl or nitro; Z is C.dbd.O or CHOH; and ##STR2## is a radical of formula ##STR3## Compositions comprising said compounds, processes for preparing the same and the use of these compounds as a method of treating Helicobacter infection.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: November 5, 1996
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Jan Heeres, Raymond A. Stokbroekx, Joseph H. Mostmans, Louis J. E. Van der Veken
  • Patent number: 5556858
    Abstract: Heteroarylpiperidines, pyrrolidines, and piperazines are useful as antipsychotic and analgesic agents the compounds are especially useful for treating psychoses by administering to a mammal a psychoses-treating effective amount of one of the compounds. Depot derivatives of the compounds are useful for providing long acting effects of the compounds. The compounds are also useful as analgesics by administering a pain-relieving effective amount of one of the compounds to a mammal.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: September 17, 1996
    Assignee: Hoechst-Roussel Pharmaceuticals, Inc.
    Inventors: Joseph T. Strupczewski, Grover C. Helsley, Edward J. Glamkowski, Yulin Chiang, Kenneth J. Bordeau, Peter A. Nemoto, John J. Tegeler
  • Patent number: 5521181
    Abstract: The present invention relates to a compound of the formula ##STR1## and the pharmaceutically acceptable salts thereof wherein W is a bicyclic heterocyclic ring system. The compounds are .alpha.-1 adrenergic antagonists and are useful in the treatment of BPH; also disclosed are .alpha.-1 antagonist compositions and a method for antagonizing .alpha.-1 receptors and treating BPH.
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: May 28, 1996
    Assignee: Abbott Laboratories
    Inventors: Michael D. Meyer, Robert J. Altenbach, William A. Carroll, Irene Drizin, Suzanne A. Lebold, Edmund L. Lee, Kevin B. Sippy, Karin R. Tietje, Diane M. Yamamoto, James F. Kerwin, Jr.
  • Patent number: 5521182
    Abstract: The cyclic amide derivative is defined by the formula (I) or a salt thereof:R.sup.1 --(CH.sub.2).sub.n --Zin whichR.sup.1 is a group derived from a cyclic amide compound, substituted or unsubstituted, n is zero or an integer of 1 to 10 and Z is ##STR1## R.sup.2 being an aryl, a substituted aryl, a cycloalkyl or a heterocyclic group, m being an integer of 1 to 6, R.sup.3 being hydrogen or a lower alkyl, R.sup.4 being an aryl or a substituted aryl, a cycloalkyl or a heterocyclic group, p being an integer of 1 to 6, provided that the cyclic amide compound is quinazoline-on or quinazoline-dion, R.sup.2 and R.sup.4 are neither aryl nor substituted aryl. The cyclic amide compound is pharmacologically effective to prevent and treat diseases due to insufficiency of the central choline functions.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: May 28, 1996
    Assignee: Eisai Co., Ltd.
    Inventors: Hachiro Sugimoto, Masahiro Yonaga, Norio Karibe, Youichi Iimura, Satoshi Nagato, Atsushi Sasaki, Yoshiharu Yamanishi, Hiroo Ogura, Takashi Kosasa, Kumi Uchikoshi, Kiyomi Yamatsu
  • Patent number: 5506243
    Abstract: Since sulfonamide derivatives of the present invention show strong inhibitory activity against cysteine protease such as calpain papain, cathepsin B, cathepsin H, cathepsin L, they can be used as remedies for muscular dystrophy, cataract, myocardial infarction, stroke, Alzheimer's disease, amyotrophia, osteoporosis, hypercalcemia or the like.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: April 9, 1996
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Toshiro Sakaki, Chizuko Takahashi, Yoshiyuki Fujimura
  • Patent number: 5504088
    Abstract: The cyclic amide derivative is defined by the formula (I) or a salt thereof:R.sup.1 --(CH.sub.2).sub.n --Zin which R.sup.1 is a group derived from a cyclic amide compound, substituted or unsubstituted, n is zero or an integer of 1 to 10 and Z is ##STR1## R.sup.2 being an aryl, a substituted aryl, a cycloalkyl or a heterocyclic group, m being an integer of 1 to 6, R.sup.3 being hydrogen or a lower alkyl, R.sup.4 being an aryl or a substituted aryl, a cycloalkyl or a heterocyclic group, p being an integer of 1 to 6, provided that the cyclic amide compound is quinazoline-on or quinazoline-dion, R.sup.2 and R.sup.4 are neither aryl nor substituted aryl. The cyclic amide compound is pharmacologically effective to prevent and treat diseases due to insufficiency of the central choline functions.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: April 2, 1996
    Assignee: Eisai Co., Ltd.
