Studies on Novel Bone Resorption Inhibitors. I. Synthesis and Pharmacological Activities of Aminomethylenebisphosphonate Derivatives
A series of aminomethylenebisphosphonate derivatives was synthesized and evaluated for their antiresorptive activities using a parathyroid hormone (PTH)-induced hypercalemia model in rats (PIH model). Among these compounds, (cycloheptylamino)methylenebis(phosphonic acid) (3j) was finally selected fo...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1993/04/15, Vol.41(4), pp.688-693 |
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| container_end_page | 693 |
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| container_issue | 4 |
| container_start_page | 688 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 41 |
| creator | TAKEUCHI, Makoto SAKAMOTO, Shuichi YOSHIDA, Makoto ABE, Tetsushi ISOMURA, Yasuo |
| description | A series of aminomethylenebisphosphonate derivatives was synthesized and evaluated for their antiresorptive activities using a parathyroid hormone (PTH)-induced hypercalemia model in rats (PIH model). Among these compounds, (cycloheptylamino)methylenebis(phosphonic acid) (3j) was finally selected for further investigation, proving 10-fold as potent as pamidronate in the PIH model and an immobilization bone atrophy model in rats (DA model). The structure-activity relationships of this series of bisphosphonates are discussed. |
| doi_str_mv | 10.1248/cpb.41.688 |
| format | Article |
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The structure-activity relationships of this series of bisphosphonates are discussed.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.41.688</identifier><identifier>PMID: 8508470</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Animals ; bisphosphonate ; Bone Resorption - drug therapy ; bone resorption inhibitor ; Chemistry ; Diphosphonates - chemical synthesis ; Diphosphonates - therapeutic use ; etidronate ; Exact sciences and technology ; Hypercalcemia - drug therapy ; Male ; Organic chemistry ; Organometalloidal and organometallic compounds ; osteoporosis ; P derivatives ; pamidronate ; Preparations and properties ; Rats ; Rats, Wistar ; Structure-Activity Relationship ; YM175</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1993/04/15, Vol.41(4), pp.688-693</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1993 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1993</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=4860354$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8508470$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>TAKEUCHI, Makoto</creatorcontrib><creatorcontrib>SAKAMOTO, Shuichi</creatorcontrib><creatorcontrib>YOSHIDA, Makoto</creatorcontrib><creatorcontrib>ABE, Tetsushi</creatorcontrib><creatorcontrib>ISOMURA, Yasuo</creatorcontrib><title>Studies on Novel Bone Resorption Inhibitors. I. Synthesis and Pharmacological Activities of Aminomethylenebisphosphonate Derivatives</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A series of aminomethylenebisphosphonate derivatives was synthesized and evaluated for their antiresorptive activities using a parathyroid hormone (PTH)-induced hypercalemia model in rats (PIH model). Among these compounds, (cycloheptylamino)methylenebis(phosphonic acid) (3j) was finally selected for further investigation, proving 10-fold as potent as pamidronate in the PIH model and an immobilization bone atrophy model in rats (DA model). The structure-activity relationships of this series of bisphosphonates are discussed.</description><subject>Animals</subject><subject>bisphosphonate</subject><subject>Bone Resorption - drug therapy</subject><subject>bone resorption inhibitor</subject><subject>Chemistry</subject><subject>Diphosphonates - chemical synthesis</subject><subject>Diphosphonates - therapeutic use</subject><subject>etidronate</subject><subject>Exact sciences and technology</subject><subject>Hypercalcemia - drug therapy</subject><subject>Male</subject><subject>Organic chemistry</subject><subject>Organometalloidal and organometallic compounds</subject><subject>osteoporosis</subject><subject>P derivatives</subject><subject>pamidronate</subject><subject>Preparations and properties</subject><subject>Rats</subject><subject>Rats, Wistar</subject><subject>Structure-Activity