Chalcogen Attached Indirectly To The Bicyclo Ring System By Nonionic Bonding Patents (Class 549/58)
  • Patent number: 5550247
    Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.
    Type: Grant
    Filed: April 20, 1995
    Date of Patent: August 27, 1996
    Assignee: Hoechst Roussel Pharmaceuticals Inc.
    Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Harner, Brian S. Freed, Gregory H. Merriman
  • Patent number: 5521213
    Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: May 28, 1996
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Petpiboon Prasit, Daniel Guay, Zhaoyin Wang, Serge Leger, Michel Therien
  • Patent number: 5516909
    Abstract: A method for producing amine-boranes, specifically pyridine-borane which is highly stable and of good color is described.
    Type: Grant
    Filed: February 15, 1994
    Date of Patent: May 14, 1996
    Assignee: Boulder Scientific Company
    Inventor: Jeffrey M. Sullivan
  • Patent number: 5514817
    Abstract: Described are novel reversible photochromic phenanthropyran compounds, examples of which are substituted 2H-phenanthro 4,3-b!pyran and 3H-phenanthro 1,2-b!pyran compounds. The 2H-phenanthropyran compounds have certain substituents at the number 5 and 6 carbon atoms of the phenanthro portion of the phenanthropyran and at the 2 position of the pyran ring. Certain substituents may also be present at the number 7, 8, 9, 10, 11, or 12 carbon atoms of the phenanthro portion of the phenanthropyran. The 3H-phenanthropyran compounds have certain substituents at the number 11 and 12 carbon atoms of the phenanthro portion of the phenanthropyran and at the 3 position of the pyran ring. Certain substituents may also be present at the number 5, 6, 7, 8, 9, or 10 carbon atoms of the phenanthro portion of the phenanthropyran. Also described are polymeric organic host materials that contain or that are coated with such compounds.
    Type: Grant
    Filed: August 4, 1994
    Date of Patent: May 7, 1996
    Assignee: PPG Industries, Inc.
    Inventor: David B. Knowles
  • Patent number: 5514718
    Abstract: Compounds of formula (I), and salts and prodrugs thereof ##STR1## wherein Q.sup.1 is halo substituted phenyl; naphthyl; indolyl; benzthiophenyl; benzofuranyl; benzyl; or fluorenyl;. . is an optional covalent bond;one of X and Y is H and the other is hydroxy or C.sub.1-6 alkoxy, or X and Y are together .dbd.O or .dbd.NOR.sup.5 ;R.sup.1 and R.sup.2 are H; C.sub.1-6 alkyl optionally substituted by hydroxy, cyano, COR.sup.c, CO.sub.2 R.sup.c, CONR.sup.c R.sup.d, or NR.sup.c R.sup.d (where R.sup.c and R.sup.d are H, C.sub.1-6 alkyl or phenyl(C.sub.0-4 alkyl) optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halo and trifluoromethyl); phenyl(C.sub.1-4 alkyl) (optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halo or trifluoromethyl); COR.sup.c ; CO.sub.2 R.sup.c ; CONR.sup.c R.sup.d ; COC.sub.1-6 alkylNR.sup.c R.sup.d ; CONR.sup.c COOR.sup.d ; or SO.sub.2 R.sup.c ;R.sup.3 is H, C.sub.1-6 alkyl or C.sub.2-6 alkenyl; andR.sup.4 is phenyl optionally substituted by C.sub.1-6 alkyl, C.sub.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: May 7, 1996
    Assignee: Merck, Sharp & Dohme Limited
    Inventors: Richard T. Lewis, Kevin J. Merchant, Angus M. MacLeod
  • Patent number: 5510491
    Abstract: This invention relates to compounds of the formula: ##STR1## wherein R is an electron withdrawing group; R.sub.1 is H or COZ;X.sub.1 and X.sub.2 are independently H, lower alkyl,aryl, aryl lower-alkyl or polystyrene orR and X.sub.1 taken together with the carbon atoms to which they are attached form a ring containing from 4 to 15 ring carbon atoms and may contain up to 2 heteroatoms, wherein the heteroatoms are O, S, or N; andZ is an amino acid residue, a peptide residue or a leaving group. The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is also directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: April 23, 1996
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Michael Philbin
  • Patent number: 5508439
    Abstract: There are provided perfluoroalkanoyl aminonitrile intermediates and their use in a facile and efficient synthesis of 2-perfluoroalkyl-3-oxazolin-5-one. Said oxazolinone is a key intermediate in the preparation of insecticidal, acaricidal and nematocidal pyrrole compounds.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: April 16, 1996
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 5506262
    Abstract: Disclosed herein are compounds of structural formula (I) ##STR1## which are useful as cholesterol lowering agents. These compounds are also useful as inhibitors of squalene synthetase, inhibitors of fungal growth, inhibitors of farnesyl-protein transferase and farnesylation of the oncogene protein Ras. These compounds are also useful in the treatment of cancer.
