Spiro Patents (Class 548/407)
  • Patent number: 5171742
    Abstract: Avermectin analogs are disclosed wherein the 6,6-spiroketal ring system has been reduced in size to a 6,5-spiroketal ring system by the deletion of the 25-position carbon atom and the 25-alkyl substituent and which has a 23-acyl cycloalkyl, phenyl or substituted hydroxymethyl substituent. This is accomplished by opening the outer spiroketal ring with the elimination of ring carbon atoms 23, 24 and 25 and the alkyl substituent at the 25-position and incorporation a new component, reclosing the spiroketal to a 5-membered ring with a 23-acyl substituent and new substituents at the 24-position. The compounds are used as anti-parasitic insecticidal and anti-helmintic agents in humans and animals and compositions containing such compounds as the active ingredient thereof are also disclosed.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: December 15, 1992
    Assignee: Merck & Co., Inc.
    Inventor: Peter T. Meinke
  • Patent number: 5166350
    Abstract: A process for the preparation of a fluoran compound of the formula ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.4 are each independently hydrogen, halogen, lower alkyl or lower alkoxy,R.sub.3 is hydrogen, halogen, lower alkyl, lower alkoxy or --NX.sub.3 X.sub.4, or (R.sub.1 and R.sub.2) or (R.sub.3 and R.sub.4) each pair together with the carbon atoms to which they are attached, form a fused benzene nucleus,X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are each independently hydrogen, alkyl containing not more than 12 carbon atoms which is unsubstituted or substituted by cyano, halogen, hydroxy, tetrahydrofuryl or lower alkoxy, or are cycloalkyl, aryl or aralkyl or (X.sub.1 and X.sub.2) or (X.sub.3 and X.sub.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: November 24, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Davor Bedekovic, Jerry L. Pool, Brian J. Williams, Robert Garner, John B. Henshall
  • Patent number: 5162550
    Abstract: Bisphthalide lactones of formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of one another hydrogen, alkyl of at most 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxy, cyano, tetrahydrofuryl or lower alkoxy; or are acyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 10 carbon atoms or unsubstituted aralkyl or aryl, or aralkyl or aryl each substituted by halogen, cyano, nitro, trifluormethyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, --NX'X"-- or 4--NX'X--"phenylamino, wherein X' and X" are each independently of the other hydrogen, lower alkyl, cyclohexyl, benzyl or phenyl, or the pairs of substituents --NR.sub.1 R.sub.2 and --NR.sub.3 R.sub.4 are each a 5- or 6-membered, preferably saturated, heterocyclic radical, V.sub.1 and V.sub.2 are hydrogen, halogen, lower alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.
    Type: Grant
    Filed: August 24, 1990
    Date of Patent: November 10, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Zink, Ian J. Fletcher
  • Patent number: 5130058
    Abstract: A photochromic compound represented by the following general formula [I] ##STR1## wherein ##STR2## represents a divalent aromatic hydrocarbon group or a divalent heterocyclic group each of which may have a substituent,R.sub.1 represents a monovalent hydrocarbon group or a monovalent heterocyclic group each of which may have a substituent, ##STR3## represents a norbornylidene or adamantylidene group which may have a substituent,X represents an oxygen atom or a group of the formula >N--R.sub.3 in which R.sub.3 represents a hydrogen atom or a hydrocarbon group which may have a substituent, andR.sub.2 represents a monovalent hydrocarbon group which may have a substituent.Also provided are a process for production of the photochromic compound, a composition containing the photochromic compound, and the use of the photochromic compound. The colored form of this photochromic compound has excellent thermal stability.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: July 14, 1992
    Assignee: Tokuyama Soda Kabushiki Kaisha
    Inventors: Takashi Tanaka, Kenji Tanaka, Satoshi Imura, Yasuji Kida
  • Patent number: 5126460
    Abstract: A process for the preparation of a pure (3S,4R)-isomer of a compound of formula (A): ##STR1## wherein the substituents are herein defined in which the pyrrolidonyl or piperidonyl ring is formed by cyclizing an appropriate precursor dihydrobenzopyranol compound that has already been resolved to the (3S,4R)-configuration, or a mixture in which the (3S,4R)-configuration predominates with respect to the (3S,4R)-configuration.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: June 30, 1992
    Assignee: Beecham Group p.l.c.
