Plural Ring Oxygens In The Hetero Ring Patents (Class 549/221)
  • Patent number: 5679804
    Abstract: Phosphonic esters I ##STR1## (A is an aromatic radical or an .alpha., .beta.-olefinically unsaturated group and R.sup.1 is C.sub.1 -C.sub.4 -alkyl or phenyl) are prepared by subjecting a phosphite II ##STR2## to a rearrangement reaction in the presence of a catalytic amount of a halide ion-donating compound to give I. The compounds I are used as intermediates for organic syntheses, in particular for the synthesis of polyenes.
    Type: Grant
    Filed: July 27, 1995
    Date of Patent: October 21, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ditrich, Wolfgang Krause
  • Patent number: 5656660
    Abstract: The present invention describes compounds, methods and compositions effective to treat mast cell mediated inflammatory conditions, such as conjunctivitis, asthma and allergic rhinitis. The compounds of the invention comprise novel mono- and di-aminomethylbenzyl, aminobenzyl, guanidylbenzyl and benzyl tryptase inhibitors. The compositions for treating mast cell mediated inflammatory conditions include oral, inhalant and topical preparations as well as devices comprising such preparations.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: August 12, 1997
    Assignee: Arris Pharmaceutical Corporation
    Inventors: Robert T. Lum, Heinz W. Gschwend, Barr E. Bauer, Elaine Kuo, Ken Rice
  • Patent number: 5635608
    Abstract: The invention relates to caged compounds for the study of biological processes, where the caged compound has a photoremoveable .alpha.-carboxy-substituted o-nitrobenzyl group. Covalent attachment of the substituted o-nitrobenzyl to a parent compound yields a caged compound with biological and/or physical properties that are significantly altered from the original properties of the parent compound. Illumination of the caged compounds to cleave the photoremoveable group yields the parent compound with its original properties restored.
    Type: Grant
    Filed: November 8, 1994
    Date of Patent: June 3, 1997
    Assignee: Molecular Probes, Inc.
    Inventors: Richard P. Haugland, Kyle R. Gee
  • Patent number: 5608045
    Abstract: Compound of formula (I): ##STR1## in which: R.sub.1 represents a hydroxyl, alkoxy or amino (unsubstituted or substituted) group,R.sub.2 represents an unsubstituted or substituted alkyl group,X.sub.1 represents --NH--,X.sub.2 represents --O--,R.sub.3 represents a hydrogen atom or an alkyl or phenyl group,R.sub.4 represents an alkyl group which is always substituted with one or more hydroxyl, benzyloxy, benzyloxycarbonylamino, amino, mono- or dialkylamino, acetoxy or 2,2-dimethyl-1,3-dioxolan-4-yl groups, such groups being identical or different,R.sub.5 represents a 3-indolylmethyl, naphthylmethyl, alkyl, phenyl or benzyl group, its isomers as well as its addition salts with a pharmaceutically acceptable acid or base, and medicinal products containing the same are useful as endothelin convertase inhibitor.
    Type: Grant
    Filed: July 3, 1995
    Date of Patent: March 4, 1997
    Assignee: Adir et Compagnie
    Inventors: Guillaume de Nanteuil, Georges Remond, Tony Verbeuren
  • Patent number: 5603868
    Abstract: Chemiluminescent electron-rich aryl-substituted 1,2-dioxetane compounds are disclosed in which the aryl group is poly-substituted with suitable electron-donating groups such that the light-emitting pattern of the molecule results in a very high luminescent count, thus providing for a sensitive and precise assay for haptens, analytes, polynucleotides and the like. These substituted aryl-containing 1,2-dioxetane compounds can be used as direct labels in an immunoassay or when derivatized with an appropriate leaving group, can be used as a substrate for a enzyme immunoassay. The unusual chemiluminescence of the compounds allows the timing of the luminescent reaction to be exactly controlled.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: February 18, 1997
    Assignee: Abbott Laboratories
    Inventors: Nai-Yi Wang, Roger C. Hu
  • Patent number: 5574171
    Abstract: Enantioselective hydroformylation of vinyl compounds using a catalyst composition of a chiral carbohydrate phosphorous ligand with a Rh, Pt, Co or Ir metal, to produce chiral 2-substituted propanals, wherein the phosphorous of the ligand is substituted with electron withdrawing groups.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: November 12, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Timothy A. Ayers, Thaliyil V. Rajanbabu
  • Patent number: 5547836
    Abstract: Chemiluminescent bioassays for the presence or concentration of an analyte in a sample use 1,2-dioxetanes as substrates for the enzyme of an enzyme complex that bind to the analyte. The chemiluminescence obtained from the decomposition of the dioxetane triggered by the enzyme through the formation of the corresponding 1,2-dioxetane oxyanion of the enzyme complex is enhanced by the addition of TBQ as an enhancement agent. Other polymeric quaternary onium salts can be used as enhancement agents in conjunction with enhancement additives which improve the ability of the enhancement agent to form hydrophobic regions in the aqueous sample, in which regions the 1,2-dioxetane oxyanion and its chemiluminescent decomposition products can be sequestered. A kit for performing such assays is also provided.
