Plural Six-membered Hetero Rings Patents (Class 549/415)
  • Patent number: 5959157
    Abstract: A process for making ethynylated, hydroxy-substituted biphenyl compounds comprising:a) halogenating 3,3'-dimethoxybiphenyl to form 2,2'-dihalo-5,5'-dimethoxybiphenyl;b) reacting the resulting 2,2'-dihalo-5,5'-dimethoxybiphenyl with a bromide-containing compound in a chlorinated solvent to form 2,2'-dihalo-5,5'-dihydroxybiphenyl;c) reacting the resulting 2,2'-dihalo-5,5'-dihydroxybiphenyl with a hydroxyl-containing compound in the presence of a protection catalyst to form 2,2'-dihalo-5,5'-bis(tetrahydropyranoxy)biphenyl;d) ethynylating the resulting 2,2'-dihalo-5,5'-bis(tetrahydropyranoxy)biphenyl with a compound of the formulaCuC.tbd.CR'wherein R' is comprised of an alkyl group having from about 1 to about 20 carbon atoms, an alkenyl group having from about 1 to about 20 carbon atoms, an aryl group, a heteroaryl group, or mixtures thereof to form 2,2'-bis(C.tbd.CR')-5,5'-bis(tetrahydropyranoxy)biphenyl; ande) hydrolyzing the resulting 2,2'-bis(C.tbd.
    Type: Grant
    Filed: June 14, 1996
    Date of Patent: September 28, 1999
    Assignee: Alliedsignal, Inc.
    Inventors: Kreisler Lau, Neil Hendricks, William Wan, Aaron Smith
  • Patent number: 5919768
    Abstract: The present invention provides compounds having structure (II), and the pharmaceutically acceptable salts, esters, amides and prodrugs thereof.
    Type: Grant
    Filed: February 11, 1998
    Date of Patent: July 6, 1999
    Assignee: Texas Biotechnology Corporation
    Inventors: Timothy P. Kogan, Brian Dupre, Ian L. Scott, Huong Bui, Kathy L. Wheeler, Karin M. Keller, Jamal M. Kassir
  • Patent number: 5912363
    Abstract: A method for the extraction of proanthocyanidins from plant material is disclosed. The method involves heating an aqueous mixture of solid plant material, optionally under increased pressure and reduced oxygen; various separation, filtration and adsorption steps, and the elution of adsorbed proanthocyanidins with polar solvent. Optionally, the polar solvent can be reconstituted and recycled into the elution phase of the method, resulting in decreased solvent consumption.
    Type: Grant
    Filed: August 29, 1997
    Date of Patent: June 15, 1999
    Assignee: Interhealth Nutraceuticals
    Inventors: Karim Nafisi-Movaghar, Thomas T. Svanoe, William A. Seroy
  • Patent number: 5908860
    Abstract: This invention relates to the method of treatment and/or prophylaxis of anxiety and/or disorders treatable and/or preventable with anti-convulsive agents, such as epilepsy, using compounds of the formula (Ia): ##STR1##
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: June 1, 1999
    Assignees: SmithKline Beecham plc,, SmithKline Beecham Corporation
    Inventors: Mervyn Thompson, John Morris Evans, Neil Upton, Wai Ngor Chan, Kuok Keong Vong, Robert Nicholas Willette
  • Patent number: 5908581
    Abstract: A red fluorescent material includes a compound of the formula: ##STR1## wherein: R.sub.1, and R.sub.2 are individually alkyl of from 1 to 20 carbon atoms, aryl, carbocyclic and other heterocyclic systems; andR.sub.3, and R.sub.4 are individually alkyl of from 1 to 10 carbon atoms, and a branched or unbranched 5 or 6 member substituent ring connecting with R.sub.1, R.sub.2 respectively; andR.sub.5 is alkyl of from 2-20 carbon atoms; sterically hindered aryl and heteroaryl; andR.sub.6 is alkyl of from 1 to 10 carbon atoms, and a 5 or 6-member carbocyclic ring connecting with R.sub.5.
    Type: Grant
    Filed: April 7, 1997
    Date of Patent: June 1, 1999
    Assignee: Eastman Kodak Company
    Inventors: Chin H. Chen, Kevin P. Klubek, Jianmin Shi
  • Patent number: 5863773
    Abstract: Disclosed are novel antifungal agents having the formula: ##STR1## as well as a pharmaceutically acceptable salt, ester of prodrug thereof, whereinR is: ##STR2## --C(O)--R.sub.1 wherein R.sub.1 is alkyl, alkenyl, aryl, arylalkenyl, aryl-aryl-, arylalkoxy-aryl-, aryl-aryl-aryl-, arylkoxy-aryl-aryl-, or ##STR3## wherein R.sub.2 is alkylamino, dialkylamino, (heterocyclic)alkyl, aryl, or arylalkyl; andX is O, NH, or NR.sub.3 wherein R.sub.3 is alkyl or aryl. Also disclosed are pharmaceutical compositions comprising a compound of the invention in combination with a pharmaceutically acceptable carrier; and a process for preparing the compounds of the invention.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: January 26, 1999
    Assignee: Abbott Laboratories
    Inventors: Geewananda P. Gunawardana, David Frost, Marianna Jackson, James P. Karwowski, Ronald R. Rasmussen
  • Patent number: 5854219
    Abstract: The invention relates to 9-N-ethenyl derivatives of 9 (S)-erythromycylamine, new semisynthetic antibiotics of the macrolide class of the general formula (I) ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and represent nitryl, a carboxyl group of the formula COOR.sup.3, wherein R.sup.3 represents a C.sub.1 -C.sub.4 alkyl group, or a keto group of the formula COR.sup.4, wherein R.sup.4 represents a C.sub.1 -C.sub.4 alkyl group, to their pharmaceutically acceptable addition salts with inorganic or organic acids, to a process for their preparation, to a process for the preparation of the pharmaceutical compositions as well as to the use of the obtained pharmaceutical compositions in the treatment of bacterial infections.
