Polymorph of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine
The invention relates to a compound which is, 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine, which is a selective A2A adenosine receptor agonist in myocardial imaging. The new polymorph of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine (designated as polymorph E) is characterized by...
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creator | Kvapil Lubomir Hradil Pavel Grepl Martin Dvorakova Barbora Slezar Petr |
description | The invention relates to a compound which is, 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine, which is a selective A2A adenosine receptor agonist in myocardial imaging. The new polymorph of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine (designated as polymorph E) is characterized by an X-ray diffraction pattern of X-RPD showing the following reflections at 2 Theta=5.8°, 12.3°, 15.9°, 17.3°, 20.5°, 22.6°, 23.6°, 27.7°, and 29.2°; and further characterized by a DSC scan showing marked endotherm in the range of 258 to 264° C.; and further characterized by a specific IR spectra. The invention further relates to a method of preparing the polymorph by recrystallization from other polymorphic forms of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine by a procedure comprising the following operations: mixing of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine with a polar aprotic solvent, preferably with dimethylsulfoxide, and heating to form a saturated solution; cooling of the saturated solution with formation of a turbid solution of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine; addition of the turbid solution of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine to a protic solvent, preferably methanol, with separation of a gel-like precipitate; heating of the separated gel-like precipitate in the protic solvent to a boil with formation of a suspension of polymorph E; and cooling of the suspension, isolation and drying of polymorph E. |
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The new polymorph of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine (designated as polymorph E) is characterized by an X-ray diffraction pattern of X-RPD showing the following reflections at 2 Theta=5.8°, 12.3°, 15.9°, 17.3°, 20.5°, 22.6°, 23.6°, 27.7°, and 29.2°; and further characterized by a DSC scan showing marked endotherm in the range of 258 to 264° C.; and further characterized by a specific IR spectra. The invention further relates to a method of preparing the polymorph by recrystallization from other polymorphic forms of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine by a procedure comprising the following operations: mixing of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine with a polar aprotic solvent, preferably with dimethylsulfoxide, and heating to form a saturated solution; cooling of the saturated solution with formation of a turbid solution of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine; addition of the turbid solution of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine to a protic solvent, preferably methanol, with separation of a gel-like precipitate; heating of the separated gel-like precipitate in the protic solvent to a boil with formation of a suspension of polymorph E; and cooling of the suspension, isolation and drying of polymorph E.</description><language>eng</language><subject>CHEMISTRY ; DERIVATIVES THEREOF ; METALLURGY ; NUCLEIC ACIDS ; NUCLEOSIDES ; NUCLEOTIDES ; ORGANIC CHEMISTRY ; SUGARS</subject><creationdate>2016</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20160913&DB=EPODOC&CC=US&NR=9441006B2$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,780,885,25564,76547</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20160913&DB=EPODOC&CC=US&NR=9441006B2$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>Kvapil Lubomir</creatorcontrib><creatorcontrib>Hradil Pavel</creatorcontrib><creatorcontrib>Grepl Martin</creatorcontrib><creatorcontrib>Dvorakova Barbora</creatorcontrib><creatorcontrib>Slezar Petr</creatorcontrib><title>Polymorph of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine</title><description>The invention relates to a compound which is, 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine, which is a selective A2A adenosine receptor agonist in myocardial imaging. The new polymorph of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine (designated as polymorph E) is characterized by an X-ray diffraction pattern of X-RPD showing the following reflections at 2 Theta=5.8°, 12.3°, 15.9°, 17.3°, 20.5°, 22.6°, 23.6°, 27.7°, and 29.2°; and further characterized by a DSC scan showing marked endotherm in the range of 258 to 264° C.; and