    Type: Grant
    Filed: March 15, 1993
    Date of Patent: August 20, 1996
  • Patent number: 5489580
    Abstract: Novel compounds and use therefor in treating neoplastic and immune system disorders are disclosed. The compound of the present invention comprises a substituted lysophospholipid, which includes a C12 to C20 alkyl ether, a C12 to C20 thioether, or a substituted C3 to C6 heterocycle containing at least two ring heteroatoms, selected from the group consisting of nitrogen, oxygen, sulfur and combinations thereof; and also includes a choline group or a C4 to C7 heterocycle containing heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur and combinations thereof.The method for treating neoplastic or immune system disorders includes administering an effective dose of a compound of the present invention in a therapeutic manner. Effective doses of these compounds result in cytotoxic effects upon various leukemic cell lines.The compounds of this invention have the advantage that these compounds possess antineoplastic and immunomodulatory characteristics.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: February 6, 1996
    Assignee: University of Connecticut
    Inventors: Alexandros Makriyannis, Richard I. Duclos, Jr., Donna J. Fournier
  • Patent number: 5432289
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 denotes identical or different radicals and is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 of a group (R.sub.1).sub.2 P are o,o'-diphenylene, R.sub.2 is hydrogen, linear or branched C.sub.1 -C.sub.12 alkyl, phenyl or benzyl, R.sub.3 is C.sub.1 -C.sub.12 alkylene, R.sub.4 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.5 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds. These materials are heterogeneous and separable catalysts for the asymmetrical hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: July 11, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Felix Spindler, Manfred Muller
  • Patent number: 5424303
    Abstract: The present invention relates to novel aminophosphonate derivatives substituted in .alpha. position by phenol groups, of formula (I): ##STR1## in which: X.sup.1, X.sup.2, X.sup.3, R.sup.1, R.sup.2, A, B, Z and n are defined in claim 1, as well as their preparations and the pharmaceutical compositions comprising them.
    Type: Grant
    Filed: February 26, 1993
    Date of Patent: June 13, 1995
    Assignee: Symphar SA
    Inventors: Hieu T. Phan, Lan M. Nguyen, Eric Niesor, Yves Guyon-Gellin, Craig L. Bentzen
  • Patent number: 5397852
    Abstract: Methods are disclosed for purifying chemiluminescent water-soluble 1,2-dioxetane derivatives suitable for use as reporter molecules in a variety of biological analytical systems, including enzyme-linked immunoassays, nucleic acid probe techniques, and structural determinations. The methods are based upon high pressure, medium pressure or low pressure liquid chromatography using as the stationary phase alkaline pH-stable compositions with the chromatographic characteristics of reversed-phase adsorbents, at alkaline pH values, and in the absence of acid-forming compounds or compounds with an unshared pair of electrons. Desalting of substantially pure water soluble 1,2-dioxetane derivatives may be accomplished by the same chromatographic systems or by molecular sieve chromatography systems, but in the absence of salt buffers. Under some circumstances, purification and desalting may be combined in a single chromatographic step.
    Type: Grant
    Filed: August 27, 1993
    Date of Patent: March 14, 1995
  • Patent number: 5356886
    Abstract: The present invention provides antiviral compounds of Formula (I), and pharmaceutically acceptable salts thereof: ##STR1## wherein X is --CH.sub.2 O or --CH.sub.2 ;R.sub.1 is hydroxy or amino;R.sub.2 is hydrogen or amino;R.sub.3 is hydrogen, hydroxymethyl or acyloxymethyl, wherein the acyl group of said acyloxymethyl is selected from the group consisting of C.sub.1-7 alkanoyl and benzoyl optionally substituted in the phenyl ring by one, two or three substituents selected from the group consisting of fluoro, chloro, bromo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy, wherein the alkyl moiety of said C.sub.1-4 alkyl and C.sub.1-4 alkoxy substituents is selected from the group consisting of methyl, ethyl, n- and iso-propyl, n-, sec-, iso- and tert-butyl,R.sub.4 is a group of formula: ##STR2## wherein R.sub.5 and R.sub.6 are independent selected from hydrogen, C.sub.1-6 alkyl and phenyl optionally substituted by one, two or three substituents selected from the group consisting of fluoro, chloro, bromo, C.sub.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: October 18, 1994
    Assignee: Beecham Group p.l.c.