    Type: Grant
    Filed: November 10, 1993
    Date of Patent: April 9, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Robert M. Burk, William H. Parsons, John J. Acton, III, Gregory D. Berger, Tesfaye Biftu, Robert L. Bugianesi, Yuan-Ching P. Chiang, Claude Dufresne, Narindar N. Girotra, Robert W. Marquis, Jr., Chan-Hwa Kuo, Sandra P. Plevyak, Mitree M. Ponpipom, Lori L. Whiting, James D. Bergstrom, Conrad Santini
  • Patent number: 5498630
    Abstract: A method of controlling Take-All disease of plants by applying a fungicide of the formula ##STR1## wherein Z1 and Z2 are C and are part of an aromatic ring which is benzothiophene; andA is selected from --C(X)-amine wherein the amine is an unsubstituted, monosubstituted or disubstituted amino radical, --C(O)--SR.sub.3, --NH--C(X)R.sub.4, and --C(.dbd.NR.sub.3)--XR.sub.7 ;B is --W.sub.m --Q(R.sub.2).sub.3 or selected from O-tolyl, 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R.sub.4 ;Q is C, Si, Ge, or Sn;W is --C(R.sub.3).sub.p H.sub.(2-p) --; or when Q is C, W is selected from --C(R.sub.3).sub.p H(.sub.2-p), --N(R.sub.3).sub.m H(.sub.1-m)--, --S(O)p--, and --O--;X is 0 or S;n is 0, 1, 2, or 3;m is 0 or 1;p is 0, 1, or 2;each R and R.sub.2 is independently defined herein;R.sub.3 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.4 alkyl, haloalkyl, alkoxy, alkylthio, alkylamino, or dialkylamino; andR.sub.7 is C.sub.1 -C.sub.
    Type: Grant
    Filed: November 16, 1994
    Date of Patent: March 12, 1996
    Assignee: Monsanto Company
    Inventors: Dennis P. Phillion, Diane S. Braccolino, Matthew J. Graneto, Wendell G. Phillips, Karey A. Van Sant, Daniel M. Walker, Sai C. Wong
  • Patent number: 5491152
    Abstract: The present invention provides compounds of Formula I, ##STR1## or a pharmaceutically acceptable salt forms thereof, which are inhibitors of acyl-Coenzyme A: cholesterol O-acyltransferase (ACAT), pharmaceutical compositions containing such compounds, processes for the preparation of such compounds, and the use of such compounds as antihypercholesterolemic and/or antiatherosclerotic agents.
    Type: Grant
    Filed: March 23, 1994
    Date of Patent: February 13, 1996
    Assignee: The Du Pont Merck Pharmaceutical Company
    Inventors: Richard G. Wilde, Soo S. Ko, Jeffrey T. Billheimer
  • Patent number: 5489632
    Abstract: Novel imino ether compounds, processes for their production and methods for their use are provided. These novel imino ether compounds are particularly useful as light stabilizers for polymeric compositions, particularly for lacquer coating compositions.
    Type: Grant
    Filed: July 28, 1993
    Date of Patent: February 6, 1996
    Assignee: Sandoz Ltd.
    Inventor: Lajos Avar
  • Patent number: 5488063
    Abstract: Novel 1-alkyl-, 1-alkenyl-, and 1-alkynylaryl-2-amino-1,3-propanediols, intermediates and processes for the preparation thereof, and methods of reducing inflammation and cell proliferation, and relieving memory dysfunction, and inhibiting bacterial and fungal growth are disclosed.
