Patents Assigned to Yamasa Shoyu Kabushiki Kaisha
  • Patent number: 5939543
    Abstract: The present invention provides two kinds of solid 2-octynyl adenosine products with novel properties which are stabilized with respect to temperature or temperature and humidity, one being solid 2-octynyl adenosine having a moisture content of not more than 3%, and the other being solid 2-octynyl adenosine deposited from an anhydrous alcoholic solution or hydrous alcoholic solution of 2-octynyl adenosine, said hydrous alcoholic solution having a water content of less than 1%.
    Type: Grant
    Filed: February 11, 1992
    Date of Patent: August 17, 1999
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Manami Morozumi, Masao Kumagai, Toyofumi Yamaguchi
  • Patent number: 5747652
    Abstract: Using as an immunogen an oligopeptide containing a different portion of the amino acid sequence of isoform SM-1, SM-2 or SM-3 in smooth muscle myosin heavy chains, for example, the C-terminus amino acid sequence, antibodies capable of distinctly recognizing each isoform from other isoforms of the smooth muscle myosin heavy chains can be obtained. The antibodies are useful as reagents for tissue staining and also useful as diagnostic reagents of vascular disturbance or arteriosclerosis.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: May 5, 1998
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Ryozo Nagai, Makoto Kuroo, Hirohisa Kato
  • Patent number: 5506110
    Abstract: As a carrier for binding of the antiphospholipid antibodies used for immunological diagnosis of antiphospholipid syndrome, a phospholipid-bound carrier treated with purified serum albumin and a surfactant is used. Thus, immunological diagnosis of antiphospholipid syndrome can be made with high accuracy. By using the fraction or protein obtained from animal serum or plasma, having the activity of enhancing the binding ability of the antibodies specifically present in the antiphospholipid syndrome to the phospholipid, immunological diagnosis of antiphospholipid syndrome can also be made more accurately, as compared to known diagnosis.
    Type: Grant
    Filed: June 14, 1993
    Date of Patent: April 9, 1996
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Eiji Matsuura, Yoshiko Igarashi, Hisato Nagae
  • Patent number: 5506122
    Abstract: The present invention concerns a process for producing nucleosides by carrying out the reaction of a base donor, a saccharide residue donor and a phosphoric acid donor by the use of an enzyme preparation containing nucleoside phosphorylase, thereby forming an N-glycosidic bond between the base moiety of the base donor and the saccharide moiety of the saccharide residue donor, which comprises using, as the enzyme preparation containing nucleoside phosphorylase, a preparation derived from the cells of one or more kinds of microorganisms belonging to thermophiles of the genus Bacillus and having high nucleoside phosphorylase activity per unit cell weight.
    Type: Grant
    Filed: October 7, 1994
    Date of Patent: April 9, 1996
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Hiroshi Yamauchi, Hideki Utsugi, Yuichiro Midorikawa
  • Patent number: 5459254
    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## [I] A=a leaving group, [II] A=NH.sub.2,[V] A=NHR.sup.4,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: November 10, 1993
    Date of Patent: October 17, 1995
    Assignees: Yamasa Shoyu Kabushiki Kaisha, Toa Eiyo Ltd.
    Inventors: Toyofumi Yamaguchi, Takanori Miyashita, Shinji Sakata, Toichi Abiru, Akira Matsuda, Tohru Ueda, Kentaro Kogi
  • Patent number: 5430139
    Abstract: Disclosed are novel 2'-alkylidenepyrimidine nucleoside derivatives represented by formula [I]: ##STR1## R.sup.1 is an amino group or a hydroxy group, R.sup.2 is a hydrogen atom, a halogen atom or a lower alkyl group, R.sup.3 is a hydrogen atom or a lower alkyl group, and R.sup.4 is a hydrogen atom or a phosphate residue, or salts thereof. These novel compounds can be produced from uridine or cytidine derivatives by alkylidenating the 2'-position in the sugar moiety thereof with Wittig's reagent. Furthermore, the compounds have remarkable antiviral activities and therefore can provide novel antiviral agents.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: July 4, 1995
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Akira Matsuda, Tohru Ueda, Kenji Takenuki, Haruhiko Machida
  • Patent number: 5384251
    Abstract: The present invention concerns a process for producing nucleosides by carrying out the reaction of a base donor, a saccharide residue donor and a phosphoric acid donor by the use of an enzyme preparation containing nucleoside phosphorylase, thereby forming an N-glycosidic bond between the base moiety of the base donor and the saccharide moiety of the saccharide residue donor, which comprises using, as the enzyme preparation containing nucleoside phosphorylase, a preparation derived from the cells of one or more kinds of microorganisms belonging to thermophiles of the genus Bacillus and having high nucleoside phosphorylase activity per unit cell weight.