    Inventors: Hachiro Sugimoto, Masahiro Yonaga, Norio Karibe, Youichi Iimura, Satoshi Nagato, Atsushi Sasaki, Yoshiharu Yamanishi, Hiroo Ogura, Takashi Kosasa, Kumi Uchikoshi, Kiyomi Yamatsu
  • Patent number: 5489603
    Abstract: An insecticidal composition containing a guanidine derivative of the formula: ##STR1## wherein R.sup.1 is an optionally substituted homocyclic or heterocyclic group, n is 0 or 1, R.sup.2 is a hydrogen atom or an optionally substituted hydrocarbon group, R.sup.3 is a primary, secondary or tertiary amino group, X is an electron attractive group such as nitro or trifluoroacetyl group, provided that when n is 0, R.sup.1 is an optionally substituted heterocyclic group or a salt thereof.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: February 6, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideki Uneme, Koichi Iwanaga, Noriko Higuchi, Isao Minamida, Tetsuo Okauchi
  • Patent number: 5459264
    Abstract: A method for reducing an .alpha.,.beta.-unsaturated ketone of the present invention includes the step of treating the .alpha.,.beta.-unsaturated ketone with a silyl compound in the presence of a Lewis acid and alcohol to selectively reduce the carbonyl group of the .alpha.,.beta.-unsaturated ketone. According to this method, a deoxy-compound can be obtained from the .alpha.,.beta.-unsaturated ketone by selectively reducing the carbonyl group without reducing an .alpha.,.beta.-unsaturated bond.
    Type: Grant
    Filed: December 17, 1993
    Date of Patent: October 17, 1995
    Assignee: Shionogi Seiyaku Kabushiki Kaisha
    Inventors: Mitsuru Imuta, Makoto Kobayashi, Teruo Iizuka
  • Patent number: 5364866
    Abstract: Heteroarylpiperidines, pyrrolidines, and piperazines are useful as antipsychotic and analgesic agents. The compounds are especially useful for treating psychoses by administering to a mammal a psychoses-treating effective amount of one of the compounds. The compounds are also useful as analgesics by administering a pain-relieving effective amount of one of the compounds to a mammal.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: November 15, 1994
    Assignee: Hoechst-Roussel Pharmaceuticals, Inc.
    Inventors: Joseph T. Strupczewski, Grover C. Helsley, Yulin Chiang, Kenneth J. Bordeau, Edward J. Glamkowski
  • Patent number: 5350749
    Abstract: 4-substituted-pyrido[3,2-d]pyridmidine, -pyrido[4,3-d]pyrimidine, -pyrido[3,4-d]pyrimidine, pyrido[2,3-d]pyrimidine, -pteridine, -pyrimido[4,5-d]pyrimidine, -pyrimido[4,5-c]pyridazine, -pyrimido[5,4-d]pyrimidine, -pyrimido[5,4-c]pyridazine, pyrimido[4,5-d]pyridazine, and pyrimido[5,4-e]-1,2,4-triazine derivatives, for example 4-[2-(4-chlorophenyl)ethoxy]pyrido[2,3-d]pyrimidine, are useful as fungicides, inseciticides and miticides.