    Type: Grant
    Filed: May 23, 1994
    Date of Patent: January 30, 1996
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: John J. Tegeler, Barbara S. Rauckman, Russell R. L. Harmer, Brian S. Freed, Gregory H. Merriman
  • Patent number: 5484798
    Abstract: The present invention provides novel benzothiophene compounds of formula I ##STR1## wherein R is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --O--CO--(C.sub.1 -C.sub.6 alkyl), --O--CO--Ar in which Ar is optionally substituted phenyl, or --O--SO.sub.2 --(C.sub.4 -C.sub.6 alkyl);R.sup.1 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --O--CO--(C.sub.1 -C.sub.6 alkyl), --O--CO--Ar in which Ar is optionally substituted phenyl, --O--SO.sub.2 --(C.sub.4 -C.sub.6 alkyl) chloro or bromo;R.sup.2 is --H or --OH;n is 2 or 3; andR.sup.3 and R.sup.4 each are independently C.sub.1 14 C.sub.4 alkyl, or combine to form 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, or 1-hexamethyleneimino;or a pharmaceutically acceptable salt thereof, for inhibiting restenosis.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: January 16, 1996
    Assignee: Eli Lilly and Company
    Inventors: Henry U. Bryant, George J. Cullinan, Jeffrey A. Dodge, Kennan J. Fahey, Charles D. Jones
  • Patent number: 5482942
    Abstract: This invention relates to novel 4-(3,4-dioxocyclobuten-1-yl)chromenes and dihydronaphthalenones and 3-(3,4-dioxocyclobuten-1-yl)indenes and salts thereof having smooth muscle relaxing activity, to their use in the treatment of hypertension as well as for treatment of peripheral vascular disease, congestive heart failure, disorders involving excessive smooth muscle contraction of the urinary tract such as incontinence or of the gastrointestinal tract such as irritable bowel syndrome, asthma, and hair loss and to pharmaceutical compositions containing an invention compound. The present invention discloses compounds represented by the formula (I): ##STR1## wherein: R.sub.1 and R.sub.2, independent from each other, are selected from the following: C.sub.1-6 perfluoroalkoxy, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxyl, C.sub.1-6 alkoxycarbonyl, nitro, cyano, halogen, C.sub.1-6 alkylsulfonamido, C.sub.1-6 perfluoroalkylsulfonamido, amino, C.sub.1-6 acylamino, C.sub.
    Type: Grant
    Filed: June 28, 1994
    Date of Patent: January 9, 1996
    Assignee: American Home Products Corporation
    Inventors: Richard M. Soll, Paul J. Dollings
  • Patent number: 5481021
    Abstract: This invention relates to phenyl amidine derivatives having the following formula ##STR1## or a pharmaceutically acceptable salt which are useful in the inhibition of platelet aggregation. This invention also relates to pharmaceutical compositions of such phenyl amidine derivatives.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: January 2, 1996
    Assignee: G. D. Searle & Co.
    Inventors: Robert B. Garland, Masateru Miyano, Jeffery A. Zablocki, Lori A. Schretzman
  • Patent number: 5472984
    Abstract: This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: December 5, 1995
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita
  • Patent number: 5472978
    Abstract: Compounds of formula (I), and salts and prodrugs thereof, wherein Q represents optionally substituted phenyl, naphthyl, indolyl, benzothiophenyl, benzofuranyl, benzyl or indazolyl; Z represents O, S or NR.sup.8 ; X and Y are H or are together .dbd.O; R.sup.1 and R.sup.2 are H; optionally substituted C.sub.1-6 alkyl; optionally substituted phenyl(C.sub.1-4 alkyl); COR.sup.c ; CO.sub.2 R.sup.c ; CONR.sup.c R.sup.d ; CONR.sup.c COOR.sup.d ; or SO.sub.2 R.sup.c ; R.sup.3 is H or C.sub.1-6 alkyl, R.sup.4 is H , C.sub.1-6 alkyl or optionally substituted phenyl; and R.sup.5 represents optionally substituted phenyl; are tachykinin antagonists. They and compositions thereof are useful in therapy.
    Type: Grant
    Filed: December 10, 1993
    Date of Patent: December 5, 1995
    Assignee: Merck Sharp & Dohme Ltd.
    Inventors: Raymond Baker, Angus M. MacLeod, Kevin J. Merchant, Christopher J. Swain
  • Patent number: 5470999
    Abstract: Compounds of Formula 1 ##STR1## where R.sub.1 -R.sub.5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: November 28, 1995
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. Chandraratna
  • Patent number: 5464863
    Abstract: An N-heteroaryl-N'-phenylurea derivative represented by the general formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are as defined in the description of the specification which is useful as a prophylactic and therapeutic agent for hypercholesterolemia, atherosclerosis and diseases caused by them.
