Chalcogen Bonded Directly To The Oxazine Ring Patents (Class 544/92)
  • Patent number: 6331627
    Abstract: The present invention relates to novel antiobesity and hypocholesterolemic compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. More particularly, the present invention relates to novel &bgr;-aryl-&agr;-oxysubstituted alkylcarboxylic acids of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereo-somers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them.
    Type: Grant
    Filed: July 5, 2000
    Date of Patent: December 18, 2001
    Assignee: Reddy's Laboratories Ltd.
    Inventors: Vidya Bhushan Lohray, Braj Bhushan Lohray, Rao Bheema Paraselli, Rajagopalan Ramanujam, Ranjan Chakrabarti
  • Patent number: 6313113
    Abstract: The present invention relates to novel antidiabetic compounds, their tautomeric forms, their derivatives, their analogues, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them.
    Type: Grant
    Filed: December 2, 1997
    Date of Patent: November 6, 2001
    Assignees: Reddy-Cheminor, Inc., Dr. Reddy's research foundation
    Inventors: Vidya Bhushan Lohray, Braj Bhushan Lohray, Rao Bheema Paraselli, Rajagopalan Ramanujam, Ranjan Chakrabarti
  • Patent number: 6303780
    Abstract: The present invention relates to benzoxazinones of formula I: or stereoisomeric forms or mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HIV reverse transcriptase, and to pharmaceutical compositions and diagnostic kits comprising the same, methods of using the same for treating viral infection or as an assay standard or reagent, and intermediates and processes for making the same.
    Type: Grant
    Filed: July 27, 2000
    Date of Patent: October 16, 2001
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Joseph Marian Fortunak, Rodney Lawrence Parsons, Jr., Mona Patel
  • Patent number: 6303542
    Abstract: This invention relates to 3-substituted-phenyl-1,2,3-benzotriazin-4-ones which have activity as herbicides, to compositions which contain these compounds and to methods of use of these compounds.
    Type: Grant
    Filed: August 18, 2000
    Date of Patent: October 16, 2001
    Assignee: Rohm and Haas Company
    Inventors: Bin Li, Adam Chi-Tung Hsu
  • Publication number: 20010016653
    Abstract: The instant invention describes a method for crystallizing (−)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one from a solvent and anti-solvent solvent system and producing the crystalline product. The desired final crystal form, Form I, can be produced when using methanol or ethanol. Form II is isolated from 2-propanol and can be converted to the desired crystal form at low drying temperatures, such as between about a temperature of 40° C. and 50° C.
    Type: Application
    Filed: March 31, 1999
    Publication date: August 23, 2001
    Inventors: LOUIS S. CROCKER, JOSEPH L. KUKURA
  • Patent number: 6235733
    Abstract: A palatable oral liquid pharmaceutical composition of benzoxazinone compounds useful as HIV reverse transcriptase inhibitors comprising the benzoxazinone active ingredient in a liquid vehicle comprising medium chain fatty acid triglycerides. Other formulating agents such as sweetening agents, lecithin suspending agents, etc. may be optionally added.
    Type: Grant
    Filed: February 16, 1999
    Date of Patent: May 22, 2001
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Surendra M. Bahal, Michael B. Maurin
  • Patent number: 6180625
    Abstract: Compounds of formula (I) as factor VII-tissue factor inhibitors as well as novel benzoxazin derivatives are disclosed, wherein R1, R2, R3, X and Y are as defined in the specification. These compounds, and pharmaceutically acceptable salts thereof, have been shown to be inhibitors of factor VIIa-tissue factor activity and have anticoagulant properties. These compounds are useful for treating deficiencies of blood clotting factors or the effects of inhibitors to blood clotting factors. Methods for inhibiting clotting activity are also disclosed.
    Type: Grant
    Filed: March 22, 1999
    Date of Patent: January 30, 2001
    Assignee: Novo Nordisk A/S
    Inventors: Egon Persson, Palle Jakobsen, Helle Worsaae
  • Patent number: 6147210
    Abstract: The present invention describes novel methods for the synthesis of benzoxazinone compounds which are useful as human immunodeficiency virus (HIV) reverse transcriptase inhibitors. The benzoxazinone of the formula: is particularly effective in the treatment of HIV.
