Chalcogen Bonded Directly To The Hetero Ring Patents (Class 549/475)
  • Patent number: 5223533
    Abstract: The invention relates to the benzylcyclanone derivatives of formula: ##STR1## where R.sub.1 and R.sub.3 denote H, OH, linear or branched C.sub.1 -C.sub.8 alkyl or linear or branched C.sub.1 -C.sub.8 alkoxy, R.sub.2 and R.sub.4 represent H or OH, at least one of the two being OH, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 represent H, C.sub.1 -C.sub.18 alkyl, aralkyl or aryl, it being possible for R.sub.5 and R.sub.6 and/or R.sub.7 and R.sub.8 to form an optionally substituted, saturated C.sub.5 -C.sub.12 ring, X represents O or --(CR.sub.9 R.sub.10).sub.n with n=1 or 2 and R.sub.9 and R.sub.10 represent H or CH.sub.3 ; if X represents --(CR.sub.9 R.sub.10).sub.n, R.sub.6 and R.sub.8, with the atoms of the ring to which they are attached, form a bicyclic system having 7 or 8 carbon atoms; if X represents --(CR.sub.9 R.sub.10).sub.n with n=1, R.sub.9 and R.sub.10 =CH.sub.3, R.sub.5 =H and R.sub.6 and R.sub.8, with the atoms of the ring to which are attached, form a bicyclic system having 7 carbon atoms, R.sub.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: June 29, 1993
    Assignee: L'Oreal
    Inventors: Serge Forestier, Alain LaGrange, Gerard Lang, Andre Deflandre, Bernadette Luppi
  • Patent number: 5217709
    Abstract: Cosmetic composition containing, by way of a compound screening cut UV of wavelengths 280-380 nm, a 5-benzylidene-3-oxacyclopentanone of formula (I): ##STR1## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 denote C.sub.1 -C.sub.8 alkyl, aralkyl or aryl, or alternatively R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 form, with the carbon to which they are attached, a saturated 5- or 6-membered ring, andR.sub.5, R.sub.6 and R.sub.7 denote H, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.8 alkenyloxy, C.sub.2 -C.sub.12 acyloxy, benzyloxy or --COOR.sub.10 where R.sub.10 is a C.sub.1 --C.sub.8 alkyl, hydrogen, an alkali metal or alkaline earth metal or a radical derived from an amine, it also being possible for one of the substituents R.sub.5, R.sub.6 and R.sub.7 to denote a radical ##STR2## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the above meanings. This composition can be a protective composition for the human epidermis or the hair or an antisun composition.
    Type: Grant
    Filed: October 24, 1989
    Date of Patent: June 8, 1993
    Assignee: L'Oreal
    Inventors: Alain Lagrange, Serge Forestier, Gerard Lang, Bernadette Luppi
  • Patent number: 5217991
    Abstract: Non-peptidyl compounds characterized generally as cycloalkyl/cycloalkylalkyl-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 cycloalkyl and cycloalkylalkyl groups, wherein said cycloalkyl group contains three to about eight carbon atoms and the acyclic alkyl portion of said cycloalkylalkyl group contains one to about eight carbon atoms; 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: May 28, 1992
    Date of Patent: June 8, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
  • Patent number: 5216013
    Abstract: Non-peptidyl compounds characterized generally as heterocyclic acyl aminodiol .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are compounds of the formula ##STR1## wherein R.sub.1 is selected from aryl and aralkyl groups represented by ##STR2## and wherein R.sub.1 may be further selected from heteroaryl and heteroaralkyl represented by ##STR3## wherein each of T and A is independently selected from N and CH; wherein n is a number selected from zero through five, inclusive; wherein X is selected from oxygen atom, methylamino and NH; wherein each of Y and Z is independently selected from chloro, fluoro, methoxy and dimethylamino; wherein Q is oxygen atom; and wherein each of T and A is independently selected from N and CH; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is selected from methyl and ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; wherein R.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: June 1, 1993
    Assignee: G. D. Searle & Co.