    Inventors: Michael R. Harnden, Martin J. Parratt
  • Patent number: 5342966
    Abstract: Methods are disclosed for purifying chemiluminescent water-soluble 1,2-dioxetane derivatives suitable for use as reporter molecules in a variety of biological analytical systems, including enzyme-linked immunoassays, nucleic acid probe techniques, and structural determinations. The methods are based upon high pressure, medium pressure or low pressure liquid chromatography using as the stationary phase alkaline pH-stable compositions with the chromatographic characteristics of reversed-phase adsorbents, at alkaline pH values, and in the absence of acid-forming compounds or compounds with an unshared pair of electrons. Desalting of substantially pure water soluble 1,2-dioxetane derivatives may be accomplished by the same chromatographic systems or by molecular sieve chromatography systems, but in the absence of salt buffers. Under some circumstances, purification and desalting may be combined in a single chromatographic step.
    Type: Grant
    Filed: May 1, 1990
    Date of Patent: August 30, 1994
  • Patent number: 5308819
    Abstract: Compounds where a solid carrier material which contains diphosphine rhodium or iridium complexes fixed on the surface thereof, of which the carrier material has the formula IV or IVa: ##STR1## wherein Y denotes two monoolefin ligands or a diene ligand, M is Ir(I) or Rh(i), Z is --Cl, --Br or -I, A.crclbar. is the anion of an oxyacid or complex acid, T is a solid carrier material, r is 0, 1 or 2, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined in claim 1. These materials are heterogeneous and separable catalysts for the asymmetrical hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: May 3, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Felix Spindler, Manfred Muller
  • Patent number: 5292897
    Abstract: The present invention relates to a process for preparing halo acetals of ethylenic aldehydes by reaction of a halogen cation with enamine followed by a hydrolysis and reaction with an alcohol, a glycol or an orthoformate. These halo acetals are used as intermediate for the synthesis of vitamins A and E.It also relates to a new compound of formula (IV), ##STR1## to a process for preparing it from halo acetals of ethylenic aldehydes by reaction with triethyl phosphate, and to its use for the preparation of retinal by reaction with .beta.-ionylideneacetaldehyde.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: March 8, 1994
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre Chabardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5278152
    Abstract: The compound of the formula I ##STR1## in which R is an aldehyde group or a group which can be converted into an aldehyde, R.sup.1 and R.sup.2 are alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl, hydrogen, sodium, potassium, calcium, magnesium, aluminum, lithium, ammonium or triethylamnonium, orR.sup.1 and R.sup.2 together form a cyclic diester,R.sup.3 and R.sup.4 are alkyl, alkenyl, alkynyl, cycloalkyl, hydrogen, alkoxy or halogen, R.sup.5 and R.sup.8 are alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl, alkoxy, phenyl, cyanide, hydroxyl or hydrogen, and X, Y or Z are oxygen or sulfur, or prodrug forms of the compound of the formula I can be used for the treatment of diseases caused by viruses.The preparation of these compounds and pharmaceutical preparations containing them and their use is described.
    Type: Grant
    Filed: February 18, 1993
    Date of Patent: January 11, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Anuschirwan Peyman, Eugen Uhlmann, Irvin Winkler, Matthias Helsberg, Christoph Meichsner
  • Patent number: 5266708
    Abstract: New intermediates and processes for the preparation of vitamins A and E, which are the acetals of 5,6-dihalo-3-methyl-3-hydroxyhexanal or of 6-halo-3-hydroxy-3-methyl-5-hexenal or 3-methyl-3-hydroxy-5-hexenal, as well as processes for making the intermediates. After dehydrohalogenation and dehydration these intermediates are condensed directly with .beta.-ionone or with 2-methyl-2-heptene-6-one to synthesize vitamins A and E respectively.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: November 30, 1993
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre F. Charbardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5252751
    Abstract: Compounds of formula I ##STR1## wherein R.sub.1 denotes identical or different radicals and is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 of a group (R.sub.1).sub.2 P are o,o'-diphenylene, R.sub.2 is hydrogen, linear or branched C.sub.1 -C.sub.12 alkyl, phenyl or benzyl, R.sub.3 is C.sub.1 -C.sub.12 alkylene, R.sub.4 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.5 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds. These materials are heterogeneous and separable catalysts for the asymmetrical hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds, for example ketones and imines.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: October 12, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Benoit Pugin, Felix Spindler, Manfred Muller
  • Patent number: 5225584
    Abstract: A novel synthesis of compounds having the formula: ##STR1## wherein T is a stabilizing spiro-linked polycycloalkylidene group, R.sup.3 is a C.sub.1 -C.sub.20 alkyl, aralkyl or heteroatom containing group, Y is an aromatic fluorescent chromophore, and Z is a cleavable group which, when cleaved, induces decomposition of the dioxetane ring and emission of optically detectable light, is disclosed. A tertiary phosphorous acid alkyl ester of the formula:(R.sup.1 O).sub.3 Pwherein R.sup.1 is a lower alkyl group, is reacted with an aryl dialkyl acetal produced by reacting a corresponding aryl aldehyde with an alcohol of the formula:R.sup.3 OHwherein R.sup.3 is as defined above, to produce a 1-alkoxy-1-arylmethane phosphonate ester of the formula: ##STR2## reacting the phosphonate with base to produce a phosphonate-stabilized carbanion, reacting the carbanion with a ketone of the formula:T.dbd.
