Studies of non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: synthesis and structure-activity relationships of 2-cyano and 2-hydroxy thiazolidenebenzenesulfonamide derivatives.
Identifieur interne : 000D46 ( Ncbi/Merge ); précédent : 000D45; suivant : 000D47Studies of non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: synthesis and structure-activity relationships of 2-cyano and 2-hydroxy thiazolidenebenzenesulfonamide derivatives.
Auteurs : Naoyuki Masuda [Japon] ; Osamu Yamamoto ; Masahiro Fujii ; Tetsuro Ohgami ; Jiro Fujiyasu ; Toru Kontani ; Ayako Moritomo ; Masaya Orita ; Hiroyuki Kurihara ; Hironobu Koga ; Shunji Kageyama ; Mitsuaki Ohta ; Hiroshi Inoue ; Toshifumi Hatta ; Masafumi Shintani ; Hiroshi Suzuki ; Kenji Sudo ; Yasuaki Shimizu ; Eiichi Kodama ; Masao Matsuoka ; Masatoshi Fujiwara ; Tomoyuki Yokota ; Shiro Shigeta ; Masanori BabaSource :
- Bioorganic & medicinal chemistry [ 0968-0896 ] ; 2005.
Descripteurs français
- KwdFr :
- Humains, Inhibiteurs de la transcriptase inverse (), Inhibiteurs de la transcriptase inverse (pharmacologie), Inhibiteurs de la transcriptase inverse (synthèse chimique), Lignée cellulaire, Relation structure-activité, Spectrométrie de masse FAB, Spectroscopie par résonance magnétique, Sulfonamides (), Sulfonamides (pharmacologie), Sulfonamides (synthèse chimique), Tests de sensibilité microbienne, VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ().
- MESH :
- pharmacologie : Inhibiteurs de la transcriptase inverse, Sulfonamides.
- synthèse chimique : Inhibiteurs de la transcriptase inverse, Sulfonamides.
- Humains, Inhibiteurs de la transcriptase inverse, Lignée cellulaire, Relation structure-activité, Spectrométrie de masse FAB, Spectroscopie par résonance magnétique, Sulfonamides, Tests de sensibilité microbienne, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
English descriptors
- KwdEn :
- Cell Line, HIV-1 (drug effects), Humans, Magnetic Resonance Spectroscopy, Microbial Sensitivity Tests, Reverse Transcriptase Inhibitors (chemical synthesis), Reverse Transcriptase Inhibitors (chemistry), Reverse Transcriptase Inhibitors (pharmacology), Spectrometry, Mass, Fast Atom Bombardment, Structure-Activity Relationship, Sulfonamides (chemical synthesis), Sulfonamides (chemistry), Sulfonamides (pharmacology).
- MESH :
- chemical , chemical synthesis : Reverse Transcriptase Inhibitors, Sulfonamides.
- chemical , chemistry : Reverse Transcriptase Inhibitors, Sulfonamides.
- drug effects : HIV-1.
- chemical , pharmacology : Reverse Transcriptase Inhibitors, Sulfonamides.
- Cell Line, Humans, Magnetic Resonance Spectroscopy, Microbial Sensitivity Tests, Spectrometry, Mass, Fast Atom Bombardment, Structure-Activity Relationship.