    Type: Grant
    Filed: June 25, 1999
    Date of Patent: November 14, 2000
    Assignee: Dupont Pharmaceuticals Company
    Inventors: Michael Ernest Pierce, Lilian Alicia Radesca
  • Patent number: 6140499
    Abstract: The present invention relates to benzoxazinones of formula I: ##STR1## or stereoisomeric forms or mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HIV reverse transcriptase, and to pharmaceutical compositions and diagnostic kits comprising the same, methods of using the same for treating viral infection or as an assay standard or reagent, and intermediates and processes for making the same.
    Type: Grant
    Filed: October 21, 1998
    Date of Patent: October 31, 2000
    Assignee: DuPont Pharmaceutical Company
    Inventors: Joseph Marian Fortunak, Rodney Lawrence Parsons, Jr.
  • Patent number: 6130214
    Abstract: The present invention relates to novel antiobesity and hypocholesterolemic compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. More particularly, the present invention relates to novel .beta.-aryl-.alpha.-oxysubstituted alkylcarboxylic acids of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them.
    Type: Grant
    Filed: October 26, 1998
    Date of Patent: October 10, 2000
    Assignees: Dr. Reddy's Research Foundation, Reddy-Cheminor, Inc.
    Inventors: Vidya Bhushan Lohray, Braj Bhushan Lohray, Rao Bheema Paraselli, Rajagopalan Ramanujam, Ranjan Chakrabarti
  • Patent number: 6107293
    Abstract: Compounds of formula (I) wherein X is --CH.sub.2 --, --CO-- or direct linkage, Y is --O--, --S-- or --NH--, R.sub.1 is phenyl, R.sub.2 .dbd.H or phenyl and R.sub.3 is H or --CH.sup.3 -- and their pharmaceutically acceptable salts have tachykinin antagonist activity and are useful as pharmaceuticals e.g. for the treatment of pain and migraine.
    Type: Grant
    Filed: July 14, 1999
    Date of Patent: August 22, 2000
    Assignee: Novaris AG
    Inventors: Christopher Simon John Walpole, Mahavir Prashad, Denis Har
  • Patent number: 6090805
    Abstract: This invention relates to certain novel benzoxazinone compounds and derivatives thereof, their synthesis, and their use as oxytocin receptor antagonists. One application of these compounds is in the treatment of preterm labor in mammals, especially humans. The ability of the compounds to relax uterine contractions in mammals also makes them useful for treating dysmenorrhea and stopping labor prior to cesarean delivery.
    Type: Grant
    Filed: June 10, 1998
    Date of Patent: July 18, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Peter D. Williams, Michelle A. Sparks, Ian Bell, Debra S. Perlow, Kenneth Stauffer, Roger M. Freidinger
  • Patent number: 6069114
    Abstract: Compounds of the formula (I) and their salts ##STR1## in which R.sup.1 to R.sup.6, Y.sup.1, to Y.sup.2, Y.sup.3, m and n are as defined in claim 1 are suitable as herbicides and plant growth regulators. They can be prepared analogously to known processes using intermediates of the formula (V) (cf. claim 6).
    Type: Grant
    Filed: February 25, 1997
    Date of Patent: May 30, 2000
    Assignee: Hoechst Schering AgrEvo GmbH
    Inventors: Klaus Lorenz, Klemens Minn, Lothar Willms, Klaus Bauer, Hermann Bieringer, Christopher Rosinger
  • Patent number: 6046211
    Abstract: The current invention discloses useful pharmaceutical compositions containing amidino derivative useful as nitric oxide synthase inhibitors.
    Type: Grant
    Filed: May 6, 1998
    Date of Patent: April 4, 2000
    Assignee: G.D. Searle & Co.
