Patents by Inventor Sumio Umezawa
Sumio Umezawa 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).
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Patent number: 6514946Abstract: 20,23-disubstituted mycaminosyltylonolide derivatives and use of the same in the field of the prophylaxis and treatment of pasteurellosis are disclosed. The di-substituents are peperidino optionally substituted with one or two methyl groups. The derivatives have selective antibacterial activity against Pasteurella.Type: GrantFiled: August 29, 2000Date of Patent: February 4, 2003Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Toshiaki Miyake, Tomohisa Takita, Masa Hamada, Tomio Takeuchi, Sumio Umezawa
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Patent number: 6184365Abstract: 7-O-(4-Amino-2,4,6-trideoxy-2-fluoro-&agr;-L-talopyranosyl)-daunomycinone or -adriamycinone is now synthesized as a novel daunomycinone or adriamycinone derivative having the general formula wherein R is a hydrogen atom or hydroxyl group. These novel compounds according to this invention exhibit excellent antitumor activities and have a high solubility in water, and hence they are useful as an antitumor agent.Type: GrantFiled: December 16, 1997Date of Patent: February 6, 2001Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi
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Patent number: 6075135Abstract: 7-O-(4-Amino-2,4,6-trideoxy-2-fluoro-.alpha.-L-mannopyranosyl)-daunomycinon e or -adriamycinone is now synthesized as a daunomycinone or adriamycinone derivative having the general formula ##STR1## wherein R is a hydrogen atom or hydroxyl group. These novel compounds according to this invention exhibit excellent antitumor activities and have a high solubility in water, and hence they are useful as an antitumor agent.Type: GrantFiled: March 31, 1999Date of Patent: June 13, 2000Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi
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Patent number: 5958889Abstract: 7-O-(4-Amino-2,4,6-trideoxy-2-fluoro-.alpha.-L-mannopyranosyl)daunomycinone or -adriamycinone is now synthesized as a daunomycinone or adriamycinone derivative having the general formula ##STR1## wherein R is a hydrogen atom or hydroxyl group. These novel compounds according to this invention exhibit excellent antitumor activities and have a high solubility in water, and hence they are useful as an antitumor agent.Type: GrantFiled: December 22, 1997Date of Patent: September 28, 1999Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi
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Patent number: 5886167Abstract: 2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin are synthesized in this invention through a multi-stage process via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.- and -.beta.-D-ribofuranosyl bromides. Further, according to this invention, 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin are synthesized by a multi-stage process starting from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.-D-arabinofuranosyl bromide. These four 2'-fluoro derivatives of coformycin are novel compounds and have high enzyme-inhibitory activities against adenosine deaminase. In particular, these novel compounds are useful substances which exhibit therapeutic effects on acute lymphocytic leukemias due to their high enzyme-inhibitory activities above-mentioned. In addition, a variety of intermediates are obtained as novel compounds which are useful for the synthesis of the aforesaid novel 2'-fluoro derivatives of coformycin.Type: GrantFiled: December 15, 1997Date of Patent: March 23, 1999Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yoshiaki Takahashi
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Patent number: 5831072Abstract: An object of this invention is to provide a novel process for the synthesis of a 2'-deoxy-2'-halocoformycin having an inhibitory activity against adenosine deaminase in a practically high yield. Thus, there is provided a process comprising multi-stage reactions with using as the starting intermediate a tert-butyl 1-(3,5-di-O-acyl-2-deoxy-2-halo-.beta.-D-ribofuranosyl or arabinofuranosyl)-5-aminoimidazole-4-carboxylate of formula (II) ##STR1## whereby there are produced a 2'-deoxy-2'-halocoformycin or a 2'-deoxy-2'-epi-2'-halocoformycin of formula (I-a) ##STR2## and also a 2'-deoxy-8-epi-2'-halocoformycin or a 2'-deoxy-8,2'-diepi-2'-halocoformycin of formula (I-b) ##STR3## It is expectable that a 2'-deoxy-2'-halocoformycin and epimers thereof are useful as a drug for lymphocytic leukemias and as drugs for various diseases attributable to the actions of adenosine deaminase.Type: GrantFiled: March 4, 1997Date of Patent: November 3, 1998Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yoshiaki Takahashi