    Type: Grant
    Filed: April 3, 1991
    Date of Patent: July 6, 1993
    Assignee: Tropix, Inc.
    Inventors: Edwards Brooks, Juo Rhou-Rong
  • Patent number: 5220005
    Abstract: Dioxetane compounds reactable with an enzyme to release optically detectable eneregy are disclosed. These compounds have the formula: ##STR1## wherein T is a carboxylic acid or methoxy substituted adamantyl group bound to the ring through a spiro bond, Y is phenoxy or napthyloxy and X is methoxy, ethoxy or propoxy. Z is an enzyme cleavable group such that when cleaved by an enzyme, an electron rich moiety is left bound to the dioxetane ring.
    Type: Grant
    Filed: August 30, 1990
    Date of Patent: June 15, 1993
    Assignee: Tropix, Inc.
    Inventor: Irena Y. Bronstein
  • Patent number: 5202111
    Abstract: A composition and method for controlling tartar formation in the mouth is reported based upon phosphorylated polyhydroxy substances. These substances are formed by phosphorylation of a polyhydroxy starting compound of molecular weight no higher than 5000, have a molar substitution of at least 2 based on molecular weight of an average repeat unit in the starting polyhydroxy compound and possess phosphate ester linkages satisfying at least one criteria selected from:(a) at least one multi-substituted phosphate ester linked through an oxygen atom to a single carbon of the polyhydroxy compound; and(b) at least two monophosphate groups separated by no more than three carbon atoms.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: April 13, 1993
    Assignee: Chesebrough-Pond's USA Co., Division of Conopco, Inc.
    Inventors: Suree M. Spaltro, Michael P. Aronson
  • Patent number: 5171747
    Abstract: The derivatives of the formula: ##STR1## wherein: R.sub.1 is H or C.sub.1 -C.sub.4 alkyl;X is an oxygen atom, a methylene group or a --CH.dbd.CH-- group;n is 1 or 2 when X is an oxygen atom or a methylene group and 0 or 1 when X is a --CH.dbd.CH-- group;D is an oxygen atom or a NOR group, wherein R.dbd.H or C.sub.1 -C.sub.4 alkyl;R.sub.3 is a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group;each of R.sub.2 and R'.sub.2 independently is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl or benzyl group; andR'.sub.2 and R.sub.3 may further form together a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 -- chain,useful as drugs.
    Type: Grant
    Filed: October 16, 1990
    Date of Patent: December 15, 1992
    Assignee: Delalande S.A.
    Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
  • Patent number: 5157027
    Abstract: Compounds which are inhibitors of cholesterol biosynthesis (by inhibiting de novo squalene biosynthesis), and thus are useful as hypocholesterolemic agents and antiatherosclerotic agents are provided which have the structure ##STR1## and analogs thereof, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and are H, lower alkyl, a metal ion or a prodrug ester;R.sup.5 is H, halogen or lower alkyl;Zq is substituted alkenyl, substituted alkynyl, mixed alkenyl-alkynyl or substituted phenylalkyl or, phenylalkenyl or phenylalkynyl, or alkyl, including all stereoisomers thereof.New methods for using such compounds to inhibit cholesterol biosynthesis are also provided.