    Type: Grant
    Filed: October 23, 1997
    Date of Patent: December 29, 1998
    Assignee: PLIVA, farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvo
    Inventors: Nedjeljko Kujundzic, Dina Pavlovic, Gabrijela Kobrehel, Gorjana Lazarevski, Zeljko Kelneric
  • Patent number: 5849216
    Abstract: Compounds of the formula (I)R.sup.1 --(A.sup.1).sub.a (--M.sup.1).sub.b --(--A.sup.2).sub.c (--M.sup.2).sub.d (--A.sup.3).sub.e (--M.sup.3).sub.f (--A.sup.4).sub.g --H(I)in which the symbols and indices have the following meanings:R.sup.1 is B or a straight-chain or branched alkyl radical having 1 to 22 carbon atoms (with or without an asymmetrical carbon atom) in which, in addition, it is possible for one or two non-adjacent --CH.sub.2 -- groups to be replaced by --O--, --S--, --CO--, --CO--O--, --O--CO--, --CO--S--, --S--CO--, --O--CO--O--, --CH.dbd.CH--, --C.tbd.C--, .DELTA. or --Si(CH.sub.3).sub.2 --, and in which, in addition, one or more hydrogen atoms of the alkyl radical may be substituted by F, Cl, Br or CN, or is a chiral group, for example an epoxide, a dioxolane or a cyclic lactone,--(A.sup.1).sub.a (--M.sup.1).sub.b --(--A.sup.2).sub.c (--M.sup.2).sub.d (--A.sup.3).sub.e (--M.sup.3).sub.f (--A.sup.4).sub.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: December 15, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerd Illian, Anke Kaltbeitzel, Rainer Wingen, Hubert Schlosser
  • Patent number: 5811028
    Abstract: A 2H-5,6-optically active dihydropyran derivative represented by the general formula (I) or (I'): ##STR1## wherein Rf represents a fluoroalkyl group having 1 or 2 carbon atoms; a liquid crystal composition and a liquid crystal device comprising the derivative; and a racemic mixture comprising at least one type of the derivative. The derivative is a novel compound which exhibits the liquid crystal property by itself or can be used as an excellent dopant providing a high speed response to a composition comprising it even when the compound does not exhibit the liquid crystal property by itself. The derivative also exhibits a large spontaneous polarization.
    Type: Grant
    Filed: August 13, 1997
    Date of Patent: September 22, 1998
    Assignee: Kashima Oil Company
    Inventors: Tatsushi Ishizuka, Mitsunori Takeda, Masaaki Namekawa, Keizou Itoh
  • Patent number: 5795981
    Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an aromatic unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an acyl, aliphatic, cycloaliphatic, aromatic or heterocyclic group, subject to the proviso that one of R.sup.3 and R.sup.4 may be an amino or substituted amino group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a nitrogenous heterocyclic ring) are useful as near infra-red absorbers.
    Type: Grant
    Filed: December 16, 1996
    Date of Patent: August 18, 1998
    Assignee: Polaroid Corporation
    Inventors: John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
  • Patent number: 5780633
    Abstract: A new process for preparing a compound of the formula: ##STR1##
    Type: Grant
    Filed: May 6, 1996
    Date of Patent: July 14, 1998
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Satoshi Okada, Kozo Sawada, Akio Kuroda, Shinya Watanabe, Hirokazu Tanaka
  • Patent number: 5780644
    Abstract: Branched, dendrimeric-type macromolecules composed essentially of a central nucleus and of a series of polyoxaalkyl chains that depart from said nucleus and spread into the surrounding space branching in a cascade fashion useful as carriers of drugs, contrast agents, etc.
    Type: Grant
    Filed: March 15, 1995
    Date of Patent: July 14, 1998
    Assignee: Dibra S.p.A.
    Inventors: Luigia Gozzini, Monica Muttoni, Christoph DeHaen
  • Patent number: 5766610
    Abstract: Novel pharmaceutically/cosmetically-active polycyclic aromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a)-(e): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: June 16, 1998
    Assignee: Centre International De Recherches Dermatologiques Galderma
    Inventor: Jean-Michel Bernardon
  • Patent number: 5756472
    Abstract: There is disclosed a novel compound having the formula ##STR1## which exhibits antifungal activity.
