Phosphorus Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/218)
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Patent number: 5436245Abstract: Hypotensive activity is exhibited by new phosphonate substituted amino or imino acids of the formula ##STR1## isomeric mixtures thereof and pharmaceutically acceptable salts thereof, wherein:X is an imino or amino acid of the formula ##STR2##Type: GrantFiled: November 17, 1993Date of Patent: July 25, 1995Assignee: E. R. Squibb & Sons, Inc.Inventor: Donald S. Karanewsky
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Patent number: 5407922Abstract: Compounds having GABA.sub.B -antagonistic properties, for example those of formula I ##STR1## wherein one of the radicals R.sub.1, R.sub.2 and R.sub.3 is hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical, another is hydrogen or, in the case of R.sub.1 or R.sub.2, hydroxy or, in the case of R.sub.1, halogen or, in the case of R.sub.2 together with R.sub.2 ', oxo, and the remaining radical is hydrogen, R.sub.1 ' is hydrogen or halogen, R.sub.2 ' is hydrogen, hydroxy or, together with R.sub.2, is oxo, R.sub.4 and R.sub.5 are hydrogen or R.sub.4 is an araliphatic or heteroarylaliphatic radical and R.sub.5 is hydrogen or an aliphatic radical, and R is an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, araliphatic, heteroarylaliphatic or aromatic radical having at least 2 carbon atoms or, when R.sub.1 is hydrogen or hydroxy, R.sub.2 is an aromatic radical and R.sub.1 ', R.sub.2 ' and R.sub.Type: GrantFiled: May 3, 1993Date of Patent: April 18, 1995Assignee: Ciba-Geigy CorporationInventors: Christian Marescaux, Raymond Bernasconi, Markus Schmutz, Wolfgang Frostl, Stuart J. Mickel
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Patent number: 5405976Abstract: Dyes comprising an inner salt of a compound of the formula:Q.sup.1 =Z-Q.sup.2wherein:Q.sup.1 is a 4-(benz[b]-4H-pyrylium)methylidene, 4-(benz[b]-4H-thiopyrylium)methylidene or 4-(benz[b]-4H-selenopyrylium)methylidene grouping;Z is a 1,3-(2-hydroxy-4-oxo-2-cyclobutylidene) hydroxide or 1,3-(2-hydroxy-4,5-dioxo-2-cyclopentylidene) hydroxide ring; andQ.sup.2 is a 4-(benz[b]-4H-pyran-4-ylidene)methyl, 4-(benz[b]-4H-thiopyran-4-ylidene)methyl or 4-(benz[b]-4H-selenopyran-4-ylidene)methyl grouping;wherein at least one of the groupings Q.sup.1 and Q.sup.Type: GrantFiled: September 24, 1993Date of Patent: April 11, 1995Assignee: Polaroid CorporationInventors: Stephen J. Telfer, Robert P. Short, Stephen G. Stroud, Anthony J. Puttick, Socorro Ramos, Michael J. Zuraw
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Patent number: 5405841Abstract: The invention relates to new phosphorylated aza compounds, to processes for their preparation and to their use as pesticides, in particular as soil-acting insecticides and nematicide.The new compounds have the general formula (I) ##STR1## in which R.sup.1 -R.sup.5, X and Y are defined as in the specification, with the exception of compound O-ethyl S-propyl 3-(6-chloro-3-pyridinylmethyl)-2-nitroimino-imidazolidine-1-thiophosphate.Type: GrantFiled: November 30, 1993Date of Patent: April 11, 1995Assignee: Bayer AktiengesellschaftInventors: Fritz Maurer, Jurgen Hartwig, Christoph Erdelen
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Patent number: 5386017Abstract: Novel alkenes leading to light producing 1,2-dioxetanes of the formula ##STR1## wherein ArOX is an aryl ring substituted with an X oxy group and A are passive organic groups which allow the 1,2-dioxetane to produce light when triggered by removing X. X is a chemically labile group which is removed by an activating agent. The 1,2-dioxetane compounds can be triggered to produce light at room temperatures.Type: GrantFiled: February 26, 1990Date of Patent: January 31, 1995Assignee: Board of Governors of Wayne State UniversityInventor: Arthur P. Schaap
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Patent number: 5374628Abstract: Phosphonic acid squalene synthetase inhibitors are provided which are effective in lowering serum cholesterol and have the formula ##STR1## wherein m is 0 to 3, n is 1 to 5, Y.sup.1 and Y.sup.2 are H or halogen, R.sup.2, R.sup.3 and R.sup.4 are H, metal ion, C.sub.1 to C.sub.8 alkyl, C.sub.3 to C.sub.12 alkenyl, or prodrug ester, and R.sup.1 is a substituted or unsubstituted heteroaryl group or a substituted phenyl group.Type: GrantFiled: October 18, 1993Date of Patent: December 20, 1994Assignee: E. R. Squibb & Sons, Inc.Inventor: Scott A. Biller