    Type: Grant
    Filed: May 13, 1991
    Date of Patent: October 20, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Scott A. Biller, David R. Magnin
  • Patent number: 5145972
    Abstract: The present invention relates to a process for preparing halo acetals of ethylenic aldehydes by reaction of a halogen cation with enamine followed by a hydrolysis and reaction with an alcohol, a glycol or an orthoformate. These halo acetals are used as intermediate for the synthesis of vitamins A and E.It also relates to a new compound of formula (IV), ##STR1## to a process for preparing it from halo acetals of ethylenic aldehydes by reaction with triethyl phosphate, and to its use for the preparation of retinal by reaction with .beta.-ionylideneacetaldehyde.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: September 8, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre Chabardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5120864
    Abstract: New intermediates and processes for the preparation of vitamins A and E, which are the acetals of 5,6-dihalo-3-methyl-3-hydroxyhexanal or of 6-halo-3-hydroxy-3-methyl-5-hexenal or 3-methyl-3-hydroxy-5-hexenal, as well as processes for making the intermediates. After dehydrohalogenation and dehydration these intermediates are condensed directly with .beta.-ionone or with 2-methyl-2-heptene-6-one to synthesize vitamins A and E respectively.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: June 9, 1992
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre F. Charbardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5112960
    Abstract: Enzymatically cleavable chemiluminescent 1,2-dioxetane compounds capable of producing light energy when decomposed, substantially stable at room temperature before a bond by which an enzymatically cleavable labile substituent thereof is intentionally cleaved, are disclosed. These compounds can be represented by the formula: ##STR1## wherein: X and X.sup.1 each represent, individually, hydrogen, a hydroxyl group, a halo substituent, an unsubstituted lower alkyl group, a hydroxy (lower) alkyl group, a halo (lower) alkyl group, a phenyl group, a halophenyl group, an alkoxyphenyl group, a hydroxyalkoxy group, a cyano group or an amide group, with at least one of X and X.sup.1 being other than hydrogen; andR.sub.1 and R.sub.2, individually or together, represent an organic substituent that does not interfere with the production of light when the dioxetane compound is enzymatically cleaved and that satisfies the valence of the dioxetane compound's 4-carbon atom, with the provisos that if R.sub.1 and R.sub.
    Type: Grant
    Filed: August 30, 1990
    Date of Patent: May 12, 1992
  • Patent number: 5070139
    Abstract: The present invention describes novel 2,4-disubstituted 1,3-dioxolanes having the formula I ##STR1## wherein R.sup.1 represents a long chain alkyl group; X is a covalent single bond, a carbonyl group, a carboxyl group, a carbamoyl group or a --O--P(.dbd.O)(O.sup.z)-- group; z is a negative charge (-) when q is zero, or z is an hydrogen atom when q is one; n is an integer from 2 to 10; R.sup.2, R.sup.3 and R.sup.4 are lower alkyl groups, or R.sup.2 R.sup.3 R.sup.4 N.sup.30 represents an aromatic cyclic ammonium group or R.sup.2 R.sup.3 R.sup.4 N.sup.+ represents a non-aromatic cyclic ammonium group in which two of the groups (R.sup.2, R.sup.3 or R.sup.4) form a non-aromatic ring together with the quaternary nitrogen atom; and A.sup.- is a pharmaceutically acceptable anion. These compounds are in vitro inhibitors of the platelet aggregation induced by the platelet activating factor (PAF) and, thus, useful for the treatment of the diseases in which this substance is involved.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: December 3, 1991
    Assignee: J. Uriach & Cia. S.A.
    Inventors: Javier Bartroli, Manuel Anquita, Elena Carceller
  • 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: 4999437
    Abstract: Ascorbic acid 2-phosphate is prepared by reacting ascorbic acid or an ascorbic acid derivative with POCl.sub.3 in the presence of a tertiary amine in a suitable aqueous solvent at from -10.degree. to 25.degree. C. while maintaining a pH of about 8-13.5 with KOH during the entire phosphorylation reaction and then isolating the ascorbic acid 2-phosphate, by a process in which an aqueous solution of a magnesium compound is added to the reaction mixture obtained in the phosphorylation, without prior treatment with an ion exchanger, until the formation of crystalline KMg PO.sub.4 is complete, the KMgPO.sub.4 which is crystallized out is separated off, the resulting filtrate is evaporated down at a pH of from 6 to 11 and/or from 0.
    Type: Grant
    Filed: March 1, 1990
    Date of Patent: March 12, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Dobler, Joachim Paust, Roland Betz
  • Patent number: 4983779
    Abstract: An improved process for the preparation of vinyl ethers by the coupling reaction of an ester of the formula ##STR1## with a carbonyl containing compound of the formula ##STR2## wherein A and R are passive organic groups and OY is a hydroxyl group or OP where P is a protecting group is described. The ester and the carbonyl containing compound are reacted in an organic solvent with a titanium salt, a metallic reducing agent and an amine base to provide the vinyl ether. The reaction is safe and produces high yields. The vinyl ethers are useful for producing dioxetanes which produce light upon triggering.
