Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Bicyclo Ring System Patents (Class 549/405)
  • Patent number: 5393775
    Abstract: A compound selected from those of formula (I): ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and n are as defined in the description, its optical isomers, and its addition salts thereof with a pharmaceutically-acceptable acid or base,and medicinal product containing the same for treating a mammal afflicted with a disorder connected with peroxydation processes and biosynthesis of eicosanoids.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: February 28, 1995
    Assignee: Adir et Compagnie
    Inventors: Guillaume Le Baut, Jean-Paul Babingui, Sylvie Robert-Piessard, Pierre Renard, Daniel-henri Caignard, jean-Francois Renaud de la Faverle, Gerard Adam
  • 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: 5378726
    Abstract: A novel hydrazine derivative and a pesticidal composition containing the hydrazine derivative as the effecting ingredient. The hydrazine derivative show high pesticidal activity against harmful pests which are resistant to known pesticides such as organophosphorus pesticides, pyrethroids, etc., especially against Lepidopters harmful pests such as Plutella xylostella, Spodoptera litura, Cnaphalocrocis medinalis, Adoxophyes orana, etc., and is effective for controlling harmful pests in paddy field, upland field, orchard, forest or places to be kept environmentally hygienic.
    Type: Grant
    Filed: November 15, 1993
    Date of Patent: January 3, 1995
    Assignees: Nippon Kayaku Kabushiki Kaisha, Sankyo Company, Limited
    Inventors: Mikio Yanagi, Hiroyasu Sugizaki, Tetsuya Toya, Yasuhito Kato, Hidetoshi Shirakura, Tetsuo Watanabe, Yoshimi Yajima, Seiichirou Kodama, Akio Masui, Toshiaki Yanai, Yoshihisa Tsukamoto, Yoshihiro Sawada, Shinji Yokoi
  • 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: 5324743
    Abstract: This invention provides certain 1,2,4,5 substituted benzene derivatives containing "acid" substituents derived from cyclic or heterocyclic moieties. These unique compounds are leukotriene B.sub.4 antagonists and formulations of these derivatives, and a method of using these derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.
    Type: Grant
    Filed: December 10, 1992
    Date of Patent: June 28, 1994
    Assignee: Eli Lilly and Company
    Inventors: Robert D. Dillard, J. Scott Sawyer, Michael J. Sofia
  • Patent number: 5318987
    Abstract: Lipid-selective antioxidants of the formula I(A).sub.a (L)(X).sub.a, (I),in whichA=an antioxidative component,L=a bridging member,X=a lipophilic componenta and a'=independently of one another the numbers 1 or 2.The compounds are used for the protection of lipid-containing substances against oxidation and in pharmaceuticals for the prophylaxis and treatment of diseases in which bioradicals are involved, in particular of coronary, circulatory and vascular diseases.
    Type: Grant
    Filed: January 7, 1991
    Date of Patent: June 7, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Klaus-Ulrich Weithmann, Gunther Wess, Dirk Seiffge
  • Patent number: 5310951
    Abstract: This invention relates to compounds of Formula I and the stereoisomers and pharmaceutically acceptable salts thereof ##STR1## wherein R is alkyl, alkenyl, alkynyl, or cycloalkylalkyl;R.sup.1 is alkyl;R.sup.2 is hydrogen, alkyl;R.sup.6 is alkyl;n is 1 to 5;p is 0 to 6;x is 0 or 2; andR.sup.4 and R.sup.5 are independently hydrogen or alkyl or together with N form a cycloalkylamine.The compounds of Formula I are leukotriene B.sub.4 antagonists and are useful as anti-inflammatory agents and in treating disease conditions mediated by LTB.sub.4.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: May 10, 1994
    Assignee: G.D. Searle & Co.
    Inventors: Stevan W. Djuric, Stephen H. Docter, Stella S. Yu
  • Patent number: 5300522
    Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen. acyl, lower-alkyl or --CHO, --CH.sub.2 OR.sup.10, --COR.sup.7 or OR.sup.13 ; R.sup.2, R.sup.3 and R.sup.4 are, independently, hydrogen, lower-alkyl, lower-alkoxy or halogen; R.sup.5 and R.sup.5 are, independently, hydrogen or lower-alkyl; R.sup.7 is hydroxy, lower-alkoxy or NR.sup.8 R.sup.9 ; R.sup.8 and R.sup.9 are, independently, hydrogen or lower-alkyl; X and Y are, independently, >CR.sup.14 R.sup.15, --O--, --S--, >SO, >SO.sub.2 or >NR.sup.18 ; R.sup.10 and R.sup.18 are, independently, hydrogen, lower-alkyl or acyl; M is --C(R.sup.11).dbd.C(R.sup.12)--, --CONH-- or --NH--CO--; R.sup.11, R.sup.12, R.sup.14 and R.sup.15 are, independently, hydrogen or lower-alkyl, R.sup.
