{"search_session":{},"preferences":{"l":"en","queryLanguage":"en"},"patentId":"US_6590107_B1","frontPageModel":{"patentViewModel":{"ref":{"entityRefId":"069-224-945-852-349","entityRefType":"PATENT"},"entityMetadata":{"linkedIds":{"empty":true},"tags":[],"collections":[{"id":11617,"type":"PATENT","title":"Emory University - Patent Portfolio","description":"","access":"OPEN_ACCESS","displayAvatar":true,"attested":false,"itemCount":6117,"tags":[],"user":{"id":91044780,"username":"Cambialens","firstName":"","lastName":"","created":"2015-05-04T00:55:26.000Z","displayName":"Cambialens","preferences":"{\"usage\":\"public\",\"beta\":false}","accountType":"PERSONAL","isOauthOnly":false},"notes":[{"id":8292,"type":"COLLECTION","user":{"id":91044780,"username":"Cambialens","firstName":"","lastName":"","created":"2015-05-04T00:55:26.000Z","displayName":"Cambialens","preferences":"{\"usage\":\"public\",\"beta\":false}","accountType":"PERSONAL","isOauthOnly":false},"text":"
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(a) preparing a selenol dimer of the formula (SeCH 2 COOH) 2 ;
(b) reducing said dimer; and
(c) coupling the reduction product with ROCH 2 CHO to form the 1,3-oxaselenolane lactone."],"number":2,"annotation":false,"claim":true,"title":false},{"lines":["The process of claim 2 , wherein ROCH 2 CHO is BzOCH 2 CHO."],"number":3,"annotation":false,"claim":true,"title":false},{"lines":["The process of claim 2 , wherein the reduction and coupling are achieved without isolating any intermediates."],"number":4,"annotation":false,"claim":true,"title":false},{"lines":["The process of any one of claims 2 - 4 , wherein the reduction is achieved using H 3 PO 2 ."],"number":5,"annotation":false,"claim":true,"title":false},{"lines":["The process of claim 2 , wherein the selenol dimer is prepared from a selenyl cyanide comprising:
(a) coupling a selenyl cyanide of the formula KSeCN with Br—CH 2 CO 2 Et to form NCSeCH 2 CO 2 Et;
(b) dimerizing NCSeCH 2 CO 2 Et to form (SeCH 2 CO 2 Et) 2 ; and if necessary
(c) activating (SeCH 2 CO 2 Et) 2 to form (SeCH 2 CO 2 H) 2 ."],"number":6,"annotation":false,"claim":true,"title":false},{"lines":["A process for preparing a 1,3-oxaselenolane nucleoside of the formula: wherein B is a purine or pyrimidine base, and R is hydrogen, acyl, a mono-, di- or triphosphate ester, or an ether lipid, or a pharmaceutically acceptable salt thereof, comprising:
(a) preparing a 1,3-oxaselenolane lactone of formula:
(b) activating said lactone to a compound of the formula:
wherein L is an appropriate leaving group, halogen or acyl;
(c) coupling the activated lactone with an optionally silylated base to form a 1,3-oxaselenolane nucleoside; and if necessary
(d) deprotecting said nucleoside to form a 1,3-oxaselenolane nucleoside of the x formula:
wherein B is a purine or pyrimidine base, and R is hydrogen; and optionally
(e) activating said nucleoside to form a 1,3-oxaselenolane nucleoside of the formula:
wherein B is a purine or pyrimidine base, and R acyl, a mono-, di- or triphosphate ester, or an ether lipid, or a pharmaceutically acceptable salt thereof."],"number":7,"annotation":false,"claim":true,"title":false},{"lines":["The process of claim 7 , wherein the coupling is achieved in the presence of trimethylsilyltriflate."],"number":8,"annotation":false,"claim":true,"title":false},{"lines":["The process of claim 7 , wherein L is acyl."],"number":9,"annotation":false,"claim":true,"title":false},{"lines":["The process of claim 9 wherein L is acetyl."],"number":10,"annotation":false,"claim":true,"title":false},{"lines":["The process of claim 9 or 10 , wherein the activated lactone is prepared from the lactone comprising:
(a) reducing the lactone with a reducing agent to form an alcohol of the formula:
(b) activating the alcohol to form the activated compound of the formula:"],"number":11,"annotation":false,"claim":true,"title":false},{"lines":["The process of claim 10 , wherein the reducing agent is DIBAL-H."],"number":12,"annotation":false,"claim":true,"title":false},{"lines":["The process of claim 10 , wherein the activation of the alcohol is achieved with acetic anhydride."],"number":13,"annotation":false,"claim":true,"title":false}]}},"filters":{"npl":[],"notNpl":[],"applicant":[],"notApplicant":[],"inventor":[],"notInventor":[],"owner":[],"notOwner":[],"tags":[],"dates":[],"types":[],"notTypes":[],"j":[],"notJ":[],"fj":[],"notFj":[],"classIpcr":[],"notClassIpcr":[],"classNat":[],"notClassNat":[],"classCpc":[],"notClassCpc":[],"so":[],"notSo":[],"sat":[]},"sequenceFilters":{"s":"SEQIDNO","d":"ASCENDING","p":0,"n":10,"sp":[],"si":[],"len":[],"t":[],"loc":[]}}