Relationship</subject><subject>YM175</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1993</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkd2L1DAUxYMo6-zqi-9CQNm31jQfTfo4jl8Di4qrzyVNb7cZ2mQ2SQfm3T_crDOs4EMSyPlx7uUchF5VpKwoV-_Mvit5VdZKPUGrinFZCErZU7QihDQFZTV7ji5j3BFCBZHsAl0oQRSXZIV-36altxCxd_irP8CE33sH-AdEH_bJ5t-tG21nkw-xxNsS3x5dGiHaiLXr8fdRh1kbP_k7a_SE1ybZg01_DQe8nq3zM6TxOIGDzsb96B-O0wnwBwj2oDMO8QV6Nugpwsvze4V-ffr4c_OluPn2ebtZ3xQ7WstUUMFoTYyqBOGNFA1TjeCKqKYmNTXN0AngvSHqIRNdCam17EEOtGpILQEIu0LXJ9998PcLxNTONhqYJu3AL7GVQkraMJnBN_-BO78El3drK14TqmQemanXZ2rpZujbfbCzDsf2HG7W3551HXM4Q9DO2PiIcVUTJnjGNidsF5O-g0ddh2TNBG1ut2qEannV8tOVi_6n5gZacOwPE5Wfvg</recordid><startdate>199304</startdate><enddate>199304</enddate><creator>TAKEUCHI, Makoto</creator><creator>SAKAMOTO, Shuichi</creator><creator>YOSHIDA, Makoto</creator><creator>ABE, Tetsushi</creator><creator>ISOMURA, Yasuo</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>199304</creationdate><title>Studies on Novel Bone Resorption Inhibitors. I. Synthesis and Pharmacological Activities of Aminomethylenebisphosphonate Derivatives</title><author>TAKEUCHI, Makoto ; SAKAMOTO, Shuichi ; YOSHIDA, Makoto ; ABE, Tetsushi ; ISOMURA, Yasuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-j267t-253260c8150497593895480896062c9fb5e4dc081248a157aa7de7f219067ee03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1993</creationdate><topic>Animals</topic><topic>bisphosphonate</topic><topic>Bone Resorption - drug therapy</topic><topic>bone resorption inhibitor</topic><topic>Chemistry</topic><topic>Diphosphonates - chemical synthesis</topic><topic>Diphosphonates - therapeutic use</topic><topic>etidronate</topic><topic>Exact sciences and technology</topic><topic>Hypercalcemia - drug therapy</topic><topic>Male</topic><topic>Organic chemistry</topic><topic>Organometalloidal and organometallic compounds</topic><topic>osteoporosis</topic><topic>P derivatives</topic><topic>pamidronate</topic><topic>Preparations and properties</topic><topic>Rats</topic><topic>Rats, Wistar</topic><topic>Structure-Activity Relationship</topic><topic>YM175</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>TAKEUCHI, Makoto</creatorcontrib><creatorcontrib>SAKAMOTO, Shuichi</creatorcontrib><creatorcontrib>YOSHIDA, Makoto</creatorcontrib><creatorcontrib>ABE, Tetsushi</creatorcontrib><creatorcontrib>ISOMURA, Yasuo</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>TAKEUCHI, Makoto</au><au>SAKAMOTO, Shuichi</au><au>YOSHIDA, Makoto</au><au>ABE, Tetsushi</au><au>ISOMURA, Yasuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Studies on Novel Bone Resorption Inhibitors. I. Synthesis and Pharmacological Activities of Aminomethylenebisphosphonate Derivatives</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1993-04</date><risdate>1993</risdate><volume>41</volume><issue>4</issue><spage>688</spage><epage>693</epage><pages>688-693</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>A series of aminomethylenebisphosphonate derivatives was synthesized and evaluated for their antiresorptive activities using a parathyroid hormone (PTH)-induced hypercalemia model in rats (PIH model). Among these compounds, (cycloheptylamino)methylenebis(phosphonic acid) (3j) was finally selected for further investigation, proving 10-fold as potent as pamidronate in the PIH model and an immobilization bone atrophy model in rats (DA model). The structure-activity relationships of this series of bisphosphonates are discussed.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>8508470</pmid><doi>10.1248/cpb.41.688</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 1993/04/15, Vol.41(4), pp.688-693 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Animals bisphosphonate Bone Resorption - drug therapy bone resorption inhibitor Chemistry Diphosphonates - chemical synthesis Diphosphonates - therapeutic use etidronate Exact sciences and technology Hypercalcemia - drug therapy Male Organic chemistry Organometalloidal and organometallic compounds osteoporosis P derivatives pamidronate Preparations and properties Rats Rats, Wistar Structure-Activity Relationship YM175 |
| title | Studies on Novel Bone Resorption Inhibitors. I. Synthesis and Pharmacological Activities of Aminomethylenebisphosphonate Derivatives |
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