    Inventors: Donald W. Hansen, Jr., Mark G. Currie, E. Ann Hallinan, Kam F. Fok, Timothy J. Hagen, Arija A. Bergmanis, Steven W. Kramer, Len F. Lee, Suzanne Metz, William M. Moore, Karen B. Peterson, Barnett S. Pitzele, Dale P. Spangler, R. Keith Webber, Mihaly V. Toth, Mahima Trivedi, Foe S. Tjoeng
  • Patent number: 6040443
    Abstract: There is described a process for the production of a 1,3-benzoxazin-4-one having the formula: ##STR1## in which R.sub.1 and R.sub.2, independently, are hydrogen, cyano, halogen, nitro, C.sub.1 -C.sub.20 alkyl, O--C.sub.1 -C.sub.20 alkyl, phenyl, NH--CO--C.sub.1 -C.sub.20 alkyl, N(R.sub.3).sub.2, SO.sub.2 N(R.sub.3).sub.2, COOR.sub.3 or CON(R.sub.3).sub.2 in which R.sub.3 is hydrogen, cyano, halogen, nitro, C.sub.1 -C.sub.20 alkyl, O--C.sub.1 -C.sub.20 alkyl, phenyl or NH--CO--C.sub.1 -C.sub.20 alkyl, comprising reacting, at elevated temperature, 1 molar equivalent of an o-hydroxybenzamide of formula: ##STR2## in which R.sub.1 has its previous significance, with 2 to 6 molar equivalents of a benzoyl chloride of formula: ##STR3## in which R.sub.2 has its previous significance. The 1,3-benzoxazin-4-ones having the formula (1) so obtained are important intermediates for the production of triazine compounds having excellent absorption spectrum characteristics and good resistance to exposure to UV light.
    Type: Grant
    Filed: July 20, 1998
    Date of Patent: March 21, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Georges Metzger, Dieter Reinehr, Serge Hauger
  • Patent number: 6030973
    Abstract: The present invention relates to novel antidiabetic compounds, their tautomeric forms, their derivatives, their analogues, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. This invention particularly relates to novel azolidinediones of the general formula (I), their analogues, their derivatives, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, pharmaceutically acceptable solvates and pharmaceutical compositions containing them.
    Type: Grant
    Filed: August 17, 1998
    Date of Patent: February 29, 2000
    Assignees: Dr. Reddy's Research Foundation, Reddy-Cheminor, Inc.
    Inventors: Vidya Bhushan Lohray, Braj Bhushan Lohray, Rao Bheema Paraselli, Rajagopalan Ramanujam, Ranjan Chakrabarti
  • Patent number: 6015926
    Abstract: An efficient method for the preparation of key intermediate, in the synthesis of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one, a reverse transcriptase inhibitor is achieved using a chiral addition reaction to the 4-chloro-2-trifluoromethylketoaniline with an organozinc complex to give the desired alcohol. This instant method has broad applicability in the chiral addition to any prochiral ketone.
    Type: Grant
    Filed: May 11, 1998
    Date of Patent: January 18, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Cheng Yi Chen, Lushi Tan, Richard D. Tillyer
  • Patent number: 6011150
    Abstract: There is disclosed an azetidinone compound of the formula [I]: ##STR1## wherein Ring B is a benzene ring which may have substituent(s), R.sup.1 is a hydroxy-substituted lower alkyl group which may have substituent(s), X is oxygen atom and the like, Y is oxygen atom and the like, and Z is a methylene group which may have substituent(s), which is useful as a synthetic intermediate of the 1.beta.-methylcarbapenem-type antibacterial agent.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: January 4, 2000
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Tameo Iwasaki, Kazuhiko Kondo
  • Patent number: 5985872
    Abstract: A class of compounds for the treatment of viral infections. Compounds of particular interest are defined by Formula II ##STR1## wherein R.sup.28 is selected from (a) amino substituted with one or two radicals selected from alkyl, aralkyl, heterocycoalkyl, heterocyclo, and aryl, and (b) amino acid residues and derivatives thereof; wherein R.sup.29 is selected from hydrido, alkyl, halo, ##STR2## wherein R.sup.30 is selected from alkyl, alkoxy, alkylamino, carboxyalkyl, alkoxyalkyl, alkylaminoalkyl, cycloalkyl, heterocyclo, heterocycloalkyl, heterocycloalkoxy, alkylaminoalkoxy, alkylaminoalkylamino, heterocycloalkylamino, and N-aralkylamino; wherein R.sup.31 is alkyl; wherein R.sup.32 is alkyl and aryl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: November 16, 1999
    Assignee: G.D. Searle & Co.
