Chalcogen Attached Directly To The Bicyclo Ring System By Nonionic Bonding Patents (Class 549/51)
  • 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: 5512684
    Abstract: The invention provides a process for preparing 6-alkoxy-3-(4-alkoxyphenyl)benzo B!thiophenes in good yield on a manufacturing scale without generating a thick, potentially yield-reducing, paste. The invention also provides methods for converting a-(-alkoxyphenylthio)-4-alkoxyacetophenones into 6-hydroxy-2-(4-hydroxyphenyl)-3- 4-(2-aminoethoxy)benzoyl!benzo B!thiophen es via acylation of a dialkoxy benzo B!thiophene. Each of these preparations relies on an intramolecular cyclization of a dialkoxy acetophenone derivative to yield a benzo B!thiophene without generating a thick paste that lowers overall yields on a manufacturing scale.
    Type: Grant
    Filed: August 8, 1995
    Date of Patent: April 30, 1996
    Assignee: Eli Lilly and Company
    Inventor: Charles A. Alt
  • Patent number: 5510379
    Abstract: .beta.-Carboxy sulfonates of the formula ##STR1## wherein R.sub.1 is aryl, R.sub.3 and R.sub.4 are hydrogen or alkyl, Y is -O-, -S-, or -NR.sub.2 -, and R.sub.5 is alkyl or aryl are potent inhibitors of the enzyme acyl CoA:cholesterol acyltransferase (ACAT) and are thus useful for treating hypercholesterolemia and atherosclerosis.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: April 23, 1996
    Assignee: Warner-Lambert Company
    Inventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
  • Patent number: 5510498
    Abstract: The present invention provides compounds of formula II ##STR1## wherein R.sup.1a is --H or --OR.sup.7 in which R.sup.7 is a hydroxy protecting group;R.sup.2a is --H, halo, or --OR.sup.8 in which R.sup.8 is a hydroxy protecting group, providing when Z is --S--, R.sup.2a is not halo;R.sup.6 is --H or a hydroxy protecting group which can be selectively removed; andZ is --O-- or --S--;or a pharmaceutically acceptable salt thereof, which are useful intermediates for the preparation of biologically active compounds.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: April 23, 1996
    Assignee: Eli Lilly and Company
    Inventor: Alan D. Palkowitz
  • Patent number: 5508450
    Abstract: Benzopyran derivatives which have an inhibitory effect on the Maillard reaction as well as an antioxidizing effect are described herein. These derivatives may be utilized in the treatment and/or prevention of diabetic complications such as, for example, coronary heart disease, peripheral circulatory insufficiency or failure, cerebrovascular hindrance, neurogenous diabetes, nephropathy, arteriosclerosis, arthrosclerosis, cataracts and retinopathy. Further, the derivatives may also be used in the treatment and/or prevention of diseases induced by aging and in the treatment and/or prevention of diseases caused by the formation of peroxidized fat.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: April 16, 1996
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Shuichi Ohuchida, Masaaki Toda, Tsumoru Miyamoto
  • 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: 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: 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: 5472962
    Abstract: A benzothiophene derivative represented by the formula ##STR1## or a salt thereof has an excellent antiestrogenic activity, and is useful as a therapeutic agent of breast cancer, endometrial cancer, endometriosis, mastopathy, etc.This compound is characterized in that the 2-position (the substituent R.sup.2) of the benzothiophene nucleus is substituted by a halogen atom; a lower alkyl group; or a cycloalkyl or cycloalkenyl group optionally substituted by a lower alkyl group, a hydroxyl group, acyloxy group or an oxo group.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: December 5, 1995
    Assignee: Teikoku Hormone Mfg. Co., Ltd.
