Chalcogen Attached Indirectly To The Phosphorus By Acyclic Nonionic Bonding Patents (Class 558/169)
- Nitrogen bonded directly to the phosphorus (Class 558/171)
- The -C(=X)- is part of a -C(=X)X- group, wherein the X's may be the same or diverse chalcogens (Class 558/172)
- Chalcogen, or additional -C(=X), bonded directly to the nitrogen (Class 558/173)
- Two carbons bonded directly to the same chalcogen (e.g., sulfones, carboxylic acid esters, ethers, etc.) (Class 558/174)
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Patent number: 5554773Abstract: The present invention related to novel (R)-dimethyl N-tritylaspartate and novel (R)-alkyl N-trityl-4-oxo-5-phosphononorvalinate derivatives which are useful in the preparation of the class of beta-ketophosphonate NMDA antagonists.Type: GrantFiled: May 12, 1995Date of Patent: September 10, 1996Assignee: Merrell Pharmaceuticals Inc.Inventors: Jeffrey P. Whitten, Duane E. Rudisill
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Patent number: 5543402Abstract: The present invention provides [3-(C.sub.16 -C.sub.18)-alkaesulphinyl- and -sulphonyl-2-methoxy-methylpropyl]-(2-trimethylammonioethyl) phosphates having superior anti-tumor activity.Type: GrantFiled: July 23, 1993Date of Patent: August 6, 1996Assignee: Boehringer Mannheim GmbHInventors: Elmar Bosies, Dieter Herrmann, Wulf Pahlke
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Patent number: 5538957Abstract: Compounds of the formula (I) in which: R is a possibly substituted amino group of the general form --NR.sub.1 R.sub.2, in which R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, lower alkenyl or lower alkinyl, or R is a saturated, unsaturated or aromatic heterocyclic ring which may be mono or bi-substituted by lower alkyl or halogen; alk is a valency bond, a methylene, a saturated or unsaturated, straight or branched-chain alkylene chain with 2-6 carbon atoms; and R.sup.3, R.sup.4, R.sup.5 are independently hydrogen, lower alkyl or benzyl; and their pharmacologically acceptable salts and enantiomers where, if R.sup.3 .dbd.R.sup.4 .dbd.R.sup.5 .dbd.CH.sub.3 and alk is a valency bond, R may not be the dimethyl amino group. Process for their production and medicaments containing these compounds, for the treatment of calcium metabolic complaints.Type: GrantFiled: June 3, 1994Date of Patent: July 23, 1996Assignee: Boehringer Mannheim GmbHInventors: Christos Tsaklakidis, Elmar Bosies, Angelika Esswein, Frieder Bauss
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Patent number: 5523450Abstract: A process for preparing substantially dry GPC (glycerophosphocholine in enantiomeric form) from wet GPC without racemisation, comprises subjecting the wet GPC to reduced pressure and elevated temperature, to reduce the water content and give highly viscous GPC; adding ethanol or another suitable solvent and crystallising GPC therefore with cooling; filtering the crystalline GPC and removing solvent therefrom under reduced pressure; characterised in that the elevated temperature is at least 45.degree. C.; and the solvent is added to the highly viscous GPC. This process produces an apparently new form of L-.alpha.-Glycerophosphocholine, m.p. 148.degree.-152.degree. C.Type: GrantFiled: October 3, 1994Date of Patent: June 4, 1996Assignee: Genzyme LimitedInventors: Christopher T. Evans, Raymond McCague, Nicholas D. Tyrrell
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Patent number: 5519007Abstract: Novel derivatives of lysophingolipids free from sialic acids which are N-acyllysosphingolipids having one of the two formulae: ##STR1## in which --A-- stands for the group --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --, n.sub.1 is a whole number of between 6 and 18, n.sub.2 is a whole number of between 11 and 15, X is a hydrogen atom or the residue of a monosaccharide or a disaccharide or phosphorylcholine and R represents an alkyl radical derived from a saturated or unsaturated aliphatic carboxylic acid having from 2 to 24 carbon atoms substituted by one or more polar groups. The lysosphingolipid derivatives of the invention exhibit an inhibiting action on protein-kinase C activation and, thus, can be utilized in therapies for various pathologies of the nervous system.Type: GrantFiled: July 21, 1992Date of Patent: May 21, 1996Assignee: Fidia, S.p.A.Inventors: Francesco Della Valle, Aurelio Romeo