    Inventor: Erol A. Faruk
  • Patent number: 5118702
    Abstract: Fungicidal and microbicidal substituted 1-aminomethyl-3-aryl-4-cyano-pyrroles of the formula ##STR1## in which Ar represents optionally substituted phenyl,R.sup.1 represents optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl or in each case optionally substituted aralkyl or aryl andR.sup.2 represents alkyl or in each case optionally substituted cycloalkylalkyl, aralkyl, cycloalkyl or aryl,and their acid addition salts.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: June 2, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Detlef Wollweber, Wolfgang Kramer, Wilhelm Brandes, Stefan Dutzmann, Wilfried Paulus
  • Patent number: 5116968
    Abstract: Compounds of formula (1) ##STR1## wherein R represents a sugar residue or an acylated derivative thereof;R.sup.1 represents a methyl, ethyl or isopropyl group;Y.sup.1 is --CH.sub.2, Y.sup.2 is --CH-- and X represents ##STR2## [wherein R.sup.2 represents a hydrogen atom or a group OR.sup.6 (where OR.sup.6 is a hydroxyl group or a substituted hydroxyl group having up to 25 carbon atoms) and R.sup.3 represents a hydrogen atom, or R.sup.2 and R.sup.3 together with the carbon atom to which they are attached represent >C.dbd.0, >C.dbd.CH.sub.2 or >C.dbd.NOR.sup.7 (where R.sup.7 represents a hydrogen atom, a C.sub.1-8 alkyl group or a C.sub.3-8 alkenyl group) and the group >C.dbd.NOR.sup.7 is in the E configuration] or --Y.sup.1 --X--Y.sup.2 -- represents --CH.dbd.CH--CH-- or --CH.sub.2 --CH.dbd.C--; andR.sup.4 represents a group OR.sup.6 as defined above and R.sup.5 represents a hydrogen atom, or R.sup.4 and R.sup.5 together with the carbon atom to which the are attached represent >C.dbd.0 or >C.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: May 26, 1992
    Assignee: American Cyanamid Company
    Inventors: Gordon C. Lawrence, Michael J. Dawson, David Noble, Michael V. J. Ramsay, Richard Bell, Derek R. Sutherland, Edward P. Tiley
  • Patent number: 5108992
    Abstract: Compounds of formula (1) ##STR1## and their salts, wherein R.sup.1 is a methyl, ethyl or isopropyl group each substituted by a hydroxyl group or R.sup.1 is a group --(CH.sub.2).sub.n R7 or a group --CH(CH.sub.3)R.sup.7 (where n is zero or 1 and R.sup.7 l is CHO or CO.sub.2 H);Y.sup.1 is --CH.sub.2 --, Y.sup.2 is --CH-- and X represents ##STR2## [where R.sup.2 is a hydrogen atom or a group OR.sup.8 is a hydroxyl group or a substituted hydroxyl group having up to 25 carbon atoms) and R.sup.3 is a hydrogen atom, or R.sup.2 and R.sup.3 together with the carbon atom to which they are attached represent >.dbd.O, >C.dbd.CH.sub.2 or >C.dbd.NOR.sup.9 (where R.sup.9 is a hydrogen atom or a C.sub.1-8 alkyl or C.sub.3-8 alkenyl group) and the group >C.dbd.NOR.sup.9 is in the E configuration] or --Y.sup.1 --X--Y.sup.2 -- represents --CH.dbd.CH--CH-- or --CH.sub.2 --CH.dbd.C--;R.sup.4 is a group OR.sup.8 as defined above and R.sup.5 is a hydrogen atom, or R.sup.4 and R.sup.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: April 28, 1992
    Assignee: American Cyanamid Company
    Inventors: Gordon C. Lawrence, Michael J. Dawson, David Noble, Richard A. Fletton, Stephen J. Lane
  • Patent number: 5097045
    Abstract: An improved process for the preparation of trans-6-[2-(substituted-pyrrol-1-yl)alkyl]pyran-2-ones by a novel synthesis is described where 1,6-heptadien-4-ol is converted in eight operations to the desired products, as well as an improved process for the preparation of (2R-trans) and trans-(.+-.)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetra hydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]1H-pyrrole-3-carboxamide by a novel synthesis where 4-methyl-3-oxo-N-phenylpentanamide is converted in eight operations to the desired product or alternatively 4-fluoro-.alpha.-[2-methyl-1-oxopropyl]-.gamma.-oxo-N,.beta.-diphenylbenze nebutaneamide is converted in one step to the desired product, and additionally, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahy dro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide from (R)-4-cyano-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]butanoic acid, as well as other valuable intermediates used in the processes.