    Inventor: Gunnar J. Hanson
  • Patent number: 5208333
    Abstract: (2R)-1-(Aryloxy)-3-(butyryloxy)-2-propanols of the general formula (I), ##STR1## where Ar is a monocyclic or polycyclic aromatic or heteroaromatic radical, and a process for their preparation by the reaction of (2R)-glycidyl butyrate with an aromatic hydroxy compound Ar--OH in the presence of a quaternary ammonium halide.
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: May 4, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Axel Paul, Wolfgang Ladner, Hardo Siegel
  • Patent number: 5164520
    Abstract: Intermediate for the preparation of antiviral compounds having the formula ##STR1## wherein R.sub.1 is a purine or pyrimidine base or an analog thereof.
    Type: Grant
    Filed: August 7, 1991
    Date of Patent: November 17, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Robert Zahler, Joseph A. Tino
  • Patent number: 5153337
    Abstract: Novel processes and intermediates for the preparation of tetrahydro-5-hydroxy-3-methylene-2-furan-methanol and of tetrahydro-5-[lower alkoxy (C.sub.1 -C.sub.3)]-3-methylene-2-furanmethanol useful as intermediates in the synthesis of various modified nucleosides having antiviral and other biological activity.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: October 6, 1992
    Assignee: American Cyanamid Company
    Inventor: Yuri E. Raifeld
  • Patent number: 5145703
    Abstract: The invention relates to new thio-alkanones of the formula ##STR1## in which X represents an oxygen or sulphur atom,R.sub.1 represents hydrogen or a C.sub.1 -C.sub.2 -alkyl group and the broken lines represent a single bond or no bond,to a process for their preparation and their use as flavorings.
    Type: Grant
    Filed: May 16, 1991
    Date of Patent: September 8, 1992
    Assignee: Haarmann & Reimer
    Inventors: Roland Emberger, Matthias Gunter, Rudolf Hopp, Manfred Kopsel, Walter Kuhn, Peter Werkhoff
  • Patent number: 5128348
    Abstract: Certain hexane and heptane amines including geometric and stereoisomers, agricultural compositions containing them and their use as fungicides.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: July 7, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Gregory S. Basarab
  • Patent number: 5128370
    Abstract: New furans and lactones from streptomycetes, a process for the preparation thereof, and the use thereof.It is possible with the aid of various streptomycetes species to prepared new compounds having a furan or lactone structure. These compounds have a pharmacological, especially antibiotic, action.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: July 7, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Susanne Grabley, Joachim Wink, Klaus Kuhlein, Gerhard Seibert, Klaus Hutter, Hermann Uhr, Axel Zeeck
  • Patent number: 5126347
    Abstract: Isomeric derivatives of 2',3'-dideoxyadenosine and 2',3'-dideoxyguanosine wherein the adenine or guanine base is attached to the 1' position of the iso-dideoxysugar residue by the 9-N position, the novel intermediates used in the synthesis of these compounds, and a method for treating a subject infected with a retrovirus by administering the compounds of the invention.
    Type: Grant
    Filed: February 13, 1989
    Date of Patent: June 30, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Donna M. Huryn, Steve Yik-Kai Tam, Manfred Weigele
  • Patent number: 5116869
    Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: May 26, 1992
    Assignee: Teijin Limited
    Inventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
  • Patent number: 5099033
    Abstract: The present invention is directed to a process of making tetrahydrofuran of the formula (D) ##STR1## resulting in 2,5-diaryltetrahydrofuran PAF antagonists of pharmaceutically acceptable purity.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: March 24, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Ichiro Shinkai, Andrew S. Thompson, Thomas R. Verhoeven
  • Patent number: 5072008
    Abstract: The invention concerns a novel process for the stereospecific manufacture of novel hydroxymethyl lactols of the formula I by a one step reduction of a corresponding lactone carboxylic ester of the formula II (many of which esters are novel) using a reducing agent such as diisobutylaluminium hydride at about ambient temperature. The lactols of formula I are intermediates for the production of pharmacologically active 1,3-dioxane alkenoic acids useful in the treatment of certain cardiovascular and pulmonary medical conditions. Certain of the esters of formula II are novel and are also included in the invention.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: December 10, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventor: Gregory D. Harris
  • Patent number: 5055471
    Abstract: This invention relates to derivatives of propanoic acid of the formula ##STR1## Useful as fungicides, insecticides and miticides, to processes for preparing them, to compositions containing them, and to methods of using them to combat fungi, especially fungal infections of plants, and to kill or control insects and mites.