    Type: Grant
    Filed: August 18, 1992
    Date of Patent: April 5, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
  • Patent number: 5223510
    Abstract: The subject of the invention is benzofuran, benzothiophene, indole or indolizine compounds of general formula: ##STR1## in which: Het represents one of the groups: ##STR2## in which T,T' and T"represent particularly a group: ##STR3## R and R.sub.a, identical or different, represent X represent --O-- or --S--Y represents a radical ##STR4## These compounds are useful as medecines particularly for the treatment of pathological syndroms of the cardio-vascular system.
    Type: Grant
    Filed: July 26, 1991
    Date of Patent: June 29, 1993
    Assignee: Sanofi
    Inventors: Jean Gubin, Pierre Chatelain, Jean Lucchetti, Gilbert Rosseels, Henri Inion
  • Patent number: 5214164
    Abstract: The present invention relates to chemical substances having dye properties, or more particularly, to improved cyanine dyes and to their application in photographic bleaching processes. Preferably, a chromylium group on the hetero ring comprises either a substituted phenyl group or an alkyl group. More particularly, O-halogenated phenyl and t-butyl groups have proven to be advantageous substituents.
    Type: Grant
    Filed: December 19, 1989
    Date of Patent: May 25, 1993
    Assignees: Herbert Kubler, Karl-Heinz Drexhage
    Inventors: Karl-Heinz Drexhage, Elisabeth Drexhage
  • Patent number: 5155240
    Abstract: A process for producing an optically active dihydropyran derivative represented by formula (1): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 each represents a hydrogen atom, a lower alkyl group, a tri-lower alkylsilylmethyl group, a lower alkoxycarbonylamino group, or an --OR.sup.5 group, wherein R.sup.5 represents a lower alkyl group, a lower acyl group, a lower alkoxycarbonyl group, a di-lower alkylcarbamoyl group, or a tri-lower alkylsilyl group, or R.sup.1 and R.sup.2 are taken together to form a 5- to 7-membered cyclic hydrocarbon group or to form a condensed heterocyclic group with an oxygen atom, or R.sup.2 and R.sup.3 are taken together to form a 5- to 7-membered cyclic hydrocarbon group or to form a condensed heterocyclic group with an oxygen atom, provided that all of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 do not represent hydrogen atoms at the same time; and R.sup.6 represents a lower alkyl group, which comprises reacting a diene compound represented by formula (2): ##STR2## wherein R.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: October 13, 1992
    Assignee: Takasago International Corporation
    Inventors: Koichi Mikami, Masahiro Terada, Takeshi Nakai, Noboru Sayo
  • Patent number: 5155130
    Abstract: The invention relates to the compounds of the formula ##STR1## wherein each R independently represents hydrogen, lower alkyl, halogen, trifluoromethyl, lower alkoxy, carbocyclic or heterocyclic aryl, carbocyclic or heterocyclic aryloxy, carbocyclic or heterocyclic aryl-lower alkyloxy, carbocyclic or heterocyclic aryl-lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl-lower alkyloxy, or C.sub.3 -C.sub.7 -cycloalkyloxy; R.sub.1 represents hydrogen, lower alkyl or carbocyclic aryl; R.sub.2 represents hydrogen or lower alkyl; Y represents oxygen (O), sulfur (S), sulfinyl or sulfonyl; n represents 1, 2 or 3; A represents a direct bond or lower alkylene; Z represents ##STR2## wherein R.sub.3 represents hydrogen or acyl; R.sub.4 represents lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl, carbocyclic or heterocyclic aryl, carbocyclic or heterocyclic aryl-lower alkyl, or C.sub.3 -C.sub.7 -cycloalkyl-lower alkyl; or Z represents ##STR3## wherein X represents oxygen or sulfur, R.sub.
    Type: Grant
    Filed: October 10, 1990
    Date of Patent: October 13, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: James L. Stanton, Yoshitaka Satoh, Alan J. Hutchison
  • Patent number: 5134159
    Abstract: Retinoid like activity is exhibited by compounds of the formula ##STR1## wherein the R.sub.1 -R.sub.6 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl of 1 to 6 carbons; X symbolizes an ester or thioester linkage, Y is lower branched chain alkyl having 2 to 6 carbons, cycloalkyl having 3 to 6 carbons or is (CH.sub.2).sub.n where n is an integer between 0 to 6 or is an alkenyl group of 2 to 6 carbons, and having 1 or 2 double bonds, or an alkynyl group of 2 to 6 carbons; and Z is H, OH, OR', OCOR', --COCH or a pharmaceutically acceptable salt, COOR.sub.8, COONR.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), CHOR.sub.13 O, --COR', CR'(OR.sub.12).sub.2, or CR'OR.sub.13 O; where R' is an alkyl cycloalkyl or alkenyl group containing 1-5 carbons, R.sub.8 is an alkyl group of 1-10 carbons, or a cycloalkyl group of 5-10 carbons, or R.sub.8 is phenyl or lower alkylphenyl, R.sub.9 and R.sub.