    Type: Grant
    Filed: October 9, 1990
    Date of Patent: March 17, 1992
    Assignee: Warner-Lambert Company
    Inventors: Donald E. Butler, Carl F. Deering, Alan Millar, Thomas N. Nanninga, Bruce D. Roth
  • Patent number: 5068245
    Abstract: N-Substituted 3-arylpyrrolidine derivatives of the formula ##STR1## where R.sup.1 is 2,2-dimethylpropyl, 3,3-dimethylbutyl, 4,4-dimethylpentyl, 2,4,4-trimethylpentyl, 6-methylhept-2-yl, 3,5,5-trimethylhexyl, 6,10-dimethylundec-2-yl, 3-methylcyclohexyl, 3,3-dimethylcyclohexyl, 3,3,5-trimethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-methylcyclohexyl, 4-ethylcyclohexyl, 4-propylcyclohexyl, 4-isopropylcyclohexyl, 4-tert.-butylcyclohexyl, trans-4-tert.-butylcyclohexyl, 4(2-methylbut-2-yl)cyclohexyl, 4(2,4,4-trimethylpent-2-yl)-cyclohexyl, cyclododecanyl, C.sub.3 -C.sub.9 -trialkylsilyl-substituted C.sub.4 -C.sub.12 -cycloalkyl, 4-hydroxycyclohexyl, 4-hydroxy-3-methylcyclohexyl, 4-hydroxy-3,5-dimethylcyclohexyl, 4-hydroxy-3,3-dimethylcyclohexyl, 4-hydroxy-3,3,5-trimethylcyclohexyl, unsubstituted or hydroxy-, C.sub.1 -C.sub.9 -alkyl-, C.sub.1 -C.sub.5 -alkoxy- or C.sub.3 -C.sub.9 -trialkylsilyl-substituted C.sub.5 -C.sub.12 -cycloalkenyl,R.sup.1 is further bicycloalkyl,R.sup.1 is further 4-tert.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: November 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Zipplies, Hubert Sauter, Franz Roehl, Walter Himmele, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 5068246
    Abstract: 3-Alkyl-4-arylpyrrolidine derivatives of the formula ##STR1## where R.sup.1 is alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkyl-cycloalkyl, cycloalkyl-alkyl, alkyl-cycloalkyl-alkyl, cycloalkenyl-alkyl, alkyl-cycloalkenyl, bicycloalkyl, bicycloalkylalkyl, alkyl-bicycloalkyl, heterocycloalkyl, heterocycloalkylmethyl, aryl, arylalkyl, alkylary, alkyl-aryl-alkyl,R.sup.2 is alkyl, alkoxy,R.sup.3 is alkylR.sup.4 is alkyl, alkenyl, alkynyl and phenylalkyl,X.sup.- is a plant-tolerated anion, andn is 0 or 1,their plant-tolerated salts, and fungicides containing these compounds.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: November 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Zipplies, Hubert Sauter, Walter Himmele, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 5066814
    Abstract: 2-Dicarboximidefluorane or 3-dicarboximidefluorane compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each hydrogen, halogen, lower alkyl or lower alkoxy, one of Z.sub.1 and Z.sub.2 is the dicarboximide group ##STR2## and the other is hydrogen, halogen, lower alkyl or lower alkoxy, W is a radical of a dicarboxylic acid containing at least 2 carbon atoms, X.sub.1 and X.sub.2 are hydrogen, alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano, tetrahydrofuryl or lower alkoxy, cycloalkyl, or benzyl or phenyl each of which is unsubstituted or substituted by halogen, cyano, nitro, lower alkyl, lower alkoxy, lower alkoxycarbonyl, --NX'X" or -4-NX'X"-phenylamino in which X' and X" independently of one another are hydrogen, lower alkyl, cyclohexyl, benzyl or phenyl, or X.sub.1 and X.sub.
    Type: Grant
    Filed: February 23, 1990
    Date of Patent: November 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Zink
  • Patent number: 5066490
    Abstract: Crosslinking reagents for amino group-containing compounds are provided, which crosslinkers can be cleaved under mildly acidic conditions. The crosslinkers can be used to crosslink biologically active substances to be delivered to the cells, wherein the crosslinker will be cleaved in the mildly acidic conditions within the cell.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: November 19, 1991
    Assignee: The United States of America as represented by the Secretary of the Department of Health & Human Services
    Inventors: David M. Neville, Jr., Kasturi Srinivasachar
  • Patent number: 5061813
    Abstract: Novel compounds are disclosed having the formula ##STR1## and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are as defined herein. These compounds are useful, for example, as cardiovascular agents and especially as anti-ischemic agents.
    Type: Grant
    Filed: April 2, 1990
    Date of Patent: October 29, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Karnail Atwal
  • Patent number: 5043347
    Abstract: A compound selected from the group consisting of enantiomers and diastereoisomer forms and mixtures thereof of the formula ##STR1##
    Type: Grant
    Filed: November 17, 1989
    Date of Patent: August 27, 1991
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Odile Le Martret, Francoise Delevallee, Michel Fortin
  • Patent number: 5028711
    Abstract: Benzopyran derivatives of the general formula I ##STR1## are disclosed. The compounds are therapeutic active compounds.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: July 2, 1991
    Assignee: Beiersdorf Aktiengesellschaft
    Inventors: Wolfgang Stenzel, Theo Schotten, Ben Armah
  • Patent number: 5021423
    Abstract: Mitomycin derivatives having the formula ##STR1## wherein X is acyl, lower alkyl, alkoxycarbonyl aryloxycarbonyl or aralkoxycarbonyl;Y is hydrogen or methyl;Z is hydrogen, methyl, acyl or allyloxycarbonyl;one of R.sub.1 and R.sub.2 represents carbamoyloxymethyl and the other represents hydrogen, or R.sub.1 and R.sub.2 together represent methylene, show antibacterial and antitumor activities.