    Inventors: Naoyuki Koizumi, Shigehiro Takegawa, Shigeki Iwashita, Tomoko Kawachi, Teruaki Matsui, Mamoru Mieda, Hiroo Takahashi, Tomoyuki Saito, Kenyu Shibata
  • Patent number: 5470854
    Abstract: The invention relates to new furans and thiophenes with the general Formula 1, ##STR1## in which R.sup.1 and R.sup.2 independently of one another denote a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a benzyl group, a group C(O)R.sup.4, where R.sup.4 is an alkyl or alkoxy group having 1 to 10 carbon atoms or a phenyl radical, or a carbamoyl group --C(O)NR.sup.5 R.sup.6, where R.sup.5 and R.sup.6 independently of one another are a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and n denotes an integer from 0 to 12 if R.sup.3 is a hydrogen atom, or n denotes an integer from 4 to 12 if R.sup.3 is an amino group --NR.sup.7 R.sup.8, where R.sup.7 and R.sup.8 independently of one another represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms or R.sup.7 and R.sup.8 together represent an alkylene group --(CH.sub.2).sub.m -- or the group --(CH.sub.2).sub.2 -- or R.sup.3 denotes an amide group --C(O)NR.sup.7 R.sup. 8, where R.sup.7 and R.sup.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: November 28, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Erwin von Angerer, Sebastian Erber, Martin Schneider
  • Patent number: 5466810
    Abstract: A group of 2-amino-3-aroyl-benzo[.beta.]thiophenes are prepared by treating an aldehyde with an anion of dimethylamino thioformamide, cyclizing the .alpha.-hydroxy thioamide, and subsequently acylating the benzo[.beta.]thiophene to yield the 2-amino-3-aryl derivative. These compounds may be treated with suitable phenyl Grignard reagents, and after deprotection, yield 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[.beta .]thiophene.
    Type: Grant
    Filed: June 10, 1994
    Date of Patent: November 14, 1995
    Assignee: Eli Lilly and Company
    Inventor: Alexander G. Godfrey
  • Patent number: 5464834
    Abstract: New N-substituted N'-heterobicyclic piperazines corresponding to the general formula I: ##STR1## wherein: R represents: ##STR2## D represents a single bond, except when R represents naphthyl, or a hydrocarbon chain having 1 to 8 carbon atoms inclusive which is straight-chain or branched by a gem-dimethyl; andA-B represents: --(CH.sub.2).sub.2 --O--, --(CH.sub.2).sub.3 --O--, or --CO--CH.dbd.CH--,as well as their possible stereoisomers, epimers, and pharmaceutically-acceptable acid addition salts thereof; and medicinal products containing the same, useful in the treatment of a disorder requiring a 5-HT.sub.1A receptor antagonist.
    Type: Grant
    Filed: June 11, 1993
    Date of Patent: November 7, 1995
    Assignee: Adir et Compagnie
    Inventors: Jean-Louis Peglion, Bertrand Goument, Mark Millan, Jean-Michel Rivet
  • Patent number: 5440049
    Abstract: A compound of the formula: ##STR1## wherein R.sup.11 is hydrogen, lower alkyl, haloloweralkyl, lower alkenyl, lower alkynyl or cycloalkyl and R.sup.21 is a group selected from the group consisting of: ##STR2## wherein R.sup.3 -R.sup.5, R.sup.31, R.sup.32, R.sup.41, R.sup.42 and R.sup.51 are as defined herein, and W is chlorine or bromine, is prepared by reacting a compound of the formula:Z--CH.sub.2 --CH.dbd.CH--W (I)wherein W is as defined above and Z is a leaving group, with an amine of the formula: ##STR3## wherein R.sup.11 and R.sup.21 are as defined above.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: August 8, 1995
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • Patent number: 5385931
    Abstract: The invention relates to new sulphonamide derivatives of benzo-cyclic or benzo-heterocyclic acids and their derivatives of general formula I ##STR1## in which: R represents a straight-chain or branched lower alkyl radical having 1 to 9 C;a phenyl radical which is unsubstituted or substituted by one or more groups:straight-chain or branched lower alkyl having 1 to 4 C, halogeno, alkoxy, nitro, amino, dialkylamino or CF.sub.3 ;a substituted or unsubstituted naphthalene;a thiophenyl radical;R.sub.1 represents a hydrogen or a straight-chain or branched lower alkyl or a benzyl;R.sub.2 represents a hydrogen, a straight-chain or branched lower alkyl group, a substituted or unsubstituted phenyl group or an aralkyl group;R.sub.3 represents a hydrogen or a straight-chain or branched lower alkyl (1 to 6 C);--X-- represents a divalent functional radical chosen from the following: --CH.sub.2 --; ##STR2## where R.sub.