    Inventors: Norman Anthony Abood, Daniel L. Flynn, Daniel P. Becker, Brian M. Bax, Hui Li, Roger A. Nosal, Lori A Schretzman, Clara I Villamil
  • Patent number: 5981436
    Abstract: The invention relates to new substituted diazacyclohexanedi(thi)ones of the general formula (I) ##STR1## in which Q.sup.1, Q.sup.2, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 have the meanings given in the description,a process for their preparation, new intermediate products and their use as herbicides.
    Type: Grant
    Filed: April 29, 1998
    Date of Patent: November 9, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Mark-Wilhelm Drewes, Roland Andree, Otto Schallner, Hans-Joachim Santel, Markus Dollinger
  • Patent number: 5965729
    Abstract: The instant invention describes a method for crystallizing (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one from a solvent and anti-solvent solvent system and producing the crystalline product. The desired final crystal form, Form I, can be produced when using methanol or ethanol. Form II is isolated from 2-propanol and can be converted to the desired crystal form at low drying temperatures, such as between about a temperature of 40.degree. C. and 50.degree. C.
    Type: Grant
    Filed: January 20, 1998
    Date of Patent: October 12, 1999
    Assignee: Merck & Co., Inc.
    Inventors: William Clarke, Joseph L. Kukura, II
  • Patent number: 5932726
    Abstract: The present invention provides novel methods for the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1- benzoxazin-2-one of formula (VI-i) ##STR1## which is useful as a human immunodeficiency virus (HIV) reverse transcriptase inhibitor.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: August 3, 1999
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Michael Ernest Pierce, Anusuya Choudhury, Rodney Lawrence Parsons, Jr., Lilian Alicia Radesca
  • Patent number: 5922864
    Abstract: An efficient method for the preparation of a compound of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl- 1,4-dihydro-2H-3, 1-benzoxazin-2-one, also known as DMP-266, a reverse transcriptase inhibitor is achieved using a cyclization reaction of the amino alcohol intermediate with an alkyl or aryl chloroformate and a base.
    Type: Grant
    Filed: February 3, 1998
    Date of Patent: July 13, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Lisa F. Frey, Richard D. Tillyer, Edward J. J. Grabowski
  • Patent number: 5919778
    Abstract: The cyclic amide derivative is defined by the formula (I) or a salt thereof: R1-(CH2)n-Z in which R1 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## R2 being an aryl, a substituted aryl, a cycloalkyl or a heterocyclic group, m being an integer of 1 to 6, R3 being hydrogen or a lower alkyl, R4 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, R2 and R4 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: July 6, 1999
    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: 5874430
    Abstract: The present invention relates to benzoxazinones of formula I: ##STR1## or stereoisomeric forms or mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HIV reverse transcriptase, and to pharmaceutical compositions and diagnostic kits comprising the same, methods of using the same for treating viral infection or as an assay standard or reagent, and intermediates and processes for making the same.
    Type: Grant
    Filed: October 1, 1997
    Date of Patent: February 23, 1999
    Assignee: DuPont Pharmaceuticals Company
    Inventors: David Donald Christ, Anthony Joseph Cocuzza, Soo Sung Ko, Jay Andrew Markwalder, Abdul Ezaz Mutlib, Rodney Lawrence Parsons, Jr., Mona Patel, Steven Paul Seitz
  • Patent number: 5847115
    Abstract: There is disclosed an azetidinone compound of the formula ?I!: ##STR1## wherein Ring B is a benzene ring which may have substituent(s), R.sup.1 is a hydroxy-substituted lower alkyl group which may have substituent(s), X is oxygen atom and the like, Y is oxygen atom and the like, and Z is a methylene group which may have substituent(s), which is useful as a synthetic intermediate of the 1 .beta.-methylcarbapenem-type antibacterial agent.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: December 8, 1998
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Tameo Iwasaki, Kazuhiko Kondo
  • Patent number: 5831091
    Abstract: An N-?2-(1-hydroxyethyl)-3-oxopropyl!amine compound of the formula ?III!: ##STR1## wherein Ring B represents a benzene ring which may be substituted; W represents oxygen atom or sulfur atom; Y represents oxygen atom, sulfur atom or N R.sup.0, R.sup.0 represents hydrogen atom or a substituent; Z represents a substituted methylene group which contains at least one chiral center; R.sup.5 represents an aralkyloxycarbonyl group or an alkoxycarbonyl group; R.sup.6 represents hydrogen atom, an aralkyl group, an acyloxy group, a tri-substituted silyloxy group or an alkoxy group; or both of R.sup.5 and R.sup.6 bond at their termini and combine with the adjacent nitrogen atom to form phthalimido group, and a process thereof are disclosed. Said compound ?III! is useful as a starting compound of .beta.-lactam antibacterial agents.