    Type: Grant
    Filed: May 26, 1989
    Date of Patent: June 4, 1991
    Assignee: Kyowa Hakko Kogyo Kabushiki Kaisha
    Inventors: Yutaka Kanda, Hitoshi Arai, Masaji Kasai, Makoto Morimoto
  • Patent number: 5019588
    Abstract: Novel 1,2-cyclohexylaminoaryl amides useful as analgesic agents having very high kappa-opioid affinity and selectivity and potency and useful as analgesics, diuretics, antiinflammatory and psychotherapeutic agents are disclosed. Methods for making the compounds and pharmaceutical compositions containing them are also disclosed.
    Type: Grant
    Filed: October 10, 1989
    Date of Patent: May 28, 1991
    Assignee: Warner-Lambert Company
    Inventors: David C. Horwell, David C. Rees
  • Patent number: 5013827
    Abstract: Triggerable dioxetanes with a fluorescent molecule containing group bonded or tethered in the dioxetane so as to produce fluorescence from the group are described. The compounds are useful in immunoassays and in probes using enzymes or other chemicals for triggering the dioxetanes to produce light from the fluorescent molecule in the group as a signal.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: May 7, 1991
    Assignee: Board of Governors of Wayne State University
    Inventor: Arthur P. Schaap
  • Patent number: 5001145
    Abstract: Compounds are described of formula (1) ##STR1## and salts thereof wherein R.sup.1 is a methyl, ethyl or isopropyl group;R.sup.2 represents a hydrogen atom or a group OR.sup.4 (where OR.sup.4 is a hydroxyl group or a substituted hydroxyl group having up to 25 carbon atoms) and R.sup.3 represents a hydrogen atom, or R.sup.2 and R.sup.3 together with the carbon atom to which they are attached represent >C.dbd.CH.sub.2, >C.dbd.O or >C.dbd.NOR.sup.5 (where R.sup.5 is a hydrogen atom or a C.sub.1-8 alkyl group and the group >C.dbd.NOR.sup.5 is in the E configuration).These compounds may be used for controlling insect, acarine, nematode or other pests.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: March 19, 1991
    Assignee: American Cyanamid Company
    Inventors: Michael V. J. Ramsay, Derek N. Evans, Derek R. Sutherland, Edward P. Tiley, John B. Ward, Neil Porter, Hazel M. Noble, Richard A. Fletton, David Noble
  • Patent number: 5001128
    Abstract: Disclosed are novel 3-hydroxy-3-methylglutarylcoenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula ##STR1## and the corresponding ring-opened hydroxy acids and esters derived therefrom and pharmaceutically acceptable salts thereof.Pharmaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.
    Type: Grant
    Filed: December 15, 1989
    Date of Patent: March 19, 1991
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Kent W. Neuenschwander, Anthony C. Scotese
  • Patent number: 4987138
    Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, 1-mercapto C.sub.2-7 alkyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino or ethenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl(NOH) or --C(C.sub.1-6 alkyl)NNH.
    Type: Grant
    Filed: August 11, 1988
    Date of Patent: January 22, 1991
    Assignee: Beecham Group p.l.c.
    Inventors: Frederick Cassidy, Geoffrey Stemp
  • Patent number: 4985421
    Abstract: Fungicidal substituted dioxolanylethylamine of the formula ##STR1## in which R represents alkyl, or represents in each case optionally substituted cycloalkylalkyl, aralkyl, cycloalkyl or aryl, andR.sup.1 and R.sup.2 independently of one another each represents hydrogen, alkyl, alkenyl, alkinyl, alkoxyalkyl, dialkoxyalkyl, hydroxyalkyl, hydroxyalkoxyalkyl, alkoxycarbonylalkyl, dioxolanylalkyl, dioxanylalkyl or oxolanylalkyl, or represents in each case optionally substituted cycloalkylalkyl, cycloalkyl, aralkyl, aralkenyl or aryl, orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, represent an optionally substituted saturated heterocyclic radical, which can optionally contain further hetero atoms,and acid addition salts thereof.Intermediates wherein the amino group is an electron-withdrawing leaving group are also new.
    Type: Grant
    Filed: August 17, 1989
    Date of Patent: January 15, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Kramer, Joachim Weissmuller, Dieter Berg, Wilhelm Brandes, Stefan Dutzmann
  • Patent number: 4981976
    Abstract: Cyanatoaryl-substituted 1,6-diaza[4.4]spirodilactam having a cyanatoaryl-containing substituent on each spiro ring nitrogen atom self-cure upon application of heat to produce cured, crosslinked thermoset resins of high glass transition temperature.