    Type: Grant
    Filed: December 28, 1990
    Date of Patent: January 31, 1995
    Assignee: Pierre Fabre Medicament
    Inventors: Dennis Bigg, Alain Duflos, Jean-Pierre Rieu
  • Patent number: 5380750
    Abstract: The invention relates to a compound selected from those of formula (I): ##STR1## in which Ar', R.sub.1 and R.sub.2 are as defined in the specification, an optical isomer,and an addition salt thereof with a pharmaceutically-acceptable acid or base.Medicinal product which is useful in treating or in preventing a disorder of the melatoninergic system.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: January 10, 1995
    Assignee: Adir et Compagnie
    Inventors: Daniel Lesieur, Said Yous, Patrick Depreux, Jean Andrieux, Gerard Adam, Daniel H. Caignard, Beatrice Guardiola
  • Patent number: 5378699
    Abstract: Methods of treating an immune disease, cell proliferation, restenosis and vascular smooth muscle cells using the pharmaceutical compounds of the formula ##STR1## in which 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; and salts thereof.
    Type: Grant
    Filed: February 5, 1993
    Date of Patent: January 3, 1995
    Assignees: Lilly Industries Limited, Eli Lilly and Company
    Inventors: Michael Brunavs, Colin P. Dell, Peter T. Gallagher, William M. Owton, Jai P. Singh, Colin W. Smith
  • Patent number: 5359091
    Abstract: A compound of the formula: ##STR1## wherein R.sup.11 is hydrogen, lower alkyl, haloloweralkyl, lower alkenyl, lower alkynyl or cycloalkyl; R.sup.21 is a group of the formula: ##STR2## wherein each of R.sup.3, R.sup.31, and R.sup.32 which may be the same or different, is hydrogen or lower alkyl, each of R.sup.4, R.sup.5, R.sup.41 and R.sup.51, which may be the same or different, is hydrogen, halogen, hydroxyl, lower alkyl or lower alkoxy, R.sup.42 is hydroxyl, halogen, R.sup.8 --O--, or R.sup.6 --X--Y-- wherein R.sup.6 is phenyl or thienyl which may have one or two substituents each of X and Y, which may be the same or different, is oxygen, sulfur, carbonyl, --CHR.sup.8 -- or --NR.sup.b, or X and Y together form a vinylene group or an ethynylene group, provided that when either one of X and Y is oxygen, sulfur or --NR.sup.b, the other is carbonyl or --CHR.sup.a, and R.sup.
    Type: Grant
    Filed: November 18, 1993
    Date of Patent: October 25, 1994
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • 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: 5334333
    Abstract: The present invention relates to electroactive compounds capable of undergoing a change in light absorption and refraction due to an applied electric field and a permanent change in refraction due to exposure to predetermined bands of optical radiation. The present invention also relates to electroactive compositions containing such electroactive compounds, electrooptical components comprised of such electroactive compositions and electrooptical devices comprised of such electrooptical components, as well as novel processes of making the same.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: August 2, 1994
    Assignee: Elf Atochem North America, Inc.
