Chalcogen Bonded Directly To Ring Carbon Of The Six-membered Hetero Ring Patents (Class 546/103)
  • Patent number: 5086179
    Abstract: This invention is directed to certain dibenzofurancarboxamides and dibenzofurancarboxamide acids and their use as 5HT.sub.3 antagonists having unique CNS, anti-emetic and gastric prokinetic activity void of any significant D.sub.2 receptor binding properties. Further, this invention relates to a process for the synthesis of stereoisomeric compounds having such CNS, anti-emetic and gastric prokinetic activity.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: February 4, 1992
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Matthew R. Powers, Raymond D. Youssefyeh, William L. Studt, Frederick A. Golec
  • Patent number: 5032592
    Abstract: A compound of the formula ##STR1## wherein X has the formula ##STR2## wherein ring a is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano, trifluoromethyl, alkylthio, alkylsulphinyl, and alkylsulphonyl or each is hydrogen, alkyl, alkoxy or dialkylamino provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R.sup.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: July 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, John Oldfield, Howard Tucker
  • Patent number: 5030631
    Abstract: Novel tricyclic arylsulfonamides useful for treating hypertension and bronchoconstiction, as well as to their pharmaceutical compositions and methods for using the same.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: July 9, 1991
    Assignee: Schering Corporation
    Inventor: Barr E. Bauer
  • Patent number: 4994452
    Abstract: Novel hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepines and related compounds, intermediates for the preparation thereof, and a method for relieving memory dysfunction, utilizing the compounds are disclosed.
    Type: Grant
    Filed: November 28, 1989
    Date of Patent: February 19, 1991
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Gregory M. Shutske, Kevin J. Kapples, John D. Tomer, IV
  • Patent number: 4985430
    Abstract: There are disclosed a 9-acylamino-tetrahydroacridine derivative represented by the following formula (I): ##STR1## wherein R ##STR2## are as defined in the specification, its optical antipode or pharmaceutically acceptable acid addition salt thereof and a memory enhancing agent containing the same as an active ingredient.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: January 15, 1991
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Shuji Morita, Ken-Ichi Saito, Kunihiro Ninomiya, Akihiro Tobe, Issei Nitta, Mamoru Sugano
  • Patent number: 4962198
    Abstract: The invention relates to a generally applicable process for the hydroxylation of electrophilic aromatic compounds, according to which the electrophilic aromatic compounds are reacted with organic hydroperoxides in the presence of bases.
    Type: Grant
    Filed: July 7, 1989
    Date of Patent: October 9, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Mieczyslaw Makosza, Krzysztof Sienkiewicz
  • Patent number: 4960890
    Abstract: Methine dyes (I) which conform in one of their tautomeric forms to the general formula ##STR1## where Y.sup.1 is in both or either case an electron-attracting group and the other Y.sup.1 is hydrogen,Y.sup.2 is in each case, independently of the others, hydrogen, --CN, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl or together with a further Y.sup.2 a five- or six-membered ring which may have a fused-on benzene ring,R is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.7 -C.sub.10 -aralkyl or .beta.
    Type: Grant
    Filed: October 5, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Ewald Daltrozzo, Werner Sulger
  • Patent number: 4950613
    Abstract: A method of preparing a labelled specific binding partner, such as a biological probe in the form of an antibody or oligonucleotide probe, using a protected label (the corresponding unprotected label being susceptible to inactivation, such as by hydrolysis to yield a non-chemiluminescent form of the label). The specific binding partner is linked to the label, and an adduct of the label is prepared using a protective adduct former which produces a protected label which is less susceptible to inactivation. Particularly preferred labels are the acridiniums and acridans, most preferably the former having the general structure: ##STR1## wherein the phenyl rings are optionally additionally substituted, R.sub.1 is preferably an alkyl, and R.sub.5 is an optionally substituted hydrocarbon, most preferably a phenyl moiety which is either linked to the specific binding partner, or capable of being linked thereto.