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Patent number: 5519159Abstract: Disclosed are a phosphatidylcholine excellent in oxidation stability, in which the ratio of the total weight of palmitoyl-linoleoyl-glycerophosphocholine (PLPC) and palmitoyl-oleoyl-glycerophosphocholine (POPC) to the total weight of stearoyl-linoleoyl-glycerophosphocholine (SLPC) and stearoyl-oleoyl-glycerophosphocholine (SOPC) is 4.5 or less, the PLPC, POPC, SLPC and SOPC being molecular species constituting the phosphatidylcholine, and in which the electric conductivity of a 5 wt. % suspension of the phosphatidylcholine in distilled water is 100 .mu.S/cm or less; and a process for producing the same.Type: GrantFiled: April 14, 1995Date of Patent: May 21, 1996Assignee: Kewpie Kabushiki KaishaInventors: Hitoshi Narabe, Hideaki Kobayashi, Mineo Hasegawa
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Patent number: 5516767Abstract: Compounds of the formula ##STR1## where X.sub.1 and X.sub.2 are independently O or S, andR.sub.1 is as defined in the descriptionR.sub.2, R.sub.3, and R.sub.4 are each independently straight orbranched chain (C.sub.1-4)alkyl, and pharmaceutically acceptable salts, physiological hydrolysable esters, and pro-drug forms thereof are useful as hypoglycemic agents.Type: GrantFiled: January 17, 1995Date of Patent: May 14, 1996Assignee: Sandoz Ltd.Inventors: Robert C. Anderson, James D. Fraser, Howard C. Smith, Jeffrey W. Hughes, Edwin B. Villhauer, Gregory R. Bebernitz
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Patent number: 5508463Abstract: Novel .alpha.-aminophosphonates are provided along with processes and intermediates for their preparation. In preferred embodiments, scalemic .alpha.-aminophosphonates are prepared by the stereoselective addition of phosphite salts to chiral imines.Type: GrantFiled: March 17, 1994Date of Patent: April 16, 1996Assignee: Trustees of the University of PennsylvaniaInventors: Amos B. Smith, III, Kraig M. Yager, Carol M. Taylor
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Patent number: 5506217Abstract: This invention pertains to the synthesis and usc as anti-cancer therapeutic agents of a group of substances with a glycerol backbone linked to phosphonocholinc, or other phosphorus-containing head groups, of the following formula: ##STR1## wherein n is 0 to 14 and R.sub.1 is an alkyl group containing 12 to 20 carbon atoms, R.sub.2 is a methyl group, n=0 to 14 and m=2 to 10, or enantiomer thereof, or mixture of stereoisomers. This invention also pertains to the following formula: ##STR2## wherein n is 15 to 17; R1 is an alkyl group: m is 0 to 2; T is an oxygen atom or a methylene; and R.sub.2 is a choline group and therapeutically effective pharmaceutically acceptable salts thereof. These thiophosphonolipids are useful for treating cancer in a mammal in need of cancer treatment.Type: GrantFiled: November 10, 1994Date of Patent: April 9, 1996Assignee: The University of British ColumbiaInventors: Hassan Salari, Robert Bittman
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Patent number: 5466853Abstract: A diester monomer is represented by the formula (I) ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 represent a hadrogen atom, an alkoxy, alkenyloxy or hydroxyalkyloxy carbonyl group having 1 to 20 carbon atoms, or a phosphorylcholine derivative ##STR2## where Y denotes --(CH.sub.2)n, --(CH.sub.2 CH.sub.2 O).sub.n CH.sub.2 CH.sub.2 -- ##STR3## n denotes 1 to 8, m is an integer of 0 or 1, R.sub.4, R.sub.5 and R.sub.6 denote an alkyl or aryl group having 1 to 8 carbon atoms, or a hydroxyalkyl group having 2 to 20 carbon atoms; on the proviso that if R.sub.1 is a hydrogen atom, neither R.sub.2 nor R.sub.3 is a hydrogen atom and at least one of R.sub.2 and R.sub.3 denotes the aforesaid phosphorylcholine derivative group, and that if R.sub.2 is a hydrogen atom, neither R.sub.1 nor R.sub.3 is a hydrogen atom and at least one of R.sub.1 and R.sub.3 denotes the aforesaid phosphorycholine derivative group.Type: GrantFiled: July 19, 1993Date of Patent: November 14, 1995Assignee: NOF CorporationInventors: Yasumi Koinuma, Takeo Matsumoto, Nobuharu Nakada, Nobuo Nakabayashi, Kazuhiko Ishihara
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Patent number: 5436234Abstract: The present invention provides compounds of the formula: ##STR1## wherein R is a erucyl, brassidyl or nervonyl radical, R.sup.1, R.sup.2 and R.sup.3 are defined in the specification, A is a valency bond or a radical as defined in the specification, and X is an oxygen atom when A is a valency bond or is an oxygen or sulphur atom when A is another radical.The present invention also provides a process for the preparation of the compounds of general formula (I) and pharmaceutical compositions containing them which can be used for the treatment of protozoal and fungal diseases, auto-immune diseases and bone marrow damage.Type: GrantFiled: February 28, 1994Date of Patent: July 25, 1995Assignee: Max-Planck-Gesellschaft zur ForderungInventor: Hansjorg Eibl