    Inventor: Frederick J. Goetz
  • 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: 5304657
    Abstract: A hydrazine compound of the formula (I) or its salt: ##STR1## wherein A is a benzofuranyl group which may be substituted, a quinolinyl group which may be substituted, a benzothienyl group which may be substituted, a benzothiazolyl group which may be substituted, a thienothienyl group which may be substituted, a dihydrothienothienyl group which may be substituted, a dihydrocyclopentathienyl group which may substituted, a tetrahydrobenzothienyl group which may be substituted, an indanyl group which may be substituted, or a hexahydroindanyl group which may be substituted, W is a hydrogen atom, a cyano group, --COCOOR', --S--N(R")COOR' or --CH.sub.
    Type: Grant
    Filed: October 10, 1991
    Date of Patent: April 19, 1994
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Tadaaki Toki, Toru Koyanagi, Kiyomitsu Yoshida, Kazuhiro Yamamoto, Masayuki Morita
  • Patent number: 5294375
    Abstract: Disclosed is a class of bridged phthalides and sulfinate esters which exhibit reversible thermochromism. At room temperature and in the presence of base, these compounds are substantially colorless but upon the application of heat they become colored, reverting to their original colorless or weakly colored state upon cooling. This colorless to colored, temperature-dependent cycle can be repeated many times. These compounds have utility as temperature sensors and as thermal pH indicators.
    Type: Grant
    Filed: August 20, 1991
    Date of Patent: March 15, 1994
    Assignee: Polaroid Corporation
    Inventors: Marcis M. Kampe, David P. Waller, David C. Whritenour
  • 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: 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: 5280032
    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: September 8, 1992
    Date of Patent: January 18, 1994
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita
  • Patent number: 5254595
    Abstract: Aryloxypropanolaminotetralins with beta-antagonist activity of the formula ##STR1## wherein R is hydrogen, hydroxy or methoxy and Ar is an optionally substituted aromatic or heteroaromatic group, in optically active or inactive form as well as their acid addition salts are described.A process for their preparation and pharmaceutical compositions containing the compounds of formula (i) or their pharmaceutically acceptable acid addition salts, are also described.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: October 19, 1993
    Assignee: Elf Sanofi
    Inventors: Umberto Guzzi, Marco Baroni, Sergio Boveri, Luciano Manara, Alberto Bianchetti
  • Patent number: 5252749
    Abstract: The compounds of the invention having the formula: ##STR1## in which: A, which is a ring condensed with cyclopentane, represents a substituted or unsubstituted thiophene ring, Q represents an alkylene chain, R.sub.1 and R.sub.2 each represent H or an alkyl, or they form, with the nitrogen atom to which they are linked, a saturated nitrogenous heterocyclic ring containing 5 to 7 atoms, R.sub.3 and R.sub.4 each represent H, alkyl, cycloalkyl, trifluoromethyl or an optionally substituted phenyl, thienyl or furyl group or R.sub.3 and R.sub.4 together form a (C.sub.5 -C.sub.8) cycloalkyl, as well as their addition salts with an acid and their quaternary ammonium derivatives.They can be used as medicines.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: October 12, 1993
    Assignee: Elf Sanofi
    Inventors: Alain Badorc, Jean Courregelongue, Daniel Ducros, Daniel Frehel, Antonina Giudice, Claudine Serradeil-Legal
  • Patent number: 5250565
    Abstract: Pro-drugs of potent 5-lipoxygenase inhibiting compounds comprise compounds of the formula ##STR1## in which A is an alkylene or alkenylene group, X is oxygen, sulfur, sulfoxyl, or substituted nitrogen, and Y is a group which includes substituted or unsubstituted carbocyclic or substituted or unsubstituted heterocyclic aryl. R.sup.1 is an alkyl, alkenyl, amino, alkylamino, dialkylamino, or hydroxyamino group or an amine group bearing a metabolically cleavable leaving group. M is hydrogen, a pharmaceutically acceptable cation or a metabolically cleavable leaving group, with the proviso that either M or R.sup.1 must bear a metabolically cleavable leaving group.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: October 5, 1993
    Assignee: Abbott Laboratories
    Inventors: Dee W. Brooks, James B. Summers
  • Patent number: 5225569
    Abstract: The process of the invention comprises reacting a C-22-halo-23,24-bisnorsteroid or C-22-halo-23,24-bisnor-9,10-secosteroid with a nickel complex of an electron withdrawing alkene of the formula ##STR1## wherein R.sub.1 is hydrogen, hydroxycarbonyl, lower alkoxycarbonyl, lower alkylcarbonyl or unsubstituted or substituted lower alkyl, and R.sub.2 is hydroxyl, lower alkoxy, or unsubstituted or substituted lower alkyl,to yield a C-25 or C-26 precursor of the formula ##STR2## which is appropriately functionalized for conversion into the corresponding steroid or secosteroid by treatment as hereinafter described.