    Type: Grant
    Filed: December 14, 1989
    Date of Patent: January 8, 1991
    Assignee: The Board of Governors of Wayne State University
    Inventor: Arthur P. Schaap
  • Patent number: 4956477
    Abstract: Compounds having the formula: ##STR1## wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C.sub.1-20 alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g., m-phenylene), produced by reacting a compound having the formula: ##STR2## with an R-ylating agent (e.g., R.sub.2 SO.sub.4) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula: ##STR3## are produced by reacting a compound having the formula: ##STR4## wherein X is an electronegative leaving group (e.g., a halogen anion such as chloride ion) in the presence of a Lewis base (e.g., a trialkyl-amine) dissolved in an aprotic organic solvent (e.g., benzene or toluene). Also, compounds having the formula ##STR5## are produced by reacting a compound of the formula ##STR6## with a tetra-O-acylated-O-hexopyranoside halide, then hydrolyzing off the protective acyl groups.
    Type: Grant
    Filed: September 22, 1989
    Date of Patent: September 11, 1990
  • Patent number: 4952707
    Abstract: Chemiluminescent 1,2-dioxetane compounds are disclosed in which the molecule is stabilized at the 3-position on the dioxetane ring against decomposition prior to the molecule's coming in contact with a labile group-removing substance (e.g., an enzyme that will cleave the labile group to cause the molecule to decompose to form at least one light-emitting fluorophore) and substituted at the 4-position on the dioxetane ring with a fused polycyclic ring-containing fluorophore moiety bearing a labile ring substituent whose point of attachment to the fused polycyclic ring, in relation to this ring's point(s) of attachment to the dioxetane ring, is such that the total number of ring atoms separating these points of attachment, including the ring atoms at the points of attachment, is an odd whole number. These odd pattern substituted compounds decompose to emit light of greater intensity and of a different wavelength than that emitted by the corresponding even pattern substituted isomers.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: August 28, 1990
  • Patent number: 4940706
    Abstract: The present invention describes novel 2,4-disubstituted 1,3-dioxolanes having the formula I ##STR1## wherein R.sup.1 represents a long chain alkyl group; X is a covalent single bond, a carbonyl group, a carboxyl group, a carbamoyl group or a --O--P(.dbd.O)(O.sup.z)-- group; z is a negative charge (-) when q is zero, or z is an hydrogen atom when q is one; n is an integer from 2 to 10; R.sup.2, R.sup.3 and R.sup.4 are lower alkyl groups, or R.sup.2 R.sup.3 R.sup.4 N.sup.+ represents an aromatic cyclic ammonium group or R.sup.2 R.sup.3 R.sup.4 N.sup.+ represents a non-aromatic cyclic ammonium group in which two of the groups (R.sup.2, R.sup.3 or R.sup.4) form a non-aromatic ring together with the quaternary nitrogen atom; and A.sup.- is a pharmaceutically acceptable anion. These compounds are in vitro inhibitors of the platelet aggregation induced by the platelet activating factor (PAF) and, thus, useful for the treatment of the diseases in which this substance is involved.
    Type: Grant
    Filed: October 13, 1988
    Date of Patent: July 10, 1990
    Assignee: J. Uriach & Cia, S.A.
    Inventors: Javier Bartroli, Manuel Anquita, Elena Carceller
  • Patent number: 4933475
    Abstract: Compounds having the formula ##STR1## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.
    Type: Grant
    Filed: February 28, 1989
    Date of Patent: June 12, 1990
    Assignee: Pfizer, Inc.
    Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4931569
    Abstract: Methods are disclosed for purifying chemiluminescent water-soluble 1,2-dioxetane derivatives suitable for use as reporter molecules in a variety of biological analytical systems, including enzyme-linked immunoassays, nucleic acid probe techniques, and structural determinations. The methods are based upon high pressure, medium pressure or low pressure liquid chromatography using as the stationary phase alkaline pH-stable compositions with the chromatographic characteristics of reversed-phase adsorbents, at alkaline pH values, and in the absence of acid-forming compounds or compounds with an unshared pair of electrons. Desalting of substantially pure water soluble 1,2-dioxetane derivatives may be accomplished by the same chromatographic systems or by molecular sieve chromatography systems, but in the absence of salt buffers. Under some circumstances, purification and desalting may be combined in a single chromatographic step.
    Type: Grant
    Filed: September 14, 1988
    Date of Patent: June 5, 1990
  • Patent number: 4853476
    Abstract: Novel phosphorous containing compounds and compositions containing said compounds inhibit the actions of enkephalinases in mammals. Methods for preparing said compounds and compositions and methods for their use to elicit analgesia and treat mental disorders are described.Useful intermediates for preparing the compounds are also described.
    Type: Grant
    Filed: September 24, 1987
    Date of Patent: August 1, 1989
    Assignee: Schering Corporation
    Inventors: Konstaninos S. Petrakis, Joel G. Berger, Elijah H. Gold
  • Patent number: 4837340
    Abstract: Compounds related to phospholipids and a method for their preparation are sclosed.