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Patent number: 5429674Abstract: N-acyl aminomethylene phosphonates are provided having a group defined by the following general formula: ##STR1## wherein R.sub.1 is hydrogen, an aliphatic radical having 1 to 25 carbon atoms, or an aromatic radical having 6 to 25 carbon atoms; R.sub.2 is hydrogen, an aliphatic radical having 1 to 25 carbon atoms, or an aromatic radical having 6 to 25 carbon atoms; and R.sub.3 is a group remaining after reaction of a hydroxyl group-containing or epoxy group-containing polymer with an acidic hydrogen of a ##STR2## group. Also provided are waterborne coating compositions containing metallic pigments which are normally reactive with water or moisture to release hydrogen gas, stabilized against gassing by incorporation of these N-acyl aminomethylene phosphonates into the waterborne coating compositions.Type: GrantFiled: September 12, 1994Date of Patent: July 4, 1995Assignee: PPG Industries, Inc.Inventors: Paul H. Lamers, Kurt G. Olson, James E. Poole, Douglas W. Maier
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Patent number: 5430169Abstract: The present invention provides a series of non-toxic compounds which function to inhibit the activity of S-1-P aldolase in respect to its cleavage of S-1-P. These inhibitors are described by the compounds of formula I ##STR1## wherein R is a radical containing 1 to 15 carbon atoms, a halogen, or hydrocarbon, R' is an organic radical or hydrogen, and R" is --NH.sub.3.sup.+ or --NH--NH .sup.+, with the proviso that, when R is CH.sub.3 (CH).sub.12 (CH.dbd.CH) and R' is hydrogen, R" is --NH--NH.sub.3.sup.+.A method for preparing such compounds, which may generally be described as 1-phosphate derivatives of compounds which include a 2-amino-1,3-alcohol radical is also disclosed.Type: GrantFiled: February 14, 1994Date of Patent: July 4, 1995Assignee: The United States of America represented by the Department of Health and Human ServicesInventors: Ahcene Boumendjel, Stephen P. F. Miller
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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
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Patent number: 5424474Abstract: The present invention relates to fluorinated carboxylic acid esters of phosphono- and phosphinocarboxylic acids containing hydroxyl and/or mercapto groups, their use as waterproofing and/or oil-repellency agents, and a method for their preparation.Type: GrantFiled: December 23, 1993Date of Patent: June 13, 1995Assignee: Bayer AGInventors: Klaus Pohmer, Rainer Weber, Hans-Dieter Block, Hans-Heinrich Moretto
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Patent number: 5424441Abstract: N-aralkyl- and N-heteroaralkyl-aminoalkanephosphinic acids of formula I ##STR1## wherein R is an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, araliphatic or heteroarylaliphatic radical having at least 2 carbon atoms, R.sub.1 is hydrogen or hydroxy, R.sub.2 is an araliphatic or heteroarylaliphatic radical substituted by free or functionally modified carboxy that is bonded directly or by way of a spacer, and R.sub.3 is hydrogen, lower alkyl or a group R.sub.2, and the salts thereof have valuable nootropic and anti-epileptic properties and can be used in the preparation of a nootropic or anti-epileptic medicament.Type: GrantFiled: May 4, 1994Date of Patent: June 13, 1995Assignee: Ciba-Geigy CorporationInventors: Stuart J. Mickel, Wolfgang Frostl, Pascal Furet
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Patent number: 5420330Abstract: Ether variant lipids bound to phosphoramidites are disclosed. These can be used to create oligonucleotides that are linked to stable lipid-like units. For example, dialkyl glycerols are linked to phosphoramidites.Type: GrantFiled: September 7, 1990Date of Patent: May 30, 1995Assignee: Pharmacia P-L Biochemicals Inc.Inventor: Charles K. Brush
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Patent number: 5420329Abstract: The invention relates to a process for the enantioselective preparation of L-phosphinothricin (L-Ptc) and derivatives of the formula I ##STR1## in which R.sup.1 is H, (C.sub.1 -C.sub.6)-alkyl, (C.sub.1 -C.sub.4)-haloalkyl, (C.sub.3 -C.sub.6)-cycloalkyl or (subst.) phenyl-(C.sub.1 -C.sub.4)-alkyl, R.sup.2 is hydrogen, formyl, [(C.sub.1 -C.sub.6)alkyl]carbonyl, [(C.sub.1 -C.sub.6)alkoxy]carbonyl, (subst.) benzyloxycarbonyl, (C.sub.1 -C.sub.6)-alkylsulfonyl or (subst.) (C.sub.6 -C.sub.10)-arylsulfonyl, and R.sup.3 is OH, NH.sub.2 or (C.sub.1 -C.sub.6)-alkoxy, or their salts with acids or bases.Type: GrantFiled: July 25, 1994Date of Patent: May 30, 1995Assignee: Hoechst AktiengesellschaftInventor: Hans-Jaochim Zeiss
