Patents by Inventor Tadashi Shirai

Tadashi Shirai has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5240944
    Abstract: Derivatives of cyclic guanidine are disclosed, which are represented by the following formula:A--S--Rwherein A is ##STR1## R.sub.1 represent a lower alkyl or substituted phenyl or unsubstituted phenyl group; R.sub.2 is a lower alkyl; R.sub.3 is H or a lower alkyl; R is lower alkyl, alkenyl, alkynyl, alkanoyl, alkenoyl, dialkylaminoalkyl, cyanoalkyl, alkoxycarbonylalkyl, carboxylalkenyl, alkoxycarbonyl, alkoxyalkylcarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, phenoxyalkylcarbonyl, piperidinoalkyl, pyridine carbonyl, substituted or unsubstituted benzoyl, or substituted or unsubstituted benzyl group. The compounds of the present invention are useful as anti-ulcerative agents.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: August 31, 1993
    Assignee: Kotobuki Seiyaku Co. Ltd.
    Inventors: Tsuyoshi Tomiyama, Akira Tomiyama, Tadashi Shirai, Shuuichi Wakabayashi, Tomoyuki Kawai, Naoto Ueyama, Motoharu Sonegawa
  • Patent number: 5008282
    Abstract: Derivatives of cyclic guanidine are disclosed, which are represented by the following formula:A--S--Rwherein A is ##STR1## R.sub.1 represent a lower alkyl or substituted phenyl or unsubstituted phenyl group; R.sub.2 is a lower alkyl; R.sub.3 is H or a lower alkyl; R is lower alkyl, alkenyl, alkynyl, alkanoyl, alkenoyl, dialkylaminoalkyl, cyanoalkyl, alkoxycarbonylalkyl, carboxylalkenyl, alkoxycarbonyl, alkoxyalkylcarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, phenoxyalkylcarbonyl, piperidinoalkyl, pyridine carbonyl, substituted or unsubstituted benzoyl, or substituted or unsubstituted benzyl group.The compounds of the present invention are useful as anti-ulcerative agents.
    Type: Grant
    Filed: December 13, 1989
    Date of Patent: April 16, 1991
    Assignee: Kotobuki Seiyaku Co. Ltd.
    Inventors: Tsuyoshi Tomiyama, Akira Tomiyama, Tadashi Shirai, Shuuichi Wakabayashi, Tomoyuki Kawai, Naoto Ueyama, Motoharu Sonegawa
  • Patent number: 4453003
    Abstract: A process for producing threo-3-amino-2-hydroxybutanoylaminoacetic acids comprises the steps of allowing to react a starting compound represented by the general formula: ##STR1## wherein R.sub.1 represents a naphthyl or a group of the formula: ##STR2## in which R.sub.6 and R.sub.7 represent individually hydrogen, halogen, amino or a protected amino, hydroxy or a protected hydroxy, a lower alkoxy or a lower alkyl and R.sub.2 represents a protected amino, with a starting compound represented by the general formula: ##STR3## wherein R.sub.3 represents hydrogen or an ester residue, to obtain threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its ester represented by the general formula: ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 have the same meanings as above, and then reducing the same into threo-3-protected amino-2-hydroxybutanoic acid or its ester represented by the general formula: ##STR5## wherein R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: December 31, 1981
    Date of Patent: June 5, 1984
    Inventors: Hamao Umezawa, Takaaki Aoyagi, Tadashi Shirai, Rinzo Nishizawa, Masao Suzuki, Tetsushi Saino
  • Patent number: 4391986
    Abstract: Threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its esters represented by the formula: ##STR1## wherein R.sub.1 represents naphthyl or a group of the formula ##STR2## in which R.sub.6 and R.sub.7 represent individually hydrogen, halogen, amino, an amino protected with acyl, lower alkyloxycarbonyl or carbamoyl, hydroxy or protected with acyl, lower alkyloxycarbonyl or carbamoyl, lower alkoxy, lower alkyl or phenyl group; R.sub.2 represents an amine protected with acyl, lower alkyloxycarbonyl or carbamoyl; and R.sub.3 represents hydrogen, lower alkyl having 1 to 6 carbon atoms or benzyl.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: July 5, 1983
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hamao Umezawa, Takaaki Aoyagi, Tadashi Shirai, Rinzo Nishizawa, Masao Suzuki, Tetsushi Saino
  • Patent number: 4281180
    Abstract: A process for producing threo-3-amino-2-hydroxybutanoylaminoacetic acids comprises the steps of allowing to react a starting compound represented by the general formula: ##STR1## wherein R.sub.1 represents a naphthyl or a group of the formula: ##STR2## in which R.sub.6 and R.sub.7 represent individually hydrogen, halogen, amino or a protected amino, hydroxy or a protected hydroxy, a lower alkoxy or a lower alkyl and R.sub.2 represents a protected amino, with a starting compound represented by the general formula: ##STR3## wherein R.sub.3 represents hydrogen or an ester residue, to obtain threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its ester represented by the general formula: ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 have the same meanings as above, and then reducing the same into threo-3-protected amino-2-hydroxybutanoic acid or its ester represented by the general formula: ##STR5## wherein R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: November 23, 1979
    Date of Patent: July 28, 1981
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hamao Umezawa, Takaaki Aoyagi, Tadashi Shirai, Rinzo Nishizawa, Masao Suzuki, Tetsushi Saino
  • Patent number: 4115439
    Abstract: DL- .alpha.-phenylglycine can be combined with benzene-sulfonic acid, p-ethylbenzenesulfonic acid or m-xylenesulfonic acid to give the salt. The salt of the racemate may be more soluble in a sulfuric acid solution than the salt of the optically active isomer by suitably choosing the concentration of the sulfuric acid solution, and then the optical resolution by fractional crystallization is carried out. The D- or L- .alpha.-phenylglycine sulfonate is easily liberated of the sulfonic acid portion to give optically active D- or L- .alpha.-phenylglycine.