    Type: Grant
    Filed: November 15, 1989
    Date of Patent: October 8, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Paul J. de Fraine, Anne Martin
  • Patent number: 5055599
    Abstract: Tetrahydrofuran and gamma-butyrolactone are prepared from at least one of maleic anhydride or succinic anhydride by catalytically hydrogenating vaporous maleic anhydride or vaporous succinic anhydride in the presence of hydrogen in contact with a catalyst comprising an essentially inert, at least partially porous support having an outer surface, and a catalytically active oxide material coating onto the outer surface of the support which strongly adheres to the support, wherein the catalytically active oxide material comprises the mixed oxides of copper, zinc and aluminum.
    Type: Grant
    Filed: June 23, 1989
    Date of Patent: October 8, 1991
    Assignee: The Standard Oil Company
    Inventor: John R. Budge
  • Patent number: 5053430
    Abstract: Novel compounds having the general formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined herein. These compounds are useful in the treatment of schizophrenia.
    Type: Grant
    Filed: September 22, 1989
    Date of Patent: October 1, 1991
    Assignee: Boehringer Ingelheim KG
    Inventors: Matthias Grauert, Herbert Merz, Joachim Mierau, Gunter Schingnitz, Claus Schneider
  • Patent number: 5008408
    Abstract: Mixtures which contain 1,4-butanediol and tetrahydrofuran are prepared by heating 4-hydroxybutyraldehyde of the formula ##STR1## at 20.degree.-300.degree. C. in the presence or absence of 1,4-butanediol and subjecting the resulting acetals of the formulae ##STR2## to a catalytic hydrogenation at 50.degree.-300.degree. C. and 1-350 bar.
    Type: Grant
    Filed: March 7, 1990
    Date of Patent: April 16, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Juergen Frank, Franz Merger, Hans-Juergen Weyer
  • Patent number: 5001253
    Abstract: A fluorescent brightener is proposed which consists of 51-99% of an unsymmetrically substituted compound of the formula ##STR1## in which R and R.sub.1 are identical or different and, if R and R.sub.1 are identical, R.sub.1 must occupy a position in the phenyl ring to which it is bonded which differs from the position occupied by R in its phenyl ring, and in which R and R.sub.1 independently of one another are CN or a corboxylic acid ester group, and 49-1% of a symmetrically substituted compound of the formula ##STR2## in which R is as defined above and the two R's are bonded to identical positions in their phenyl rings, as are also agents which contain these fluorescent brighteners and the use of these fluorescent brighteners for the fluorescent brightening of, in particular, textile materials, preferably made of polyester.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: March 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Leonardo Guglielmetti
  • Patent number: 4968836
    Abstract: The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises (a) reacting a tetrahydrofuran of formula ##STR2## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: November 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ruedi Kanel, John G. Dingwall
  • Patent number: 4943584
    Abstract: Novel (p-phenoxyphenoxy)-methyl-five-membered heeroaromatic radicals of the formula ##STR1## where the substituents have the following meanings: R.sup.1, R.sup.2, R.sup.3 hydrogen, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.10 -cycloalkyl, nitro or cyano,R.sup.4 hydrogen or C.sub.1 -C.sub.4 -alkyl, and a five-membered heteroaromatic ring, and their use for combating pests.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: July 24, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Theobald, Christoph Kuenast, Peter Hofmeister, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Wolfgang Krieg, Joachim Leyendecker, Uwe Kardorff
  • Patent number: 4929738
    Abstract: Microbicidal substituted pyrazolin-5-ones of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, alkylaminocarbonylalkyl or dialkylaminocarbonylalkyl, or represent in each case optionally substituted oxiranylalkyl, aralkyl, heterocyclyl or aryl andHet represents an optionally substituted heterocyclic radial.Intermediates therefor of the formula ##STR2## in which R is alkyl, are also new.