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Patent number: 5414102Abstract: The present invention relates to fluorinated carboxylic acid esters of phosphonocarboxylic acids containing acrylate and/or methacrylate groups, their use as waterproofing or oil-repellency agents, and a method for their preparation.Type: GrantFiled: December 27, 1993Date of Patent: May 9, 1995Assignee: Bayer AktiengesellschaftInventors: Klaus Pohmer, Rainer Weber, Hans-Dieter Block, Hans-Heinrich Moretto
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Patent number: 5412137Abstract: A process for preparing compounds of the formula ##STR1## where X.sub.1 and X.sub.2 are independently O or S, andR.sub.1 is as defined herein,R.sub.2, R.sub.3, and R.sub.4 are each independently straight or branched chain (C.sub.1-4)alkyl,and pharmaceutically acceptable salts, physiological hydrolyzable esters, and pro-drug forms thereof, which are useful as hypoglycemic agents.Type: GrantFiled: February 16, 1994Date of Patent: May 2, 1995Assignee: Sandoz Ltd.Inventors: Mahavir Prashad, Prasad K. Kapa
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Patent number: 5403932Abstract: Compounds of the formula: ##STR1## which is further defined herein, possess anti-tumor activity.Type: GrantFiled: June 15, 1994Date of Patent: April 4, 1995Assignee: Research Corporation Technologies, Inc.Inventors: Richard F. Borch, Gregory W. Canute, Ronald R. Valente
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Patent number: 5391800Abstract: A method of inhibiting tumor cell chemotactic and/or chemoinvasion motility comprising contacting the tumor cell with an inhibitory amount of an agent selected from the group consisting of sphingosine-1-phosphate, derivatives of sphingosine-1-phosphate and mimetics of the sphingosine-1-phosphate or of the derivatives. A method of inhibiting phagokinetic activity of tumor cells and neutrophils comprising contacting the cells with a phagokinetic inhibitory amount of an agent selected from the group consisting of sphingosine-1-phosphate, derivatives of sphingosine-1-phosphate, and mimetics of the sphingosine-1-phosphate or of the derivatives. A method of inhibiting tumor cell metastasis comprising administering to a host in need of treatment a metastasis inhibitory amount of an agent selected from the group consisting of sphingosine-1-phosphate, derivatives of sphingosine-1-phosphate, and mimetics of the sphingosine-1-phosphate or of the derivatives, and pharmaceutically acceptable salts of the agent.Type: GrantFiled: August 9, 1993Date of Patent: February 21, 1995Assignee: The Biomembrane InstituteInventors: Yasuyuki Igarashi, Fuqiang Ruan, Yoshito Sadahira, Shigeyuki Kawa, Sen-itiroh Hakomori
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Patent number: 5376684Abstract: Novel compounds of formula I ##STR1## wherein R is selected from butyl, diethoxymethyl, cyclohexylmethyl, cyclohex-3-enylmethyl, benzyl, 4-chlorobenzyl, 4-methylbenzyl and 4-methoxybenzyl, R.sub.1 is selected from hydrogen and hydroxy, R.sub.2 is selected from hydrogen, chlorobenzyl, dichlorobenzyl, .alpha.-cyclopropyl-dichloro-benzyl, dichlorophenyl-2-hydroxy-ethyl, dimethylbenzyl, trimethoxybenzyl, methylenedioxybenzyl, chlorophenylethyl, dichlorophenylethyl, chloro-iodo-phenylethyl, dimethoxyphenylethyl, methylenedioxyphenylethyl, trimethoxyphenylethyl, 3-phenylprop-2-yl, 3-phenyl-3-hydroxy-prop-2-yl, dichlorophenylpropyl, dichlorophenyl-3-hydroxyprop-2-yl, dichlorophenylbutyl and quinolin-4-ylmethyl, and R.sub.3 is selected from hydrogen and methyl, and salts thereof, have GABA.sub.B -antagonistic properties and can be used for the treatment of diseases responsive to GABA.sub.B -antagonists.Type: GrantFiled: November 19, 1992Date of Patent: December 27, 1994Assignee: Ciba-Geigy CorporationInventor: Stuart J. Mickel
