Phosphorus Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/218)
  • Patent number: 5436245
    Abstract: 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: Grant
    Filed: November 17, 1993
    Date of Patent: July 25, 1995
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Donald S. Karanewsky
  • Patent number: 5407922
    Abstract: 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: Grant
    Filed: May 3, 1993
    Date of Patent: April 18, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Christian Marescaux, Raymond Bernasconi, Markus Schmutz, Wolfgang Frostl, Stuart J. Mickel
  • Patent number: 5405976
    Abstract: Dyes comprising an inner salt of a compound of the formula:Q.sup.1 =Z-Q.sup.2wherein:Q.sup.1 is a 4-(benz[b]-4H-pyrylium)methylidene, 4-(benz[b]-4H-thiopyrylium)methylidene or 4-(benz[b]-4H-selenopyrylium)methylidene grouping;Z is a 1,3-(2-hydroxy-4-oxo-2-cyclobutylidene) hydroxide or 1,3-(2-hydroxy-4,5-dioxo-2-cyclopentylidene) hydroxide ring; andQ.sup.2 is a 4-(benz[b]-4H-pyran-4-ylidene)methyl, 4-(benz[b]-4H-thiopyran-4-ylidene)methyl or 4-(benz[b]-4H-selenopyran-4-ylidene)methyl grouping;wherein at least one of the groupings Q.sup.1 and Q.sup.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: April 11, 1995
    Assignee: Polaroid Corporation
    Inventors: Stephen J. Telfer, Robert P. Short, Stephen G. Stroud, Anthony J. Puttick, Socorro Ramos, Michael J. Zuraw
  • Patent number: 5405841
    Abstract: 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: Grant
    Filed: November 30, 1993
    Date of Patent: April 11, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Fritz Maurer, Jurgen Hartwig, Christoph Erdelen
  • Patent number: 5386017
    Abstract: 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: Grant
    Filed: February 26, 1990
    Date of Patent: January 31, 1995
    Assignee: Board of Governors of Wayne State University
    Inventor: Arthur P. Schaap
  • Patent number: 5374628
    Abstract: 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: Grant
    Filed: October 18, 1993
    Date of Patent: December 20, 1994
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Scott A. Biller
  • Patent number: 5371248
    Abstract: 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: Grant
    Filed: February 22, 1993
    Date of Patent: December 6, 1994
    Assignee: Mobil Oil Corporation
    Inventor: Leslie R. Rudnick
  • Patent number: 5354873
    Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an aromatic unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an acyl, aliphatic, cycloaliphatic, aromatic or heterocyclic group, subject to the proviso that one of R.sup.3 and R.sup.4 may be an amino or substituted amino group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a nitrogenous heterocyclic ring) are useful as near infra-red absorbers.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: October 11, 1994
    Assignee: Polaroid Corporation
    Inventors: Richard M. Allen, Peter K. Chu, John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
  • Patent number: 5338730
    Abstract: 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: Grant
    Filed: June 4, 1993
    Date of Patent: August 16, 1994
    Assignee: Sandoz Ltd.
    Inventors: Heinrich Estermann, Prasad K. Kapa, Russell L. Underwood, William J. Houlihan
  • Patent number: 5338864
    Abstract: 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: Grant
    Filed: July 6, 1992
    Date of Patent: August 16, 1994
    Assignee: Mallinckrodt Medical, Inc.
    Inventors: Steven R. Woulfe, Raghavan Rajagopalan
  • Patent number: 5326801
    Abstract: New organic phosphites of a specific formula are used as stabilizers for polymers and other organic materials.
    Type: Grant
    Filed: July 28, 1992
    Date of Patent: July 5, 1994
    Assignee: Himont Incorporated
    Inventors: Marco Foa, Sauro Strologo
  • Patent number: 5312954
    Abstract: 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: Grant
    Filed: May 13, 1992
    Date of Patent: May 17, 1994
    Assignee: Yissum, Research Development Company of the Hebrew University of Jerusalem
    Inventors: Eli Breuer, Gershon Golomb
  • Patent number: 5306727
    Abstract: 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: Grant
    Filed: April 30, 1993
    Date of Patent: April 26, 1994
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Richard F. Borch, James P. Schmidt
  • Patent number: 5284836
    Abstract: 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: Grant
    Filed: December 4, 1992
    Date of Patent: February 8, 1994
    Assignee: Sandoz Ltd.