Abstract
In a previous study, we described the structure-activity relationships (SARs) for a series of thiazolidenebenzenesulfonamide derivatives. These compounds were found to be highly potent inhibitors of the wild type (WT) and Y181C mutant reverse transcriptases (RTs) and modest inhibitors of K103N RT. These molecules are thus considered to be a novel class of non-nucleoside HIV-1 RT inhibitors (NNRTIs). In this paper, we have examined the effects of substituents on both the thiazolidene and benzenesulfonamide moieties. Introduction of a 2-cyanophenyl ring into these moieties significantly enhanced anti-HIV-1 activity, whereas a 2-hydroxyphenyl group endowed potent activity against RTs, including K103N and Y181C mutants. Among the series of molecules examined, 10l and 18b (YM-228855), combinations of 2-cyanophenyl and 4-methyl-5-isopropylthiazole moieties, showed extremely potent anti-HIV-1 activity. The EC50 values of 101 and 18b were 0.0017 and 0.0018 microM, respectively. These values were lower than that of efavirenz (3). Compound 11g (YM-215389), a combination of 2-hydroxyphenyl and 4-chloro-5-isopropylthiazole moieties, proved to be the most active against both K103N and Y181C RTs with IC50 values of 0.043 and 0.013 microM, respectively.
DOI: 10.1016/j.bmc.2004.11.045
PubMed: 15670903
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pubmed:15670903Le document en format XML
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Part 2: synthesis and structure-activity relationships of 2-cyano and 2-hydroxy thiazolidenebenzenesulfonamide derivatives.</title><author><name sortKey="Masuda, Naoyuki" sort="Masuda, Naoyuki" uniqKey="Masuda N" first="Naoyuki" last="Masuda">Naoyuki Masuda</name><affiliation wicri:level="1"><nlm:affiliation>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd, 21 Miyukigaoka, Tsukuba, Ibaraki 305-8585, Japan. masuda.naoyuki@yamanouchi.co.jp</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd, 21 Miyukigaoka, Tsukuba, Ibaraki 305-8585</wicri:regionArea><wicri:noRegion>Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Yamamoto, Osamu" sort="Yamamoto, Osamu" uniqKey="Yamamoto O" first="Osamu" last="Yamamoto">Osamu Yamamoto</name></author><author><name sortKey="Fujii, Masahiro" sort="Fujii, Masahiro" uniqKey="Fujii M" first="Masahiro" last="Fujii">Masahiro Fujii</name></author><author><name sortKey="Ohgami, Tetsuro" sort="Ohgami, Tetsuro" uniqKey="Ohgami T" first="Tetsuro" last="Ohgami">Tetsuro Ohgami</name></author><author><name sortKey="Fujiyasu, Jiro" sort="Fujiyasu, Jiro" uniqKey="Fujiyasu J" first="Jiro" last="Fujiyasu">Jiro Fujiyasu</name></author><author><name sortKey="Kontani, Toru" sort="Kontani, Toru" uniqKey="Kontani T" first="Toru" last="Kontani">Toru Kontani</name></author><author><name sortKey="Moritomo, Ayako" sort="Moritomo, Ayako" uniqKey="Moritomo A" first="Ayako" last="Moritomo">Ayako Moritomo</name></author><author><name sortKey="Orita, Masaya" sort="Orita, Masaya" uniqKey="Orita M" first="Masaya" last="Orita">Masaya Orita</name></author><author><name sortKey="Kurihara, Hiroyuki" sort="Kurihara, Hiroyuki" uniqKey="Kurihara H" first="Hiroyuki" last="Kurihara">Hiroyuki Kurihara</name></author><author><name sortKey="Koga, Hironobu" sort="Koga, Hironobu" uniqKey="Koga H" first="Hironobu" last="Koga">Hironobu Koga</name></author><author><name sortKey="Kageyama, Shunji" sort="Kageyama, Shunji" uniqKey="Kageyama S" first="Shunji" last="Kageyama">Shunji Kageyama</name></author><author><name sortKey="Ohta, Mitsuaki" sort="Ohta, Mitsuaki" uniqKey="Ohta M" first="Mitsuaki" last="Ohta">Mitsuaki Ohta</name></author><author><name sortKey="Inoue, Hiroshi" sort="Inoue, Hiroshi" uniqKey="Inoue H" first="Hiroshi" last="Inoue">Hiroshi Inoue</name></author><author><name sortKey="Hatta, Toshifumi" sort="Hatta, Toshifumi" uniqKey="Hatta T" first="Toshifumi" last="Hatta">Toshifumi Hatta</name></author><author><name sortKey="Shintani, Masafumi" sort="Shintani, Masafumi" uniqKey="Shintani M" first="Masafumi" last="Shintani">Masafumi Shintani</name></author><author><name sortKey="Suzuki, Hiroshi" sort="Suzuki, Hiroshi" uniqKey="Suzuki H" first="Hiroshi" last="Suzuki">Hiroshi Suzuki</name></author><author><name sortKey="Sudo, Kenji" sort="Sudo, Kenji" uniqKey="Sudo K" first="Kenji" last="Sudo">Kenji Sudo</name></author><author><name sortKey="Shimizu, Yasuaki" sort="Shimizu, Yasuaki" uniqKey="Shimizu Y" first="Yasuaki" last="Shimizu">Yasuaki Shimizu</name></author><author><name sortKey="Kodama, Eiichi" sort="Kodama, Eiichi" uniqKey="Kodama E" first="Eiichi" last="Kodama">Eiichi Kodama</name></author><author><name sortKey="Matsuoka, Masao" sort="Matsuoka, Masao" uniqKey="Matsuoka M" first="Masao" last="Matsuoka">Masao Matsuoka</name></author><author><name sortKey="Fujiwara, Masatoshi" sort="Fujiwara, Masatoshi" uniqKey="Fujiwara M" first="Masatoshi" last="Fujiwara">Masatoshi Fujiwara</name></author><author><name sortKey="Yokota, Tomoyuki" sort="Yokota, Tomoyuki" uniqKey="Yokota T" first="Tomoyuki" last="Yokota">Tomoyuki Yokota</name></author><author><name sortKey="Shigeta, Shiro" sort="Shigeta, Shiro" uniqKey="Shigeta S" first="Shiro" last="Shigeta">Shiro Shigeta</name></author><author><name sortKey="Baba, Masanori" sort="Baba, Masanori" uniqKey="Baba M" first="Masanori" last="Baba">Masanori Baba</name></author></analytic><series><title level="j">Bioorganic & medicinal chemistry</title><idno type="ISSN">0968-0896</idno><imprint><date when="2005" type="published">2005</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Cell Line</term><term>HIV-1 (drug effects)</term><term>Humans</term><term>Magnetic Resonance Spectroscopy</term><term>Microbial Sensitivity Tests</term><term>Reverse Transcriptase Inhibitors (chemical synthesis)</term><term>Reverse Transcriptase Inhibitors (chemistry)</term><term>Reverse Transcriptase Inhibitors (pharmacology)</term><term>Spectrometry, Mass, Fast Atom Bombardment</term><term>Structure-Activity Relationship</term><term>Sulfonamides (chemical synthesis)</term><term>Sulfonamides (chemistry)</term><term>Sulfonamides (pharmacology)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Humains</term><term>Inhibiteurs de la transcriptase inverse ()</term><term>Inhibiteurs de la transcriptase inverse (pharmacologie)</term><term>Inhibiteurs de la transcriptase inverse (synthèse chimique)</term><term>Lignée cellulaire</term><term>Relation structure-activité</term><term>Spectrométrie de masse FAB</term><term>Spectroscopie par résonance magnétique</term><term>Sulfonamides ()</term><term>Sulfonamides (pharmacologie)</term><term>Sulfonamides (synthèse chimique)</term><term>Tests de sensibilité microbienne</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Reverse Transcriptase Inhibitors</term><term>Sulfonamides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Reverse Transcriptase Inhibitors</term><term>Sulfonamides</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Inhibiteurs de la transcriptase inverse</term><term>Sulfonamides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Reverse Transcriptase Inhibitors</term><term>Sulfonamides</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Inhibiteurs de la transcriptase inverse</term><term>Sulfonamides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Cell Line</term><term>Humans</term><term>Magnetic Resonance Spectroscopy</term><term>Microbial Sensitivity