    Type: Grant
    Filed: November 5, 1996
    Date of Patent: November 3, 1998
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Hiroshi Ohmizu, Masahiko Seki
  • Patent number: 5811423
    Abstract: Certain benzoxazinones are useful in the inhibition of HIV reverse transcriptase (including its resistant varieties), the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.
    Type: Grant
    Filed: March 12, 1997
    Date of Patent: September 22, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Steven D. Young, Linda S. Payne, Susan F. Britcher, Lekhanh O. Tran, William C. Lumma, Jr.
  • Patent number: 5767121
    Abstract: There is disclosed a pharmaceutical composition for providing antiinflammatory, antipyretic, analgesic, antiallergic, immunosuppressing or immunomodulating activity which comprises a pyridine derivative of the formula (I): ##STR1## wherein R is an optionally substituted pyridine ring, X is a oxygen atom or --S(O).sub.n --, wherein n is 0, 1 or 2, A is a bivalent C.sub.1-15 hydrocarbon residue whose branched moiety may have a substituent, Y is an oxygen or sulfur atom, R.sub.3 is a hydrogen atom or an optionally substituted hydrocarbon residue, R.sub.4 is an optionally substituted hydrocarbon residue or an optionally substituted monocyclic or bicyclic heterocyclic group, R.sub.3 and R.sub.4 may be joined together with the carbamoyl group or the thiocarbamoyl group to which they are attached to form an optionally substituted heterocyclic group, or R.sub.3 or R.sub.
    Type: Grant
    Filed: September 20, 1996
    Date of Patent: June 16, 1998
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Muneo Takatani, Taketoshi Saijo, Kiminori Tomimatsu
  • Patent number: 5756497
    Abstract: This invention relates to certain novel benzoxazinone compounds and derivatives thereof, their synthesis, and their use as oxytocin receptor antagonists. One application of these compounds is in the treatment of preterm labor in mammals, especially humans. The ability of the compounds to relax uterine contractions in mammals also makes them useful for treating dysmenorrhea and stopping labor prior to cesarean delivery.
    Type: Grant
    Filed: February 27, 1997
    Date of Patent: May 26, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Ian M. Bell, Roger M. Freidinger, Peter D. Williams
  • Patent number: 5726172
    Abstract: This invention relates to certain novel benzoxazinone compounds and derivatives thereof, their synthesis, and their use as oxytocin receptor antagonists. One application of these compounds is in the treatment of preterm labor. The ability of the compounds to relax uterine contractions in mammals also makes them useful for treating dysmenorrhea and stopping labor prior to cesarean delivery.