    Type: Grant
    Filed: March 26, 1991
    Date of Patent: July 28, 1992
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5124350
    Abstract: This invention relates to compounds of Formula I and the stereoisomers and pharmaceutically acceptable salts thereof ##STR1## wherein R is alkyl, alkenyl, alkynyl, or cycloalkylalkyl;R.sup.1 is alkyl;R.sup.2 is hydrogen or alkyl;R.sup.6 is alkyl;n is 1 to 5;p is 0 to 6;x is 0 or 2; andR.sup.4 and R.sup.5 are independently hydrogen or alkyl or together with N form a cycloalkylamine.The compounds of Formula I are leukotriene B.sub.4 antagonists and are useful as anti-inflammatory agents and in treating disease conditions mediated by LTB.sub.4.
    Type: Grant
    Filed: June 28, 1990
    Date of Patent: June 23, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Stephen H. Docter, Stella S. Yu
  • Patent number: 5039672
    Abstract: Certain spirocyclic heterocyclic compounds, and their pharmaceutically-acceptable salts, are inhibitors of the aldose reductase enzyme, and so are useful for the control of diabetic complications. Exemplary compounds include compounds of the formula ##STR1## wherein Y is ##STR2## X is --O-- or ##STR3## R.sub.1 and R.sub.2 are each independently H, alkyl C.sub.1 -C.sub.6,aryl or arylalkyl (C.sub.1 -C.sub.6);W.sub.1 and W.sub.2 are each independently hydrogen, halogen or nitro; andthe pharmaceutically acceptable base addition salts thereof.
    Type: Grant
    Filed: April 5, 1990
    Date of Patent: August 13, 1991
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Eric R. Larson
  • Patent number: 5010104
    Abstract: Novel tricyclic compounds having a TXA.sub.2 -antagonizing activity represented by formul (I): ##STR1## which strongly antagonize an action of thromboxane A.sub.2 and are expected to have preventive and therapeutic effects on ischemica diseases, cerebro-vascular diseases, etc.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: April 23, 1991
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Etsuo Oshima, Hiroyuki Obase, Akira Karasawa, Kazuhiro Kubo, Ichiro Miki, Akio Ishii
  • Patent number: 5006550
    Abstract: Retinoid like activity is exhibited by compounds of the formula ##STR1## wherein the R.sub.1 -R.sub.7 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl of 1 to 6 carbons; X symbolizes an ester or thioester linkage, Y is cycloalkyl or branched chain alkyl of 1 to 6 carbons or is (CH.sub.2) where n is an integer between 0 to 6 or is an alkenyl group of 2 to 6 carbons, or an alkynyl group of 2 to 6 carbons; and Z is H, OH, OR', OCOR', --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR' or a ketal derivative where R' is an alkyl, cycloalkyl or alkenyl group containing 1 to 6 carbons, or a phenylalkyl, phenyl or substituted phenyl group.
    Type: Grant
    Filed: December 29, 1989
    Date of Patent: April 9, 1991
    Assignee: Allergan, Inc.
    Inventor: Roshantha A. S. Chandraratna
  • Patent number: 5003090
    Abstract: The invention is directed to a process and intermediates for the preparation of benzopyrans such as racemic-6-acetyl-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyloxy]-3, 4-dihydro-2H-1-benzopyran-2-carboxylic acid.
    Type: Grant
    Filed: March 19, 1990
    Date of Patent: March 26, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Percy S. Manchand, Robert A. Micheli
  • Patent number: 4983633
    Abstract: Amide-compounds represented by the formula (I): ##STR1## wherein R.sub.1 represents hydrogen, lower alkoxy, hydroxy, lower alkyl, halogen, amino which can be substituted by lower alkyl, nitro, cyano, sulfamoyl which can be substituted by lower alkyl, R.sub.2 represents hydrogen, lower alkoxy, hydroxy, lower alkyl, halogen, amino, nitro, wherein R.sub.1 and R.sub.2 can be combined to form methylenedioxy, R.sub.3 means hydrogen, lower alkyl, halogen, or amino, R.sub.4 and R.sub.5 may be the same or different and each represents lower alkyl or wherein R.sub.4 and R.sub.
    Type: Grant
    Filed: September 2, 1988
    Date of Patent: January 8, 1991
    Assignee: Hokuriku Pharmaceutical Co., Ltd.