    Type: Grant
    Filed: February 26, 1988
    Date of Patent: August 21, 1990
    Assignee: Gen-Probe Incorporated
    Inventors: Lyle J. Arnold, Jr., Alexander A. Waldrop, III, Philip W. Hammond
  • Patent number: 4937345
    Abstract: A process for the preparation of 2-(arylamino)-3-carboxy-9(10H)-acridones of the formula A ##STR1## in which R and R' represent hydrogen, fluorine, chlorine or bromine atoms, alkyl(C.sub.1 -C.sub.4)-, oxalkyl(C.sub.1 -C.sub.4)- or carbonamide groups and x and y denote integers from 1 to 4, by cyclizing 2,5-diarylaminoterephthalic acids of the formula D ##STR2## in which R, R', x and y have the meanings mentioned previously, in a 5- to 15-fold amount by weight of polyphosphoric acid (P.sub.4 O.sub.10 content 80 to about 85%) or of an acidic polyphosphate (P.sub.4 O.sub.10 contents 75 to about 85%) as a water-abstracting agent at about 60.degree. C. to about 100.degree. C.
    Type: Grant
    Filed: October 6, 1988
    Date of Patent: June 26, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Dietz, Heinrich Hamal, Frank Prokschy
  • Patent number: 4881980
    Abstract: Pigments of the quinacridonequinone series consisting of 98-20 mol percent of a quinacridonequinone of the general formula (1) ##STR1## in which R denotes a hydrogen or chlorine atom or a methyl or carbonamide group and m and n are 1 or 2, and 1-65 mol percent of a quinacridone of the general formula (2) ##STR2## in which R, m and n have the abovementioned meaning, and 1-15 mol percent of one or two acridone derivatives of the general formulae (3) and/or (4) ##STR3## in which X denotes O or NH and R can be identical or different and, like m and n, has the abovementioned meaning, the added compounds of the general formulae (2), (3) and/or (4) being predominantly incorporated into the crystal lattice if the quinacridonequinone of the general formula (1), processes for their preparation and their use for coloring synthetic and naturally occurring materials.
    Type: Grant
    Filed: July 9, 1987
    Date of Patent: November 21, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Dietz, Frank Prokschy
  • Patent number: 4834769
    Abstract: Dye compositions containing (a) at least one blue sulpho group-containing triphendioxazine dye and (b) at least one blue sulpho group-containing anthraquinone dye and preferably (c) lignine sulphonic acid or a salt of it and optionally (d) a non-ionic blending agent are outstandingly suitable for the level and fast dyeing of leather substrates.
    Type: Grant
    Filed: December 8, 1987
    Date of Patent: May 30, 1989
    Assignee: Sandoz Ltd.
    Inventors: Michel Dien, Herbert Holliger
  • Patent number: 4810636
    Abstract: Chromogenic acridinone enzyme substrate compounds comprising 7-hydroxy-9H-acridin-2-one chromogens derivatized at the 7-hydroxy-position with an enzymatically-cleavable group and disubstituted at the 9-position with alkyl or aryl groups, which can be the same or different, preferably lower alkyl or phenyl, respectively, or together form a cyclohexa-2,5-diene-4-one residue or a 4-hydroxycycloxhexyl residue, and 7-hydroxy-1,3-dihalo-9,9-dimethyl-acridin-2-one intermediates useful for the preparation of the novel chromogenic acridinone enzyme substrate compounds and methods therefor.
    Type: Grant
    Filed: November 20, 1987
    Date of Patent: March 7, 1989
    Assignee: Miles Inc.
    Inventor: Paul F. Corey
  • Patent number: 4810708
    Abstract: Novel polycyclic quinoline, naphthyridine and pyrazinopyridine derivatives are disclosed which are useful for treating allergic reactions, inflammation, peptic ulcers, hypertension, and hyperproliferative skin diseases and for suppressing the immune response in mammals. Methods for preparing said compounds are also disclosed.