    Type: Grant
    Filed: October 1, 1992
    Date of Patent: July 6, 1993
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George P. Yiannikouros, Percy S. Manchand
  • Patent number: 5217989
    Abstract: Non-peptidyl compounds characterized generally as benzothiophenyl/benzothiophenylalkyl-N-terminal cycloalkoxy-C-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from ##STR2## wherein each of Y and Z is independently selected from hydrido, chloro, fluoro, methoxy and dimethylamino; wherein X is sulfur atom; wherein n is a number selected from zero through four, inclusive; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 and R.sub.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: June 8, 1993
    Assignee: G. D. Searle & Co.
    Inventor: Gunnar J. Hanson
  • Patent number: 5194446
    Abstract: Methods of treating chronic arthritis and osteoporosis which utilize both known and novel compounds which would fall under the general formula:(HO)p--A--[--OS(O).sub.2 NR.sup.1 R.sup.2 ].sub.zwherein A encompasses a wide range of values including but not limited to aryl, loweralkyl, cycloalkyl, and carbohydrates including sucrose and fructose; p is equal to the number of unreacted hydroxy groups contained on the molecule and may be zero; z is the number of --OS(O).sub.2 NR.sup.1 R.sup.2 groups and is always at least one; R.sup.1 and R.sup.2 are selected from hydrogen, loweralkyl, carboxy and the like; a novel process for preparing the compounds is provided wherein an appropriate sulfamic acid aryl ester is reacted with a hydroxy substituted A radical which may or may not contain thereon protected carboxyl, amino or hydroxy substituents, in an aprotic solvent containing a tertiary amine base. Pharmaceutical compositions for the treatment of chronic arthritis and osteoporosis are also provided.
    Type: Grant
    Filed: July 24, 1991
    Date of Patent: March 16, 1993
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Young S. Lo, Joseph C. Nolan, William J. Welstead, Jr., David A. Walsh, Dwight A. Shamblee, Ibrahim M. Uwaydah
  • Patent number: 5187284
    Abstract: A compound of the formula: ##STR1## in which X, Y and Z are, independently, hydrogen, halogen, hydroxy, nitro, cyano, carboxyl, trifluoromethyl, phenyl, amino, alkylamino, dialkylamino, alkyl or alkoxy; R.sub.1 is hydrogen, alkyl, alkenyl, cycloalkyl, phenyl, benzyl or substituted phenyl or benzyl or alkoxy; or a pharmaceutically acceptable salt thereof are ACAT inhibitors.
    Type: Grant
    Filed: July 22, 1992
    Date of Patent: February 16, 1993
    Assignee: American Home Products Corporation
    Inventors: William F. Fobare, Donald P. Strike
  • Patent number: 5187192
    Abstract: Compounds of the structure ##STR1## where M is a pharmaceutically acceptable cation or a metabolically cleavable group, R is alkyl, cycloalkyl or --NR.sup.1 R.sup.2, where R.sup.1 and R.sup.2 are hydrogen, alkyl, cycloalkyl or alkanoyl, and A is optionally substituted alkyl, cycloalkyl, carbocyclic aryl, benzo[b]furyl, thienyl, or benzo[b]thienyl are potent inhibitors of lipoxygenase enzymes and thus inhibit the biosynthesis of leukotrienes. These compounds are useful in the treatment or amelioration of allergic and inflammatory disease states.