    Type: Grant
    Filed: April 22, 1991
    Date of Patent: September 27, 1994
    Assignee: DowElanco
    Inventors: Ronald E. Hackler, Glen P. Jourdan
  • Patent number: 5340832
    Abstract: A novel prolinal derivative of the general formula: ##STR1## [wherein A represents alkylene or alkenylene group of from 1 to 8 carbon atom(s) or a saturated hydrocarbon ring of from 3 to 7 carbon atoms, R represents hydrogen atom, phenyl group, benzyl group, alkyl group of from 1 to 8 carbon atom(s) or cycloalkyl group of from 3 to 7 carbon atoms,B represents alkylene group of from 1 to 8 atom(s) unsubstituted or substituted by phenyl group or benzyl group, or a single bond,D represents carbocyclic or heterocyclic ring unsubstituted or substituted by from one to three of halogen atom, alkyl or alkoxy group of from 1 to 4 carbon atom(s), nitro group or trifluoromethyl group.]possess inhibitory activity on prolyl endopeptidase, and therefore are useful for treating and/or preventing agent as a amnesia.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: August 23, 1994
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
  • Patent number: 5326766
    Abstract: Compounds of the formula (I): ##STR1## wherein: Het is pyridyl, pyrazinyl, pyrimidinyl, or pyridizinyl, optionally substituted with one or more groups selected from halo, lower alkyl, lower alkoxy, haloalkyl, haloalkoxy, NO.sub.2, CN, and lower alkoxy-carbonyl;Z is a C--C single bond, CH.sub.2, NH, O, S, --CH.sub.2 O--, or --OCH.sub.2 --; andthe remaining groups are as defined in the specification are useful as pesticides.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: July 5, 1994
    Inventors: Barry A. Dreikorn, Sylvester V. Kaster, Neil V. Kirby, Robert G. Suhr, Brian R. Thoreen
  • Patent number: 5270465
    Abstract: The present invention relates to 4(3H)-pteridinones represented by the formula: ##STR1## in which X is an oxygen atom or a sulphur atom, Y is a hydrogen atom, a lower alkyl radical, especially a methyl radical, at the 6-position or a hydroxyl group at the 7-position, R.sub.1 is a hydrogen atom, a lower alkyl radical, a substituted or unsubstituted phenyl radical, a benzyl radical, a methoxymethyl group, an acetyl group, a 2-acetoxyethyl group or a 2,2,2-trifluoroethyl group and R.sub.2 is a hydrogen atom or a lower alkyl radical, especially a methyl radical.Application of these compounds as anti-allergic drugs.
    Type: Grant
    Filed: November 3, 1992
    Date of Patent: December 14, 1993
    Assignee: Lipha, Lyonnaise Industrille Pharmaceutique
    Inventors: Gerard Ferrand, Herve Dumas, Jean-Claude Depin, Yvette Quentin
  • Patent number: 5239074
    Abstract: The present invention relates to a novel method of preparing diastereoisomers derived from tetrahydrofolic acid. By reacting (i) (6RS)-folinic acid or one of its salts, or (ii) 5,10-methenyl-5,6,7,8-tetrahydrofolic acid, with HCOOH at pH 2.0-2.6, a precipitate is obtained which consists of a mixture of two diastereoisomers of orthoamide structure and of the formulae ##STR1## in which R is the p-benzoyl-(L)-glutamic acid residue, in a molar ratio IV/III of about 7/3, compound III being of so-called natural configuration and compound IV being of so-called unnatural configuration. The pure compound IV is isolated from said precipitate and the pure compound III is isolated from the corresponding filtrate. The diastereoisomers of the reduced folates and their salts of natural and unnatural configuration are prepared from compounds III and respectively IV.
    Type: Grant
    Filed: November 6, 1991
    Date of Patent: August 24, 1993
    Assignee: Sapec S.A.