    Type: Grant
    Filed: May 10, 1989
    Date of Patent: May 29, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Jelich, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
  • Patent number: 4920231
    Abstract: A process for the preparation of trifluoromethylvinyl compounds in all their possible streoisomeric forms and mixtures thereof comprising reacting a salt of trifluoroacetic acid with a halovinyl compound in the presence of a cuprous salt to obtain the same stereo-specific compound and all possible stereo-isomeric forms and mixtures thereof of 1R, trans compounds of the formula ##STR1## wherein R is an alcohol residue used in pyrethrinoid series, or an alcohol residue capable of blocking the acid function, and Z is aryl or haloaryl and the double bond has Z geometry having pesticide activity.
    Type: Grant
    Filed: March 30, 1989
    Date of Patent: April 24, 1990
    Assignee: Roussel Uclaf
    Inventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 4897397
    Abstract: Certain aryl-alkynoic, alkenoic and alkanoic acids and derivatives and their use in treating inflammation, allergy and hyperproliferative skin disease are disclosed.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: January 30, 1990
    Assignee: Schering Corporation
    Inventors: Neng Y. Shih, David J. Blythin
  • Patent number: 4871761
    Abstract: Novel pesticides of the formula ##STR1## in which R.sup.1 represents in each case optionally substituted cycloalkyl, cycloalkenyl, tetrahydronaphthyl, decahydronaphthyl, phenyl, naphthyl or thienyl,R.sup.2 represents alkyl,R.sup.3 represents hydrogen alkyl, alkenyl, alkinyl, hydroxyalkyl, alkoxyalkyl, dialkoxyalkyl, hydroxyalkoxyalkyl, cyano or formyl, or in each case optionally substituted cycloaklyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, aralkyl, aryl, furanylmethyl or tetrahydrofuranylmethyl,R.sup.4 represents hydrogen or alkyl, andHet represents an optionally substituted heterocyclic ring of the formula ##STR2## and acid-addition salts thereof.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: October 3, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Detlef Wollweber, Stefan Dutzmann
  • Patent number: 4871756
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4, E.sub.4 and the slow reacting substance of anaphylaxis.As such, these compounds will be useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.
    Type: Grant
    Filed: February 17, 1987
    Date of Patent: October 3, 1989
    Assignee: Merck Frosst Canada, Inc.