    Type: Grant
    Filed: March 13, 1992
    Date of Patent: February 16, 1993
    Assignee: Abbott Laboratories
    Inventors: Dee W. Brooks, Karen E. Rodriques
  • Patent number: 5175314
    Abstract: This invention relates to certain herbicidal oxatricyclic ethers, agriculturally suitable compositions thereof and a method for their use as broad spectrum preemergent or postemergent herbicides.
    Type: Grant
    Filed: January 8, 1992
    Date of Patent: December 29, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Wendy S. Taylor
  • Patent number: 5169860
    Abstract: This invention provides the use of certain benzofuransulfonamide, benzothiophenesulfonamide, and indolesulfonamide derivatives in the treatment of susceptible neoplasms in mammals. Also provided are certain novel benzofuransulfonamide and benzothiophenesulfonamide derivatives and their pharmaceutical formulations.
    Type: Grant
    Filed: March 13, 1992
    Date of Patent: December 8, 1992
    Assignee: Eli Lilly and Company
    Inventors: Fariborz Mohamadi, Michael M. Spees
  • Patent number: 5162364
    Abstract: A compound of formula (I): ##STR1## in which R, R.sub.1 and R.sub.2 are as defined in the description. Medicinal product, which is useful in treating disorders related to a dysfunction of GABA.sub.B receptors.
    Type: Grant
    Filed: June 11, 1991
    Date of Patent: November 10, 1992
    Assignee: Adir et Compagnie
    Inventors: Michel Debaert, Pascal Berthelot, Claude Vaccher
  • Patent number: 5153194
    Abstract: A thienocycloheptapyridazine compound of the formula ##STR1## wherein R stands for hydrogen, a halogen or a C.sub.1-4 alkyl, Ar stands for an aryl, a heteroaryl, or an aryl or a heteroaryl having as a substituent at least a halogen, a C.sub.1-4 alkyl, a C.sub.1-4 alkoxy, nitro, amino, hydroxy, trifluoromethyl and/or a C.sub.2-5 alkanoylamino; and the bond between 4-position and 42-position represents a single bond or a double bond, which is useful as an antianxiety agent, amnesia-treating drug, a brain function-activating drug or an antidementiac drug.
    Type: Grant
    Filed: May 17, 1990
    Date of Patent: October 6, 1992
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Tohru Nakao, Hiroshi Tanaka, Yasuto Morimoto, Shuzo Takehara
  • Patent number: 5126461
    Abstract: Process for ring opening compounds of the formula ##STR1## in which R.sup.1 is heteroaryl or aryl, R.sup.2 is a leaving group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, alkyl, aralkyl, aryl, heteroaryl and alkenyl, provided that at least one of the groups R.sup.3 to R.sup.6 is other than hydrogen, by breaking the bond joining the carbon atom attached to R.sup.3 and the carbon atom attached to R.sup.6 in organic solution using silica, giving useful diene or allyl derivatives, certain of which are novel.
    Type: Grant
    Filed: November 14, 1990
    Date of Patent: June 30, 1992
    Assignee: Shell Research Limited
    Inventors: Mark S. Baird, Ian Bruce
  • Patent number: 5116874
    Abstract: This invention provides certain N-[(phenyl)amino]carbonyl-bicyclicsulfonamide sulfonamide derivatives, their pharmaceutical formulations, and their use in the treatment of susceptible neoplasms in mammals.