    Inventors: Yasuo Itoh, Hideo Kato, Eiichi Koshinaka, Nobuo Ogawa, Hiroyuki Nishino, Jun Sakaguchi
  • Patent number: 4971982
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, halogen, trifluoromethyl, nitro, cyano, lower alkyl, lower alkoxycarbonyl, lower alkylthio, lower alkylsulphonyl, lower alkanoyl, aroyl, carbamoyl, mono(lower alkyl)carbamoyl or di(lower alkyl)carbamoyl, R.sup.2 is hydrogen, lower alkyl or phenyl, R.sup.3 is hydrogen or lower alkyl, R.sup.4 and R.sup.5 each is hydrogen or R.sup.4 is hydroxy and R.sup.5 is hydrogen or R.sup.4 and R.sup.5 together are a carbon-carbon bond and R.sup.6 is an aryl or N-heteroaryl group carrying a hydroxy group in the 2-position or, in the case of a N-heteroaryl group, also a N-oxide group in the 2-position, and pharmaceutically acceptable acid addition salts of these compounds of formula I which are basic, possess pronounced potassium channel activating activity and can be used as medicaments, particularly in the control or prevention of hypertension, congestive heart failure, angina pectoris, peripheral and cerebral vascular disease and smooth muscle disorders.
    Type: Grant
    Filed: June 23, 1988
    Date of Patent: November 20, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael R. Attwood, Philip S. Jones, Sally Redshaw
  • Patent number: 4950766
    Abstract: A method for preparing a benzamide by reacting an aromatic acid with an amine having a primary amino group and a secondary amino group wherein the reaction is directed to the primary amino group by first reacting the acid with N,N'-carbonyldiimidazole.
    Type: Grant
    Filed: September 21, 1989
    Date of Patent: August 21, 1990
    Assignee: Erbamont, Inc.
    Inventor: Jung-Hui Sun
  • Patent number: 4935441
    Abstract: Compounds of the formula I ##STR1## wherein rings A and B are each unsubstituted or substituted; Y is oxygen, sulfur, sulfinyl or sulfonyl; one of the symbols Z.sub.1 and Z.sub.2 is halogen and the other formyl; and pharmaceutically acceptable salts of such compounds that contain a salt-forming group are useful for the treatment of diseases of the respiratory tract and of liver diseases. They are prepared by methods known per se.
    Type: Grant
    Filed: May 28, 1986
    Date of Patent: June 19, 1990
    Assignee: Zyma SA
    Inventor: Christian G. Rimbault
  • Patent number: 4931574
    Abstract: The invention is directed to a process and intermediates for the preparation of benzopyrans such as racemic-6-acetyl-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyloxy]-3,4-d ihydro-2H-1-benzopyran-2-carboxylic acid.
    Type: Grant
    Filed: August 23, 1988
    Date of Patent: June 5, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Percy S. Manchand, Robert A. Micheli
  • Patent number: 4889871
    Abstract: This invention encompasses compounds of Formula 1 and the pharmaceutically acceptable salts thereof. ##STR1## wherein R.sup.1 represents alkyl having 2-6 carbon atoms;R.sup.2 represents methyl or ethyl;R.sup.3 represents alkyl having 1 to 5 carbon atoms;W represents (CH.sub.2).sub.x where x is 2 to 7, alkylene having 2 to 7 carbon atoms, alkenylene having 3 to 7 carbon atoms, alkynylene having 3 to 7 carbon atoms, or cyclopentyl;R.sup.4 represents hydrogen, alkyl having 2-5 carbon atoms, alkenyl having 2 to 5 carbon atoms, or alkynyl having 2 to 5 carbon atoms;Q represents oxygen or CH.sub.2 ;B represents CH.sub.2, C.dbd.O or CH--OH;R.sup.5 represents hydrogen, alkyl having 1 to 6 carbon atoms, or R.sup.5 and R.sup.6 together optionally represent a carbon to carbon bond; orR.sup.5 represents alkanoyl having 2 to 4 carbon atoms, carboxy, alkoxycarbonyl, or (CH.sub.2)y--CO.sub.2 R.sup.8 wherein y is 0 to 4 and R.sup.8 is hydrogen or alkyl having 1 to 6 carbon atoms; andA represents --Z--CO.sub.2 R.sup.