    Inventor: William J. Houlihan
  • Patent number: 5274155
    Abstract: 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: Grant
    Filed: December 7, 1992
    Date of Patent: December 28, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: John K. Thottathil, David Kronenthal
  • Patent number: 5262549
    Abstract: 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: Grant
    Filed: March 29, 1993
    Date of Patent: November 16, 1993
    Assignee: Polaroid Corporation
    Inventors: Stephen J. Telfer, Socorro M. Ramos, Michael J. Zuraw
  • Patent number: 5252757
    Abstract: 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: Grant
    Filed: July 26, 1991
    Date of Patent: October 12, 1993
    Assignee: Suddeutsche Zucker-Aktiengsellschaft
    Inventors: Jorg Daub, Knut M. Rapp, Petra Seitz, Rainer Wild, Josef Salbeck
  • Patent number: 5250522
    Abstract: 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: Grant
    Filed: October 9, 1992
    Date of Patent: October 5, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Stephane De Lombaert
  • Patent number: 5229377
    Abstract: 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: Grant
    Filed: April 26, 1991
    Date of Patent: July 20, 1993
    Assignee: Sandoz Ltd.
    Inventors: Heinrich Estermann, Prasad K. Kapa, Russell L. Underwood, William J. Houlihan
  • Patent number: 5229375
    Abstract: 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: Grant
    Filed: August 1, 1990
    Date of Patent: July 20, 1993
    Assignee: Scripps Clinic and Research Foundation
    Inventors: Peter E. Maligres, Kyriacos C. Nicolaou
  • Patent number: 5227499
    Abstract: Squarylium compounds of the formula: ##STR1## in which: Q.sup.1 and Q.sup.2 are each a Chromophoric group having an unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens;R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group; andR.sup.3, R.sup.4 and R.sup.5 are each independently a hydrogen atom, or an aliphatic, cycloaliphatic, aromatic or heterocyclic group, or an electron-withdrawing group able to lower the electron density at the carbon atom to which it is attached, subject to the provisoes that:two of R.sup.3, R.sup.4 and R.sup.5 may form a divalent group of which a single atom is double bonded to the carbon atom to which the two groups are attached, or all three of R.sup.3, R.sup.4 and R.sup.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: July 13, 1993
    Assignee: Polaroid Corporation
    Inventors: Donald A. McGowan, Mark R. Mischke, Stephen J. Telfer
  • Patent number: 5227498
    Abstract: Squarylium compounds of the formula: ##STR1## (in which Q.sup.1 and Q.sup.2 are each a chromophoric group having an unsaturated system conjugated with the squarylium ring and such that in the compounds of formulae Q.sup.1 CH.sub.2 R.sup.1 and Q.sup.2 CH.sub.2 R.sup.2 the methylene hydrogens are active hydrogens, R.sup.1 and R.sup.2 are each independently a hydrogen atom or an aliphatic or cycloaliphatic group, and R.sup.3 and R.sup.4 are each independently a hydrogen atom, or an aliphatic, cycloaliphatic, aromatic or heterocyclic group, or one of R.sup.3 and R.sup.4 is a hydrogen atom and the other is an organosulfonyl group, or R.sup.3 and R.sup.4 together with the intervening nitrogen atom form a cycloaliphatic or aromatic ring) are useful as near infra-red absorbers.
    Type: Grant
    Filed: November 20, 1991
    Date of Patent: July 13, 1993
    Assignee: Polaroid Corporation
    Inventors: John W. Lee, Donald A. McGowan, Mark R. Mischke, Socorro M. Ramos, Stephen J. Telfer
  • Patent number: 5210110
    Abstract: 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: Grant
    Filed: November 18, 1991
    Date of Patent: May 11, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Rutsch, Rinaldo Husler
  • Patent number: 5190929
    Abstract: 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: Grant
    Filed: May 25, 1988
    Date of Patent: March 2, 1993
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Richard F. Borch, Gregory W. Canute
  • Patent number: 5190930
    Abstract: 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: Grant
    Filed: December 20, 1991
    Date of Patent: March 2, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Knut A. Jaeggi
  • Patent number: 5189023
    Abstract: 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: Grant
    Filed: October 22, 1991
    Date of Patent: February 23, 1993
    Assignee: American Cyanamid Company
    Inventors: Jay D. Albright, Fuk-Wah Sum
  • Patent number: 5183905
    Abstract: Phenolphthalein bis(dihydrocarbyl phosphates), optionally substituted with chloro or bromo atoms, can be used as fire retardant additives for polymers.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: February 2, 1993
    Assignee: Akzo NV
    Inventors: Alan M. Aaronson, Danielle A. Bright
  • Patent number: 5183906
    Abstract: 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: Grant
    Filed: April 30, 1991
    Date of Patent: February 2, 1993
    Assignee: Allergan, Inc.