    Inventors: Fabrizio Marazza, Attilio Melera, Rene Viterbo
  • Patent number: 5198547
    Abstract: Intermediates and a process for the synthesis of 6-monosubstituted tetrahydropteridine C6-stereoisomers, including (6S)-tetrahydrofolic acid. The intermediates are shown in their two enantiomeric forms as follows: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and represent hydrogen, methyl, hydroxy, amino, alkyl or dialkylamino, alkoxy, benzyloxy, or benzylthio; R.sub.3 represents an alkene, alkyne, cycloalkyl, benzyl, alkyl (substituted with hydroxy, acetoxy, benzyloxy, alkoxy, alkylthio, amino, carboxy, oxo, or phosphate), a protected aldehyde, or ##STR2## wherein n=1 or 2, R.sub.4 is hydrogen, formyl, methyl, or propargyl, and ZZ represents an amino acid or amino acid polymer. Also, a process for tetrahydropteridine N5-formylation for the preparation of, for example, N5-formyl-(6S)-tetrahydrofolic acid.
    Type: Grant
    Filed: March 16, 1992
    Date of Patent: March 30, 1993
    Assignee: South Alabama Medical Science Foundation, USA
    Inventors: Steven W. Bailey, June E. Ayling
  • Patent number: 5196533
    Abstract: 6,6-Disubstituted pteridines which are useful for the regulation of enzymes are disclosed, along with a general method of synthesizing these compounds.
    Type: Grant
    Filed: March 14, 1991
    Date of Patent: March 23, 1993
    Assignee: South Alabama Medical Science Foundation, USA
    Inventors: June E. Ayling, Steven W. Bailey
  • Patent number: 5176716
    Abstract: Hair dye composition for oxidative dyeing of human or animal hair containing as developing substances alone or in admixture with other developing substances, a hydroxytriaminopyrimidine, preferably 6-OH-2,4,5-triaminopyrimidine (4-OH-2,5,6-triaminopyrimidine) or 2-OH-4,5,6-triaminopyrimidine and/or a dihydroxydiaminopyrimidine, preferably 2,6-dihydroxy-4,5-diamino-pyrimidine or 4,6-dihydroxy-2,5-diaminopyrimidine.
    Type: Grant
    Filed: May 21, 1991
    Date of Patent: January 5, 1993
    Assignee: Goldwell AG
    Inventors: Heribert Lorenz, Frank Kufner, Jurgen Tennigkeit
  • Patent number: 5104876
    Abstract: Novel benzopyrido piperidiene, piperidylidene and piperazine compounds of the generalized formula ##STR1## are disclosed as useful for the treatment of asthma, allergy and inflammation. Novel pharmaceutical compositions containing such compounds and processes for producing the compounds are also disclosed.
    Type: Grant
    Filed: October 26, 1990
    Date of Patent: April 14, 1992
    Assignee: Schering Corporation
    Inventors: John J. Piwinski, Jesse K. Wong, Michael J. Green, Ashit K. Ganguly, Frank J. Villani
  • Patent number: 5084459
    Abstract: There is provided a pest control composition containing a compound represented by the formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and independently mean a hydrogen atom, a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted and X means an electron attracting group or a salt thereof.The compounds are of minimal toxicity to man, domestic animals and fish and selectively display remarkable control effect on pests.
    Type: Grant
    Filed: October 25, 1989
    Date of Patent: January 28, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideki Uneme, Isao Minamida, Tetsuo Okauchi, Noriko Higuchi
  • Patent number: 5047404
    Abstract: This invention relates to fused pyrimidine derivatives which have bronchodilator and anti-allergic activities. A compound of the invention is 2-(2-propoxyphenyl)pyrido[2,3-d]pyrimid-4(3H)-one.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: September 10, 1991
    Assignee: Smith Kline & French Laboratories, Ltd.