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Patent number: 5371248Abstract: Monoalkylated benzofuran adducts provide high temperature stable lubricant fluids having not only excellent thermal stability, but good low-temperature properties and excellent additive solubility as well.Type: GrantFiled: February 22, 1993Date of Patent: December 6, 1994Assignee: Mobil Oil CorporationInventor: Leslie R. Rudnick
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Patent number: 5354873Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an aromatic unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an acyl, aliphatic, cycloaliphatic, aromatic or heterocyclic group, subject to the proviso that one of R.sup.3 and R.sup.4 may be an amino or substituted amino group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a nitrogenous heterocyclic ring) are useful as near infra-red absorbers.Type: GrantFiled: November 20, 1992Date of Patent: October 11, 1994Assignee: Polaroid CorporationInventors: Richard M. Allen, Peter K. Chu, John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
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Patent number: 5338730Abstract: A process for preparing the (R) stereoisomer of 2,2-bis(hydroxmethyl)-tetrahydrofuran monobutyrate comprising subjecting the dibutyric ester of the 2,2-bis(hydroxymethyl)-tetrahydrofuran to enzymatic hydrolysis. The invention also relates to the novel (R) stereoisomer prepared by the instant process and to its more stable forms. In addition, the invention relates to the use of the (R) stereoisomer in preparing stereoisomers of pharmacologically active compounds and to certain specific stereoisomers produced thereby.Type: GrantFiled: June 4, 1993Date of Patent: August 16, 1994Assignee: Sandoz Ltd.Inventors: Heinrich Estermann, Prasad K. Kapa, Russell L. Underwood, William J. Houlihan
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Patent number: 5338864Abstract: The present invention relates particularly to novel preorganized hexadentate ligands that are suitable for complexing with a radionuclide, and are useful as general imaging agents for diagnostic purposes.Type: GrantFiled: July 6, 1992Date of Patent: August 16, 1994Assignee: Mallinckrodt Medical, Inc.Inventors: Steven R. Woulfe, Raghavan Rajagopalan
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Patent number: 5326801Abstract: New organic phosphites of a specific formula are used as stabilizers for polymers and other organic materials.Type: GrantFiled: July 28, 1992Date of Patent: July 5, 1994Assignee: Himont IncorporatedInventors: Marco Foa, Sauro Strologo
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Patent number: 5312954Abstract: Novel bisphosphonates comprise compounds of the formula (I) ##STR1## wherein m and l are independently 1 or 2; R.sub.1 represents hydrogen, a lower alkyl group, or an alkali metal cation; R.sub.2 represents hydrogen, a lower alkyl group or an alkali metal cation; Y represents .dbd.0 or .dbd.N--OH, or --OH and X represents --(CH.sub.2).sub.n --, a branched alkylene group, or a branched or straight alkenylene or alkynylene chain optionally substituted by one or more oxygen or nitrogen atoms, wherein n is an integer from 3 to 24. Further definitions of X are included in the description.Type: GrantFiled: May 13, 1992Date of Patent: May 17, 1994Assignee: Yissum, Research Development Company of the Hebrew University of JerusalemInventors: Eli Breuer, Gershon Golomb
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Patent number: 5306727Abstract: Cyclophosphamide analogs are provided of the general formula: ##STR1## wherein R.sup.1 and R.sup.2 are each (C.sub.2 -C.sub.6)alkyl, substituted with a leaving group such as halo or alkylsulfonyl, R.sup.3 and R.sup.4 are the same as R.sup.1 and R.sup.2 or are H and Ar is a heteroaromatic ring and the pharmaceutically acceptable salts thereof.Type: GrantFiled: April 30, 1993Date of Patent: April 26, 1994Assignee: Research Corporation Technologies, Inc.Inventors: Richard F. Borch, James P. Schmidt
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Patent number: 5284836Abstract: The invention discloses certain heterocyclic, thioether, keto-ester and alkyl phospholipids, e.g., heterocyclic phospholipids having the formula ##STR1## where R is n-C.sub.14 -C.sub.20 alkyl or O-n-C.sub.14 -C.sub.20 alkyl; each R.sub.1 is methyl or ethyl; n is 2-6; and X is --CH.sub.2 --m, where m is 2-4, CH.sub.2 CH.sub.2 O or CH.sub.2 CH.sub.2 S, or a corresponding hydrate thereof, which compounds are useful in treating multiple sclerosis.Type: GrantFiled: December 4, 1992Date of Patent: February 8, 1994Assignee: Sandoz Ltd.Inventor: William J. Houlihan