    Type: Grant
    Filed: February 17, 1987
    Date of Patent: March 7, 1989
    Assignee: Schering Corporation
    Inventors: Ashit K. Ganguly, Richard J. Friary, John H. Schwerdt, Marvin I. Siegel, Sidney R. Smith, Vera A. Seidl, Edmund J. Sybertz
  • Patent number: 4803204
    Abstract: The present invention relates to novel, 1-substituted 3-aryl-7-chloro-3,4-dihydro-(2H)-acridone N-oxides, a process for their preparation, pharmaceutical compositions containing these compounds, and their use as chemotherapeutic agents, in particular as antimalarials and coccidiostatics.
    Type: Grant
    Filed: July 20, 1987
    Date of Patent: February 7, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rajkumar Dhar, Bindumadhavan Venugopalan, Dipak K. Chatterjee, Richard H. Rupp, Noel J. de Souza
  • Patent number: 4751309
    Abstract: Methine dyes (I) which conform in one of their tautomeric forms to the general formula ##STR1## where Y.sup.1 is in both or either case an electron-attracting group and the other Y.sup.1 is hydrogen,Y.sup.2 is in each case, independently of the others, hydrogen, --CN, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl or together with a further Y.sup.2 a five- or six-membered ring which may have a fused-on benzene ring,R is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.7 -C.sub.10 -aralkyl or .beta.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: June 14, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Ewald Daltrozzo, Werner Sulger
  • Patent number: 4691059
    Abstract: This invention describes UV-stabilized step growth polymers such as polyesters, polyurethanes, polycarbonates, and combinations thereof. The UV-stabilizing moieties present in these polymers comprise chemically bound, pendant ortho-hydroxydiphenyl ketone based moieties. The polymers are especially useful as protective films and fibers which are highly resistant to ultraviolet (UV) and sunlight degradation.
    Type: Grant
    Filed: August 30, 1985
    Date of Patent: September 1, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Sumita B. Mitra, Smarajit Mitra
  • Patent number: 4626540
    Abstract: Substituted 1-amino-4-nitroacridinones, their method of manufacture, pharmaceutical compositions and their use as antibacterial and antitumor agents are herein described.
    Type: Grant
    Filed: October 10, 1984
    Date of Patent: December 2, 1986
    Assignee: Warner-Lambert Company
    Inventor: David B. Capps
  • Patent number: 4593027
    Abstract: 3-Aryl-7-chloro-3,4-dihydroacridine-1,9(2H,10H)-dione 1-oximes and 1-hydrazone derivatives of the formula I ##STR1## and their physiologically tolerated acid addition and ammonium salts are described, as is a process for their preparation. The new compounds are chemotherapeutic agents and are active against protozoa, especially malaria plasmodia.
    Type: Grant
    Filed: October 11, 1983
    Date of Patent: June 3, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erhardt Winklemann, Walter Durckheimer, Wolfgang Raether
  • Patent number: 4590277
    Abstract: 4-Carboxamidoacridine compounds represented by the general formula (I), ##STR1## where R.sub.1 represents H, CH.sub.3 or NHR.sub.3, where R.sub.3 is H, COCH.sub.3, SO.sub.2 CH.sub.3, COPh, SO.sub.2 Ph or lower alkyl optionally substituted with hydroxyl and/or amino functions;R.sub.2 represents H or up to two of the groups CH.sub.3, OCH.sub.3, halogen, CF.sub.3, NO.sub.2, NH.sub.2, NHCOCH.sub.3, and NHCOOCH.sub.3 placed at positions 1-3 or 5-8;Y represents C(NH)NH.sub.2, NHC(NH)NH.sub.2, or NR.sub.4 R.sub.5, where each of R.sub.4 and R.sub.5 is H or lower alkyl optionally substituted with hydroxyl and/or amino functions; andx is from 2 to 6,and the acid addition salts thereof, possess antibacterial and antitumor properties.
    Type: Grant
    Filed: June 21, 1983
    Date of Patent: May 20, 1986
    Assignee: Development Finance Corporation of New Zealand
    Inventors: Graham J. Atwell, Bruce C. Baguley, William A. Denny, Gordon W. Rewcastle
  • Patent number: 4588730
    Abstract: Pyrazolo[3,4,5-k1]acridines are described as antibacterial agents and antitumor agents as well as pharmaceutical compositions and methods for their preparation.