    Inventors: John Gillard, Joshua Rokach, Patrice C. Belanger
  • Patent number: 4866091
    Abstract: This invention relates to new alkane-sulfonanilide derivatives of the formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.8 are each hydrogen, cyano, halogen, lower alkyl, halo (lower) alkyl, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl or lower alkoxy,R.sup.3 is lower alkyl,R.sup.4 is acyl, cyano, carboxy, hydroxy(lower)-alkyl, mercapto, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, 5-membered unsaturated heterocyclic group which may have amino, lower alkanoylamino, lower alkylthio or lower alkylsulfonyl, phenylthio which may have nitro or amino, lower alkanoyl(lower)alkenyl or a group of the formula: ##STR2## wherein R.sup.6 is hydrogen, amino or lower alkyl andR.sup.7 is hydroxy, lower alkoxy, carboxy(lower)alkoxy, lower alkoxycarbonyl(lower)alkoxy, ureido or thioureido, andR.sup.5 is hydrogen, halogen, lower alkyl or lower alkanoyl, and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: June 2, 1988
    Date of Patent: September 12, 1989
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masaaki Matsuo, Kiyoshi Tsuji, Nobukiyo Konishi
  • Patent number: 4855318
    Abstract: Iodopropargyl ethers of the formula ##STR1## wherein A represents oxygen or a methylene group,R.sup.1 denotes hydrogen or lower alkyl,R.sup.2 and R.sup.3 are identical or different and represent hydrogen, lower alkyl, alkenyl or unsubstituted or halogen-substituted phenyl, or R.sup.2 and R.sup.3 together form a carbocyclic ring with 4 to 7 C atoms,l and m represent 0, 1 or 2,k denotes 0 or 1 andn denotes an integer from 0 to 4, with the proviso that if l is 0, n represents 1, 2, 3 or 4,can be prepared by reaction of the corresponding propargyl ethers with iodinating agents. The iodopropargyl ethers are active compounds in microbicidal agents.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: August 8, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerold Schade, Wilfried Paulus, Hans-Georg Schmitt
  • Patent number: 4829078
    Abstract: This invention relates to compounds presented by the general formula: ##STR1## [wherein R.sup.1 and R.sup.2 are: (i) R.sup.1, R.sup.2 and carbon atoms to which R.sup.1 and R.sup.2 are linked, together represent the group of the general formula: ##STR2## (wherein R.sup.5 and R.sup.6 represent hydrogen, alkyl, cycloalkyl, cycloalkyl-alkyl or phenyl, independently, with the proviso that R.sup.5 and R.sup.6 is not hydrogen atoms at the same time), or(ii) R.sup.1 represents hydrogen and R.sup.2 represents the group of the formula: --COR.sup.7 (wherein R.sup.7 represents the group of the formula: ##STR3## (wherein Y represents a single-bond, alkylene, alkenylene, W represents oxygen or sulfur, m represents 1 to 3, R.sup.8 represents hydrogen, halogen, nitro, hydroxy, alkyl or alkoxy, with the proviso that when m represents two or more, plural R.sup.8 s may be different each, and R.sup.9 represents hydrogen, alkyl or phenyl group, with the proviso that two of R.sup.9 may be different each)), R.sup.
    Type: Grant
    Filed: February 22, 1988
    Date of Patent: May 9, 1989
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Katsuhiro Imaki, Tadao Okegawa, Yoshinobu Arai
  • Patent number: 4824974
    Abstract: This application relates to a stereospecific process for preparing specific enantiomers of 4-amino-4,5-dihydro-2-furancarboxylic acid and C.sub.1-6 lower alkyl esters thereof. These compounds are .gamma.-aminobutyric acid transaminase inhibitors useful in the treatment of epilepsy.
    Type: Grant
    Filed: October 15, 1987
    Date of Patent: April 25, 1989
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Joseph P. Burkhart, Gene W. Holbert
  • Patent number: 4822909
    Abstract: 7-Fluoroprostaglandins represented by the following formula (I): ##STR1## In the formula (I), R.sup.1 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sup.2, R.sup.3 and R.sup.4 are hydrogen atoms or the same or different protective groups, respectively, and R.sup.5 is a straight chained, branched or cyclic alkyl group having from 3 to 7 carbon atoms.
    Type: Grant
    Filed: June 9, 1987
    Date of Patent: April 18, 1989
    Assignee: Asashi Glass Company Ltd.
    Inventors: Yasuda Arata, Kato Masao, Yamabe Masaaki, Uchida Keiichi
  • Patent number: 4804767
    Abstract: Dyes of formula (1) as claimed in claim 1 can conveniently be prepared by reacting an anthraquinone compound of formula (2) with a haloformate of formula (3) in an inert organic solvent and in the presence of 1 to 2 moles of a heterocyclic tertiary nitrogen base per mole of compound of formula (2).