    Inventors: William J. Coates, Sean T. Flynn, Derek A. Rawlings
  • Patent number: 5047405
    Abstract: Pteridines of general formula (I): ##STR1## in which Y and Z, which can be identical or different, are hydrogen, OH or NH.sub.2, and X.sub.1 and X.sub.2, which can be identical or different, are hydrogen, OH, C.sub.1 -C.sub.4 alkyl, phenyl, hydroxymethyl or carboxyl, for the preparation of pharmaceutical compositions for treating cognitive pathologies characterized by memory and vigilance disturbances, such as senile dementia of Alzheimer type, multiinfarctual dementia, metabolic encephalopathies, Korsakoff's syndrome, and the consequences of the abuse of certain therapies such as anxiolytic and neuroleptic.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: September 10, 1991
    Assignee: Bioresearch S.p.A.
    Inventor: Federico Gennari
  • Patent number: 5034393
    Abstract: Fungicidal compositions contain as active ingredient a 4-substituted-pyrido[3,2-d]pyrimidine, -pyrido[4,3-d]pyrimidine, -pyrido[3,4-d]pyrimidine, pyrido[2,3-d]pyrimidine, -pteridine, -pyrimido[4,5-d]pyrimidine, -pyrimido[4,5-c]pyridazine, -pyrimido[5,4-d]pyrimidine, -pyrimido[5,4-c]pyridazine, pyrimido[4,5-d]pyridazine, or -pyrimido[5,4-e]-1,2,4-triazine, for example 4-[2-(4-chlorophenyl)ethoxy]pyrido[2,3-d]pyrimidine.
    Type: Grant
    Filed: July 27, 1989
    Date of Patent: July 23, 1991
    Assignee: DowElanco
    Inventors: Ronald E. Hackler, Glen P. Jourdan
  • Patent number: 5026418
    Abstract: Pyrimidine compounds useful as plant growth regulators have the formula (I): ##STR1## wherein Y is an optionally substituted secondary or tertiary alkyl group containing from 3 to 7 carbon atoms or an optionally substituted cycloalkyl or alkylcycloalkyl group containing from 3 to 7 carbon atoms; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen or a lower alkyl group; A is an optionally substituted heterocyclic group, for example thienyl or pyridyl; n is an integer which may be from 0 to 2 and is preferably 0; and R.sup.3 is hydrogen, an alkyl group containing from 1 to 4 carbon atoms, or an alkenyl or alkynyl group containing from 2 to 4 carbon atoms.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: June 25, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventor: Kevin R. Lawson
  • Patent number: 5002944
    Abstract: Compounds useful for increasing cardiotonic contractility in humans or other animals and pharmaceutical compositions including these compounds are disclosed. The compounds have the general structure: ##STR1## where A is ##STR2## R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.9, and R.sub.10 are H, lower alkyl of 1-4 carbon atoms, phenyl, substituted phenyl, phenyl lower alkyl of 1-4 carbon atoms or substituted phenyl lower alkyl of 1-4 carbon atoms; and n is 0 or 1.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: March 26, 1991
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Alfred P. Spada, Henry F. Campbell, Donald E. Kuhla, William L. Studt, William C. Faith, Bruce F. Molino
  • Patent number: 4988813
    Abstract: 2-Amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-en-1-yl]pyrido[2,3,-d]pyrimid ines and 2-amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-yn-1-yl]pyrido[2,3-d]pyrimid ines are prepared through through the reaction of a haloaromatic compound and an unsaturated compound in the presence of a palladium catalyst. The products are chemical intermediates for the preparation of antineoplastic agents.A typical embodiment is the reaction of a protected 2-amino-4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine and an ester of 4-iodobenzoic acid.