    Type: Grant
    Filed: August 22, 1985
    Date of Patent: May 13, 1986
    Assignee: Warner-Lambert Company
    Inventor: David B. Capps
  • Patent number: 4575553
    Abstract: The compounds are of the class of 9-anilinoacridines, useful as antitumor agents and are analogs of m-AMSA. These compounds have the formula ##STR1## in which R.sup.1 is Br, Cl or CH.sub.3, and R.sup.2 is CH.sub.2 NHCH.sub.3, CH.sub.2 N(CHO)CH.sub.3 or CH.sub.2 NHCHO. Intermediate 3-substituted-9(10H)acridone-5-carboxylic acids are prepared by converting diphenylaminedicarboxylic acids via acyl chloride to dipiperidides, purifying the dipiperidides, treating said dipiperidides with phosphorous oxychloride in an inert organic solvent at a temperature in the range of about 70.degree. C. to 110.degree. C. to yield 9-acridine, subjecting said 9-acridine to mild acid hydroylsis to yield 9-acridone and thereafter hydroylzing said 9-acridones to the acid product.
    Type: Grant
    Filed: June 18, 1984
    Date of Patent: March 11, 1986
    Assignee: Bristol-Myers Company
    Inventors: Gerry Kavadias, Terrance W. Doyle, Elizabeth Janik, Richard A. Partyka
  • Patent number: 4544746
    Abstract: A process is disclosed wherein 2,5-di(phenylamino) terephthalic acid is half-cyclized by dissolving it in a mixture of polyphosphoric acid and phosphoric acid and heating at 100.degree.-120.degree. C. to form 2-(phenyl)amino-3-carboxy-9(10H)acridone (ACA). The ACA is decarboxylated to form 2-(phenyl)amino-9(10H)acridone, also known as 2-anilinoacridone, by dissolving it in tetramethylene sulfone and heating in the presence of a basic cupric carbonate catalyst.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: October 1, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Wilfried G. Holtje
  • Patent number: 4374984
    Abstract: Compounds of the formula ##STR1## wherein the substituents A, Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4, X, n and m are defined hereinbeloware effective photoinitiators, especially for the photopolymerization of ethylenically unsaturated compounds and for the curing of printing inks.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: February 22, 1983
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Jurgen Eichler, Claus Herz, Karl-Heinz Neisius, Gregor Wehner
  • Patent number: 4366102
    Abstract: In a process for the preparation of an aromatic chloroformic acid ester by contacting a phenol and phosgene, the improvement wherein the reaction is carried out in a homogeneous liquid phase at a temperature of 60.degree. to 180.degree. C. in the presence of organic phosphorus compound of the formulaR.sup.1 R.sup.2 R.sup.3 PR.sup.4.sub.n X.sub.nin whichR.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, alkyl, alkenyl, aralkyl, aryl or halogen and two of the said radicals together with the phosphorus atom can form a 5-membered or 6-membered phosphorus-containing saturated or unsaturated heterocyclic radical,X represents OH, homopolar-bonded halogen or an inorganic or organic acid anion,R.sup.4 denotes hydrogen or alkyl or, if X denotes halogen, can also denote halogen and n denotes 0 or 1,and in which, furthermore,R.sup.4 and X together can represent oxygen or sulfur.
    Type: Grant
    Filed: May 6, 1981
    Date of Patent: December 28, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Rauchschwalbe, Heinz U. Blank, Karl Mannes, Dietmar Mayer
  • Patent number: 4291034
    Abstract: 7-Chloro-3-substituted aryl-3,4-dihydro-1,9-(2H,1OH) and 10-hydroxy-acridinedioneimines and their pharmaceutically acceptable salts and a process for preparing them are disclosed and claimed. The compounds are useful in the treatment of protozoan diseases.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 22, 1981
    Assignee: Warner Lambert Company
    Inventor: Leslie M. Werbel
  • Patent number: 4258190
    Abstract: A process for preparing cyclohexanonecarboxylate ester intermediates for the preparation of 1,2,3,4-tetrahydro-7-(phenyl)amino-9(10H)acridinone and 2-(phenyl)amino-9(10H)acridinone and for preparing said acridinones.