    Type: Grant
    Filed: January 27, 1997
    Date of Patent: May 26, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Jerrold M. Liesch, Maria S. Meinz, Janet C. Onishi, Sandra A. Morris, Robert E. Schwartz, Gerald F. Bills, Robert A. Giacobbe, Wendy S. Horn, Deborah L. Zink, Angeles Cabello, Maria T. Diez, Isabella Martin, Fernando Pelaez, Francisca Vicente
  • Patent number: 5719179
    Abstract: Disclosed is Compound GEX1 of formula (I), having excellent antitumor activity: ##STR1## wherein R.sup.1 represents hydroxy or ##STR2## R.sup.2, R.sup.3 and R.sup.4 independently represent hydrogen or hydroxy; R.sup.5 represents hydroxyl or lower alkoxy; provided that when R.sup.1 is hydroxy and R.sup.5 is methoxy, then at least one of R.sup.2, R.sup.3 and R.sup.4 is the group except for hydrogen, and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: December 24, 1996
    Date of Patent: February 17, 1998
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Tamio Mizukami, Yasushi Sakai, Tetsuo Yoshida, Youichi Uosaki, Keiko Ochiai, Shiro Akinaga
  • Patent number: 5705659
    Abstract: Intermediate compounds represented as formula (I) useful for the synthesis of 16-phenoxy-prostatrienoic acid derivatives and a preparing method thereof are disclosed. ##STR1## wherein R is tetrahydropyranyl, tetrahydrofuranyl, 2-ethoxyethyl, t-butyldimethylsilyl, triisopropylsilyl or triethylsilyl group; R.sup.1 and R.sup.2 are independently hydrogen or ester-forming group; P is hydrogen, trimethylsilyl or tri-n-butyltin; and wavy line means epi-stereoisomeric mixture.
    Type: Grant
    Filed: June 20, 1996
    Date of Patent: January 6, 1998
    Assignee: Korea Institute of Science and Technology
    Inventors: Hokoon Park, Sun Ho Jung, Yong Sup Lee, Ki Hong Nam
  • Patent number: 5668261
    Abstract: A process for preparing carboxylates of polyoxyalkylene siloxanes and -amines, alkylpolyoxyalkylenes, polyoxyalkylene block polymers, alkylamidepolyoxyalkylenes and alkylpolyglucosides comprising subjecting a primary hydroxyl group-containing polyoxyalkylene compound or alkylpolyglucoside to mild oxidiation. The invention also relates to the novel polyoxyalkylene amine and alkylamidepolyoxyalkylene carboxylates prepared by the process.
    Type: Grant
    Filed: March 7, 1996
    Date of Patent: September 16, 1997
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Parfait J. M. Likibi, Robert V. Casciani, Gregory L. McCraw
  • Patent number: 5656750
    Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an aromatic unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an acyl, aliphatic, cycloaliphatic, aromatic or heterocyclic group, subject to the proviso that one of R.sup.3 and R.sup.4 may be an amino or substituted amino group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a nitrogenous heterocyclic ring) are useful as near infra-red absorbers.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: August 12, 1997
    Assignee: Polaroid Corporation
    Inventors: Richard M. Allen, Peter K. Chu
  • Patent number: 5597938
    Abstract: A novel process for the production of a compound represented by the formula: ##STR1## wherein Z and Z' each represents a protective group for the hydroxyl group; R.sup.1 represents a hydrogen atom or an alkyl group; R.sup.2 represents an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a group represented by the formula --B--D (in which B is an alkylene group and D is a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenoxy group or a cycloalkyl group), a substituted or unsubstituted phenyl group or a substituted or unsubstituted phenoxy group; R.sup.3 and R.sup.4 each represents a hydrogen atom, an alkyl group or an alkoxy group; R.sup.5 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a cyano group, an amino group, a hydroxyl group or a group represented by a formula --COOR.sup.8 ; R.sup.6 represents a group represented by a formula --COOR.sup.9, a cyano group, a hydroxyl group, a group represented by a formula --OCOR.sup.
