Plural Ring Oxygens In The Hetero Ring Patents (Class 549/221)
-
Patent number: 5679804Abstract: 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: GrantFiled: July 27, 1995Date of Patent: October 21, 1997Assignee: BASF AktiengesellschaftInventors: Klaus Ditrich, Wolfgang Krause
-
Patent number: 5656660Abstract: 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: GrantFiled: May 31, 1995Date of Patent: August 12, 1997Assignee: Arris Pharmaceutical CorporationInventors: Robert T. Lum, Heinz W. Gschwend, Barr E. Bauer, Elaine Kuo, Ken Rice
-
Patent number: 5635608Abstract: 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: GrantFiled: November 8, 1994Date of Patent: June 3, 1997Assignee: Molecular Probes, Inc.Inventors: Richard P. Haugland, Kyle R. Gee
-
Patent number: 5608045Abstract: 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: GrantFiled: July 3, 1995Date of Patent: March 4, 1997Assignee: Adir et CompagnieInventors: Guillaume de Nanteuil, Georges Remond, Tony Verbeuren
-
Patent number: 5603868Abstract: 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: GrantFiled: October 30, 1992Date of Patent: February 18, 1997Assignee: Abbott LaboratoriesInventors: Nai-Yi Wang, Roger C. Hu
-
Patent number: 5574171Abstract: 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: GrantFiled: April 24, 1995Date of Patent: November 12, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Timothy A. Ayers, Thaliyil V. Rajanbabu
-
Patent number: 5547836Abstract: 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: GrantFiled: March 15, 1993Date of Patent: August 20, 1996
-
Patent number: 5489580Abstract: 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: GrantFiled: November 5, 1992Date of Patent: February 6, 1996Assignee: University of ConnecticutInventors: Alexandros Makriyannis, Richard I. Duclos, Jr., Donna J. Fournier
-
Patent number: 5432289Abstract: 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: GrantFiled: September 9, 1994Date of Patent: July 11, 1995Assignee: Ciba-Geigy CorporationInventors: Benoit Pugin, Felix Spindler, Manfred Muller
-
Patent number: 5424303Abstract: 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: GrantFiled: February 26, 1993Date of Patent: June 13, 1995Assignee: Symphar SAInventors: Hieu T. Phan, Lan M. Nguyen, Eric Niesor, Yves Guyon-Gellin, Craig L. Bentzen
-
Patent number: 5397852Abstract: 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: GrantFiled: August 27, 1993Date of Patent: March 14, 1995
-
Patent number: 5356886Abstract: 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: GrantFiled: January 19, 1993Date of Patent: October 18, 1994Assignee: Beecham Group p.l.c.Inventors: Michael R. Harnden, Martin J. Parratt
-
Patent number: 5342966Abstract: 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: GrantFiled: May 1, 1990Date of Patent: August 30, 1994
-
Patent number: 5308819Abstract: 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: GrantFiled: July 14, 1993Date of Patent: May 3, 1994Assignee: Ciba-Geigy CorporationInventors: Benoit Pugin, Felix Spindler, Manfred Muller
-
Patent number: 5292897Abstract: 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: GrantFiled: March 27, 1992Date of Patent: March 8, 1994Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Pierre Chabardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
-
Patent number: 5278152Abstract: 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: GrantFiled: February 18, 1993Date of Patent: January 11, 1994Assignee: Hoechst AktiengesellschaftInventors: Anuschirwan Peyman, Eugen Uhlmann, Irvin Winkler, Matthias Helsberg, Christoph Meichsner
-
Patent number: 5266708Abstract: 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: GrantFiled: March 27, 1992Date of Patent: November 30, 1993Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Pierre F. Charbardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
-
Patent number: 5252751Abstract: 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: GrantFiled: January 21, 1992Date of Patent: October 12, 1993Assignee: Ciba-Geigy CorporationInventors: Benoit Pugin, Felix Spindler, Manfred Muller
-
Patent number: 5225584Abstract: 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: GrantFiled: April 3, 1991Date of Patent: July 6, 1993Assignee: Tropix, Inc.Inventors: Edwards Brooks, Juo Rhou-Rong
-
Patent number: 5220005Abstract: 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: GrantFiled: August 30, 1990Date of Patent: June 15, 1993Assignee: Tropix, Inc.Inventor: Irena Y. Bronstein
-
Patent number: 5202111Abstract: 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: GrantFiled: May 9, 1991Date of Patent: April 13, 1993Assignee: Chesebrough-Pond's USA Co., Division of Conopco, Inc.Inventors: Suree M. Spaltro, Michael P. Aronson
-
Patent number: 5171747Abstract: 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: GrantFiled: October 16, 1990Date of Patent: December 15, 1992Assignee: Delalande S.A.Inventors: Francois X. Jarreau, Vincenzo Rovei, Jean-Jacques Koenig, Alain R. Schoffs
-
Patent number: 5157027Abstract: 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: GrantFiled: May 13, 1991Date of Patent: October 20, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Scott A. Biller, David R. Magnin
-
Patent number: 5145972Abstract: 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: GrantFiled: December 3, 1990Date of Patent: September 8, 1992Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Pierre Chabardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
-
Patent number: 5120864Abstract: 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: GrantFiled: December 3, 1990Date of Patent: June 9, 1992Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Pierre F. Charbardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