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Patent number: 5369097Abstract: This invention pertains to the synthesis and use as therapeutic agents of a group of substances with a glycerol backbone or aliphatic chain structure linked to a phosphorus atom and a polar head group. Depending on the polar head group, the substance has anti-cancer, anti-inflammatory, anti-allergy or anti-cardiovascular disease properties. Compounds of the formula: ##STR1## wherein n is 0 to 14 and R.sub.1 is an alkyl group of C.sub.12 -C.sub.20, R.sub.2 is a methyl group, and wherein R.sub.3 is an inositol analog head group, a (CH.sub.2).sub.m N.sup.+ (CH.sub.3).sub.3 group with m=2 to 10, a serine head group, or an ethanolamine head group, or of the formula ##STR2## wherein R.sub.1 and R.sub.2 are as described above, n=0 or 1, and R.sub.3 is (CH.sub.2).sub.m N.sup.+ (CH.sub.3).sub.3 (m=2-10 ) are claimed.Type: GrantFiled: May 4, 1993Date of Patent: November 29, 1994Assignee: The University of British ColumbiaInventors: Hassan Salari, Robert Bittman
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Patent number: 5347030Abstract: Novel radioiodinated analogues of naturally-occurring phospholipid ethers are tumor-specific and have a triglycerol backbone structure which, in certain embodiments, is substituted at the 3-position with an alkyl phosphocholine and include a monoiodinated benzoyl side chain substituted at the 2-position in accordance with the general formula: ##STR1## where n= 1-15 ##STR2## m= 0-15; Z=.sup.123 I, .sup.125 I, and .sup.131 I; Y=NH.sub.2, NR.sub.2, and NR.sub.3, and R=alkyl, aralkyl.Type: GrantFiled: February 10, 1992Date of Patent: September 13, 1994Assignee: The Board of Regents of The University of MichiganInventors: Raymond E. Counsell, Karen L. Meyer, Susan W. Schwendner, Terushi Haradahira
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Patent number: 5344952Abstract: A method for enzyme immunoassay for a ligand suspected to be present in a liquid sample includes signal amplification by use of at least two enzymes and a blocked modulator for one of the enzymes. Ligand present in the liquid binds to an antiligand and an enzyme-labeled tracer. The resulting bound fraction is separated and the enzyme in the tracer removes the blocking group from the blocked modulator. The modulator activates or inhibits a second enzyme which catalyzes the conversion of a substrate to a product. The presence or absence of the ligand in the liquid is indicated by a signal, such as a color change or a rate of color change, associated with the product. The invention includes a new class of enzyme inhibitors and blocked inhibitors and a kit of materials useful for performing the method of the invention.Type: GrantFiled: March 22, 1993Date of Patent: September 6, 1994Assignee: Becton, Dickinson and CompanyInventors: Patrick D. Mize, James P. O'Connell
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Patent number: 5344930Abstract: Compounds of the general formula: ##STR1## are useful as surfactants in the preparation of fluorocarbon emulsions, which can be used as oxygen-carrying blood substitutes, and for many other therapeutic and diagnostic applications. They are further useful in liposomal formulations which are themselves therapeutic agents or provide a vehicle for such agents.Type: GrantFiled: November 8, 1993Date of Patent: September 6, 1994Assignee: Alliance Pharmaceutical Corp.Inventors: Jean G. Riess, Francois Jeanneaux, Marie-Pierre Krafft, Catherine Santaella, Pierre Vierling
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Patent number: 5329029Abstract: An efficient, technically straightforward and inexpensive process for generating conjugates of phospholipids with biologically important molecules is described.Type: GrantFiled: November 5, 1992Date of Patent: July 12, 1994Inventor: Barbara Y. Wan
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Patent number: 5326756Abstract: The present invention is directed to a new class of beta-ketone, beta oxime and beta hydrazine phosphonate NMDA antagonists.Type: GrantFiled: July 20, 1992Date of Patent: July 5, 1994Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Jeffrey P. Whitten, Bruce M. Baron
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Patent number: 5315023Abstract: A process for the preparation of highly pure deacylated glycerophosphorylcholine, glycerophosphorylethanolamine and glicerophosphorylserine starting from mixtures of the corresponding acylated derivatives.The process according to the invention is characterized in that the deacylation reaction, by means of alcoholysis, and the fractionation are carried out in a single step in a reactor containing a basic ion-exchange resin.Type: GrantFiled: March 8, 1993Date of Patent: May 24, 1994Assignee: Chemi S.p.A.Inventors: Lorenzo De Ferra, Fausto Bonifacio, Guido Cifarelli, Pietro Massardo, Oreste Piccolo