    Type: Grant
    Filed: August 29, 1979
    Date of Patent: March 24, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Arthur J. Taggi
  • Patent number: 4250294
    Abstract: A polymer having aromatic or heterocyclic rings as the only structural elements said aromatic or heterocyclic rings containing at least two nitro groups is disclosed as well as a method of preparing the same. The polymers are useful as binding agents for thermo stable propellants and can be easily formed into films. They remain thermally stable up to temperatures of at least 200.degree. C.
    Type: Grant
    Filed: November 22, 1978
    Date of Patent: February 10, 1981
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Rainer Hagel, Klaus Redecker
  • Patent number: 4244954
    Abstract: 9-Phenyl(or benzyl)acridines, 9-phenyl(or benzyl)-9-acridinols and acridinium compounds, useful as trypanosomacidal and antibacterial agents, are prepared from aminoalkoxy substituted 9-acridinones via reaction with the appropriate Grignard reagents or aryllithium. The intermediate aminoalkoxy substituted 9-acridinones, prepared from the corresponding halo or hydroxy substituted 9-acridinones, are useful as antiviral agents.
    Type: Grant
    Filed: October 2, 1978
    Date of Patent: January 13, 1981
    Assignee: Sterling Drug Inc.
    Inventor: John W. Schulenberg
  • Patent number: 4165319
    Abstract: Bis-isoindoline pigments of the formula ##STR1## wherein A represents a carbocyclic or heterocyclic aromatic radical,Q represents an oxygen atom or an imino group,E represents a cyano or acetyl group, a group of the formula --COOR, wherein R represents a C.sub.1 -C.sub.4 -alkyl group or a phenyl group which is unsubstituted or substituted in the o-, p- or m-position by halogen atoms, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy groups, or represents a group of the formula --CONHR.sub.1, wherein R.sub.1 represents a hydrogen atom, a C.sub.1 -C.sub.4 -alkyl group or a phenyl group which is unsubstituted or substituted in the o-, p- or m-position by halogen atoms or C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy groups,X represents a hydrogen atom,Y represents a chlorine or bromine atom,M and n are integers from 0 to 4,P is an integer from 0 to 1, while the sum of m+n+p must be 4, andZ if p is 1 and m is 3, represents a nitro or C.sub.2 -C.sub.
    Type: Grant
    Filed: July 18, 1977
    Date of Patent: August 21, 1979
    Assignee: Ciba-Geigy Corporation
    Inventors: Jost von der Crone, Christoph Frey
  • Patent number: 4150134
    Abstract: 9-Phenyl(or benzyl)acridines, 9-phenyl(or benzyl)-9-acridinols and acridinium compounds, useful as trypanosomacidal and antibacterial agents, are prepared from dialkylaminoalkoxy substituted 9-acridinones via reaction with the appropriate Grignard reagents or aryllithium.
    Type: Grant
    Filed: March 4, 1977
    Date of Patent: April 17, 1979
    Assignee: Sterling Drug Inc.
    Inventor: John W. Schulenberg
  • Patent number: 4131673
    Abstract: N.sup.2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis in mammals.
    Type: Grant
    Filed: June 7, 1977
    Date of Patent: December 26, 1978
    Assignees: Mitsubishi Chemical Industries, Limited, Shosuke Okamoto
    Inventors: Shosuke Okamoto, Akiko Hijikata, Ryoji Kikumoto, Yoshikuni Tamao, Kazuo Ohkubo, Tohru Tezuka, Shinji Tonomura
  • Patent number: 4127573
    Abstract: Acridone and xanthone compounds substituted by at least one tetrazolyl group in one ring, and further substituted in the other ring, optionally for the acridones have antiallergic activity.
    Type: Grant
    Filed: September 5, 1973
    Date of Patent: November 28, 1978
    Assignee: Burroughs Wellcome Co.
    Inventor: John H. Gorvin