    Type: Grant
    Filed: July 29, 1987
    Date of Patent: February 14, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Kaser
  • Patent number: 4786646
    Abstract: The invention relates to compounds of the formula ##STR1## Y is O or S, *A is paraphenylene or *--(CH.sub.2).sub.n --(X).sub.m --(CH.sub.2).sub.r --, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R.sub.1 and R.sub.2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het or aryl, *E is ##STR2## or --(CH.sub.2).sub.k -- wherein k is an integer from 0 to 4, R.sub.3, R.sub.4 and R.sub.8 are independently hydrogen or lower alkyl, R.sub.5 and R.sub.6, independently are hydrogen or lower alkyl, R.sub.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: November 22, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
  • Patent number: 4785109
    Abstract: These is described a process for producing sulfonylureas of the formula ##STR1## wherein G is an unsubstituted or substituted furanyl, thienyl, pyrrolyl, pyridinyl or phenyl radical,X is alkyl, haloalkyl, alkoxy, alkylthio, halogen, haloalkoxy, alkylamino or dialkylamino,Y is alkyl, alkoxy or haloalkoxy,Z is a nitrogen atom or the methyne group --CH.dbd..This novel process comprises reacting a sulfonamide of the formulaG--SO.sub.2 --NH.sub.2,in the presence of a base, with a chloroformic acid ester of the formulaCl--CO--Q--T,or a sulfonyl chloride of the formulaG--SO.sub.2 Cl,in the presence of a base, with a urethane of the formulaH.sub.2 N--CO--Q--T;and converting the formed carbamate of the formulaG--SO.sub.2 --NH--CO--Q--Tby reaction with an amine of the formula ##STR2## into the sulfonylurea of the above formula. There are also described novel sulfonylcarbamates of the above formula as intermediates.
    Type: Grant
    Filed: January 30, 1987
    Date of Patent: November 15, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Meyer, Werner Fory, Werner Topfl
  • Patent number: 4778818
    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: April 17, 1987
    Date of Patent: October 18, 1988
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
  • Patent number: 4762848
    Abstract: Heterocyclic sulfides of the general formula heterocycle-S-R, a process for their preparation and, in particular, their use for immunostimulation, immunorestoration and cytostatic treatment, and pharmaceutical agents, which contain a sulfide of this type, for these indications.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: August 9, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl-Heinz Scheunemann, Walter Durckheimer, Jurgen Blumbach, Michael Limbert, Hans-Ulrich Schorlemmer, Gerhard Dickneite, Hans-Harald Sedlacek
  • Patent number: 4743617
    Abstract: This invention relates to novel heterocyclyl-2-propyn-1-amines which are useful as dopamine beta hydroxylase inhibitors in the treatment of hypertension.
    Type: Grant
    Filed: August 31, 1987
    Date of Patent: May 10, 1988
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Thomas M. Bargar, Lawrence C. Creemer, James R. McCarthy
  • Patent number: 4739068
    Abstract: N-Phenylsulfonyl-N'-pyrimidinylureas and --N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence.In the formulaR.sub.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl,R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms,R.sub.3 is halogen, hydrogen, --NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms,R.sub.4 is hydrogen or methyl,R.sub.5 is hydrogen, C.sub.1 -C.sub.2 alkyl or methoxy,A is C.sub.1 -C.sub.4 alkylene or C.sub.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: April 19, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Karl Gass, Werner Fory, Willy Meyer, Werner Topfl
  • Patent number: 4725302
    Abstract: Phenylhydrazines of the formula I ##STR1## wherein R.sub.1 is --A--R--Z,A is oxygen, sulfur, ##STR2## R is C.sub.1 -C.sub.6 -alkylene, C.sub.1 -C.sub.6 -haloalkyl-C.sub.1 -C.sub.6 -alkylene, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkylene or C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkylene,Z is halogen, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylsulfinyl or C.sub.1 -C.sub.6 -alkylsulfonyl, orR and Z together are ##STR3## R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio or (C.sub.1 -C.sub.6 -alkyl).sub.2 amino,n is a number from 1-4, and R.sub.2 can be different when n is one of the numbers 2-4,R.sub.3 is halogen,R.sub.4 is hydrogen,R.sub.5 is --COOR.sub.6, orR.sub.3, R.sub.4 and R.sub.5 together form a bridge member of the formula ##STR4## and R.sub.6 is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl.