    Type: Grant
    Filed: May 12, 1988
    Date of Patent: December 26, 1989
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Robert L. Shone, Stella S. T. Yu
  • Patent number: 4841078
    Abstract: Bicyclic fused benzenoid compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, where M is O, CH.sub.2 or NR.sub.6 ; R.sub.6 is hydrogen, formyl, carbobenzyloxy or certain carboalkoxyalkyl, alkanoyl, alkyl, aralkyl or aralkylcarbonyl groups;A' is:(1) A where one of A and B is hydrogen such that when A is hydrogen, B is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 1 or 2; when B is hydrogen, A is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 0 or 1, when taken together A and OR.sub.1 form a lactone or certain derivatives thereof;(2) A' is ##STR2## (3) A' is Q.sub.3 ; Q is CO.sub.2 R.sub.7, COR.sub.8, C(OH)R.sub.8 R.sub.9, CN, CONR.sub.12 R.sub.13, CH.sub.2 NR.sub.12 R.sub.13, CH.sub.2 NHCOR.sub.14, CH.sub.2 NHSO.sub.2 R.sub.17 or 5-tetrazoyl;Q.sub.3 is ##STR3## 5-tetrazolyl, CH.sub.2 CONHCOR.sub.7, COOH or certain ester, amide, carboximido or sulfonimido derivatives thereof, CONHOH, CONHCONH.sub.2, or COCH.sub.2 Q.sub.4 where Q.sub.
    Type: Grant
    Filed: August 9, 1984
    Date of Patent: June 20, 1989
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Michael R. Johnson, Lawrence Sherman
  • Patent number: 4829080
    Abstract: An aromatic benzopyranyl or benzothiopyranyl compound of the formula ##STR1## wherein n is 0 or 1,X represents ##STR2## R' represents H, OH, acyloxy or NH.sub.2, R" represents H or alkoxy orR' and R" taken together form an oxo, methano or hydroxyimino radical,R.sub.8 represents H, ##STR3## R.sub.9 represents H, alkyl, mono or polyhydroxyalkyl, aryl, aralkyl, a residue of a sugar or ##STR4## p equals 1, 2 or 3, r' and r" represent H, alkyl, monohydroxyalkyl, polyhydroxyalkyl, aryl, benzyl, the residue of an amino acid or an aminated sugar, or together form a heterocycle,R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represents H or lower alkyl,R.sub.5, R.sub.6 and R.sub.7 represent H or methyl or when n=1, R.sub.5 and R.sub.7 taken together form with the benzene ring a naphthalene ring (R.sub.5 -R.sub.7 .dbd.--CH.dbd.CH--), andthe salts of said compounds as well as their geometric and optical isomers.These compounds are useful in pharmaceutical and cosmetic compositions.
    Type: Grant
    Filed: March 12, 1987
    Date of Patent: May 9, 1989
    Assignee: L'Oreal
    Inventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle, Braham Shroot
  • Patent number: 4788214
    Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or lower alkyl; R.sup.2 is hydrogen or halogen; R.sup.3, R.sup.4 and R.sup.5 are hydrogen, acyl or lower alkyl; R.sup.6 and R.sup.7, independently, are hydrogen or lower alkyl; X is alkylene.sub.3-7 ; and n is an integer of zero to four; provided that only one of R.sup.3, R.sup.4 or R.sup.5 can be acyl;enatiomers thereof, and, when R.sup.7 is hydrogen, salts thereof with pharmaceutically acceptable bases.The compounds of formulas I and II are useful as agents for the treatment of allergic conditions.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: November 29, 1988
    Assignee: Hoffman-La Roche Inc.
    Inventors: Noal Cohen, Giuseppe F. Weber
  • Patent number: 4785017
    Abstract: The invention relates to compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or lower alkyl; R.sup.2 is hydrogen or halogen; R.sup.3, R.sup.4 and R.sup.5 are hydrogen, acyl or lower alkyl; R.sup.6 and R.sup.7, independently, are hydrogen or lower alkyl; X is alkylene.sub.3-7 ; and n is an integer of zero to four; provided that only one of R.sup.3, R.sup.4 or R.sup.5 can be acyl;enantiomers thereof, and, when R.sup.7 is hydrogen, salts thereof with pharmaceutically acceptable bases.The compounds of formulas I and II are useful as agents for the treatment of allergic conditions.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: November 15, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Giuseppe F. Weber
  • Patent number: 4778903
    Abstract: The invention relates to compounds of the formula: ##STR1## which are useful as leukotriene D.sub.4 (LTD.sub.4) inhibitors and therefore useful in the treatment of allergies and inflammatory conditions.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: October 18, 1988
    Assignee: G. D. Searle & Co.
    Inventors: Masateru Miyano, Robert L. Shone, Daniel D. Sohn
  • Patent number: 4728650
    Abstract: There are provided novel 3,4-dihydrobenzopyran derivatives having anti-peptic ulcer, antitussive and/or expectorant activity. Also provided are medicinal uses of said 3,4-dihydrobenzopyran derivatives.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: March 1, 1988
    Assignee: Kuraray Co., Ltd.