further characterized by a specific IR spectra. The invention further relates to a method of preparing the polymorph by recrystallization from other polymorphic forms of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine by a procedure comprising the following operations: mixing of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine with a polar aprotic solvent, preferably with dimethylsulfoxide, and heating to form a saturated solution; cooling of the saturated solution with formation of a turbid solution of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine; addition of the turbid solution of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine to a protic solvent, preferably methanol, with separation of a gel-like precipitate; heating of the separated gel-like precipitate in the protic solvent to a boil with formation of a suspension of polymorph E; and cooling of the suspension, isolation and drying of polymorph E.</description><subject>CHEMISTRY</subject><subject>DERIVATIVES THEREOF</subject><subject>METALLURGY</subject><subject>NUCLEIC ACIDS</subject><subject>NUCLEOSIDES</subject><subject>NUCLEOTIDES</subject><subject>ORGANIC CHEMISTRY</subject><subject>SUGARS</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2016</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZHAOyM-pzM0vKshQyE9TMNKNNtGN1shNLcmozEnMzczL10xOLErKz6vMidU19NAtqCxKrMrP0TXUBQokpqTm5Rdn5qXyMLCmJeYUp_JCaW4GBTfXEGcP3dSC_PjU4oLE5NS81JL40GBLExNDAwMzJyNjIpQAAK0rMVc</recordid><startdate>20160913</startdate><enddate>20160913</enddate><creator>Kvapil Lubomir</creator><creator>Hradil Pavel</creator><creator>Grepl Martin</creator><creator>Dvorakova Barbora</creator><creator>Slezar Petr</creator><scope>EVB</scope></search><sort><creationdate>20160913</creationdate><title>Polymorph of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine</title><author>Kvapil Lubomir ; Hradil Pavel ; Grepl Martin ; Dvorakova Barbora ; Slezar Petr</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_US9441006B23</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng</language><creationdate>2016</creationdate><topic>CHEMISTRY</topic><topic>DERIVATIVES THEREOF</topic><topic>METALLURGY</topic><topic>NUCLEIC ACIDS</topic><topic>NUCLEOSIDES</topic><topic>NUCLEOTIDES</topic><topic>ORGANIC CHEMISTRY</topic><topic>SUGARS</topic><toplevel>online_resources</toplevel><creatorcontrib>Kvapil Lubomir</creatorcontrib><creatorcontrib>Hradil Pavel</creatorcontrib><creatorcontrib>Grepl Martin</creatorcontrib><creatorcontrib>Dvorakova Barbora</creatorcontrib><creatorcontrib>Slezar Petr</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>Kvapil Lubomir</au><au>Hradil Pavel</au><au>Grepl Martin</au><au>Dvorakova Barbora</au><au>Slezar Petr</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>Polymorph of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine</title><date>2016-09-13</date><risdate>2016</risdate><abstract>The invention relates to a compound which is, 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine, which is a selective A2A adenosine receptor agonist in myocardial imaging. The new polymorph of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine (designated as polymorph E) is characterized by an X-ray diffraction pattern of X-RPD showing the following reflections at 2 Theta=5.8°, 12.3°, 15.9°, 17.3°, 20.5°, 22.6°, 23.6°, 27.7°, and 29.2°; and further characterized by a DSC scan showing marked endotherm in the range of 258 to 264° C.; and further characterized by a specific IR spectra. The invention further relates to a method of preparing the polymorph by recrystallization from other polymorphic forms of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine by a procedure comprising the following operations: mixing of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine with a polar aprotic solvent, preferably with dimethylsulfoxide, and heating to form a saturated solution; cooling of the saturated solution with formation of a turbid solution of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine; addition of the turbid solution of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine to a protic solvent, preferably methanol, with separation of a gel-like precipitate; heating of the separated gel-like precipitate in the protic solvent to a boil with formation of a suspension of polymorph E; and cooling of the suspension, isolation and drying of polymorph E.</abstract><oa>free_for_read</oa></addata></record> |
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subjects | CHEMISTRY DERIVATIVES THEREOF METALLURGY NUCLEIC ACIDS NUCLEOSIDES NUCLEOTIDES ORGANIC CHEMISTRY SUGARS |
title | Polymorph of 2-[4-[(methylamino)carbonyl]-1H-pyrazol-1-yl]adenosine |
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