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Patent number: 5801257Abstract: Novel anthracycline derivatives have now been produced, which exhibit higher antitumor activities and lower toxicities than those of daunomycin, adriamycin etc. that have been clinically used as anticancer agents. That is, a daunomycinone or adriamycinone derivative represented by the general formula (I): ##STR1## wherein R is a hydrogen atom or a hydroxyl group, and 7-O-(2,6-dideoxy-6,6,6-trifluoro-.alpha.-L-lyxo-hexopyranosyl)adriamycinon e derivative which is an adriamycinone derivative represented by formula (II): ##STR2## have now been newly synthesized. The novel anthracycline derivatives having the general formula (I) and formula (II), respectively, show excellent anticancer or antitumor activities and are of low toxicities. These novel compounds are very useful as anticancer or antitumor agents and are expected to be useful for the therapeutic treatments of a variety of cancers and tumors, similarly to daunomycin or adriamycin.Type: GrantFiled: October 20, 1997Date of Patent: September 1, 1998Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi
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Patent number: 5789386Abstract: To provide novel fluorine-containing anthracycline derivatives having high antitumor activities and a solubility in water, there have now been synthesized a 7-O-(2,6-dideoxy-2-fluoro-3-O- or -4-O- or -3,4-di-O-aminoalkanoyl-.alpha.-L-talopyranosyl)daunomycinone or -adriamycinone of general formula (I) shown below, as well as a 7-O-(3-O- or -4-O- or -3,4-di-O-aminoalkanoyl-2,6-dideoxy-2,6,6,6-tetrafluoro-.alpha.-L-talopyra nosyl- or -2,6-dideoxy-6,6,6-trifluoro-.alpha.-L-lyxo-hexopyranosyl)adriamycinone of general formula (II) shown below:General formula (I) ##STR1## General formula (II) ##STR2## wherein either one or both of A.sup.1 and A.sup.2 is or are an .alpha.-amino acid residue or an .omega.-amino acid residue and T denotes a fluorine or hydrogen atom. The novel fluorine-containing anthracycline derivatives of general formulae (I) and (II) are highly active against tumors and soluble in water, and they are useful as antitumor agents administrable in the form of injectable solution.Type: GrantFiled: September 9, 1996Date of Patent: August 4, 1998Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi, Hiromi Sohtome
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Patent number: 5773607Abstract: 2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin are synthesized in this invention through a multi-stage process via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.- and -.beta.-D-ribofuranosyl bromides. Further, according to this invention, 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin are synthesized by a multi-stage process starting from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.-D-arabinofuranosyl bromide. These four 2'-fluoro derivatives of coformycin are novel compounds and have high enzyme-inhibitory activities against adenosine deaminase. In particular, these novel compounds are useful substances which exhibit therapeutic effects on acute lymphocytic leukemias due to their high enzyme-inhibitory activities above-mentioned. In addition, a variety of intermediates are obtained as novel compounds which are useful for the synthesis of the aforesaid novel 2'-fluoro derivatives of coformycin.Type: GrantFiled: March 22, 1996Date of Patent: June 30, 1998Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yoshiaki Takahashi
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Patent number: 5719130Abstract: Novel anthracycline derivatives have now been produced, which exhibit higher antitumor activities and lower toxicities than those of daunomycin, adriamycin etc. that have been clinically used as anticancer agents. That is, a daunomycinone or adriamycinone derivative represented by the general formula (I): ##STR1## wherein R is a hydrogen atom or a hydroxyl group.Type: GrantFiled: September 9, 1996Date of Patent: February 17, 1998Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Yasushi Takagi