    Type: Grant
    Filed: March 25, 1976
    Date of Patent: September 19, 1978
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Shigeru Aoki, Yasuhisa Tashiro, Yuzo Aboshi, Toshiro Narita, Tadashi Shirai
  • Patent number: 4107203
    Abstract: In order to separate optically active D- or L-.alpha.-phenylglycine hydrochloride from a supersaturated solution of DL-.alpha.-phenylglycine hydrochloride seed crystals of the desired D- or L-isomer are added to the solution in the presence of a metal chloride.
    Type: Grant
    Filed: August 8, 1977
    Date of Patent: August 15, 1978
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Yasuhisa Tashiro, Hideo Sugimura, Toshiaki Arai, Masao Suzuki, Tadashi Shirai
  • Patent number: 4002666
    Abstract: Optically active p-hydroxyphenylglycine is prepared by reacting a racemic compound of a specified p-hydroxyphenylglycine derivative with optically active .alpha.-phenylethylamine to form a corresponding salt, obtaining two types of optically active salts therefrom by fractional crystallization, and obtaining optically active p-hydroxyphenylglycine by decomposition and hydrolysis of at least one of the optically active salts.
    Type: Grant
    Filed: October 22, 1974
    Date of Patent: January 11, 1977
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tadashi Shirai, Yasuhisa Tashiro, Shigeru Aoki
  • Patent number: 3994962
    Abstract: Optically active p-hydroxyphenylglycine is manufactured by inoculating a supersaturated solution of a p-hydroxyphenylglycine sulfonic acid derivative salt comprising a mixture of the two optically active enantiomers of said salt with an optically active enantiomer of the same salt, said mixture being either racemic or else one in which the predominant enantiomer is that of the inoculant. In this manner the enantiomer having the form of the inoculant is selectively crystallized. The selectively crystallized salt is thereafter treated for removal of the sulfonic acid derivative.
    Type: Grant
    Filed: January 28, 1975
    Date of Patent: November 30, 1976
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tadashi Shirai, Yasuhisa Tashiro, Shigeru Aoki
  • Patent number: 3932374
    Abstract: A process for preparing bleomycinic acid having a melting point of 228.degree.-230.degree.C. (decomposition) and an analysis of C : 40.80%, H : 5.29%, N : 16.45%, O : 24.78%, S : 4.53%, Cl : 3.37%, and Cu : 4.78% which is characterized by being soluble in water, difficultly soluble in methanol, acetic acid and dimethylsulfoxide, and insoluble in ethanol, ethyl acetate, acetone and ether, and which tests positive to Pauly and Ehrlich reactions but tests negative to ninhydrin, Sakaguchi, Dragendorf, Tollens, ferric chloride, Fehling and Molish reactions, and which has a maximum ultraviolet absorption spectrum at 246 m.mu. and 292 m.mu. and which has an infrared absorption spectrum bands at 3350, 1720, 1670, 1640, 1580, 1460, 1365, 1050, 770 (cm.sup.-.sup.1), and which can be hydrolyzed to yield 2'-(2-aminoethyl)-2,4'-bithiazole-4-carboxylic acid, L-threonine, 4-amino-3-hydroxy-2-methyl-.eta.-valeric acid, .beta.-hydroxy-histidine, .beta.-amino-.beta.
    Type: Grant
    Filed: June 13, 1974
    Date of Patent: January 13, 1976
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Hamao Umezawa, Yasushi Takahashi, Tadashi Shirai, Akio Fujii
  • Patent number: RE30413
    Abstract: A process for preparing bleomycinic acid having a melting point of 228.degree.-230.degree. C. (decomposition) and an analysis of C: 40.80%, H: 5.29%, N: 16.45%, O: 24.78%, S: 4.53%, Cl: 3.37%, and Cu: 4.78% which is characterized by being soluble in water, difficultly soluble in methanol, acetic acid and dimethylsulfoxide, and insoluble in ethanol, ethyl acetate, acetone and ether, and which tests positive to Pauly and Ehrlich reactions but tests negative to ninhydrin, Sakaguchi, Dragendorf, Tollens, ferric chloride, Fehling and Molish reactions, and which has a maximum ultraviolet absorption spectrum at 246 m.mu. and 292 m.mu. and which has an infrared absorption spectrum bands at 3350, 1720, 1670, 1640, 1580, 1460, 1365, 1050, 770 (cm.sup.-1), and which can be hydrolyzed to yield 2'-(2-aminoethyl)-2,4'-bithiazole-4-carboxylic acid, L-threonine, 4-amino-3-hydroxy-2-methyl-.eta.-valeric acid, .beta.-hydroxy-histidine, .beta.-amino-.beta.-(4-amino-6-carboxy-5-methylpyrimidine-2-yl)-propionic acid, L-.beta.
    Type: Grant
    Filed: May 24, 1979
    Date of Patent: October 7, 1980
    Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
    Inventors: Hamao Umezawa, Yasushi Takahashi, Tadashi Shirai, Akio Fujii