    Type: Grant
    Filed: August 10, 1995
    Date of Patent: January 28, 1997
    Assignees: Taisho Pharmaceutical Co., Ltd., Fumie Sato
    Inventor: Fumie Sato
  • Patent number: 5597932
    Abstract: The invention is drawn to a compound having the following formula ##STR1## in which X.sup.1 and X.sup.2, which may be the same or different, represent hydrogen or a hydroxy-protecting group, X.sup.4 is hydrogen, A is selected from --COOAlkyl and CH.sub.2 OH, and B is a hydroxy group, or A and B, when taken together, represent an oxo group. These compounds are useful as intermediates in the production of 19-nor vitamin D derivatives.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: January 28, 1997
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman, Rolf E. Swenson
  • Patent number: 5573999
    Abstract: .beta.-Substituted cinnamic acid derivatives of the formula 1, ##STR1## where R.sup.1 is alkyl, chlorine or bromine, --X-- is --O--, --S--, ##STR2## m is 0 or 1, --Y is --OR.sup.4, --O--N.dbd.CR.sup.5 R.sup.6, --NR.sup.7 R.sup.8, --N(OR.sup.9)R.sup.10 or --SR.sup.11, where the above-mentioned substituents R.sup.2 to R.sup.11 are alkyl, and R.sup.2, and R.sup.3 and R.sup.5 to R.sup.11 can also be hydrogen,Z is halogen, nitro, cyano, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, arylthioalkyl, hetarylalkyl, hetaryloxyalkyl, hetarylthioalkyl, alkenyl, aralkenyl, aryloxyalkenyl, arylthioalkenyl, hetarylalkenyl, hetaryloxyalkenyl, hetarylthioalkenyl, alkynyl, arylalkynyl, hetarylalkynyl, aryl, hetaryl, arylazo, acylamino, --OR.sup.12, --SR.sup.13, --SOR.sup.14, --SO.sub.2 R.sup.15, --COOR.sup.16, --CONR.sup.17 R.sup.18, --COR.sup.19, --CR.sup.20 .dbd.NR.sup.21, --N.dbd.CR.sup.22, R.sup.23, --CR.sup.24 .dbd.N--OR.sup.25, --CR.sup.25 R.sup.26 --O--, N.dbd.CR.sup.27 R.sup.28, --CH.sub.2 --OCOR.sup.39 or --NR.sup.37 R.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: November 12, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Sauter, Herbert Bayer, Klaus Oberdorf, Horst Wingert, Wolfgang von Deyn, Wassilios Grammenos, Hartmann Koenig, Harald Rang, Franz Roehl, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5571936
    Abstract: Intermediate compounds represented as formula (I) useful for the synthesis of 16-phenoxy-prostatrienoic acid derivatives and a preparing method thereof are disclosed. ##STR1## wherein R is tetrahydropyranyl, tetrahydrofuranyl, 2-ethoxyethyl, 3-t-butyldimethylsilyl triisopropylsilyl or triethylsilyl group; R.sup.1 and R.sup.2 are independently hydrogen or ester-forming group; P is hydrogen, trimethylsilyl or tri-n-butyltin; and wavy line means epistereoisomeric mixture.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: November 5, 1996
    Assignee: Korea Institute of Science and Technology
    Inventors: Hokoon Park, Sun Ho Jung, Yong Sup Lee, Ki Hong Nam
  • Patent number: 5565129
    Abstract: The polycarbonates of the present invention include those of sucrose series having a specific cyclic structure, those of oligosaccharide and monosaccharide series other than the sucrose series, those derived from specific saccharides having no cyclic structure, those having a skeletal structure of pentaerythritol, neopentyl glycol or trimethylolmethane, and specific dicarbonates.The lubricating oil and electrical insulating oil of the invention contain the above-mentioned polycarbonates.The polycarbonates of the invention are excellent in compatibility with Freon R-134a (HFC) as well as in lubricating properties, detergency and electrical insulating properties, and are capable of providing lubricating oil for refrigerator, automotive engine oil, automotive gear oil, lubricating oil for rolling and lubricating oil for fiber, especially lubricating oil for which electrical insulating properties are required, and electrical insulating oil.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: October 15, 1996
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Masahide Tanaka, Tadaaki Fujimoto, Tetsuo Hayashi, Takashi Hayashi, Kazunori Takahata
  • Patent number: 5536745
    Abstract: Conformationally restricted aryl and heteroaryl ketones derived from monic acid have useful antibacterial properties.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: July 16, 1996
    Assignee: SmithKline Beecham p.l.c.
    Inventor: Neil D. Pearson
  • Patent number: 5536850
    Abstract: The present invention relates to a novel substance DC114-A1 represented by the following formula (I): ##STR1##
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: July 16, 1996
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Hirofumi Nakano, Noboru Fujii, Tamio Mizukami, Youichi Uosaki, Katsunori Kita, Eiji Kobayashi
  • Patent number: 5527805
    Abstract: A fused ring system compound is disclosed that contains an epoxide group on one side of the fused rings and an enediyne macrocyclic ring on the other side of the fused rings. The compounds have DNA-cleaving, antimicrobial and tumor growth-inhibiting properties. Chimeric compounds having the fused ring system compound as an aglycone bonded to (i) a sugar moiety as the oligosaccharide portion or (ii) a monoclonal antibody or antibody combining site portion thereof that immunoreacts with target tumor cells are also disclosed. Compositions containing a compound or a chimer are disclosed, as are methods of preparing a compound.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: June 18, 1996
    Assignee: The Scripps Research Institute
    Inventors: Adrian L. Smith, Chan-Kou Hwang, Sebastian V. Wendeborn, Kyriacos C. Nicolaou, Erwin P. Schreiner, Wilhelm Stahl, Wei-Min Dai, Peter E. Maligres, Toshio Suzuki
  • Patent number: 5525745
    Abstract: The invention describes intermediates for use in the synthesis of 1.alpha.-hydroxy-19-nor-vitamin D compounds. The intermediates have the following formula: ##STR1## The disclosed process includes (a) the construction of a 5,8-diol-6-yne intermediate by joining ring-A and ring-C/D portions of the desired end product via the condensation of an acetylenic derivative containing the C/D-ring portion of the desired end product with a cyclic dihydroxy ketone representing the A-ring of the desired end product; (b) the partial reduction of the 6,7 acetylenic triple bond linkage between the A and C/D ring portions to obtain a 5,8-diol-6-ene intermediate; and (c) the reductive removal of the 5,8-oxygen functions to generate the required 5,7-diene end product from which the desired 7-trans(7E)-isomer is purified directly, or after optional double bond isomerization of the 7-cis(7Z)-isomer employing a novel thiophenol-promoted isomerization step.