    Type: Grant
    Filed: August 8, 1988
    Date of Patent: January 29, 1991
    Assignee: The Trustees of Princeton University
    Inventors: Edward C. Taylor, George S. K. Wong
  • Patent number: 4831137
    Abstract: Thermosettable prepolymers or resins are prepared by reacting (1) a pyrazine compound containing at least two substituent groups which have a hydrogen atom attached to a carbon atom which is attached to the ring such as tetramethylpyrazine, (2) a material containing at least two aromatic aldehyde groups, and (3) at least one of (a) a nitrogen containing aromatic heterocyclic compound containing at least one hydrogen atom attached to a carbon atom attached to the ring and a polymerizable unsaturated group such as 2-methyl-5-vinylpyridine or (b) an aldehyde containing at least one polymerizable unsaturated group such as 4-isopropenyl-1-cyclohexane-1-carboxaldehyde. These prepolymers or resins are curable to thermoset products having good mechanical and thermal properties by heat and pressure or by homopolymerization or copolymerization with N,N'-bis-imides such as 1,1'-(methylenedi-4,1-phenylene)bismaleimide. The prepolymers are suitable for preparing composites.
    Type: Grant
    Filed: March 15, 1988
    Date of Patent: May 16, 1989
    Assignee: The Dow Chemical Company
    Inventor: Duane S. Treybig
  • Patent number: 4797488
    Abstract: Substituted imides of the following formula are antipsychotic, anxiolytic agents with very little extrapyramidal side effects: ##STR1## in which X is --O--, --S--, --SO--, --SO.sub.2 --, --CR.sub.3 R.sub.4 -- where R.sub.3 and R.sub.4, independently, are hydrogen, alkyl of 1 to 4 carbon atoms or, taken together with the carbon atom to which they are attached, R.sub.3 and R.sub.4 form a cycloalkyl group of of 3 to 5 carbon atoms; n is one of the integers 2, 3, 4 or 5; R is phenyl, halophenyl, trifluoromethylphenyl, alkoxyphenyl in which the alkoxy substituent contains 1 to 3 carbon atoms, 2-pyrimidinyl, halopyrimidin-2-yl, 2-pyrazinyl, halopyrazin-2-yl, 2-pyridinyl, cyanopyridin-2-yl, halopyridin-2-yl, quinolyl, or haloquinolyl; R.sub.1 and R.sub.2, taken together, are alkylene of 3 to 5 carbon atoms or alkenylene of 3 to 5 carbon atoms, or taken with the carbon atoms to which they are attached, R.sub.1 and R.sub.2 complete a benzene ring, or a group of the formula: ##STR2## where Y is --CH.sub.2 --, --CH.sub.
    Type: Grant
    Filed: April 3, 1987
    Date of Patent: January 10, 1989
    Assignee: American Home Products Corporation
    Inventors: Gary P. Stack, Thomas D. Golobish, Magid A. Abou-Gharbia
  • Patent number: 4755600
    Abstract: Thermosettable prepolymers or resins are prepared by reacting (1) a pyrazine compound containing at least two substituent groups which have a hydrogen atom attached to a carbon atom which is attached to the ring such as tetramethylpyrazine, (2) a material containing at least two aromatic aldehyde groups, and (3) at least one of (a) a nitrogen containing aromatic heterocyclic compound containing at least one hydrogen atom attached to a carbon atom attached to the ring and a polymerizable unsaturated group such as 2-methyl-5-vinylpyridine or (b) an aldehyde containing at least one polymerizable unsaturated group such as 4-isopropenyl-1-cyclohexene-1-carboxaldehyde. These prepolymers or resins are curable to thermoset products having good mechanical and thermal properties by heat and pressure or by homopolymerization or copolymerization with N,N'-bis-imides such as 1,1'-(methylenedi-4,1-phenylene)bismaleimide. The prepolymers are suitable for preparing composites.
    Type: Grant
    Filed: March 17, 1986
    Date of Patent: July 5, 1988
    Assignee: The Dow Chemical Company
    Inventor: Duane S. Treybig
  • Patent number: 4752573
    Abstract: The use of pterins to increase the activity of lymphokines and other cell growth factors, and a diagnostic or theraupeutic preparation that contains pterins combined with lymphokines. Adding pterins to lymphokines can increase the activity of the lymphokines by 3 to 5 times.