    Type: Grant
    Filed: February 19, 1988
    Date of Patent: June 6, 1989
    Assignee: Max-Planck-Gesellschaft Zur Foederung Der Wissenschaften E. V.
    Inventor: Hansjorg Eibl
  • Patent number: 4786740
    Abstract: A process for purifying a reaction mixture comprising a phosphorodithioic acid ester of dichloro-para-dioxane prepared by reacting an O,O-dialkyl phosphorodithioic acid with a dichloro-para-dioxane in the presence of a catalytic amount of a Lewis acid. This process comprises washing the reaction mixture with an ammonium hydroxide solution, and preferably with an ammonium hydroxide solution containing ammonium chloride.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: November 22, 1988
    Assignee: Stauffer Chemical Co.
    Inventors: Stanley B. Mirviss, Claudia H. Elkins, Sandra L. Urquhart
  • Patent number: 4777163
    Abstract: The present invention produces alkyldiphosphonic acid derivative of the general formula: ##STR1## wherein Het is a heteroaromatic five-membered ring containing to 3 heteroatoms which can be partly hydrogenated and optionally substituted one or more times by alkyl, alkoxy, phenyl, cyclohexyl, cyclohexylmethyl, halogen or amino, and two adjacent alkyl substituents can together also form a ring, Y is a hydrogen atom or a lower alkyl radical, X is a hydrogen atom, a hydroxyl group or an amino group optionally substituted by lower alkyl and R is a hydrogen atom or a lower alkyl radical, with the proviso that Het is not a pyrazole ring; as well as the pharmacologically acceptable salts thereof.
    Type: Grant
    Filed: July 24, 1987
    Date of Patent: October 11, 1988
    Assignee: Boehringer Mannheim GmbH
    Inventors: Elmar Bosies, Rudi Gall
  • Patent number: 4739079
    Abstract: Compounds having the formula ##STR1## wherein ##STR2## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: April 19, 1988
    Assignee: Pfizer Inc.
    Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4667027
    Abstract: A compound of the formula: ##STR1## wherein R.sup.1 stands for hydrogen or formylamino, R.sup.2 is a residue of amino acid selected from the group consisting of serine and alanine, or a peptide of at least one of these amino acids, or hydrogen, R.sup.3 stands for --NH--C(.dbd.NH)--NH.sub.2 or --CH.sub.2 NH.sub.2, or its salt, which can be produced by cultivating a microorganism belonging to the genus Xanthomonas, is useful as a therapeutic agent against infectious disease caused by bacteria.
    Type: Grant
    Filed: December 14, 1984
    Date of Patent: May 19, 1987
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Setsuo Harada, Yukimasa Nozaki, Hideo Ono
  • Patent number: 4617295
    Abstract: Oxime N-alkyl-N-.alpha.-(alkylthio-phosphorothio)acyl carbamates represented the structure: ##STR1## wherein the R represents various imino radicals, Q is oxygen or sulfur and the numbered R groups represent various alkyl substituents, which exhibit superior insecticidal and miticidal activity.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: October 14, 1986
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4615824
    Abstract: A mixing component for nematic liquid-crystalline substances used in optoelectronic components for the rendition of numbers, symbols and images. The object of the invention is to reduce, in components for nematic liquid crystal substances, the threshold and operating voltages. It has been found, that the addition of one or more 1-oxa-2,6,7-trioxane-1-phospha-bicyclo-derivatives having the general formula ##STR1## wherein ##STR2## with R.sup.1 =C.sub.n H.sub.2n+1 --, C.sub.n H.sub.2n+1 O--, C.sub.n H.sub.2n+1 COO--, C.sub.n H.sub.2n+1 OCOO--, R.sup.2 +C.sub.n H.sub.2n=1 --with n=an integer from 1 to 10to nematic liquid crystal substances, considerably reduces the operating voltage.