    Type: Grant
    Filed: March 27, 1995
    Date of Patent: June 11, 1996
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Hector F. DeLuca, Heinrich K. Schnoes, Fariba Aria
  • Patent number: 5496943
    Abstract: Disclosed is a novel heterocyclic compound selected from the group consisting of the compounds [IV] to [VII], [IX] and [X]. The heterocyclic compound is useful for reactive materials in chemical industry. A process for producing the heterocyclic compound is also disclosed.
    Type: Grant
    Filed: March 13, 1992
    Date of Patent: March 5, 1996
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Otohiko Tsuge, Taizo Hatta, Satoshi Urano, Noriyuki Tsuboniwa, Ryuzo Mizuguchi
  • Patent number: 5457125
    Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 is hydrogen, (1-4C)alkyl, halogeno-(2-4C)alkyl, hydroxy-(2-4C)alkyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl;R.sup.5 is hydrogen, (1-4C)alkyl, halogeno-(2-4C)alkyl, hydroxy-(2-4C)alkyl, cyano-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, or a heteroaryl moiety selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, furyl, thienyl, oxazolyl and thiazolyl;A.sup.4 is (1-4C)alkylene;Ar.sup.1 is phenylene, pyridinediyl or pyrimidinediyl;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene, pyridinediyl, pyrimidinediyl, thiophenediyl, furandiyl or thiazolediyl;R.sup.1 is hydrogen, (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- wherein each of A.sup.2 and A.sup.3 is independently (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: August 19, 1994
    Date of Patent: October 10, 1995
    Assignees: Zeneca Limited, Zeneca Pharma S.A.
    Inventors: Philip N. Edwards, Michael S. Large
  • Patent number: 5436352
    Abstract: The present invention provides metal chelating compounds, to chelates and chelate-targeting agent conjugates formed from the chelating compounds, and to methods for making and using these compositions. The chelating compounds incorporate two nitrogen atoms and three sulfur atoms ("N.sub.2 S.sub.3 "), two nitrogen atoms and four sulfur atoms ("N.sub.2 S.sub.4 "), or three nitrogen atoms and three sulfur atoms ("N.sub.3 S.sub.3 "). Metals, and metal oxides, capable of being chelated by the compounds include those that are radionuclides, such as .sup.99m Tc and .sup.186/188 Re.The targeting agent portion of the chelate-targeting agent conjugates provided includes antibodies, peptides, hormones, enzymes and biological response modifiers. Methods for making the conjugates are provided and encompass the addition of a metal, or metal oxide, to a chelating compound prior to attachment to a targeting agent as well as subsequent to the attachment.
    Type: Grant
    Filed: December 6, 1991
    Date of Patent: July 25, 1995
    Assignee: NeoRx Corporation
    Inventors: Ananthachari Srinivasan, Alan R. Fritzberg, David S. Jones
  • Patent number: 5405968
    Abstract: Methine dyes with a polyketo group I ##STR1## where A is ##STR2## R.sup.1 is a 5- or 6-membered cycloaliphatic radical which contains one or two hetero atoms from the group --NR.sup.4 --, --O-- and --S-- and which may be fused to an isoaromatic or heteroaromatic group, R.sup.2 and R.sup.3 are identical or different C.sub.1 -C.sub.10 -alkyl groups or together one of the radicals R.sup.1, and m and n are identical or different integers from 0 to 3, are useful as drugs, for producing singlet oxygen, as sensitizers in electrophotographic layers and for photopolymerizations and as laser light sensitive dyes in optical recording media; also novel triketo- and tetraketomethine dyes.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: April 11, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Albert, Knut Kessel, Hans-Dieter Martin, Stefan Silber
  • Patent number: 5405870
    Abstract: Compounds of formula (Ic): ##STR1## having valuable platelet-aggregation inhibitory activities useful for the prophylaxis and treatment of such diseases as thrombosis and pharmaceutical compositions containing said compounds.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: April 11, 1995
    Assignee: Sankyo Company, Limited
    Inventors: Kazuo Koyama, Shigeo Amemiya, Koichi Kojima, Shinsaku Kobayashi
  • Patent number: 5405976
    Abstract: Dyes comprising an inner salt of a compound of the formula:Q.sup.1 =Z-Q.sup.2wherein:Q.sup.1 is a 4-(benz[b]-4H-pyrylium)methylidene, 4-(benz[b]-4H-thiopyrylium)methylidene or 4-(benz[b]-4H-selenopyrylium)methylidene grouping;Z is a 1,3-(2-hydroxy-4-oxo-2-cyclobutylidene) hydroxide or 1,3-(2-hydroxy-4,5-dioxo-2-cyclopentylidene) hydroxide ring; andQ.sup.2 is a 4-(benz[b]-4H-pyran-4-ylidene)methyl, 4-(benz[b]-4H-thiopyran-4-ylidene)methyl or 4-(benz[b]-4H-selenopyran-4-ylidene)methyl grouping;wherein at least one of the groupings Q.sup.1 and Q.sup.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: April 11, 1995