    Type: Grant
    Filed: February 23, 1989
    Date of Patent: January 1, 1991
    Assignee: Shell Oil Company
    Inventor: Pen C. Wang
  • Patent number: 4973712
    Abstract: Novel 2-aralkylaminofluorans of formula ##STR1## wherein Q is --CH.sub.2 --, --CH.sub.2 --O-- or --CO--,R.sub.1, R.sub.2 and R.sub.3 are each independently of one another hydrogen, halogen, lower alkyl or lower alkoxy,X.sub.1 and X.sub.2 are each independently of the other hydrogen, alkyl which is unsubstituted or substituted by halogen, hydroxy, cyano, tetrahydrofuryl or lower alkoxy, or ar cycloalkyl or benzyl or phenyl, each unsubstituted or substituted by halogen, cyano, nitro, lower alkyl, lower alkoxy or lower alkoxycarbonyl; or--NX.sub.1 X.sub.2 is a 5- 6-membered heterocyclic radical, and wherein the benzene rings A and B are independently of the other unsubstituted or substituted by halogen, cyano, lower alkyl, lower alkoxy, lower alkylthio, lower alkoxycarbonyl or trifluoromethyl, and the ring D is unsubstituted or substituted by halogen, nitro, lower alkyl, lower alkoxy, lower alkylthio, amino, mono-lower alkylamino or di-lower alkylamino.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: November 27, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Zink
  • Patent number: 4970309
    Abstract: This invention relates to a novel method of synthesizing di- and triarylmethane dye precursor compounds possessing a thiolactone ring-closing moiety, from the corresponding lactones.
    Type: Grant
    Filed: December 7, 1989
    Date of Patent: November 13, 1990
    Assignee: Polaroid Corporation
    Inventor: Patrick F. King
  • Patent number: 4963568
    Abstract: Novel compounds which are selective dopamine agonists are useful for treating disorders characterized by abnormal dopamine levels, such as Parkinson's Disease, as well as cardiovascular disorders.
    Type: Grant
    Filed: May 31, 1989
    Date of Patent: October 16, 1990
    Assignee: Abbott Laboratories
    Inventors: Robert W. Schoenleber, John W. Kebabian, Yvonne C. Martin, Michael P. DeNinno, Richard J. Perner, David M. Stout, Chi-Nung W. Hsiao, Stanley DiDomenico, Jr., John F. DeBernardis, Fatima Z. Basha, Michael D. Meyer, Biswanath De
  • Patent number: 4963538
    Abstract: Novel HMG-CoA reductase inhibitors are useful as antihypercholesterolemic agents and are represented by structural formulae (I) or (II): ##STR1## wherein position 5 of the polyhydronaphthyl ring is singly or doubly bonded to oxygen or incorporated into a C.sub.3-7 carbocyclic ring.
    Type: Grant
    Filed: March 13, 1989
    Date of Patent: October 16, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Mark E. Duggan, George D. Hartman
  • Patent number: 4954631
    Abstract: Fluoran compounds are disclosed of formula (I) ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently represent hydrogen, halogen, lower alkoxy, C.sub.1 -C.sub.9 -alkyl, C.sub.5 or C.sub.6 -cycloalkyl, benzyl or phenyl, said benzyl or phenyl being optionally substituted by halogen, lower alkyl or lower alkoxy, and further R.sub.1 and R.sub.2 as well as R.sub.3 and R.sub.4 taken together with Ring A, may form a naphthalene ring optionally substituted by halogen, lower alkyl or lower alkoxy, R.sub.5, R.sub.6 and R.sub.7 independently represent halogen, lower alkyl or lower alkoxy, B.sub.1 and B.sub.2 independently represent hydrogen, C.sub.1 -C.sub.8 -alkyl, benzyl or phenyl, said benzyl or phenyl being optionally substituted by halogen, lower alkyl, lower alkoxy, or alkyl-substituted, X represents hydrogen atom or --NR.sub.8 R.sub.9 wherein R.sub.8 and R.sub.9 independently represent hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.5 or C.sub.
    Type: Grant
    Filed: February 2, 1989
    Date of Patent: September 4, 1990
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Takeo Obitsu, Yutaka Ohnishi, Shinji Yoshinaka, Minoru Koguchi, Mitsuhiro Yanagita, Nobuyuki Hirai
  • Patent number: 4943582
    Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: X, Y and R.sub.1 -R.sub.6 are as defined have blood pressure lowering activity and K+ channel activator activity and are useful in the treatment of hypertension.
    Type: Grant
    Filed: May 1, 1987
    Date of Patent: July 24, 1990
    Assignee: Beecham Group p.l.c.
    Inventors: John M. Evans, Geoffrey Stemp, Frederick Cassidy
  • Patent number: 4882438
    Abstract: A compound represented by the following general formula [I] ##STR1## wherein ##STR2## represents a norbornylidene group or an adamantylidene group each of which may have a substituent, andX represents an oxygen atom, the group >N-R.sub.2, the group >N-A.sub.1 -B.sub.1 --A.sub.2).sub.m (B.sub.2).sub.n R.sub.3, the group >N-A.sub.3 -A.sub.4, or the group >N-A.sub.3 -R.sub.4, provided that when ##STR3## is an adamantylidene group, X is selected from the above groups excepting the oxygen atom and the group >N-R.sub.2 ; and plastic lens containing the compound of the above formula [I].