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Patent number: 5274155Abstract: A process for the preparation of compounds of formula ##STR1## and pharmaceutically acceptable salts thereof; wherein X is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or --CH.sub.2 O-- (where O is linked to Z); Z is a hydrophobic anchor R.sub.1 is hydrogen, alkyl, cycloalkyl or aryl; comprising the steps of:(A) reacting a compound of formula ##STR2## with a compound of formula ##STR3## or a compound of formula ##STR4## in the presence of an amine base or an alkali metal hydride in an organic solvent to form a compound having the formula ##STR5## (B) heating the compound of formula IX at a temperature of from about 100.degree. C. to about 200.degree. C., to form a compound of formula ##STR6## and (C) quenching the compounds of formula VIII with an acid provides the compounds of formula I.Type: GrantFiled: December 7, 1992Date of Patent: December 28, 1993Assignee: E. R. Squibb & Sons, Inc.Inventors: John K. Thottathil, David Kronenthal
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Patent number: 5262549Abstract: 4-[3-(benz[b]pyran-4-ylidene)prop-1-enyl]benz[b]pyrylium, 4-[5-(4H-benz[b]pyran-4-ylidene)penta-1,3-dienyl]benz[b]pyrylium and 4-[7-(4H-benz[b]pyran-4-ylidene)hepta-1,3,5-trienyl]benz[b]pyrylium dyes, wherein at least one of the benzpyrylium nuclei carries at its 2-position a substituent in which a non-aromatic carbon atom is bonded directly to the benzpyrylium nucleus, subject to the proviso that if the or each 2-substituent contains an aromatic nucleus, this aromatic nucleus is not conjugated with the benzpyrylium nucleus, are useful as visible and near infra-red absorbers, having high extinction coefficients and a reduced tendency to develop absorptions at shorter wavelengths when dispersed in polymeric media.Type: GrantFiled: March 29, 1993Date of Patent: November 16, 1993Assignee: Polaroid CorporationInventors: Stephen J. Telfer, Socorro M. Ramos, Michael J. Zuraw
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Patent number: 5252757Abstract: A cycloadduct of the formula ##STR1## is prepared by reacting 2,2'-(2,5-furandiyldimethylidine)bis-propanedinitrile with 8-methoxypheptafulvene to form a tetrahydroazulene intermediate and then heating a solution of the tetrahydroazulene intermediate in a boiling solvent to drive off methanol.Type: GrantFiled: July 26, 1991Date of Patent: October 12, 1993Assignee: Suddeutsche Zucker-AktiengsellschaftInventors: Jorg Daub, Knut M. Rapp, Petra Seitz, Rainer Wild, Josef Salbeck
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Patent number: 5250522Abstract: The present invention relates to the N-phosphonomethyl-biaryl substituted amino acid derivatives of formula I ##STR1## wherein X represents a direct bond, C.sub.1-4 -alkylene or C.sub.2 -C.sub.4 -alkenylene; R and R' represent independently hydrogen, carbocyclic aryl, 6-tetrahydronaphthyl, 5-indanyl, .alpha.-(trichloromethyl, carboxyl, esterified carboxyl or amidated carboxyl)substituted-(lower alkyl or aryl-lower alkyl), acyloxymethyl optionally monosubstituted on methyl carbon by C.sub.1-20 -alkyl, by C.sub.5 -C.sub.7 -cycloalkyl, by aryl or by aryl-lower alkyl; R.sub.1 represents monocyclic carbocyclic or monocyclic heterocyclic aryl; COR.sub.3 represents carboxyl or carboxyl derivatized in form of a pharmaceutically acceptable ester; R.sub.2 and R.sub.Type: GrantFiled: October 9, 1992Date of Patent: October 5, 1993Assignee: Ciba-Geigy CorporationInventor: Stephane De Lombaert
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Patent number: 5229377Abstract: A process for preparing the (R) stereoisomer of 2,2-bis(hydroxmethyl)-tetrahydrofuran monobutyrate comprising subjecting the dibutyric ester of the 2,2-bis(hydroxymethyl)-tetrahydrofuran to enzymatic hydrolysis. The invention also relates to the novel (R) stereoisomer prepared by the instant process and to its more stable forms. In addition, the invention relates to the use of the (R) stereoisomer in preparing stereoisomers of pharmacologically active compounds and to certain specific stereoisomers produced thereby.Type: GrantFiled: April 26, 1991Date of Patent: July 20, 1993Assignee: Sandoz Ltd.Inventors: Heinrich Estermann, Prasad K. Kapa, Russell L. Underwood, William J. Houlihan
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Patent number: 5229375Abstract: Phosphine oxide-terminated allene-ene-yne compounds are disclosed that possess DNA-cleaving, antimicobial and tumor growth-inhibiting properties. Methods of making and using those compounds are also disclosed.Type: GrantFiled: August 1, 1990Date of Patent: July 20, 1993Assignee: Scripps Clinic and Research FoundationInventors: Peter E. Maligres, Kyriacos C. Nicolaou