    Assignee: Polaroid Corporation
    Inventors: Stephen J. Telfer, Robert P. Short, Stephen G. Stroud, Anthony J. Puttick, Socorro Ramos, Michael J. Zuraw
  • Patent number: 5395854
    Abstract: Ortho-substituted phenyl-acetamides I ##STR1## (R.sup.1 =H, alkyl, cycloalkyl, alkenyl, alkynyl, phenylalkynyl, alkoxyalkyl, alkoxycarbonyl, phenyl, phenylalkyl, phenylalkenyl or phenoxyalkyl, 5- or 6-membered heterocycle with 1-3 hetero atoms to which a benzene ring or a 5- or 6-membered heterocycle can be fused; R.sup.2 and R.sup.3 =H, CN, halogen, alkyl, alkoxy; R.sub.4 and R.sup.5 =H, alkyl and R.sup.4 or R.sup.5 =alkoxy; Y=O, S, SO, SO.sub.2, N=N, O--CO, CO--O, CO--O--CH.sub.2, alkylene or haloalkylene, alkenylene, alkynylene, oxy- alkylene, thio-alkylene, alkyleneoxy, carbonylalkylene or alkylenecarbonyl, W=alkoxyimino, alkoxymethylene or alkylthiomethylene), excepting compounds where R.sup.1 is hydrogen, phenyl or 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropyl, R.sup.2 to R.sup.5 are each hydrogen, Y is carbonyloxymethylene and W is methoxymethylene or methylthiomethylene, are suitable as fungicides and for controlling pests.
    Type: Grant
    Filed: September 22, 1993
    Date of Patent: March 7, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Siegbert Brand, Eberhard Ammermann, Gisela Lorenz, Hubert Sauter, Klaus Oberdorf, Uwe Kardorff, Christoph Kuenast
  • Patent number: 5384412
    Abstract: Intermediates useful in preparing the calicheamicin and esperamicin oligosaccharides, and particularly the sulfur- and O-substituted hydroxylamine-containing B ring of both oligosaccharides, are disclosed as are methods of making and using the same, including the preparation of chimeric antibiotics using the same.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: January 24, 1995
    Assignee: The Scripps Research Institute
    Inventors: Kyriacos C. Nicolaou, Robert D. Groneberg, Erwin P. Schreiner, Wilhelm Stahl
  • Patent number: 5380881
    Abstract: Non-polymeric compounds which contain at least one aromatic ring system carrying one or more one or more tetrahydropyranyloxy substituents of formula I ##STR1## wherein R.sub.1 is hydrogen, halogen, alkyl, cycloalkyl, aryl, alkoxy or aryloxy,R.sub.2 is hydrogen, alkyl, cycloalkyl or aryl,R.sub.3 is a saturated or unsaturated hydrocarbon radical,R.sub.4 and R.sub.5 are each independently of the other hydrogen, halogen, alkyl, alkoxy or aryloxy, andX is a direct single bond or a methylene or ethylene bridge.These compounds are especially suitable for the preparation of photoresist compositions which can be used both for the production of positive as well as negative images. The photoresists are preferably used for deep-UV microlithography.
    Type: Grant
    Filed: January 22, 1993
    Date of Patent: January 10, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Ulrich Schadeli
  • Patent number: 5374654
    Abstract: The invention relates to carbacyclin derivatives of Formula I ##STR1## wherein the various substituents are defined herein, including, inter alia,if R.sub.2 is a hydrogen atom, their salts with physiologically compatible bases, their cyclodextrin clathrates, and their use as medicinal agents.
    Type: Grant
    Filed: April 21, 1993
    Date of Patent: December 20, 1994
    Assignee: Schering Aktiengesellschaft
    Inventors: Helmut Vorbruggen, Ulrich Klar, Bob Nieuweboer, Claus-Steffen Sturzebecher
  • Patent number: 5371222
    Abstract: A fungicidal composition for agricultural use, which comprises a compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each hydrogen, lower alkyl or cyclo(lower)alkyl; R.sup.3 is lower alkyl or cyclo(lower)alkyl; R.sup.4 and R.sup.5 are each hydrogen, lower alkyl, lower alkoxy, halogen-substituted lower alkyl, lower alkyl-substituted silyl, halogen or nitro; A represents an unsaturated hydrocarbon group, a halogen-substituted unsaturated hydrocarbon group, a phenyl group or a heterocyclic group, among which the phenyl group and the heterocyclic group may be optionally substituted with not more than three substituents; and Z is --CH.sub.2 --, --CH(OH)--, --CO--, --O--, --S--, --NR-- (R being hydrogen or lower alkyl), --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, ##STR2## --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 SO--, --OCH.sub.2 --, --SCH.sub.2 -- or --SOCH.sub.2 --.
    Type: Grant
    Filed: October 16, 1992
    Date of Patent: December 6, 1994
    Assignee: Shionogi Seiyaku Kabushiki Kaisha
    Inventors: Yoshio Hayase, Takahiro Kataoka, Hideyuki Takenaka, Mitsuhiro Ichinari, Michio Masuko, Toshio Takahashi, Norihiko Tanimoto
  • Patent number: 5371223
    Abstract: A fungicidal composition for agricultural use, which comprises a compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each hydrogen, lower alkyl or cyclo(lower)alkyl; R.sup.3 is lower alkyl or cyclo(lower)alkyl; R.sup.4 and R.sup.5 are each hydrogen, lower alkyl, lower alkoxy, halogen-substituted lower alkyl, lower alkyl-substituted silyl, halogen or nitro; A represents an unsaturated hydrocarbon group, a halogen-substituted unsaturated hydrocarbon group, a phenyl group or a heterocyclic group, among which the phenyl group and the heterocyclic group may be optionally substituted with not more than three substituents; and Z is --CH.sub.2 --, --CH(OH)--, --CO--, --O--, --S--, --NR-- (R being hydrogen or lower alkyl), --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, ##STR2## --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 SO--, --OCH.sub.2 --, --SCH.sub.2 -- or --SOCH.sub.2 --.
    Type: Grant
    Filed: October 8, 1993
    Date of Patent: December 6, 1994
    Assignee: Shionogi Seiyaku Kabushiki Kaisha
    Inventors: Yoshio Hayase, Takahiro Kataoka, Hideyuki Takenaka, Mitsuhiro Ichinari, Michio Masuko, Toshio Takahashi, Norihiko Tanimoto
  • Patent number: 5360454
    Abstract: Abstract of the Disclosure: A process for tanning leather comprises using for this purpose compounds of the general formula I ##STR1## where m is 0 or 1, and the radicalsR are independently of each other C.sub.1 -C.sub.18 -alkyl, which may be substituted by hydroxyl or carboxyl and/or interrupted by oxygen atoms, or else one of the radicals R is a radical of the formula ##STR2## where R.sup.1 is alkylene, which may be substituted by hydroxyl and/or interrupted by oxygen atoms.
    Type: Grant
    Filed: May 25, 1993
    Date of Patent: November 1, 1994
    Assignee: Basf Aktiengesellschaft
    Inventors: Norbert Grief, Knut Oppenlaender, Hermann Birkhofer, Brigitte Wegner, Johannes P. Dix
  • Patent number: 5354873
    Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an aromatic unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an acyl, aliphatic, cycloaliphatic, aromatic or heterocyclic group, subject to the proviso that one of R.sup.3 and R.sup.4 may be an amino or substituted amino group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a nitrogenous heterocyclic ring) are useful as near infra-red absorbers.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: October 11, 1994
    Assignee: Polaroid Corporation
    Inventors: Richard M. Allen, Peter K. Chu, John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
  • Patent number: 5352831
    Abstract: Oligomeric cyanoguanidines of formula I ##STR1## wherein, for example, R.sup.1 and R.sup.2 are each phenyl, R is 1,4-phenylene and n is an integer from 1 to 20, are suitable latent hardeners for epoxy resins. They are readily soluble in solvents suitable for the application of epoxy resins, and the cured products obtained therewith have a high glass transition temperature.
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: October 4, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Flury, Martin Roth, Sameer H. Eldin
  • Patent number: 5276159
    Abstract: A fused ring system compound is disclosed that contains an epoxide group on one side of the fused rings and an enediyne macrocyclic ring on the other side of the fused rings. The compounds have DNA-cleaving, antimicrobial and tumor growth-inhibiting properties. Chimeric compounds having the fused ring system compound as an aglycone bonded to (i) a sugar moiety as the oligosaccharide portion or (ii) a monoclonal antibody or antibody combining site portion thereof that immunoreacts with target tumor cells are also disclosed. Compositions containing a compound or a chimer are disclosed, as are methods of preparing a compound.
    Type: Grant
    Filed: May 21, 1992
    Date of Patent: January 4, 1994
    Assignee: The Scripps Research Institute
    Inventors: Adrian L. Smith, Chan-Kou Hwang, Sebastian V. Wendeborn, Kyriacos C. Nicolaou, Erwin P. Schreiner, Wilhelm Stahl, Wei-Min Dai, Peter E. Maligres, Toshio Suzuki
  • Patent number: 5270182
    Abstract: The novel compounds of formulas I and II ##STR1## have an antibiotic activity.
    Type: Grant
    Filed: May 7, 1992
    Date of Patent: December 14, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Christopher M. M. Franco, Dilip J. Upadhyay, Louis E. L. Coutinho, Bimal N. Ganguli, Jurgen Blumbach, Hans-Wolfram Fehlhaber, Herbert Kogler
  • Patent number: 5248788
    Abstract: This invention relates to a novel process for making an allenic prostanoic acid derivative in the form of a single stereoisomer, or a mixture of stereoisomers, represented by the formula (I): ##STR1## wherein R is lower alkyl, R.sup.1 is a protecting group which can be selectively removed in the presence of R.sup.2, R.sup.2 is an acid-labile, base-stable protecting group, X is --(CH.sub.2).sub.2 --, trans --CH.dbd.CH-- or --C.tbd.C--, Y is --C(R.sup.3)(OR.sup.2)CH.sub.2 --, in which --OR.sup.2 is in the .alpha. or .beta. configuration and R.sup.3 is hydrogen or methyl, Z is alkyl, or phenyl, benzyl or phenoxy each optionally substituted on the phenyl ring, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta..