    Type: Grant
    Filed: April 8, 1986
    Date of Patent: June 21, 1988
    Assignees: Biotest-Serum-Institut GmbH, Gesellschaft fur Strahlen-und Umweltforschung mbH
    Inventors: Irmgard Ziegler, Udo Schwulera, Hans Sonneborn
  • Patent number: 4698352
    Abstract: This invention relates to a novel 4-oxo-1,4-dihydronicotinic acid derivative ##STR1## or a salt thereof, wherein R.sup.1 is hydrogen or carboxyl-protecting group;R.sup.2 is substituted phenyl and naphthyl, or a substituted or unsubstituted heterocyclic group; andR.sup.3 is haloalkyl, aminoalkyl, or substituted or unsubstituted alkenyl, phenylalkenyl, naphthylalkenyl, phenylalkyl, naphthylalkyl, phenylalkynyl, naphthylalkynyl, heterocyclic alkyl, heterocyclic alkenyl, phenyl, naphthyl, cycloalkyl, cycloalkenyl, carboxylic acyl, iminoalkyl, heterocyclic or bridged hydrocarbon, which has a broad antibacterial spectrum and a low toxicity, and are useful for treatment of diseases of human beings and animals, to a process for producing the same and to an antibacterial agent containing the same.
    Type: Grant
    Filed: October 27, 1983
    Date of Patent: October 6, 1987
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Hirokazu Narita, Yoshinori Konishi, Jun Nitta, Shunjiro Misumi, Hideyoshi Nagaki, Isao Kitayama, Yoriko Nagai, Yasuo Watanabe, Nobuyuki Matsubara, Shinzaburo Minami, Isamu Saikawa
  • Patent number: 4465681
    Abstract: Pyridine derivatives of the formula: ##STR1## or pharmaceutically acceptable acid addition salts thereof, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and each represents hydrogen atom or lower alkyl group, or R.sup.1 and R.sup.2, or R.sup.3 and R.sup.4 together with the adjacent nitrogen atom form a heterocycle, A.sup.1 and A.sup.2 are the same or different and each represents alkylene or hydroxy-substituted alkylene group, Y.sup.1 and Y.sup.2 are the same or different and each represents oxygen or sulfur atom, and Z represents ##STR2## These compounds show pharmacological activities such as potentiating activity for leukocyte phagocytosis, potentiating activity for macrophage phagocytosis, potentiating activity for the production of rosette forming cells in the spleen and anti-adjuvant arthritis activity, and are useful as medicines.
    Type: Grant
    Filed: July 28, 1982
    Date of Patent: August 14, 1984
    Assignee: Yoshitomi Pharmaceutical Industries Ltd.
    Inventors: Takanori Oe, Mineo Tsuruda, Kazuhiro Goto, Masao Hisadome
  • Patent number: 4463006
    Abstract: Diglycidyl-substituted pteridine compounds of the general formula: ##STR1## wherein n is the whole number 1 or 2, R.sub.2 and R.sub.2 are the same or different, and are either hydrogen, a hydrocarbon radical, or together form a 5- or 6-membered carbocyclic or heterocyclic ring; processes for their preparation; and compositions and methods for their use as cytostatic agents.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: July 31, 1984
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hinrich Moller, Brigitte Hase, Gunther Konrad, Hans-Christoph Wilk, Ulrich Zeidler
  • Patent number: 4361700
    Abstract: Derivatives of pyridopyrimidinone of the following formulae: ##STR1## wherein Y is C.dbd.S, C.dbd.O, SO.sub.2, or CH.sub.2 ;Z is C--H, N, S or O;R.sub.1 is hydrogen, hydroxyl, halogen, lower alkyl or R.sub.3 ;R.sub.2 is hydrogen, aliphatic hydrocarbon, substituted aliphatic hydrocarbon or carbocyclic aryl-aliphatic hydrocarbon, wherein the substituent of the aliphatic hydrocarbon may be hydroxyl, halogen, alkoxy, carboxylic acid ester, or lower alkyl amine;R.sub.3 is ##STR2## wherein A is carbon, nitrogen, oxygen, or sulfur; R.sub.