    Type: Grant
    Filed: September 24, 1994
    Date of Patent: November 7, 1995
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Masashi Nagamine, Kenji Yamamoto, Yoshimitsu Matsui, Kenji Horiuchi, Masanori Yoshida
  • Patent number: 5461072
    Abstract: The present invention is concerned with the use of a compound of formula (I): Ar--Y--Q, wherein Ar is either (i) furyl, thienyl, thienyl 1,1-dioxide, pyrryl, pyridyl, benzofuryl, benzothienyl, benzothienyl 1,1-dioxide, indolyl, naphthyl, quinolyl, or tetrahydronaphthyl, any of which is optionally substituted by one or more substituents independently selected from C.sub.1-4 alkyl (which may itself optionally be substituted by one or more halogen atoms), C.sub.1-4 alkoxy, halo, nitro, amino, carboxy, C.sub.1-4 alkoxy-carbonyl and hydroxy, or (ii) phenyl optionally substituted by one or more substituents independently selected from phenyl (which is itself optionally substituted by one or more substituents independently selected from those optional substituents specified in (i) above) and those specified as optional substituents in (i) above, Y is C.sub.1-10 alkylene or C.sub.2-10 alkenylene; Q is formula (II), where R.sup.1 is hydrogen, C.sub.
    Type: Grant
    Filed: October 17, 1994
    Date of Patent: October 24, 1995
    Assignee: Burroughs Wellcome Co.
    Inventor: Lawrence G. Garland
  • Patent number: 5459149
    Abstract: The present Application discloses pesticidally active compounds of formula (I):Q(CH.sub.2).sub.a (O).sub.b Q.sup.1 CR.sup.2 =CR.sup.3 CR.sup.4 =CR.sup.5 CXNR.sup.1 R.sup.xor a salt or propesticide thereof, wherein Q is an optionally substituted aromatic monocyclic or fused bicyclic ring system in which at least one ring is aromatic, or Q is a dihalovinyl group or a group R.sup.6 --C=C--where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halo or hydrogen; Q.sup.1 is a 1,2-cyclopropyl ring optionally substituted by one or more groups selected from C.sub.1-3 alkyl, halo, C.sub.1-3 haloalkyl, C.sub.2-3 alkynyl, or cyano; or Q.sup.1 is (CH.sub.2).sub.7 ; a=0 or 1; b=0 or 1; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; X is oxygen or sulphur;R.sup.1 is phenyl optionally substituted by 1-5 substituents chosen from: a) C.sub.1-4 alkyl, C.sub.
    Type: Grant
    Filed: September 20, 1994
    Date of Patent: October 17, 1995
    Assignee: Roussel Uclaf
    Inventors: John E. Robinson, George S. Cockerill
  • Patent number: 5451605
    Abstract: Compounds of the formula ##STR1## where R.sub.1 -R.sub.5 are hydrogen, lower alkyl of 1-6 carbons, or halogen; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.13 O, --COR.sub.7, CR.sub.7 (OR.sub.12).sub.2, or CR.sub.7 OR.sub.13 O, where R.sub.7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R.sub.8 is an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.10 independently are hydrogen, an alkyl group of 1 to 10 carbons, or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R.sub.11 is lower alkyl, phenyl or lower alkylphenyl, R.sub.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: September 19, 1995
    Assignee: Allergan, Inc.
    Inventors: Roshantha A. Chandraratna, Richard L. Beard
  • Patent number: 5441984
    Abstract: The present invention provides novel urea, thiourea and guanidine derivatives, pharmaceutical formulations thereof and a method of using same to prevent diabetic complications.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: August 15, 1995
    Assignee: Eli Lilly and Company
    Inventors: William F. Heath, Jr., Jill A. Panetta, John K. Shadle
  • Patent number: 5434265
    Abstract: The present invention provides novel HIV protease inhibitors, pharmaceutical formulations containing those compounds and methods of treating HIV infection.
    Type: Grant
    Filed: December 22, 1992
    Date of Patent: July 18, 1995
    Assignee: Eli Lilly and Company
    Inventors: James E. Fritz, Marlys Hammond, Stephen W. Kaldor
  • Patent number: 5426196
    Abstract: The present Invention includes synthetic steps and intermediates involved in the following reaction scheme a of converting compounds of Formula (II) to the diarylmethanes of Formula (I): ##STR1## wherein: Y is oxygen or sulfur;A, B, C, D, and E are carbon or 1, 2 or 3 of A, B, C, D, and E are independently nitrogen, and the others are carbon; andwhereinR.sup.1 through R.sup.10 are selected independently from the group consisting of: hydrogen, hydroxy, alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl alkyl, alkenyl, hydroxy alkyl, alkoxy alkyl, perhalo-alkyl, amino, nitro, nitrile, halo, carboxyl, sulfonyl, acyl, formyl, carbamoyl, trifluoromethyl, aminomethyl, azido, amido, hydrazino, aryl, aryloxy, heteroaryl, or aryl or heteroaryl, mono, di, or tri substituted with one or more hydrogen, hydroxy, alkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.