    Type: Grant
    Filed: January 6, 1997
    Date of Patent: March 10, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Michelle A. Sparks, Roger M. Freidinger, Debra S. Perlow, Peter D. Williams
  • Patent number: 5703075
    Abstract: This invention relates to compounds of Formula I ##STR1## which are useful in association with a pharmaceutical carrier as antiatherosclerotic agents. In addition, various compounds of Formula I are useful inhibitors of cell proliferation.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 30, 1997
    Assignee: Pharmacia & Upjohn Company
    Inventors: Ronald B. Gammill, Thomas M. Judge, Joel Morris
  • Patent number: 5703234
    Abstract: Novel process for preparing azetidinone compound of the formula ?III!: ##STR1## wherein R.sup.1 is H or lower alkyl, R.sup.2 and R.sup.3 combine together with the adjacent nitrogen to form heterocyclic group, and R.sup.4 is protected or unprotected hydroxy-substituted lower alkyl, which comprises reacting an alkanamide compound of the formula ?I!: ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are the same as defined above, with a compound of the formula ?II!: ##STR3## wherein L.sup.1 is a leaving group and R.sup.4 is the same as defined above, in the presence of a base, said compound ?Ill! being useful as synthetic intermediate for 1-methylcarbapenem derivative having excellent antibacterial activity.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 30, 1997
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Tameo Iwasaki, Kazuhiko Kondo, Hiroshi Ohmizu
  • Patent number: 5698553
    Abstract: A benzylpiperidine compound of formula I ##STR1## in which R.sup.1 is H, Hal or nitro,R.sup.2 is a benzyl group, which is unsubstituted or substituted by Hal on the aromatic portion, in the 2-, 3- or 4-position of the piperidine ring, with the proviso that R.sup.2 is not in the 4-position if X is --CO--, Y and Z are --CH.sub.2 and R.sup.1 is H,R.sup.3 is H or A,X is --O--, --S--, --NH--, --CO-- or --SO.sub.2 --,Y is --CH.sub.2 --, --NH--, --O--, --S--, --NH-- or alternatively --CO-- if X is --CO-- and Z is --NH-- or --NA--,Z is --CH.sub.2 --, --C(A).sub.2-, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CO--, --NH--, --NA--, --O--, --S-- or a bond,wherein X--Y or Y--Z is not --O--, --S--S--, --NH--O--, --O--NH--, --NH--NH--, --O--S-- or --S--O,A is alkyl having 1-6 C atoms,B is O or both H and OH, i.e.
    Type: Grant
    Filed: October 30, 1995
    Date of Patent: December 16, 1997
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Helmut Prucher, Rudolf Gottschlich, Joachim Leibrock, Harry Schwartz
  • Patent number: 5672599
    Abstract: Compounds of the formula ##STR1## wherein X is O or S--(O).sub.t ; n is one; m is zero or one; Y is CH.sub.2, O, or S--(O).sub.t provided that Y is O or S--(O).sub.t only when m is one; and A is ##STR2## are dual inhibitors of NEP and ACE. Compounds wherein A is ##STR3## are selective ACE inhibitors. Also disclosed are methods of preparation and intermediates.
    Type: Grant
    Filed: November 22, 1995
    Date of Patent: September 30, 1997
    Assignee: Bristol-Myers Squibb Co.
    Inventor: Jeffrey A. Robl
  • Patent number: 5665720
    Abstract: Certain benzoxazinones are useful in the inhibition of HIV reverse transcriptase (including its resistant varieties), the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: September 9, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Steven D. Young, Susan F. Britcher, Linda S. Payne, Lekhanh O. Tran, William C. Lumma, Jr.
  • 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: 5652237
    Abstract: This invention concerns certain 2-substituted-3,1-benzoxazin-4-ones and benzthiazinones as complement Clr protease inhibitors and antiinflammatory agents, pharmaceutical compositions containing them, methods of using them, and processes for their preparation.
    Type: Grant
    Filed: August 10, 1995
    Date of Patent: July 29, 1997
    Assignee: Warner-Lambert Company
    Inventors: Corinne Elizabeth Augelli-Szafran, Bradley William Caprathe, John Lodge Gilmore, Sheryl Jeanne Hays, Juan Carlos Jaen, Jan Ruth Penvose-Yi
  • Patent number: 5627278
    Abstract: A process for preparing compounds of the formula ##STR1## wherein X is O or S; n is one or two; m is zero or one; Y is CH.sub.2, O, or S provided that Y is O or S only when m is one; and A is ##STR2## is disclosed. Also disclosed are processes for preparing the corresponding amino intermediates.
    Type: Grant
    Filed: January 4, 1996
    Date of Patent: May 6, 1997
    Assignee: Bristol-Myers Squibb Co.