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Patent number: 5298499Abstract: Substituted phosphorothioate derivatives and pharmaceutical compositions thereof as potential antiradiation agents are disclosed.Type: GrantFiled: July 5, 1991Date of Patent: March 29, 1994Assignee: Research Triangle InstituteInventors: Frank I. Carroll, Philip Abraham
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Patent number: 5281747Abstract: P-substituted aminoalkylphosphinic acids of the formula ##STR1## wherein R denotes an optionally fluorinated methyl group, R.sub.1 denotes hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen or a fluorinated methyl group and R.sub.2 and R.sub.3 denote hydrogen or R.sub.2 denotes hydroxy, lower alkoxy or halogen and R.sub.3 is hydrogen or R.sub.2 and R.sub.3 together represent an oxo group, and their pharmaceutically acceptable salts are active as GABA.sub.B.sup.- agonists and can be used in the treatment of spinal spasticity, multiple sclerosis and cerebral palsy, trigeminus neuralgia, drug withdrawal syndromes and/or conditions of pain. They can be manufactured by methods known per se and suitable such methods are described.Type: GrantFiled: April 22, 1992Date of Patent: January 25, 1994Assignee: Ciba-Geigy CorporationInventors: Roger G. Hall, Ludwig Maier, Wolfgang Frostl
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Patent number: 5279833Abstract: A reagent for introducing a nucleic acid into an animal cell.Type: GrantFiled: April 4, 1990Date of Patent: January 18, 1994Assignee: Yale UniversityInventor: John K. Rose
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Patent number: 5274162Abstract: The composition, methods of synthesis, and applications of a new class of tumor selective antineoplastic drugs is described. These novel antineoplastic agents are of the general structure: A-C-B. The agents are designed with two key functionalities: a trigger which toxifies the drug; (A) and a deactivator which detoxifies the drug (B) The trigger is selected such that it is activated by an enzyme which is present in elevated levels in the tumor. The deactivator is selected such that it is actuated by an enzyme ubiquitous to all tissues. The fate of the drug in a given cell is then determined by the ratio of the enzymatic activity that triggers toxication to the enzymatic activity which detoxifies the drug. The partitioning of the drug between toxic metabolite and nontoxic metabolite defines the resulting specificity of cytotoxic effect.Type: GrantFiled: December 13, 1991Date of Patent: December 28, 1993Inventor: Arnold Glazier
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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: 5243062Abstract: The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1 -.sub.8 -alkyl, C.sub.3 -.sub.6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub.1 -.sub.4 -alkyl, C.sub.1 -.sub.4 -alkoxy and/or trifluoromethyl, or C.sub.7 -.sub.10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1 -.sub.4 -alkyl, C.sub.1 -.sub.4 -alkoxy and/or trifluormethyl, and the other two are hydrogen, or salts thereof.These compounds have valuable pharmaceutical properties.Type: GrantFiled: March 18, 1992Date of Patent: September 7, 1993Assignee: Ciba-Geigy CorporationInventors: John Gray Dingwall, Josef Ehrenfreund, Roger Graham Hall, James Jack
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Patent number: 5219845Abstract: The invention pertains to the synthesis and use as therapeutic agents of a group of substances with a glycerol backbone or aliphatic chain structure linked to a phosphorus atom and a polar head group. Depending on the polar head group, the substance has anti-cancer, anti-inflammatory, anti-allergy or anti-cardiovascular disease properties. Compounds of the formula: ##STR1## wherein n is 0 to 14 and R.sub.1 is an alkyl group of C.sub.12 -C.sub.20, R.sub.2 is a methyl group, and wherein R.sub.3 is an inositol analog head group, a (CH.sub.2).sub.m N.sup.+ (CH.sub.3).sub.3 group with m=2 to 10, a serine head group, or an ethanolamine head group, or of the formula ##STR2## wherein R.sub.1 and R.sub.2 are as described above, n=0 or 1, and R.sub.3 is (CH.sub.2).sub.m N.sup.+ (CH.sub.3).sub.3 (m=2-10) are claimed.Type: GrantFiled: February 11, 1992Date of Patent: June 15, 1993Assignee: The University of British ColumbiaInventors: Hassan Salari, Robert Bittman
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Patent number: 5215973Abstract: Monohydrate 1,2-di-O-acetyl-glycero-phosphoryl-choline in optically active and racemic form, processes for their preparation and pharmaceutical compositions containing them as the active principle for treating cerebral involutions of the aged and for treating dislipidemia and hyperlipoproteinemia.Type: GrantFiled: February 24, 1992Date of Patent: June 1, 1993Assignee: Magis Farmaceutici S.p.A.Inventor: Laura Puricelli