    Type: Grant
    Filed: December 22, 1993
    Date of Patent: June 20, 1995
    Assignee: Glaxo Inc.
    Inventor: Francis G. Fang
  • Patent number: 5426191
    Abstract: An improved process for the preparation of 3-chlorobenzo[b]thiophene-2-carbonyl chlorides is described where a cinnamic acid is converted in the presence of thionyl chloride and a 4-N,N'-disubstituted aminopyridine in one step to the desired product.
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: June 20, 1995
    Assignee: Warner-Lambert Company
    Inventor: Jonathan Walker
  • Patent number: 5420300
    Abstract: The subject of the invention is 2-(1-bromoethyl)benzo[b]thiophene of formula: ##STR1## as well as a process for the preparation thereof, characterised in that 2-ethylbenzo[b]thiophene is reacted, in a solvent, with a brominating agent in the presence of a free radical initiator, which provides the desired compound, and the use thereof in the preparation of 2-(1-(benzyloxyamino)ethyl)benzo[b]thiophene and of N-hydroxy-N-{1-(benzo[b]thien-2-yl)ethyl}urea.No figure.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: May 30, 1995
    Assignee: Elf Sanofi
    Inventor: Jean-Robert Dormoy
  • Patent number: 5416117
    Abstract: A novel cyclopropenone derivative (I) which possesses a potent inhibitory activity against thiol protease such as papain, cathepsin B, cathepsin H, cathepsin L, calpain or the like with excellent properties regarding oral absorbance, tissue transference and cell membrane permeability, and are clinically useful in the treatment of various diseases such as muscular dystrophy, amyotrophy. Also provided are a process for producing the compound (I) and a pharmaceutical composition containing the same.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: May 16, 1995
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
  • Patent number: 5391819
    Abstract: Disclosed herein is a process of making chiral 2-aryl-1,4-butanediamine derivatives useful as neurokinin-A antagonists of Formula 7 ##STR1##
    Type: Grant
    Filed: September 30, 1992
    Date of Patent: February 21, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Paul E. Finke, Jeffrey J. Hale, Malcolm Maccoss, Sander G. Mills
  • Patent number: 5380878
    Abstract: This invention relates to a process for producing a compound represented by formula (6a) or (6b): ##STR1## wherein R.sup.2 represents a hydrogen atom or a hydroxyl-protecting group and R.sup.4 and R.sup.5, which may be the same or different, represents lower alkyl groups, using a compound represented by formula (2a) or (2b) obtained by preferential crystallization: ##STR2## and also to a compound represented by the following formula (7) which is an intermediate useful for producing the compound of formula (6a) or (6b): ##STR3## wherein R.sup.1 represents a group represented by formula (8): ##STR4## wherein R.sup.2 and R.sup.3 is as defined above and R.sup.3 represents a hydrogen atom, a group or a carboxyl protecting group represented by formula (9): ##STR5## or a group represented by formula (10): ##STR6## wherein R.sup.2 is as defined above.
    Type: Grant
    Filed: March 29, 1994
    Date of Patent: January 10, 1995
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Joji Nakano, Nobuhisa Taya, Hisaaki Chaki, Tetsuo Yamafuji, Kaishu Momonoi
  • Patent number: 5380748
    Abstract: A trialkylamine derivative represented by the formula (1) or a pharmaceutically acceptable salt thereof: ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different from each other and each represents lower alkyl;R.sup.3, R.sup.4 and R.sup.5 may be the same or different from one another and each represents hydrogen, lower alkyl, lower alkoxy, lower alkoxycarbonyl or halogen;R.sup.6 and R.sup.7 may be the same or different from each other and each represents hydrogen or lower alkyl;R.sup.8 represents hydrogen, lower alkyl, lower alkoxy or halogen;X represents oxygen, sulfur, --CH.dbd.N-- or --CH.dbd.CH--;Y represents oxygen, sulfur, methylene, N--R.sup.11 (wherein R.sup.11 represents lower alkyl), SO or SO.sub.2 ;Z represents --OCO(CH.sub.2).sub.p .about. or --OCH.sub.2 (CH.sub.2).sub.p .about. (wherein p represents a number of 0 to 4 and symbol .about.
    Type: Grant
    Filed: August 30, 1993
    Date of Patent: January 10, 1995
    Assignee: Zeria Pharmaceutical Co., Ltd.