    Type: Grant
    Filed: November 8, 1988
    Date of Patent: November 21, 1989
    Assignee: Tokuyama Soda Kabushiki Kaisha
    Inventors: Takashi Tanaka, Satoshi Imura, Yasuji Kida
  • Patent number: 4880825
    Abstract: Mitomycin derivatives having potent anti-tumor activity having the formula: ##STR1## wherein one of R.sub.1 and R.sub.2 represents carbamoyloxymethyl and the other represents hydrogen or R.sub.1 and R.sub.2 are bonded together to form methylene;X is hydrogen or halogen;Y is hydrogen or methyl;Z is hydrogen, methyl or acyl; andn is an integer of 2 or 3.
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: November 14, 1989
    Assignee: Kyowa Hakko Kogyo Kabushiki Kaisha
    Inventors: Masaji Kasai, Yutaka Kanda, Motomichi Kono, Yutaka Saito, Makoto Morimoto, Tadashi Ashizawa
  • Patent number: 4876359
    Abstract: Novel .gamma.-butyrolactone derivatives having strong ACE inhibitory activity are provided. They are represented by the following general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and mean individually a hydrogen atom or a straight-chain or branched alkyl or cycloalkyl group, or R.sup.1 and R.sup.2 are bonded together to mean an alkylene group having 2-6 carbon atoms, R.sup.3 denotes a hydrogen atom or a lower alkyl, aralkyl, amino lower alkyl or lower alkoxycarbonylamino lower alkyl group, R.sup.4 means a lower alkyl, cycloalkyl or aralkyl group, R.sup.5 means a hydrogen atom or a lower alkyl group, or R.sub.4 and R.sub.5 are bonded together to denote an alkylene group having 2-4 carbon atoms, and R.sup.6 stands for a hydrogen atom or a lower alkyl or aralkyl group; or a pharmacologically acceptable salt thereof.
    Type: Grant
    Filed: October 1, 1987
    Date of Patent: October 24, 1989
    Assignee: SS Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Hasegawa, Noriaki Shioiri, Tadashi Narita, Tatsuhiko Katori
  • Patent number: 4871719
    Abstract: Novel 13-spiro-2'-[tetrahydrofuran]-milbemycins of the formula I ##STR1## in which X represents one of the groups --CH(OR.sub.1)--, --C(.dbd.O)-- or --C(.dbd.N--OH)--;R.sub.1 represents hydrogen or a OH-protecting group;R.sub.2 represents methyl, ethyl, isopropyl or sec.-butyl or the group --C(CH.sub.3).dbd.CH--A in which A represents methyl, ethyl or isopropyl; andR.sub.3 represents hydrogen; C.sub.1 -C.sub.10 -alkyl; C.sub.1 -C.sub.10 -alkyl substituted by at least one substituent selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy C.sub.3 -C.sub.9 -alkoxyalkoxyalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.3 -alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, hydroxy, benzyloxy, C.sub.1 -C.sub.6 -acyl and C.sub.1 -C.sub.6 -acyloxy, it being possible for each of the above-mentioned radicals representing or containing an alkoxy group to be terminally substituted at a terminal alkoxy group by hydroxy, halogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: March 16, 1988
    Date of Patent: October 3, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Maienfisch
  • Patent number: 4863922
    Abstract: Aromatic sulfonamides with a saturated heterocycle fused thereto are carbonic anhydrase inhibitors useful in the treatment of elevated intraocular pressure.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: September 5, 1989
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Gerald S. Ponticello, Marcia E. Christy
  • Patent number: 4851405
    Abstract: Fungicidally effective aminomethyl heterocyclic compounds of the formula ##STR1## in which X represents oxygen or sulphur,R represents hydrogen or alkyl, or represents in each case optionally substituted cyclohexyl or phenyl andR.sup.1 and R.sup.2 independently of one another each represent hydrogen, alkyl, alkenyl, alkinyl, alkoxyalkyl, dialkoxyalkyl, hydroalkyl, hydroxyalkoxyalkyl, alkoxycarbonylalkyl, dioxolanylalkyl, dioxanylalkyl or oxolanylalkyl, or represent in each case optionally substituted cycloalkylalkyl, cycloalkyl, aralkyl, aralkenyl or aryl, orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, represent an optionally substituted saturated heterocyclic radical, which can optionally contain further hetero atoms,or acid addition salts thereof.
    Type: Grant
    Filed: February 29, 1988
    Date of Patent: July 25, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Kramer, Joachim Weissmuller, Dieter Berg, Stefan Dutzmann
  • Patent number: 4847376
    Abstract: The present invention provides a lipase substrate of the general formula: ##STR1## wherein A is an alkylene or alkenylene radical containing up to 16 carbon atoms, R and R.sub.1, which can be the same or different, each signify an alkyl, alkenyl or acyl radical containing up to 20 carbon atoms or an optionally alkyl-substituted aryl or aralkyl radical containing up to 8 carbon atoms in the alkyl moiety and wherein one of R and R.sub.1 can also be a hydrogen atom, X is the residue of an aromatic hydroxy or thiol compound, and each Y and Z, independently from each other, is --S-- or --O--, Z also --CH.sub.2 --.The present invention also provides a process and a reagent for the optical determination of lipase.
    Type: Grant
    Filed: May 1, 1986
    Date of Patent: July 11, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Ulrich Neumann, Martina Junius, Hans-Georg Batz
  • Patent number: 4831050
    Abstract: Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from the class of C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl, C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, 1-mercapto C.sub.2-7 alkyl, formyl, or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino, C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino, or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl(NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.
    Type: Grant
    Filed: October 21, 1987
    Date of Patent: May 16, 1989
    Assignee: Beecham Group p.l.c.
    Inventors: Frederick Cassidy, Erol A. Faruk
  • Patent number: 4826977
    Abstract: A series of novel photochromic spiropyrans are disclosed in which a spiro-adamantane group is introduced into the 2-position of the benzopyran or naphthopyran ring. The spiropyran compounds of the invention exhibit heliochromic properties, i.e. they color in sunlight and fade rapidly at ambient temperatures in the absence of U.V. light, making them good candidates for use in the manufacture of sunglasses. The invention includes lenses which darken in sunlight and incorporate the novel spiropyrans and a process for the preparation of the spiropyran compounds.
    Type: Grant
    Filed: May 15, 1987
    Date of Patent: May 2, 1989
    Assignee: The Plessey Company plc
    Inventors: Harry G. Heller, Stephen N. Oliver, John Whittall, Ian Tomlinson
  • Patent number: 4820840
    Abstract: An improved process for producing fluorene compounds of the following formula (II) is disclosed: ##STR1## (wherein R.sub.1, R.sub.2 and R.sub.3 are independently a hydrogen atom, an alkylamino group, a dialkylamino group, a pyrrolidino group or a piperdino group; X and Y are independently a carbon atom or a nitrogen atom; and with the proviso that R.sub.1 and R.sub.2 are not hydrogen atoms simultaneously). The process comprises reacting a lactone compound of the formula (I) (variables being defined as in formula (II) ) ##STR2## with a mixture of an aluminum halide, a carbonyl compound, and a hydroxy bearing compound.
    Type: Grant
    Filed: January 22, 1988
    Date of Patent: April 11, 1989
    Assignee: Appleton Papers Inc.
    Inventors: Seishi Ikegami, Satoshi Nakao
  • Patent number: 4795811
    Abstract: A process for converting 6-carboxy to 6-hydroxymethyl mevinolin analogs and novel intermediates formed in this process are disclosed.
    Type: Grant
    Filed: June 22, 1987
    Date of Patent: January 3, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Samuel L. Graham, Thomas H. Scholz
  • Patent number: 4794069
    Abstract: Spirobenzanthracene phthalide compounds are disclosed of the formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently represent C.sub.1 -C.sub.8 alkyl optionally substituted by C.sub.1 -C.sub.5 alkoxy; C.sub.5 or C.sub.6 cycloalkyl; or aralkyl or aryl optionally substituted by C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy, and R.sup.1 and R.sup.2, R.sup.3 and R.sup.4, and R.sup.5 and R.sup.6 taken together with the nitrogen atom to which they are attached, may form pyrrolidino, piperidino or morpholino ring, and R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently represent hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy or trifluoromethyl. The compounds are used, together with a developer, in color for materials such as pressure-sensitive copying papers, heat-sensitive recording papers and the like.
    Type: Grant
    Filed: July 14, 1987
    Date of Patent: December 27, 1988
    Assignee: Shin Nisso Kako Co., Ltd.
    Inventors: Yutaka Ohnishi, Shinji Yoshinaka, Toshiyuki Tanaka, Minoru Koguchi, Takeo Obitsu
  • Patent number: 4794190
    Abstract: Alpha-(4-maleimidophenyl)-alpha'-(4-isomaleimidophenyl) diisopropyl benzene, as a novel composition of matter. The compound, which may be used as a component of curable thermoset resins or as a unique, difunctional synthesis intermediate having non-symmetrical reactivity, may be prepared from the corresponding bis-maleamic acid by dehydrating at or below ordinary, ambient temperatures, using acetic anhydride or a similar dehydrating agent.
    Type: Grant
    Filed: January 28, 1987
    Date of Patent: December 27, 1988
    Assignee: Amoco Corporation
    Inventors: Linda A. Domeier, Elke M. Clark
  • Patent number: 4772722
    Abstract: Disclosed are nadimido-substituted cyclophosphazene derivatives and thermosets thereof. The thermosets are useful as high temperature, flame resistant matrices for composites and as metal adhesives.