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Patent number: 5215976Abstract: There is provided longlasting contraceptives against human and animal sperm which contain a synthetic phospholipid spermicide of the formula: ##STR1## wherein: x=1 to 3 or mixtures thereof;x+y=3;z=x;a=0 to 2;B=0.sup.- or OM;A=Anion;M is a cation;R, R.sub.1 and R.sub.2 are the same or different and are alkyl, substituted alkyl, alkyl aryl or alkenyl groups of up to 16 carbon atoms with the proviso that the total carbon atoms in R+R.sub.1 +R.sub.2 is between 10 and 24; or ##STR2## wherein: x is as hereinabove defined;x+y=3;z=x;a=0 to 2;B=O.sup.- or OM;A is on Anion;M is a Cation;R.sub.3 is an amidoamine moiety of the formula: ##STR3## wherein: R.sub.7 is alkyl, alkenyl, alkoxy or hydroxyalkyl of from 5 to 21 carbon atoms each, or aryl or alkaryl of up to 20 carbon atoms;R.sub.6 is hydrogen or alkyl, hydroxyalkyl or alkenyl of up to 6 carbon atoms each or cycloalkyl of up to 6 carbon atoms, polyoxyalkylene of up to 10 carbon atoms;R.sub.4 and R.sub.Type: GrantFiled: June 19, 1992Date of Patent: June 1, 1993Assignee: Mona Industries, Inc.Inventors: Dennis L. Fost, Joseph A. Komor
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Patent number: 5208223Abstract: Phospocholine derivatives having the formula: ##STR1## in which W, Z, Q and R are described in the specification are disclosed as useful for inhibiting the enzyme phospholipase A.sub.2. Methods of making and using the compounds are also disclosed.Type: GrantFiled: June 3, 1992Date of Patent: May 4, 1993Assignee: American Cyanamid CompanyInventors: Allan Wissner, Robert E. Schaub, Kenneth E. Green, Philip R. Hamann
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Patent number: 5194166Abstract: Lubricant additives are produced by reacting an alkoxylated amine with phosphorous acid. The additives preferably also contain a boron moiety which is reacted with the phosphorous acid and amine, preferably in a one step reaction. More preferably, a mono-functional alcohol or a long-chain aliphatic carboxylic acid is added to this mixture. The additives are particularly useful in metal working oils and particularly as extreme pressure additives to replace the currently used chlorinated paraffin additives.Type: GrantFiled: July 10, 1992Date of Patent: March 16, 1993Assignee: The Elco CorporationInventors: Gerald D. Burt, Randolph A. McDonald
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Patent number: 5194654Abstract: Compounds are disclosed for treating viral infections due to herpes, influenza, hepatitis B, Epstein-Barr, and varicella zoster viruses, as well as cytomegalovirus and human immunodeficiency virus (HIV) by means of lipid derivatives of antiviral agents. The compounds consist of lipid derivatives of phosphonoacids having antiviral activity which are linked, commonly through the phosphate group of the phosphonoacid, to one of a selected group of lipids.The lipophilic nature of these compounds provides advantages over the use of the phosphonoacids alone. It also makes it possible to incorporate them into the lamellar structure of liposomes when combined with similar molecules. In the form of liposomes, these antiviral molecules are preferentially taken up by macrophages and monocytes, cells which have been found to harbor the target human immunodeficiency virus (HIV).Type: GrantFiled: November 22, 1989Date of Patent: March 16, 1993Assignee: Vical, Inc.Inventors: Karl Y. Hostetler, Raj Kumar
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Patent number: 5187292Abstract: The invention relates to an N-sulfomethylglycinate of formula:HO.sub.3 S--CH.sub.2 --NH--CH.sub.2 --COOR.sub.1 (I)COOR.sub.1 being a hydrolysable carboxylic ester group.It also relates to a process for the preparation of the compound of formula (I) consisting in putting in contact sulfur dioxide, formaldehyde, and glycine in the presence of a R.sub.1 OH alcohol, or glycinate.It also relates to the use of the compound of formula (I) for the preparation of herbicides of the glyphosate type of reaction with a phosphite or a phosphonate of formula (R.sub.2 O).sub.2 P (O) H in which (R.sub.2 O).sub.2 P is a hydrolysable phosphonic ester group, then optionally by a subsequent hydrolysis reaction.Type: GrantFiled: March 2, 1992Date of Patent: February 16, 1993Assignee: Rhone-Poulenc AgrochimieInventors: Bernard Botannet, Jean-Louis Clavel, Jean-Pierre Corbet, Michel Mulhauser