    Inventors: Yoshiaki Muto, Hiromi Ichikawa, Kuniyoshi Ogura, Kyoji Chaki, Masao Seiki, Toshihiko Takemasa
  • Patent number: 5376677
    Abstract: The invention relates to novel compounds of the formula ##STR1## in which R is as defined in the description, to their preparation, to fungicidal compositions which contain such compounds as active substances, and to the use of the active substances or compositions for controlling fungi in agriculture and horticulture.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: December 27, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Stephan Trah
  • Patent number: 5369158
    Abstract: Described are novel reversible photochromic naphthopyran compounds substituted at the number eight carbon atom on the naphtho portion of the naphthopyran ring with, for example, a methoxy group. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds are also described.
    Type: Grant
    Filed: June 2, 1993
    Date of Patent: November 29, 1994
    Assignee: Transitions Optical, Inc.
    Inventor: David B. Knowles
  • Patent number: 5348976
    Abstract: The present invention provides a condensed heterocyclic derivative represented by a formula: ##STR1## wherein R.sup.1 represents a lower alkyl group, an alkenyl group, or the like, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 independently represent a hydrogen atom, a lower alkyl, or the like, W is represented by --OC(O)--, --SC(O)--, or the like, and Z represents a 2-indolyl group or the like. The present invention also provides an agricultural or horticultural fungicide which comprises an amount of the condensed derivative known to be effective as a fungicide. The agricultural or horticultural fungicide according to the present invention exhibits a superior control effect for downy mildew and late blight, without harm to nonfungal, photosynthesizing plants.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: September 20, 1994
    Assignees: Kumai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masaru Shibata, Shigekazu Ito, Jun-etsu Sakai, Shigeru Hayashi
  • Patent number: 5340833
    Abstract: Disclosed are benzothiophene and thienothiophene derivatives useful for inhibiting urokinase activity.
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: August 23, 1994
    Assignee: Eisai Co., Ltd.
    Inventors: Alexander Bridges, Bruce A. Littlefield, C. Eric Schwartz
  • Patent number: 5328927
    Abstract: Compounds of formula (I), and salts and prodrugs thereof ##STR1## wherein Q.sup.1 is halo substituted phenyl; naphthyl; indolyl; benzthiophenyl; benzofuranyl; benzyl; or fluorenyl;. . is an optional covalent bond;one of X and Y is H and the other is hydroxy or C.sub.1-6 alkoxy, or X and Y are together .dbd.0 or .dbd.NOR.sup.5 ;R.sup.1 and R.sup.2 are H; C.sub.1-6 alkyl optionally substituted by hydroxy, cyano, COR.sup.c, CO.sub.2 R.sup.c, CONR.sup.c R.sup.d, or NR.sup.c R.sup.d (where R.sup.c and R.sup.d are H, C.sub.1-6 alkyl or phenyl(C.sub.0-4 alkyl) optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halo and trifluoromethyl); phenyl(C.sub.1-4 alkyl) (optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy, halo or trifluoromethyl); COR.sup.c ; CO.sub.2 R.sup.c ; CONR.sup.c R.sup.d ; COC.sub.1-6 alkylNR.sup.c R.sup.d ; CONR.sup.c COOR.sup.d ; or SO.sub.2 R.sup.c ;R.sup.3 is H, C.sub.1-6 alkyl or C.sub.2-6 alkenyl; andR.sup.4 is phenyl optionally substituted by C.sub.1-6 alkyl, C.sub.
    Type: Grant
    Filed: February 24, 1993
    Date of Patent: July 12, 1994
    Assignee: Merck Sharpe & Dohme, Ltd.
    Inventors: Richard T. Lewis, Kevin J. Merchant, Angus M. MacLeod
  • Patent number: 5328909
    Abstract: A novel cyclopropenone derivative (I) which possesses a potent inhibitory activity against thiol protease such as papain, cathepsin B, cathepsin H, cathepsin L, calpain or the like with excellent properties regarding oral absorbance, tissue transference and cell membrane permeability, and are clinically useful in the treatment of various diseases such as muscular dystrophy, amyotrophy. Also provided are a process for producing the compound (I) and a pharmaceutical composition containing the same.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: July 12, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Yasuhiro Morinaka, Chizuko Takahashi, Yoshikuni Tamao, Akihiro Tobe
  • Patent number: 5326759
    Abstract: Novel 9-amino-7-(substituted amino)-6-demethyl-6-deoxytetracyclines having activity against a wide spectrum of organisms including organisms which are resistant to tetracyclines are disclosed. Also disclosed are intermediates and methods for making the novel compounds of the present invention.