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Patent number: 5227499Abstract: Squarylium compounds of the formula: ##STR1## in which: Q.sup.1 and Q.sup.2 are each a Chromophoric group having an unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens;R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group; andR.sup.3, R.sup.4 and R.sup.5 are each independently a hydrogen atom, or an aliphatic, cycloaliphatic, aromatic or heterocyclic group, or an electron-withdrawing group able to lower the electron density at the carbon atom to which it is attached, subject to the provisoes that:two of R.sup.3, R.sup.4 and R.sup.5 may form a divalent group of which a single atom is double bonded to the carbon atom to which the two groups are attached, or all three of R.sup.3, R.sup.4 and R.sup.Type: GrantFiled: November 20, 1991Date of Patent: July 13, 1993Assignee: Polaroid CorporationInventors: Donald A. McGowan, Mark R. Mischke, Stephen J. Telfer
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Patent number: 5227498Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an aliphatic, cycloaliphatic, aromatic or heterocyclic group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a cycloaliphatic or aromatic ring) are useful as near infra-red absorbers.Type: GrantFiled: November 20, 1991Date of Patent: July 13, 1993Assignee: Polaroid CorporationInventors: John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
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Patent number: 5210110Abstract: Silylated acylphosphine oxides of formula I ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are defined in the specification, are highly suitable as photoinitiators for the photopolymerization of compounds which can be polymerized by means of free radicals, namely ethylenically unsaturated compounds.Type: GrantFiled: November 18, 1991Date of Patent: May 11, 1993Assignee: Ciba-Geigy CorporationInventors: Werner Rutsch, Rinaldo Husler
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Patent number: 5190929Abstract: Cyclophosphamides possessing anti-tumor activity and having the formula ##STR1## and salts thereof; wherein R is lower alkyl, aryl, aryl-lower alkyl or a nitrogen, sulfur or oxygen containing heterocyclic or heterocyclic lower alkyl, andR' is hydrogen, hydroxy or OOH with the proviso that when R' is hydrogen, R is other than methyl or phenyl and when R' is hydroxy, R is other than methyl.Type: GrantFiled: May 25, 1988Date of Patent: March 2, 1993Assignee: Research Corporation Technologies, Inc.Inventors: Richard F. Borch, Gregory W. Canute
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Patent number: 5190930Abstract: Araliphatylaminoalkanediphosphonic acids of formula ##STR1## wherein R.sub.1 is an aromatically substituted aliphatic radical, R.sub.2 is hydrogen or a monovalent aliphatic radical and alk is a divalent aliphatic radical, and their salts, exhibit a pronounced regulatory action on the calcium metabolism and can be used as medicaments for the treatment of diseases that are attributable to calcium metabolsim disorders. They are prepared, for example, by reacting a compound of formula ##STR2## wherein X.sub.3 is carboxy and R.sub.0 is a radical R.sub.2, with phosphorous acid and phosphorus trichloride and hydrolysing the primary product.Type: GrantFiled: December 20, 1991Date of Patent: March 2, 1993Assignee: Ciba-Geigy CorporationInventor: Knut A. Jaeggi
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Patent number: 5189023Abstract: Renin inhibiting compounds of the formula: ##STR1## containing two .alpha.-amino acids or a single .alpha.-amino acid wherein R.sub.1 is a phosphorus containing moiety, W is oxygen or NR.sub.3 and A is a moiety selected from those of the formula: ##STR2## wherein Z is O, S, SO, SO.sub.2 and p is an integer from 1 to 2; and, when W is oxygen, A may also be a moiety of the formula ##STR3## and analogs thereof which compounds inhibit the substrate-cleaving action of renin, pharmaceutical compositions containing these compounds, processes for producing the compounds and methods of treating hypertension which employ the novel renin inhibitors.Type: GrantFiled: October 22, 1991Date of Patent: February 23, 1993Assignee: American Cyanamid CompanyInventors: Jay D. Albright, Fuk-Wah Sum
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Patent number: 5183905Abstract: Phenolphthalein bis(dihydrocarbyl phosphates), optionally substituted with chloro or bromo atoms, can be used as fire retardant additives for polymers.Type: GrantFiled: April 20, 1992Date of Patent: February 2, 1993Assignee: Akzo NVInventors: Alan M. Aaronson, Danielle A. Bright
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Patent number: 5183906Abstract: Novel anti-inflammatory furanone compounds have the following formula ##STR1## where R.sub.1 independently is H, phenyl, C.sub.1 -C.sub.6 alkyl substituted phenyl, halogen substituted phenyl, or alkyl of 1 to 6 carbons and n is an integer having the values of 1 or 2, and where when n is 1 the R.sub.1 group is attached either to the 3 or to the 5 position of the 2-furanone, when n is 2 then R.sub.1 is attached to both the 3 and 5 positions, with the proviso that when n is 1 then R.sub.1 is not H; Y.sub.1 is H, alkyl of 1 to 20 carbons, phenyl C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 alkenyl containing one or more olephinic bonds, PO(OH).sub.2, PO(OH)OR.sub.2, PO(OH)R.sub.2, PO(OR.sub.2).sub.2, where R.sub.2 is independently alkyl of 1 to 20 carbons, phenyl, or halogen substituted phenyl or C.sub.1 -C.sub.6 alkyl substituted phenyl, further Y.sub.1 is CO--R.sub.3, CO--OR.sub.3, CONHR.sub.3, SO.sub.2 R.sub.3, SO.sub.2 NHR.sub.3, (CH.sub.2).sub.p --O--R.sub.3, or (CH.sub.2).sub.p --O--(CH.sub.2).sub.m --O--R.Type: GrantFiled: April 30, 1991Date of Patent: February 2, 1993Assignee: Allergan, Inc.Inventors: Gary C. M. Lee, Michael E. Garst, George Sachs
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Patent number: 5169842Abstract: Novel oligophosphates with an antiviral action of the formula ##STR1## in which n is 3-50,B and E are, independently of one another, O, S or NH,A is O, NR or S,D is O, S or NR.sub.2, in which independently each R is H, alkyl, aralkyl or aryl,andX is --(CH.sub.2).sub.Type: GrantFiled: May 9, 1991Date of Patent: December 8, 1992Assignee: Bayer AktiengesellschaftInventors: Antonius Lobberding, Axel C. Heitmann, Burkhard Mielke, Udo Stropp, Axel Kretschmer, Helga Rubsamen-Waigmann, Lothar Biesert, Haryadi Suhartono
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Patent number: 5162548Abstract: New organic phosphites of the formula ##STR1## are used as stabilizers for polymers and other organic materials. The definition of groups R, R', and R.sub.1 may be found in the disclosure.Type: GrantFiled: November 19, 1991Date of Patent: November 10, 1992Assignee: Himont IncorporatedInventors: Marco Foa', Sauro Strologo
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Patent number: 5155100Abstract: The invention relates to the N-phosphonomethyl-biaryl substituted dipeptide derivatives of formula I ##STR1## wherein A represents a direct bond, lower alkylene, phenylene or cyclohexylene; m represents 1 or zero, provided that m represents 1 when A is a direct bond; R.sub.2 represents hydrogen, hydroxy, lower alkyl, aryl-lower alkyl, C.sub.5 -C.sub.Type: GrantFiled: May 1, 1991Date of Patent: October 13, 1992Assignee: Ciba-Geigy CorporationInventors: Mark D. Erion, Stephane De Lombaert
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Patent number: 5153347Abstract: Novel angiotensin II receptor antagonists of the formula ##STR1## wherein X, X.sub.1, X.sub.2, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined herein, are disclosed. These compounds are useful, for example, in the treatment of hypertension, congestive heart failure and cardiac hypertrophy.Type: GrantFiled: January 31, 1991Date of Patent: October 6, 1992Assignee: E. R. Squibb & Sons, Inc.Inventor: John E. Lloyd
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Patent number: 5147866Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein a and b together form an --O-- or --CH.sub.2 -- linkage or a bond;either Y is N and R.sub.2 is hydrogen; orY is C-R.sub.1whereineither one of R.sub.1 and R.sub.2 is hydrogen and the other is nitro, cyano, halo, --CF.sub.3, C.sub.2 F.sub.5, formyl aldoxime, CF.sub.3 O, NO.sub.2 --CH.dbd.CH--, NC--CH.dbd.CH--; a group R.sub.x X-- wherein R.sub.x is C.sub.1-6 alkyl, aryl or heteroaryl either of which may be optionally substituted by one, two or three of C.sub.1-4 alkyl, C.sub.1-4 alkoxy, nitro, halo, CF.sub.3 and cyano; and X is C.dbd.O, O.C.dbd.O, C.dbd.O.O, CHOH, SO, SO.sub.2, O.SO, O.SO.sub.2, CONH, O.CONH, C.dbd.S, O.C.dbd.S, C.dbd.S.O, CH.SH, SONH, SO.sub.2 NH, O.SONH, O.SO.sub.2 NH, CO--CH.dbd.CH, C.dbd.NHOH, C.dbd.NNH.sub.2 ; or a group R.sub.y R.sub.z NZ-- wherein R.sub.y and R.sub.z are independently hydrogen or C.sub.1-6 alkyl and Z is C.dbd.O, SO or SO.sub.2 ; or a group (R.sub.w O).sub.2 P(O)W wherein R.sub.Type: GrantFiled: October 29, 1990Date of Patent: September 15, 1992Assignee: Beecham Group p.l.c.Inventors: Geoffrey Stemp, Gordon Burrell