    Inventor: Jeffrey A. Robl
  • Patent number: 5624918
    Abstract: The present invention provides a phosphonic diester derivative of the following general formula (1): ##STR1## wherein A represents an oxygen atom or a sulfur atom; R.sup.1, R.sup.2, R.sup.9 and R.sup.10 are the same or different and they each represent a hydrogen atom, a lower alkoxy group, a nitro group, a lower alkyl group, a halogen-substituted lower alkyl group or a halogen atom; R.sup.3 represents a phenyl group, --B--R.sup.6 (wherein B represents an oxygen atom or a sulfur atom and R.sup.6 represents a hydrogen atom, a lower alkyl group, a cycloalkyl group, a phenyl group, a phenyl(lower)alkyl group optionally having a halogen atom as a substituent on the phenyl ring, a phenoxy(lower)alkyl group, a lower alkoxycarbonyl(lower)alkyl group, a carboxy(lower)alkyl group or a lower alkenyl group) or --NR.sup.7 R.sup.8 (wherein R.sup.7 and R.sup.
    Type: Grant
    Filed: February 5, 1995
    Date of Patent: April 29, 1997
    Assignee: Otsuka Pharmaceutical Factory, Inc.
    Inventors: Yasuhisa Kurogi, Kazuyoshi Miyata, Shizuo Nakamura, Mitsuyoshi Kondo, Takeshi Iwamoto, Chieko Naba, Yoshihiko Tsuda, Yasuhide Inoue, Jun Kanaya, Keigo Sato
  • Patent number: 5593944
    Abstract: The invention relates to new aminoaryl-1,3-oxazine-2,4-diones of the general formula (I) ##STR1## in which A, Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 have the meanings given in the description, to processes for their preparation, to new intermediates, and to their use as herbicides.
    Type: Grant
    Filed: August 2, 1994
    Date of Patent: January 14, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Hans-Joachim Santel, Markus Dollinger
  • Patent number: 5560852
    Abstract: A method of improving the light fastness of textile materials using an aqueous dispersion of a compound of formula I, ##STR1## having a first (A) and a second (B) benzoxazine-4-one ring joined by a phenylene bridging member; a variable bond between the first benzoxazine-4-one ring (A) and the phenylene bridging member, said variable bond being meta- or para- to the bond between the second benzoxazine-4-one ring (B) and the bridging member; wherein each R.sub.1 is independently hydrogen, halogen, nitro, C.sub.1-2 alkyl, C.sub.1-4 alkoxy, carboxy, sulfonic acid, C.sub.1-3 alkylcarbonyl, benzoyl or C.sub.1-4 alkoxycarbonyl and; R.sub.2 is hydrogen, chlorine, bromine, methyl, C.sub.1-2 alkoxy, phenyl, hydroxy, nitro, carboxy or sulfonic acid.
    Type: Grant
    Filed: March 22, 1995
    Date of Patent: October 1, 1996
    Assignee: Sandoz Ltd.
    Inventor: Jean-Luc Mura
  • Patent number: 5550229
    Abstract: Novel process for preparing azetidinone compound of the formula [III]: ##STR1## wherein R.sup.1 is H or lower alkyl, R.sup.2 and R.sup.3 combine together with the adjacent nitrogen to form heterocyclic group, and R.sup.4 is protected or unprotected hydroxy-substituted lower alkyl, which comprises reacting an alkanamide compound of the formula [I]: ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are the same as defined above, with a compound of the formula [II]: ##STR3## wherein L.sup.1 is a leaving group and R.sup.4 is the same as defined above, in the presence of a base, said compound [III] being useful as synthetic intermediate for 1-methylcarbapenem derivative having excellent antibacterial activity.
    Type: Grant
    Filed: June 21, 1994
    Date of Patent: August 27, 1996
    Assignee: Tanabe Seiyaku Co., Ltd.
    Inventors: Tameo Iwasaki, Kazuhiko Kondo, Hiroshi Ohmizu
  • Patent number: 5519021
    Abstract: Certain benzoxazinones are useful in the inhibition of HIV reverse transcriptase (including its resistant varieties), the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: May 21, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Steven D. Young, Susan F. Britcher, Linda S. Payne, Lekhanh O. Tran, William C. Lumma, Jr.
  • Patent number: 5508272
    Abstract: Compounds of the formula ##STR1## wherein X is O or S--(O).sub.t ; n is one or two; m is zero or one; Y is CH.sub.2, O, or S--(O).sub.t provided that Y is O or S--(O).sub.t only when m is one; and A is ##STR2## are dual inhibitors of NEP and ACE. Compounds wherein A is ##STR3## are selective ACE inhibitors. Also disclosed are methods of preparation and intermediates.