    Type: Grant
    Filed: November 20, 1985
    Date of Patent: February 16, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 4703127
    Abstract: Compounds of the general formula I are disclosed as useful intermediates in the preparation of prostanoids: ##STR1## wherein A represents O or H, OR.sup.z ;R.sup.z represents hydrogen or a protecting group;R.sup.x represents hydrogen or a protecting group; andR.sup.y represents halogen, a substituted thio group, di-substituted amino group, or a group of the formula R.sup.2, and R.sup.2 represents a straight- or branched-chain alkyl alkenyl or alkynyl group which may optionally be substituted by one or more carboxyl, carboxylic acid ester, or free or protected hydroxyl, thiol, aldehyde or keto groups;with the provisos that R.sup.x is not hydrogen when A is O and R.sup.y is R.sup.2 ; and that when A is H, OR.sup.z R.sup.y and R.sup.2 and R.sup.x and R.sup.z are not both hydrogen.Processes for the preparation of these compounds and of 2-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives are also disclosed.
    Type: Grant
    Filed: September 2, 1983
    Date of Patent: October 27, 1987
    Assignee: The Australian National University
    Inventors: Rodney W. Rickards, Melvyn Gill, Robert M. Christie
  • Patent number: 4699989
    Abstract: 7-Fluoroprostaglandins represented by the following formula (I): ##STR1## In the formula (I), R.sup.1 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sup.2, R.sup.3 and R.sup.4 are hydrogen atoms or the same or different protective groups, respectively, and R.sup.5 is a straight chained, branched or cyclic alkyl group having from 3 to 7 carbon atoms.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: October 13, 1987
    Assignee: Asahi Glass Company Ltd.
    Inventors: Yasuda Arata, Kato Masao, Yamabe Masaaki, Uchida Keiichi
  • Patent number: 4659844
    Abstract: The invention relates to new cyclic ethers which are substituted in the .alpha.-position by an isocyanide-dichloride group, of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n have the meaning indicated in the description, and to a process for their preparation.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: April 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Tillmann Hassel, Hanns P. Muller, Horst Boshagen
  • Patent number: 4649156
    Abstract: The present invention provides a novel 6-nitroprostaglandin derivatives of the formula (I) ##STR1## wherein A, n, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in claim 1.The 6-nitroprostaglandin derivatives is useful as medicines because of its excellent pharmacological activities including platelet aggregation inhibiting activity, blood pressure lowering activity and anti-ulcerous activity, and useful as intermediate for other pharmaceutically active compounds such as 6-oxoprostaglandin derivatives, prostaglandin E.sub.1 derivatives, etc.