    Type: Grant
    Filed: May 4, 1993
    Date of Patent: January 24, 1995
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Hiroshi Yamauchi, Hideki Utsugi, Yuichiro Midorikawa
  • Patent number: 5344758
    Abstract: A method for determining whether antiphospholipid antibodies are present in a sample is disclosed. The method comprises contacting the sample with a negatively charged phospholipid and with .beta.-2-glycoprotein-I or a homolog or analog thereof and determining whether any antiphospholipid antibodies have bound to the contacted phospholipid and .beta.-2-glycoprotein-I, wherein detection of binding of antiphospholipid antibodies to the phospholipid and .beta.-2-glycoprotein-I, is indicative that antiphospholipid antibodies are present in the sample.
    Type: Grant
    Filed: December 6, 1991
    Date of Patent: September 6, 1994
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Steven A. Krilis, Hugh P. McNeill, Colin N. Chesterman
  • Patent number: 5334593
    Abstract: The present invention relates to an anxiolytic drug comprising as an active ingredient a 1-amino-5-halogenouracil represented by formula [I]: ##STR1## wherein X represents a halogen atom, or pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: July 9, 1992
    Date of Patent: August 2, 1994
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Masahiro Imaizumi, Shinji Sakata
  • Patent number: 5304471
    Abstract: A process of producing a foreign protein is provided which comprises transforming E. coli with a plasmid carrying a fused DNA having a DNA fragment encoding a foreign protein located downstream of a transcription initiation signal and translation initiation signal both derived from an appropriate T4 phage gene, infecting the transformant with a T4 phase denB and/or alc mutant at a low multiplicity of infection, and then culturing the infected transformant. The desired foreign protein can be produced in an extremely high yield, as compared to the prior art technique.
    Type: Grant
    Filed: February 8, 1991
    Date of Patent: April 19, 1994
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Toshitada Noguchi, Hideo Takahashi
  • Patent number: 5300636
    Abstract: Disclosed are novel 2'-alkylidenepyrimidine nucleoside derivatives represented by formula [I]: ##STR1## wherein R.sup.1 is an amino group or a hydroxy group, R.sup.2 is a hydrogen atom, a halogen atom or a lower alkyl group, R.sup.3 is a hydrogen atom or a lower alkyl group, and R.sup.4 is a hydrogen atom or a phosphate residue, or salts thereof.These novel compounds can be produced from uridine or cytidine derivatives by alkylidenating the 2'-position in the sugar moiety thereof with Wittig's reagent.Furthermore, the compounds have remarkable antiviral activities and therefore can provide novel antiviral agents.
    Type: Grant
    Filed: June 26, 1991
    Date of Patent: April 5, 1994
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Akira Matsuda, Tohru Ueda, Kenji Takenuki, Haruhiko Machida
  • Patent number: 5298397
    Abstract: The present invention is concerned with a method of assaying D-vanillylmandelic acid (D-VMA) contained in a specimen of a living organism through the following steps (A) to (D), and a reagent and a kit used for the assay, wherein a racemic mixture of VMA is used as the standard substance for preparing a calibration curve and a labeled anti-D-VMA antibody is used as the labeled anti-VMA antibody to specifically assay only D-VMA in the specimen:(A) the step of conducting a competitive reaction of VMA in the specimen and VMA in solid phase against the labeled anti-VMA antibody;(B) the step of separating the liquid phase from the solid phase;(C) the step of determining the quantity of labeling of the labeled anti-VMA antibody combined with the solid-phase VMA and that of other substances; and(D) the step of preparing a calibration curve or obtaining an equation by using a standard substance of a known concentration, calculating the concentration of VMA corresponding to the quantity of labeling determined in the s
    Type: Grant
    Filed: June 19, 1991
    Date of Patent: March 29, 1994
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Manami Kuroda, Masahito Sugi
  • 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: 5270304
    Abstract: The present invention concerns a therapeutic-prophylactic agent for ischemic diseases of the heart or brain, comprising as an active ingredient a 2-alkynyladenosine represented by the following formula: ##STR1## wherein n represents an integer of from 2 to 15.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: December 14, 1993
    Assignees: Yamasa Shoyu Kabushiki Kaisha, Toa Eiyo Ltd.
    Inventors: Kentaro Kogi, Toichi Abiru, Toyofumi Yamaguchi
  • Patent number: 5258301
    Abstract: The present invention concerns a process for producing nucleosides by carrying out the reaction of a base donor, a saccharide residue donor and a phosphoric acid donor by the use of an enzyme preparation containing nucleoside phosphorylase, thereby forming an N-glycosidic bond between the base moiety of the base donor and the saccharide moiety of the saccharide residue donor, which comprises using, as the enzyme preparation containing nucleoside phosphorylase, a preparation derived from the cells of one or more kinds of microorganisms belonging to thermophiles of the genus Bacillus and having high nucleoside phosphorylase activity per unit cell weight.