    Type: Grant
    Filed: May 20, 1980
    Date of Patent: November 30, 1982
    Assignee: James S. Waldron
    Inventors: William P. Purcell, Richard D. Gilliom, Harlie A. Parish, Jr.
  • Patent number: 4337339
    Abstract: Folic acid derivatives, such as radiolabeled pteroyltyrosine, are conveniently synthesized from either pteroic acid or by the direct condensation of 6-formylpterin with p-aminobenzoyltyrosine methyl ester. The radioiodinated derivatives are particularly useful in competitive protein binding and radioimmuno-assays of folate compounds.
    Type: Grant
    Filed: October 31, 1979
    Date of Patent: June 29, 1982
    Assignee: Baker Instruments Corp.
    Inventors: Peter R. Farina, James A. Grattan
  • Patent number: 4314988
    Abstract: Folic acid derivatives, such as radiolabeled pteroyltyrosine, are conveniently synthesized from either pteroic acid or by the direct condensation of 6-formylpterin with p-aminobenzoyltyrosine methyl ester. The radioiodinated derivatives are particularly useful in competitive protein binding and radioimmuno-assays of folate compounds.
    Type: Grant
    Filed: October 31, 1979
    Date of Patent: February 9, 1982
    Assignee: Baker Instruments Corp.
    Inventors: Peter R. Farina, James A. Grattan
  • Patent number: 4298735
    Abstract: Folic acid derivatives, such as radiolabeled pteroyltyrosine, are conveniently synthesized from either pteroic acid or by the direct condensation of 6-formylpterin with p-aminobenzoyltyrosine methyl ester. The radioiodinated derivatives are particularly useful in competitive protein binding and radioimmuno-assays of folate compounds.
    Type: Grant
    Filed: April 30, 1979
    Date of Patent: November 3, 1981
    Assignee: Union Carbide Corporation
    Inventors: Peter R. Farina, James A. Grattan
  • Patent number: 4224446
    Abstract: Process for the production of methotrexate, which is N[p-([(2,4-diamino-6-pteridyl)-methyl]-N.sup.10 -methylamino)-benzoyl]-L-glutamic acid. The process includes converting 1,1-dichloroacetone with 2,4,5,6-tetraaminopyrimidine in the presence of sodium bisulfite at a constant pH between 3.5 and 5 and at a temperature between 10.degree. and 100.degree. C. The resultant 2,4-diamino-6-methylpteridine is converted in a reaction medium with bromide. 0.3 to 1.0 ml of bromine is used per 1.0 g of the 2,4-diamino-6-methylpteridine. The 2,4-diamino-6-bromo methyl pteridine is converted with p-(N-methyl)-aminobenzoyl-L-glutamic acid or a salt thereof in a polar reaction medium into methoxtrexate.
    Type: Grant
    Filed: July 19, 1978
    Date of Patent: September 23, 1980
    Assignee: Lonza Ltd.
    Inventor: Enrico Catalucci
  • Patent number: 4183934
    Abstract: Specific 4-hydroxy-pteridines carrying particular phenyl substituents in the 7-position and no substituents in the 2-position have been found to be excellent nonkaliuretic diuretics at doses of 30 to 500 mg/kg in warm-blooded animals.
    Type: Grant
    Filed: October 16, 1978
    Date of Patent: January 15, 1980
    Assignee: Abbott Laboratories
    Inventors: Gerard Y. Paris, Denis G. Cimon, Dilbagh S. Bariana, Anthony Fung