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: March 10, 1987
    Assignee: Teijin Limited
    Inventors: Toshio Tanaka, Atsuo Hazato, Seizi Kurozumi
  • Patent number: 4643849
    Abstract: This invention relates to amine derivatives and salts thereof. These compounds have an anti-ulcer activity which is effective to human beings and animals. This disclosure relates to such compounds, a process for the preparation thereof and an anti-ulcer agent containing the same.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: February 17, 1987
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Shiro Hirai, Hiroshi Hirano, Hirotoshi Arai, Yasuo Kiba, Hisanari Shibata, Yoshikazu Kusayanagi, Minako Yotsuji, Kazuhiko Hashiba, Kikuko Tanada
  • Patent number: 4638060
    Abstract: Antibacterial activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: April 29, 1985
    Date of Patent: January 20, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joseph E. Sundeen, William H. Koster, Robert Zahler
  • Patent number: 4636505
    Abstract: Acylanilides of the formula ##STR1## wherein R.sup.1 and R.sup.2, the same or different, each is cyano, carbamoyl, nitro, halogeno, perfluoroalkyl or other defined substituents;R.sup.3 is hydrogen or halogen;R.sup.4 is hydrogen or alkyl, or is joined to R.sup.5 ;R.sup.5 is hydrogen, hydroxy, alkoxy or acyloxy or is joined to R.sup.4 ;R.sup.6 is alkyl or halogenoalkyl, or has the formula --A.sup.3 --R.sup.8 or --A.sup.4 --X.sup.2 --A.sup.5 --R.sup.9 ;A.sup.1 and A.sup.4, the same or different, each is alkylene;A.sup.2, A.sup.3 and A.sup.5, the same or different, each is a direct link or alkylene;X.sup.1 and X.sup.2, the same or different, each is oxygen, sulphur, sulphinyl, sulphonyl, imino or alkylimino;R.sup.7 and R.sup.9, the same or different, each is alkyl, alkenyl, hydroxyalkyl, cycloalkyl, phenyl optionally substituted, naphthyl or heterocyclic optionally substituted;and R.sup.8 is phenyl, naphthyl or heterocyclic as defined above for R.sup.7 or R.sup.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: January 13, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventor: Howard Tucker
  • Patent number: 4634783
    Abstract: Amidine compounds of the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful anti-trypsin, anti-plasmin, anti-kallikrein and anti-thrombin agents. They are also useful as a powerful anti-complement agent.
    Type: Grant
    Filed: January 23, 1984
    Date of Patent: January 6, 1987
    Assignee: Torii & Co. Ltd.
    Inventors: Setsuro Fujii, Toyoo Nakayama, Shigeki Nunomura, Ryoji Matsui, Shin-ichi Watanabe, Kimio Sudo, Toshiyuki Okutome, Masateru Kurumi, Yojiro Sakurai, Takuo Aoyama
  • Patent number: 4618359
    Abstract: New herbicidal chemical compounds of the formula: ##STR1## wherein X is trifluoromethyl; Y is selected from the group consisting of hydrogen, halogen, nitro and cyano and R is selected from the group consisting of nitro, alkylthio, halogen and cyano; herbicidal compositions thereof and methods of controlling weeds therewith. The compound, 3-tetrahydrofuryl 2-nitro-5-(2-chloro-4-trifluoromethylphenoxy) benzoate, is particularly useful for the control of the weed, velvetleaf, and safe to corn and soybean. Velvetleaf is found in corn and soybean crops and its presence will lower the yield of these crops.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: October 21, 1986
    Assignee: Sandoz Ltd.
    Inventor: Frank Wu
  • Patent number: 4608435
    Abstract: New benzo-1,4-quinones and salts thereof with organic or inorganic acid and bases have the formula I ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## wherein Q is selected from the residues --CO.sub.2 R.sub.4, --CON(R.sub.4)(R.sub.5), --OR.sub.5, --OCOR.sub.7, --N(R.sub.8)(R.sub.9), --PO(OR.sub.10)([O].sub.x R.sub.11), --SO.sub.2 R.sub.12, --CN, Halogen, --NO.sub.2 or --COR.sub.13, n is an integer from 1 to 20, k is 1 or 2 and x is 0 or 1, and R.sub.1 to R.sub.5 and R.sub.7 to R.sub.13 are as defined in the specification.The compounds of formula I are useful in photographic materials such as bleaching inhibitors in films of photographic silver dye bleach materials.
    Type: Grant
    Filed: April 28, 1983
    Date of Patent: August 26, 1986
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4608385
    Abstract: Use of an N-phenylcarbamate of the formula: ##STR1## as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole thiophanate fungicides and/or cyclic imide fungicides.
    Type: Grant
    Filed: October 22, 1982
    Date of Patent: August 26, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Noguchi, Toshiro Kato, Junya Takahashi, Yukio Ishiguri, Shigeo Yamamoto, Katsuzo Kamoshita