    Inventors: Katsushi Eziri, Koichi Kanehira, Manzo Shiono, Yoshiji Fujita, Johji Yamahara
  • Patent number: 4713393
    Abstract: Phenylalkyl-2,3-dihydrobenzofurans and analogs were prepared by (1) nucleophilic substitution involving an appropriately substituted 2,3-dihydrobenzofuranol (or 2,3-dihydrobenzopyranol) and a cinnamylhalide followed by reduction; or (2) by Wittig reaction involving a halomethyl derivative of 2,3-dihydrobenzofuran (or 2,3-dihydrobenzopyran and an aryl or a heteroaryl aldehyde followed by reduction. These compounds were found to be potent anti-inflammatory agents.
    Type: Grant
    Filed: April 25, 1985
    Date of Patent: December 15, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Kathryn L. Thompson, David A. Boulton
  • Patent number: 4686235
    Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: August 11, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
  • Patent number: 4680404
    Abstract: Bicyclic fused benzenoid compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, where M is O, CH.sub.2 or NR.sub.6 ; R.sub.6 is hydrogen, formyl, carbobenzyloxy or certain carboalkoxyalkyl, alkanoyl, alkyl, aralkyl or aralkylcarbonyl groups;A' is:(1) A where one of A and B is hydrogen such that when A is hydrogen, B is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 1 or 2; when B is hydrogen, A is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 0 or 1, when taken together A and OR.sub.1 form a lactone or certain derivatives thereof;(2) A' is ##STR2## (3) A' is Q.sub.3 ; Q is CO.sub.2 R.sub.7, COR.sub.8, C(OH)R.sub.8 R.sub.9, CN, CONR.sub.12 R.sub.13, CH.sub.2 NR.sub.12 R.sub.13, CH.sub.2 NHCOR.sub.14, CH.sub.2 NHSO.sub.2 R.sub.17 or 5-tetrazoyl;Q.sub.3 is ##STR3## 5-tetrazolyl, CH.sub.2 CONHCOR.sub.7, COOH or certain ester, amide, carboximido or sulfonimido derivatives thereof, CONHOH, CONHCONH.sub.2, or COCH.sub.2 Q.sub.4 and Q.sub.
    Type: Grant
    Filed: August 9, 1984
    Date of Patent: July 14, 1987
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4617314
    Abstract: Benzofuran- and benzopyran-carboxamide derivatives of the formula: ##STR1## wherein l is 1 or 2; X is hydrogen atom, amino group or halogen atom; Y is --S(O).sub.m --R.sup.3 wherein R.sup.3 is lower alkyl group and m is 0, 1 or 2, or ##STR2## wherein R.sup.4 and R.sup.5 are the same or different and are each hydrogen atom or lower alkyl group; R.sup.1 is hydrogen atom, lower alkyl group, arylthiomethyl group, halogenomethyl group or ##STR3## wherein R.sup.6 and R.sup.7 are the same or different and are each hydrogen atom or lower alkyl group or R.sup.6 and R.sup.7 together with the adjacent nitrogen atom form a hetrocycle; R.sup.2 is hydrogen atom or lower alkyl group; and Z is ##STR4## wherein p is 2 or 3, R.sup.8 and R.sup.9 are the same or different and are each lower alkyl group or R.sup.8 and R.sup.9 together with the adjacent nitrogen atom form a heterocycle, or ##STR5## wherein q is 0 or 1, n is 1 or 2, R.sup.
    Type: Grant
    Filed: March 20, 1984
    Date of Patent: October 14, 1986
    Assignee: Yoshitomi Pharmaceutical Industries Ltd.
    Inventors: Tetsuya Tahara, Kiyoharu Hayano, Michihide Setoguchi, Takemi Fukuda
  • Patent number: 4617407
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.
    Type: Grant
    Filed: August 30, 1984
    Date of Patent: October 14, 1986
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Joshua Rokach
  • Patent number: 4587342
    Abstract: Novel 2,4-diaminopyrimidines having substituted heterobicyclomethyl moieties in the 5-position have superior antibacterial properties.
    Type: Grant
    Filed: October 31, 1983
    Date of Patent: May 6, 1986
    Inventors: Susan M. Daluge, Paul M. Skonezny
  • Patent number: 4565882
    Abstract: The invention relates to substituted dihydrobenzopyrans carboxylates of the formula: ##STR1## wherein A is a methylene chain having 1-10 carbon atoms, inclusive, optionally substituted by hydroxy;wherein V is:(a) hydrogen;(b) hydroxy;(c) .dbd.O; or(d) R.sub.6 CH.sub.2 O--;wherein R.sub.1 is:(a) --COCH.sub.3 ;(b) --CHOHCH.sub.3 ;(c) --C.sub.2 H.sub.5 ;(d) -hydrogen; or(e) --COOC.sub.2 H.sub.5wherein R.sub.2 is:(a) -hydrogen;(b) -hydroxy; or(c) R.sub.12 CH.sub.2 CO.sub.2 --;wherein R.sub.3, R.sub.4, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 each of which may be the same or different, are:(a) hydrogen;(b) lower-alkyl having 1-6 carbon atoms inclusive; or(c) allyl;wherein R.sub.5 is:(a) hydrogen; or(b) R.sub.7 CH.sub.2 C(O)--;wherein R.sub.13 is hydrogen, hydroxy, alkoxy of 1 to 6 carbon atoms inclusive, or --OM wherein M is an alkali metal, alkyl of 1 to 6 carbon atoms, inclusive, or NR.sub.8.sup..sym. R.sub.9 R.sub.10 R.sub.11, or HNR.sub.8.sup..sym. R.sub.9 R.sub.