    Type: Grant
    Filed: May 5, 1994
    Date of Patent: April 16, 1996
    Assignee: Bristol-Myers Squibb Company
    Inventor: Jeffrey A. Robl
  • Patent number: 5480882
    Abstract: Compounds of formula I ##STR1## wherein R represents hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, methylene-dioxy or phenyl, which may be substituted by one or two groups independently selected from hydroxy, halogen, nitro, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy; R.sub.1 and R.sub.2 independently represent hydrogen, COOR.sub.3, --CONR.sub.4 R.sub.5, ##STR2## --OCONR.sub.4 R.sub.5, --OCOR.sub.3, --NR.sub.4 R.sub.5, --OCOOR.sub.6, --NR.sub.3 COR.sub.7, --NR.sub.CONR.sub.4 R.sub.5, --N.dbd.CH--NR.sub.4 R.sub.5, NO.sub.2, CN, OH, SR.sub.3, wherein R.sub.3 is hydrogen or C.sub.1 -C.sub.6 alkyl, R.sub.4 and R.sub.5 independently are hydrogen or C.sub.1 -C.sub.6 alkyl, R.sub.6 is C.sub.1 -C.sub.6 alkyl, and R.sub.7 is hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy, with the proviso that R.sub.1 and R.sub.2 cannot be hydrogen at the same time; X is oxygen or sulphur; Y represents a C.sub.2 -C.sub.6 alkylene chain or a C.sub.5 -C.sub.
    Type: Grant
    Filed: November 23, 1994
    Date of Patent: January 2, 1996
    Assignee: Italfarmaco S.p.A.
    Inventors: Alberto Sala, Roberto Barani, Francesca Benedini, Giorgio Bertolini, Giancarlo Dona, Gianni Gromo, Silvio Levi
  • Patent number: 5457106
    Abstract: There is disclosed a pharmaceutical composition for providing antiinflammatory, antipyretic, analgesic, antiallergic, immunosuppressing or immunomodulating activity which comprises a pyridine derivative of the formula (I): ##STR1## wherein R is an optionally substituted pyridine ring, X is a oxygen atom or --S(O).sub.n --, wherein n is 0, 1 or 2, A is a bivalent C.sub.1-15 hydrocarbon residue whose branched moiety may have a substituent, Y is an oxygen or sulfur atom, R.sub.3 is a hydrogen atom or an optionally substituted hydrocarbon residue, R.sub.4 is an optionally substituted hydrocarbon residue or an optionally substituted monocyclic or bicyclic heterocyclic group, R.sub.3 and R.sub.4 may be joined together with the carbamoyl group or the thiocarbamoyl group to which they are attached to form an optionally substituted heterocyclic group, or R.sub.3 or R.sub.
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: October 10, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Muneo Takatani, Taketoshi Saijo, Kiminori Tomimatsu
  • Patent number: 5428021
    Abstract: Novel therapeutic agents useful as inhibitors of HLE are provided. The compounds have the structural formula (I) ##STR1## wherein R.sup.1 through R.sup.9, m, n and p are as defined herein. Methods of using the compounds of formula (I) to inhibit serine proteases and to treat physiological conditions and disease states associated with elevated HLE levels are also provided, as are pharmaceutical compositions containing the compounds.
    Type: Grant
    Filed: January 27, 1994
    Date of Patent: June 27, 1995
    Assignee: SRI International
    Inventors: Charles K. Hiebert, Alan Laibelman, Kenneth J. Ryan
  • Patent number: 5362706
    Abstract: Hydantoin for the control of weeds are disclosed.
    Type: Grant
    Filed: November 9, 1992
    Date of Patent: November 8, 1994
    Assignee: Sandoz Ltd.
    Inventors: Karl Seckinger, Fred Kuhnen
  • Patent number: 5342937
    Abstract: A solvent soluble heterocyclic o-hydroxy thione carrying a lipophilic group and the process for the selective extraction of gallium, and certain other related metals, especially from solutions containing excess aluminium.
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: August 30, 1994
    Assignees: Zeneca, Limited, Nerco, Inc.
    Inventors: Peter W. Austin, Peter M. Quan, Peter A. Tasker, Derek Thorp