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Patent number: 5179085Abstract: N-substituted .alpha.-amino acids and derivatives thereof are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful in selectively blocking the N-methyl-D-aspartate (NMDA) excitatory amino acid receptors in mammals and also are useful in treating cerebrovascular disorders such as cerebral ischemia or cerebral infarction resulting from thromboembolic or hemorrhagic stroke, cerebral vasospasm, hypoglycemia, cardiac arrest, status epilepticus and cerebral trauma as well as for treating schizophrenia, epilepsy, neurodegenerative disorders, Alzheimer's disease or Huntington's disease and also additionally useful as anesthetics in surgical procedures where a finite risk of cerebrovascular damage exists.Type: GrantFiled: April 22, 1991Date of Patent: January 12, 1993Assignee: Warner-Lambert CompanyInventors: Christopher F. Bigge, Graham Johnson
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Patent number: 5158942Abstract: The present invention is concerned with the use of compounds of the general formula: ##STR1## and of the pharmacologically acceptable salts thereof, as well as of the optical isomers thereof for the preparation of pharmaceutical compositions with antiviral action.The present invention also provides new phospholipid derivatives.Type: GrantFiled: August 23, 1990Date of Patent: October 27, 1992Assignee: Boehringer Mannheim GmbHInventors: Dieter Herrmann, Elmar Bosies, Harald Zilch, Edith Koch
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Patent number: 5155099Abstract: Compounds of formula I ##STR1## in which R denotes a straight-chain or branched, saturated or unsaturated aliphatic hydrocarbon radical having 6-30 C atoms wich may optionally be substituted by halogen or the radicals OR.sub.1, SR.sub.1 or NR.sub.1 R.sub.2, where R.sub.1 and R.sub.2 in each case denote a hydrogen atom or an alkyl or acyl radical having 1-6 C atoms which have excellent virustatic and cytostatic action.Type: GrantFiled: October 19, 1990Date of Patent: October 13, 1992Assignee: Hafslund Nycomed Pharma AktiengesellschaftInventors: Hans Brachwitz, Reinhild Schonfeld, Peter Langen, Friedrich Paltauf, Albin Hermetter
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Patent number: 5147867Abstract: Dipeptide mimics which contain phosphorus and their pharmaceutical use and preparation are disclosed. The compounds have dehydropeptidase (DHP) enzyme inhibitor activity.Type: GrantFiled: January 21, 1992Date of Patent: September 15, 1992Assignee: Merck & Co., Inc.Inventors: William H. Parsons, William R. Schoen, Arthur A. Patchett
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Patent number: 5144045Abstract: Phospocholine derivatives having the formula: ##STR1## in which W, Z, Q and R are described in the specification are disclosed as useful for inhibiting the enzyme phospholipase A.sub.2. Methods of making and using the compounds are also disclosed.Type: GrantFiled: November 13, 1990Date of Patent: September 1, 1992Assignee: American Cyanamid CompanyInventors: Allan Wissner, Robert E. Schaub, Kenneth E. Green, Philip R. Hamann
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Patent number: 5138020Abstract: PBZ polymers are synthesized by the reaction of AA- and BB-monomers. The BB-monomer is conveniently synthesized and isolated as a phosphate salt having a uniform number of phosphate ions associated with each BB-monomer ion. Such high purity monophosphate and diphosphate salts can be obtained by precipitating the monomer from an aqueous acid solution by adjusting the pH balance or from a mixture of phosphoric acid and a volatile, polar, saturated organic liquid at a relatively low temperature.Type: GrantFiled: April 21, 1989Date of Patent: August 11, 1992Assignee: The Dow Chemical CompanyInventors: William J. Harris, Ming-Biann Liu, Luke R. Kleiss, Zenon Lysenko, Steven Rosenberg
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Patent number: 5118674Abstract: The invention relates to 3-(N-methyl-N-alkyl)-amino 2-methoxymethylene propan 1-ol derivatives of the formula ##STR1## wherein R stands for an alkyl chain, A stands for: ##STR2## and Y represents various quaternary ammonia, to a preparation process of said compounds and to therapeutic compositions containing the same.Type: GrantFiled: November 27, 1990Date of Patent: June 2, 1992Assignee: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)Inventors: Pierre Braquet, Colette Broquet, Benedicte Vandamme, Paola Principe-Nicolas