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Patent number: 5541303Abstract: A compound of the following formula is provided: ##STR1## wherein A represents a carbonyl group which may be protected; B represents an aldehyde group which may be protected; R.sup.1 represents a hydroxyl group which may be protected; R.sup.2 represents a hydrogen atom or acyl group; W represents a hydrogen atom, hydroxyl group, lower alkanoyloxy group or substituted sulfonyloxy group; Y represents a hydrogen atom, halogen atom, hydroxyl group or substituted sulfonyloxy group; and broken line "-------" represents a double bond or single bond. This compound is useful for producing 3,4'-dideoxymycaminosyltylonolide useful as an antimicrobial agent.Type: GrantFiled: July 13, 1994Date of Patent: July 30, 1996Assignee: Zaidan Hojin Biseibutsu Kagaku KenkyukaiInventors: Tomio Takeuchi, Sumio Umezawa, Osamu Tsuchiya, Shunji Kageyama, Toshiaki Miyake, Naoki Matsumoto, Kaichiro Kominato, Hiroshi Tanaka, Takeo Yoshioka
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Patent number: 5527781Abstract: As new compounds are now synthetized 5-deoxy-5,5-difluoro derivatives of aminoglycosidic antibiotics of neamine, kanamycin A-series, kanamycin B-series, gentamicin-series and seldomycin-series. Further, the 1-N-(.alpha.-hydroxy-.omega.-aminoalkanoyl) derivatives are synthetized from 5-deoxy-5,5-difluorokanamycins A and B, as well as their analogues now obtained. The 5-deoxy-5,5-difluoro derivatives of the aminoglycosidic antibiotics now provided according to this invention have such antibacterial activities enhanced much more than or equal to those of the respectively corresponding parent aminoglycosidic antibiotics, while these 5-deoxy-5,5-difluoro derivatives exhibit values of the 50% lethal dosage (LD.sub.50) which are improved remarkably better when they are intravenously administered to mice, so that they have remarkedly reduced toxicities to mammals.Type: GrantFiled: April 21, 1993Date of Patent: June 18, 1996Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Tomio Takeuchi, Sumio Umezawa, Tsutomu Tsuchiya, Tetsuo Shitara, Shunzo Fukatsu, Eijiro Umemura
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Patent number: 5101022Abstract: Mycaminosyl tylonolide derivatives represented by the following general formula ##STR1## (wherein R.sup.1 denotes hydroxyl group, a lower alkanoyloxy group, benzoyloxy group, azido group, or amino group which may optionally be substituted with a lower alkyl or a lower alkanoyl radical; R.sup.2 stands for hydrogen atom or hydroxyl group; R.sup.3 expresses hydrogen atom or formyl group; and means a double bond or a radical represented by ##STR2## and salts thereof.Type: GrantFiled: February 4, 1991Date of Patent: March 31, 1992Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Hamao Umezawa, Sumio Umezawa, Tsutomu Tsuchiya, Tomio Takeuchi, Akihiro Tanaka, Shuichi Sakamoto
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Patent number: 5096888Abstract: 3-Deoxy mycaminosyl tylonolide derivatives represented by the following general formula and salts thereof: ##STR1## wherein X represents an oxygen atom or .dbd.N--OR.sup.4 (wherein R.sup.4 represents hydrogen or lower alkyl); R.sup.1 represents a hydrogen atom, an acyl group or an alkylsilyl group; R.sup.2 represents a hydrogen atom or an acyl group; and R.sup.3 represents a hydrogen atom or a hydroxyl group. The compounds of this invention of the formula (I) are novel compounds and have excellent antibacterial activity.Type: GrantFiled: September 24, 1990Date of Patent: March 17, 1992Assignee: Zaidan Hojin Biseibutsu Kagaku KenkyikaiInventors: Sumio Umezawa, Tsutomu Tsuchiya, Tomio Takeuchi, Shunji Kageyama, Shuichi Sakamoto
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Patent number: 5034517Abstract: 2,6-Dideoxy-2-fluoro-L-talopyranose and 1-substituted derivatives thereof, including methyl 2,6-dideoxy-2-fluoro-L-talopyranoside and 3,4-di-O-protected-2,6-dideoxy-2-fluoro-L-talopyranosyl halides, are now provided and these new compounds are useful as intermediates for use in the synthesis of new compounds having antitumor activity, especially 7-O-(2,6-dideoxy-2-fluoro-.alpha.-L-talopyranosyl) daunomycinone or -adriamycinone. 2,6-Dideoxy-2-fluoro-L-talopyranose shows antibacterial activity. 2,6-Dideoxy-fluoro-L-talopyranose and the 1-substituted derivatives thereof may be produced by a multi-stage process starting from L-fucose.Type: GrantFiled: March 6, 1990Date of Patent: July 23, 1991Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Hamao Umezawa, Sumio Umezawa, Tsutomu Tsuchiya, Tomio Takeuchi, Yasushi Takagi
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Patent number: 4945081Abstract: Mycaminosyl tylonolide derivatives represented by the following general formula ##STR1## (wherein R.sup.1 denotes hydroxyl group, a lower alkanoyloxy group, benzyloxy group, azido group, or amino group which may optionally be substituted with a lower alkyl or a lower alkanoyl radical; R.sup.2 stands for hydrogen atom or hydroxyl group; R.sup.3 expresses hydrogen atom or formyl group; and means a double bond or a radical represented by ##STR2## and salts thereof.Type: GrantFiled: August 16, 1988Date of Patent: July 31, 1990Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Hamao Umezawa, Sumio Umezawa, Tsutomu Tsuchiya, Tomio Takeuchi, Akihiro Tanaka, Shuichi Sakamoto
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Patent number: 4914192Abstract: Mycaminosyl tylonolide derivatives represented by the following general formula ##STR1## (wherein R.sup.1 denoted hydroxyl group, a lower alkanoyloxy group, benzyloxy group, azido group, or amino group which may optionally be substituted with a lower alkyl or a lower alkanoyl radical; R.sup.2 stands for hydrogen atom or hydroxyl group; R.sup.3 expresses hydrogen atom or formyl group; and means a double bond or a radical represented by ##STR2## and salts thereof.Type: GrantFiled: September 14, 1988Date of Patent: April 3, 1990Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Hamao Umezawa, Sumio Umezawa, Tsutomu Tsuchiya, Tomio Takeuchi, Akihiro Tanaka, Shuichi Sakamoto
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Patent number: 4873225Abstract: As new compound are now provided ten compounds, namely 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}kanamycin A; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-2',3'-dideoxykanamycin A; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-2',3'-dideoxy-2'-fluorokan amycin A; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-5-deoxy-5-fluorokanamycin A; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-kanamycin B; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-3'-deoxykanamycin B; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-3',4'-dideoxykanamycin B; 1-N-{(2R,3R) -4-amino-3-fluoro-2-hydroxybutyryl}-5-deoxy-5-fluorokanamycin B; 1-N-{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-5,3'-dideoxy-5-fluorokanam ycin B; and 1-N{(2R,3R)-4-amino-3-fluoro-2-hydroxybutyryl}-5,3',4'-trideoxy-5-fluoroka namycin B, which are all useful as antibacterial agent in the therapeutic treatment of bacterial infections.Type: GrantFiled: February 22, 1988Date of Patent: October 10, 1989Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Sumio Umezawa, Tsutomu Tsuchiya, Tomio Takeuchi, Kazuo Umezawa, Yoshiaki Takahashi, Tetsuo Shitara, Yoshihiko Kobayashi, Yasushi Takagi
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Patent number: 4845082Abstract: New compound, 3',4'-dideoxy-3'-fluorokanamycin B is now provided, which is useful as antibacterial agent.3',4'-Dideoxy-3'-fluorokanamycin B is prepared by a process comprising halogenating an N,O-protected derivative of 3'-deoxy-3'-fluoro-4'-O-sulfonylkanamycin B with a metal halide, reducing the resulting 4'- halogenated 3'-deoxy-3'-fluorokanamycin B derivative to convert its 4'-halo group into a hydrogen atom, and thereby to produce an N,O-protected derivative of 3',4'-dideoxy-3'-fluorokanamycin B, and removing the remaining amino-protecting groups and the remaining hydroxyl-protecting groups from the reduction product by conventional deprotecting methods.Type: GrantFiled: August 22, 1986Date of Patent: July 4, 1989Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Hamao Umezawa, Sumio Umezawa, Tsutomu Tsuchiya, Yoshihiko Kobayashi
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Patent number: 4794173Abstract: Mycaminosyl tylonolide derivatives represented by the following general formula ##STR1## (wherein R.sup.1 denotes hydroxyl group, a lower alkanoyloxy group, benzoyloxy group, azido group, or amino group which mat optionally be substituted with a lower alkyl or a lower alkanoyl radical; R.sup.2 stands for hydrogen atom or hydroxyl group; R.sup.3 expresses hydrogen atom or formyl group; and means a double bond or a radical represented by ), and salts thereof.Type: GrantFiled: May 9, 1986Date of Patent: December 27, 1988Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Hamao Umezawa, Sumio Umezawa, Tsutomu Tsuchiya, Tomio Takeuchi, Akihiro Tanaka, Shuichi Sakamoto