    Type: Grant
    Filed: November 1, 1993
    Date of Patent: July 5, 1994
    Assignee: American Cyanamid Company
    Inventors: Joseph J. Hlavka, Phaik-Eng Sum, Yakov Gluzman, Ving J. Lee
  • Patent number: 5326783
    Abstract: This invention is directed to compounds of formula (I) which are novel C3- or C5-acyl sulfonamide, carboxamic acid or tetrazolyl analogs of the Zaragozic acids. These compounds inhibit the enzyme squalene synthase and are useful as cholesterol lowering agents.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: July 5, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Tesfaye Biftu, Chan-Hwa Kuo, Conrad Santini
  • Patent number: 5314910
    Abstract: 2-Heteroaromatic alkanoate esters which are useful as inhibitors of human leukocyate or neutrophil elastase.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: May 24, 1994
    Assignee: Cortech Inc.
    Inventors: Gary P. Kirschenheuter, Raymond T. Cunningham, John C. Cheronis
  • Patent number: 5302704
    Abstract: Dyes of formula ##STR1## wherein D is the radical of a diazo component of the benzene or naphthalene series or of the heterocyclic series, R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl and R.sub.2 is phenyl or substituted phenyl, give dyeings of good fastness properties on nitrogen-containing or hydroxyl group containing fibre materials.
    Type: Grant
    Filed: August 3, 1992
    Date of Patent: April 12, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean-Marie Adam, Thomas Eichenberger
  • Patent number: 5296612
    Abstract: A process for producing an enyne derivative, and intermediate, which is useful for preparing compounds showing strong inhibiting activities against squalane epoxidase of Eumycetes and strong anti-cholesterol activities. The process comprises reacting a compound of the formula: ##STR1## wherein W is a halogen atom, with an acetylene derivative, in the presence of a palladium catalyst, to obtain a compound of the formula: ##STR2## and, if necessary, N-alkylating this compound.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: March 22, 1994
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • Patent number: 5292894
    Abstract: A process for the preparation of benzo[b]thiophenes of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 independently denote hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro, cyano, halo, C.sub.1 -C.sub.4 alkylcarbonyl, benzoyl, C.sub.1 -C.sub.4 alkylcarbonylamino, benzoylamino,N-(C.sub.1 -C.sub.4 alkyl)phenylamino, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylsulfonyl, phenylsulfonyl, aminosulfonyl, aminocarbonyl, C.sub.1 -C.sub.4 phenylalkyl and nitrobenzyl or R.sup.1 +R.sup.2 or R.sup.2 +R.sup.3 or R.sup.3 +R.sup.4 denote a butadienediyl chain optionally substituted by R.sup.1 to R.sup.4, in whicha) thiophenols of the general formula II ##STR2## in which the substituents R.sup.1 to R.sup.4 have the aforementioned meanings, are reacted with chloroacetaldehyde at a temperature ranging from 0.degree. to 150.degree. C. andb) the resulting (arylthio)acetaldehydes of the general formula III ##STR3## in which the substituents R.sup.
    Type: Grant
    Filed: February 17, 1993
    Date of Patent: March 8, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ebel, Juergen Schroeder
  • Patent number: 5288749
    Abstract: The present invention provides tertiary and secondary amine compounds of the formula ##STR1## and the pharmaceutically acceptable salts thereof which are antagonists for alpha-2 adrenoreceptors and which inhibit serotonin (5-hydroxytryptamine, 5-HT) uptake.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: February 22, 1994
    Assignee: Abbott Laboratories
    Inventors: Michael D. Meyer, John F. DeBernardis, Rajnandan Prasad, Kevin B. Sippy, Karin R. Tietje
  • Patent number: 5286881
    Abstract: A benzodifuranone compounds of the formula, ##STR1## wherein R.sup.1 and R.sup.2 are each independently a naphthyl group or an unsubstituted or substituted phenyl group, which is useful for dyeing or printing hydrophobic fiber materials, is prepared in high purity and high yield by allowing benzofuran compounds of the formula, ##STR2## wherein R.sup.1 is as defined above, to react with acetonitrile compounds of the formula, ##STR3## wherein R.sup.2 is as defined above, and then carrying out an oxidation reaction to give the benzodifuranone compound.