    Type: Grant
    Filed: January 6, 1984
    Date of Patent: January 21, 1986
    Assignee: G. D. Searle & Co.
    Inventors: Masateru Miyano, Robert L. Shone
  • Patent number: 4547579
    Abstract: There are described novel dyes of the formulae ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, and R.sub.1 and R.sub.2 together with the nitrogen atom, and optionally with the inclusion of further hetero atoms, can also form a 5- to 7-membered heterocycle, or one of the radicals R.sub.1 or R.sub.2 can be linked with the carbon atoms, in the o-position with respect to the amino group, of the ring A to form a fused-on, saturated, unsubstituted or substituted 5- or 6- membered ring,X is .dbd.NR.sub.3, .dbd.NCOR.sub.4, ##STR2## .dbd.NH or .dbd.O, wherein R.sub.3 is alkyl or unsubstituted or substituted phenyl,R.sub.4 is unsubstituted or substituted alkyl, aralkyl, aryl, vinyl, alkoxy, phenoxy or amino, andR.sub.5 is cyano, carbalkoxy, or unsubstituted or substituted carbonamide, andR.sub.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: October 15, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Mockli
  • Patent number: 4545993
    Abstract: Heterocyclic compounds comprising the formula (I): ##STR1## wherein: R.sub.1, R.sub.2, R.sub.4 and R.sub.5 each are hydrogen or a lower alkyl group;R.sub.3 is hydrogen, a halogen, an alkyl group, a haloalkyl group, an alkoxy group, an alkenyl group, an alkenyloxy group, an aryl group, an aryloxy group, an acyl group or a nitro group;and the broken line connotes a single or double bond at the C.sub.3 -C.sub.4 position, provided that when the broken line connotes a single bond, R.sub.3 is other than hydrogen; and pharmaceutically acceptable salts thereof,exhibiting antiinflammatory, antipyretic and analgesic action.
    Type: Grant
    Filed: July 20, 1982
    Date of Patent: October 8, 1985
    Assignee: Nippon Zoki Pharmaceutical Co. Ltd.
    Inventors: Kaoru Okamoto, Masaki Hamada, Teikichi Kurosaki
  • Patent number: 4537920
    Abstract: 4H-1-Benzopyrans are prepared by reacting an aminomethylphenol with an alkali metal hydroxide or an alkaline earth metal hydroxide and a 1,3-diketone. The products are useful as antioxidants.
    Type: Grant
    Filed: August 18, 1983
    Date of Patent: August 27, 1985
    Assignee: Ethyl Corporation
    Inventor: Jerry M. Roper
  • Patent number: 4511685
    Abstract: Chroman derivatives of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each H or C.sub.1 -C.sub.4 -alkyl, R.sup.5 is C.sub.10 -C.sub.30 -alkyl or C.sub.10 -C.sub.30 -alkenyl, X and Y are each O, NH or S, m is 0, 1, 2 or 3 and n and r are each 0 or 1, the preparation of compounds I by various methods known per se, and the use of the compounds as stabilizers for organic materials.
    Type: Grant
    Filed: February 26, 1981
    Date of Patent: April 16, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Axel Nissen, Michael Horner, Dieter Horn, Erik Lueddecke, Gernot Teege
  • Patent number: 4511391
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, alkenyl, alkynyl, hydroxy, alkoxy, substituted alkoxy, alkenyloxy, alkynyloxy, alkanoyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, benzyloxy, substituted benzyloxy, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;Y and Z are independently selected from methylene, oxygen and sulfur provided that at least one of Y and Z is selected from oxygen and sulfur;R.sup.1 is selected from hydrogen, alkyl, alkenyl alkynyl, substituted alkyl, acyl, alkylsulfonyl, benzenesulfonyl, substituted benzenesulfonyl, and an inorganic or organic cation;R.sup.2 is selected from alkyl, alkenyl, alkynyl, substituted alkyl, haloalkenyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl and phenyl;R.sup.4 is selected from hydrogen, halogen, cyano, C.