-
Patent number: 5112960Abstract: 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: GrantFiled: August 30, 1990Date of Patent: May 12, 1992
-
Patent number: 5070139Abstract: 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: GrantFiled: April 27, 1990Date of Patent: December 3, 1991Assignee: J. Uriach & Cia. S.A.Inventors: Javier Bartroli, Manuel Anquita, Elena Carceller
-
Patent number: 5013827Abstract: 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: GrantFiled: November 13, 1989Date of Patent: May 7, 1991Assignee: Board of Governors of Wayne State UniversityInventor: Arthur P. Schaap
-
Patent number: 4999437Abstract: 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: GrantFiled: March 1, 1990Date of Patent: March 12, 1991Assignee: BASF AktiengesellschaftInventors: Walter Dobler, Joachim Paust, Roland Betz
-
Patent number: 4983779Abstract: 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: GrantFiled: December 14, 1989Date of Patent: January 8, 1991Assignee: The Board of Governors of Wayne State UniversityInventor: Arthur P. Schaap
-
Patent number: 4956477Abstract: 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: GrantFiled: September 22, 1989Date of Patent: September 11, 1990
-
Patent number: 4952707Abstract: 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: GrantFiled: June 30, 1988Date of Patent: August 28, 1990
-
Patent number: 4940706Abstract: 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: GrantFiled: October 13, 1988Date of Patent: July 10, 1990Assignee: J. Uriach & Cia, S.A.Inventors: Javier Bartroli, Manuel Anquita, Elena Carceller
-
Patent number: 4933475Abstract: 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: GrantFiled: February 28, 1989Date of Patent: June 12, 1990Assignee: Pfizer, Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
-
Patent number: 4931569Abstract: 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: GrantFiled: September 14, 1988Date of Patent: June 5, 1990
-
Patent number: 4853476Abstract: 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: GrantFiled: September 24, 1987Date of Patent: August 1, 1989Assignee: Schering CorporationInventors: Konstaninos S. Petrakis, Joel G. Berger, Elijah H. Gold
-
Patent number: 4837340Abstract: Compounds related to phospholipids and a method for their preparation are sclosed.Type: GrantFiled: February 19, 1988Date of Patent: June 6, 1989Assignee: Max-Planck-Gesellschaft Zur Foederung Der Wissenschaften E. V.Inventor: Hansjorg Eibl
-
Patent number: 4786740Abstract: 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: GrantFiled: November 24, 1986Date of Patent: November 22, 1988Assignee: Stauffer Chemical Co.Inventors: Stanley B. Mirviss, Claudia H. Elkins, Sandra L. Urquhart
-
Patent number: 4777163Abstract: 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: GrantFiled: July 24, 1987Date of Patent: October 11, 1988Assignee: Boehringer Mannheim GmbHInventors: Elmar Bosies, Rudi Gall
-
Patent number: 4739079Abstract: 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: GrantFiled: March 27, 1986Date of Patent: April 19, 1988Assignee: Pfizer Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
-
Patent number: 4667027Abstract: 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: GrantFiled: December 14, 1984Date of Patent: May 19, 1987Assignee: Takeda Chemical Industries, Ltd.Inventors: Setsuo Harada, Yukimasa Nozaki, Hideo Ono
-
Patent number: 4617295Abstract: 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: GrantFiled: October 3, 1985Date of Patent: October 14, 1986Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
-
Patent number: 4615824Abstract: 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: GrantFiled: November 28, 1984Date of Patent: October 7, 1986Assignee: VEB Werk fuer Fernsehelektronik im VEB Kombinat MikroelektronikInventors: Dietrich Demus, Horst Zaschke, Gerhard Pelzl, Carsten Tschierske
-
Patent number: 4582913Abstract: 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: GrantFiled: June 11, 1984Date of Patent: April 15, 1986Assignee: Eastman Kodak CompanyInventor: Robert J. Clemens
-
Patent number: 4567168Abstract: 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: GrantFiled: January 28, 1982Date of Patent: January 28, 1986Assignee: Bayer AktiengesellschaftInventors: Bernd-Wieland Kruger, Hans-Jochem Riebel, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel
-
Patent number: 4514392Abstract: 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: GrantFiled: June 30, 1983Date of Patent: April 30, 1985Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
-
Patent number: 4483705Abstract: 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: GrantFiled: March 28, 1983Date of Patent: November 20, 1984Assignee: Monsanto Co.Inventor: William R. Purdum
-
Patent number: 4450280Abstract: Phosphorus-containing polyether polyols are prepared by reacting phosphorus-containing acids with tertiary alkyl glycidyl ether and subsequently dealkylating the tertiary alkyl functionality.Type: GrantFiled: March 4, 1982Date of Patent: May 22, 1984Assignee: The Dow Chemical CompanyInventors: Chester E. Pawloski, Sally P. Ginter
-
Patent number: 4448773Abstract: 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: GrantFiled: April 22, 1982Date of Patent: May 15, 1984Assignee: Ciba-Geigy CorporationInventors: Peter Riebli, Hanspeter Fischer, Rudolph C. Thummel, Adolf Hubele
-
Patent number: 4416832Abstract: 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: GrantFiled: January 28, 1982Date of Patent: November 22, 1983Assignee: Bayer AktiengesellschaftInventors: Bernd-Wieland Kruger, Hans-Jochem Riebel, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel