7,7-disubstituted Patents (Class 540/221)
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Patent number: 4992541Abstract: The present invention relates to an improved process for the preparation of the compounds of formula (I) ##STR1## which involve the direct oxidation without N-protection of the compound of the formula (II) ##STR2##Type: GrantFiled: August 1, 1989Date of Patent: February 12, 1991Assignee: Merck & Co., Inc.Inventors: Thomas J. Blacklock, John W. Butcher, Paul Sohar, Theresa Lamanec
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Patent number: 4980464Abstract: A method for producing a compound of the formula; ##STR1## wherein R stands for a hydrogen atom, an acyl group or a protective group other than acyl groups, Q stands for a hydrogen atom or an ester residue, Y stands for the residue of a nucleophilic compound and the dotted line shows the double bond at 2- or 3- position of the cephem ring or a salt thereof, characterized by allowing a compound of the formula; ##STR2## [R, Q and the dotted line are of the same meaning as above] or a salt thereof to react with a nucleophilic compound or a salt thereof and a compound of the formula; ##STR3## wherein R.sup.1, R.sup.2, R.sup.3 independently stand for a hydrocarbon group having not more than 8 carbon atoms, or R.sup.1 and R.sup.2, R.sup.1 and R.sup.3 or R.sup.2 and R.sup.Type: GrantFiled: June 30, 1989Date of Patent: December 25, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Kenzo Naito, Yukio Ishibashi
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Patent number: 4973684Abstract: Broad spectrum antibiotics are provided which are compounds of the formula: ##STR1## wherein R.sup.4 is a residue of a nucleophilic compound and R.sup.5 is hydroxyl or protected hydroxyl; or a pharmaceutically acceptable salt or ester thereof.Type: GrantFiled: June 7, 1988Date of Patent: November 27, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Michihiko Ochiai, Taiiti Okada, Osamu Aki, Akira Morimoto, Kenji Kawakita, Yoshihiro Matsushita
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Patent number: 4971964Abstract: A pyridine derivative represented by formula (I): ##STR1## wherein the symbols are as defined in the specification, which exhibits selective, potential, and long-lasting inhibitory activity on biosynthesis of thromboxane A.sub.2 and is useful in the treatment and prevention of a broad range of diseases.Type: GrantFiled: June 15, 1989Date of Patent: November 20, 1990Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Koji Suzuki, Obase Hiroyuki, Akira Karasawa, Shiro Shirakura, Kubo Shizuoka, Ichiro Miki, Akio Ishii
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Patent number: 4958018Abstract: Disclosed is a method of producing a 3-exomethylenecepham of the formula ##STR1## wherein R.sup.1 is amino or substituted amino and R.sup.2 is a carboxy-protecting group comprising reacting a cephem of the formula ##STR2## wherein R.sup.1 and R.sup.2 are as defined above and X is halogen with lead metal while maintaining the pH of the reaction system at about 0.1 to 8. The cephem (I) may be reacted with a catalytic amount of lead metal or a lead compound in the presence of a metal having a greater ionization tendency than lead.Type: GrantFiled: May 4, 1989Date of Patent: September 18, 1990Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Sigeru Torii, Hideo Tanaka, Masatoshi Taniguchi, Michio Sasaoka, Norio Saito, Takashi Shiroi, Shigemitsu Nagao, Ryo Kikuchi, Yutaka Kameyama
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Patent number: 4956358Abstract: The compounds having a 4,11-dioxo-3-oxa-8(or 7)-thia-1-azatricyclo[7,2,0,0.sup.2,6 ]undecane-2-carboxylic acid skeleton as the base structures, their esters and their salts are useful antibacterial agents.Type: GrantFiled: July 10, 1987Date of Patent: September 11, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Akira Morimoto, Noriyoshi Noguchi, Nobuo Choh
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Patent number: 4950660Abstract: The present invention relates to a cephem compound of formula (III) shown in the description. The compound is useful as an intermediate for the synthesis of .beta.-lactam antibiotics of new class and also to a process for producing the same. The cephem compound (III) is produced by reacting a cephem compound of formula (I) with a nitrogen-containing compound of formula (II) under acid-capturing conditions. The process can be performed easily under mild conditions.Type: GrantFiled: September 6, 1988Date of Patent: August 21, 1990Assignee: Meiji Seika Kabushiki KaishaInventors: Kunio Atsumi, Yuichi Yamamoto, Kenji Sakagami, Ken Nishihata, Shinichi Kondo
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Patent number: 4940702Abstract: .beta.-Lactam antibiotics are disclosed which have the formulae (Ia) or pharmaceutically acceptable salts or pharmaceutically acceptable in vivo hydrolysable esters thereof: ##STR1## wherein R.sup.1 is phenyl, substituted phenyl, cyclohexenyl, cyclohexadienyl, or an optionally substituted 5- or 6-membered heterocyclic ring containing up to three hetero-atoms selected from oxygen, sulphur or nitrogen; R.sup.2 is hydrogen or optionally substituted C.sub.1-6 alkyl; R.sup.3 is an optionally substituted 5- or 6- membered heterocyclic group containing one or two nitrogen heteroatoms; or R.sup.2 and R.sup.3 together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6- membered heterocyclic group contaning one or two nitrogen heteroatoms; R.sup.4 is a substituted pyridinium group; and CO.sub.2 R is carboxy or a carboxylate anion; and also the use thereof.Processes for the preparation of the compounds are disclosed together with intermediates for use therein.Type: GrantFiled: August 8, 1986Date of Patent: July 10, 1990Assignee: Beecham Group p.l.c.Inventors: Stephen C. Finch, Michael J. Pearson
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Patent number: 4935508Abstract: A process for the selective formation of oximino o-protected derivatives of lower alkyl 2-(2-aminothiazol-4-yl)-2-oximinoacetates, and their use in the acylation of 7-amino-cephalosporin compounds is disclosed.Type: GrantFiled: August 23, 1988Date of Patent: June 19, 1990Assignee: Bristol-Myers CompanyInventors: Hajime Kamachi, Takaaki Okita, Satsuki Okuyama, Takayuki Naito
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Patent number: 4927922Abstract: 7.beta.-(Substituted)amino-3-substituted cephalosporanic acids, esters and salts, useful as anti-bacterial agents are described.Type: GrantFiled: July 21, 1988Date of Patent: May 22, 1990Assignee: American Cyanamid CompanyInventors: Ving J. Lee, William V. Curran
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Patent number: 4921954Abstract: Process for the preparation of 7.beta.-amino-3-substituted methyl-3-cephem-4-carboxylic acid derivatives, new intermediates comprising 7.beta.-(cyclo)alkylideneammonio-3-halomethyl-3-cephem-4-carbox ylic acid derivatives and 7.beta.-amino/ammonio-3-bromomethyl-3-cephem-4-carboxylic acid derivatives and the processes for the preparation of these intermediates.Type: GrantFiled: July 8, 1988Date of Patent: May 1, 1990Assignee: Gist-Brocades N.V.Inventors: Hendrik A. Witkamp, Jan Verweij, Jan J. DeKoning, Herman H. Grootveld, Everardus J. A. M. Leenderts
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Patent number: 4918070Abstract: A cephalosporin derivative having the formula: ##STR1## wherein R.sup.1 is a substituted amino group, X is an alkylene group, R.sup.2 is an aryl or heterocyclic group which may be substituted and R.sup.3 is a hydrogen atom, a negative charge or a residue of an ester which can form a pharmaceutically acceptable ester hydrolyzable in a living body; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: February 26, 1988Date of Patent: April 17, 1990Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Hiroshi Fukatsu, Yoshiaki Katoh, Satoshi Murase
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Patent number: 4912211Abstract: A process is described for producing pure crystalline products, in particular penicillin and cephalosporin, wherein the desired product, prepared according to a known method, is treated with ethanol in one or two steps, whereby the crystallization of the pure product and impurity separation are achieved.Type: GrantFiled: November 10, 1987Date of Patent: March 27, 1990Inventor: Giovanni Bonfanti
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Patent number: 4912212Abstract: Broad spectrum antibiotics are provided which are compounds of the formula: ##STR1## wherein -W-R is a residue of a nucleophilic compound and R.sup.5 is hydroxyl or protected hydroxyl, or a pharmaceutically acceptable salt or 4-carboxy ester which is the alkoxymethyl, .alpha.-alkoxyethyl, .alpha.-alkoxy-.alpha.-substituted methyl, alkylthiomethyl, acyloxymethyl or .alpha.-acyloxy-.alpha.-substituted methyl ester thereof.Type: GrantFiled: June 7, 1988Date of Patent: March 27, 1990Assignee: Takeda Chemical Industries, Ltd.Inventors: Michihiko Ochiai, Taiiti Okada, Osamu Aki, Akira Morimoto, Kenji Kawakita, Yoshihiro Matsushita
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Patent number: 4908443Abstract: Novel cephem compounds are provided which are useful for synthesizing cephamycin compounds useful as antibacterial agents. The novel compounds have the formula (I): ##STR1## wherein R.sup.1 represents a lower alkyl group and R.sup.2 represents an amino group which may be protected, in the salt thereof.Type: GrantFiled: May 23, 1989Date of Patent: March 13, 1990Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Masami Abe, Hideo Eiki
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Patent number: 4894371Abstract: An antibacterial cephalosporin derivative of the formula I: ##STR1## in which X is S,O,CH.sub.2 or S0; R2 is hydrogen, methoxy or formylamino; R3 is carboxy or a biodegradable ester thereof; R1 represents a variety of groups known in the cephalosporin art and R4 represents a group NR42R43 wherein R42 is hydrogen, lower alkyl or benzyl and R43 is one of a group of neutral heterocyclic species defined in the specification. Pharmaceutical compositions, manufacturing processes and intermediates are also described. In a specific embodiment, 3-substituted aminomethyl cephalosporin derivatives in which X is S or SO are disclosed.Type: GrantFiled: December 9, 1986Date of Patent: January 16, 1990Assignee: ICI PharmaInventor: Frederic H. Jung
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Patent number: 4877783Abstract: .beta.-Lactam antibiotics having an .alpha.-formamido substituent on the carbon atom adjacent to the carbonyl group of the .beta.-lactam ring and in particular bicyclic compounds having the partial structure: ##STR1## Intermediates and processes for the preparation of the compounds are further disclosed.Type: GrantFiled: January 24, 1985Date of Patent: October 31, 1989Assignee: Beecham Group p.l.c.Inventor: Peter H. Milner
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Patent number: 4835150Abstract: .beta.-Lactam antibiotics are disclosed which have the formula (IA) or pharmaceutically acceptable salts or pharmaceutically acceptable in vivo hydrolyzable esters thereof: ##STR1## wherein R.sub.1 is phenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 3-aminophenyl, 4-aminophenyl, or 3,4-dihydroxyphenyl, the hydroxy and amino groups being optionally protected, and R is C.sub.1-8 alkyl; and also the use thereof.Processes for the preparation of the compounds are disclosed together with intermediates for use therein.Type: GrantFiled: June 23, 1986Date of Patent: May 30, 1989Assignee: Beecham Group p.l.c.Inventors: Clive L. Branch, Arun C. Kaura
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Patent number: 4788185Abstract: A compound of the formula; ##STR1## wherein R.sup.0 stands for hydrogen atom, nitrogen-containing heterocyclic group, acyl group or esterified carboxyl group, Z stands for S, S.fwdarw.O, O or CH.sub.2, R.sup.4 stands for hydrogen atom, methoxy group or formamido group, R.sup.13 stands for hydrogen atom, methyl group, hydroxyl group or halogen atom and A stands for an optionally substituted imidazol-1-yl group forming a condensed ring at the 2,3- or 3,4-position or a physiologically or pharmaceutically acceptable salt or ester thereof.This compound is novel and has excellent antibacterial activity.Type: GrantFiled: April 23, 1985Date of Patent: November 29, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Masahiro Kondo, Masahiko Fujino
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Patent number: 4764606Abstract: A 7-formylaminocephalosporin compound represented by general formula (I): ##STR1## wherein R.sup.1 represents a carboxy group or an aminocarboxymethyl group ##STR2## R.sup.2 represents a hydrogen atom or a protective group for a carboxy group, andR.sup.3 represents a 5- or 6-membered heterocyclic group which may be substituted;or a salt thereof, and a process for producing the compound; The compounds are useful intermediates for other cephalosporin compounds having antibacterial activity, and themselves show antibacterial activity, as well.Type: GrantFiled: July 28, 1986Date of Patent: August 16, 1988Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Harumitsu Imai, Ken-ichi Suzuki, Koji Nagai, Shigeru Miyazaki, Kenji Abe, Isao Takahashi, Shigenobu Kadota, Koichi Tanaka
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Patent number: 4754030Abstract: The crystalline triethylamine salt of cefbuperazone is stable in the dry state and soluble in water and in aqueous injection vehicles.Type: GrantFiled: February 1, 1985Date of Patent: June 28, 1988Assignee: Bristol-Myers CompanyInventors: Murray A. Kaplan, Robert A. Lipper
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Patent number: 4748170Abstract: An antibacterial 7beta-(carboxyalkenoyl)amino-3-cephem-4-carboxylic acid represented by the following formula: ##STR1## (wherein R is aryl or a heterocyclic group; R.sup.1 is hydrogen or halogen;R.sup.2 is a single bond, alkylene, or thiaalkylene;R.sup.3 is a hydrogen atom or carboxy modifying group;R.sup.4 is hydrogen or methoxy;R.sup.5 is hydrogen or a 3-substituent of cephalosporins;R.sup.6 is a hydrogen atom or carboxy modifying group; andX is oxygen, sulfur, or sulfinyl)a pharmaceutical composition containing the same, and a method for treating a bacterial infection with the same.Type: GrantFiled: February 20, 1986Date of Patent: May 31, 1988Assignee: Shionogi & Co., Ltd.Inventor: Yoshio Hamashima
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Patent number: 4748163Abstract: Antibacterially active and animal growth-promoting novel .beta.-lactam compounds of the formula ##STR1## in which R.sup.1 represents the radical ##STR2## Y representing N or CR.sup.9, or Y--R.sup.7 representing >C.dbd.O or >C.dbd.N--R.sup.7,Z representing O, S, or NR.sup.10, andR.sup.2 represents hydrogen or a protective group.Type: GrantFiled: February 21, 1986Date of Patent: May 31, 1988Assignee: Bayer AktiengesellschaftInventors: Gunter Schmidt, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4734407Abstract: Antibacterially active and animal growth-regulating novel .beta.-lactam compounds of the formula ##STR1## in which R.sup.1 represents an optionally substituted radical of the formula ##STR2## Z represents oxygen, sulphur or --N--R.sup.Type: GrantFiled: March 10, 1986Date of Patent: March 29, 1988Assignee: Bayer AktiengesellschaftInventors: Gunter Schmidt, Hans-Joachim Zeiler, Karl G. Metzger
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Patent number: 4723004Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is ##STR2## HOOC--(CH.sub.2).sub.3 --CO-- or hydrogen, or a salt thereof, is useful as an intermediate for the production of cephem compounds, and some of them are useful as antimicrobial agents.Type: GrantFiled: December 14, 1984Date of Patent: February 2, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Setsuo Harada, Shigetoshi Tsubotani, Hideo Ono
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Patent number: 4690920Abstract: Disclosed herein are a derivative of a substituted cephalosporanic acid, represented by the formula (I): ##STR1## wherein p is 0, 1 or 2 and R.sup.1 represents a hydrogen atom, a hydroxyl group, a carbamoyl group, an alkyl group having 1 to 4 carbon atoms or --(CONH).sub.m (CH.sub.2).sub.n --COOH wherein m is 0 or 1; n is 0, 1 or 2 and the carboxyl group may have been converted to the salt or the ester thereof, and an antibiotic comprising a derivative of substituted cephalosporanic acid represented by the formula (I).Type: GrantFiled: December 20, 1983Date of Patent: September 1, 1987Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Akihiko Kanno, Shigeaki Muto, Koichi Niimura, Takao Ando, Takayoshi Fujii, Masahiko Fujii, Takao Furusho, Chikao Yoshikumi
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Patent number: 4684641Abstract: 7.alpha.-Hydroxyamino-7.beta.-[2-substituted-2-(acylamino)acetamido]-cephal osporin antibiotics, pharmaceutically-acceptable salts and in vivo hydrolyzable esters thereof, a method of treating susceptible infections therewith, and intermediates therefor.Type: GrantFiled: June 27, 1985Date of Patent: August 4, 1987Assignee: Pfizer Inc.Inventors: Colin W. Greengrass, David W. T. Hoople, Thomas T. Howarth
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Patent number: 4684639Abstract: A compound having the partial structure (I) ##STR1## wherein R.sup.1 and R.sup.2 may be the same or different and each is hydrogen or a group --COR.sup.5 or --CO--OR.sup.5 wherein R.sup.5 represents an optionally substituted hydrocarbon group; R.sup.3 is halogen and R.sup.4 is hydrogen, methoxy, hydroxymethyl or formamido.These compounds are suitably bicyclic .beta.-lactam antibiotics.Type: GrantFiled: July 5, 1984Date of Patent: August 4, 1987Assignee: Beecham GroupInventors: George Burton, Desmond J. Best
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Patent number: 4684642Abstract: 7.alpha.-Hydroxyamino-7.beta.-[2-substituted-2-(acylamino)acetamido]cephalo sporin antibiotics, pharmaceutically-acceptable salts and in vivo hydrolyzable esters thereof, a method of treating susceptible infections therewith, and intermediates therefor.Type: GrantFiled: March 5, 1986Date of Patent: August 4, 1987Assignee: Pfizer Inc.Inventors: Colin W. Greengrass, David W. T. Hoople, Thomas T. Howarth
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Patent number: 4673738Abstract: This invention relates to novel 7-(substituted or unsubstituted amino)-3-substituted methyl-.DELTA..sup.3 -cephem-4-carboxylic acids in which a substituted or unsubstituted 1,2,4-triazolyl or 2-(1,2,3,4-tetrazolyl) group attaches to the exomethylene group at the 3-position of the cephem ring through a carbon-nitrogen bond. These cephalosporins are useful intermediates for producing various novel cephalosporins. Also, this invention concerns a process for producing a compound represented by the formula: ##STR1## which comprises reacting a compound represented by the formula: ##STR2## with an optionally substituted triazole or tetrazole in the presence of an acid or a complex of the acid in an organic solvent at 0.degree. to 80.degree. C.Type: GrantFiled: September 26, 1984Date of Patent: June 16, 1987Assignee: Handi-Pac Inc.Inventors: Hiroshi Sadaki, Hirokazu Narita, Hiroyuki Imaizumi, Yoshinori Konishi, Takihiro Inaba, Tatsuo Hirakawa, Hideo Taki, Masaru Tai, Yasuo Watanabe, Isamu Saikawa
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Patent number: 4670431Abstract: A compound having the partial structure (A): ##STR1## wherein n is 1 or 2.Type: GrantFiled: January 19, 1984Date of Patent: June 2, 1987Assignee: Beecham Group p.l.c.Inventor: Peter H. Milner
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Patent number: 4656262Abstract: The 7-methoxy-3-heterocyclic thiomethyl cephalosporin derivative possessing excellent antimicrobial activity represented by the general formula ##STR1## wherein R.sup.1 represents ##STR2## group or HOOC-- group, R.sup.2 represents a nitrogen-containing heterocyclic group, and M represents a hydrogen atom or a cation residue forming a salt.Type: GrantFiled: December 13, 1985Date of Patent: April 7, 1987Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Takashi Osono, Yoshihiko Oka, Shunichi Watanabe, Takeshi Saito, Hiroshi Gushima, Keisuke Murakami, Isao Takahashi, Hiroshi Yamaguchi, Toshio Sasaki, Kiyoshi Susaki, Shuichi Takamura, Toshiaki Miyoshi
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Patent number: 4654331Abstract: The (5-R-2-oxo-1,3-dioxolen-4-yl)methyl moiety: ##STR1## wherein R is loweralkyl of 1-6 carbon atoms, especially methyl or t-butyl; when utilized as an ester on a pharmaceutical having a carboxylic acid functionality, enhances oral absorption of the pharmaceutical. This effect is applicable to a broad range of pharmaceutically active substances, including antibiotics, and antihypertensives as well as other classes of therapeutic agents.Type: GrantFiled: August 23, 1984Date of Patent: March 31, 1987Assignee: Merck & Co., Inc.Inventor: Burton G. Christensen
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Patent number: 4616081Abstract: Novel cephalosporin compounds having antibacterial activity, which are represented by the following compounds of the general formula (I), ##STR1## wherein R.sub.1 represents an amino group or a protected amino group;.circle.A represents a 5- or 6-membered heterocyclic ring containing therein 1 to 4 nitrogen, oxygen or sulfur atoms;R.sub.2 represents a normal alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms; a cycloalkenyl group having 3 to 6 carbon atoms; an aromatic organic residue; a 3- to 6-membered heterocyclic ring containing 1 to 4 nitrogen, sulfur or oxygen atoms or, ##STR2## wherein Ra and Rb each, which may be the same or different, represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;R.sub.Type: GrantFiled: July 6, 1983Date of Patent: October 7, 1986Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Joji Nishikido, Eiji Kodama, Chisei Shibuya
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Patent number: 4614797Abstract: An antibacterial cephalosporin hydroxamic acid derivative represented by the following formula (I), processes for its preparation, compositions containing the same as an active ingredient, and a method for killing bacteria by contacting with said compound. ##STR1## (wherein, R is acyl; R.sup.1 is hydrogen or methoxy; R.sup.2 is alkylene; R.sup.3 is hydrogen, aliphatic group or a hydroxy-protecting group; R.sup.4 is hydrogen or amino-protecting group; R.sup.5 is hydrogen, light metal atom or carboxy-protecting group; and X is oxygen, sulfur, or sulfinyl).Type: GrantFiled: February 2, 1984Date of Patent: September 30, 1986Assignee: Shionogi & Co., Ltd.Inventors: Wataru Nagata, Tsutomu Aoki, Yasuhiro Nishitani
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Patent number: 4609652Abstract: .beta.-Lactam antibiotics having an .alpha.-formamido substituent on the carbon atom adjacent to the carbonyl group of the .beta.-lactam ring and in particular bicyclic compounds having the partial structure: ##STR1## Intermediates and processes for the preparation of the compounds are further disclosed.Type: GrantFiled: January 24, 1985Date of Patent: September 2, 1986Assignee: Beecham Group p.l.c.Inventor: Peter H. Milner
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Patent number: RE32491Abstract: The invention relates to novel 7.alpha.-methoxycephalosporin derivatives having at the 7.beta.-position an amido group acylated by a 1,3-dithietane carboxylic acid residue and to 7.beta.-isothiazolylthioacetamido-7.alpha.-methoxycephalosporins having antibacterial activity by themselves and, as the case may be, capable of being converted into the aforesaid 7.alpha.-methoxycephalosporin derivatives. The compounds of this invention exhibit excellent antibacterial activity and are particularly effective against gram negative bacteria.Type: GrantFiled: April 25, 1985Date of Patent: September 1, 1987Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Masaru Iwanami, Tetsuya Maeda, Yoshinobu Nagano, Masaharu Fujimoto, Noriaki Nagano, Atsuki Yamazaki