    Type: Grant
    Filed: October 26, 1990
    Date of Patent: November 2, 1993
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Hiroshi Yamauchi, Hideki Utsugi, Yuichiro Midorikawa
  • Patent number: 5252576
    Abstract: Disclosed are a central nervous system depressant which comprises a 1-amino-5-halogenouracil represented by the formula ##STR1## wherein X represents a halogen atom, or a pharmaceutically acceptable salt thereof as an active ingredient;a 1-amino-5-halogenouracil represented by the formula ##STR2## wherein X' represents chlorine, bromine or iodine, or a salt thereof; and a process for preparing a 1-amino-5-halogenouracil represented by the above shown formula [I] from a pyrimidine derivative represented by the formula ##STR3## wherein X represents a halogen atom and R represents a protective group.
    Type: Grant
    Filed: January 17, 1991
    Date of Patent: October 12, 1993
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Shinji Sakata, Masahiro Imaizumi
  • Patent number: 5189027
    Abstract: Disclosed herein are a novel 2-substituted adenosine derivative having the following formula [I] ##STR1## wherein R represents a hydrogen atom or a hydroxyl group, m is an integer of 2 to 7, n is 0 or an integer of 1 to 3, and R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each independently represent a hydrogen atom, a hydroxy protective group or a phosphoric acid residue, and salts thereof.The above compounds are excellent in a circulation ameliorating effect such as a vasodepressor activity, and have high selectivity for A.sub.2 receptors, but cause less undesirable side effects such as a suppresssive effect on the heart. They are therefore effective when used in pharmaceutical compositions for circulatory diseases.
    Type: Grant
    Filed: November 27, 1991
    Date of Patent: February 23, 1993
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Takanori Miyashita, Toichi Abiru, Yohko Watanabe, Toyofumi Yamaguchi, Akira Matsuda
  • Patent number: 5126361
    Abstract: Disclosed are imidazole derivatives represented by formula [I]: ##STR1## wherein R is a hydrogen atom or ##STR2## wherein R.sup.2 is a hydrogen atom or a hydroxy protecting group, R.sup.2 protecting either a single hydroxy or two hydroxies together when R.sup.2 is a hydroxy protecting group, and R.sup.3 is a hydrogen atom or OR.sup.2 ; A is CONH.sub.2 or CN; and R.sup.1 is a hydrogen atom, lower alkyl, hydroxy lower alkyl, or phenyl.Also disclosed are six processes for producing these novel compounds among which a typical process comprises reacting a starting imidazole compound having a halogen at the 5-position thereof with an acetylene derivative to alkynylate the 5-position.Furthermore, the compounds have remarkable antitumor activities and therefore can provide novel antitumor agents.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: June 30, 1992
    Assignee: Yamasa Shoyu Kabushiki Kaisha
    Inventors: Tohru Ueda, Akira Matsuda, Noriaki Minakawa, Takuma Sasaki, Yoshikazu Yanagi
  • Patent number: 5059590
    Abstract: Disclosed are imidazole derivatives represented by formula [I]: ##STR1## wherein R is a hydrogen atom or ##STR2## wherein R.sup.2 is a hydrogen atom or a hydroxy protecting group, R.sup.2 protecting either a single hydroxy or two hydroxies together when R.sup.2 is a hydroxy protecting group, and R.sup.3 is a hydrogen atom or OR.sup.2 ; A is CONH.sub.2 or CN; and R.sup.1 is a hydrogen atom, lower alkyl, hydroxy lower alkyl, or phenyl.Also disclosed are six processes for producing these novel compounds among which a typical process comprises reacting a starting imidazole compound having a halogen at the 5-position thereof with an acetylene derivative to alkynylate the 5-position.Furthermore, the compounds having remarkable antitumor activities and therefore can provide novel antitumor agents.
    Type: Grant
    Filed: February 28, 1989
    Date of Patent: October 22, 1991
    Assignees: Yamasa Shoyu Kabushiki Kaisha, Sumitomo Pharmaceuticals Company Limited
    Inventors: Tohru Ueda, Akira Matsuda, Noriaki Minakawa, Takuma Sasaki, Yoshikazu Yanagi
  • Patent number: 5049663
    Abstract: Disclosed herein are a novel process for producing 1-.beta.-D-arabinofuranosylcytosine-5'-stearylphosphate monosodium salt, which has been expected as an oral antitumor agent, and 1-.beta.-D-arabinofranosylcytosine-5'-stearylphosphate monosodium salt monohydrate obtained from the above-mentioned monosodium salt.
    Type: Grant
    Filed: August 25, 1989
    Date of Patent: September 17, 1991
    Assignees: Nippon Kayaku Kabushiki Kaisha, Yamasa Shoyu Kabushiki Kaisha
    Inventors: Takashi Terada, Minoru Aoki, Hiroshi Ohtaki, Manami Morozumi