Nitrogen, Sulfur, Phosphorus, Or Peroxy Attached Directly To The Acyclic Carbon By Nonionic Bonding Patents (Class 552/104)
  • Patent number: 7115769
    Abstract: Non-natural amino acids such as 2-alkylated amino acids allow for the synthesis of a wider variety of peptidal and non-peptidal pharmaceutically active agents. In one embodiment, the present invention provides methods of preparing 2-alkylcysteine derivatives. In another embodiment, the method comprises forming a 2-alkylcysteine derivative from a cysteine derivative in the presence of a phase transfer catalyst. In particular, the present invention provides methods for preparing 2-methylcysteine derivatives. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In one aspect, an aryl nitrile or imidate is condensed with cysteine or a 2-alkyl cysteine. The present invention also relates to the preparation of 4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-alkyl-thiazole-4-carboxylic acids, such as 4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-methyl-thiazole-4-carboxylic acid.
    Type: Grant
    Filed: May 15, 2003
    Date of Patent: October 3, 2006
    Assignee: Genzyme Corporation
    Inventors: Rayomand H. Gimi, Mukund S. Chorghade
  • Publication number: 20040087807
    Abstract: This invention relates to attachment chemistries for binding macromolecules to a substrate surface or to other conjugation targets. More particularly, this invention relates to attachment chemistries involving branched or linear structures having one or more hydrazide attachment moieties for binding the macromolecules to a substrate surface, or for other conjugation reactions. Novel modifying reagents are provided for the introduction of protected hydrazide attachment moieties or precursor forms of such hydrazides to the macromolecule, either as a single hydrazide or as multiple hydrazides.
    Type: Application
    Filed: August 15, 2003
    Publication date: May 6, 2004
    Inventors: Stefan Raddatz, Jochen Muller-Ibeler, Markus Schweitzer, Christoph Brucher, Norbert Windhab, John r. Havens, Thomas J. Onofrey, Charles H. Greef, Daguang Wang
  • Patent number: 6713641
    Abstract: Disclosed are blue, diol anthraquinone blue colorant compounds having excellent thermal stability and which can be reacted into or copolymerized with polyester thus providing a blue-colored polyesters useful for manufacturing a variety of shaped articles such as photographic film base, particularly roentgenographic (X-ray) film. Also disclosed are blue anthraquinone colorant compounds which contain two ethylenically-unsaturated (vinyl), photopolymerizable radicals which may be derived from the aforesaid diol anthraquinone compounds. The anthraquinone colorant compounds containing two ethylenically-unsaturated may be reacted into or copolymerized (or cured) with ethylenically-unsaturated monomers to produce colored vinyl polymers.
    Type: Grant
    Filed: October 19, 2001
    Date of Patent: March 30, 2004
    Assignee: Eastman Chemical Company
    Inventors: Max Allen Weaver, Gerry Foust Rhodes, Jason Clay Pearson, Sara Stanley Wells, Michael John Cyr
  • Publication number: 20030219662
    Abstract: Charge transport compounds are described that have a multiple number of hydrazone-bridged heterocyclic groups (especially julolidine groups, carbazole groups, triarylamine groups and (N,N-disubstituted)arylamine groups such as dialkarylamine groups (e.g. dimethylphenylamine; methylethylphenylamine, dipropylphenylamine, ethylepropylphenylamine, ethylbutylnaphthylamine, etc.), alkyldiarylamine groups (e.g. methyldiphenylamino, ethyldiphenylamino, etc), and triarylamino groups (e.g., triphenyl amino, trinaphthylamino, etc)) connected by a central bridging group.
    Type: Application
    Filed: May 30, 2003
    Publication date: November 27, 2003
    Applicant: SAMSUNG Electronics Co. Ltd.
    Inventors: Nusrallah Jubran, Zbigniew Tokarski, Kam Law, Vytautas Getautis, Jonas Sidaravicius, Osvaldas Paliulis, Valentas Gaidelis, Vygintas Jankauskas
  • Publication number: 20030129513
    Abstract: Charge transport compounds are described that have a multiple number of hydrazone-bridged heterocyclic groups (especially julolidine, carbazole and/or triarylmethane groups) connected by a central bridging group.
    Type: Application
    Filed: September 24, 2001
    Publication date: July 10, 2003
    Applicant: Samsung Electronics Co., Ltd.
    Inventors: Nusrallah Jubran, Hwan Koo Lee, Kam W. Law
  • Patent number: 6492515
    Abstract: The present invention relates to benzoxazinones of formula I: or stereoisomeric forms or mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HIV reverse transcriptase, and to pharmaceutical compositions and diagnostic kits comprising the same, methods of using the same for treating viral infection or as an assay standard or reagent, and intermediates and processes for making the same.
    Type: Grant
    Filed: July 31, 2001
    Date of Patent: December 10, 2002
    Assignee: Bristol-Myers Squibb Pharma Company
    Inventors: Joseph Marian Fortunak, Mona Patel
  • Publication number: 20010014747
    Abstract: Novel triphenylmethane dyes or colorants with sterically hindered fugitive amine counter ions are provided as durable, storage-stable, and excellent coloring and shading printing inks. Ink compositions are disclosed which provide improvements in long-term storage capabilities, particularly within alkaline environments, extremely effective colorations of cellulose-based substrates, and lower cost over those of the prior art. The preferred dyes or colorants are triphenylmethane polymeric colorants which are capped with cyclic anhydride and the preferred sterically hindered amine counter ions are those based on low molecular weight fugitive tertiary amines, such as N,N-dimethylethanolamine. Compositions comprising water soluble or emulsion resins as diluents for lowered viscosity and lower overall cost are also contemplated. Furthermore, compositions comprising the inventive colorant and other pigments, dyes, surfactants, preservatives, and other colorants are contemplated.
    Type: Application
    Filed: April 12, 2001
    Publication date: August 16, 2001
    Inventor: Philip G. Harris
  • Patent number: 6166229
    Abstract: Amino acids are derivatized for use in peptide synthesis by conversion to N-carboxyanhydrides that are N-protected by either a trityl or a phenylfluorenyl group.
    Type: Grant
    Filed: April 24, 2000
    Date of Patent: December 26, 2000
    Assignee: The Regents of the University of California
    Inventors: Henry Rapoport, Tae Bo Sim
  • Patent number: 5981778
    Abstract: A method of producing an ether-type thio-phospholipid of the formula (I): ##STR1## wherein: n is an integer of 13 to 17;A is C.sub.14 -C.sub.20 acyl group;G is a group selected from the group consisting of: ##STR2## which is useful as synthetic substrate of cytosolic phospholipase A.sub.2 inhibitors, said method being applicable to mass production of the compound (I), intermediates therefor and the preparation of the same are provided.
    Type: Grant
    Filed: March 23, 1998
    Date of Patent: November 9, 1999
    Assignee: Shionogi & Co., Ltd.
    Inventors: Mitsuaki Ohtani, Masahiro Fuji
  • Patent number: 5922890
    Abstract: New trityl linkers for use in solid phase synthesis comprise compounds of formula II ##STR1## wherein R.sub.4 is alkyl (e.g. C.sub.1-4 alkyl), halogen, NO.sub.2, or hydrogen;Z is a coupling group chosen from acylamido, acyloxy, amino, halogen, thiol or hydroxyl,where acyl is the residue of a carboxylic acid or a residue of formula R.sub.5 CO where R.sub.5 is an organic group;Y is H, a reactive functional group or an attachment to a solid phase;W is O when Y is H or a reactive functional group, or W is --NH--, or --NR.sub.6 --(urethane) when Y is an attachment to a solid phase,where R.sub.6 is an organic group and,each R which, may be the same or different, is C(O)NR.sub.7 R.sub.8, CF.sub.3, F or Cl wherein each R.sub.7 and R.sub.8, which may be the same or different, is H or C.sub.
    Type: Grant
    Filed: December 3, 1997
    Date of Patent: July 13, 1999
    Assignee: Novartis AG
    Inventor: Konrad Bleicher
  • Patent number: 5849945
    Abstract: The present invention pertains to a process for the preparation of Compound (4) through the below-described reaction route: ##STR1## wherein R.sup.1 and R.sup.2 each represents H, halogen, OH or C.sub.1-6 alkyl group; X and Y each represents a protected amino group and n stands for 0 to 4. According to the above process, an aminotetralone derivative which is an intermediate useful for an industrial preparation of a camptothecin derivative can be obtained in a convenient manner and in a high yield.
    Type: Grant
    Filed: August 21, 1997
    Date of Patent: December 15, 1998
    Assignees: Daiichi Pharmaceutical Co., Ltd., Kabushikikaisha Yakult Honsha
    Inventors: Shinji Kamihara, Kazuaki Kanai, Shigeru Noguchi
  • Patent number: 5712418
    Abstract: The present invention is directed to the process of preparing a peptide comprising reacting a first amino acid or peptide with an amino acid fluoride of the formula: ##STR1## or the acid fluoride salts thereof wherein BLK is an N-amino protecting groupAA is an amino acid residue andX is H or a protecting group useful,and the first amino and peptide have a free amino group and a blocked carboxy end.
    Type: Grant
    Filed: August 2, 1994
    Date of Patent: January 27, 1998
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Ayman Ahmed El-Faham
  • Patent number: 5554773
    Abstract: 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: Grant
    Filed: May 12, 1995
    Date of Patent: September 10, 1996
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Jeffrey P. Whitten, Duane E. Rudisill
  • Patent number: 5455363
    Abstract: Compounds of formula I are described, ##STR1## wherein n is equal to one or two, R.sub.1 stands for hydrogen or an amino protecting group, R.sub.2 represents hydrogen or a carboxyl protecting group and R.sub.3 4-methyltriphenylmethyl, 4,4'-dimethyltriphenylmethyl, 4,4',4"-trimethyltriphenylmethyl. Furthermore described are compounds of formula I which are reactive and suitable for coupling reactions and are derived from I with R.sub.2 =H by activation of the carboxyl group.The compounds mentioned above can be used as starting materials for the synthesis of peptides. They are more suitable than analogous compounds of formula I, wherein R.sub.3 represents hydrogen or a carbamoyl protecting group used hitherto.
    Type: Grant
    Filed: October 7, 1992
    Date of Patent: October 3, 1995
    Inventors: Jacques Gosteli, Beat Sax, Fritz Dick, Rudolf Tanner
  • Patent number: 5420330
    Abstract: 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: Grant
    Filed: September 7, 1990
    Date of Patent: May 30, 1995
    Assignee: Pharmacia P-L Biochemicals Inc.
    Inventor: Charles K. Brush
  • Patent number: 5360928
    Abstract: A compound of the formula ##STR1## or the acid fluoride salts thereof wherein BLK is an N-amino protecting group or hydrogenAA is an amino acid residue andX is H or a protecting group useful as a coupling agent in peptide synthesis.
    Type: Grant
    Filed: October 23, 1989
    Date of Patent: November 1, 1994
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Dean Sadat-Aalaee
  • Patent number: 5324833
    Abstract: Compounds of the formula I, ##STR1## in which 'R.sub.1 is an amino protective group, and n stands for 1 or 2, R.sub.1 denotes hydrogen or an amino protective group, R.sub.2 denotes hydrogen or a carboxyl protective group and R.sub.3 denotes triphenylmethyl, 4-monomethoxy-trityl or 4,4'-dimethoxy-trityl, and reactive carboxylic acid derivatives of such compounds of the formula I in which R.sub.2 stands for hydrogen, are described.These compounds can be used as starting materials for the preparation of peptides. They are more suitable for this than are analogous compounds of the formula I in which R.sub.3 denotes hydrogen or one of the carbamoyl protective groups hitherto customary.
    Type: Grant
    Filed: April 13, 1990
    Date of Patent: June 28, 1994
    Assignee: Novabiochem AG
    Inventors: Peter Sieber, Bernhard Riniker
  • Patent number: 5233048
    Abstract: Color formers of the general formula ##STR1## in which --independently of one another-- R.sup.1 and R.sup.2 are hydrogen, halogen, alkyl, aralkyl etc.,Y.sup.1 and Y.sup.2 are alkyl, aryl, cycloalkyl or aralkyl,X.sup.1 is alkyl, alkenyl, cycloalkyl, aralkyl etc.,X.sup.2 is H, alkyl, alkenyl, cycloalkyl etc.X.sup.1 with X.sup.2 with the inclusion of the nitrogen atom carrying them can form a saturated or unsaturated 5- or 6-membered heterocyclic ring, andfurther isocyclic or heterocyclic rings can be fused with the rings A, B and C, upon incorporation in recording materials based on acid developers, show a particularly advantageous migration behaviour. Deep blue, green-blue, green, violet or red shades which have excellent sublimation and light fastness are obtained.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: August 3, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Eckstein, Roderich Raue
  • Patent number: 5189188
    Abstract: Compounds of the general formula ##STR1## in which the symbols have the meaning given in the description, are highly suitable as color formers in recording materials based on acid developers. They give deep blue, green-blue, green, violet or red shades which have excellent sublimation and light fastness.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: February 23, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Udo Eckstein
  • Patent number: 5130447
    Abstract: An improvement is described in the synthesis method for N.sup..alpha. -trityl-N.sup.G -trityl arginine within a process for preparing N.sup..alpha. -fluorenylmethoxycarbonyl-N.sup.G -trityl-arginine from arginine, comprising:a) forming N.sup..alpha. -trityl-N.sup.G -trityl-arginineb) selectively detaching the trityl group from the .alpha.-NH.sub.2 andc) introducing the fluorenylmethoxycarbonyl group in its place.The improvement consists of preparing the N.sup..alpha. -trityl-N.sup.G -trityl-arginine by solubilizing the arginine in an aprotic organic solvent by tri-alkylsilylation both of the amino nitrogen and of the carboxyl group, followed by tritylation, with trityl chloride, of the .alpha.-amino nitrogen, and of the guanidino group after deprotonating this latter with a bicyclic guanidine. The new improved process can also lead to variable quantities of the arginine analogue di-tritylated at the guanidino group, namely N.sup..alpha. -fluorenylmethoxycarbonyl-N.sup.G -di-trityl-arginine.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: July 14, 1992
    Assignee: Sclavo S.p.A.
    Inventors: Valerio Caciagli, Antonio S. Verdini
  • Patent number: 5112996
    Abstract: A method is described for substituting at least one hydrogen atom originally present in the guanidino group of a compound of general formula (I) ##STR1## where R is any substituted or unsubstituted residue, by a group R.sub.1 where R.sub.1 is an unsubstituted or substituted, linear or branched alkyl, consisting of:a) silylating the guanidino group and any other silylatable functional groups present within the R group andb) alkylating the product obtained in step a) with a mixture consisting of the alkyl halide R.sub.1 -X and an organic base containing a tertiary nitrogen.
    Type: Grant
    Filed: August 28, 1990
    Date of Patent: May 12, 1992
    Assignee: Sclavo S.p.A.
    Inventor: Valerio Caciagli
  • Patent number: 5081284
    Abstract: A novel N-substituted peptidyl compound represented by the general formula (1): ##STR1## where R.sub.1 is a straight-chained or branched acyl group having 2-10 carbon atoms, a branched, cyclic or partly branched cyclic alkyloxycarbonyl group having 4-15 carbon atoms, a substituted or unsubstituted benzyloxycarbonyl group, a 2,2,2-trichloroethyloxycarbonyl group, a 2-(trimethylsilyl)ethyloxycarbonyl group, a p-toluensulfonyl group, an o-nitrophenylsulfenyl group, a diphenylphosphonothioyl group, a triphenylmethyl group, a 2-benzoyl-1-methylvinyl group or a 4-phenylbutyryl group; R.sub.2 is a hydrogen atom or when taken together with R.sub.1, may form a phthaloyl group; R.sub.3 is an isobutyl group, a n-butyl group or an isopropyl group; R.sub.4 is a butyl group, a benzyl group or a methylthioethyl group; and R.sub.5 is a hydrogen atom or a chloromethyl group, which inhibits the activity of cysteine proteinases.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: January 14, 1992
    Assignee: Suntory Limited
    Inventors: Naoki Higuchi, Masayuki Saitoh, Norio Iwasawa, Motoo Sumida, Hiroshi Shibata
  • Patent number: 5079375
    Abstract: An improvement is described in the synthesis method for N.sup..alpha. -trityl-N.sup.G -trityl arginine within a process for preparing N.sup..alpha. -fluorenyl-methoxycarbonyl-N.sup.G -trityl-arginine from arginine, comprising:a) forming N.sup..alpha. -trityl-N.sup.G -trityl-arginineb) selectively detaching the trityl group from the .alpha.-NH.sub.2 andc) introducing the fluorenylmethoxycarbonyl group in its place.The improvement consists of preparing the N.sup..alpha. -trityl-N.sup.G -trityl-arginine by solubilizing the arginine in an aprotic organic solvent by tri-alkylsilylation both of the amino nitrogen and of the carboxyl group, followed by tritylation, with trityl chloride, of the .alpha.-amino nitrogen, and of the guanidino group after deprotonating this latter with a bicyclic guanidine. The new improved process can also lead to variable quantities of the arginine analogue di-tritylated at the guanidino group, namely N.sup..alpha. -fluorenylmethoxycarbonyl-N.sup.G -di-trityl-arginine.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: January 7, 1992
    Assignee: Sclano S.p.A.
    Inventors: Valerio Caciagli, Antonio S. Verdini
  • Patent number: 5023325
    Abstract: A reactive dye of the formulaD--U--R).sub.nin which D is the radical of an anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; U is --CO-- or --SO.sub.2 --; R is a radical of the formula ##STR1## Z is sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-acetoxyethyl, .beta.-halogenoethyl or vinyl; alk is a polymethylene radical having 1 to 6 C atoms or its branched isomers; Y is hydrogen, chlorine, bromine, fluorine, hydroxyl, sulfato, C.sub.1 -C.sub.4 -alkanoyloxy, cyano, carboxyl, alkoxycarbonyl having 1 to 5 C atoms, carbamoyl or a radical --SO.sub.2 --Z in which Z is as defined above; V is hydrogen or C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by carboxyl, sulfo, C.sub.1 -C.sub.2 -alkoxy, halogen or hydroxyl;or a radical ##STR2## in which Z, alk and Y are as defined above; R.sub.1 is hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: May 11, 1988
    Date of Patent: June 11, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Peter Aeschlimann
  • Patent number: 4914210
    Abstract: Oligonucleotide functionalizing reagents are disclosed which are useful in introducing sulfhydryl, amino and additional hydroxyl groups into oligonucleotides. The reagents are substantially linear in structure, at one end provided with a phosphoramidite moiety, at an opposing end provided with a sulfhydryl, amino or hydroxyl moiety, the two ends linked through a hydrophilic spacer chain. Methods of using and synthesizing the novel reagents are disclosed as well.
    Type: Grant
    Filed: October 2, 1987
    Date of Patent: April 3, 1990
    Assignee: Cetus Corporation
    Inventors: Corey Levenson, Chu-An Chang, Fred T. Oakes