    Type: Grant
    Filed: May 15, 1989
    Date of Patent: May 26, 1992
    Assignee: Eli Lilly and Company
    Inventor: Gerald A. Poore
  • Patent number: 5112851
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 represents a group of formula ##STR2## and R.sub.2 represents hydrogen or lower alkyl, orR.sub.1 and R.sub.2 together with the carbon atom to which they are attached represent a group of formula IIg ##STR3## R.sub.4 and R.sub.5 represents independently hydrogen or lower alkyl, R.sub.3 represents hydrogen, alkyl, cycloalkyl or halogenalkyl andR.sub.6 represents a group of formula ##STR4## R.sub.1 represents a group of formula IIa to IIf as defined above, R.sub.2 and R.sub.3 together form a --(CH.sub.2)--.sub.u group wherein u stands for a whole number from 1 to 8 and R.sub.4, R.sub.5 and R.sub.6 have the meanings given above,which compounds are indicated for use as pharmaceuticals and agrochemicals.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: May 12, 1992
    Assignee: Sandoz Ltd.
    Inventors: Anton Stutz, Peter Nussbaumer
  • Patent number: 5112852
    Abstract: The present invention relates to allenyl amines, more specifically, .beta.-ethenylidene(substituted) ethanamines, possessing antihypertensive activity, and having the general formula ##STR1## wherein n is the integer 0, 1 or 2; each X independently is a substituent selected from the group consisting of loweralkyl, halo, --O--(loweralkyl), --S--(loweralkyl), --SO--(loweralkyl), --SO.sub.2 --(loweralkyl), CO.sub.2 R and CH.sub.2 OR, wherein R is loweralkyl and each loweralkyl group is from 1 to about 6 carbon atoms, or the pharmaceutically-acceptable addition salts thereof. These compounds are prepared by a novel reaction of a protected N,N-bis(trimethylsilyl)-4-methoxy-2-butynylamine compound with a metallo-organic compound, with subsequent removal of the silyl protecting groups to provide the desired compound.
    Type: Grant
    Filed: April 21, 1989
    Date of Patent: May 12, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: James R. McCarthy, Thomas M. Bargar, Charlotte L. Barney, Donald P. Matthews, Robert J. Broersma
  • Patent number: 5110829
    Abstract: 2,2'-Thienylbenzothiophenes of the general formula I ##STR1## where R.sup.1 and R.sup.3 independently of one another are each halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, R.sup.2 is hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, n is 0, 1 or 2, and the radicals may be different when n is 2, and m is 0, 1, 2, 3 or 4, and the radicals may be different when m is 2, 3 or 4, processes for their preparation, pesticides containing them and the use thereof.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: May 5, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Reiner Kober, Hans Theobald, Uwe Kardorff, Christoph Kuenast, Peter Hofmeister, Rainer Seele, Gerhard Wagenblast
  • Patent number: 5071841
    Abstract: The present invention provides a sulfur-containing heterocyclic compound of the formula (I) ##STR1## wherein ring A is a benzene ring which may be substituted; R is a hydrogen atom or a hydrocarbon group which may be substituted; B is a carboxyl group which may be esterified or amidated; X is --CH(OH)-- or --CO--; k is 0 or 1; and k' is 0, 1 or 2 or a pharmaceutically acceptable salt thereof.Also, it provides a process for producing the compound (I) or a salt thereof and a pharmaceutical preparation for use in the treatment of osteoporosis comprising the compound (I) or salt thereof.The compounds (I) and salts thereof show excellent bone resorption inhibitory activity.