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Patent number: 5145990Abstract: Compounds of the formula: ##STR1## wherein R.sub.1 is C.sub.2- C.sub.12 linear or branched unsubstituted alkyl; C.sub.1- C.sub.12 linear or branched substituted alkyl; C.sub.2 -C.sub.12 linear or branched monoalkenyl; C.sub.2 -C.sub.12 linear or branched alkynyl; C.sub.7 -C.sub.20 aralkyl, wherein the alkyl chain is linear or branched C.sub.1- C.sub.8 and the aryl moiety is C.sub.6- C.sub.12 ; C.sub.4- C.sub.10 cycloalkylalkyl; C.sub.3- C.sub.7 cycloalkyl; wherein these values for R.sub.1, other than C.sub.2- C.sub.12 linear or branched unsubstituted alkyl, can be substituted by one or more of C.sub.1 -C.sub.4 alkoxy, C.sub.3- C.sub.6 cycloalkyloxy, C.sub.3- C.sub.6 cycloalkylthio, C.sub.6- C.sub.12 aryloxy, C.sub.1- C.sub.4 alkylthio, C.sub.6- C.sub.12 arylthio, C.sub.7- C.sub.10 aralkyloxy, C.sub.7- C.sub.16 aralkyl-thio; and R.sub.5 is H or C.sub.1- C.sub.12 linear or branched alkyl; C.sub.2- C.sub.12 linear or branched monoalkenyl; C.sub.7- C.sub.Type: GrantFiled: January 9, 1991Date of Patent: September 8, 1992Assignee: Merck & Co., Inc.Inventors: William H. Parsons, William R. Schoen, Arthur A. Patchett
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Patent number: 5132204Abstract: A stable 1,2-dioxetane of the formula: ##STR1## wherein X' is a phenyl group with 0 to 2 Cl or I atoms. This 1,2-dioxetane is a double-trigger substrate. The 2-methyl-4-hydroxy-naphthyl group is first removed by horseradish peroxidase. The exposed phosphate group is then removed with alkaline phosphatase. The exposed phenoxy 1,2-dioxetane decomposes to generate chemiluminescence output in immunoassays or nucleic acid hybridization assays.Type: GrantFiled: May 31, 1989Date of Patent: July 21, 1992Assignee: Chiron CorporationInventors: Michael S. Urdea, Brian D. Warner
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Patent number: 5101053Abstract: Radiation sensitive sulfonium salts which contain (1) a sulfonium initiator portion, (2) a spacer portion, and (3) a reactive group portion. The spacer portion has the formula "-o-w- x-z-" wherein "w" is a single bond or one of --C(O)--, --C(O)O--, --C(O)S--, --C(O)NH-- --C(O)N(alkyl)--, --C(S)--, --C(S)S--,--S(O)--, --S(O)(O)--, or --S(O)(O)O--; "X" is an unsubstituted or substituted alkylene radical; and "Z" is --O--, --NH--, --N(C,--C.sub.6 -alkyl)--, or --N(phenyl)--. The reactive group portion is --CH.dbd.CH.sub.2 or --C(O)--C(Y).dbd.CH.sub.2 wherein "Y" is H, C.sub.1 -.sub.6 -alkyl, or phenyl. The sulfonium salts find use in curing monomers which can be subjected to cationic polymerization.Type: GrantFiled: January 9, 1990Date of Patent: March 31, 1992Assignee: BASF AktiengesellschaftInventor: Andreas Boettcher
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Patent number: 5099033Abstract: The present invention is directed to a process of making tetrahydrofuran of the formula (D) ##STR1## resulting in 2,5-diaryltetrahydrofuran PAF antagonists of pharmaceutically acceptable purity.Type: GrantFiled: June 29, 1990Date of Patent: March 24, 1992Assignee: Merck & Co., Inc.Inventors: Ichiro Shinkai, Andrew S. Thompson, Thomas R. Verhoeven
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Patent number: 5095123Abstract: Glycosyl phosphate triesters are prepared by reacting an anomeric mixture of a substituted hexopyranose with 4-N,N-dimethylaminopyridine and diphenyl chlorophosphate wherein using a specific order of addition determines the stereochemistry of the product.Type: GrantFiled: November 30, 1990Date of Patent: March 10, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Subramaniam Sabesan
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Patent number: 5091538Abstract: The present invention refers to dicyanovinylsubstituted furan derivatives, processes for their production and their application. The new furan derivatives are represented by the general formula ##STR1## wherein x.sup.1 and x.sup.2 are equal or different and stand for H, alkyl, alkenyl, aryl, halogen, NO.sub.2 or CN.In the general formula I, n may be 0 or 1. In case of n=0, A means e.g. --CH.sub.2 OR.sup.1 (with e.g. R.sup.1 .dbd.H, alkyl or aryl).The compounds according to this invention can be used directly or in the form of their cycloadducts in several applications of electro-optical fields, e.g. for the manufacture of optical data recording systems or organic (electron) conducting materials or electron-transfer catalysts.Type: GrantFiled: December 5, 1989Date of Patent: February 25, 1992Assignee: Suddeutsche Zucker-AktiengesellschaftInventors: Jorg Daub, Knut M. Rapp, Petra Seitz, Rainer Wild, Josef Salbeck
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Patent number: 5091378Abstract: Compounds which are useful as inhibitors of cholesterol biosynthesis and thus as hypocholesteroleumic agents are provided which have the structure ##STR1## wherein R is OH, or salts thereof or lower alkoxy; R.sup.x is H or alkyl;X is --CH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --CH.sub.2 CH.sub.2 CH.sub.2 -- or --CH.sub.2 O-- (where O is linked to Z);Z is a hydrophobic anchor, such as ##STR2## wherein the dotted lines represent optional double bonds. New intermediates used in preparing the above compounds, pharmaceutical compositions containing such compounds and a method for using such compounds to inhibit cholesterol biosynthesis are also provided.Type: GrantFiled: April 18, 1988Date of Patent: February 25, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Donald S. Karanewsky, Michael C. Badia, Scott A. Biller, Eric M. Gordon, Michael J. Sofia
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Patent number: 5064816Abstract: invention relates to heterocyclic phospholipids of formula III which are useful in treating multiple sclerosis:where R .sub.2 is n-C.sub.14 -C.sub.20 alkyl;each R.sub.1, independently, is methyl or ethyl; Y is --O-- or --S--;n is an integer 2 to 6.Type: GrantFiled: June 5, 1990Date of Patent: November 12, 1991Assignee: Sandoz Ltd.Inventor: William J. Houlihan
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Patent number: 5059611Abstract: New 5-hydroxy-2-furanone compounds have anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis.Type: GrantFiled: October 25, 1989Date of Patent: October 22, 1991Assignee: Allergan, Inc.Inventor: Gary C. M. Lee
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Patent number: 5055471Abstract: This invention relates to derivatives of propanoic acid of the formula ##STR1## Useful as fungicides, insecticides and miticides, to processes for preparing them, to compositions containing them, and to methods of using them to combat fungi, especially fungal infections of plants, and to kill or control insects and mites.Type: GrantFiled: November 15, 1989Date of Patent: October 8, 1991Assignee: Imperial Chemical Industries PLCInventors: Paul J. de Fraine, Anne Martin
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Patent number: 4997820Abstract: Novel macrocyclic compounds of the formual I ##STR1## where the dotted line in the 9,10-position is a saturated bond or a double bond, alternatively, and R is hydrogen, methyl or certain acyl radicals, and R.sub.o is hydrogen, halogen, azido, thiol, hydroxyl or --OY, where Y is, among other radicals, an ether radical, a silyl group, a sulfonyl group, a sugar radical or a (thiol)acyl radical, and R being methyl if there is a double bond in the 9,10-position, have microbicidal properties for the control of phytopathogenic microorganisms. They can be employed in the customary formulation for the control of plant disease.Type: GrantFiled: September 8, 1989Date of Patent: March 5, 1991Assignees: Gesellschaft fur Biotechnologische Forschung mbH, Ciba-Geigy CorporationInventors: Marius Sutter, Norbert Bedorf, Gerhard Hofle, Dietmar Schummer, Bettina Bohlendorf
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Patent number: 4977146Abstract: The present invention is directed to a specifically substituted tetrahydrofuran of the formula (I) ##STR1## wherein R.sup.4 is an alkylthio, alkylsulfinyl or alkylsulfonyl containing group, Y is an alkyl or substituted alkyl group, R.sup.6 is an alkyl or a substituted alkyl group and the substituents at positions 3, 4 or 5 are acyclic.Type: GrantFiled: April 11, 1990Date of Patent: December 11, 1990Assignee: Merck & Co., Inc.Inventors: Tesfaye Biftu, Mitree M. Ponpipom, Nirindar N. Girotra
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Patent number: 4962229Abstract: 3-R.sup.1 -3-oxoprop-1-ene-1,1-diphosphonic acids corresponding to the following general formula ##STR1## in which R.sup.1 is a tertiary substituted alkyl group, an optionally substituted cycloalkyl group, or an optionally substituted aryl or heteroaryl group, andM is hydrogen or the cation of a base;to a process for their production in which 3-R.sup.1 -3-oxo-1-aminopropane-1,1-diphosphonic acids corresponding to the following general formula ##STR2## in which R.sup.1 is as defined above, are reacted with an aqueous or alcoholic alkali metal hydroxide solution; then water followed by an alcohol infinitely miscible with water is added to the reaction mixture, and the pure olefinic diphosphonic acids are obtained by addition of an acid; to the use of the above compounds of formula III as complexing agents and as thresholders; and to compositions containing one or more compounds of formula (III).Type: GrantFiled: June 30, 1989Date of Patent: October 9, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Helmut Blum, Siglinde Hemmann
