Patents Assigned to Yamasa Shoyu Kabushiki Kaisha
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Patent number: 5939543Abstract: 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: GrantFiled: February 11, 1992Date of Patent: August 17, 1999Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Manami Morozumi, Masao Kumagai, Toyofumi Yamaguchi
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Patent number: 5747652Abstract: 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: GrantFiled: December 20, 1994Date of Patent: May 5, 1998Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Ryozo Nagai, Makoto Kuroo, Hirohisa Kato
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Patent number: 5506110Abstract: 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: GrantFiled: June 14, 1993Date of Patent: April 9, 1996Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Eiji Matsuura, Yoshiko Igarashi, Hisato Nagae
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Patent number: 5506122Abstract: 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: GrantFiled: October 7, 1994Date of Patent: April 9, 1996Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Hiroshi Yamauchi, Hideki Utsugi, Yuichiro Midorikawa
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Patent number: 5459254Abstract: 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: GrantFiled: November 10, 1993Date of Patent: October 17, 1995Assignees: Yamasa Shoyu Kabushiki Kaisha, Toa Eiyo Ltd.Inventors: Toyofumi Yamaguchi, Takanori Miyashita, Shinji Sakata, Toichi Abiru, Akira Matsuda, Tohru Ueda, Kentaro Kogi
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Patent number: 5430139Abstract: 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: GrantFiled: September 24, 1993Date of Patent: July 4, 1995Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Akira Matsuda, Tohru Ueda, Kenji Takenuki, Haruhiko Machida
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Patent number: 5384251Abstract: 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: GrantFiled: May 4, 1993Date of Patent: January 24, 1995Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Hiroshi Yamauchi, Hideki Utsugi, Yuichiro Midorikawa
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Patent number: 5344758Abstract: 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: GrantFiled: December 6, 1991Date of Patent: September 6, 1994Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Steven A. Krilis, Hugh P. McNeill, Colin N. Chesterman
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Patent number: 5334593Abstract: 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: GrantFiled: July 9, 1992Date of Patent: August 2, 1994Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Masahiro Imaizumi, Shinji Sakata
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Patent number: 5304471Abstract: 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: GrantFiled: February 8, 1991Date of Patent: April 19, 1994Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Toshitada Noguchi, Hideo Takahashi
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Patent number: 5300636Abstract: 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: GrantFiled: June 26, 1991Date of Patent: April 5, 1994Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Akira Matsuda, Tohru Ueda, Kenji Takenuki, Haruhiko Machida
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Patent number: 5298397Abstract: 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 sType: GrantFiled: June 19, 1991Date of Patent: March 29, 1994Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Manami Kuroda, Masahito Sugi
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Patent number: 5283327Abstract: 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: GrantFiled: April 17, 1991Date of Patent: February 1, 1994Assignees: Yamasa Shoyu Kabushiki Kaisha, Toa Eiyo Ltd.Inventors: Toyofumi Yamaguchi, Toichi Abiru, Akira Matsuda, Tohru Ueda, Kentaro Kogi
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Patent number: 5270304Abstract: 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: GrantFiled: May 15, 1991Date of Patent: December 14, 1993Assignees: Yamasa Shoyu Kabushiki Kaisha, Toa Eiyo Ltd.Inventors: Kentaro Kogi, Toichi Abiru, Toyofumi Yamaguchi
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Patent number: 5258301Abstract: 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: GrantFiled: October 26, 1990Date of Patent: November 2, 1993Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Hiroshi Yamauchi, Hideki Utsugi, Yuichiro Midorikawa
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Patent number: 5252576Abstract: 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: GrantFiled: January 17, 1991Date of Patent: October 12, 1993Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Shinji Sakata, Masahiro Imaizumi
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Patent number: 5189027Abstract: 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: GrantFiled: November 27, 1991Date of Patent: February 23, 1993Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Takanori Miyashita, Toichi Abiru, Yohko Watanabe, Toyofumi Yamaguchi, Akira Matsuda
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Patent number: 5126361Abstract: 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: GrantFiled: May 15, 1991Date of Patent: June 30, 1992Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Tohru Ueda, Akira Matsuda, Noriaki Minakawa, Takuma Sasaki, Yoshikazu Yanagi
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Patent number: 5059590Abstract: 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: GrantFiled: February 28, 1989Date of Patent: October 22, 1991Assignees: Yamasa Shoyu Kabushiki Kaisha, Sumitomo Pharmaceuticals Company LimitedInventors: Tohru Ueda, Akira Matsuda, Noriaki Minakawa, Takuma Sasaki, Yoshikazu Yanagi
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Patent number: 5049663Abstract: 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: GrantFiled: August 25, 1989Date of Patent: September 17, 1991Assignees: Nippon Kayaku Kabushiki Kaisha, Yamasa Shoyu Kabushiki KaishaInventors: Takashi Terada, Minoru Aoki, Hiroshi Ohtaki, Manami Morozumi