    Type: Grant
    Filed: May 24, 1983
    Date of Patent: April 16, 1985
    Assignee: ICI Australia Limited
    Inventors: Alexander Serban, Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
  • Patent number: 4503256
    Abstract: Novel compounds of general formula I ##STR1## wherein R is a branched or unbranched alkyl, cycloalkyl, or aralkyl group, which group optionally contains or is substituted by a halogen or oxygen function, the oxygen function optionally being in the form of an alcohol or ether moiety;R.sub.1, R.sub.2, and R.sub.3, which may be the same or different, is hydrogen, an alkyl, acyl, or benzoyl group, which group optionally contains or is substituted by a halogen or oxygen function;R.sub.4 is hydrogen, an alkyl, alkenyl preferably being an allyl or prenyl group, or aralkyl group which group optionally contains or is substituted by an alkyl, aryl, halogen or oxygen function;R.sub.5 is hydrogen, an alkyl, aralkyl, acyl, or aryl group, which group optionally contains or is substituted by an alkyl, aryl, halogen, or oxygen function;except that R.sub.4 and R.sub.5 are not both hydrogen;and except for the compounds when R.sub.
    Type: Grant
    Filed: June 21, 1982
    Date of Patent: March 5, 1985
    Assignee: Noristan Limited
    Inventors: Theunis G. Fourie, Theodor G. Dekker, Friedrich O. Snyckers, Cornelis J. van der Schyf
  • Patent number: 4456565
    Abstract: Acyl cyanides of the general formula ##STR1## in which R represents alkyl or substituted alkyl of from 1 to 8 carbon atoms; cycloalkyl or substituted cycloalkyl with 3 to 12 carbon atoms; aryl or substituted aryl; or an optionally substituted 5-membered or 6-membered heterocyclic radical which can additionally also be fused with a benzene ring, are prepared by reacting the corresponding carboxylic acid anhydride in the liquid phase with anhydrous hydrocyanic acid, at a temperature of between 50.degree. to 250.degree. C.
    Type: Grant
    Filed: July 14, 1983
    Date of Patent: June 26, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Herbert Schwarz
  • Patent number: 4394382
    Abstract: A benzopyran compound represented by the following ##STR1## wherein A represents a direct bond or the bond --CH.sub.2 --O--,R.sub.1 represents a member selected from the group consisting of a C.sub.3 -C.sub.5 alkyl group, a hydroxy-(C.sub.3 -C.sub.5 alkyl) group, a lower alkylamino-lower alkyl group, a nitrato-(C.sub.3 -C.sub.5 alkyl) group and a phenyl-(C.sub.1 -C.sub.5) alkyl group, provided that the phenyl may be substituted by a lower alkoxy group, R.sub.2 represents a member selected from the group consisting of hydrogen, halogen, OH, NO.sub.2, a carbamoyl group, a lower alkyl group, a lower alkoxy group, a lower alkyleneoxy group and acetyl group,R.sub.3 represents hydrogen or NO.sub.2,B represents a direct bond, a C.sub.1 -C.sub.7 alkylene group, a --O-lower alkylene group or a --CONH-lower alkylene group, andn represents 1 or 2;and an acid addition salt thereof and a pharmaceutical composition comprising aforesaid compound.
    Type: Grant
    Filed: June 9, 1981
    Date of Patent: July 19, 1983
    Assignee: Kowa Company, Ltd.
    Inventors: Masami Shiratsuchi, Noboru Shimizu, Hiromichi Shigyo, Yoshinori Kyotani, Hisashi Kunieda, Kiyoshi Kawamura, Seiichi Sato, Toshihiro Akashi, Masahiko Nagakura, Naotoshi Sawada, Yasumi Uchida
  • Patent number: 4341792
    Abstract: Heterobicyclic glyoxylic acids, L- and DL-heterobicyclic glycines and their derivatives of the formulae ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, wherein R is OR.sup.2 or NHR.sup.3 ;R.sup.2 is hydrogen or alkyl having from one to four carbon atoms;R.sup.3 is hydrogen, alkyl having from one to four carbon atoms, alkoxyalkyl having from one to four carbon atoms in each of the alkyl groups or R.sup.4 R.sup.5 C.sub.6 H.sub.3 CH.sub.2 -- where R.sup.4 and R.sup.5 are H, OH, F, Cl, Br, I, or alkyl or alkoxy having from one to four carbon atomsR.sup.1 is hydrogen, alkyl having from one to four carbon atoms or R.sup.4 R.sup.5 C.sub.6 H.sub.3 --; X is oxygen or sulfur; n is 0 or 1 and the broken line represents an optionally present double bond; useful in treatment of diseases and conditions which are characterized by reduced blood flow, reduced oxygen availability or reduced carbohydrate metabolism in the cardiovascular system.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: July 27, 1982
    Assignee: Pfizer Inc.
    Inventors: Ian T. Barnish, Peter E. Cross