    Type: Grant
    Filed: September 10, 1986
    Date of Patent: September 20, 1988
    Assignee: Hercules Incorporated
    Inventor: Alexander Lukacs, III
  • Patent number: 4737493
    Abstract: Substituted phenoxy-, 1-, and 2-naphthalenyloxy-, indenyl-, indolyl-, benzofuranyl-, and benzo[b]thiofuranylcarboxamides of 7,8-(substituted-diamino)-1-oxaspiro[4.5]decanes are useful as analgesic agents.A method of making the compounds, pharmaceutical compositions employing the compounds, and a method of alleviating pain in warm-blooded animals are also disclosed.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: April 12, 1988
    Assignee: Warner-Lambert Company
    Inventor: David C. Horwell
  • Patent number: 4719224
    Abstract: Novel optically active isomers or racemic mixtures of thiophene acetic acid derivatives of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, Y is selected from the group consisting of --OR.sub.2 and ##STR2## R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms and ##STR3## n is an integer from 2 to 5, X' and X" are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the nitrogen atom form an optionally unsaturated heterocycle of 5 to 6 ring members, R.sub.3 and R.sub.4 are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms and their non-toxic, pharmaceutically acceptable salts with acids and bases having a good analgesic and anti-inflammatory activity and inhibition of 5-lipoxygenase and cyclooxygenase, a process and intermediates for their preparation.
    Type: Grant
    Filed: March 6, 1986
    Date of Patent: January 12, 1988
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Odile Le Martret, Francoise Delevallee
  • Patent number: 4687779
    Abstract: Compounds of formula (I): ##STR1## wherein: either one of R.sub.1 and R.sub.2 is hydrogen and the other is selected from C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 alkylcarbonyloxy, C.sub.1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, C.sub.1-6 alkoxysulphinyl,C.sub.1-6 alkoxysulphonyl, C.sub.1-6 alkylcarbonylamino, C.sub.1-6 alkoxycarbonylamino, C.sub.1-6 alkyl-thiocarbonyl, C.sub.1-6 alkoxy-thiocarbonyl, C.sub.1-6 alkyl-thiocarbonyloxy, C.sub.1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety being optionally substituted by one or two C.sub.1-6 alkyl groups, or C.sub.1-6 alkylsulphinylamino, C.sub.1-6 alkylsulphonylamino C.sub.1-6 alkoxysulphinylamino or C.sub.1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C.sub.1-6 alkylcarbonyl, nitro or cyano, or --C(C.sub.1-6 alkyl)NOH or --C(C.sub.1-6 alkyl)NNH.sub.2, or one of R.sub.1 and R.sub.2 is nitro, cyano or C.
    Type: Grant
    Filed: August 29, 1984
    Date of Patent: August 18, 1987
    Assignee: Beecham Group p.l.c.
    Inventor: John M. Evans
  • Patent number: 4685783
    Abstract: A series of photochromic compounds are disclosed which have the property of undergoing a reversible color change when exposed to unfiltered sunlight and reverting to their original color in the absence of U.V. light at room temperature. These compounds have the general formula: ##STR1## represents an adamantylidene or a substituted adamantylidene group;R.sub.1 represents hydrogen, alkyl, aryl, aralkyl or a heterocyclic group,X represents oxygen or > NR.sub.2, in which R.sub.2 is hydrogen, aryl, alkyl or aralkyl and ##STR2## represents an aromatic group, an unsaturated heterocyclic group or a benzannelated heterocyclic group.The photochromic compounds of the invention are useful in the manufacture of photoreactive lenses, particularly plastic lenses.
    Type: Grant
    Filed: September 5, 1984
    Date of Patent: August 11, 1987
    Assignee: The Plessey Company P.L.C.
    Inventors: Harold H. Heller, Stephen N. Oliver, John Whittal, William Johncock, Paul J. Darcy, Clive Trundle
  • Patent number: 4659737
    Abstract: Substituted benzopyrans of the formula ##STR1## in which --A-- is a single or double bond,X is a direct bond, optionally substituted methylene, oxygen or optionally substituted --NH--, and the various other radicals can have various meanings,or pharmaceutically acceptable addition salts thereof, which possess anti-hypertensive activity.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: April 21, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Kabbe, Ulrich Niewohner, Arno Widdig, Andreas Knorr, Bernward Garthoff, Stanislav Kazda
  • Patent number: H642
    Abstract: Compounds of the formula ##STR1## wherein X is various imino or amino acids or esters are disclosed. These compounds possess angiotensin converting enzyme inhibition activity and depending upon the definition of X also possess enkephalinase inhibition activity.
    Type: Grant
    Filed: August 20, 1984
    Date of Patent: June 6, 1989
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: David Floyd, Melanie J. Loots