    Inventors: Gary C. M. Lee, Michael E. Garst, George Sachs
  • Patent number: 5169842
    Abstract: 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: Grant
    Filed: May 9, 1991
    Date of Patent: December 8, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Antonius Lobberding, Axel C. Heitmann, Burkhard Mielke, Udo Stropp, Axel Kretschmer, Helga Rubsamen-Waigmann, Lothar Biesert, Haryadi Suhartono
  • Patent number: 5162548
    Abstract: 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: Grant
    Filed: November 19, 1991
    Date of Patent: November 10, 1992
    Assignee: Himont Incorporated
    Inventors: Marco Foa', Sauro Strologo
  • Patent number: 5155100
    Abstract: 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: Grant
    Filed: May 1, 1991
    Date of Patent: October 13, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Mark D. Erion, Stephane De Lombaert
  • Patent number: 5153347
    Abstract: 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: Grant
    Filed: January 31, 1991
    Date of Patent: October 6, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: John E. Lloyd
  • Patent number: 5147866
    Abstract: 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: Grant
    Filed: October 29, 1990
    Date of Patent: September 15, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Geoffrey Stemp, Gordon Burrell
  • Patent number: 5145990
    Abstract: 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: Grant
    Filed: January 9, 1991
    Date of Patent: September 8, 1992
    Assignee: Merck & Co., Inc.
    Inventors: William H. Parsons, William R. Schoen, Arthur A. Patchett
  • Patent number: 5132204
    Abstract: 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: Grant
    Filed: May 31, 1989
    Date of Patent: July 21, 1992
    Assignee: Chiron Corporation
    Inventors: Michael S. Urdea, Brian D. Warner
  • Patent number: 5101053
    Abstract: 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: Grant
    Filed: January 9, 1990
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventor: Andreas Boettcher
  • Patent number: 5099033
    Abstract: 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: Grant
    Filed: June 29, 1990
    Date of Patent: March 24, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Ichiro Shinkai, Andrew S. Thompson, Thomas R. Verhoeven
  • Patent number: 5095123
    Abstract: 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: Grant
    Filed: November 30, 1990
    Date of Patent: March 10, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Subramaniam Sabesan
  • Patent number: 5091538
    Abstract: 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: Grant
    Filed: December 5, 1989
    Date of Patent: February 25, 1992
    Assignee: Suddeutsche Zucker-Aktiengesellschaft
    Inventors: Jorg Daub, Knut M. Rapp, Petra Seitz, Rainer Wild, Josef Salbeck
  • Patent number: 5091378
    Abstract: 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: Grant
    Filed: April 18, 1988
    Date of Patent: February 25, 1992
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Donald S. Karanewsky, Michael C. Badia, Scott A. Biller, Eric M. Gordon, Michael J. Sofia
  • Patent number: 5064816
    Abstract: 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: Grant
    Filed: June 5, 1990
    Date of Patent: November 12, 1991
    Assignee: Sandoz Ltd.
    Inventor: William J. Houlihan
  • Patent number: 5059611
    Abstract: 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: Grant
    Filed: October 25, 1989
    Date of Patent: October 22, 1991
    Assignee: Allergan, Inc.
    Inventor: Gary C. M. Lee
  • Patent number: 5055471
    Abstract: 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: Grant
    Filed: November 15, 1989
    Date of Patent: October 8, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Paul J. de Fraine, Anne Martin
  • Patent number: 4997820
    Abstract: 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: Grant
    Filed: September 8, 1989
    Date of Patent: March 5, 1991
    Assignees: Gesellschaft fur Biotechnologische Forschung mbH, Ciba-Geigy Corporation
    Inventors: Marius Sutter, Norbert Bedorf, Gerhard Hofle, Dietmar Schummer, Bettina Bohlendorf
  • Patent number: 4977146
    Abstract: 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: Grant
    Filed: April 11, 1990
    Date of Patent: December 11, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Tesfaye Biftu, Mitree M. Ponpipom, Nirindar N. Girotra
  • Patent number: 4962229
    Abstract: 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: Grant
    Filed: June 30, 1989
    Date of Patent: October 9, 1990
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Helmut Blum, Siglinde Hemmann
  • Patent number: 4933472
    Abstract: 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: Grant
    Filed: April 5, 1989
    Date of Patent: June 12, 1990
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Yasuo Isomura, Makoto Takeuchi, Shuichi Sakamoto, Tetsushi Abe
  • Patent number: 4927835
    Abstract: 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: Grant
    Filed: March 1, 1989
    Date of Patent: May 22, 1990
    Assignee: Nippon Shinyaku Co., Ltd.
    Inventors: Masahiro Kise, Yoshihiko Yoshimoto, Hiroshi Fujisawa, Yasuo Sasaki, Shoji Yasufuku
  • Patent number: 4918098
    Abstract: 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: Grant
    Filed: March 11, 1987
    Date of Patent: April 17, 1990
    Assignee: American Cyanamid Company
    Inventors: 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
  • Patent number: 4880575
    Abstract: 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: Grant
    Filed: July 22, 1988
    Date of Patent: November 14, 1989
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Helmut Blum, Siglinde Hemmann