Tests</term><term>Spectrometry, Mass, Fast Atom Bombardment</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Humains</term><term>Inhibiteurs de la transcriptase inverse</term><term>Lignée cellulaire</term><term>Relation structure-activité</term><term>Spectrométrie de masse FAB</term><term>Spectroscopie par résonance magnétique</term><term>Sulfonamides</term><term>Tests de sensibilité microbienne</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">In a previous study, we described the structure-activity relationships (SARs) for a series of thiazolidenebenzenesulfonamide derivatives. These compounds were found to be highly potent inhibitors of the wild type (WT) and Y181C mutant reverse transcriptases (RTs) and modest inhibitors of K103N RT. These molecules are thus considered to be a novel class of non-nucleoside HIV-1 RT inhibitors (NNRTIs). In this paper, we have examined the effects of substituents on both the thiazolidene and benzenesulfonamide moieties. Introduction of a 2-cyanophenyl ring into these moieties significantly enhanced anti-HIV-1 activity, whereas a 2-hydroxyphenyl group endowed potent activity against RTs, including K103N and Y181C mutants. Among the series of molecules examined, 10l and 18b (YM-228855), combinations of 2-cyanophenyl and 4-methyl-5-isopropylthiazole moieties, showed extremely potent anti-HIV-1 activity. The EC50 values of 101 and 18b were 0.0017 and 0.0018 microM, respectively. These values were lower than that of efavirenz (3). Compound 11g (YM-215389), a combination of 2-hydroxyphenyl and 4-chloro-5-isopropylthiazole moieties, proved to be the most active against both K103N and Y181C RTs with IC50 values of 0.043 and 0.013 microM, respectively.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">15670903</PMID><DateCompleted><Year>2005</Year><Month>08</Month><Day>02</Day></DateCompleted><DateRevised><Year>2005</Year><Month>01</Month><Day>26</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0968-0896</ISSN><JournalIssue CitedMedium="Print"><Volume>13</Volume><Issue>4</Issue><PubDate><Year>2005</Year><Month>Feb</Month><Day>15</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry</Title><ISOAbbreviation>Bioorg. Med. Chem.</ISOAbbreviation></Journal><ArticleTitle>Studies of non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: synthesis and structure-activity relationships of 2-cyano and 2-hydroxy thiazolidenebenzenesulfonamide derivatives.</ArticleTitle><Pagination><MedlinePgn>949-61</MedlinePgn></Pagination><Abstract><AbstractText>In a previous study, we described the structure-activity relationships (SARs) for a series of thiazolidenebenzenesulfonamide derivatives. These compounds were found to be highly potent inhibitors of the wild type (WT) and Y181C mutant reverse transcriptases (RTs) and modest inhibitors of K103N RT. These molecules are thus considered to be a novel class of non-nucleoside HIV-1 RT inhibitors (NNRTIs). In this paper, we have examined the effects of substituents on both the thiazolidene and benzenesulfonamide moieties. Introduction of a 2-cyanophenyl ring into these moieties significantly enhanced anti-HIV-1 activity, whereas a 2-hydroxyphenyl group endowed potent activity against RTs, including K103N and Y181C mutants. Among the series of molecules examined, 10l and 18b (YM-228855), combinations of 2-cyanophenyl and 4-methyl-5-isopropylthiazole moieties, showed extremely potent anti-HIV-1 activity. The EC50 values of 101 and 18b were 0.0017 and 0.0018 microM, respectively. These values were lower than that of efavirenz (3). Compound 11g (YM-215389), a combination of 2-hydroxyphenyl and 4-chloro-5-isopropylthiazole moieties, proved to be the most active against both K103N and Y181C RTs with IC50 values of 0.043 and 0.013 microM, respectively.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Masuda</LastName><ForeName>Naoyuki</ForeName><Initials>N</Initials><AffiliationInfo><Affiliation>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd, 21 Miyukigaoka, Tsukuba, Ibaraki 305-8585, Japan. masuda.naoyuki@yamanouchi.co.jp</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Yamamoto</LastName><ForeName>Osamu</ForeName><Initials>O</Initials></Author><Author ValidYN="Y"><LastName>Fujii</LastName><ForeName>Masahiro</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Ohgami</LastName><ForeName>Tetsuro</ForeName><Initials>T</Initials></Author><Author ValidYN="Y"><LastName>Fujiyasu</LastName><ForeName>Jiro</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Kontani</LastName><ForeName>Toru</ForeName><Initials>T</Initials></Author><Author ValidYN="Y"><LastName>Moritomo</LastName><ForeName>Ayako</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Orita</LastName><ForeName>Masaya</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Kurihara</LastName><ForeName>Hiroyuki</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Koga</LastName><ForeName>Hironobu</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Kageyama</LastName><ForeName>Shunji</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Ohta</LastName><ForeName>Mitsuaki</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Inoue</LastName><ForeName>Hiroshi</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Hatta</LastName><ForeName>Toshifumi</ForeName><Initials>T</Initials></Author><Author ValidYN="Y"><LastName>Shintani</LastName><ForeName>Masafumi</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Suzuki</LastName><ForeName>Hiroshi</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Sudo</LastName><ForeName>Kenji</ForeName><Initials>K</Initials></Author><Author ValidYN="Y"><LastName>Shimizu</LastName><ForeName>Yasuaki</ForeName><Initials>Y</Initials></Author><Author ValidYN="Y"><LastName>Kodama</LastName><ForeName>Eiichi</ForeName><Initials>E</Initials></Author><Author ValidYN="Y"><LastName>Matsuoka</LastName><ForeName>Masao</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Fujiwara</LastName><ForeName>Masatoshi</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Yokota</LastName><ForeName>Tomoyuki</ForeName><Initials>T</Initials></Author><Author ValidYN="Y"><LastName>Shigeta</LastName><ForeName>Shiro</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Baba</LastName><ForeName>Masanori</ForeName><Initials>M</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Bioorg Med Chem</MedlineTA><NlmUniqueID>9413298</NlmUniqueID><ISSNLinking>0968-0896</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D018894">Reverse Transcriptase Inhibitors</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D013449">Sulfonamides</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D002460" MajorTopicYN="N">Cell Line</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015497" MajorTopicYN="N">HIV-1</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009682" MajorTopicYN="N">Magnetic Resonance Spectroscopy</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018894" MajorTopicYN="N">Reverse Transcriptase Inhibitors</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D016339" MajorTopicYN="N">Spectrometry, Mass, Fast Atom Bombardment</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013449" MajorTopicYN="N">Sulfonamides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2004</Year><Month>10</Month><Day>13</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2004</Year><Month>11</Month><Day>24</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2004</Year><Month>11</Month><Day>24</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2005</Year><Month>1</Month><Day>27</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2005</Year><Month>8</Month><Day>3</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2005</Year><Month>1</Month><Day>27</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">15670903</ArticleId><ArticleId IdType="pii">S0968-0896(04)00946-0</ArticleId><ArticleId IdType="doi">10.1016/j.bmc.2004.11.045</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Japon</li></country></list><tree><noCountry><name sortKey="Baba, Masanori" sort="Baba, Masanori" uniqKey="Baba M" first="Masanori" last="Baba">Masanori Baba</name><name sortKey="Fujii, Masahiro" sort="Fujii, Masahiro" uniqKey="Fujii M" first="Masahiro" last="Fujii">Masahiro Fujii</name><name sortKey="Fujiwara, Masatoshi" sort="Fujiwara, Masatoshi" uniqKey="Fujiwara M" first="Masatoshi" last="Fujiwara">Masatoshi Fujiwara</name><name sortKey="Fujiyasu, Jiro" sort="Fujiyasu, Jiro" uniqKey="Fujiyasu J" first="Jiro" last="Fujiyasu">Jiro Fujiyasu</name><name sortKey="Hatta, Toshifumi" sort="Hatta, Toshifumi" uniqKey="Hatta T" first="Toshifumi" last="Hatta">Toshifumi Hatta</name><name sortKey="Inoue, Hiroshi" sort="Inoue, Hiroshi" uniqKey="Inoue H" first="Hiroshi" last="Inoue">Hiroshi Inoue</name><name sortKey="Kageyama, Shunji" sort="Kageyama, Shunji" uniqKey="Kageyama S" first="Shunji" last="Kageyama">Shunji Kageyama</name><name sortKey="Kodama, Eiichi" sort="Kodama, Eiichi" uniqKey="Kodama E" first="Eiichi" last="Kodama">Eiichi Kodama</name><name sortKey="Koga, Hironobu" sort="Koga, Hironobu" uniqKey="Koga H" first="Hironobu" last="Koga">Hironobu Koga</name><name sortKey="Kontani, Toru" sort="Kontani, Toru" uniqKey="Kontani T" first="Toru" last="Kontani">Toru Kontani</name><name sortKey="Kurihara, Hiroyuki" sort="Kurihara, Hiroyuki" uniqKey="Kurihara H" first="Hiroyuki" last="Kurihara">Hiroyuki Kurihara</name><name sortKey="Matsuoka, Masao" sort="Matsuoka, Masao" uniqKey="Matsuoka M" first="Masao" last="Matsuoka">Masao Matsuoka</name><name sortKey="Moritomo, Ayako" sort="Moritomo, Ayako" uniqKey="Moritomo A" first="Ayako" last="Moritomo">Ayako Moritomo</name><name sortKey="Ohgami, Tetsuro" sort="Ohgami, Tetsuro" uniqKey="Ohgami T" first="Tetsuro" last="Ohgami">Tetsuro Ohgami</name><name sortKey="Ohta, Mitsuaki" sort="Ohta, Mitsuaki" uniqKey="Ohta M" first="Mitsuaki" last="Ohta">Mitsuaki Ohta</name><name sortKey="Orita, Masaya" sort="Orita, Masaya" uniqKey="Orita M" first="Masaya" last="Orita">Masaya Orita</name><name sortKey="Shigeta, Shiro" sort="Shigeta, Shiro" uniqKey="Shigeta S" first="Shiro" last="Shigeta">Shiro Shigeta</name><name sortKey="Shimizu, Yasuaki" sort="Shimizu, Yasuaki" uniqKey="Shimizu Y" first="Yasuaki" last="Shimizu">Yasuaki Shimizu</name><name sortKey="Shintani, Masafumi" sort="Shintani, Masafumi" uniqKey="Shintani M" first="Masafumi" last="Shintani">Masafumi Shintani</name><name sortKey="Sudo, Kenji" sort="Sudo, Kenji" uniqKey="Sudo K" first="Kenji" last="Sudo">Kenji Sudo</name><name sortKey="Suzuki, Hiroshi" sort="Suzuki, Hiroshi" uniqKey="Suzuki H" first="Hiroshi" last="Suzuki">Hiroshi Suzuki</name><name sortKey="Yamamoto, Osamu" sort="Yamamoto, Osamu" uniqKey="Yamamoto O" first="Osamu" last="Yamamoto">Osamu Yamamoto</name><name sortKey="Yokota, Tomoyuki" sort="Yokota, Tomoyuki" uniqKey="Yokota T" first="Tomoyuki" last="Yokota">Tomoyuki Yokota</name></noCountry><country name="Japon"><noRegion><name sortKey="Masuda, Naoyuki" sort="Masuda, Naoyuki" uniqKey="Masuda N" first="Naoyuki" last="Masuda">Naoyuki Masuda</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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