    Type: Grant
    Filed: January 18, 1990
    Date of Patent: September 28, 1993
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gary F. Cooper, Colin C. Beard, David Y. Jackson, Douglas L. Wren
  • Patent number: 5227498
    Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an aliphatic, cycloaliphatic, aromatic or heterocyclic group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a cycloaliphatic or aromatic ring) are useful as near infra-red absorbers.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: July 13, 1993
    Assignee: Polaroid Corporation
    Inventors: John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
  • Patent number: 5227499
    Abstract: Squarylium compounds of the formula: ##STR1## in which: Q.sup.1 and Q.sup.2 are each a Chromophoric group having an unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens;R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group; andR.sup.3, R.sup.4 and R.sup.5 are each independently a hydrogen atom, or an aliphatic, cycloaliphatic, aromatic or heterocyclic group, or an electron-withdrawing group able to lower the electron density at the carbon atom to which it is attached, subject to the provisoes that:two of R.sup.3, R.sup.4 and R.sup.5 may form a divalent group of which a single atom is double bonded to the carbon atom to which the two groups are attached, or all three of R.sup.3, R.sup.4 and R.sup.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: July 13, 1993
    Assignee: Polaroid Corporation
    Inventors: Donald A. McGowan, Mark R. Mischke, Stephen J. Telfer
  • Patent number: 5216167
    Abstract: Phenylacetic acid benzylamides having the following general structure ##STR1## wherein the substituents are defined herein, are disclosed, which compounds are hypoglcemic agents.
    Type: Grant
    Filed: June 21, 1990
    Date of Patent: June 1, 1993
    Assignee: Dr. Karl Thomae GmbH
    Inventors: Wolfgang Grell, Rudolf Hurnaus, Gerhart Griss, deceased, Robert Sauter, Manfred Reiffen, Eckhard Rupprecht
  • Patent number: 5210235
    Abstract: A method of making compounds of the formulae: ##STR1## wherein X is ##STR2## R.sup.1 is hydrogen, methyl, C.sub.1-10 alkoxycarbonyl or arylsulfonyl when X is CH.sub.3 CH.sub.2 CHNH.sub.2 and is additionally aralkoxycarbonyl when X is NH.sub.2 ; one of R.sup.2 and R.sup.3 is hydrogen and the other is OH, NHR.sup.1 or NMeR.sup.1 where R.sup.1 is as defined above; R.sup.4 is hydrogen or C.sub.1-10 alkyl when X is CH.sub.3 CH.sub.2 CHNH.sub.2 and is additionally aralkyl when X is NH.sub.2 ; R.sup.5 is hydrogen or C.sub.1-3 alkyl when X is CH.sub.3 CH.sub.2 CHNH.sub.2 ; R.sup.5 is hydrogen when X is NH.sub.2 ; one of R6 and R7 is hydrogen and the other is methyl except when X is CH.sub.3 CH.sub.2 CHNH.sub.2 and R.sup.2 is H, in which case R.sup.6 is methyl and R.sup.7 is hydrogen. These compounds are made from erythromycin-derived fragments of the formulae: ##STR3## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are defined as before for when X is NH.sub.2 ; R.sup.5 is hydrogen or C.sub.1-3 alkyl; if R.sup.
    Type: Grant
    Filed: August 26, 1992
    Date of Patent: May 11, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Sherman T. Waddell, Timothy A. Blizzard
  • Patent number: 5185342
    Abstract: A fungicidal composition for agricultural use, which comprises a compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each hydrogen, lower alkyl or cyclo(lower)alkyl; R.sup.3 is lower alkyl or cyclo(lower)alkyl; R.sup.4 and R.sup.5 are each hydrogen, lower alkyl, lower alkoxy, halogen-substituted lower alkyl, lower alkyl-substituted silyl, halogen or nitro; A represents an unsaturated hydrocarbon group, a halogen-substituted unsaturated hydrocarbon group, a phenyl group or a heterocyclic group, among which the phenyl group and the heterocyclic group may be optionally substituted with not more than three substituents; and Z is --CH.sub.2 --, --CH(OH)--, --CO--, --O--, --S--, --NR-- (R being hydrogen or lower alkyl), --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 SO--, --OCH.sub.2 --, --SCH.sub.2 -- or --SOCH.sub.2 --.
    Type: Grant
    Filed: May 16, 1990
    Date of Patent: February 9, 1993
    Assignee: Shionogi Seiyaku Kabushiki Kaisha
    Inventors: Yoshio Hayase, Takahiro Kataoka, Hideyuki Takenaka, Mitsuhiro Ichinari, Michio Masuko, Toshio Takahashi, Norihiko Tanimoto