    Type: Grant
    Filed: November 28, 1984
    Date of Patent: October 7, 1986
    Assignee: VEB Werk fuer Fernsehelektronik im VEB Kombinat Mikroelektronik
    Inventors: Dietrich Demus, Horst Zaschke, Gerhard Pelzl, Carsten Tschierske
  • Patent number: 4582913
    Abstract: Disclosed are novel 5-halo-4H-1,3-dioxin-4-ones and their preparation by treating a compound having the formula ##STR1## with X.sub.2 or SO.sub.2 X.sub.2 wherein X is Cl or Br.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: April 15, 1986
    Assignee: Eastman Kodak Company
    Inventor: Robert J. Clemens
  • Patent number: 4567168
    Abstract: A cyanohydrin phosphate of the formula ##STR1## wherein R represents a hydrogen atom or an optionally substituted radical selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, aralkenyl and aryl, or an optionally substituted heterocyclic radical,R.sup.1 and R.sup.2 are identical or different and individually represent optionally substituted radicals selected from alkyl, alkenyl, alkynyl, aryl, aralkyl, alkoxy, aryloxy, aralkoxy, alkylthio, alkenylthio, alkinylthio, arylthio, aralkylthio, alkylamino (monoalkylamino or dialkylamino), arylamino and aralkylamino, or together represent alkanediyl, alkanedioxy, aminoalkyloxy or alkanediamino, andX represents oxygen or sulphur,are obtained by the reaction of a phosphoric acid chloride of the general formula ##STR2## wherein X, R.sup.1 and R.sup.2 have the meaning given above, with an aldehyde of the general formulaR--CHO (III)wherein R has the meaning given above, in the presence of an approximately equimolar quantity of water-soluble cyanides.
    Type: Grant
    Filed: January 28, 1982
    Date of Patent: January 28, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Kruger, Hans-Jochem Riebel, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel
  • Patent number: 4514392
    Abstract: Novel, aryl N-(alkylthio-phosphorothio)acyl carbamates represented by structure: ##STR1## wherein the R groups represent various alkyl substituents, and Ar represents an aryl radical with various organic substituents, which exhibit superior insecticidal and miticidal activity.
    Type: Grant
    Filed: June 30, 1983
    Date of Patent: April 30, 1985
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4483705
    Abstract: Alkylphosphonate diesters and monoesters of N-phosphonomethylglycine are disclosed which are useful as herbicides. This invention further relates to herbicidal compositions containing such alkylphosphonate diesters and monoesters of N-phosphonomethylglycine and to herbicidal methods employing such compounds and compositions.
    Type: Grant
    Filed: March 28, 1983
    Date of Patent: November 20, 1984
    Assignee: Monsanto Co.
    Inventor: William R. Purdum
  • Patent number: 4450280
    Abstract: Phosphorus-containing polyether polyols are prepared by reacting phosphorus-containing acids with tertiary alkyl glycidyl ether and subsequently dealkylating the tertiary alkyl functionality.
    Type: Grant
    Filed: March 4, 1982
    Date of Patent: May 22, 1984
    Assignee: The Dow Chemical Company
    Inventors: Chester E. Pawloski, Sally P. Ginter
  • Patent number: 4448773
    Abstract: Compounds of the formula ##STR1## in which Ar is 2-alkyl-, -alkoxy- or -halo-methyl-phenyl or .alpha.-naphthyl, each of which is further substituted,R.sub.1 is 2-furyl, 2-tetrahydrofuryl, alkenyl, cyclopropyl, .beta.-alkoxyethyl, hydroxymethyl, triazolylmethyl, imidazolylmethyl, pyrazolylmethyl, alkylsulfinyl, alkylsulfonyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylsulfinyloxy, dialkylaminosulfinyloxy, phosphoric or thiophosphoric esters or amides, or alkylcarbonyloxy,R.sub.7 is hydrogen or optionally-substituted methyl or ethyl, andR.sub.8 is alkyl optionally substituted by alkoxy,are microbicidally, in particular fungicidally, active. Preferred compounds are those in which Ar is 2-methylphenyl, 2-methoxyphenyl, 2-chlorophenyl or .alpha.-naphthyl, each of which is further substituted by azido, and each of R.sub.7 and R.sub.8 is methyl.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: May 15, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Riebli, Hanspeter Fischer, Rudolph C. Thummel, Adolf Hubele
  • Patent number: 4416832
    Abstract: New cyanoalkylphosphoric acid ester chlorides of the general formula ##STR1## in which R represents a hydrogen atom, an optionally substituted radical selected from alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aralkenyl and aryl, or an optionally substituted heterocyclic radical,R.sup.1 represents an optionally substituted radical selected from alkyl, alkenyl, alkinyl, aryl, aralkyl, alkoxy, aryloxy, aralkoxy, alkylthio, alkenylthio, alkinylthio, arylthio, aralkylthio, alkylamino (monoalkylamino or dialkylamino), arylamino or aralkylamino and X represents oxygen or sulphurare obtained by the reaction of a phosphoric acid dichloride of the general formula ##STR2## with an aldehyde of the general formulaR--CHO (III)in the presence of an approximately equimolar quantity of a water-soluble cyanide. The compounds of the formula (I) can be used as intermediate products for the preparation of insecticides.
    Type: Grant
    Filed: January 28, 1982
    Date of Patent: November 22, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Kruger, Hans-Jochem Riebel, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel