Patents Examined by Johnnie R. Brown
  • Patent number: 5294701
    Abstract: This invention provides novel anti-tumour compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or together form an alkyl-, alkoxy- or OH-substituted aromatic group, which optionally contains an N atom as a hetero-atom; R is --COCH.sub.3 or --C.tbd.C--R.sub.4 and R.sub.4 is H or trimethylsilyl; and R.sub.3 is H or --COCF.sub.3 ; and acid addition salts thereof; as well as compositions containing these compounds.
    Type: Grant
    Filed: May 6, 1992
    Date of Patent: March 15, 1994
    Assignee: Pharmachemie B.V.
    Inventors: Johan W. Scheeren, Joannes F. M. de Bie, Dirk de Vos
  • Patent number: 5292873
    Abstract: A sequence directed reagent is constructed by conjugating a methyl naphthoquinone derivative to a hexamethylamino linker attached to the 5' terminus of an oligonucleotide. Annealing this modified fragment of DNA to its complementary sequence allows for target modification subsequent to photochemical activation. The product of this reaction is a covalent crosslink between the reagent and target strands resulting from an alkylation of DNA by the photoexcited quinone. The modified sequence is not labile to acid, base or reductants, and blocks the exonuclease activity of the Klenow fragment of DNA polymerase I. In another embodiment, a highly reactive moiety, such as Br is attached to the methyl group of the naphthoquinone derivative. This reagent is similarly linked to an oligonucleotide probe. Activation of this probe linked alkylating agent is by a reductive signal which may either naturally occur within the cell, such as an enzyme, or introduced into the media containing the target molecule.
    Type: Grant
    Filed: November 29, 1989
    Date of Patent: March 8, 1994
    Assignee: The Research Foundation of State University of New York
    Inventors: Steven E. Rokita, Moneesh Chatterjee
  • Patent number: 5292498
    Abstract: A method of hydrating mucous secretions in the lungs of a subject in need of such treatment is disclosed. The method comprises administering to the lungs of the subject a uridine triphosphate such as uridine 5'-triphosphate (UTP) or uridine 5'-O-(3-thiotriphosphate) (UTP.gamma.S) in an amount effective to hydrate lung mucous secretions. The method is useful for treating patients aflicted with cystic fibrosis. Pharmaceutical formulations and methods of making the same are also disclosed.
    Type: Grant
    Filed: June 19, 1991
    Date of Patent: March 8, 1994
    Assignee: The University of North Carolina At Chapel Hill
    Inventor: Richard C. Boucher, Jr.
  • Patent number: 5290927
    Abstract: A process for preparing 2',3'-dideoxyadenosine of the formula ##STR1## wherein B is adenine, wherein R.sup.1 is hydrogen, C.sub.1-12 acyl, C.sub.1-12 alkyl, C.sub.7-8 aralkyl, or silyl, said process comprising:reducing a nucleoside of the formula IIIa or IIIb ##STR2## wherein R.sup.2 is hydrogen, C.sub.1-12 acyl, C.sub.1-12 alkyl, C.sub.7-8 aralkyl or silyl; X is Cl, Br or I; R.sup.5 is C.sub.1-12 acyl and B is adenine, with hydrogen in the presence of a palladium catalyst and aqueous solvent mixture of acetonitrile or ethyl acetate and water, said aqueous solvent containing a base selected from the group consisting of sodium hydroxide/sodium acetate and sodium carbonate/sodium acetate, wherein said solvent has a pH of 9-11.
    Type: Grant
    Filed: March 1, 1989
    Date of Patent: March 1, 1994
    Assignee: Ajinomoto Co., Inc.
    Inventors: Yutaka Honda, Hiroshi Shiragami, Hisao Iwagami, Masayuki Arai
  • Patent number: 5288859
    Abstract: A process for stereospecific preparation of glycosyl azides by reacting a metal azide with a glycosyl phosphate triester having the phosphate group cis to the adjacent C-2 substituent is disclosed.
    Type: Grant
    Filed: January 22, 1991
    Date of Patent: February 22, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Subramaniam Sabesan
  • Patent number: 5288710
    Abstract: Certain salts of 4"-deoxy-4"-epi-methylamino avermectin Bla/Blb such as: the benzoic acid salt, gallic acid salt, citric acid salt, benzenesulfonic acid salt and salicyclic acid salt, phosphoric acid salt, tartaric acid salt or maleic acid salt, exhibit enhanced stability, a property which serves to provide greater shelf life and a product of greater safety for the user and the environment.
    Type: Grant
    Filed: April 2, 1992
    Date of Patent: February 22, 1994
    Assignee: Merck & Co., Inc.
    Inventor: Raymond Cvetovich
  • Patent number: 5288709
    Abstract: New 9-deoxo-9,12-epoxy erythromycin derivatives are disclosed which have improved antibacterial properties. Compositions comprising the erythromycin derivatives and methods of treating mammalian patients with the erythromycin derivatives are also disclosed.
    Type: Grant
    Filed: August 21, 1991
    Date of Patent: February 22, 1994
    Assignee: Abbott Laboratories
    Inventors: Leslie A. Freiberg, Larry L. Klein, Clinton M. Yeung, Carla M. Edwards, David J. Bacino
  • Patent number: 5284834
    Abstract: This invention comprises a series of N.sup.6 -substituted adenosine analogues bearing functionalized chains for the covalent attachment to probes or solid supports. In these compounds coronary vasodilation in the open thorax dog model, typical of A.sub.2 -adenosine receptor agonists, is shown. The potency is modulated by distal structural changes in the chain, with the highest A.sub.2 -potency observed for two methylamides, a primary amine congener, and a biotin conjugate. These compounds have antihypertensive activity and certain components are charged and are excluded from crossing the blood-brain barrier.
    Type: Grant
    Filed: August 6, 1992
    Date of Patent: February 8, 1994
    Assignee: The United States of America as represented by the Secretary of the Department of Health and Human Services
    Inventors: Kenneth A. Jacobson, Kenneth L. Kirk, John W. Daly
  • Patent number: 5283328
    Abstract: The present invention relates to compounds of the formula I[CH.sub.3 --(CH.sub.2).sub.29 --O--].sub.m --R (I)whereinif m stands for 1, thenR represents a group derived from a mono- or di- or oligosaccharide by removing the hydrogen atom from the hydroxyl group being in the 1(alpha) or 1(beta) position, or the O-protected, preferably acetylated derivative thereof,if m stands for 2, thenR represents a group derived by removing a hydrogen atom attached to the carbon atom being in position 1 of the reaction product of glucose and mono-, di- or triethylene glycol or the O-protected, preferably O-acetylated derivative thereof.
    Type: Grant
    Filed: October 11, 1994
    Date of Patent: February 1, 1994
    Assignee: Biogal Gyogyszergyar Rt.
    Inventors: Antal Kovacs, Andras Liptak, Pal Nanasi, Zoltan Szurmai, Istvan Csernus, Katalin Marossy, Katalin Kovacs-Hadadi, Zsuzsa Emri-Harsi, Ildiko Gombos-Nemeti
  • Patent number: 5283327
    Abstract: The present invention relates to a novel compound represented by the following formula [I] which is useful as a synthetic intermediate of a 2-alkynyladenosine.The present invention also relates to a process for producing the compound and a process for producing a 2-alkynyladenosine [IV] by way of the compound.Further, the present invention relates to a 2-alkynyladenosine derivative represented by the following formula [V] having excellent storage stability and, to a method of storing the 2-alkynyladenosine in the form of that derivative. ##STR1## wherein R.sup.1 through R.sup.4 represent a hydrogen atom or a protective group, and n denotes an integer of 1 to 15, provided that R.sup.1 through R.sup.4 do not represent a hydrogen atom simultaneously.
    Type: Grant
    Filed: April 17, 1991
    Date of Patent: February 1, 1994
    Assignees: Yamasa Shoyu Kabushiki Kaisha, Toa Eiyo Ltd.
    Inventors: Toyofumi Yamaguchi, Toichi Abiru, Akira Matsuda, Tohru Ueda, Kentaro Kogi
  • Patent number: 5283353
    Abstract: The invention resides in oligosaccharide derivatives which are obtained by the enzynmatic cleavage of carbohydrates linked to proteins through asparagine groups. The oligosaccharide moieties of the instant invention are 1-amino-1-deoxyoligosaccharide compounds which are cleaved from a glycoprotein with an aminohydrolase enzyme, wherein the amino group of the oligosaccharide is subsequently substituted with a fluorescent reporter compound. The compounds of the instant invention are characterized by the glycosylamine bonds exhibiting less than 10% hydrolysis at 25.degree. C. in aqueous solution over a two days at pH values between 4-10.
    Type: Grant
    Filed: June 5, 1990
    Date of Patent: February 1, 1994
    Assignees: Genzyme Corporation, Purdue Research Foundation
    Inventors: James R. Rasmussen, John M. Risley, Robert L. Van Etten
  • Patent number: 5281527
    Abstract: This invention provides a pullulanase having a high degree of pH stability under acidic conditions, which is produced by cultivation of a microorganism belonging to the genus Bacillus, particularly Bacillus circulans SV-98 (FERM P-12161). This enzyme is useful, for example, in the manufacture of glucose and maltose from starch.
    Type: Grant
    Filed: June 23, 1992
    Date of Patent: January 25, 1994
    Assignee: Nagase Biochemicals, Ltd.
    Inventors: Yoshihisa Tachibana, Iwao Kojima, Ritsuko Yoshida, Tomoko Adachi, Yoshiaki Takesada, Saburo Yamauchi
  • Patent number: 5281701
    Abstract: A method and compositions are provided for synthesizing polynucleotides wherein the exocyclic amino groups of 5'-O-protected-2'O-alkylsilyl-adenosine phosphoramidite and 5'-O-protected-2'-O-alkylsilylguanosine phosphoramidite monomers are protected with dialkylformamidine. In a preferred embodiment, the ribonucleoside phosphoramidite monomers are activated with ethylthiotetrazole.
    Type: Grant
    Filed: July 12, 1991
    Date of Patent: January 25, 1994
    Assignee: Applied Biosystems, Inc.
    Inventor: Ravi S. Vinayak
  • Patent number: 5280015
    Abstract: The present invention is directed to compounds useful as probes for characterizing and studying the adenosine A.sub.2 receptor. The present invention is also directed to methods of treating central nervous system disorders and cardiovascular disorders which include treating hypertension and thrombosis by administering said compounds.
    Type: Grant
    Filed: September 5, 1990
    Date of Patent: January 18, 1994
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Kenneth A. Jacobson, R. Tyler McCabe, Phil Skolnick
  • Patent number: 5278150
    Abstract: The present invention discloses a compound of the formula: ##STR1## where R.sub.1 is hydrogen or the group ##STR2## where R.sub.3 and R.sub.4 are the same or different and are hydrogen, C.sub.1 to C.sub.12 linear or branched alkyl, C.sub.3 to C.sub.7 cycloalkyl, C.sub.6 to C.sub.10 aryl unsubstituted or substituted with C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched alkoxy, nitro, amino, amino substituted with at least one C.sub.1 to C.sub.6 linear or branched alkyl or phenyl, C.sub.2 to C.sub.10 aralkyl, C.sub.4 to C.sub.8 heteroaryl wherein said heteroatom is nitrogen, phosphorous, sulfur or oxygen, and R.sub.2 is hydrogen, or taken together with R.sub.5, forms a chemical bond, and R is a monosaccharide radical selected from the group consisting essentially of glucose, fructose, ribose, 2-deoxyribose, mannose, galactose, xylose and arabinose.
    Type: Grant
    Filed: April 24, 1992
    Date of Patent: January 11, 1994
    Assignee: Whitby Research, Inc.
    Inventors: Ray A. Olsson, Robert D. Thompson
  • Patent number: 5278300
    Abstract: 4,6-O-hydroxyphosphoryl-glucosamine derivatives as shown in the following formula [I] and their pharmaceutically-acceptable salts: ##STR1## wherein R.sub.1 and R.sub.2 represent a hydrogen atom or a hydroxy group; one of R.sub.3 and R.sub.4 represents --OCO(CH.sub.2).sub.n CH.sub.3, --CH.sub.2 (CH.sub.2).sub.n CH.sub.3, or --O--CH.sub.2 (CH.sub.2).sub.n CH.sub.3, and the other represents a hydrogen atom; l is an integer of 4-16; m is an integer of 4-16; and n is an integer of 6-18.
    Type: Grant
    Filed: December 12, 1991
    Date of Patent: January 11, 1994
    Assignees: Japan Tobacco, Inc., Akira Hasegawa
    Inventors: Akira Hasegawa, Shinichi Uesato, Tomio Ishida, Tomio Ishida
  • Patent number: 5278302
    Abstract: The present invention relates to novel oligonucleotides having phosphorodithioate internucleotide linkages which may be used for the treatment of diseases caused by viruses.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: January 11, 1994
    Assignee: University Patents, Inc.
    Inventors: Marvin H. Caruthers, William S. Marshall
  • Patent number: 5273892
    Abstract: An acid heteropolysaccharide P-318 which comprises galactose, galacturonic acid, N-acetylfucosamine and pyruvic acid in a ratio of about 2:3:1:1, a sulfated heteropolysaccharide P-318 having a 10% or less sulfur content which is prepared by sulfating said acid heteropolysaccharide and a process for preparing an acid heteropolysaccharide P-318 which comprises culturing Pseudomonas sp. 318 to produce the acid heteropolysaccharide P-318 and collecting the thus produced acid heteropolysaccharide P-318. The sulfated polysaccharide P-318 of the invention shows a strong antiviral activity in spite of a lower content of sulfate.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: December 28, 1993
    Assignee: Teikoku Seiyaku Kabushiki Kaisha
    Inventor: Koichi Okutani
  • Patent number: 5274086
    Abstract: N-Acetyl-.beta.-D-glucosamine derivatives represented by the formula ##STR1## wherein R.sup.1 denotes a substituted alkyl group of 1 to 4 carbon atoms having a hydroxyl group, carboxyl group, sulfonic acid group or phosphoric acid group, or an alkali metal salt thereof, or a substituted phenyl group having a hydroxyl group, carboxyl group, sulfonic acid group, phosphoric acid group or said substituted alkyl group, or an alkali metal salt thereof, and R.sup.2, R.sup.3 and R.sup.4 each independently denote a hydrogen atom, halogen atom or nitro group, a process for producing the same, reagents for determining N-acetyl-.beta.-D-glucosaminidase activity containing said derivatives as effective ingredients, and a method for determining N-acetyl-.beta.-D-glucosaminidase activity using said derivatives.
    Type: Grant
    Filed: December 13, 1991
    Date of Patent: December 28, 1993
    Assignee: Kikkoman Corporation
    Inventors: Kouichi Kasai, Kiyoshi Okada, Nobuyuki Yamaji
  • Patent number: 5274085
    Abstract: A process for preparing erythromycin A oxime or a salt thereof which comprises reacting erythromycin A with hydroxylamine using an acid, is disclosed. Erythromycin A oxime and the salts thereof are useful as intermediates for the synthesis of macrolide antibiotics.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: December 28, 1993
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Takehiro Amano, Masami Goi, Kazuto Sekiuchi, Tomomichi Yoshida, Masahiro Hasegawa