    Type: Grant
    Filed: December 28, 1989
    Date of Patent: December 10, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Takashi Sohda, Masao Tsuda, Iwao Yamazaki
  • Patent number: 5026724
    Abstract: A method is provided for treating patients suffering from or susceptible to bronchoconstriction, particularly for patients suffering from an asthmatic attach which comprises the use of benzothiophene, benzofuran, dihydronaphthalene or indene derivatives represented by formula I ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is independently H, (1-4C) alkyl, (1-4C) halogen substituted alkyl, OH, (1-4C) alkoxy, (1-4C) halogen substituted alkoxy, NO.sub.2, CN, halogen, an unsubstituted or (1-4C) alkyl substituted amino group, or wherein two adjacent groups R.sup.1, R.sup.2, R.sup.3 or R.sup.4 together form methylenedioxy;X is S, O or (CH.sub.2).sub.m in which m is 1 or 2;R.sup.5 is H or (1-4C) alkyl;R.sup.6 is H, NH.sub.2 or (1-4C) alkyl;R.sup.7 is H, (1-4C) alkyl or OR.sup.8 in whichR.sup.8 is H, (1-4C) alkyl or (1-8C) acyl;and its pharmaceutically acceptable salts for the preparation of a medicament with bronchodilator activity.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: June 25, 1991
    Assignee: Akzo N.V.
    Inventors: Robert T. Logan, James Redpath, George McGarry, Robert G. Roy
  • Patent number: 5004813
    Abstract: Chromogenic phthalides and azaphthalides of the formula ##STR1## in which V.sub.1 and V.sub.2 are each, independently of the other, hydrogen, halogen, lower alkyl, lower alkoxy, (lower alkoxy)carbonyl or --NR.sub.1 R.sub.2, at least one of the radicals V.sub.1 and V.sub.2 being lower alkoxy or --NR.sub.1 R.sub.2, A is an unsubstituted or halogen-, cyano-, nitro-, (lower alkyl)-, (lower alkoxy)-, (lower alkyl)thio-, (lower alkyl)amino- or di(lower alkyl)amino-substituted benzene, naphthalene, pyridine, quinoline, pyrazine or quinoxaline ring, B is a substituted phenyl radical of the formula ##STR2## or a 3-indolyl of the formula ##STR3## Q is ##STR4## --S-- or --O--, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each, independently of the others, hydrogen, unsubstituted or halogen-, hydroxy-, cyano- or (lower alkoxy)-substituted alkyl, cycloalkyl or unsubstituted or ringsubstituted phenalkyl or phenyl, or the substituent pairs (R.sub.1 and R.sub.2) and (R.sub.3 and R.sub.
    Type: Grant
    Filed: August 24, 1989
    Date of Patent: April 2, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Rox Phaff, Davor Bedekovic
  • Patent number: 4997956
    Abstract: This invention provides bicyclic carboxylic esters and amides, their pharmaceutical formulations, and a method for their use in treating migraine, emesis, gastrointestinal disorders, schizophrenia, or anxiety in mammals.
    Type: Grant
    Filed: January 24, 1990
    Date of Patent: March 5, 1991
    Assignee: Eli Lilly and Company
    Inventor: William B. Lacefield
  • Patent number: 4963580
    Abstract: Position-4 and/or position-6 substituted 5-hydroxy-2,3-dihydrobenzothiophenes and analogs of the following general structural formula (I) are disclosed: ##STR1## These compounds are found to be potent inhibitors of leukotriene biosynthesis.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: October 16, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Robert A. Zambias, Milton L. Hammond
  • Patent number: 4952602
    Abstract: Biphenyl derivative of the formula: ##STR1## wherein R.sup.1 is hydrogen atom or a lower alkoxycarbonyl group and R.sup.2 is a lower alkoxycarbonyl group, or R.sup.1 and R.sup.2 are combined together to form a group of the formula: each of R.sup.3 and R.sup.4 is a lower alkoxy group; and Ring A is a substituted or unsubstituted sulfur-containing or nitrogen-containing heterocyclic ring, with the claims being drawn to Ring A as thiophene and a pharmaceutically acceptable salt thereof are disclosed. Said biphenyl derivative (I) and its salt have excellent hypolipidemic activity and are useful for treatment or prophylaxis of hyperlipidemia and/or arterioscelerosis.
    Type: Grant
    Filed: November 8, 1988
    Date of Patent: August 28, 1990
    Assignee: Tanabe Seiyaku Company, Ltd.
    Inventors: Tameo Iwasaki, Kohki Takashima