    Type: Grant
    Filed: September 30, 1992
    Date of Patent: February 15, 1994
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Junichi Sekihachi, Jun Yamamoto, Yutaka Kayane
  • Patent number: 5284868
    Abstract: A pharmaceutical compound of the formula ##STR1## in which n is 0, 1 or 2 and R.sup.1 is attached at any of the positions 5, 6, 7, 8, 9 or 10, and each R.sup.1 is halo, trifluoromethyl, C.sub.1-4 alkoxy, hydroxy, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkylthio, hydroxy-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkoxy, trifluoromethoxy, carboxy, --COOR.sup.5 where R.sup.5 is an ester group, --CONR.sup.6 R.sup.7 or --NR.sup.6 R.sup.7 where R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl; R.sup.2 is phenyl, naphthyl or heteroaryl selected from thienyl, pyridyl, benzothienyl, quinolinyl, benzofuranyl or benzimidazolyl, said phenyl, naphthyl and heteroaryl groups being optionally substituted, or R.sup.2 is furanyl optionally substituted with C.sub.1-4 alkyl; R.sup.3 is nitrile, carboxy, --COOR.sup.8 where R.sup.8 is an ester group, --CONR.sup.9 R.sup.10 where R.sup.9 and R.sup.10 are each hydrogen or C.sub.1-4 alkyl, or R.sup.11 SO.sub.2 -- where R.sup.11 is C.sub.1-4 alkyl or optionally substituted phenyl; and R.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: February 8, 1994
    Assignees: Eli Lilly and Company, Lilly Industries Limited
    Inventors: Colin P. Dell, Jai P. Singh, Colin W. Smith
  • Patent number: 5258401
    Abstract: Disclosed herein are compounds of structural formula (I) ##STR1## which are useful as cholesterol lowering agents. These compounds are also useful as inhibitors of squalene synthase, inhibitors of fungal growth, inhibitors of farnesyl-protein transferase and farnesylation of the oncogene protein Ras. These compounds are also useful in the treatment of cancer.
    Type: Grant
    Filed: September 10, 1992
    Date of Patent: November 2, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Gregory D. Berger, Robert W. Marquis, Jr., Albert J. Robichaud, Edward M. Scolnick
  • Patent number: 5258400
    Abstract: New furanone compounds have anti-inflammatory, immunosuppresive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis. A compound of the invention is 4-[3,6-dihydro-6-hydroxy-5-(3-phenylpropyl)-2H-pyran-2-yl]-5-hydroxy-2-(5H )-furanone.
    Type: Grant
    Filed: April 23, 1992
    Date of Patent: November 2, 1993
    Assignee: Allergan, Inc.
    Inventors: Michael E. Garst, Elizabeth T. Syage
  • Patent number: 5258360
    Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, wherein R.sup.1 and R.sup.2, which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, --NR.sup.3 --, or --CR.sup.4 R.sup.5 --; X, Y and Z.sup.1, which are the same or different, are, for example, hydrogen, halogen, hydroxy, optionally substituted alkyl, cycloalkyl or aryl among other possible substituents or X and Y when they are in adjacent positions on the ring optionally form a fused ring; and R, R.sup.3 -R.sup.12 are, for example, hydrogen or optionally substituted alkyl among other possible substituents provided R.sup.4 and R.sup.5 are not both hydrogen. The compounds are useful in agriculture, especially as fungicides but also as insecticides and plant growth regulators.
    Type: Grant
    Filed: July 21, 1992
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul deFraine, Christopher R. A. Godfrey, Kevin Beautement
  • Patent number: RE34770
    Abstract: Amine derivatives having the general formula (I): ##STR1## wherein X is selected from the group consisting of ##STR2## Y is selected from the group consisting of ##STR3## R.sup.1 is hydrogen atom or an alkyl group; R.sup.2 is hydrogen atom or an alkyl group; R.sup.3 is hydrogen atom, a halogen atom or an alkyl group; R.sup.4 is hydrogen atom, an alkyl group, a cycloalkyl group, a halogenated alkyl group or a halogen atom; R.sup.5 is hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, nitro group or hydroxy group; R.sup.5 is attached to an arbitrary position of X, and R.sup.3 or R.sup.4 is attached to an arbitrary position of Y.The amine derivatives (I) are useful as fungicides.
    Type: Grant
    Filed: May 21, 1993
    Date of Patent: November 1, 1994
    Assignee: Kaken Pharmaceutical Co., Ltd.
    Inventors: Tetsuya Maeda, Toshiyuki Yamamoto, Mituo Takase, Kazuya Sasaki, Tadashi Arika, Mamoru Yokoo, Rieko Hashimoto, Kouji Amemiya, Sakae Koshikawa