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Patent number: 4933472Abstract: Substituted aminomethylenebis(phosphonic acid) derivatives represented by the general formula: ##STR1## in which R.sup.1, R.sup.2 R.sup.3 and R.sup.4 may be the same or different, each represents a hydrogen atom or a lower alkyl group; "m" is zero or represents an integer from 1 to 4; and a ring "A" represents a cycloalkenyl group having 5 to 8 carbon atoms, a bicycloheptyl group, a bicycloheptenyl group or a saturated heterocyclic group having 4 to 7 carbon atoms and containing an oxygen atom, a sulfur atom, a sulfinyl group (--SO--) or a sulfonyl group (--SO.sub.2 --),or pharmaceutically acceptable salts thereof.Type: GrantFiled: April 5, 1989Date of Patent: June 12, 1990Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Yasuo Isomura, Makoto Takeuchi, Shuichi Sakamoto, Tetsushi Abe
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Patent number: 4927835Abstract: Compounds of the formula (I): ##STR1## or a pharmaceutically acceptable salt thereof, wherein: R.sup.1 is cycloalkyl of 5 to 7 carbon atoms; aryl of 6 to 10 carbon atoms unsubstituted or substituted by straight or branched chain alkyl of 1 to 4 carbon atoms, halo or trifluoromethyl; or ##STR2## wherein A is oxygen, sulfur or NR.sup.5, wherein R.sup.5 is hydrogen, straight or branched chain alkyl of 1 to 4 carbon atoms or halo, and R.sup.6 is hydrogen, straight or branched chain alkyl of 1 to 4 carbon atoms or halo;R.sup.2 is straight or branched chain alkyl of 1 to 4 carbon atoms or cycloalkyl of 5 to 7 carbon atoms; andR.sup.3 and R.sup.4 are the same or different and each is hydrogen; straight or branched chain alkyl of 1 to 8 carbon atoms unsubstituted or substituted by hydroxy, acyloxy of 2 to 5 carbon atoms, carboxyl or carbamoyl;are useful for treating pain, inflammation and fever in humans and animals.Type: GrantFiled: March 1, 1989Date of Patent: May 22, 1990Assignee: Nippon Shinyaku Co., Ltd.Inventors: Masahiro Kise, Yoshihiko Yoshimoto, Hiroshi Fujisawa, Yasuo Sasaki, Shoji Yasufuku
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Patent number: 4918098Abstract: Compounds are described of formula (I) ##STR1## and salts thereof, wherein R.sup.1 a methyl, ethyl or isopropyl group;R.sup.2 is --H, --OH, substituted --OH or a phosphate ester group and R.sup.3 is --H, or R.sup.2 and R.sup.3 together with the carbon atom to which they are attached represent a >C=0 groupand OR.sup.4 is a group OR.sup.5 as defined above;with the proviso that either R.sup.2 represents a group OR.sup.5 (where OR.sup.5 is an alkoxy group OR.sup.7 in which R.sup.7 represents a C.sub.1-6 alkyl substituted by a halogen atom or C.sub.2-6 alkyl interrupted by --O-- or --S--) or at least one of R.sup.2 and OR.sup.4 is a phosphate ester group or a group OCONR.sup.10 R.sup.11 (where R.sup.10 and R.sup.11 are --H or C.sub.1-4 alkyl).These compounds may be used for controlling insect, acarine, nematode or other pests.Type: GrantFiled: March 11, 1987Date of Patent: April 17, 1990Assignee: American Cyanamid CompanyInventors: Michael V. J. Ramsay, Edward P. Tiley, Oswy Z. Pereira, John B. Ward, Neil Porter, Hazel M. Noble, Richard A. Fletton, David Noble, Derek R. Sutherland
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Patent number: 4880575Abstract: 3-R.sup.1 -3-oxoprop-1-ene-1,1-diphosphonic acids corresponding to the following general formula ##STR1## in which R.sup.1 is a tertiary substituted alkyl group, an optionally substituted cycloalkyl group, or an optionally substituted aryl or heteroaryl group, andM is hydrogen or the cation of a base;to a process for their production in which 3-R.sup.1 -3-oxo-1-aminopropane-1,1-diphosphonic acids corresponding to the following general formula ##STR2## in which R.sup.1 is as defined above, are reacted with an aqueous or alcoholic alkali metal hydroxide solution; then water followed by an alcohol infinitely miscible with water is added to the reaction mixture, and the pure olefinic diphosphonic acids are obtained by addition of an acid; to the use of the above compounds of formula III as complexing agents and as thresholders; and to compositions containing one or more compounds of formula (III).Type: GrantFiled: July 22, 1988Date of Patent: November 14, 1989Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Helmut Blum, Siglinde Hemmann